 
data_1NRES-TMP
#==============================================================================

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic      2020-11-03
_journal_date_to_coeditor         ?
_journal_date_from_coeditor       ?
_journal_date_accepted     ?
_journal_date_printers_first      ?
_journal_date_printers_final      ?
_journal_date_proofs_out          ?
_journal_date_proofs_in           ?
_journal_coeditor_name            ?
_journal_coeditor_code      YC5029
_journal_coeditor_notes
; ?
;
_journal_paper_category      FA
_journal_techeditor_code      ?
_iucr_compatibility_tag          ACTA95
_journal_techeditor_notes  
;
;
_journal_coden_ASTM               ?
_journal_name_full                ?
_journal_year                     ?
_journal_volume                   ?
_journal_issue                    ?
_journal_page_first               ?
_journal_page_last                ?
_journal_suppl_publ_number        ?
_journal_suppl_publ_pages         ?

#==============================================================================

 
_audit_creation_method            SHELXL-2014
_chemical_name_systematic
;
 ?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H22 N4 O8' 
_chemical_formula_weight          446.41

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            1
_space_group_name_H-M_alt         'P 1'
_space_group_name_Hall            'P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 
_cell_length_a                    7.7162(8)
_cell_length_b                    8.9727(9)
_cell_length_c                    16.9089(17)
_cell_angle_alpha                 86.559(6)
_cell_angle_beta                  78.838(6)
_cell_angle_gamma                 66.314(5)
_cell_volume                      1051.59(19)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     10074 
_cell_measurement_theta_min       3.0 
_cell_measurement_theta_max       27.6 
 
_exptl_crystal_description        Block 
_exptl_crystal_colour             Yellow 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ?              
_exptl_crystal_density_diffrn     1.410          
_exptl_crystal_F_000              468
_exptl_transmission_factor_min    ?                                             
_exptl_transmission_factor_max    ?                                             
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.111
_shelx_estimated_absorpt_T_min    0.978
_shelx_estimated_absorpt_T_max    0.978
_exptl_absorpt_correction_type    'Multi-scan' 
_exptl_absorpt_correction_T_min   0.846 
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication' 
 
_exptl_special_details
;
 ?
;
 
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'                       
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)' 
_diffrn_measurement_method        ? 
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             10971
_diffrn_reflns_av_unetI/netI      0.0442
_diffrn_reflns_av_R_equivalents   0.0171
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.042
_diffrn_reflns_theta_max          27.484
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              9240
_reflns_number_gt                 7362
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          1.000
_reflns_Friedel_fraction_max      0.997
_reflns_Friedel_fraction_full     0.998
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement   'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
 
_refine_special_details
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0388P)²+0.8048P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack    -0.6(15)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          9240
_refine_ls_number_parameters      612
_refine_ls_number_restraints      3
_refine_ls_R_factor_all           0.0673
_refine_ls_R_factor_gt            0.0477
_refine_ls_wR_factor_ref          0.1272
_refine_ls_wR_factor_gt           0.1004
_refine_ls_goodness_of_fit_ref    1.052
_refine_ls_restrained_S_all       1.052
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O13 O 0.2403(5) 0.7004(4) 0.0925(2) 0.0295(7) Uani 1 1 d . . . . .
O14 O 0.2482(5) 1.1162(4) -0.0863(2) 0.0330(8) Uani 1 1 d . . . . .
O15 O 0.0087(5) 0.9269(4) -0.0605(2) 0.0341(8) Uani 1 1 d . . . . .
O16 O -0.0640(5) 1.0132(5) 0.0624(2) 0.0497(11) Uani 1 1 d . . . . .
N2 N 0.0530(5) 0.9533(4) 0.0011(2) 0.0237(8) Uani 1 1 d . . . . .
C12 C 0.3460(6) 0.7766(5) 0.0508(3) 0.0228(9) Uani 1 1 d . . . . .
C8 C 0.3528(6) 0.9931(5) -0.0441(3) 0.0224(9) Uani 1 1 d . . . . .
C9 C 0.5491(6) 0.9460(6) -0.0430(3) 0.0253(10) Uani 1 1 d . . . . .
H9 H 0.6180 1.0011 -0.0732 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2572(6) 0.9049(5) 0.0029(3) 0.0215(9) Uani 1 1 d . . . . .
C11 C 0.5414(6) 0.7308(6) 0.0500(3) 0.0285(10) Uani 1 1 d . . . . .
H11 H 0.6067 0.6435 0.0804 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6379(6) 0.8167(6) 0.0036(3) 0.0274(10) Uani 1 1 d . . . . .
H10 H 0.7681 0.7855 0.0039 0.033 Uiso 1 1 calc R U . . .
O1 O 0.9754(6) 0.6516(5) 0.7402(3) 0.0526(11) Uani 1 1 d . . . . .
O2 O 1.0996(8) 0.0875(5) 0.6836(3) 0.0672(13) Uani 1 1 d . . . . .
H2 H 1.1533 0.1053 0.6395 0.101 Uiso 1 1 calc R U . . .
O3 O 1.1866(5) 0.4996(5) 0.6081(2) 0.0493(10) Uani 1 1 d . . . . .
O4 O 1.2108(7) 0.2629(5) 0.5789(3) 0.0688(13) Uani 1 1 d . . . . .
N4 N 1.1520(6) 0.3796(6) 0.6272(3) 0.0411(11) Uani 1 1 d . . . . .
C19 C 1.0447(7) 0.3712(6) 0.7054(3) 0.0377(11) Uani 1 1 d . . . . .
C20 C 0.9642(8) 0.5062(7) 0.7585(3) 0.0431(14) Uani 1 1 d . . . . .
C22 C 0.8506(9) 0.3498(11) 0.8565(4) 0.067(2) Uani 1 1 d . . . . .
H22 H 0.7852 0.3427 0.9080 0.080 Uiso 1 1 calc R U . . .
C21 C 0.8662(8) 0.4932(9) 0.8349(3) 0.0566(17) Uani 1 1 d . . . . .
H21 H 0.8117 0.5815 0.8708 0.068 Uiso 1 1 calc R U . . .
C23 C 0.9266(9) 0.2149(9) 0.8063(4) 0.0622(18) Uani 1 1 d . . . . .
H23 H 0.9117 0.1197 0.8235 0.075 Uiso 1 1 calc R U . . .
C24 C 1.0248(9) 0.2230(7) 0.7301(4) 0.0499(15) Uani 1 1 d . . . . .
O5 O 0.7411(5) 0.6261(4) 0.6045(2) 0.0300(8) Uani 1 1 d . . . . .
O6 O 0.7682(5) 1.0207(4) 0.4128(2) 0.0310(8) Uani 1 1 d . . . . .
O8 O 0.9636(5) 0.8369(4) 0.58108(19) 0.0300(7) Uani 1 1 d . . . . .
O7 O 1.0709(5) 0.7287(4) 0.4619(2) 0.0351(8) Uani 1 1 d . . . . .
N3 N 0.9395(5) 0.7946(4) 0.5183(2) 0.0222(8) Uani 1 1 d . . . . .
C3 C 0.4588(6) 0.7747(5) 0.5461(3) 0.0251(10) Uani 1 1 d . . . . .
H3 H 0.3890 0.7203 0.5765 0.030 Uiso 1 1 calc R U . . .
C2 C 0.6454(6) 0.7394(5) 0.5556(3) 0.0213(9) Uani 1 1 d . . . . .
C6 C 0.6616(6) 0.9427(5) 0.4541(3) 0.0233(9) Uani 1 1 d . . . . .
C1 C 0.7433(6) 0.8259(5) 0.5087(2) 0.0196(9) Uani 1 1 d . . . . .
C5 C 0.4746(7) 0.9750(6) 0.4458(3) 0.0276(10) Uani 1 1 d . . . . .
H5A H 0.4160 1.0525 0.4096 0.033 Uiso 1 1 calc R U . . .
C4 C 0.3755(7) 0.8906(6) 0.4918(3) 0.0286(10) Uani 1 1 d . . . . .
H4 H 0.2502 0.9125 0.4860 0.034 Uiso 1 1 calc R U . . .
O10 O 0.0478(6) 0.0879(5) 0.2066(3) 0.0436(9) Uani 1 1 d . . . . .
O12 O -0.0521(8) 0.3087(6) 0.1000(3) 0.0713(14) Uani 1 1 d . . . . .
O11 O -0.0531(7) 0.5450(6) 0.1136(3) 0.0694(14) Uani 1 1 d . . . . .
O9 O -0.0419(7) 0.6486(5) 0.2502(3) 0.0676(13) Uani 1 1 d . . . . .
H9A H -0.0674 0.6619 0.2047 0.101 Uiso 1 1 calc R U . . .
N1 N -0.0378(7) 0.4107(6) 0.1414(3) 0.0468(12) Uani 1 1 d . . . . .
C15 C 0.0203(7) 0.4565(7) 0.3504(4) 0.0490(15) Uani 1 1 d . . . . .
H15 H 0.0153 0.5364 0.3844 0.059 Uiso 1 1 calc R U . . .
C16 C 0.0572(7) 0.3014(7) 0.3783(3) 0.0411(13) Uani 1 1 d . . . . .
H16 H 0.0765 0.2782 0.4311 0.049 Uiso 1 1 calc R U . . .
C18 C 0.0351(6) 0.2127(6) 0.2507(3) 0.0304(11) Uani 1 1 d . . . . .
C13 C -0.0041(7) 0.3726(6) 0.2227(3) 0.0355(11) Uani 1 1 d . . . . .
C17 C 0.0661(7) 0.1784(6) 0.3289(3) 0.0370(11) Uani 1 1 d . . . . .
H17 H 0.0928 0.0740 0.3485 0.044 Uiso 1 1 calc R U . . .
C14 C -0.0094(7) 0.4948(6) 0.2724(4) 0.0412(13) Uani 1 1 d . . . . .
N5 N 0.5430(5) 0.4698(4) 0.6985(2) 0.0228(8) Uani 1 1 d . . . . .
N6 N 0.4206(5) 0.2833(4) 0.8119(2) 0.0219(8) Uani 1 1 d . . . . .
C32 C 0.6938(8) 0.2482(6) 0.5993(3) 0.0326(11) Uani 1 1 d . . . . .
H32A H 0.6101 0.2325 0.5684 0.049 Uiso 1 1 calc R U . . .
H32B H 0.7981 0.1459 0.6044 0.049 Uiso 1 1 calc R U . . .
H32C H 0.7442 0.3236 0.5726 0.049 Uiso 1 1 calc R U . . .
C28 C 0.2633(8) 0.5079(6) 0.9097(3) 0.0351(11) Uani 1 1 d . . . . .
H28A H 0.1474 0.5992 0.9033 0.053 Uiso 1 1 calc R U . . .
H28B H 0.3380 0.5425 0.9378 0.053 Uiso 1 1 calc R U . . .
H28C H 0.2309 0.4259 0.9401 0.053 Uiso 1 1 calc R U . . .
C29 C 0.5649(8) 0.0434(6) 0.7240(3) 0.0379(12) Uani 1 1 d . . . . .
H29A H 0.6982 -0.0213 0.7250 0.057 Uiso 1 1 calc R U . . .
H29B H 0.5381 0.0317 0.6721 0.057 Uiso 1 1 calc R U . . .
H29C H 0.4859 0.0077 0.7650 0.057 Uiso 1 1 calc R U . . .
C25 C 0.3960(8) 0.7096(6) 0.7856(3) 0.0355(12) Uani 1 1 d . . . . .
H25A H 0.4528 0.7522 0.7390 0.053 Uiso 1 1 calc R U . . .
H25B H 0.4480 0.7189 0.8313 0.053 Uiso 1 1 calc R U . . .
H25C H 0.2591 0.7702 0.7961 0.053 Uiso 1 1 calc R U . . .
C31 C 0.5828(6) 0.3145(5) 0.6814(3) 0.0238(9) Uani 1 1 d . . . . .
C27 C 0.3785(6) 0.4391(5) 0.8282(3) 0.0226(9) Uani 1 1 d . . . . .
C26 C 0.4401(6) 0.5343(5) 0.7703(3) 0.0229(9) Uani 1 1 d . . . . .
C30 C 0.5220(6) 0.2188(5) 0.7393(3) 0.0233(9) Uani 1 1 d . . . . .
N8 N 0.4285(5) 0.4716(4) 0.1947(2) 0.0251(8) Uani 1 1 d . . . . .
N7 N 0.5741(5) 0.2446(4) 0.3074(2) 0.0235(8) Uani 1 1 d . . . . .
C37 C 0.4592(8) 0.2652(6) 0.0994(3) 0.0342(11) Uani 1 1 d . . . . .
H37A H 0.3927 0.3614 0.0714 0.051 Uiso 1 1 calc R U . . .
H37B H 0.3866 0.1983 0.1077 0.051 Uiso 1 1 calc R U . . .
H37C H 0.5841 0.2055 0.0678 0.051 Uiso 1 1 calc R U . . .
C36 C 0.3792(8) 0.6985(6) 0.2802(3) 0.0380(12) Uani 1 1 d . . . . .
H36A H 0.3530 0.7553 0.2311 0.057 Uiso 1 1 calc R U . . .
H36B H 0.4785 0.7188 0.2982 0.057 Uiso 1 1 calc R U . . .
H36C H 0.2643 0.7360 0.3207 0.057 Uiso 1 1 calc R U . . .
C33 C 0.5342(7) 0.4498(6) 0.4038(3) 0.0317(11) Uani 1 1 d . . . . .
H33A H 0.4092 0.4911 0.4378 0.047 Uiso 1 1 calc R U . . .
H33B H 0.5853 0.5321 0.3977 0.047 Uiso 1 1 calc R U . . .
H33C H 0.6186 0.3557 0.4278 0.047 Uiso 1 1 calc R U . . .
C38 C 0.4811(6) 0.3123(5) 0.1793(3) 0.0230(9) Uani 1 1 d . . . . .
C34 C 0.5176(6) 0.4036(5) 0.3229(3) 0.0228(9) Uani 1 1 d . . . . .
C35 C 0.4445(6) 0.5192(5) 0.2654(3) 0.0242(10) Uani 1 1 d . . . . .
C39 C 0.5556(6) 0.1978(5) 0.2366(3) 0.0226(9) Uani 1 1 d . . . . .
C40 C 0.6157(8) 0.0185(6) 0.2227(3) 0.0348(12) Uani 1 1 d . . . . .
H40A H 0.7030 -0.0419 0.2578 0.052 Uiso 1 1 calc R U . . .
H40B H 0.6783 -0.0099 0.1676 0.052 Uiso 1 1 calc R U . . .
H40C H 0.5040 -0.0072 0.2339 0.052 Uiso 1 1 calc R U . . .
H5 H 0.656(9) 0.569(7) 0.636(4) 0.058(19) Uiso 1 1 d . . . . .
H6 H 0.714(8) 1.079(6) 0.382(3) 0.031(15) Uiso 1 1 d . . . . .
H13 H 0.321(10) 0.617(8) 0.125(4) 0.07(2) Uiso 1 1 d . . . . .
H14 H 0.302(7) 1.165(6) -0.107(3) 0.027(14) Uiso 1 1 d . . . . .
H10A H 0.017(10) 0.117(8) 0.164(4) 0.06(2) Uiso 1 1 d . . . . .
H1 H 1.026(8) 0.645(7) 0.694(3) 0.032(16) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O13 C12 1.341(6) . ?
O13 H13 0.98(7) . ?
O14 C8 1.339(5) . ?
O14 H14 0.75(5) . ?
O15 N2 1.220(5) . ?
O16 N2 1.222(5) . ?
N2 C7 1.463(5) . ?
C12 C7 1.386(6) . ?
C12 C11 1.392(6) . ?
C8 C7 1.403(6) . ?
C8 C9 1.403(6) . ?
C9 C10 1.377(6) . ?
C9 H9 0.9300 . ?
C11 C10 1.388(7) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
O1 C20 1.355(7) . ?
O1 H1 0.79(5) . ?
O2 C24 1.343(8) . ?
O2 H2 0.8200 . ?
O3 N4 1.222(6) . ?
O4 N4 1.244(6) . ?
N4 C19 1.433(7) . ?
C19 C20 1.405(7) . ?
C19 C24 1.428(8) . ?
C20 C21 1.388(8) . ?
C22 C21 1.362(10) . ?
C22 C23 1.375(10) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C23 C24 1.376(9) . ?
C23 H23 0.9300 . ?
O5 C2 1.340(5) . ?
O5 H5 1.04(6) . ?
O6 C6 1.355(5) . ?
O6 H6 0.78(5) . ?
O8 N3 1.219(5) . ?
O7 N3 1.224(5) . ?
N3 C1 1.465(5) . ?
C3 C2 1.384(6) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9300 . ?
C2 C1 1.402(6) . ?
C6 C5 1.387(6) . ?
C6 C1 1.388(6) . ?
C5 C4 1.389(7) . ?
C5 H5A 0.9300 . ?
C4 H4 0.9300 . ?
O10 C18 1.343(6) . ?
O10 H10A 0.80(7) . ?
O12 N1 1.236(6) . ?
O11 N1 1.236(6) . ?
O9 C14 1.344(6) . ?
O9 H9A 0.8200 . ?
N1 C13 1.443(7) . ?
C15 C16 1.377(8) . ?
C15 C14 1.380(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(7) . ?
C16 H16 0.9300 . ?
C18 C17 1.384(7) . ?
C18 C13 1.414(7) . ?
C13 C14 1.405(7) . ?
C17 H17 0.9300 . ?
N5 C26 1.334(6) . ?
N5 C31 1.339(5) . ?
N6 C27 1.334(5) . ?
N6 C30 1.343(6) . ?
C32 C31 1.497(6) . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C28 C27 1.502(6) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C29 C30 1.500(6) . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C25 C26 1.497(6) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C31 C30 1.400(6) . ?
C27 C26 1.400(6) . ?
N8 C35 1.338(6) . ?
N8 C38 1.346(6) . ?
N7 C34 1.340(6) . ?
N7 C39 1.343(6) . ?
C37 C38 1.499(6) . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C36 C35 1.501(6) . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?
C33 C34 1.496(6) . ?
C33 H33A 0.9600 . ?
C33 H33B 0.9600 . ?
C33 H33C 0.9600 . ?
C38 C39 1.396(6) . ?
C34 C35 1.399(6) . ?
C39 C40 1.504(6) . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C12 O13 H13 108(4) . . ?
C8 O14 H14 113(4) . . ?
O15 N2 O16 123.4(4) . . ?
O15 N2 C7 118.5(4) . . ?
O16 N2 C7 118.1(4) . . ?
O13 C12 C7 118.0(4) . . ?
O13 C12 C11 124.1(4) . . ?
C7 C12 C11 117.9(4) . . ?
O14 C8 C7 117.0(4) . . ?
O14 C8 C9 125.3(4) . . ?
C7 C8 C9 117.7(4) . . ?
C10 C9 C8 118.8(4) . . ?
C10 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C12 C7 C8 123.4(4) . . ?
C12 C7 N2 119.0(4) . . ?
C8 C7 N2 117.6(4) . . ?
C10 C11 C12 119.3(4) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C9 C10 C11 122.9(4) . . ?
C9 C10 H10 118.6 . . ?
C11 C10 H10 118.6 . . ?
C20 O1 H1 106(4) . . ?
C24 O2 H2 109.5 . . ?
O3 N4 O4 120.1(5) . . ?
O3 N4 C19 120.5(5) . . ?
O4 N4 C19 119.4(5) . . ?
C20 C19 C24 119.9(5) . . ?
C20 C19 N4 120.3(5) . . ?
C24 C19 N4 119.7(5) . . ?
O1 C20 C21 116.8(6) . . ?
O1 C20 C19 124.0(5) . . ?
C21 C20 C19 119.2(6) . . ?
C21 C22 C23 123.4(6) . . ?
C21 C22 H22 118.3 . . ?
C23 C22 H22 118.3 . . ?
C22 C21 C20 119.3(6) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C22 C23 C24 119.1(7) . . ?
C22 C23 H23 120.5 . . ?
C24 C23 H23 120.5 . . ?
O2 C24 C23 117.1(6) . . ?
O2 C24 C19 123.8(6) . . ?
C23 C24 C19 119.1(6) . . ?
C2 O5 H5 111(3) . . ?
C6 O6 H6 111(4) . . ?
O8 N3 O7 123.5(4) . . ?
O8 N3 C1 118.8(4) . . ?
O7 N3 C1 117.7(4) . . ?
C2 C3 C4 120.3(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
O5 C2 C3 125.0(4) . . ?
O5 C2 C1 117.6(4) . . ?
C3 C2 C1 117.4(4) . . ?
O6 C6 C5 123.6(4) . . ?
O6 C6 C1 118.1(4) . . ?
C5 C6 C1 118.3(4) . . ?
C6 C1 C2 123.0(4) . . ?
C6 C1 N3 118.0(4) . . ?
C2 C1 N3 119.0(4) . . ?
C6 C5 C4 119.5(4) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C18 O10 H10A 112(5) . . ?
C14 O9 H9A 109.5 . . ?
O12 N1 O11 120.2(5) . . ?
O12 N1 C13 119.7(5) . . ?
O11 N1 C13 120.1(5) . . ?
C16 C15 C14 120.8(5) . . ?
C16 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C15 C16 C17 121.2(5) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
O10 C18 C17 116.3(5) . . ?
O10 C18 C13 125.0(5) . . ?
C17 C18 C13 118.7(5) . . ?
C14 C13 C18 121.1(5) . . ?
C14 C13 N1 119.4(5) . . ?
C18 C13 N1 119.5(5) . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.1 . . ?
C16 C17 H17 120.1 . . ?
O9 C14 C15 116.6(5) . . ?
O9 C14 C13 124.9(6) . . ?
C15 C14 C13 118.5(5) . . ?
C26 N5 C31 119.5(4) . . ?
C27 N6 C30 119.4(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 H29A 109.5 . . ?
C30 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C30 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N5 C31 C30 120.2(4) . . ?
N5 C31 C32 117.9(4) . . ?
C30 C31 C32 121.9(4) . . ?
N6 C27 C26 120.4(4) . . ?
N6 C27 C28 118.0(4) . . ?
C26 C27 C28 121.6(4) . . ?
N5 C26 C27 120.3(4) . . ?
N5 C26 C25 117.3(4) . . ?
C27 C26 C25 122.4(4) . . ?
N6 C30 C31 120.1(4) . . ?
N6 C30 C29 117.3(4) . . ?
C31 C30 C29 122.6(4) . . ?
C35 N8 C38 119.8(4) . . ?
C34 N7 C39 119.1(4) . . ?
C38 C37 H37A 109.5 . . ?
C38 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C38 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C35 C36 H36A 109.5 . . ?
C35 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C35 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C34 C33 H33A 109.5 . . ?
C34 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C34 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
N8 C38 C39 119.7(4) . . ?
N8 C38 C37 117.8(4) . . ?
C39 C38 C37 122.5(4) . . ?
N7 C34 C35 120.6(4) . . ?
N7 C34 C33 117.0(4) . . ?
C35 C34 C33 122.5(4) . . ?
N8 C35 C34 120.1(4) . . ?
N8 C35 C36 117.5(4) . . ?
C34 C35 C36 122.4(4) . . ?
N7 C39 C38 120.8(4) . . ?
N7 C39 C40 117.3(4) . . ?
C38 C39 C40 121.9(4) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O14 C8 C9 C10 179.9(4) . . . . ?
C7 C8 C9 C10 0.1(6) . . . . ?
O13 C12 C7 C8 -179.3(4) . . . . ?
C11 C12 C7 C8 -1.9(7) . . . . ?
O13 C12 C7 N2 1.2(6) . . . . ?
C11 C12 C7 N2 178.6(4) . . . . ?
O14 C8 C7 C12 -178.8(4) . . . . ?
C9 C8 C7 C12 1.1(7) . . . . ?
O14 C8 C7 N2 0.7(6) . . . . ?
C9 C8 C7 N2 -179.5(4) . . . . ?
O15 N2 C7 C12 -110.4(5) . . . . ?
O16 N2 C7 C12 67.3(6) . . . . ?
O15 N2 C7 C8 70.1(5) . . . . ?
O16 N2 C7 C8 -112.2(5) . . . . ?
O13 C12 C11 C10 178.9(4) . . . . ?
C7 C12 C11 C10 1.6(7) . . . . ?
C8 C9 C10 C11 -0.3(7) . . . . ?
C12 C11 C10 C9 -0.6(7) . . . . ?
O3 N4 C19 C20 5.3(7) . . . . ?
O4 N4 C19 C20 -175.0(5) . . . . ?
O3 N4 C19 C24 -172.7(4) . . . . ?
O4 N4 C19 C24 6.9(7) . . . . ?
C24 C19 C20 O1 -179.8(5) . . . . ?
N4 C19 C20 O1 2.1(7) . . . . ?
C24 C19 C20 C21 0.1(7) . . . . ?
N4 C19 C20 C21 -177.9(5) . . . . ?
C23 C22 C21 C20 -0.4(9) . . . . ?
O1 C20 C21 C22 -179.9(5) . . . . ?
C19 C20 C21 C22 0.1(8) . . . . ?
C21 C22 C23 C24 0.4(9) . . . . ?
C22 C23 C24 O2 178.8(5) . . . . ?
C22 C23 C24 C19 -0.2(8) . . . . ?
C20 C19 C24 O2 -179.0(5) . . . . ?
N4 C19 C24 O2 -1.0(7) . . . . ?
C20 C19 C24 C23 -0.1(8) . . . . ?
N4 C19 C24 C23 178.0(5) . . . . ?
C4 C3 C2 O5 -177.8(4) . . . . ?
C4 C3 C2 C1 0.4(6) . . . . ?
O6 C6 C1 C2 179.0(4) . . . . ?
C5 C6 C1 C2 0.1(7) . . . . ?
O6 C6 C1 N3 0.1(6) . . . . ?
C5 C6 C1 N3 -178.9(4) . . . . ?
O5 C2 C1 C6 178.1(4) . . . . ?
C3 C2 C1 C6 -0.3(6) . . . . ?
O5 C2 C1 N3 -3.0(6) . . . . ?
C3 C2 C1 N3 178.6(4) . . . . ?
O8 N3 C1 C6 110.2(5) . . . . ?
O7 N3 C1 C6 -68.9(5) . . . . ?
O8 N3 C1 C2 -68.8(5) . . . . ?
O7 N3 C1 C2 112.1(5) . . . . ?
O6 C6 C5 C4 -178.9(4) . . . . ?
C1 C6 C5 C4 0.0(7) . . . . ?
C2 C3 C4 C5 -0.3(7) . . . . ?
C6 C5 C4 C3 0.1(7) . . . . ?
C14 C15 C16 C17 0.1(8) . . . . ?
O10 C18 C13 C14 -178.2(4) . . . . ?
C17 C18 C13 C14 0.8(7) . . . . ?
O10 C18 C13 N1 1.3(7) . . . . ?
C17 C18 C13 N1 -179.7(4) . . . . ?
O12 N1 C13 C14 -172.9(5) . . . . ?
O11 N1 C13 C14 6.8(7) . . . . ?
O12 N1 C13 C18 7.6(7) . . . . ?
O11 N1 C13 C18 -172.7(5) . . . . ?
O10 C18 C17 C16 179.4(5) . . . . ?
C13 C18 C17 C16 0.3(7) . . . . ?
C15 C16 C17 C18 -0.8(7) . . . . ?
C16 C15 C14 O9 -179.2(5) . . . . ?
C16 C15 C14 C13 1.0(7) . . . . ?
C18 C13 C14 O9 178.7(4) . . . . ?
N1 C13 C14 O9 -0.8(7) . . . . ?
C18 C13 C14 C15 -1.5(7) . . . . ?
N1 C13 C14 C15 179.0(5) . . . . ?
C26 N5 C31 C30 -1.9(6) . . . . ?
C26 N5 C31 C32 178.3(4) . . . . ?
C30 N6 C27 C26 -0.3(6) . . . . ?
C30 N6 C27 C28 179.4(4) . . . . ?
C31 N5 C26 C27 1.7(6) . . . . ?
C31 N5 C26 C25 -178.6(4) . . . . ?
N6 C27 C26 N5 -0.6(6) . . . . ?
C28 C27 C26 N5 179.7(4) . . . . ?
N6 C27 C26 C25 179.8(4) . . . . ?
C28 C27 C26 C25 0.1(7) . . . . ?
C27 N6 C30 C31 0.0(6) . . . . ?
C27 N6 C30 C29 -179.8(4) . . . . ?
N5 C31 C30 N6 1.1(6) . . . . ?
C32 C31 C30 N6 -179.2(4) . . . . ?
N5 C31 C30 C29 -179.1(4) . . . . ?
C32 C31 C30 C29 0.7(7) . . . . ?
C35 N8 C38 C39 -1.3(6) . . . . ?
C35 N8 C38 C37 179.6(4) . . . . ?
C39 N7 C34 C35 -1.5(6) . . . . ?
C39 N7 C34 C33 177.7(4) . . . . ?
C38 N8 C35 C34 0.6(6) . . . . ?
C38 N8 C35 C36 -178.5(4) . . . . ?
N7 C34 C35 N8 0.8(6) . . . . ?
C33 C34 C35 N8 -178.4(4) . . . . ?
N7 C34 C35 C36 179.9(4) . . . . ?
C33 C34 C35 C36 0.7(7) . . . . ?
C34 N7 C39 C38 0.9(6) . . . . ?
C34 N7 C39 C40 -178.3(4) . . . . ?
N8 C38 C39 N7 0.5(6) . . . . ?
C37 C38 C39 N7 179.6(4) . . . . ?
N8 C38 C39 C40 179.7(4) . . . . ?
C37 C38 C39 C40 -1.2(7) . . . . ?
 
_refine_diff_density_max    0.265
_refine_diff_density_min   -0.238
_refine_diff_density_rms    0.045

_shelxl_version_number 2014-3


 
data_2NRES-TMP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C6 H5 N O4, 1.5(C8 H12 N2)'
_chemical_formula_sum
 'C18 H23 N4 O4' 
_chemical_formula_weight          359.40

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.658(2)
_cell_length_b                    9.277(3)
_cell_length_c                    15.152(5)
_cell_angle_alpha                 79.304(6)
_cell_angle_beta                  82.008(6)
_cell_angle_gamma                 65.214(5)
_cell_volume                      957.9(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     5527
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.7
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.246          
_exptl_crystal_F_000              382
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.090
_shelx_estimated_absorpt_T_min    0.982
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.683
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             6882
_diffrn_reflns_av_unetI/netI      0.0706
_diffrn_reflns_av_R_equivalents   0.0589
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.965
_diffrn_reflns_theta_max          25.000
_diffrn_reflns_theta_full         25.000
_diffrn_measured_fraction_theta_max   0.987
_diffrn_measured_fraction_theta_full  0.987
_diffrn_reflns_Laue_measured_fraction_max    0.987
_diffrn_reflns_Laue_measured_fraction_full   0.987
_diffrn_reflns_point_group_measured_fraction_max   0.987
_diffrn_reflns_point_group_measured_fraction_full  0.987
_reflns_number_total              3305
_reflns_number_gt                 1894
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1220P)²+0.3342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.020(8)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3305
_refine_ls_number_parameters      247
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1270
_refine_ls_R_factor_gt            0.0781
_refine_ls_wR_factor_ref          0.2532
_refine_ls_wR_factor_gt           0.2296
_refine_ls_goodness_of_fit_ref    1.109
_refine_ls_restrained_S_all       1.109
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O2 O 0.0736(4) 0.6091(4) 0.6982(2) 0.0558(9) Uani 1 1 d . . . . .
H2 H 0.063749 0.694471 0.667492 0.084 Uiso 1 1 calc R U . . .
O1 O 0.4591(5) 0.1968(4) 0.9072(2) 0.0594(10) Uani 1 1 d . . . . .
N1 N 0.8110(5) 0.0571(4) 0.9808(2) 0.0460(10) Uani 1 1 d . . . . .
N2 N 0.0330(5) 0.8706(4) 0.5667(2) 0.0417(9) Uani 1 1 d . . . . .
N4 N 0.1161(5) 0.3582(4) 0.8311(3) 0.0454(9) Uani 1 1 d . . . . .
O4 O -0.0012(6) 0.4247(5) 0.8885(3) 0.0847(13) Uani 1 1 d . . . . .
N3 N 0.4585(5) 0.1495(4) 0.4485(3) 0.0499(10) Uani 1 1 d . . . . .
C2 C 0.2505(6) 0.5352(5) 0.7326(3) 0.0396(10) Uani 1 1 d . . . . .
C6 C 0.4516(6) 0.3189(5) 0.8416(3) 0.0413(10) Uani 1 1 d . . . . .
C12 C 0.0183(5) 0.8559(5) 0.4815(3) 0.0382(10) Uani 1 1 d . . . . .
C1 C 0.2772(6) 0.4050(5) 0.8002(2) 0.0374(10) Uani 1 1 d . . . . .
C13 C 0.0167(6) 1.0116(5) 0.5863(3) 0.0404(10) Uani 1 1 d . . . . .
C16 C 0.4877(6) 0.1261(5) 0.5365(3) 0.0449(11) Uani 1 1 d . . . . .
C17 C 0.4700(6) 0.0246(5) 0.4112(3) 0.0453(11) Uani 1 1 d . . . . .
C3 C 0.4047(6) 0.5778(5) 0.7036(3) 0.0449(11) Uani 1 1 d . . . . .
H3 H 0.391161 0.663619 0.658206 0.054 Uiso 1 1 calc R U . . .
C8 C 0.9390(6) -0.0818(5) 0.9550(3) 0.0444(11) Uani 1 1 d . . . . .
O3 O 0.1069(6) 0.2522(6) 0.7987(3) 0.1051(16) Uani 1 1 d . . . . .
C5 C 0.6034(6) 0.3644(5) 0.8106(3) 0.0487(11) Uani 1 1 d . . . . .
H5 H 0.721908 0.308864 0.835766 0.058 Uiso 1 1 calc R U . . .
C9 C 0.8692(6) 0.1410(5) 1.0252(3) 0.0466(11) Uani 1 1 d . . . . .
C4 C 0.5787(6) 0.4918(5) 0.7427(3) 0.0502(12) Uani 1 1 d . . . . .
H4 H 0.681737 0.520521 0.722736 0.060 Uiso 1 1 calc R U . . .
C7 C 0.8639(8) -0.1719(6) 0.9075(3) 0.0601(13) Uani 1 1 d . . . . .
H7A H 0.868205 -0.267750 0.946088 0.090 Uiso 1 1 calc R U . . .
H7B H 0.942536 -0.199802 0.853017 0.090 Uiso 1 1 calc R U . . .
H7C H 0.733239 -0.105245 0.893241 0.090 Uiso 1 1 calc R U . . .
C14 C 0.0339(8) 1.0218(6) 0.6825(3) 0.0583(13) Uani 1 1 d . . . . .
H14A H -0.088596 1.091322 0.707349 0.087 Uiso 1 1 calc R U . . .
H14B H 0.128155 1.063902 0.684649 0.087 Uiso 1 1 calc R U . . .
H14C H 0.073084 0.916779 0.716990 0.087 Uiso 1 1 calc R U . . .
C11 C 0.0387(7) 0.6950(5) 0.4640(3) 0.0583(13) Uani 1 1 d . . . . .
H11A H 0.168328 0.636130 0.441392 0.087 Uiso 1 1 calc R U . . .
H11B H -0.049326 0.709853 0.420406 0.087 Uiso 1 1 calc R U . . .
H11C H 0.010015 0.636255 0.519075 0.087 Uiso 1 1 calc R U . . .
C18 C 0.4373(8) 0.0547(7) 0.3141(3) 0.0669(14) Uani 1 1 d . . . . .
H18A H 0.316031 0.052284 0.306902 0.100 Uiso 1 1 calc R U . . .
H18B H 0.539209 -0.026601 0.283964 0.100 Uiso 1 1 calc R U . . .
H18C H 0.435495 0.158060 0.288469 0.100 Uiso 1 1 calc R U . . .
C10 C 0.7187(7) 0.2954(6) 1.0520(4) 0.0674(15) Uani 1 1 d . . . . .
H10A H 0.598738 0.317296 1.028405 0.101 Uiso 1 1 calc R U . . .
H10B H 0.758625 0.381131 1.028407 0.101 Uiso 1 1 calc R U . . .
H10C H 0.702353 0.286712 1.116517 0.101 Uiso 1 1 calc R U . . .
C15 C 0.4711(8) 0.2696(6) 0.5761(4) 0.0678(15) Uani 1 1 d . . . . .
H15A H 0.464801 0.355521 0.528504 0.102 Uiso 1 1 calc R U . . .
H15B H 0.581634 0.240866 0.609411 0.102 Uiso 1 1 calc R U . . .
H15C H 0.356311 0.303708 0.615612 0.102 Uiso 1 1 calc R U . . .
H1 H 0.568(11) 0.138(9) 0.920(5) 0.12(3) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O2 C2 1.365(5) . ?
O2 H2 0.8200 . ?
O1 C6 1.348(5) . ?
O1 H1 0.81(7) . ?
N1 C8 1.340(5) . ?
N1 C9 1.352(6) . ?
N2 C13 1.346(5) . ?
N2 C12 1.347(5) . ?
N4 O3 1.207(5) . ?
N4 O4 1.209(5) . ?
N4 C1 1.464(5) . ?
N3 C16 1.344(5) . ?
N3 C17 1.347(5) . ?
C2 C3 1.388(6) . ?
C2 C1 1.393(5) . ?
C6 C5 1.391(6) . ?
C6 C1 1.402(5) . ?
C12 C13 1.404(6) 2_576 ?
C12 C11 1.504(6) . ?
C13 C14 1.506(6) . ?
C16 C17 1.404(6) 2_656 ?
C16 C15 1.511(6) . ?
C17 C18 1.482(6) . ?
C3 C4 1.385(6) . ?
C3 H3 0.9300 . ?
C8 C9 1.390(6) 2_757 ?
C8 C7 1.513(6) . ?
C5 C4 1.380(6) . ?
C5 H5 0.9300 . ?
C9 C10 1.499(6) . ?
C4 H4 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 O2 H2 109.5 . . ?
C6 O1 H1 113(5) . . ?
C8 N1 C9 119.8(4) . . ?
C13 N2 C12 120.0(3) . . ?
O3 N4 O4 122.3(4) . . ?
O3 N4 C1 118.3(4) . . ?
O4 N4 C1 119.3(4) . . ?
C16 N3 C17 118.6(4) . . ?
O2 C2 C3 124.8(3) . . ?
O2 C2 C1 116.7(4) . . ?
C3 C2 C1 118.4(4) . . ?
O1 C6 C5 125.4(4) . . ?
O1 C6 C1 117.1(4) . . ?
C5 C6 C1 117.5(4) . . ?
N2 C12 C13 119.8(4) . 2_576 ?
N2 C12 C11 117.3(4) . . ?
C13 C12 C11 122.9(4) 2_576 . ?
C2 C1 C6 122.5(4) . . ?
C2 C1 N4 119.0(3) . . ?
C6 C1 N4 118.5(3) . . ?
N2 C13 C12 120.2(4) . 2_576 ?
N2 C13 C14 117.9(3) . . ?
C12 C13 C14 121.9(4) 2_576 . ?
N3 C16 C17 121.3(4) . 2_656 ?
N3 C16 C15 116.9(4) . . ?
C17 C16 C15 121.8(4) 2_656 . ?
N3 C17 C16 120.2(4) . 2_656 ?
N3 C17 C18 117.1(4) . . ?
C16 C17 C18 122.7(4) 2_656 . ?
C4 C3 C2 119.6(4) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
N1 C8 C9 120.3(4) . 2_757 ?
N1 C8 C7 117.2(4) . . ?
C9 C8 C7 122.4(4) 2_757 . ?
C4 C5 C6 120.2(4) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
N1 C9 C8 119.9(4) . 2_757 ?
N1 C9 C10 117.1(4) . . ?
C8 C9 C10 123.1(4) 2_757 . ?
C5 C4 C3 121.7(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C16 C15 H15A 109.5 . . ?
C16 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C16 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C13 N2 C12 C13 -0.9(6) . . . 2_576 ?
C13 N2 C12 C11 179.7(4) . . . . ?
O2 C2 C1 C6 -179.8(4) . . . . ?
C3 C2 C1 C6 2.0(6) . . . . ?
O2 C2 C1 N4 -1.4(6) . . . . ?
C3 C2 C1 N4 -179.6(4) . . . . ?
O1 C6 C1 C2 178.9(4) . . . . ?
C5 C6 C1 C2 -2.2(6) . . . . ?
O1 C6 C1 N4 0.5(6) . . . . ?
C5 C6 C1 N4 179.4(4) . . . . ?
O3 N4 C1 C2 96.0(5) . . . . ?
O4 N4 C1 C2 -85.0(5) . . . . ?
O3 N4 C1 C6 -85.6(5) . . . . ?
O4 N4 C1 C6 93.5(5) . . . . ?
C12 N2 C13 C12 0.9(6) . . . 2_576 ?
C12 N2 C13 C14 179.9(4) . . . . ?
C17 N3 C16 C17 0.2(7) . . . 2_656 ?
C17 N3 C16 C15 -179.3(4) . . . . ?
C16 N3 C17 C16 -0.2(7) . . . 2_656 ?
C16 N3 C17 C18 -179.9(4) . . . . ?
O2 C2 C3 C4 -178.8(4) . . . . ?
C1 C2 C3 C4 -0.6(6) . . . . ?
C9 N1 C8 C9 0.8(6) . . . 2_757 ?
C9 N1 C8 C7 178.6(4) . . . . ?
O1 C6 C5 C4 179.9(4) . . . . ?
C1 C6 C5 C4 1.1(6) . . . . ?
C8 N1 C9 C8 -0.8(6) . . . 2_757 ?
C8 N1 C9 C10 180.0(4) . . . . ?
C6 C5 C4 C3 0.1(7) . . . . ?
C2 C3 C4 C5 -0.4(7) . . . . ?
 
_refine_diff_density_max    0.267
_refine_diff_density_min   -0.248
_refine_diff_density_rms    0.064


 
data_3NRES-ACR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C32 H23 N3 O3.99' 
_chemical_formula_weight          513.33

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    9.2447(9)
_cell_length_b                    14.4694(13)
_cell_length_c                    19.3202(18)
_cell_angle_alpha                 93.232(7)
_cell_angle_beta                  102.634(7)
_cell_angle_gamma                 97.795(7)
_cell_volume                      2488.6(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     20527
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.370          
_exptl_crystal_F_000              1072
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.290
_exptl_crystal_size_mid           0.220
_exptl_crystal_size_min           0.170
_exptl_absorpt_coefficient_mu     0.092
_shelx_estimated_absorpt_T_min    0.974
_shelx_estimated_absorpt_T_max    0.985
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.762
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             25721
_diffrn_reflns_av_unetI/netI      0.0601
_diffrn_reflns_av_R_equivalents   0.0450
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -18
_diffrn_reflns_limit_k_max        18
_diffrn_reflns_limit_l_min        -24
_diffrn_reflns_limit_l_max        25
_diffrn_reflns_theta_min          3.042
_diffrn_reflns_theta_max          27.484
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              11355
_reflns_number_gt                 7523
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0665P)²+0.7465P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          11355
_refine_ls_number_parameters      729
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0890
_refine_ls_R_factor_gt            0.0567
_refine_ls_wR_factor_ref          0.1588
_refine_ls_wR_factor_gt           0.1419
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 1.02767(19) 0.09475(10) 0.43919(8) 0.0241(4) Uani 1 1 d . . . . .
C40 C 0.8842(2) 0.11091(13) 0.42520(10) 0.0249(4) Uani 1 1 d . . . . .
C41 C 0.7959(3) 0.09336(15) 0.35405(11) 0.0346(5) Uani 1 1 d . . . . .
H41 H 0.838130 0.071641 0.317946 0.041 Uiso 1 1 calc R U . . .
C42 C 0.6510(3) 0.10808(16) 0.33857(13) 0.0426(6) Uani 1 1 d . . . . .
H42 H 0.594862 0.096223 0.291924 0.051 Uiso 1 1 calc R U . . .
C43 C 0.5838(3) 0.14139(16) 0.39269(14) 0.0428(6) Uani 1 1 d . . . . .
H43 H 0.484524 0.151522 0.381117 0.051 Uiso 1 1 calc R U . . .
C44 C 0.6635(2) 0.15847(14) 0.46098(12) 0.0346(5) Uani 1 1 d . . . . .
H44 H 0.617995 0.179719 0.495980 0.042 Uiso 1 1 calc R U . . .
C45 C 0.8163(2) 0.14427(13) 0.47990(11) 0.0260(4) Uani 1 1 d . . . . .
C46 C 0.9031(2) 0.16090(13) 0.54892(10) 0.0254(4) Uani 1 1 d . . . . .
H46 H 0.861547 0.181898 0.585491 0.031 Uiso 1 1 calc R U . . .
C47 C 1.0527(2) 0.14621(12) 0.56374(10) 0.0232(4) Uani 1 1 d . . . . .
C48 C 1.1477(2) 0.16304(14) 0.63360(10) 0.0297(5) Uani 1 1 d . . . . .
H48 H 1.110734 0.185029 0.671451 0.036 Uiso 1 1 calc R U . . .
C49 C 1.2923(3) 0.14686(15) 0.64478(11) 0.0336(5) Uani 1 1 d . . . . .
H49 H 1.353879 0.158372 0.690342 0.040 Uiso 1 1 calc R U . . .
C50 C 1.3504(2) 0.11272(14) 0.58791(11) 0.0322(5) Uani 1 1 d . . . . .
H50 H 1.449253 0.101702 0.596708 0.039 Uiso 1 1 calc R U . . .
C51 C 1.2635(2) 0.09588(13) 0.52075(11) 0.0275(4) Uani 1 1 d . . . . .
H51 H 1.303298 0.073511 0.483994 0.033 Uiso 1 1 calc R U . . .
C52 C 1.1117(2) 0.11231(12) 0.50630(10) 0.0227(4) Uani 1 1 d . . . . .
N2 N 0.48018(18) 0.41106(10) 0.42076(8) 0.0223(3) Uani 1 1 d . . . . .
C27 C 0.2460(2) 0.41349(14) 0.33878(11) 0.0304(5) Uani 1 1 d . . . . .
H27 H 0.296503 0.437734 0.305578 0.037 Uiso 1 1 calc R U . . .
C28 C 0.0938(3) 0.39716(16) 0.32272(12) 0.0389(5) Uani 1 1 d . . . . .
H28 H 0.041158 0.410527 0.278555 0.047 Uiso 1 1 calc R U . . .
C29 C 0.0137(3) 0.35985(15) 0.37253(13) 0.0382(5) Uani 1 1 d . . . . .
H29 H -0.090588 0.348414 0.360555 0.046 Uiso 1 1 calc R U . . .
C30 C 0.0887(2) 0.34108(14) 0.43700(12) 0.0316(5) Uani 1 1 d . . . . .
H30 H 0.035230 0.317468 0.469341 0.038 Uiso 1 1 calc R U . . .
C31 C 0.2486(2) 0.35680(13) 0.45651(10) 0.0244(4) Uani 1 1 d . . . . .
C32 C 0.3311(2) 0.33894(13) 0.52234(10) 0.0253(4) Uani 1 1 d . . . . .
H32 H 0.281716 0.316303 0.556418 0.030 Uiso 1 1 calc R U . . .
C33 C 0.4875(2) 0.35472(12) 0.53763(10) 0.0223(4) Uani 1 1 d . . . . .
C34 C 0.5787(2) 0.33647(14) 0.60361(10) 0.0293(5) Uani 1 1 d . . . . .
H34 H 0.533717 0.313136 0.638937 0.035 Uiso 1 1 calc R U . . .
C35 C 0.7306(2) 0.35284(14) 0.61534(11) 0.0315(5) Uani 1 1 d . . . . .
H35 H 0.788768 0.340183 0.658457 0.038 Uiso 1 1 calc R U . . .
C36 C 0.8013(2) 0.38928(13) 0.56201(11) 0.0293(5) Uani 1 1 d . . . . .
H36 H 0.905446 0.400151 0.570719 0.035 Uiso 1 1 calc R U . . .
C37 C 0.7189(2) 0.40834(13) 0.49872(10) 0.0257(4) Uani 1 1 d . . . . .
H37 H 0.766997 0.432658 0.464696 0.031 Uiso 1 1 calc R U . . .
C38 C 0.5595(2) 0.39142(12) 0.48398(10) 0.0210(4) Uani 1 1 d . . . . .
C39 C 0.3287(2) 0.39374(13) 0.40614(10) 0.0234(4) Uani 1 1 d . . . . .
C20 C 0.4392(2) 0.83894(13) 0.06174(10) 0.0263(4) Uani 1 1 d . . . . .
H20 H 0.395732 0.815663 0.097540 0.032 Uiso 1 1 calc R U . . .
C14 C 0.5947(2) 0.86094(13) 0.07412(10) 0.0251(4) Uani 1 1 d . . . . .
C15 C 0.6928(3) 0.85036(14) 0.13999(11) 0.0329(5) Uani 1 1 d . . . . .
H15 H 0.653314 0.828299 0.177326 0.040 Uiso 1 1 calc R U . . .
C16 C 0.8440(3) 0.87223(15) 0.14890(12) 0.0372(5) Uani 1 1 d . . . . .
H16 H 0.907172 0.865628 0.192372 0.045 Uiso 1 1 calc R U . . .
C17 C 0.9055(3) 0.90497(14) 0.09224(12) 0.0352(5) Uani 1 1 d . . . . .
H17 H 1.009106 0.918499 0.098739 0.042 Uiso 1 1 calc R U . . .
C18 C 0.8162(2) 0.91702(13) 0.02857(11) 0.0300(5) Uani 1 1 d . . . . .
H18 H 0.858966 0.939215 -0.007771 0.036 Uiso 1 1 calc R U . . .
C19 C 0.6569(2) 0.89577(12) 0.01715(10) 0.0233(4) Uani 1 1 d . . . . .
N3 N 0.57066(19) 0.90952(10) -0.04613(8) 0.0238(4) Uani 1 1 d . . . . .
C21 C 0.4200(2) 0.88807(12) -0.05718(10) 0.0233(4) Uani 1 1 d . . . . .
C22 C 0.3286(2) 0.90207(13) -0.12401(10) 0.0290(5) Uani 1 1 d . . . . .
H22 H 0.372767 0.926544 -0.159229 0.035 Uiso 1 1 calc R U . . .
C23 C 0.1772(3) 0.87994(14) -0.13671(12) 0.0355(5) Uani 1 1 d . . . . .
H23 H 0.118821 0.888921 -0.180837 0.043 Uiso 1 1 calc R U . . .
C24 C 0.1063(3) 0.84330(15) -0.08377(13) 0.0377(5) Uani 1 1 d . . . . .
H24 H 0.002423 0.827899 -0.093720 0.045 Uiso 1 1 calc R U . . .
C25 C 0.1887(2) 0.83067(13) -0.01910(12) 0.0316(5) Uani 1 1 d . . . . .
H25 H 0.140946 0.808273 0.015597 0.038 Uiso 1 1 calc R U . . .
C26 C 0.3487(2) 0.85138(12) -0.00342(10) 0.0239(4) Uani 1 1 d . . . . .
C7 C 0.0092(2) 0.66044(13) 0.08920(10) 0.0264(4) Uani 1 1 d . . . . .
H7 H -0.021595 0.681285 0.129285 0.032 Uiso 1 1 calc R U . . .
C1 C 0.1535(2) 0.63897(13) 0.09619(10) 0.0255(4) Uani 1 1 d . . . . .
C2 C 0.2603(3) 0.64742(14) 0.16295(11) 0.0318(5) Uani 1 1 d . . . . .
H2 H 0.234109 0.668352 0.204270 0.038 Uiso 1 1 calc R U . . .
C3 C 0.4002(3) 0.62507(15) 0.16655(12) 0.0349(5) Uani 1 1 d . . . . .
H3 H 0.468324 0.630023 0.210332 0.042 Uiso 1 1 calc R U . . .
C4 C 0.4423(3) 0.59434(15) 0.10392(12) 0.0347(5) Uani 1 1 d . . . . .
H4 H 0.538578 0.580251 0.106995 0.042 Uiso 1 1 calc R U . . .
C5 C 0.3440(2) 0.58507(13) 0.03918(11) 0.0294(5) Uani 1 1 d . . . . .
H5 H 0.373774 0.564671 -0.001303 0.035 Uiso 1 1 calc R U . . .
C6 C 0.1963(2) 0.60636(12) 0.03313(10) 0.0236(4) Uani 1 1 d . . . . .
N4 N 0.10118(19) 0.59591(10) -0.03158(8) 0.0245(4) Uani 1 1 d . . . . .
C8 C -0.0382(2) 0.61774(13) -0.03747(10) 0.0251(4) Uani 1 1 d . . . . .
C9 C -0.1382(2) 0.60792(14) -0.10569(11) 0.0305(5) Uani 1 1 d . . . . .
H9 H -0.106934 0.586500 -0.145464 0.037 Uiso 1 1 calc R U . . .
C10 C -0.2794(3) 0.62957(14) -0.11335(12) 0.0343(5) Uani 1 1 d . . . . .
H10 H -0.343385 0.622831 -0.158347 0.041 Uiso 1 1 calc R U . . .
C11 C -0.3302(3) 0.66231(14) -0.05352(13) 0.0360(5) Uani 1 1 d . . . . .
H11 H -0.426623 0.677262 -0.059638 0.043 Uiso 1 1 calc R U . . .
C12 C -0.2386(2) 0.67184(14) 0.01249(12) 0.0312(5) Uani 1 1 d . . . . .
H12 H -0.273606 0.692196 0.051433 0.037 Uiso 1 1 calc R U . . .
C13 C -0.0892(2) 0.65104(13) 0.02297(10) 0.0250(4) Uani 1 1 d . . . . .
O1 O 0.85130(18) 0.49834(9) 0.14411(8) 0.0352(4) Uani 1 1 d . . . . .
H1 H 0.857900 0.463880 0.110121 0.053 Uiso 1 1 calc R U . . .
O2 O 0.63299(17) 0.51091(9) 0.34051(7) 0.0309(3) Uani 1 1 d . . . . .
H2A H 0.582844 0.479150 0.363210 0.046 Uiso 1 1 calc R U . . .
O5 O 0.9096(2) 0.61645(12) 0.31244(10) 0.0618(6) Uani 1 1 d . . . . .
O6 O 0.7650(2) 0.65495(10) 0.22096(9) 0.0475(4) Uani 1 1 d . . . . .
N6 N 0.80915(18) 0.59709(11) 0.25947(8) 0.0232(4) Uani 1 1 d . . . . .
C53 C 0.7414(2) 0.49862(12) 0.24225(9) 0.0194(4) Uani 1 1 d . . . . .
C54 C 0.7690(2) 0.44999(13) 0.18366(9) 0.0221(4) Uani 1 1 d . . . . .
C55 C 0.7147(2) 0.35471(13) 0.17041(10) 0.0262(4) Uani 1 1 d . . . . .
H55 H 0.732634 0.320126 0.131934 0.031 Uiso 1 1 calc R U . . .
C56 C 0.6337(2) 0.31216(13) 0.21537(10) 0.0270(4) Uani 1 1 d . . . . .
H56 H 0.598597 0.248269 0.206826 0.032 Uiso 1 1 calc R U . . .
C57 C 0.6031(2) 0.36130(13) 0.27243(10) 0.0258(4) Uani 1 1 d . . . . .
H57 H 0.546180 0.330955 0.300969 0.031 Uiso 1 1 calc R U . . .
C58 C 0.6578(2) 0.45657(13) 0.28712(9) 0.0215(4) Uani 1 1 d . . . . .
O3 O 0.14648(19) -0.00245(10) 0.35063(7) 0.0354(4) Uani 1 1 d . . . . .
H3A H 0.106887 0.030186 0.374830 0.053 Uiso 1 1 calc R U . . .
O4 O 0.32772(18) -0.00928(9) 0.14213(7) 0.0328(4) Uani 1 1 d . . . . .
H4A H 0.355296 0.024294 0.113214 0.049 Uiso 1 1 calc R U . . .
N5 N 0.26203(19) -0.09878(11) 0.25486(9) 0.0246(4) Uani 1 1 d . . . . .
C59 C 0.2409(2) -0.00080(12) 0.24754(9) 0.0200(4) Uani 1 1 d . . . . .
C60 C 0.1845(2) 0.04575(13) 0.29861(9) 0.0221(4) Uani 1 1 d . . . . .
C61 C 0.1745(2) 0.14063(13) 0.29335(10) 0.0256(4) Uani 1 1 d . . . . .
H61 H 0.138329 0.173902 0.326814 0.031 Uiso 1 1 calc R U . . .
C62 C 0.2188(2) 0.18499(13) 0.23793(10) 0.0273(4) Uani 1 1 d . . . . .
H62 H 0.213193 0.248406 0.235151 0.033 Uiso 1 1 calc R U . . .
C63 C 0.2712(2) 0.13734(13) 0.18670(10) 0.0253(4) Uani 1 1 d . . . . .
H63 H 0.298389 0.168404 0.149563 0.030 Uiso 1 1 calc R U . . .
C64 C 0.2831(2) 0.04297(13) 0.19076(9) 0.0216(4) Uani 1 1 d . . . . .
O8 O 0.1573(2) -0.15747(13) 0.25752(16) 0.0356(9) Uani 0.770(7) 1 d . . . . .
O7 O 0.3913(2) -0.11700(14) 0.26010(18) 0.0427(10) Uani 0.800(8) 1 d . . . . .
O12 O 0.1801(11) -0.1557(5) 0.2054(6) 0.047(4) Uani 0.203(8) 1 d . . . . .
O11 O 0.3353(15) -0.1184(6) 0.3042(7) 0.058(5) Uani 0.202(9) 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N1 C52 1.348(2) . ?
N1 C40 1.350(3) . ?
C40 C41 1.426(3) . ?
C40 C45 1.435(3) . ?
C41 C42 1.356(3) . ?
C41 H41 0.9300 . ?
C42 C43 1.421(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.354(3) . ?
C43 H43 0.9300 . ?
C44 C45 1.425(3) . ?
C44 H44 0.9300 . ?
C45 C46 1.387(3) . ?
C46 C47 1.398(3) . ?
C46 H46 0.9300 . ?
C47 C48 1.428(3) . ?
C47 C52 1.430(3) . ?
C48 C49 1.362(3) . ?
C48 H48 0.9300 . ?
C49 C50 1.417(3) . ?
C49 H49 0.9300 . ?
C50 C51 1.358(3) . ?
C50 H50 0.9300 . ?
C51 C52 1.425(3) . ?
C51 H51 0.9300 . ?
N2 C38 1.347(2) . ?
N2 C39 1.352(2) . ?
C27 C28 1.357(3) . ?
C27 C39 1.423(3) . ?
C27 H27 0.9300 . ?
C28 C29 1.424(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.348(3) . ?
C29 H29 0.9300 . ?
C30 C31 1.427(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.390(3) . ?
C31 C39 1.431(3) . ?
C32 C33 1.394(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.426(3) . ?
C33 C38 1.438(2) . ?
C34 C35 1.358(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.425(3) . ?
C35 H35 0.9300 . ?
C36 C37 1.356(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.423(3) . ?
C37 H37 0.9300 . ?
C20 C26 1.387(3) . ?
C20 C14 1.393(3) . ?
C20 H20 0.9300 . ?
C14 C15 1.421(3) . ?
C14 C19 1.434(3) . ?
C15 C16 1.361(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.416(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.358(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.428(3) . ?
C18 H18 0.9300 . ?
C19 N3 1.347(2) . ?
N3 C21 1.352(3) . ?
C21 C22 1.422(3) . ?
C21 C26 1.436(3) . ?
C22 C23 1.357(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.420(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.350(3) . ?
C24 H24 0.9300 . ?
C25 C26 1.429(3) . ?
C25 H25 0.9300 . ?
C7 C13 1.386(3) . ?
C7 C1 1.391(3) . ?
C7 H7 0.9300 . ?
C1 C2 1.430(3) . ?
C1 C6 1.435(3) . ?
C2 C3 1.363(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.416(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.363(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.422(3) . ?
C5 H5 0.9300 . ?
C6 N4 1.349(2) . ?
N4 C8 1.350(3) . ?
C8 C9 1.422(3) . ?
C8 C13 1.435(3) . ?
C9 C10 1.362(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.420(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.356(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.427(3) . ?
C12 H12 0.9300 . ?
O1 C54 1.350(2) . ?
O1 H1 0.8200 . ?
O2 C58 1.340(2) . ?
O2 H2A 0.8200 . ?
O5 N6 1.212(2) . ?
O6 N6 1.205(2) . ?
N6 C53 1.465(2) . ?
C53 C54 1.388(2) . ?
C53 C58 1.394(2) . ?
C54 C55 1.391(3) . ?
C55 C56 1.384(3) . ?
C55 H55 0.9300 . ?
C56 C57 1.380(3) . ?
C56 H56 0.9300 . ?
C57 C58 1.393(3) . ?
C57 H57 0.9300 . ?
O3 C60 1.337(2) . ?
O3 H3A 0.8200 . ?
O4 C64 1.341(2) . ?
O4 H4A 0.8200 . ?
N5 O11 1.118(8) . ?
N5 O8 1.210(2) . ?
N5 O7 1.242(3) . ?
N5 O12 1.262(8) . ?
N5 C59 1.467(2) . ?
C59 C60 1.394(2) . ?
C59 C64 1.398(2) . ?
C60 C61 1.396(3) . ?
C61 C62 1.387(3) . ?
C61 H61 0.9300 . ?
C62 C63 1.383(3) . ?
C62 H62 0.9300 . ?
C63 C64 1.390(3) . ?
C63 H63 0.9300 . ?
O8 O12 1.074(12) . ?
O8 O11 1.698(11) . ?
O7 O11 1.090(15) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C52 N1 C40 119.35(16) . . ?
N1 C40 C41 119.31(18) . . ?
N1 C40 C45 122.12(18) . . ?
C41 C40 C45 118.57(19) . . ?
C42 C41 C40 120.6(2) . . ?
C42 C41 H41 119.7 . . ?
C40 C41 H41 119.7 . . ?
C41 C42 C43 120.9(2) . . ?
C41 C42 H42 119.6 . . ?
C43 C42 H42 119.6 . . ?
C44 C43 C42 120.4(2) . . ?
C44 C43 H43 119.8 . . ?
C42 C43 H43 119.8 . . ?
C43 C44 C45 120.8(2) . . ?
C43 C44 H44 119.6 . . ?
C45 C44 H44 119.6 . . ?
C46 C45 C44 123.18(19) . . ?
C46 C45 C40 118.07(18) . . ?
C44 C45 C40 118.75(19) . . ?
C45 C46 C47 120.26(18) . . ?
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C46 C47 C48 122.68(18) . . ?
C46 C47 C52 118.21(18) . . ?
C48 C47 C52 119.10(18) . . ?
C49 C48 C47 119.96(19) . . ?
C49 C48 H48 120.0 . . ?
C47 C48 H48 120.0 . . ?
C48 C49 C50 120.9(2) . . ?
C48 C49 H49 119.6 . . ?
C50 C49 H49 119.6 . . ?
C51 C50 C49 120.9(2) . . ?
C51 C50 H50 119.6 . . ?
C49 C50 H50 119.6 . . ?
C50 C51 C52 120.32(19) . . ?
C50 C51 H51 119.8 . . ?
C52 C51 H51 119.8 . . ?
N1 C52 C51 119.18(17) . . ?
N1 C52 C47 121.96(18) . . ?
C51 C52 C47 118.86(18) . . ?
C38 N2 C39 119.52(16) . . ?
C28 C27 C39 120.4(2) . . ?
C28 C27 H27 119.8 . . ?
C39 C27 H27 119.8 . . ?
C27 C28 C29 120.9(2) . . ?
C27 C28 H28 119.5 . . ?
C29 C28 H28 119.5 . . ?
C30 C29 C28 120.1(2) . . ?
C30 C29 H29 119.9 . . ?
C28 C29 H29 119.9 . . ?
C29 C30 C31 121.2(2) . . ?
C29 C30 H30 119.4 . . ?
C31 C30 H30 119.4 . . ?
C32 C31 C30 123.40(18) . . ?
C32 C31 C39 118.10(18) . . ?
C30 C31 C39 118.50(18) . . ?
C31 C32 C33 120.47(17) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C34 123.30(17) . . ?
C32 C33 C38 118.00(17) . . ?
C34 C33 C38 118.70(18) . . ?
C35 C34 C33 120.65(18) . . ?
C35 C34 H34 119.7 . . ?
C33 C34 H34 119.7 . . ?
C34 C35 C36 120.41(19) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 120.92(19) . . ?
C37 C36 H36 119.5 . . ?
C35 C36 H36 119.5 . . ?
C36 C37 C38 120.50(18) . . ?
C36 C37 H37 119.8 . . ?
C38 C37 H37 119.8 . . ?
N2 C38 C37 119.35(16) . . ?
N2 C38 C33 121.82(17) . . ?
C37 C38 C33 118.82(17) . . ?
N2 C39 C27 119.09(17) . . ?
N2 C39 C31 122.06(17) . . ?
C27 C39 C31 118.85(18) . . ?
C26 C20 C14 120.69(17) . . ?
C26 C20 H20 119.7 . . ?
C14 C20 H20 119.7 . . ?
C20 C14 C15 123.11(18) . . ?
C20 C14 C19 117.72(18) . . ?
C15 C14 C19 119.17(19) . . ?
C16 C15 C14 120.58(19) . . ?
C16 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C15 C16 C17 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C18 C17 C16 121.3(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.32(19) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
N3 C19 C18 119.18(17) . . ?
N3 C19 C14 122.43(18) . . ?
C18 C19 C14 118.40(18) . . ?
C19 N3 C21 119.08(16) . . ?
N3 C21 C22 119.29(17) . . ?
N3 C21 C26 122.07(17) . . ?
C22 C21 C26 118.64(18) . . ?
C23 C22 C21 120.39(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C24 121.1(2) . . ?
C22 C23 H23 119.4 . . ?
C24 C23 H23 119.4 . . ?
C25 C24 C23 120.4(2) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 120.67(19) . . ?
C24 C25 H25 119.7 . . ?
C26 C25 H25 119.7 . . ?
C20 C26 C25 123.25(18) . . ?
C20 C26 C21 118.00(18) . . ?
C25 C26 C21 118.74(18) . . ?
C13 C7 C1 120.53(17) . . ?
C13 C7 H7 119.7 . . ?
C1 C7 H7 119.7 . . ?
C7 C1 C2 123.21(18) . . ?
C7 C1 C6 118.02(18) . . ?
C2 C1 C6 118.77(18) . . ?
C3 C2 C1 120.58(19) . . ?
C3 C2 H2 119.7 . . ?
C1 C2 H2 119.7 . . ?
C2 C3 C4 120.3(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C5 C4 C3 121.1(2) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.47(18) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
N4 C6 C5 119.12(17) . . ?
N4 C6 C1 122.11(18) . . ?
C5 C6 C1 118.78(18) . . ?
C6 N4 C8 119.08(16) . . ?
N4 C8 C9 119.31(17) . . ?
N4 C8 C13 122.16(18) . . ?
C9 C8 C13 118.53(18) . . ?
C10 C9 C8 120.66(19) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 H10 119.6 . . ?
C12 C11 C10 120.3(2) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 120.84(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C7 C13 C12 123.07(18) . . ?
C7 C13 C8 118.09(18) . . ?
C12 C13 C8 118.83(19) . . ?
C54 O1 H1 109.5 . . ?
C58 O2 H2A 109.5 . . ?
O6 N6 O5 122.75(17) . . ?
O6 N6 C53 119.65(16) . . ?
O5 N6 C53 117.60(16) . . ?
C54 C53 C58 122.76(16) . . ?
C54 C53 N6 118.42(15) . . ?
C58 C53 N6 118.75(15) . . ?
O1 C54 C53 117.34(16) . . ?
O1 C54 C55 124.06(17) . . ?
C53 C54 C55 118.57(16) . . ?
C56 C55 C54 118.99(17) . . ?
C56 C55 H55 120.5 . . ?
C54 C55 H55 120.5 . . ?
C57 C56 C55 122.22(18) . . ?
C57 C56 H56 118.9 . . ?
C55 C56 H56 118.9 . . ?
C56 C57 C58 119.72(17) . . ?
C56 C57 H57 120.1 . . ?
C58 C57 H57 120.1 . . ?
O2 C58 C57 124.49(16) . . ?
O2 C58 C53 117.79(16) . . ?
C57 C58 C53 117.71(16) . . ?
C60 O3 H3A 109.5 . . ?
C64 O4 H4A 109.5 . . ?
O11 N5 O8 93.5(8) . . ?
O11 N5 O7 54.7(8) . . ?
O8 N5 O7 122.64(19) . . ?
O11 N5 O12 125.3(6) . . ?
O8 N5 O12 51.5(5) . . ?
O7 N5 O12 105.6(5) . . ?
O11 N5 C59 120.2(5) . . ?
O8 N5 C59 120.36(17) . . ?
O7 N5 C59 116.97(17) . . ?
O12 N5 C59 114.1(4) . . ?
C60 C59 C64 122.66(16) . . ?
C60 C59 N5 118.86(15) . . ?
C64 C59 N5 118.44(16) . . ?
O3 C60 C59 118.15(16) . . ?
O3 C60 C61 123.83(16) . . ?
C59 C60 C61 118.01(16) . . ?
C62 C61 C60 119.63(17) . . ?
C62 C61 H61 120.2 . . ?
C60 C61 H61 120.2 . . ?
C63 C62 C61 121.70(18) . . ?
C63 C62 H62 119.2 . . ?
C61 C62 H62 119.2 . . ?
C62 C63 C64 119.94(17) . . ?
C62 C63 H63 120.0 . . ?
C64 C63 H63 120.0 . . ?
O4 C64 C63 123.84(16) . . ?
O4 C64 C59 118.09(16) . . ?
C63 C64 C59 118.03(16) . . ?
O12 O8 N5 66.7(4) . . ?
O12 O8 O11 96.9(7) . . ?
N5 O8 O11 41.1(4) . . ?
O11 O7 N5 56.8(4) . . ?
O8 O12 N5 61.8(6) . . ?
O7 O11 N5 68.5(8) . . ?
O7 O11 O8 98.7(7) . . ?
N5 O11 O8 45.4(4) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C52 N1 C40 C41 179.26(16) . . . . ?
C52 N1 C40 C45 -1.5(3) . . . . ?
N1 C40 C41 C42 179.34(18) . . . . ?
C45 C40 C41 C42 0.1(3) . . . . ?
C40 C41 C42 C43 0.1(3) . . . . ?
C41 C42 C43 C44 -0.4(3) . . . . ?
C42 C43 C44 C45 0.6(3) . . . . ?
C43 C44 C45 C46 179.82(19) . . . . ?
C43 C44 C45 C40 -0.4(3) . . . . ?
N1 C40 C45 C46 0.6(3) . . . . ?
C41 C40 C45 C46 179.86(17) . . . . ?
N1 C40 C45 C44 -179.19(17) . . . . ?
C41 C40 C45 C44 0.0(3) . . . . ?
C44 C45 C46 C47 -179.50(17) . . . . ?
C40 C45 C46 C47 0.7(3) . . . . ?
C45 C46 C47 C48 179.36(17) . . . . ?
C45 C46 C47 C52 -1.1(3) . . . . ?
C46 C47 C48 C49 179.60(18) . . . . ?
C52 C47 C48 C49 0.1(3) . . . . ?
C47 C48 C49 C50 -0.5(3) . . . . ?
C48 C49 C50 C51 0.5(3) . . . . ?
C49 C50 C51 C52 0.0(3) . . . . ?
C40 N1 C52 C51 -179.49(16) . . . . ?
C40 N1 C52 C47 1.1(3) . . . . ?
C50 C51 C52 N1 -179.79(17) . . . . ?
C50 C51 C52 C47 -0.4(3) . . . . ?
C46 C47 C52 N1 0.2(3) . . . . ?
C48 C47 C52 N1 179.77(16) . . . . ?
C46 C47 C52 C51 -179.22(16) . . . . ?
C48 C47 C52 C51 0.3(3) . . . . ?
C39 C27 C28 C29 -0.2(3) . . . . ?
C27 C28 C29 C30 0.7(3) . . . . ?
C28 C29 C30 C31 -0.8(3) . . . . ?
C29 C30 C31 C32 179.75(19) . . . . ?
C29 C30 C31 C39 0.4(3) . . . . ?
C30 C31 C32 C33 179.15(17) . . . . ?
C39 C31 C32 C33 -1.5(3) . . . . ?
C31 C32 C33 C34 -178.97(17) . . . . ?
C31 C32 C33 C38 1.2(3) . . . . ?
C32 C33 C34 C35 179.69(18) . . . . ?
C38 C33 C34 C35 -0.4(3) . . . . ?
C33 C34 C35 C36 0.5(3) . . . . ?
C34 C35 C36 C37 0.0(3) . . . . ?
C35 C36 C37 C38 -0.6(3) . . . . ?
C39 N2 C38 C37 178.99(16) . . . . ?
C39 N2 C38 C33 -1.8(3) . . . . ?
C36 C37 C38 N2 179.91(17) . . . . ?
C36 C37 C38 C33 0.6(3) . . . . ?
C32 C33 C38 N2 0.5(3) . . . . ?
C34 C33 C38 N2 -179.37(16) . . . . ?
C32 C33 C38 C37 179.75(16) . . . . ?
C34 C33 C38 C37 -0.1(3) . . . . ?
C38 N2 C39 C27 -179.11(16) . . . . ?
C38 N2 C39 C31 1.4(3) . . . . ?
C28 C27 C39 N2 -179.74(18) . . . . ?
C28 C27 C39 C31 -0.2(3) . . . . ?
C32 C31 C39 N2 0.2(3) . . . . ?
C30 C31 C39 N2 179.61(17) . . . . ?
C32 C31 C39 C27 -179.26(17) . . . . ?
C30 C31 C39 C27 0.1(3) . . . . ?
C26 C20 C14 C15 179.46(17) . . . . ?
C26 C20 C14 C19 -0.6(3) . . . . ?
C20 C14 C15 C16 179.43(19) . . . . ?
C19 C14 C15 C16 -0.5(3) . . . . ?
C14 C15 C16 C17 -0.6(3) . . . . ?
C15 C16 C17 C18 1.2(3) . . . . ?
C16 C17 C18 C19 -0.6(3) . . . . ?
C17 C18 C19 N3 179.11(17) . . . . ?
C17 C18 C19 C14 -0.5(3) . . . . ?
C20 C14 C19 N3 1.5(3) . . . . ?
C15 C14 C19 N3 -178.52(17) . . . . ?
C20 C14 C19 C18 -178.86(17) . . . . ?
C15 C14 C19 C18 1.1(3) . . . . ?
C18 C19 N3 C21 179.04(16) . . . . ?
C14 C19 N3 C21 -1.4(3) . . . . ?
C19 N3 C21 C22 -179.72(16) . . . . ?
C19 N3 C21 C26 0.3(3) . . . . ?
N3 C21 C22 C23 179.15(17) . . . . ?
C26 C21 C22 C23 -0.8(3) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C22 C23 C24 C25 0.7(3) . . . . ?
C23 C24 C25 C26 -1.8(3) . . . . ?
C14 C20 C26 C25 -179.57(17) . . . . ?
C14 C20 C26 C21 -0.4(3) . . . . ?
C24 C25 C26 C20 -179.34(18) . . . . ?
C24 C25 C26 C21 1.5(3) . . . . ?
N3 C21 C26 C20 0.6(3) . . . . ?
C22 C21 C26 C20 -179.39(16) . . . . ?
N3 C21 C26 C25 179.82(16) . . . . ?
C22 C21 C26 C25 -0.2(3) . . . . ?
C13 C7 C1 C2 179.84(17) . . . . ?
C13 C7 C1 C6 -0.5(3) . . . . ?
C7 C1 C2 C3 179.82(19) . . . . ?
C6 C1 C2 C3 0.1(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C2 C3 C4 C5 -1.0(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 N4 -179.56(17) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C7 C1 C6 N4 -0.3(3) . . . . ?
C2 C1 C6 N4 179.46(17) . . . . ?
C7 C1 C6 C5 179.31(17) . . . . ?
C2 C1 C6 C5 -1.0(3) . . . . ?
C5 C6 N4 C8 -178.82(16) . . . . ?
C1 C6 N4 C8 0.7(3) . . . . ?
C6 N4 C8 C9 179.25(16) . . . . ?
C6 N4 C8 C13 -0.5(3) . . . . ?
N4 C8 C9 C10 -179.87(17) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
C8 C9 C10 C11 -0.1(3) . . . . ?
C9 C10 C11 C12 -0.5(3) . . . . ?
C10 C11 C12 C13 1.2(3) . . . . ?
C1 C7 C13 C12 179.90(17) . . . . ?
C1 C7 C13 C8 0.7(3) . . . . ?
C11 C12 C13 C7 179.40(18) . . . . ?
C11 C12 C13 C8 -1.4(3) . . . . ?
N4 C8 C13 C7 -0.2(3) . . . . ?
C9 C8 C13 C7 -179.95(17) . . . . ?
N4 C8 C13 C12 -179.44(16) . . . . ?
C9 C8 C13 C12 0.8(3) . . . . ?
O6 N6 C53 C54 69.9(2) . . . . ?
O5 N6 C53 C54 -109.5(2) . . . . ?
O6 N6 C53 C58 -113.0(2) . . . . ?
O5 N6 C53 C58 67.6(2) . . . . ?
C58 C53 C54 O1 179.89(17) . . . . ?
N6 C53 C54 O1 -3.1(3) . . . . ?
C58 C53 C54 C55 -2.0(3) . . . . ?
N6 C53 C54 C55 175.02(17) . . . . ?
O1 C54 C55 C56 178.88(19) . . . . ?
C53 C54 C55 C56 0.9(3) . . . . ?
C54 C55 C56 C57 0.9(3) . . . . ?
C55 C56 C57 C58 -1.6(3) . . . . ?
C56 C57 C58 O2 179.09(19) . . . . ?
C56 C57 C58 C53 0.5(3) . . . . ?
C54 C53 C58 O2 -177.42(17) . . . . ?
N6 C53 C58 O2 5.6(3) . . . . ?
C54 C53 C58 C57 1.3(3) . . . . ?
N6 C53 C58 C57 -175.71(17) . . . . ?
O11 N5 C59 C60 -57.5(11) . . . . ?
O8 N5 C59 C60 57.6(3) . . . . ?
O7 N5 C59 C60 -120.4(2) . . . . ?
O12 N5 C59 C60 115.7(7) . . . . ?
O11 N5 C59 C64 120.4(10) . . . . ?
O8 N5 C59 C64 -124.5(2) . . . . ?
O7 N5 C59 C64 57.5(3) . . . . ?
O12 N5 C59 C64 -66.4(7) . . . . ?
C64 C59 C60 O3 179.56(18) . . . . ?
N5 C59 C60 O3 -2.6(3) . . . . ?
C64 C59 C60 C61 -1.9(3) . . . . ?
N5 C59 C60 C61 175.88(17) . . . . ?
O3 C60 C61 C62 179.04(19) . . . . ?
C59 C60 C61 C62 0.6(3) . . . . ?
C60 C61 C62 C63 0.9(3) . . . . ?
C61 C62 C63 C64 -1.2(3) . . . . ?
C62 C63 C64 O4 177.61(19) . . . . ?
C62 C63 C64 C59 0.0(3) . . . . ?
C60 C59 C64 O4 -176.14(17) . . . . ?
N5 C59 C64 O4 6.0(3) . . . . ?
C60 C59 C64 C63 1.7(3) . . . . ?
N5 C59 C64 C63 -176.18(17) . . . . ?
O11 N5 O8 O12 -133.7(8) . . . . ?
O7 N5 O8 O12 -84.1(6) . . . . ?
C59 N5 O8 O12 98.0(5) . . . . ?
O7 N5 O8 O11 49.6(6) . . . . ?
O12 N5 O8 O11 133.7(8) . . . . ?
C59 N5 O8 O11 -128.3(7) . . . . ?
O8 N5 O7 O11 -68.7(7) . . . . ?
O12 N5 O7 O11 -122.6(8) . . . . ?
C59 N5 O7 O11 109.3(6) . . . . ?
O11 O8 O12 N5 -28.6(4) . . . . ?
O11 N5 O12 O8 62.1(13) . . . . ?
O7 N5 O12 O8 119.6(4) . . . . ?
C59 N5 O12 O8 -110.6(4) . . . . ?
N5 O7 O11 O8 34.4(2) . . . . ?
O8 N5 O11 O7 128.2(4) . . . . ?
O12 N5 O11 O7 84.3(11) . . . . ?
C59 N5 O11 O7 -103.3(5) . . . . ?
O7 N5 O11 O8 -128.2(4) . . . . ?
O12 N5 O11 O8 -43.9(9) . . . . ?
C59 N5 O11 O8 128.5(6) . . . . ?
O12 O8 O11 O7 -5.7(7) . . . . ?
N5 O8 O11 O7 -47.7(6) . . . . ?
O12 O8 O11 N5 42.0(7) . . . . ?
 
_refine_diff_density_max    0.576
_refine_diff_density_min   -0.400
_refine_diff_density_rms    0.054


 
data_4NRES-DMP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H13 N3 O4' 
_chemical_formula_weight          263.25

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    8.7482(14)
_cell_length_b                    14.926(3)
_cell_length_c                    10.2464(17)
_cell_angle_alpha                 90
_cell_angle_beta                  110.165(8)
_cell_angle_gamma                 90
_cell_volume                      1255.9(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     4346
_cell_measurement_theta_min       3.5
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Brown'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.392          
_exptl_crystal_F_000              552
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.260
_exptl_crystal_size_mid           0.210
_exptl_crystal_size_min           0.170
_exptl_absorpt_coefficient_mu     0.107
_shelx_estimated_absorpt_T_min    0.973
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.793
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             6402
_diffrn_reflns_av_unetI/netI      0.0592
_diffrn_reflns_av_R_equivalents   0.0646
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -19
_diffrn_reflns_limit_k_max        19
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.455
_diffrn_reflns_theta_max          27.484
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              1441
_reflns_number_gt                 859
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1096P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.019(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          1441
_refine_ls_number_parameters      90
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0924
_refine_ls_R_factor_gt            0.0566
_refine_ls_wR_factor_ref          0.1989
_refine_ls_wR_factor_gt           0.1620
_refine_ls_goodness_of_fit_ref    1.020
_refine_ls_restrained_S_all       1.020
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N1 N 0.000000 0.44224(18) 0.250000 0.0487(8) Uani 1 2 d S T P . .
O1 O 0.28383(18) 0.35093(11) 0.34731(19) 0.0559(6) Uani 1 1 d . . . . .
H1 H 0.364390 0.318473 0.371599 0.084 Uiso 1 1 calc R U . . .
C6 C 0.7062(3) 0.33684(14) 0.4823(2) 0.0418(6) Uani 1 1 d . . . . .
C3 C 0.1487(3) 0.30020(15) 0.3006(2) 0.0415(6) Uani 1 1 d . . . . .
N2 N 0.5878(2) 0.27505(13) 0.43909(18) 0.0440(6) Uani 1 1 d . . . . .
C1 C 0.000000 0.1629(2) 0.250000 0.0554(9) Uani 1 2 d S T P . .
H1A H 0.000000 0.100585 0.250000 0.066 Uiso 1 2 calc R U P . .
C7 C 0.8662(3) 0.31027(14) 0.5418(2) 0.0452(6) Uani 1 1 d . . . . .
H7 H 0.946105 0.354302 0.570073 0.054 Uiso 1 1 calc R U . . .
C4 C 0.000000 0.34430(19) 0.250000 0.0385(7) Uani 1 2 d S T P . .
C2 C 0.1472(3) 0.20758(16) 0.3021(2) 0.0509(7) Uani 1 1 d . . . . .
H2 H 0.244026 0.175666 0.337774 0.061 Uiso 1 1 calc R U . . .
O2 O 0.0475(3) 0.48063(13) 0.1684(2) 0.0884(8) Uani 1 1 d . . . . .
C8 C 0.6575(3) 0.43299(15) 0.4621(3) 0.0655(8) Uani 1 1 d . . . . .
H8A H 0.752696 0.470049 0.497064 0.098 Uiso 1 1 calc R U . . .
H8B H 0.603902 0.444697 0.364819 0.098 Uiso 1 1 calc R U . . .
H8C H 0.584685 0.446146 0.511369 0.098 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N1 O2 1.200(2) 2 ?
N1 O2 1.200(2) . ?
N1 C4 1.462(4) . ?
O1 C3 1.345(3) . ?
C6 N2 1.343(3) . ?
C6 C7 1.378(3) . ?
C6 C8 1.491(3) . ?
C3 C2 1.383(3) . ?
C3 C4 1.389(3) . ?
N2 C7 1.330(3) 7_656 ?
C1 C2 1.383(3) . ?
C1 C2 1.383(3) 2 ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 N1 O2 123.0(3) 2 . ?
O2 N1 C4 118.52(16) 2 . ?
O2 N1 C4 118.52(16) . . ?
N2 C6 C7 119.9(2) . . ?
N2 C6 C8 117.7(2) . . ?
C7 C6 C8 122.4(2) . . ?
O1 C3 C2 124.7(2) . . ?
O1 C3 C4 117.5(2) . . ?
C2 C3 C4 117.8(2) . . ?
C7 N2 C6 116.69(19) 7_656 . ?
C2 C1 C2 122.3(3) . 2 ?
N2 C7 C6 123.4(2) 7_656 . ?
C3 C4 C3 123.4(3) . 2 ?
C3 C4 N1 118.29(14) . . ?
C3 C4 N1 118.29(14) 2 . ?
C3 C2 C1 119.3(2) . . ?
 
_refine_diff_density_max    0.337
_refine_diff_density_min   -0.217
_refine_diff_density_rms    0.063


 
data_5NRES-9AACR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C19 H15 N3 O4' 
_chemical_formula_weight          349.34

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.7638(14)
_cell_length_b                    8.5897(15)
_cell_length_c                    12.723(2)
_cell_angle_alpha                 105.585(7)
_cell_angle_beta                  102.978(7)
_cell_angle_gamma                 95.062(7)
_cell_volume                      786.3(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     5658
_cell_measurement_theta_min       3.4
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.475          
_exptl_crystal_F_000              364
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.106
_shelx_estimated_absorpt_T_min    0.979
_shelx_estimated_absorpt_T_max    0.979
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.744
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication' 
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube' 
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             7168
_diffrn_reflns_av_unetI/netI      0.0562
_diffrn_reflns_av_R_equivalents   0.0391
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.392
_diffrn_reflns_theta_max          27.483
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.982
_diffrn_measured_fraction_theta_full  0.988
_diffrn_reflns_Laue_measured_fraction_max    0.982
_diffrn_reflns_Laue_measured_fraction_full   0.988
_diffrn_reflns_point_group_measured_fraction_max   0.982
_diffrn_reflns_point_group_measured_fraction_full  0.988
_reflns_number_total              3538
_reflns_number_gt                 2234
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0982P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3538
_refine_ls_number_parameters      236
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0890
_refine_ls_R_factor_gt            0.0530
_refine_ls_wR_factor_ref          0.1769
_refine_ls_wR_factor_gt           0.1414
_refine_ls_goodness_of_fit_ref    1.035
_refine_ls_restrained_S_all       1.035
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.5554(2) 0.10015(18) 0.27152(12) 0.0271(4) Uani 1 1 d . . . . .
O2 O 0.7822(2) -0.22913(19) -0.02638(13) 0.0326(4) Uani 1 1 d . . . . .
H2 H 0.872474 -0.160678 0.005270 0.049 Uiso 1 1 calc R U . . .
O3 O 0.9559(2) 0.0378(2) 0.10529(14) 0.0427(5) Uani 1 1 d . . . . .
N1 N 0.2317(2) 0.6350(2) 0.55075(14) 0.0228(4) Uani 1 1 d . . . . .
H1 H 0.236536 0.715373 0.609291 0.027 Uiso 1 1 calc R U . . .
N3 N 0.8378(2) 0.0623(2) 0.15944(15) 0.0265(4) Uani 1 1 d . . . . .
O4 O 0.8673(2) 0.1826(2) 0.24322(15) 0.0479(6) Uani 1 1 d . . . . .
N2 N 0.2836(2) 0.2822(2) 0.27473(14) 0.0261(5) Uani 1 1 d . . . . .
H2A H 0.334962 0.200456 0.284268 0.031 Uiso 1 1 calc R U . . .
H2B H 0.254118 0.295055 0.208644 0.031 Uiso 1 1 calc R U . . .
C13 C 0.2875(3) 0.4950(2) 0.56593(17) 0.0209(5) Uani 1 1 d . . . . .
C19 C 0.2503(3) 0.3873(3) 0.36111(17) 0.0209(5) Uani 1 1 d . . . . .
C18 C 0.2996(3) 0.3662(2) 0.47215(17) 0.0198(5) Uani 1 1 d . . . . .
C12 C 0.1689(3) 0.6527(3) 0.44704(17) 0.0218(5) Uani 1 1 d . . . . .
C1 C 0.6759(3) -0.0486(2) 0.12276(16) 0.0208(5) Uani 1 1 d . . . . .
C7 C 0.1683(3) 0.5280(3) 0.34856(17) 0.0210(5) Uani 1 1 d . . . . .
C2 C 0.5357(3) -0.0162(2) 0.17994(17) 0.0215(5) Uani 1 1 d . . . . .
C6 C 0.6514(3) -0.1911(3) 0.02691(17) 0.0235(5) Uani 1 1 d . . . . .
C17 C 0.3608(3) 0.2233(3) 0.49234(18) 0.0247(5) Uani 1 1 d . . . . .
H17 H 0.369752 0.137689 0.431992 0.030 Uiso 1 1 calc R U . . .
C9 C 0.0338(3) 0.6917(3) 0.2342(2) 0.0302(5) Uani 1 1 d . . . . .
H9 H -0.014418 0.704275 0.163654 0.036 Uiso 1 1 calc R U . . .
C14 C 0.3363(3) 0.4786(3) 0.67554(18) 0.0255(5) Uani 1 1 d . . . . .
H14 H 0.328380 0.562768 0.737099 0.031 Uiso 1 1 calc R U . . .
C15 C 0.3951(3) 0.3398(3) 0.69155(19) 0.0291(5) Uani 1 1 d . . . . .
H15 H 0.427984 0.330593 0.764300 0.035 Uiso 1 1 calc R U . . .
C5 C 0.4916(3) -0.2950(3) -0.01254(18) 0.0317(6) Uani 1 1 d . . . . .
H5 H 0.476196 -0.389643 -0.072457 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3512(3) -0.2580(3) 0.03798(19) 0.0330(6) Uani 1 1 d . . . . .
H4 H 0.241568 -0.326953 0.008483 0.040 Uiso 1 1 calc R U . . .
C11 C 0.1083(3) 0.7995(3) 0.43761(19) 0.0287(5) Uani 1 1 d . . . . .
H11 H 0.113244 0.883952 0.502319 0.034 Uiso 1 1 calc R U . . .
C8 C 0.0968(3) 0.5510(3) 0.24207(18) 0.0267(5) Uani 1 1 d . . . . .
H8 H 0.092856 0.468709 0.176472 0.032 Uiso 1 1 calc R U . . .
C16 C 0.4067(3) 0.2101(3) 0.59960(19) 0.0275(5) Uani 1 1 d . . . . .
H16 H 0.445591 0.115463 0.611738 0.033 Uiso 1 1 calc R U . . .
C3 C 0.3702(3) -0.1246(3) 0.12860(19) 0.0297(5) Uani 1 1 d . . . . .
H3 H 0.272379 -0.103574 0.157948 0.036 Uiso 1 1 calc R U . . .
C10 C 0.0420(3) 0.8178(3) 0.3331(2) 0.0319(6) Uani 1 1 d . . . . .
H10 H 0.001879 0.914882 0.327386 0.038 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C2 1.283(2) . ?
O2 C6 1.359(3) . ?
O2 H2 0.8200 . ?
O3 N3 1.264(2) . ?
N1 C12 1.354(3) . ?
N1 C13 1.360(3) . ?
N1 H1 0.8600 . ?
N3 O4 1.230(2) . ?
N3 C1 1.411(3) . ?
N2 C19 1.314(2) . ?
N2 H2A 0.8600 . ?
N2 H2B 0.8600 . ?
C13 C14 1.409(3) . ?
C13 C18 1.420(3) . ?
C19 C18 1.443(3) . ?
C19 C7 1.444(3) . ?
C18 C17 1.420(3) . ?
C12 C7 1.411(3) . ?
C12 C11 1.410(3) . ?
C1 C6 1.440(3) . ?
C1 C2 1.446(3) . ?
C7 C8 1.417(3) . ?
C2 C3 1.425(3) . ?
C6 C5 1.368(3) . ?
C17 C16 1.369(3) . ?
C17 H17 0.9300 . ?
C9 C8 1.363(3) . ?
C9 C10 1.408(3) . ?
C9 H9 0.9300 . ?
C14 C15 1.362(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.408(3) . ?
C15 H15 0.9300 . ?
C5 C4 1.403(3) . ?
C5 H5 0.9300 . ?
C4 C3 1.359(3) . ?
C4 H4 0.9300 . ?
C11 C10 1.370(3) . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C16 H16 0.9300 . ?
C3 H3 0.9300 . ?
C10 H10 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 O2 H2 109.5 . . ?
C12 N1 C13 122.56(17) . . ?
C12 N1 H1 118.7 . . ?
C13 N1 H1 118.7 . . ?
O4 N3 O3 118.99(18) . . ?
O4 N3 C1 121.52(18) . . ?
O3 N3 C1 119.48(17) . . ?
C19 N2 H2A 120.0 . . ?
C19 N2 H2B 120.0 . . ?
H2A N2 H2B 120.0 . . ?
N1 C13 C14 119.86(18) . . ?
N1 C13 C18 120.37(19) . . ?
C14 C13 C18 119.8(2) . . ?
N2 C19 C18 120.2(2) . . ?
N2 C19 C7 121.42(19) . . ?
C18 C19 C7 118.35(18) . . ?
C13 C18 C17 118.3(2) . . ?
C13 C18 C19 118.46(19) . . ?
C17 C18 C19 123.19(19) . . ?
N1 C12 C7 120.83(19) . . ?
N1 C12 C11 119.48(18) . . ?
C7 C12 C11 119.7(2) . . ?
N3 C1 C6 119.22(18) . . ?
N3 C1 C2 119.85(17) . . ?
C6 C1 C2 120.92(18) . . ?
C12 C7 C8 118.5(2) . . ?
C12 C7 C19 118.39(19) . . ?
C8 C7 C19 122.96(19) . . ?
O1 C2 C3 120.8(2) . . ?
O1 C2 C1 123.67(19) . . ?
C3 C2 C1 115.49(19) . . ?
O2 C6 C5 117.70(19) . . ?
O2 C6 C1 122.68(19) . . ?
C5 C6 C1 119.6(2) . . ?
C16 C17 C18 120.8(2) . . ?
C16 C17 H17 119.6 . . ?
C18 C17 H17 119.6 . . ?
C8 C9 C10 119.8(2) . . ?
C8 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C15 C14 C13 120.2(2) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 121.0(2) . . ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
C6 C5 C4 119.6(2) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C3 C4 C5 122.2(2) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C9 C8 C7 121.1(2) . . ?
C9 C8 H8 119.4 . . ?
C7 C8 H8 119.4 . . ?
C17 C16 C15 119.9(2) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C4 C3 C2 121.9(2) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C11 C10 C9 120.9(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
 
_refine_diff_density_max    0.308
_refine_diff_density_min   -0.357
_refine_diff_density_rms    0.085


 
data_6NRES-33BP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C26 H21 N5 O4' 
_chemical_formula_weight          467.48

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.3217(8)
_cell_length_b                    11.6513(13)
_cell_length_c                    13.9987(16)
_cell_angle_alpha                 105.915(7)
_cell_angle_beta                  102.665(7)
_cell_angle_gamma                 91.242(6)
_cell_volume                      1116.2(2)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     10398
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.391          
_exptl_crystal_F_000              488
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.097
_shelx_estimated_absorpt_T_min    0.981
_shelx_estimated_absorpt_T_max    0.981
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.888
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             11717
_diffrn_reflns_av_unetI/netI      0.0327
_diffrn_reflns_av_R_equivalents   0.0232
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.113
_diffrn_reflns_theta_max          27.482
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              5120
_reflns_number_gt                 4075
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0504P)²+0.2648P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5120
_refine_ls_number_parameters      318
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0519
_refine_ls_R_factor_gt            0.0397
_refine_ls_wR_factor_ref          0.1041
_refine_ls_wR_factor_gt           0.0945
_refine_ls_goodness_of_fit_ref    1.045
_refine_ls_restrained_S_all       1.045
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O2 O 0.62535(13) -0.01397(8) 0.37342(7) 0.0223(2) Uani 1 1 d . . . . .
H2 H 0.641170 0.054860 0.370726 0.033 Uiso 1 1 calc R U . . .
O1 O 0.93638(13) -0.34882(8) 0.41651(7) 0.0224(2) Uani 1 1 d . . . . .
H1 H 1.020157 -0.388530 0.398165 0.034 Uiso 1 1 calc R U . . .
O4 O 0.51596(14) -0.30008(10) 0.32253(8) 0.0337(3) Uani 1 1 d . . . . .
O3 O 0.58962(15) -0.22002(11) 0.48531(8) 0.0372(3) Uani 1 1 d . . . . .
N2 N 0.65425(16) 0.19231(10) 0.32435(9) 0.0227(3) Uani 1 1 d . . . . .
N1 N 0.62009(15) -0.23644(10) 0.40083(8) 0.0187(2) Uani 1 1 d . . . . .
N3 N 0.77484(17) 0.01404(11) -0.07001(9) 0.0284(3) Uani 1 1 d . . . . .
N4 N 0.15102(16) 0.48877(10) 0.33818(8) 0.0217(2) Uani 1 1 d . . . . .
C7 C 0.65747(19) 0.31084(12) 0.36573(10) 0.0224(3) Uani 1 1 d . . . . .
H7 H 0.652692 0.339692 0.433927 0.027 Uiso 1 1 calc R U . . .
N5 N 0.26793(17) 0.47096(11) -0.05175(9) 0.0262(3) Uani 1 1 d . . . . .
C2 C 0.95337(18) -0.24026(11) 0.40054(9) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.95771(19) -0.01179(12) 0.37179(9) 0.0198(3) Uani 1 1 d . . . . .
H5 H 0.961842 0.063836 0.361827 0.024 Uiso 1 1 calc R U . . .
C8 C 0.66768(19) 0.39178(12) 0.31041(10) 0.0225(3) Uani 1 1 d . . . . .
H8 H 0.668643 0.473514 0.340960 0.027 Uiso 1 1 calc R U . . .
C25 C 0.2032(2) 0.37109(13) -0.12776(10) 0.0255(3) Uani 1 1 d . . . . .
H25 H 0.209181 0.370682 -0.193531 0.031 Uiso 1 1 calc R U . . .
C6 C 0.78975(18) -0.06454(12) 0.37842(9) 0.0175(3) Uani 1 1 d . . . . .
C3 C 1.11915(18) -0.18578(12) 0.39408(10) 0.0208(3) Uani 1 1 d . . . . .
H3 H 1.228918 -0.224685 0.399055 0.025 Uiso 1 1 calc R U . . .
C17 C 0.16363(19) 0.38823(13) 0.36748(10) 0.0230(3) Uani 1 1 d . . . . .
H17 H 0.158415 0.392356 0.434112 0.028 Uiso 1 1 calc R U . . .
C22 C 0.18462(18) 0.37099(12) 0.06467(9) 0.0184(3) Uani 1 1 d . . . . .
C23 C 0.11819(19) 0.26859(13) -0.01687(10) 0.0235(3) Uani 1 1 d . . . . .
H23 H 0.067616 0.200779 -0.005805 0.028 Uiso 1 1 calc R U . . .
C18 C 0.18402(19) 0.27911(12) 0.30256(10) 0.0226(3) Uani 1 1 d . . . . .
H18 H 0.193401 0.211312 0.325595 0.027 Uiso 1 1 calc R U . . .
C20 C 0.17866(17) 0.37416(12) 0.17056(9) 0.0170(3) Uani 1 1 d . . . . .
C12 C 0.68266(18) 0.17468(12) 0.05662(10) 0.0189(3) Uani 1 1 d . . . . .
C14 C 0.60805(19) 0.22874(13) -0.01910(10) 0.0228(3) Uani 1 1 d . . . . .
H14 H 0.553323 0.300652 -0.002637 0.027 Uiso 1 1 calc R U . . .
C1 C 0.79311(17) -0.17821(11) 0.39235(9) 0.0156(3) Uani 1 1 d . . . . .
C21 C 0.15935(18) 0.48038(12) 0.24181(10) 0.0197(3) Uani 1 1 d . . . . .
H21 H 0.151736 0.549902 0.221242 0.024 Uiso 1 1 calc R U . . .
C10 C 0.67462(17) 0.22681(12) 0.16446(10) 0.0184(3) Uani 1 1 d . . . . .
C19 C 0.19042(18) 0.27104(12) 0.20308(10) 0.0200(3) Uani 1 1 d . . . . .
H19 H 0.202443 0.197684 0.158289 0.024 Uiso 1 1 calc R U . . .
C16 C 0.6994(2) 0.06804(13) -0.14041(11) 0.0280(3) Uani 1 1 d . . . . .
H16 H 0.703288 0.031777 -0.207885 0.034 Uiso 1 1 calc R U . . .
C11 C 0.66194(18) 0.15294(12) 0.22636(10) 0.0207(3) Uani 1 1 d . . . . .
H11 H 0.658610 0.070671 0.197519 0.025 Uiso 1 1 calc R U . . .
C26 C 0.25837(19) 0.46885(12) 0.04215(10) 0.0229(3) Uani 1 1 d . . . . .
H26 H 0.304092 0.537377 0.095948 0.027 Uiso 1 1 calc R U . . .
C4 C 1.11832(18) -0.07265(13) 0.38011(9) 0.0214(3) Uani 1 1 d . . . . .
H4 H 1.229586 -0.036173 0.376162 0.026 Uiso 1 1 calc R U . . .
C15 C 0.6164(2) 0.17415(14) -0.11897(11) 0.0277(3) Uani 1 1 d . . . . .
H15 H 0.566857 0.208459 -0.170666 0.033 Uiso 1 1 calc R U . . .
C9 C 0.67644(18) 0.34953(12) 0.20903(10) 0.0207(3) Uani 1 1 d . . . . .
H9 H 0.683489 0.402817 0.170933 0.025 Uiso 1 1 calc R U . . .
C24 C 0.1283(2) 0.26893(13) -0.11444(10) 0.0263(3) Uani 1 1 d . . . . .
H24 H 0.085367 0.201493 -0.169766 0.032 Uiso 1 1 calc R U . . .
C13 C 0.7658(2) 0.06833(12) 0.02637(11) 0.0241(3) Uani 1 1 d . . . . .
H13 H 0.818620 0.032535 0.076518 0.029 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O2 C6 1.3481(15) . ?
O1 C2 1.3512(15) . ?
O4 N1 1.2231(15) . ?
O3 N1 1.2159(14) . ?
N2 C11 1.3361(17) . ?
N2 C7 1.3406(18) . ?
N1 C1 1.4669(16) . ?
N3 C16 1.3373(19) . ?
N3 C13 1.3408(18) . ?
N4 C21 1.3405(16) . ?
N4 C17 1.3419(17) . ?
C7 C8 1.3847(19) . ?
N5 C25 1.3367(19) . ?
N5 C26 1.3383(17) . ?
C2 C3 1.3895(18) . ?
C2 C1 1.3913(17) . ?
C5 C4 1.3859(19) . ?
C5 C6 1.3954(18) . ?
C8 C9 1.3851(19) . ?
C25 C24 1.375(2) . ?
C6 C1 1.3905(18) . ?
C3 C4 1.384(2) . ?
C17 C18 1.378(2) . ?
C22 C26 1.3914(19) . ?
C22 C23 1.3955(19) . ?
C22 C20 1.4829(17) . ?
C23 C24 1.3850(19) . ?
C18 C19 1.3811(18) . ?
C20 C21 1.3925(18) . ?
C20 C19 1.3949(18) . ?
C12 C13 1.3940(19) . ?
C12 C14 1.3949(18) . ?
C12 C10 1.4796(18) . ?
C14 C15 1.384(2) . ?
C10 C9 1.3929(19) . ?
C10 C11 1.3932(18) . ?
C16 C15 1.377(2) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C11 N2 C7 117.82(11) . . ?
O3 N1 O4 123.75(12) . . ?
O3 N1 C1 118.21(11) . . ?
O4 N1 C1 118.02(10) . . ?
C16 N3 C13 116.48(12) . . ?
C21 N4 C17 117.55(11) . . ?
N2 C7 C8 122.26(13) . . ?
C25 N5 C26 116.79(12) . . ?
O1 C2 C3 124.80(12) . . ?
O1 C2 C1 117.02(11) . . ?
C3 C2 C1 118.17(12) . . ?
C4 C5 C6 119.68(12) . . ?
C7 C8 C9 119.20(13) . . ?
N5 C25 C24 123.86(12) . . ?
O2 C6 C1 117.43(11) . . ?
O2 C6 C5 125.41(12) . . ?
C1 C6 C5 117.15(12) . . ?
C4 C3 C2 118.95(12) . . ?
N4 C17 C18 122.47(12) . . ?
C26 C22 C23 117.01(12) . . ?
C26 C22 C20 121.78(12) . . ?
C23 C22 C20 121.20(12) . . ?
C24 C23 C22 119.35(13) . . ?
C17 C18 C19 119.59(12) . . ?
C21 C20 C19 117.00(12) . . ?
C21 C20 C22 121.34(12) . . ?
C19 C20 C22 121.66(12) . . ?
C13 C12 C14 117.02(12) . . ?
C13 C12 C10 120.95(12) . . ?
C14 C12 C10 122.03(12) . . ?
C15 C14 C12 119.25(13) . . ?
C6 C1 C2 123.66(12) . . ?
C6 C1 N1 118.95(11) . . ?
C2 C1 N1 117.38(11) . . ?
N4 C21 C20 124.14(12) . . ?
C9 C10 C11 116.65(12) . . ?
C9 C10 C12 122.89(12) . . ?
C11 C10 C12 120.45(12) . . ?
C18 C19 C20 119.24(12) . . ?
N3 C16 C15 123.93(13) . . ?
N2 C11 C10 124.43(12) . . ?
N5 C26 C22 124.39(13) . . ?
C3 C4 C5 122.39(12) . . ?
C16 C15 C14 118.77(13) . . ?
C8 C9 C10 119.64(12) . . ?
C25 C24 C23 118.59(13) . . ?
N3 C13 C12 124.55(13) . . ?
 
_refine_diff_density_max    0.249
_refine_diff_density_min   -0.233
_refine_diff_density_rms    0.047


 
data_7NRES-44BP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C42 H34 N8 O8' 
_chemical_formula_weight          778.77

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.4323(10)
_cell_length_b                    9.1138(12)
_cell_length_c                    14.562(2)
_cell_angle_alpha                 106.397(7)
_cell_angle_beta                  103.133(7)
_cell_angle_gamma                 90.486(6)
_cell_volume                      918.7(2)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     8552
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.5
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.408          
_exptl_crystal_F_000              406
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.100
_shelx_estimated_absorpt_T_min    0.980
_shelx_estimated_absorpt_T_max    0.980
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.829
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9526
_diffrn_reflns_av_unetI/netI      0.0319
_diffrn_reflns_av_R_equivalents   0.0236
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.004
_diffrn_reflns_theta_max          27.475
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4200
_reflns_number_gt                 3376
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0807P)²+0.2379P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4200
_refine_ls_number_parameters      264
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0582
_refine_ls_R_factor_gt            0.0453
_refine_ls_wR_factor_ref          0.1424
_refine_ls_wR_factor_gt           0.1266
_refine_ls_goodness_of_fit_ref    1.070
_refine_ls_restrained_S_all       1.070
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.21704(15) 0.14715(12) 0.88284(9) 0.0252(3) Uani 1 1 d . . . . .
H1 H 0.319935 0.192423 0.897080 0.038 Uiso 1 1 calc R U . . .
O2 O -0.10204(15) -0.34219(11) 0.74466(8) 0.0248(3) Uani 1 1 d . . . . .
H2 H -0.096850 -0.427216 0.707049 0.037 Uiso 1 1 calc R U . . .
O3 O -0.15821(16) -0.08161(13) 0.90132(9) 0.0295(3) Uani 1 1 d . . . . .
N4 N -0.10142(16) -0.03893(13) 0.83987(9) 0.0186(3) Uani 1 1 d . . . . .
O4 O -0.17775(15) 0.05119(13) 0.79823(9) 0.0284(3) Uani 1 1 d . . . . .
C20 C 0.0598(2) -0.25839(16) 0.76464(11) 0.0194(3) Uani 1 1 d . . . . .
C24 C 0.2264(2) -0.00238(16) 0.83693(11) 0.0198(3) Uani 1 1 d . . . . .
C21 C 0.2204(2) -0.31727(17) 0.73899(12) 0.0246(3) Uani 1 1 d . . . . .
H21 H 0.220309 -0.420693 0.705750 0.029 Uiso 1 1 calc R U . . .
N1 N 0.54938(18) 0.30714(15) 0.93048(10) 0.0253(3) Uani 1 1 d . . . . .
C16 C 0.9057(2) 0.45992(16) 0.98543(10) 0.0199(3) Uani 1 1 d . . . . .
C19 C 0.06763(19) -0.10135(16) 0.81344(11) 0.0180(3) Uani 1 1 d . . . . .
C23 C 0.3858(2) -0.06496(18) 0.81172(12) 0.0249(3) Uani 1 1 d . . . . .
H23 H 0.494929 -0.002944 0.827173 0.030 Uiso 1 1 calc R U . . .
C22 C 0.3799(2) -0.22061(19) 0.76339(13) 0.0272(4) Uani 1 1 d . . . . .
H22 H 0.486486 -0.261309 0.746840 0.033 Uiso 1 1 calc R U . . .
C14 C 0.5828(2) 0.43088(19) 0.90304(12) 0.0284(4) Uani 1 1 d . . . . .
H14 H 0.484398 0.465825 0.864840 0.034 Uiso 1 1 calc R U . . .
C17 C 0.8703(2) 0.33113(18) 1.01360(12) 0.0254(3) Uani 1 1 d . . . . .
H17 H 0.965929 0.292811 1.051418 0.030 Uiso 1 1 calc R U . . .
C15 C 0.7546(2) 0.50992(19) 0.92796(13) 0.0277(4) Uani 1 1 d . . . . .
H15 H 0.769851 0.595460 0.906852 0.033 Uiso 1 1 calc R U . . .
C18 C 0.6935(2) 0.25988(18) 0.98557(13) 0.0282(4) Uani 1 1 d . . . . .
H18 H 0.673564 0.174568 1.006083 0.034 Uiso 1 1 calc R U . . .
N3 N 0.0849(2) 0.62517(14) 0.36843(11) 0.0289(3) Uani 1 1 d . . . . .
C1 C 0.0862(2) 0.81472(17) 0.52020(12) 0.0256(3) Uani 1 1 d . . . . .
H1A H 0.111178 0.840348 0.588598 0.031 Uiso 1 1 calc R U . . .
C6 C 0.0181(2) 0.92136(15) 0.47266(11) 0.0208(3) Uani 1 1 d . . . . .
C7 C 0.4756(2) 1.08148(17) 0.51344(12) 0.0233(3) Uani 1 1 d . . . . .
N2 N 0.3854(2) 1.38947(17) 0.56473(12) 0.0370(4) Uani 1 1 d . . . . .
C12 C 0.4143(3) 1.15596(19) 0.44372(13) 0.0343(4) Uani 1 1 d . . . . .
H12 H 0.401119 1.104982 0.377235 0.041 Uiso 1 1 calc R U . . .
C2 C 0.1174(2) 0.66986(17) 0.46629(13) 0.0277(4) Uani 1 1 d . . . . .
H2A H 0.163354 0.600342 0.500164 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3720(3) 1.3080(2) 0.47285(15) 0.0383(4) Uani 1 1 d . . . . .
H11 H 0.331262 1.355318 0.423856 0.046 Uiso 1 1 calc R U . . .
C4 C 0.0213(4) 0.7274(2) 0.32252(15) 0.0535(6) Uani 1 1 d . . . . .
H4 H -0.001496 0.698725 0.254109 0.064 Uiso 1 1 calc R U . . .
C8 C 0.4930(4) 1.1663(3) 0.61003(15) 0.0623(8) Uani 1 1 d . . . . .
H8 H 0.535663 1.122823 0.660800 0.075 Uiso 1 1 calc R U . . .
C5 C -0.0132(4) 0.8747(2) 0.37083(14) 0.0517(6) Uani 1 1 d . . . . .
H5 H -0.057295 0.942143 0.334993 0.062 Uiso 1 1 calc R U . . .
C9 C 0.4463(4) 1.3175(3) 0.63100(16) 0.0680(8) Uani 1 1 d . . . . .
H9 H 0.459066 1.371918 0.696893 0.082 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C24 1.3482(17) . ?
O2 C20 1.3473(18) . ?
O3 N4 1.2229(17) . ?
N4 O4 1.2234(16) . ?
N4 C19 1.4692(17) . ?
C20 C21 1.397(2) . ?
C20 C19 1.4009(19) . ?
C24 C19 1.396(2) . ?
C24 C23 1.398(2) . ?
C21 C22 1.386(2) . ?
N1 C14 1.337(2) . ?
N1 C18 1.337(2) . ?
C16 C17 1.390(2) . ?
C16 C15 1.403(2) . ?
C16 C16 1.488(3) 2_767 ?
C23 C22 1.390(2) . ?
C14 C15 1.381(2) . ?
C17 C18 1.381(2) . ?
N3 C4 1.325(2) . ?
N3 C2 1.330(2) . ?
C1 C6 1.382(2) . ?
C1 C2 1.384(2) . ?
C6 C5 1.385(2) . ?
C6 C6 1.490(3) 2_576 ?
C7 C12 1.372(2) . ?
C7 C8 1.376(2) . ?
C7 C7 1.495(3) 2_676 ?
N2 C11 1.315(2) . ?
N2 C9 1.315(3) . ?
C12 C11 1.391(2) . ?
C4 C5 1.384(2) . ?
C8 C9 1.390(3) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O3 N4 O4 124.08(12) . . ?
O3 N4 C19 117.95(12) . . ?
O4 N4 C19 117.96(12) . . ?
O2 C20 C21 124.38(13) . . ?
O2 C20 C19 117.99(12) . . ?
C21 C20 C19 117.63(13) . . ?
O1 C24 C19 118.12(12) . . ?
O1 C24 C23 124.08(14) . . ?
C19 C24 C23 117.80(13) . . ?
C22 C21 C20 119.59(14) . . ?
C14 N1 C18 116.63(14) . . ?
C17 C16 C15 116.45(14) . . ?
C17 C16 C16 121.67(17) . 2_767 ?
C15 C16 C16 121.88(17) . 2_767 ?
C24 C19 C20 123.30(13) . . ?
C24 C19 N4 118.95(12) . . ?
C20 C19 N4 117.74(12) . . ?
C22 C23 C24 119.42(14) . . ?
C21 C22 C23 122.24(14) . . ?
N1 C14 C15 123.98(16) . . ?
C18 C17 C16 120.15(15) . . ?
C14 C15 C16 119.34(15) . . ?
N1 C18 C17 123.44(15) . . ?
C4 N3 C2 116.85(14) . . ?
C6 C1 C2 120.17(15) . . ?
C1 C6 C5 116.28(14) . . ?
C1 C6 C6 122.20(17) . 2_576 ?
C5 C6 C6 121.52(17) . 2_576 ?
C12 C7 C8 116.15(15) . . ?
C12 C7 C7 122.13(18) . 2_676 ?
C8 C7 C7 121.71(19) . 2_676 ?
C11 N2 C9 115.06(15) . . ?
C7 C12 C11 119.76(16) . . ?
N3 C2 C1 123.24(15) . . ?
N2 C11 C12 124.66(17) . . ?
N3 C4 C5 123.56(17) . . ?
C7 C8 C9 119.39(19) . . ?
C4 C5 C6 119.90(17) . . ?
N2 C9 C8 124.97(19) . . ?
 
_refine_diff_density_max    0.332
_refine_diff_density_min   -0.369
_refine_diff_density_rms    0.060


 
data_8NRES-DPE-I
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H17 N3 O4' 
_chemical_formula_weight          339.34

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    17.802(3)
_cell_length_b                    7.5355(11)
_cell_length_c                    12.5671(19)
_cell_angle_alpha                 90
_cell_angle_beta                  91.187(6)
_cell_angle_gamma                 90
_cell_volume                      1685.5(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     13038
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       27.7
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.337          
_exptl_crystal_F_000              712
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.096
_shelx_estimated_absorpt_T_min    0.981
_shelx_estimated_absorpt_T_max    0.981
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.752
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             16334
_diffrn_reflns_av_unetI/netI      0.0577
_diffrn_reflns_av_R_equivalents   0.0737
_diffrn_reflns_limit_h_min        -23
_diffrn_reflns_limit_h_max        23
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.152
_diffrn_reflns_theta_max          27.483
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3859
_reflns_number_gt                 2673
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0721P)²+1.9128P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3859
_refine_ls_number_parameters      228
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1016
_refine_ls_R_factor_gt            0.0736
_refine_ls_wR_factor_ref          0.1989
_refine_ls_wR_factor_gt           0.1832
_refine_ls_goodness_of_fit_ref    1.086
_refine_ls_restrained_S_all       1.086
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O2 O 0.83534(12) 0.1880(3) 0.77910(16) 0.0330(5) Uani 1 1 d . . . . .
H2 H 0.860190 0.277402 0.791915 0.050 Uiso 1 1 calc R U . . .
O1 O 0.66069(13) -0.0619(3) 0.53742(17) 0.0393(6) Uani 1 1 d . . . . .
H1 H 0.635883 -0.041637 0.483071 0.059 Uiso 1 1 calc R U . . .
O4 O 0.70962(13) -0.0781(3) 0.80485(17) 0.0406(6) Uani 1 1 d . . . . .
O3 O 0.77914(14) -0.2170(3) 0.6928(2) 0.0478(6) Uani 1 1 d . . . . .
N3 N 0.74516(14) -0.0852(3) 0.72221(19) 0.0287(5) Uani 1 1 d . . . . .
N2 N 0.90735(15) 0.4803(3) 0.8462(2) 0.0349(6) Uani 1 1 d . . . . .
N1 N 0.58340(14) -0.0297(4) 0.3534(2) 0.0334(6) Uani 1 1 d . . . . .
C6 C 0.79470(15) 0.2120(4) 0.6882(2) 0.0261(6) Uani 1 1 d . . . . .
C1 C 0.74767(15) 0.0740(4) 0.6550(2) 0.0253(6) Uani 1 1 d . . . . .
C2 C 0.70453(16) 0.0795(4) 0.5608(2) 0.0284(6) Uani 1 1 d . . . . .
C11 C 0.96895(17) 0.7614(4) 0.9644(2) 0.0303(6) Uani 1 1 d . . . . .
C7 C 0.98037(18) 0.5232(4) 0.8398(2) 0.0326(7) Uani 1 1 d . . . . .
H7 H 1.010590 0.456860 0.795306 0.039 Uiso 1 1 calc R U . . .
C5 C 0.79792(16) 0.3626(4) 0.6242(2) 0.0308(6) Uani 1 1 d . . . . .
H5 H 0.827660 0.458504 0.644898 0.037 Uiso 1 1 calc R U . . .
C10 C 1.01236(16) 0.6613(4) 0.8965(2) 0.0312(6) Uani 1 1 d . . . . .
H10 H 1.063061 0.687326 0.889239 0.037 Uiso 1 1 calc R U . . .
C3 C 0.71006(16) 0.2306(4) 0.4967(2) 0.0309(6) Uani 1 1 d . . . . .
H3 H 0.682919 0.238397 0.432811 0.037 Uiso 1 1 calc R U . . .
C4 C 0.75657(17) 0.3687(4) 0.5297(2) 0.0322(7) Uani 1 1 d . . . . .
H4 H 0.760119 0.468862 0.486811 0.039 Uiso 1 1 calc R U . . .
C13 C 0.62871(18) -0.0466(4) 0.2708(2) 0.0348(7) Uani 1 1 d . . . . .
H13 H 0.680331 -0.046144 0.283739 0.042 Uiso 1 1 calc R U . . .
C9 C 0.89352(18) 0.7174(4) 0.9702(3) 0.0376(7) Uani 1 1 d . . . . .
H9 H 0.862006 0.781271 1.014196 0.045 Uiso 1 1 calc R U . . .
C12 C 1.00254(19) 0.9110(4) 1.0297(2) 0.0359(7) Uani 1 1 d . . . . .
H12A H 1.054809 0.884529 1.046306 0.043 Uiso 1 1 calc R U . . .
H12B H 0.976215 0.920443 1.096293 0.043 Uiso 1 1 calc R U . . .
C14 C 0.50914(18) -0.0266(4) 0.3326(3) 0.0375(7) Uani 1 1 d . . . . .
H14 H 0.476569 -0.014994 0.389125 0.045 Uiso 1 1 calc R U . . .
C17 C 0.52625(19) -0.0622(4) 0.1450(3) 0.0381(8) Uani 1 1 d . . . . .
C8 C 0.86558(18) 0.5780(5) 0.9100(3) 0.0405(8) Uani 1 1 d . . . . .
H8 H 0.814754 0.551033 0.914374 0.049 Uiso 1 1 calc R U . . .
C15 C 0.60292(18) -0.0646(5) 0.1674(3) 0.0394(8) Uani 1 1 d . . . . .
H15 H 0.636789 -0.078255 0.112661 0.047 Uiso 1 1 calc R U . . .
C16 C 0.47917(18) -0.0401(4) 0.2306(3) 0.0395(8) Uani 1 1 d . . . . .
H16 H 0.427427 -0.034386 0.219380 0.047 Uiso 1 1 calc R U . . .
C18 C 0.4975(3) -0.0832(5) 0.0314(3) 0.0561(11) Uani 1 1 d . . . . .
H18A H 0.526368 -0.175011 -0.003218 0.067 Uiso 1 1 calc R U . . .
H18B H 0.445531 -0.121759 0.032196 0.067 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O2 C6 1.352(3) . ?
O2 H2 0.8200 . ?
O1 C2 1.350(4) . ?
O1 H1 0.8200 . ?
O4 N3 1.228(3) . ?
O3 N3 1.224(3) . ?
N3 C1 1.469(4) . ?
N2 C8 1.328(4) . ?
N2 C7 1.343(4) . ?
N1 C13 1.334(4) . ?
N1 C14 1.342(4) . ?
C6 C5 1.392(4) . ?
C6 C1 1.394(4) . ?
C1 C2 1.398(4) . ?
C2 C3 1.400(4) . ?
C11 C10 1.386(4) . ?
C11 C9 1.386(4) . ?
C11 C12 1.511(4) . ?
C7 C10 1.378(4) . ?
C7 H7 0.9300 . ?
C5 C4 1.386(4) . ?
C5 H5 0.9300 . ?
C10 H10 0.9300 . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C13 C15 1.376(4) . ?
C13 H13 0.9300 . ?
C9 C8 1.382(5) . ?
C9 H9 0.9300 . ?
C12 C12 1.537(6) 3_777 ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C14 C16 1.382(5) . ?
C14 H14 0.9300 . ?
C17 C16 1.388(5) . ?
C17 C15 1.388(5) . ?
C17 C18 1.514(4) . ?
C8 H8 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C18 1.486(7) 3_655 ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 O2 H2 109.5 . . ?
C2 O1 H1 109.5 . . ?
O3 N3 O4 123.9(3) . . ?
O3 N3 C1 117.9(2) . . ?
O4 N3 C1 118.2(2) . . ?
C8 N2 C7 117.2(3) . . ?
C13 N1 C14 117.3(3) . . ?
O2 C6 C5 124.7(2) . . ?
O2 C6 C1 117.5(2) . . ?
C5 C6 C1 117.8(2) . . ?
C6 C1 C2 123.2(3) . . ?
C6 C1 N3 117.5(2) . . ?
C2 C1 N3 119.2(2) . . ?
O1 C2 C1 117.8(3) . . ?
O1 C2 C3 124.3(3) . . ?
C1 C2 C3 117.9(3) . . ?
C10 C11 C9 117.1(3) . . ?
C10 C11 C12 121.4(3) . . ?
C9 C11 C12 121.5(3) . . ?
N2 C7 C10 122.8(3) . . ?
N2 C7 H7 118.6 . . ?
C10 C7 H7 118.6 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C10 C11 120.0(3) . . ?
C7 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C4 C3 C2 119.1(3) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 122.3(3) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
N1 C13 C15 123.3(3) . . ?
N1 C13 H13 118.3 . . ?
C15 C13 H13 118.3 . . ?
C8 C9 C11 119.4(3) . . ?
C8 C9 H9 120.3 . . ?
C11 C9 H9 120.3 . . ?
C11 C12 C12 111.6(3) . 3_777 ?
C11 C12 H12A 109.3 . . ?
C12 C12 H12A 109.3 3_777 . ?
C11 C12 H12B 109.3 . . ?
C12 C12 H12B 109.3 3_777 . ?
H12A C12 H12B 108.0 . . ?
N1 C14 C16 122.6(3) . . ?
N1 C14 H14 118.7 . . ?
C16 C14 H14 118.7 . . ?
C16 C17 C15 116.8(3) . . ?
C16 C17 C18 123.1(3) . . ?
C15 C17 C18 120.1(3) . . ?
N2 C8 C9 123.6(3) . . ?
N2 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C13 C15 C17 119.9(3) . . ?
C13 C15 H15 120.1 . . ?
C17 C15 H15 120.1 . . ?
C14 C16 C17 120.0(3) . . ?
C14 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C18 C17 112.9(4) 3_655 . ?
C18 C18 H18A 109.0 3_655 . ?
C17 C18 H18A 109.0 . . ?
C18 C18 H18B 109.0 3_655 . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
 
_refine_diff_density_max    0.508
_refine_diff_density_min   -0.397
_refine_diff_density_rms    0.067


 
data_9NRES-DPE-II
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C18 H15 N3 O4' 
_chemical_formula_weight          337.33

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    17.9122(13)
_cell_length_b                    7.4259(5)
_cell_length_c                    12.1765(8)
_cell_angle_alpha                 90
_cell_angle_beta                  92.337(7)
_cell_angle_gamma                 90
_cell_volume                      1618.30(19)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     13763
_cell_measurement_theta_min       3.2
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.385          
_exptl_crystal_F_000              704
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.100
_shelx_estimated_absorpt_T_min    0.980
_shelx_estimated_absorpt_T_max    0.980
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.818
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             16284
_diffrn_reflns_av_unetI/netI      0.0333
_diffrn_reflns_av_R_equivalents   0.0403
_diffrn_reflns_limit_h_min        -23
_diffrn_reflns_limit_h_max        23
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.214
_diffrn_reflns_theta_max          27.481
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3707
_reflns_number_gt                 2933
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0487P)²+0.5466P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3707
_refine_ls_number_parameters      236
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0563
_refine_ls_R_factor_gt            0.0425
_refine_ls_wR_factor_ref          0.1078
_refine_ls_wR_factor_gt           0.1008
_refine_ls_goodness_of_fit_ref    1.027
_refine_ls_restrained_S_all       1.027
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O001 O 0.84598(6) 0.14176(14) 0.79383(8) 0.0263(3) Uani 1 1 d . . . . .
H001 H 0.870566 0.232785 0.807436 0.039 Uiso 1 1 calc R U . . .
O002 O 0.65923(6) -0.10196(14) 0.55885(8) 0.0265(3) Uani 1 1 d . . . . .
H002 H 0.633943 -0.083770 0.502280 0.040 Uiso 1 1 calc R U . . .
O003 O 0.71992(6) -0.12122(15) 0.82946(8) 0.0322(3) Uani 1 1 d . . . . .
O004 O 0.78070(7) -0.26443(15) 0.70767(10) 0.0378(3) Uani 1 1 d . . . . .
N3 N 0.75081(7) -0.12920(16) 0.74151(10) 0.0225(3) Uani 1 1 d . . . . .
N1 N 0.91348(7) 0.44416(17) 0.86049(10) 0.0249(3) Uani 1 1 d . . . . .
N2 N 0.57684(7) -0.05617(18) 0.37171(10) 0.0257(3) Uani 1 1 d . . . . .
C2 C 0.70284(8) 0.04221(19) 0.58097(11) 0.0200(3) Uani 1 1 d . . . . .
C1 C 0.75126(8) 0.03328(18) 0.67354(11) 0.0192(3) Uani 1 1 d . . . . .
C6 C 0.79998(8) 0.17128(19) 0.70537(11) 0.0201(3) Uani 1 1 d . . . . .
C11 C 0.94985(8) 0.7850(2) 0.94646(11) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.70334(8) 0.1996(2) 0.51904(11) 0.0235(3) Uani 1 1 d . . . . .
H3 H 0.671866 0.211037 0.456779 0.028 Uiso 1 1 calc R U . . .
C17 C 0.51532(8) -0.02266(19) 0.15729(11) 0.0219(3) Uani 1 1 d . . . . .
C5 C 0.79905(8) 0.32735(19) 0.64239(12) 0.0227(3) Uani 1 1 d . . . . .
H5 H 0.830423 0.423021 0.661677 0.027 Uiso 1 1 calc R U . . .
C4 C 0.75089(8) 0.3393(2) 0.55045(12) 0.0242(3) Uani 1 1 d . . . . .
H4 H 0.750515 0.444101 0.508661 0.029 Uiso 1 1 calc R U . . .
C18 C 0.48157(8) -0.0022(2) 0.04614(12) 0.0249(3) Uani 1 1 d . . . . .
C13 C 0.61992(8) -0.0417(2) 0.28507(12) 0.0247(3) Uani 1 1 d . . . . .
H13 H 0.671487 -0.041738 0.297632 0.030 Uiso 1 1 calc R U . . .
C15 C 0.59230(8) -0.0269(2) 0.17836(12) 0.0251(3) Uani 1 1 d . . . . .
H15 H 0.624753 -0.019816 0.120807 0.030 Uiso 1 1 calc R U . . .
C10 C 1.00089(8) 0.6850(2) 0.88797(12) 0.0250(3) Uani 1 1 d . . . . .
H10 H 1.048293 0.730747 0.876681 0.030 Uiso 1 1 calc R U . . .
C16 C 0.47049(8) -0.0365(2) 0.24730(12) 0.0265(3) Uani 1 1 d . . . . .
H16 H 0.418753 -0.033400 0.237371 0.032 Uiso 1 1 calc R U . . .
C7 C 0.98076(8) 0.5181(2) 0.84698(12) 0.0257(3) Uani 1 1 d . . . . .
H7 H 1.015524 0.453650 0.808090 0.031 Uiso 1 1 calc R U . . .
C9 C 0.88026(8) 0.7079(2) 0.96030(13) 0.0270(3) Uani 1 1 d . . . . .
H9 H 0.844227 0.769146 0.998578 0.032 Uiso 1 1 calc R U . . .
C12 C 0.96634(9) 0.9640(2) 0.99265(12) 0.0251(3) Uani 1 1 d . . . . .
C8 C 0.86502(8) 0.5400(2) 0.91682(13) 0.0280(3) Uani 1 1 d . . . . .
H8 H 0.818162 0.490518 0.927378 0.034 Uiso 1 1 calc R U . . .
C14 C 0.50289(9) -0.0549(2) 0.35165(12) 0.0285(3) Uani 1 1 d . . . . .
H14 H 0.471852 -0.066920 0.410597 0.034 Uiso 1 1 calc R U . . .
H12 H 0.9231(10) 1.034(3) 1.0122(14) 0.036(5) Uiso 1 1 d . . . . .
H18 H 0.4281(10) 0.008(2) 0.0447(13) 0.030(4) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O001 C6 1.3472(16) . ?
O001 H001 0.8200 . ?
O002 C2 1.3460(17) . ?
O002 H002 0.8200 . ?
O003 N3 1.2267(16) . ?
O004 N3 1.2178(16) . ?
N3 C1 1.4634(18) . ?
N1 C8 1.334(2) . ?
N1 C7 1.3404(19) . ?
N2 C13 1.3366(19) . ?
N2 C14 1.3370(19) . ?
C2 C3 1.391(2) . ?
C2 C1 1.3954(19) . ?
C1 C6 1.391(2) . ?
C6 C5 1.389(2) . ?
C11 C9 1.388(2) . ?
C11 C10 1.396(2) . ?
C11 C12 1.469(2) . ?
C3 C4 1.386(2) . ?
C3 H3 0.9300 . ?
C17 C16 1.389(2) . ?
C17 C15 1.393(2) . ?
C17 C18 1.468(2) . ?
C5 C4 1.388(2) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C18 C18 1.327(3) 3_655 ?
C18 H18 0.960(17) . ?
C13 C15 1.376(2) . ?
C13 H13 0.9300 . ?
C15 H15 0.9300 . ?
C10 C7 1.379(2) . ?
C10 H10 0.9300 . ?
C16 C14 1.382(2) . ?
C16 H16 0.9300 . ?
C7 H7 0.9300 . ?
C9 C8 1.378(2) . ?
C9 H9 0.9300 . ?
C12 C12 1.325(3) 3_777 ?
C12 H12 0.971(18) . ?
C8 H8 0.9300 . ?
C14 H14 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 O001 H001 109.5 . . ?
C2 O002 H002 109.5 . . ?
O004 N3 O003 123.74(13) . . ?
O004 N3 C1 118.42(12) . . ?
O003 N3 C1 117.84(12) . . ?
C8 N1 C7 116.86(13) . . ?
C13 N2 C14 117.05(13) . . ?
O002 C2 C3 125.18(12) . . ?
O002 C2 C1 117.41(12) . . ?
C3 C2 C1 117.41(13) . . ?
C6 C1 C2 123.53(13) . . ?
C6 C1 N3 117.89(12) . . ?
C2 C1 N3 118.58(12) . . ?
O001 C6 C5 124.76(13) . . ?
O001 C6 C1 117.34(13) . . ?
C5 C6 C1 117.88(13) . . ?
C9 C11 C10 116.92(13) . . ?
C9 C11 C12 119.61(14) . . ?
C10 C11 C12 123.47(13) . . ?
C4 C3 C2 119.77(13) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C16 C17 C15 116.94(13) . . ?
C16 C17 C18 120.38(13) . . ?
C15 C17 C18 122.68(13) . . ?
C4 C5 C6 119.43(13) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C3 C4 C5 121.98(13) . . ?
C3 C4 H4 119.0 . . ?
C5 C4 H4 119.0 . . ?
C18 C18 C17 125.67(18) 3_655 . ?
C18 C18 H18 120.9(10) 3_655 . ?
C17 C18 H18 113.5(10) . . ?
N2 C13 C15 123.70(13) . . ?
N2 C13 H13 118.1 . . ?
C15 C13 H13 118.1 . . ?
C13 C15 C17 119.41(14) . . ?
C13 C15 H15 120.3 . . ?
C17 C15 H15 120.3 . . ?
C7 C10 C11 119.74(14) . . ?
C7 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C14 C16 C17 119.89(14) . . ?
C14 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N1 C7 C10 123.15(14) . . ?
N1 C7 H7 118.4 . . ?
C10 C7 H7 118.4 . . ?
C8 C9 C11 119.42(14) . . ?
C8 C9 H9 120.3 . . ?
C11 C9 H9 120.3 . . ?
C12 C12 C11 125.78(19) 3_777 . ?
C12 C12 H12 118.8(11) 3_777 . ?
C11 C12 H12 115.4(11) . . ?
N1 C8 C9 123.90(14) . . ?
N1 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
N2 C14 C16 122.99(14) . . ?
N2 C14 H14 118.5 . . ?
C16 C14 H14 118.5 . . ?
 
_refine_diff_density_max    0.249
_refine_diff_density_min   -0.261
_refine_diff_density_rms    0.047


 
data_10NRES-44AZO
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C16 H13 N5 O4' 
_chemical_formula_weight          339.31

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    18.213(3)
_cell_length_b                    7.2967(13)
_cell_length_c                    11.940(2)
_cell_angle_alpha                 90
_cell_angle_beta                  92.967(7)
_cell_angle_gamma                 90
_cell_volume                      1584.7(5)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     12104
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Block' 
_exptl_crystal_colour             'Red'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.422          
_exptl_crystal_F_000              704
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.106
_shelx_estimated_absorpt_T_min    0.979
_shelx_estimated_absorpt_T_max    0.979
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.686
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             14469
_diffrn_reflns_av_unetI/netI      0.0433
_diffrn_reflns_av_R_equivalents   0.0544
_diffrn_reflns_limit_h_min        -23
_diffrn_reflns_limit_h_max        23
_diffrn_reflns_limit_k_min        -9
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          3.008
_diffrn_reflns_theta_max          27.484
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3639
_reflns_number_gt                 2782
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0606P)²+1.0262P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3639
_refine_ls_number_parameters      228
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0743
_refine_ls_R_factor_gt            0.0577
_refine_ls_wR_factor_ref          0.1492
_refine_ls_wR_factor_gt           0.1393
_refine_ls_goodness_of_fit_ref    1.039
_refine_ls_restrained_S_all       1.039
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.14931(8) 0.1420(2) 0.20812(12) 0.0332(4) Uani 1 1 d . . . . .
H1 H 0.125878 0.235681 0.193280 0.050 Uiso 1 1 calc R U . . .
O2 O 0.34443(8) -0.0912(2) 0.43735(12) 0.0355(4) Uani 1 1 d . . . . .
H2 H 0.366096 -0.078145 0.498750 0.053 Uiso 1 1 calc R U . . .
O3 O 0.28655(10) -0.1186(2) 0.17188(13) 0.0467(4) Uani 1 1 d . . . . .
N5 N 0.24990(10) -0.1257(2) 0.25486(14) 0.0315(4) Uani 1 1 d . . . . .
O4 O 0.21592(11) -0.2609(2) 0.28178(16) 0.0527(5) Uani 1 1 d . . . . .
N2 N 0.08673(9) 0.4601(2) 0.13670(15) 0.0308(4) Uani 1 1 d . . . . .
N1 N 0.42295(10) -0.0529(2) 0.63618(14) 0.0327(4) Uani 1 1 d . . . . .
N3 N 0.51978(10) -0.0326(3) 0.96381(14) 0.0336(4) Uani 1 1 d . . . . .
N4 N 0.02702(9) 0.9600(2) -0.01889(15) 0.0328(4) Uani 1 1 d . . . . .
C2 C 0.19633(11) 0.1729(3) 0.29705(16) 0.0262(4) Uani 1 1 d . . . . .
C1 C 0.24772(11) 0.0378(3) 0.32621(16) 0.0260(4) Uani 1 1 d . . . . .
C6 C 0.29771(10) 0.0504(3) 0.41804(16) 0.0270(4) Uani 1 1 d . . . . .
C15 C 0.48363(11) -0.0370(3) 0.85373(17) 0.0297(4) Uani 1 1 d . . . . .
C16 C 0.40835(12) -0.0288(3) 0.83389(18) 0.0321(5) Uani 1 1 d . . . . .
H16 H 0.377159 -0.018648 0.892838 0.039 Uiso 1 1 calc R U . . .
C5 C 0.29578(11) 0.2091(3) 0.48352(17) 0.0301(4) Uani 1 1 d . . . . .
H5 H 0.328252 0.222838 0.545650 0.036 Uiso 1 1 calc R U . . .
C11 C 0.04509(11) 0.7909(3) 0.03891(17) 0.0296(4) Uani 1 1 d . . . . .
C3 C 0.19550(11) 0.3302(3) 0.36400(18) 0.0301(4) Uani 1 1 d . . . . .
H3 H 0.161904 0.423501 0.347387 0.036 Uiso 1 1 calc R U . . .
C4 C 0.24534(11) 0.3454(3) 0.45548(18) 0.0322(5) Uani 1 1 d . . . . .
H4 H 0.244818 0.450709 0.499326 0.039 Uiso 1 1 calc R U . . .
C12 C 0.38071(12) -0.0361(3) 0.72449(18) 0.0332(5) Uani 1 1 d . . . . .
H12 H 0.330040 -0.029003 0.711010 0.040 Uiso 1 1 calc R U . . .
C9 C -0.00082(11) 0.7028(3) 0.10984(18) 0.0318(5) Uani 1 1 d . . . . .
H9 H -0.046103 0.753017 0.125421 0.038 Uiso 1 1 calc R U . . .
C14 C 0.52882(12) -0.0556(3) 0.76363(18) 0.0338(5) Uani 1 1 d . . . . .
H14 H 0.579633 -0.063069 0.775031 0.041 Uiso 1 1 calc R U . . .
C13 C 0.49569(12) -0.0625(3) 0.65663(18) 0.0351(5) Uani 1 1 d . . . . .
H13 H 0.525501 -0.074499 0.596127 0.042 Uiso 1 1 calc R U . . .
C8 C 0.02203(12) 0.5383(3) 0.15724(18) 0.0338(5) Uani 1 1 d . . . . .
H8 H -0.008730 0.479178 0.205452 0.041 Uiso 1 1 calc R U . . .
C7 C 0.13056(12) 0.5487(3) 0.0683(2) 0.0354(5) Uani 1 1 d . . . . .
H7 H 0.175848 0.496890 0.054374 0.042 Uiso 1 1 calc R U . . .
C10 C 0.11191(12) 0.7128(3) 0.01741(19) 0.0365(5) Uani 1 1 d . . . . .
H10 H 0.143620 0.769674 -0.030330 0.044 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C2 1.348(2) . ?
O1 H1 0.8200 . ?
O2 C6 1.351(2) . ?
O2 H2 0.8200 . ?
O3 N5 1.224(2) . ?
N5 O4 1.216(2) . ?
N5 C1 1.468(3) . ?
N2 C7 1.338(3) . ?
N2 C8 1.343(3) . ?
N1 C13 1.337(3) . ?
N1 C12 1.343(3) . ?
N3 N3 1.248(3) 3_657 ?
N3 C15 1.440(3) . ?
N4 N4 1.249(3) 3_575 ?
N4 C11 1.444(3) . ?
C2 C1 1.391(3) . ?
C2 C3 1.399(3) . ?
C1 C6 1.392(3) . ?
C6 C5 1.398(3) . ?
C15 C16 1.381(3) . ?
C15 C14 1.395(3) . ?
C16 C12 1.376(3) . ?
C16 H16 0.9300 . ?
C5 C4 1.384(3) . ?
C5 H5 0.9300 . ?
C11 C9 1.379(3) . ?
C11 C10 1.380(3) . ?
C3 C4 1.388(3) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C12 H12 0.9300 . ?
C9 C8 1.382(3) . ?
C9 H9 0.9300 . ?
C14 C13 1.385(3) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C8 H8 0.9300 . ?
C7 C10 1.377(3) . ?
C7 H7 0.9300 . ?
C10 H10 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C6 O2 H2 109.5 . . ?
O4 N5 O3 123.70(19) . . ?
O4 N5 C1 118.44(17) . . ?
O3 N5 C1 117.86(18) . . ?
C7 N2 C8 117.60(18) . . ?
C13 N1 C12 117.66(18) . . ?
N3 N3 C15 112.8(2) 3_657 . ?
N4 N4 C11 113.0(2) 3_575 . ?
O1 C2 C1 118.06(17) . . ?
O1 C2 C3 124.17(18) . . ?
C1 C2 C3 117.74(18) . . ?
C2 C1 C6 123.68(18) . . ?
C2 C1 N5 117.97(17) . . ?
C6 C1 N5 118.35(17) . . ?
O2 C6 C1 117.68(17) . . ?
O2 C6 C5 124.87(17) . . ?
C1 C6 C5 117.45(18) . . ?
C16 C15 C14 119.50(19) . . ?
C16 C15 N3 123.98(19) . . ?
C14 C15 N3 116.50(18) . . ?
C12 C16 C15 118.18(19) . . ?
C12 C16 H16 120.9 . . ?
C15 C16 H16 120.9 . . ?
C4 C5 C6 119.72(18) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C9 C11 C10 119.37(19) . . ?
C9 C11 N4 124.15(18) . . ?
C10 C11 N4 116.45(19) . . ?
C4 C3 C2 119.30(19) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C5 C4 C3 122.12(19) . . ?
C5 C4 H4 118.9 . . ?
C3 C4 H4 118.9 . . ?
N1 C12 C16 123.55(19) . . ?
N1 C12 H12 118.2 . . ?
C16 C12 H12 118.2 . . ?
C11 C9 C8 118.47(19) . . ?
C11 C9 H9 120.8 . . ?
C8 C9 H9 120.8 . . ?
C13 C14 C15 117.95(19) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
N1 C13 C14 123.1(2) . . ?
N1 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
N2 C8 C9 122.9(2) . . ?
N2 C8 H8 118.6 . . ?
C9 C8 H8 118.6 . . ?
N2 C7 C10 123.2(2) . . ?
N2 C7 H7 118.4 . . ?
C10 C7 H7 118.4 . . ?
C7 C10 C11 118.5(2) . . ?
C7 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
 
_refine_diff_density_max    0.690
_refine_diff_density_min   -0.267
_refine_diff_density_rms    0.054


 
data_11NRES-4DMAP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C20 H25 N5 O4' 
_chemical_formula_weight          399.45

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.7563(12)
_cell_length_b                    8.1082(13)
_cell_length_c                    16.240(3)
_cell_angle_alpha                 97.387(7)
_cell_angle_beta                  95.164(7)
_cell_angle_gamma                 95.007(7)
_cell_volume                      1003.7(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     9048
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Brown'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.322          
_exptl_crystal_F_000              424
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.094
_shelx_estimated_absorpt_T_min    0.981
_shelx_estimated_absorpt_T_max    0.981
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.863
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication' 
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             10336
_diffrn_reflns_av_unetI/netI      0.0350
_diffrn_reflns_av_R_equivalents   0.0255
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          2.998
_diffrn_reflns_theta_max          27.476
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.994
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.994
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.994
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4570
_reflns_number_gt                 3549
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0522P)²+0.7433P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4570
_refine_ls_number_parameters      264
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0722
_refine_ls_R_factor_gt            0.0557
_refine_ls_wR_factor_ref          0.1444
_refine_ls_wR_factor_gt           0.1332
_refine_ls_goodness_of_fit_ref    1.077
_refine_ls_restrained_S_all       1.077
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O4 O 0.60341(17) 0.02852(17) 0.16535(9) 0.0287(3) Uani 1 1 d . . . . .
H4 H 0.630681 -0.055872 0.138149 0.043 Uiso 1 1 calc R U . . .
O1 O 0.50221(19) 0.43882(17) 0.24905(9) 0.0350(4) Uani 1 1 d . . . . .
N1 N 0.5560(2) 0.31112(19) 0.27075(9) 0.0236(3) Uani 1 1 d . . . . .
N3 N 0.6784(2) 0.7554(2) 1.07806(11) 0.0308(4) Uani 1 1 d . . . . .
O3 O 0.83865(19) 0.51870(18) 0.34057(10) 0.0380(4) Uani 1 1 d . . . . .
H3 H 0.929951 0.576277 0.358113 0.057 Uiso 1 1 calc R U . . .
N2 N 0.7794(2) 0.31238(19) 0.93565(10) 0.0256(3) Uani 1 1 d . . . . .
C6 C 0.7478(2) 0.1239(2) 0.20101(11) 0.0212(4) Uani 1 1 d . . . . .
O2 O 0.47029(19) 0.2152(2) 0.30746(10) 0.0389(4) Uani 1 1 d . . . . .
C10 C 0.6845(2) 0.5902(2) 0.94444(12) 0.0261(4) Uani 1 1 d . . . . .
H10 H 0.663863 0.581947 0.886679 0.031 Uiso 1 1 calc R U . . .
C3 C 1.0388(2) 0.3430(2) 0.27584(12) 0.0257(4) Uani 1 1 d . . . . .
H3A H 1.136288 0.413507 0.299944 0.031 Uiso 1 1 calc R U . . .
C1 C 0.7303(2) 0.2721(2) 0.25282(10) 0.0200(4) Uani 1 1 d . . . . .
C11 C 0.7526(2) 0.4583(2) 0.98166(11) 0.0222(4) Uani 1 1 d . . . . .
C2 C 0.8724(2) 0.3844(2) 0.29101(11) 0.0234(4) Uani 1 1 d . . . . .
C4 C 1.0583(3) 0.1971(2) 0.22495(12) 0.0277(4) Uani 1 1 d . . . . .
H4A H 1.169804 0.171106 0.215356 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6490(3) 0.7307(2) 0.99419(13) 0.0286(4) Uani 1 1 d . . . . .
H8 H 0.601479 0.814547 0.968222 0.034 Uiso 1 1 calc R U . . .
C5 C 0.9167(3) 0.0879(2) 0.18762(12) 0.0273(4) Uani 1 1 d . . . . .
H5 H 0.934373 -0.009250 0.153650 0.033 Uiso 1 1 calc R U . . .
C9 C 0.7880(2) 0.4862(2) 1.06950(12) 0.0268(4) Uani 1 1 d . . . . .
H9 H 0.837720 0.406161 1.097518 0.032 Uiso 1 1 calc R U . . .
C7 C 0.7484(3) 0.6320(3) 1.11318(12) 0.0299(4) Uani 1 1 d . . . . .
H7 H 0.771657 0.646531 1.170982 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8386(3) 0.1750(3) 0.97629(14) 0.0339(5) Uani 1 1 d . . . . .
H12A H 0.850695 0.082250 0.934803 0.051 Uiso 1 1 calc R U . . .
H12B H 0.948981 0.210303 1.008124 0.051 Uiso 1 1 calc R U . . .
H12C H 0.755295 0.141676 1.012784 0.051 Uiso 1 1 calc R U . . .
C13 C 0.7482(3) 0.2896(3) 0.84495(12) 0.0336(5) Uani 1 1 d . . . . .
H13A H 0.773823 0.179703 0.823069 0.050 Uiso 1 1 calc R U . . .
H13B H 0.628581 0.302381 0.828681 0.050 Uiso 1 1 calc R U . . .
H13C H 0.821769 0.371645 0.823302 0.050 Uiso 1 1 calc R U . . .
N4 N 0.0777(2) 0.7367(2) 0.41400(11) 0.0322(4) Uani 1 1 d . . . . .
N5 N 0.3475(2) 1.1630(2) 0.55655(11) 0.0347(4) Uani 1 1 d . . . . .
C16 C 0.2623(2) 1.0245(2) 0.50966(13) 0.0279(4) Uani 1 1 d . . . . .
C17 C 0.2203(4) 0.8794(3) 0.54327(17) 0.0655(10) Uani 1 1 d . . . . .
H17 H 0.253032 0.874380 0.599345 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3870(5) 1.3135(4) 0.51993(17) 0.0702(10) Uani 1 1 d . . . . .
H15A H 0.447237 1.398395 0.561815 0.105 Uiso 1 1 calc R U . . .
H15B H 0.459126 1.290205 0.475658 0.105 Uiso 1 1 calc R U . . .
H15C H 0.280782 1.351676 0.497988 0.105 Uiso 1 1 calc R U . . .
C14 C 0.3956(4) 1.1664(3) 0.64494(17) 0.0589(8) Uani 1 1 d . . . . .
H14A H 0.454592 1.273853 0.667727 0.088 Uiso 1 1 calc R U . . .
H14B H 0.292850 1.146499 0.672453 0.088 Uiso 1 1 calc R U . . .
H14C H 0.471400 1.081251 0.653308 0.088 Uiso 1 1 calc R U . . .
C20 C 0.1307(5) 0.7429(3) 0.49415(18) 0.0678(10) Uani 1 1 d . . . . .
H20 H 0.105426 0.647785 0.519041 0.081 Uiso 1 1 calc R U . . .
C19 C 0.1177(4) 0.8749(3) 0.38177(14) 0.0524(7) Uani 1 1 d . . . . .
H19 H 0.082156 0.875515 0.325576 0.063 Uiso 1 1 calc R U . . .
C18 C 0.2075(4) 1.0174(3) 0.42506(14) 0.0587(8) Uani 1 1 d . . . . .
H18 H 0.232110 1.109581 0.397897 0.070 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O4 C6 1.343(2) . ?
O1 N1 1.230(2) . ?
N1 O2 1.226(2) . ?
N1 C1 1.461(2) . ?
N3 C7 1.344(3) . ?
N3 C8 1.347(3) . ?
O3 C2 1.328(2) . ?
N2 C11 1.358(2) . ?
N2 C12 1.453(3) . ?
N2 C13 1.456(2) . ?
C6 C5 1.396(3) . ?
C6 C1 1.400(2) . ?
C10 C8 1.373(3) . ?
C10 C11 1.413(3) . ?
C3 C4 1.381(3) . ?
C3 C2 1.397(3) . ?
C1 C2 1.409(2) . ?
C11 C9 1.413(3) . ?
C4 C5 1.389(3) . ?
C9 C7 1.372(3) . ?
N4 C19 1.321(3) . ?
N4 C20 1.322(3) . ?
N5 C16 1.356(2) . ?
N5 C15 1.445(3) . ?
N5 C14 1.446(3) . ?
C16 C17 1.385(3) . ?
C16 C18 1.393(3) . ?
C17 C20 1.372(3) . ?
C19 C18 1.370(3) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 N1 O1 122.91(17) . . ?
O2 N1 C1 118.27(15) . . ?
O1 N1 C1 118.82(16) . . ?
C7 N3 C8 116.00(16) . . ?
C11 N2 C12 120.43(16) . . ?
C11 N2 C13 120.95(16) . . ?
C12 N2 C13 118.62(16) . . ?
O4 C6 C5 124.13(16) . . ?
O4 C6 C1 118.81(16) . . ?
C5 C6 C1 117.02(16) . . ?
C8 C10 C11 119.49(18) . . ?
C4 C3 C2 119.81(17) . . ?
C6 C1 C2 123.64(16) . . ?
C6 C1 N1 118.64(15) . . ?
C2 C1 N1 117.69(15) . . ?
N2 C11 C10 121.79(16) . . ?
N2 C11 C9 122.17(17) . . ?
C10 C11 C9 116.03(17) . . ?
O3 C2 C3 124.91(16) . . ?
O3 C2 C1 117.80(17) . . ?
C3 C2 C1 117.26(16) . . ?
C3 C4 C5 122.17(18) . . ?
N3 C8 C10 124.41(19) . . ?
C4 C5 C6 120.10(17) . . ?
C7 C9 C11 119.59(19) . . ?
N3 C7 C9 124.40(18) . . ?
C19 N4 C20 115.08(19) . . ?
C16 N5 C15 120.7(2) . . ?
C16 N5 C14 121.1(2) . . ?
C15 N5 C14 118.23(19) . . ?
N5 C16 C17 122.0(2) . . ?
N5 C16 C18 123.1(2) . . ?
C17 C16 C18 114.88(19) . . ?
C20 C17 C16 120.3(2) . . ?
N4 C20 C17 124.8(2) . . ?
N4 C19 C18 124.8(2) . . ?
C19 C18 C16 120.2(2) . . ?
 
_refine_diff_density_max    0.355
_refine_diff_density_min   -0.362
_refine_diff_density_rms    0.053


 
data_12NRES-4DMAP-II
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C13 H15 N3 O4' 
_chemical_formula_weight          277.28

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    10.1301(13)
_cell_length_b                    12.6967(17)
_cell_length_c                    10.3338(14)
_cell_angle_alpha                 90
_cell_angle_beta                  99.170(7)
_cell_angle_gamma                 90
_cell_volume                      1312.1(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     11747
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       27.5
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Brown'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.404          
_exptl_crystal_F_000              584
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.106
_shelx_estimated_absorpt_T_min    0.979
_shelx_estimated_absorpt_T_max    0.979
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.873
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             13192
_diffrn_reflns_av_unetI/netI      0.0216
_diffrn_reflns_av_R_equivalents   0.0273
_diffrn_reflns_limit_h_min        -13
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.068
_diffrn_reflns_theta_max          27.483
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              3009
_reflns_number_gt                 2568
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0410P)²+0.5219P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3009
_refine_ls_number_parameters      189
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0457
_refine_ls_R_factor_gt            0.0382
_refine_ls_wR_factor_ref          0.0938
_refine_ls_wR_factor_gt           0.0898
_refine_ls_goodness_of_fit_ref    1.034
_refine_ls_restrained_S_all       1.034
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.83809(9) 0.26442(7) 0.32904(8) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.53573(9) 0.15051(7) -0.04164(9) 0.0222(2) Uani 1 1 d . . . . .
O3 O 0.62117(11) 0.04678(7) 0.20127(10) 0.0323(2) Uani 1 1 d . . . . .
O4 O 0.56850(12) 0.18141(9) 0.30863(11) 0.0442(3) Uani 1 1 d . . . . .
N3 N 0.62215(10) 0.14152(8) 0.22227(10) 0.0210(2) Uani 1 1 d . . . . .
N1 N 0.70849(11) 0.36971(9) 0.50172(10) 0.0224(2) Uani 1 1 d . . . . .
N2 N 0.56869(11) 0.54280(8) 0.78994(11) 0.0235(2) Uani 1 1 d . . . . .
C9 C 0.79649(11) 0.27240(9) 0.20174(11) 0.0173(2) Uani 1 1 d . . . . .
C8 C 0.68854(11) 0.21079(9) 0.14036(11) 0.0163(2) Uani 1 1 d . . . . .
C13 C 0.63845(12) 0.21410(9) 0.00593(12) 0.0174(2) Uani 1 1 d . . . . .
C5 C 0.61419(12) 0.48747(9) 0.69533(12) 0.0189(3) Uani 1 1 d . . . . .
C10 C 0.85602(12) 0.33926(10) 0.11860(12) 0.0206(3) Uani 1 1 d . . . . .
H10 H 0.929336 0.380201 0.153158 0.025 Uiso 1 1 calc R U . . .
C12 C 0.69836(13) 0.28344(10) -0.07127(12) 0.0214(3) Uani 1 1 d . . . . .
H12 H 0.666561 0.289003 -0.160528 0.026 Uiso 1 1 calc R U . . .
C11 C 0.80628(13) 0.34450(10) -0.01405(13) 0.0228(3) Uani 1 1 d . . . . .
H11 H 0.846177 0.390213 -0.066575 0.027 Uiso 1 1 calc R U . . .
C3 C 0.53614(13) 0.40670(10) 0.62492(12) 0.0217(3) Uani 1 1 d . . . . .
H3 H 0.450970 0.392175 0.643022 0.026 Uiso 1 1 calc R U . . .
C2 C 0.58557(13) 0.35063(10) 0.53120(12) 0.0228(3) Uani 1 1 d . . . . .
H2 H 0.533418 0.297855 0.486336 0.027 Uiso 1 1 calc R U . . .
C4 C 0.74202(12) 0.50577(10) 0.66002(12) 0.0212(3) Uani 1 1 d . . . . .
H4 H 0.796760 0.558338 0.702058 0.025 Uiso 1 1 calc R U . . .
C1 C 0.78489(13) 0.44663(10) 0.56476(12) 0.0223(3) Uani 1 1 d . . . . .
H1 H 0.868885 0.459662 0.542725 0.027 Uiso 1 1 calc R U . . .
C6 C 0.43747(14) 0.51932(11) 0.82476(14) 0.0281(3) Uani 1 1 d . . . . .
H6A H 0.420588 0.565777 0.893583 0.042 Uiso 1 1 calc R U . . .
H6B H 0.369821 0.529097 0.749384 0.042 Uiso 1 1 calc R U . . .
H6C H 0.435829 0.447689 0.854188 0.042 Uiso 1 1 calc R U . . .
C7 C 0.64904(16) 0.62614(11) 0.86083(15) 0.0327(3) Uani 1 1 d . . . . .
H7A H 0.600875 0.656788 0.924288 0.049 Uiso 1 1 calc R U . . .
H7B H 0.731709 0.597100 0.904677 0.049 Uiso 1 1 calc R U . . .
H7C H 0.667413 0.679364 0.800154 0.049 Uiso 1 1 calc R U . . .
H2A H 0.469(2) 0.1849(18) -0.100(2) 0.064(6) Uiso 1 1 d . . . . .
H1A H 0.7412(18) 0.3302(14) 0.4382(17) 0.040(5) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 C9 1.3197(14) . ?
O2 C13 1.3467(14) . ?
O2 H2A 0.94(2) . ?
O3 N3 1.2220(14) . ?
O4 N3 1.2259(14) . ?
N3 C8 1.4573(15) . ?
N1 C1 1.3478(17) . ?
N1 C2 1.3502(17) . ?
N1 H1A 0.928(18) . ?
N2 C5 1.3437(16) . ?
N2 C7 1.4591(18) . ?
N2 C6 1.4622(17) . ?
C9 C10 1.4098(17) . ?
C9 C8 1.4102(16) . ?
C8 C13 1.4015(16) . ?
C13 C12 1.3907(17) . ?
C5 C4 1.4194(17) . ?
C5 C3 1.4222(17) . ?
C10 C11 1.3846(18) . ?
C10 H10 0.9300 . ?
C12 C11 1.3927(18) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C3 C2 1.3601(18) . ?
C3 H3 0.9300 . ?
C2 H2 0.9300 . ?
C4 C1 1.3630(18) . ?
C4 H4 0.9300 . ?
C1 H1 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C13 O2 H2A 113.1(14) . . ?
O3 N3 O4 122.95(11) . . ?
O3 N3 C8 118.84(10) . . ?
O4 N3 C8 118.21(11) . . ?
C1 N1 C2 120.01(11) . . ?
C1 N1 H1A 119.4(11) . . ?
C2 N1 H1A 120.6(11) . . ?
C5 N2 C7 121.06(11) . . ?
C5 N2 C6 120.21(11) . . ?
C7 N2 C6 118.72(11) . . ?
O1 C9 C10 123.64(11) . . ?
O1 C9 C8 120.49(11) . . ?
C10 C9 C8 115.86(11) . . ?
C13 C8 C9 124.16(11) . . ?
C13 C8 N3 117.78(10) . . ?
C9 C8 N3 118.04(10) . . ?
O2 C13 C12 123.55(11) . . ?
O2 C13 C8 118.72(11) . . ?
C12 C13 C8 117.74(11) . . ?
N2 C5 C4 122.29(11) . . ?
N2 C5 C3 121.47(11) . . ?
C4 C5 C3 116.24(11) . . ?
C11 C10 C9 120.58(11) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C13 C12 C11 119.58(11) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C10 C11 C12 122.06(12) . . ?
C10 C11 H11 119.0 . . ?
C12 C11 H11 119.0 . . ?
C2 C3 C5 120.27(12) . . ?
C2 C3 H3 119.9 . . ?
C5 C3 H3 119.9 . . ?
N1 C2 C3 121.61(12) . . ?
N1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C1 C4 C5 120.28(12) . . ?
C1 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N1 C1 C4 121.58(12) . . ?
N1 C1 H1 119.2 . . ?
C4 C1 H1 119.2 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
 
_refine_diff_density_max    0.242
_refine_diff_density_min   -0.291
_refine_diff_density_rms    0.043


 
data_13NRES-TMP-PYR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C29 H26 N3 O4' 
_chemical_formula_weight          480.53

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    7.7925(13)
_cell_length_b                    12.885(2)
_cell_length_c                    12.398(2)
_cell_angle_alpha                 90
_cell_angle_beta                  104.054(7)
_cell_angle_gamma                 90
_cell_volume                      1207.6(4)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     9438
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.322          
_exptl_crystal_F_000              506
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.089
_shelx_estimated_absorpt_T_min    0.982
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.710
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             12163
_diffrn_reflns_av_unetI/netI      0.0789
_diffrn_reflns_av_R_equivalents   0.0572
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.124
_diffrn_reflns_theta_max          27.485
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              5506
_reflns_number_gt                 3193
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.908
_reflns_Friedel_fraction_max      0.991
_reflns_Friedel_fraction_full     0.998
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1152P)²+1.4802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 988 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    1.5(10)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          5506
_refine_ls_number_parameters      340
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1464
_refine_ls_R_factor_gt            0.0905
_refine_ls_wR_factor_ref          0.2760
_refine_ls_wR_factor_gt           0.2407
_refine_ls_goodness_of_fit_ref    1.051
_refine_ls_restrained_S_all       1.051
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O -0.8237(8) -0.4406(4) -0.3005(5) 0.0487(15) Uani 1 1 d . . . . .
O4 O -0.5663(6) -0.5084(6) -0.4455(3) 0.0445(14) Uani 1 1 d . . . . .
H4 H -0.508079 -0.528346 -0.488395 0.067 Uiso 1 1 calc R U . . .
N3 N -0.4249(7) -0.5172(6) 0.3740(4) 0.0327(12) Uani 1 1 d . . . . .
O3 O -0.5609(7) -0.5250(6) -0.0685(4) 0.0499(14) Uani 1 1 d . . . . .
H3 H -0.496933 -0.519335 -0.005639 0.075 Uiso 1 1 calc R U . . .
N1 N -0.7422(7) -0.5218(6) -0.2834(4) 0.0326(13) Uani 1 1 d . . . . .
N2 N -0.4071(8) -0.5266(5) 0.1548(4) 0.0329(13) Uani 1 1 d . . . . .
C13 C -0.4217(11) -0.6113(5) 0.2110(6) 0.0318(17) Uani 1 1 d . . . . .
O2 O -0.8155(10) -0.6067(5) -0.2897(6) 0.064(2) Uani 1 1 d . . . . .
C12 C -0.4317(10) -0.6079(5) 0.3214(6) 0.0285(16) Uani 1 1 d . . . . .
C2 C -0.4640(9) -0.5088(6) -0.3406(5) 0.0341(16) Uani 1 1 d . . . . .
C1 C -0.5497(8) -0.5152(6) -0.2554(5) 0.0278(13) Uani 1 1 d . . . . .
C6 C -0.4624(9) -0.5178(7) -0.1434(5) 0.0359(15) Uani 1 1 d . . . . .
C9 C -0.4048(10) -0.4289(6) 0.3188(6) 0.0312(17) Uani 1 1 d . . . . .
C5 C -0.2754(11) -0.5088(8) -0.1164(6) 0.048(2) Uani 1 1 d . . . . .
H5 H -0.211816 -0.506923 -0.042496 0.058 Uiso 1 1 calc R U . . .
C3 C -0.2789(10) -0.5020(7) -0.3122(6) 0.0391(18) Uani 1 1 d . . . . .
H3A H -0.216978 -0.496970 -0.367411 0.047 Uiso 1 1 calc R U . . .
C14 C -0.4315(13) -0.7138(6) 0.1487(7) 0.046(2) Uani 1 1 d . . . . .
H14A H -0.545543 -0.744797 0.142388 0.069 Uiso 1 1 calc R U . . .
H14B H -0.341256 -0.759807 0.188761 0.069 Uiso 1 1 calc R U . . .
H14C H -0.413716 -0.701588 0.075839 0.069 Uiso 1 1 calc R U . . .
C11 C -0.4503(15) -0.7040(6) 0.3851(7) 0.052(2) Uani 1 1 d . . . . .
H11A H -0.567753 -0.731219 0.359303 0.078 Uiso 1 1 calc R U . . .
H11B H -0.428986 -0.687631 0.462812 0.078 Uiso 1 1 calc R U . . .
H11C H -0.365968 -0.754795 0.374246 0.078 Uiso 1 1 calc R U . . .
C4 C -0.1889(10) -0.5028(7) -0.2007(6) 0.0436(19) Uani 1 1 d . . . . .
H4A H -0.066054 -0.499259 -0.182414 0.052 Uiso 1 1 calc R U . . .
C8 C -0.3979(11) -0.4331(6) 0.2066(6) 0.0365(18) Uani 1 1 d . . . . .
C27 C -0.9393(15) -0.4332(10) -0.5939(9) 0.067(3) Uani 1 1 d . . . . .
H27 H -0.954460 -0.426095 -0.522159 0.080 Uiso 1 1 calc R U . . .
C30 C -0.8851(12) -0.4578(8) -0.8089(8) 0.052(2) Uani 1 1 d . . . . .
C29 C -0.9149(11) -0.5494(7) -0.7506(8) 0.051(2) Uani 1 1 d . . . . .
C10 C -0.4009(14) -0.3274(7) 0.3810(9) 0.052(2) Uani 1 1 d . . . . .
H10A H -0.500623 -0.285716 0.345106 0.078 Uiso 1 1 calc R U . . .
H10B H -0.293544 -0.290842 0.381042 0.078 Uiso 1 1 calc R U . . .
H10C H -0.406205 -0.341214 0.456203 0.078 Uiso 1 1 calc R U . . .
C21 C -0.8578(14) -0.4716(8) -0.9155(9) 0.065(3) Uani 1 1 d . . . . .
C7 C -0.3668(18) -0.3399(7) 0.1442(8) 0.067(3) Uani 1 1 d . . . . .
H7A H -0.472134 -0.298308 0.126540 0.101 Uiso 1 1 calc R U . . .
H7B H -0.336834 -0.360826 0.076751 0.101 Uiso 1 1 calc R U . . .
H7C H -0.271394 -0.300228 0.188870 0.101 Uiso 1 1 calc R U . . .
C26 C -0.9154(14) -0.3495(9) -0.6492(9) 0.064(3) Uani 1 1 d . . . . .
H26 H -0.918443 -0.284034 -0.618109 0.076 Uiso 1 1 calc R U . . .
C28 C -0.9430(12) -0.5378(8) -0.6422(8) 0.060(3) Uani 1 1 d . . . . .
C25 C -0.8831(15) -0.3611(9) -0.7625(10) 0.066(3) Uani 1 1 d . . . . .
C22 C -0.8393(18) -0.3783(10) -0.9768(9) 0.082(4) Uani 1 1 d . . . . .
H22 H -0.823046 -0.383413 -1.048471 0.099 Uiso 1 1 calc R U . A 1
C15 C -0.9712(15) -0.6252(9) -0.5852(11) 0.075(3) Uani 1 1 d . . . . .
H15 H -0.989690 -0.619593 -0.514083 0.090 Uiso 1 1 calc R U . . .
C24 C -0.871(2) -0.2724(10) -0.8226(13) 0.108(6) Uani 1 1 d . . . . .
H24 H -0.879980 -0.207257 -0.792229 0.129 Uiso 1 1 calc R U . B 1
C23 C -0.846(3) -0.2819(10) -0.9293(12) 0.120(6) Uani 1 1 d . . . C 1
H23 H -0.832580 -0.222481 -0.969268 0.144 Uiso 1 1 calc R U . . .
C0AA C -0.9213(15) -0.6473(10) -0.7960(11) 0.070(4) Uani 1 1 d . . . . .
C2AA C -0.9435(19) -0.7298(11) -0.7447(14) 0.102(6) Uani 1 1 d . . . D 1
H2AA H -0.941615 -0.794417 -0.777825 0.123 Uiso 1 1 calc R U . D 1
C1AA C -0.9717(17) -0.7216(10) -0.6345(15) 0.095(5) Uani 1 1 d . . . . .
H1AA H -0.990284 -0.781079 -0.596368 0.114 Uiso 1 1 calc R U . D 1
C3AA C -0.861(2) -0.5829(13) -0.9426(14) 0.046(4) Uani 0.5 1 d . . P . .
H3AA H -0.848385 -0.599157 -1.013323 0.055 Uiso 0.5 1 calc R U P D .
C4AA C -0.879(3) -0.6604(14) -0.881(3) 0.094(11) Uani 0.5 1 d . . P D .
H4AA H -0.858439 -0.727330 -0.903681 0.112 Uiso 0.5 1 calc R U P E 2
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 N1 1.216(8) . ?
O4 C2 1.350(7) . ?
O4 H4 0.8200 . ?
N3 C12 1.333(10) . ?
N3 C9 1.356(10) . ?
O3 C6 1.343(8) . ?
O3 H3 0.8200 . ?
N1 O2 1.227(9) . ?
N1 C1 1.458(8) . ?
N2 C13 1.313(10) . ?
N2 C8 1.359(10) . ?
C13 C12 1.391(11) . ?
C13 C14 1.523(10) . ?
C12 C11 1.495(11) . ?
C2 C1 1.382(8) . ?
C2 C3 1.402(10) . ?
C1 C6 1.391(8) . ?
C6 C5 1.419(11) . ?
C9 C8 1.407(10) . ?
C9 C10 1.515(11) . ?
C5 C4 1.376(10) . ?
C5 H5 0.9300 . ?
C3 C4 1.390(10) . ?
C3 H3A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C4 H4A 0.9300 . ?
C8 C7 1.479(12) . ?
C27 C26 1.315(15) . ?
C27 C28 1.472(16) . ?
C27 H27 0.9300 . ?
C30 C25 1.371(15) . ?
C30 C21 1.400(14) . ?
C30 C29 1.433(12) . ?
C29 C0AA 1.377(14) . ?
C29 C28 1.421(13) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C21 C22 1.447(16) . ?
C21 C3AA 1.473(18) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C26 C25 1.493(16) . ?
C26 H26 0.9300 . ?
C28 C15 1.375(15) . ?
C25 C24 1.380(17) . ?
C22 C23 1.381(18) . ?
C22 H22 0.9300 . ?
C15 C1AA 1.383(18) . ?
C15 H15 0.9300 . ?
C24 C23 1.390(18) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C0AA C4AA 1.20(3) . ?
C0AA C2AA 1.27(2) . ?
C2AA C1AA 1.44(2) . ?
C2AA H2AA 0.9300 . ?
C1AA H1AA 0.9300 . ?
C3AA C4AA 1.28(3) . ?
C3AA H3AA 0.9300 . ?
C4AA H4AA 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 O4 H4 109.5 . . ?
C12 N3 C9 119.0(5) . . ?
C6 O3 H3 109.5 . . ?
O1 N1 O2 122.7(6) . . ?
O1 N1 C1 117.1(7) . . ?
O2 N1 C1 120.2(7) . . ?
C13 N2 C8 119.2(5) . . ?
N2 C13 C12 121.9(6) . . ?
N2 C13 C14 116.9(7) . . ?
C12 C13 C14 121.2(7) . . ?
N3 C12 C13 120.3(6) . . ?
N3 C12 C11 117.7(7) . . ?
C13 C12 C11 122.0(7) . . ?
O4 C2 C1 117.0(6) . . ?
O4 C2 C3 124.9(6) . . ?
C1 C2 C3 118.1(5) . . ?
C2 C1 C6 123.7(6) . . ?
C2 C1 N1 118.8(5) . . ?
C6 C1 N1 117.5(5) . . ?
O3 C6 C1 118.0(6) . . ?
O3 C6 C5 124.7(5) . . ?
C1 C6 C5 117.3(6) . . ?
N3 C9 C8 120.3(6) . . ?
N3 C9 C10 117.3(7) . . ?
C8 C9 C10 122.4(7) . . ?
C4 C5 C6 119.3(6) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C4 C3 C2 119.2(6) . . ?
C4 C3 H3A 120.4 . . ?
C2 C3 H3A 120.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C5 C4 C3 122.3(7) . . ?
C5 C4 H4A 118.9 . . ?
C3 C4 H4A 118.9 . . ?
N2 C8 C9 119.4(6) . . ?
N2 C8 C7 118.0(7) . . ?
C9 C8 C7 122.5(7) . . ?
C26 C27 C28 122.0(10) . . ?
C26 C27 H27 119.0 . . ?
C28 C27 H27 119.0 . . ?
C25 C30 C21 121.5(9) . . ?
C25 C30 C29 121.6(9) . . ?
C21 C30 C29 116.9(9) . . ?
C0AA C29 C28 119.0(11) . . ?
C0AA C29 C30 122.9(11) . . ?
C28 C29 C30 118.2(8) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C30 C21 C22 116.6(10) . . ?
C30 C21 C3AA 109.9(11) . . ?
C22 C21 C3AA 133.4(13) . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C27 C26 C25 119.1(11) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C15 C28 C29 118.7(10) . . ?
C15 C28 C27 122.1(10) . . ?
C29 C28 C27 119.2(9) . . ?
C30 C25 C24 121.4(11) . . ?
C30 C25 C26 119.9(9) . . ?
C24 C25 C26 118.4(11) . . ?
C23 C22 C21 120.3(11) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C28 C15 C1AA 119.5(14) . . ?
C28 C15 H15 120.3 . . ?
C1AA C15 H15 120.3 . . ?
C25 C24 C23 119.1(12) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C22 C23 C24 120.8(11) . . ?
C22 C23 H23 119.6 . . ?
C24 C23 H23 119.6 . . ?
C4AA C0AA C2AA 115.2(15) . . ?
C4AA C0AA C29 120.1(17) . . ?
C2AA C0AA C29 123.8(15) . . ?
C0AA C2AA C1AA 118.9(14) . . ?
C0AA C2AA H2AA 120.5 . . ?
C1AA C2AA H2AA 120.5 . . ?
C15 C1AA C2AA 120.0(13) . . ?
C15 C1AA H1AA 120.0 . . ?
C2AA C1AA H1AA 120.0 . . ?
C4AA C3AA C21 129(2) . . ?
C4AA C3AA H3AA 115.7 . . ?
C21 C3AA H3AA 115.7 . . ?
C0AA C4AA C3AA 120(2) . . ?
C0AA C4AA H4AA 119.8 . . ?
C3AA C4AA H4AA 119.8 . . ?
 
_refine_diff_density_max    0.469
_refine_diff_density_min   -0.354
_refine_diff_density_rms    0.071


 
data_14NRES-4DMAP-PYR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C58 H50 N6 O8' 
_chemical_formula_weight          959.04

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    13.337(3)
_cell_length_b                    13.504(3)
_cell_length_c                    16.069(3)
_cell_angle_alpha                 75.831(5)
_cell_angle_beta                  66.422(5)
_cell_angle_gamma                 67.934(5)
_cell_volume                      2442.9(8)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     14998
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       28.2
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.304          
_exptl_crystal_F_000              1008
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.088
_shelx_estimated_absorpt_T_min    0.983
_shelx_estimated_absorpt_T_max    0.983
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.804
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             25588
_diffrn_reflns_av_unetI/netI      0.0914
_diffrn_reflns_av_R_equivalents   0.0621
_diffrn_reflns_limit_h_min        -17
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        -17
_diffrn_reflns_limit_k_max        17
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.069
_diffrn_reflns_theta_max          27.485
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.994
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.994
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.994
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              11144
_reflns_number_gt                 4435
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1128P)²+0.7370P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          11144
_refine_ls_number_parameters      655
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2019
_refine_ls_R_factor_gt            0.0873
_refine_ls_wR_factor_ref          0.2836
_refine_ls_wR_factor_gt           0.2244
_refine_ls_goodness_of_fit_ref    1.039
_refine_ls_restrained_S_all       1.039
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O60 O 0.7180(2) 0.06012(17) 0.31313(16) 0.0517(6) Uani 1 1 d . . . . .
O61 O 0.6864(2) 0.43167(18) 0.27054(18) 0.0576(7) Uani 1 1 d . . . . .
O63 O 0.5142(2) 0.3393(2) 0.37148(19) 0.0691(8) Uani 1 1 d . . . . .
N71 N 0.6024(3) 0.2651(2) 0.3728(2) 0.0485(7) Uani 1 1 d . . . . .
O64 O 0.7690(3) 0.5800(2) 0.18932(18) 0.0692(8) Uani 1 1 d . . . . .
H64 H 0.745616 0.529237 0.218528 0.104 Uiso 1 1 calc R U . . .
O62 O 0.6068(3) 0.2053(2) 0.44286(19) 0.0870(10) Uani 1 1 d . . . . .
O67 O 0.7839(3) 0.9091(2) 0.2175(2) 0.0860(10) Uani 1 1 d . . . . .
H67 H 0.750107 0.958279 0.249942 0.129 Uiso 1 1 calc R U . . .
N72 N 0.7881(3) -0.0097(2) 0.4547(2) 0.0572(8) Uani 1 1 d . . . . .
H72 H 0.747051 0.017688 0.419879 0.069 Uiso 1 1 calc R U . . .
N69 N 0.3246(3) 0.6258(2) 0.0293(2) 0.0590(8) Uani 1 1 d . . . . .
C1 C 0.7020(3) 0.2466(3) 0.2910(2) 0.0414(8) Uani 1 1 d . . . . .
N68 N 0.5099(3) 0.5050(3) 0.2037(2) 0.0628(9) Uani 1 1 d . . . . .
H68 H 0.548226 0.479902 0.240563 0.075 Uiso 1 1 calc R U . . .
C2 C 0.7411(3) 0.3356(3) 0.2427(2) 0.0416(8) Uani 1 1 d . . . . .
C6 C 0.7565(3) 0.1418(3) 0.2641(2) 0.0423(8) Uani 1 1 d . . . . .
N70 N 0.8315(5) 0.7604(4) 0.1113(3) 0.0870(13) Uani 1 1 d . . . . .
N73 N 0.9842(3) -0.1401(3) 0.6204(3) 0.0693(10) Uani 1 1 d . . . . .
C3 C 0.8410(3) 0.3140(3) 0.1655(3) 0.0512(9) Uani 1 1 d . . . . .
H3 H 0.871893 0.368958 0.132502 0.061 Uiso 1 1 calc R U . . .
C8 C 0.7452(3) 0.6500(3) 0.2463(2) 0.0475(9) Uani 1 1 d . . . . .
C7 C 0.7733(3) 0.7439(3) 0.2103(2) 0.0508(9) Uani 1 1 d . . . . .
C5 C 0.8521(3) 0.1282(3) 0.1847(3) 0.0546(10) Uani 1 1 d . . . . .
H5 H 0.888238 0.061300 0.162856 0.066 Uiso 1 1 calc R U . . .
C4 C 0.8941(3) 0.2123(3) 0.1379(3) 0.0543(10) Uani 1 1 d . . . . .
H4 H 0.960115 0.200223 0.086287 0.065 Uiso 1 1 calc R U . . .
C12 C 0.7494(3) 0.8239(3) 0.2615(3) 0.0551(10) Uani 1 1 d . . . . .
C17 C 0.3856(3) 0.5860(3) 0.0856(3) 0.0507(9) Uani 1 1 d . . . . .
C15 C 0.4754(3) 0.6232(3) 0.0764(3) 0.0594(10) Uani 1 1 d . . . . .
H15 H 0.494401 0.676440 0.029670 0.071 Uiso 1 1 calc R U . . .
C21 C 0.7470(4) 0.0177(3) 0.5394(3) 0.0621(11) Uani 1 1 d . . . . .
H21 H 0.673797 0.066837 0.560057 0.075 Uiso 1 1 calc R U . . .
C20 C 0.8927(4) -0.0797(3) 0.4246(3) 0.0630(11) Uani 1 1 d . . . . .
H20 H 0.920355 -0.098197 0.365536 0.076 Uiso 1 1 calc R U . . .
C24 C 0.9206(4) -0.0980(3) 0.5664(3) 0.0547(10) Uani 1 1 d . . . . .
C13 C 0.5343(3) 0.5816(3) 0.1356(3) 0.0613(10) Uani 1 1 d . . . . .
H13 H 0.593350 0.607125 0.128526 0.074 Uiso 1 1 calc R U . . .
C22 C 0.8088(4) -0.0239(3) 0.5955(3) 0.0608(11) Uani 1 1 d . . . . .
H22 H 0.777607 -0.003588 0.654241 0.073 Uiso 1 1 calc R U . . .
C9 C 0.6920(4) 0.6361(3) 0.3395(3) 0.0648(11) Uani 1 1 d . . . . .
H9 H 0.672746 0.573495 0.367077 0.078 Uiso 1 1 calc R U . . .
C11 C 0.6958(4) 0.8070(3) 0.3537(3) 0.0674(12) Uani 1 1 d . . . . .
H11 H 0.678497 0.858666 0.390667 0.081 Uiso 1 1 calc R U . . .
C23 C 0.9609(4) -0.1253(3) 0.4770(3) 0.0640(11) Uani 1 1 d . . . . .
H23 H 1.033636 -0.174073 0.453878 0.077 Uiso 1 1 calc R U . . .
C10 C 0.6672(4) 0.7144(4) 0.3921(3) 0.0735(13) Uani 1 1 d . . . . .
H10 H 0.630380 0.704355 0.454930 0.088 Uiso 1 1 calc R U . . .
C16 C 0.3628(4) 0.5045(3) 0.1589(3) 0.0636(11) Uani 1 1 d . . . . .
H16 H 0.304560 0.476546 0.168535 0.076 Uiso 1 1 calc R U . . .
C14 C 0.4255(4) 0.4680(3) 0.2138(3) 0.0680(12) Uani 1 1 d . . . . .
H14 H 0.409505 0.414506 0.261248 0.082 Uiso 1 1 calc R U . . .
C19 C 0.3476(4) 0.7086(3) -0.0449(3) 0.0700(12) Uani 1 1 d . . . . .
H19A H 0.325939 0.774876 -0.020736 0.105 Uiso 1 1 calc R U . . .
H19B H 0.304007 0.717983 -0.083034 0.105 Uiso 1 1 calc R U . . .
H19C H 0.428292 0.688048 -0.080374 0.105 Uiso 1 1 calc R U . . .
C58 C 0.2295(4) 0.8100(4) 0.2191(4) 0.0800(14) Uani 1 1 d . . . . .
C57 C 0.2657(4) 0.7396(4) 0.2898(4) 0.0797(14) Uani 1 1 d . . . . .
C41 C 0.3115(5) 0.2338(4) 0.2316(4) 0.0864(16) Uani 1 1 d . . . . .
C18 C 0.2284(4) 0.5884(4) 0.0428(3) 0.0812(14) Uani 1 1 d . . . . .
H18A H 0.257227 0.513869 0.033298 0.122 Uiso 1 1 calc R U . . .
H18B H 0.190273 0.629844 0.000003 0.122 Uiso 1 1 calc R U . . .
H18C H 0.174711 0.597070 0.103926 0.122 Uiso 1 1 calc R U . . .
O65 O 0.9323(5) 0.7146(6) 0.0804(3) 0.177(3) Uani 1 1 d . . . . .
C42 C 0.2039(5) 0.3076(4) 0.2650(5) 0.0901(16) Uani 1 1 d . . . . .
C48 C 0.1379(5) 0.8067(5) 0.1978(5) 0.0988(17) Uani 1 1 d . . . . .
C26 C 1.0995(4) -0.2161(4) 0.5898(4) 0.0931(16) Uani 1 1 d . . . . .
H26A H 1.095101 -0.281137 0.579345 0.140 Uiso 1 1 calc R U . . .
H26B H 1.133810 -0.232006 0.635830 0.140 Uiso 1 1 calc R U . . .
H26C H 1.145565 -0.185329 0.534129 0.140 Uiso 1 1 calc R U . . .
O66 O 0.7767(7) 0.8176(4) 0.0666(3) 0.186(3) Uani 1 1 d . . . . .
C27 C 0.3381(8) 0.2142(6) 0.3795(6) 0.116(2) Uani 1 1 d . . . . .
H27 H 0.381314 0.183492 0.417914 0.139 Uiso 1 1 calc R U . . .
C59 C 0.2068(5) 0.6636(4) 0.3404(4) 0.0969(17) Uani 1 1 d . . . . .
C54 C 0.3576(5) 0.7435(5) 0.3108(5) 0.0994(18) Uani 1 1 d . . . . .
C25 C 0.9397(5) -0.1098(4) 0.7124(3) 0.0919(16) Uani 1 1 d . . . . .
H25A H 0.926462 -0.034228 0.709301 0.138 Uiso 1 1 calc R U . . .
H25B H 0.994772 -0.149594 0.742527 0.138 Uiso 1 1 calc R U . . .
H25C H 0.868682 -0.125573 0.746153 0.138 Uiso 1 1 calc R U . . .
C44 C 0.2888(6) 0.8845(5) 0.1660(5) 0.111(2) Uani 1 1 d . . . . .
C29 C 0.1611(7) 0.3349(6) 0.3576(5) 0.1032(18) Uani 1 1 d . . . . .
C36 C 0.3550(8) 0.2048(6) 0.1416(6) 0.111(2) Uani 1 1 d . . . . .
C33 C 0.1297(7) 0.3602(6) 0.2144(6) 0.116(2) Uani 1 1 d . . . . .
C34 C 0.1763(9) 0.3278(7) 0.1198(7) 0.139(3) Uani 1 1 d . . . . .
H34 H 0.131511 0.357688 0.082550 0.167 Uiso 1 1 calc R U . . .
C49 C 0.0815(5) 0.7310(6) 0.2510(6) 0.115(2) Uani 1 1 d . . . . .
H49 H 0.019605 0.728290 0.239438 0.138 Uiso 1 1 calc R U . . .
C50 C 0.1144(6) 0.6634(6) 0.3172(6) 0.115(2) Uani 1 1 d . . . . .
H50 H 0.075628 0.613651 0.349817 0.137 Uiso 1 1 calc R U . . .
C40 C 0.3839(6) 0.1849(5) 0.2867(6) 0.111(2) Uani 1 1 d . . . . .
C56 C 0.3830(7) 0.8853(6) 0.1897(6) 0.130(3) Uani 1 1 d . . . . .
H56 H 0.421563 0.935303 0.157788 0.156 Uiso 1 1 calc R U . . .
C28 C 0.2331(9) 0.2859(7) 0.4086(6) 0.132(3) Uani 1 1 d . . . . .
H28 H 0.206524 0.304084 0.467646 0.158 Uiso 1 1 calc R U . . .
C35 C 0.2821(10) 0.2560(8) 0.0876(6) 0.139(3) Uani 1 1 d . . . . .
H35 H 0.308574 0.239333 0.028116 0.166 Uiso 1 1 calc R U . . .
C37 C 0.4607(9) 0.1330(7) 0.1064(6) 0.141(3) Uani 1 1 d . . . . .
H37 H 0.487662 0.115168 0.047207 0.169 Uiso 1 1 calc R U . . .
C39 C 0.4856(8) 0.1156(7) 0.2551(8) 0.139(3) Uani 1 1 d . . . . .
H39 H 0.530935 0.084703 0.291873 0.167 Uiso 1 1 calc R U . . .
C53 C 0.3889(7) 0.6712(8) 0.3827(6) 0.126(2) Uani 1 1 d . . . . .
H53 H 0.447876 0.672647 0.398838 0.152 Uiso 1 1 calc R U . . .
C45 C 0.2531(9) 0.9546(6) 0.0967(6) 0.151(3) Uani 1 1 d . . . . .
H45 H 0.291196 1.004331 0.062040 0.181 Uiso 1 1 calc R U . . .
C55 C 0.4151(6) 0.8162(7) 0.2560(7) 0.139(3) Uani 1 1 d . . . . .
H55 H 0.478832 0.816566 0.266185 0.167 Uiso 1 1 calc R U . . .
C51 C 0.2425(8) 0.5935(6) 0.4097(5) 0.137(3) Uani 1 1 d . . . . .
H51 H 0.205736 0.542571 0.443446 0.164 Uiso 1 1 calc R U . . .
C32 C 0.0256(8) 0.4308(7) 0.2436(10) 0.161(4) Uani 1 1 d . . . . .
H32 H -0.020091 0.462837 0.207177 0.193 Uiso 1 1 calc R U . . .
C46 C 0.1627(10) 0.9510(7) 0.0792(7) 0.152(4) Uani 1 1 d . . . . .
H46 H 0.139386 1.000050 0.033477 0.183 Uiso 1 1 calc R U . . .
C38 C 0.5283(9) 0.0864(7) 0.1644(9) 0.158(4) Uani 1 1 d . . . . .
H38 H 0.600893 0.036603 0.143037 0.190 Uiso 1 1 calc R U . . .
C47 C 0.1048(7) 0.8780(7) 0.1262(6) 0.129(3) Uani 1 1 d . . . . .
H47 H 0.045293 0.875520 0.111309 0.155 Uiso 1 1 calc R U . . .
C52 C 0.3300(9) 0.5991(8) 0.4279(6) 0.151(3) Uani 1 1 d . . . . .
H52 H 0.351926 0.550592 0.474445 0.181 Uiso 1 1 calc R U . . .
C30 C 0.0562(8) 0.4056(6) 0.3904(7) 0.136(3) Uani 1 1 d . . . . .
H30 H 0.028151 0.422522 0.449934 0.163 Uiso 1 1 calc R U . . .
C31 C -0.0104(10) 0.4536(8) 0.3343(10) 0.173(5) Uani 1 1 d . . . . .
H31 H -0.082376 0.503340 0.357872 0.208 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O60 C6 1.333(4) . ?
O61 C2 1.314(4) . ?
O63 N71 1.230(4) . ?
N71 O62 1.222(4) . ?
N71 C1 1.439(4) . ?
O64 C8 1.343(4) . ?
O64 H64 0.8200 . ?
O67 C12 1.332(4) . ?
O67 H67 0.8200 . ?
N72 C20 1.329(5) . ?
N72 C21 1.338(5) . ?
N72 H72 0.8600 . ?
N69 C17 1.339(5) . ?
N69 C19 1.442(5) . ?
N69 C18 1.470(5) . ?
C1 C6 1.412(4) . ?
C1 C2 1.418(4) . ?
N68 C14 1.334(5) . ?
N68 C13 1.337(5) . ?
N68 H68 0.8600 . ?
C2 C3 1.400(5) . ?
C6 C5 1.386(5) . ?
N70 O66 1.170(6) . ?
N70 O65 1.195(6) . ?
N70 C7 1.467(5) . ?
N73 C24 1.336(5) . ?
N73 C26 1.454(6) . ?
N73 C25 1.456(6) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C8 C9 1.376(5) . ?
C8 C7 1.380(5) . ?
C7 C12 1.383(5) . ?
C5 C4 1.376(5) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C12 C11 1.367(5) . ?
C17 C15 1.408(5) . ?
C17 C16 1.421(5) . ?
C15 C13 1.357(5) . ?
C15 H15 0.9300 . ?
C21 C22 1.344(5) . ?
C21 H21 0.9300 . ?
C20 C23 1.362(5) . ?
C20 H20 0.9300 . ?
C24 C23 1.407(5) . ?
C24 C22 1.412(5) . ?
C13 H13 0.9300 . ?
C22 H22 0.9300 . ?
C9 C10 1.376(5) . ?
C9 H9 0.9300 . ?
C11 C10 1.372(6) . ?
C11 H11 0.9300 . ?
C23 H23 0.9300 . ?
C10 H10 0.9300 . ?
C16 C14 1.338(5) . ?
C16 H16 0.9300 . ?
C14 H14 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C58 C57 1.411(7) . ?
C58 C48 1.413(7) . ?
C58 C44 1.416(8) . ?
C57 C54 1.417(8) . ?
C57 C59 1.421(7) . ?
C41 C42 1.383(8) . ?
C41 C36 1.420(8) . ?
C41 C40 1.439(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C42 C33 1.406(8) . ?
C42 C29 1.451(8) . ?
C48 C49 1.407(9) . ?
C48 C47 1.410(9) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.340(10) . ?
C27 C40 1.460(10) . ?
C27 H27 0.9300 . ?
C59 C51 1.390(9) . ?
C59 C50 1.424(9) . ?
C54 C55 1.389(10) . ?
C54 C53 1.410(9) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C44 C45 1.390(10) . ?
C44 C56 1.455(10) . ?
C29 C30 1.342(9) . ?
C29 C28 1.385(9) . ?
C36 C37 1.361(9) . ?
C36 C35 1.432(9) . ?
C33 C32 1.326(10) . ?
C33 C34 1.501(11) . ?
C34 C35 1.354(11) . ?
C34 H34 0.9300 . ?
C49 C50 1.325(8) . ?
C49 H49 0.9300 . ?
C50 H50 0.9300 . ?
C40 C39 1.305(10) . ?
C56 C55 1.329(10) . ?
C56 H56 0.9300 . ?
C28 H28 0.9300 . ?
C35 H35 0.9300 . ?
C37 C38 1.427(11) . ?
C37 H37 0.9300 . ?
C39 C38 1.433(11) . ?
C39 H39 0.9300 . ?
C53 C52 1.366(11) . ?
C53 H53 0.9300 . ?
C45 C46 1.363(11) . ?
C45 H45 0.9300 . ?
C55 H55 0.9300 . ?
C51 C52 1.343(10) . ?
C51 H51 0.9300 . ?
C32 C31 1.415(13) . ?
C32 H32 0.9300 . ?
C46 C47 1.372(11) . ?
C46 H46 0.9300 . ?
C38 H38 0.9300 . ?
C47 H47 0.9300 . ?
C52 H52 0.9300 . ?
C30 C31 1.393(12) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O62 N71 O63 121.0(3) . . ?
O62 N71 C1 118.9(3) . . ?
O63 N71 C1 120.1(3) . . ?
C8 O64 H64 109.5 . . ?
C12 O67 H67 109.5 . . ?
C20 N72 C21 119.5(3) . . ?
C20 N72 H72 120.2 . . ?
C21 N72 H72 120.2 . . ?
C17 N69 C19 122.0(3) . . ?
C17 N69 C18 120.7(3) . . ?
C19 N69 C18 117.2(3) . . ?
C6 C1 C2 123.7(3) . . ?
C6 C1 N71 118.9(3) . . ?
C2 C1 N71 117.4(3) . . ?
C14 N68 C13 119.2(4) . . ?
C14 N68 H68 120.4 . . ?
C13 N68 H68 120.4 . . ?
O61 C2 C3 123.0(3) . . ?
O61 C2 C1 121.1(3) . . ?
C3 C2 C1 115.9(3) . . ?
O60 C6 C5 121.9(3) . . ?
O60 C6 C1 121.4(3) . . ?
C5 C6 C1 116.7(3) . . ?
O66 N70 O65 123.5(6) . . ?
O66 N70 C7 118.3(6) . . ?
O65 N70 C7 118.2(5) . . ?
C24 N73 C26 121.8(4) . . ?
C24 N73 C25 120.4(4) . . ?
C26 N73 C25 117.8(4) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
O64 C8 C9 124.4(3) . . ?
O64 C8 C7 118.8(3) . . ?
C9 C8 C7 116.8(3) . . ?
C8 C7 C12 124.2(3) . . ?
C8 C7 N70 118.1(3) . . ?
C12 C7 N70 117.7(3) . . ?
C4 C5 C6 120.9(3) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C4 C3 121.8(4) . . ?
C5 C4 H4 119.1 . . ?
C3 C4 H4 119.1 . . ?
O67 C12 C11 125.4(3) . . ?
O67 C12 C7 117.5(3) . . ?
C11 C12 C7 117.0(3) . . ?
N69 C17 C15 122.0(4) . . ?
N69 C17 C16 122.0(4) . . ?
C15 C17 C16 116.0(4) . . ?
C13 C15 C17 120.1(4) . . ?
C13 C15 H15 119.9 . . ?
C17 C15 H15 119.9 . . ?
N72 C21 C22 121.7(4) . . ?
N72 C21 H21 119.2 . . ?
C22 C21 H21 119.2 . . ?
N72 C20 C23 122.4(4) . . ?
N72 C20 H20 118.8 . . ?
C23 C20 H20 118.8 . . ?
N73 C24 C23 121.9(4) . . ?
N73 C24 C22 122.1(4) . . ?
C23 C24 C22 116.0(4) . . ?
N68 C13 C15 121.9(4) . . ?
N68 C13 H13 119.0 . . ?
C15 C13 H13 119.0 . . ?
C21 C22 C24 120.7(4) . . ?
C21 C22 H22 119.6 . . ?
C24 C22 H22 119.6 . . ?
C10 C9 C8 120.2(4) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C12 C11 C10 120.5(4) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C20 C23 C24 119.6(4) . . ?
C20 C23 H23 120.2 . . ?
C24 C23 H23 120.2 . . ?
C11 C10 C9 121.3(4) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C14 C16 C17 119.7(4) . . ?
C14 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
N68 C14 C16 123.0(4) . . ?
N68 C14 H14 118.5 . . ?
C16 C14 H14 118.5 . . ?
N69 C19 H19A 109.5 . . ?
N69 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
N69 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C57 C58 C48 122.2(5) . . ?
C57 C58 C44 119.1(6) . . ?
C48 C58 C44 118.7(7) . . ?
C58 C57 C54 121.9(6) . . ?
C58 C57 C59 118.0(6) . . ?
C54 C57 C59 120.2(6) . . ?
C42 C41 C36 121.3(6) . . ?
C42 C41 C40 120.9(7) . . ?
C36 C41 C40 117.8(7) . . ?
N69 C18 H18A 109.5 . . ?
N69 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N69 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C41 C42 C33 124.0(7) . . ?
C41 C42 C29 120.1(6) . . ?
C33 C42 C29 115.9(7) . . ?
C49 C48 C47 122.1(8) . . ?
C49 C48 C58 117.4(6) . . ?
C47 C48 C58 120.5(7) . . ?
N73 C26 H26A 109.5 . . ?
N73 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N73 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C40 119.2(7) . . ?
C28 C27 H27 120.4 . . ?
C40 C27 H27 120.4 . . ?
C51 C59 C57 118.3(7) . . ?
C51 C59 C50 123.6(7) . . ?
C57 C59 C50 118.1(6) . . ?
C55 C54 C53 123.7(8) . . ?
C55 C54 C57 117.3(7) . . ?
C53 C54 C57 118.9(7) . . ?
N73 C25 H25A 109.5 . . ?
N73 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N73 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C45 C44 C58 119.4(8) . . ?
C45 C44 C56 123.4(8) . . ?
C58 C44 C56 117.1(7) . . ?
C30 C29 C28 122.7(9) . . ?
C30 C29 C42 120.1(8) . . ?
C28 C29 C42 117.2(7) . . ?
C37 C36 C41 122.8(8) . . ?
C37 C36 C35 120.5(10) . . ?
C41 C36 C35 116.7(8) . . ?
C32 C33 C42 126.2(10) . . ?
C32 C33 C34 119.7(9) . . ?
C42 C33 C34 114.1(8) . . ?
C35 C34 C33 121.4(8) . . ?
C35 C34 H34 119.3 . . ?
C33 C34 H34 119.3 . . ?
C50 C49 C48 121.5(7) . . ?
C50 C49 H49 119.2 . . ?
C48 C49 H49 119.2 . . ?
C49 C50 C59 122.7(7) . . ?
C49 C50 H50 118.6 . . ?
C59 C50 H50 118.6 . . ?
C39 C40 C41 120.9(9) . . ?
C39 C40 C27 121.6(9) . . ?
C41 C40 C27 117.5(7) . . ?
C55 C56 C44 121.5(7) . . ?
C55 C56 H56 119.2 . . ?
C44 C56 H56 119.2 . . ?
C27 C28 C29 125.0(8) . . ?
C27 C28 H28 117.5 . . ?
C29 C28 H28 117.5 . . ?
C34 C35 C36 122.5(9) . . ?
C34 C35 H35 118.7 . . ?
C36 C35 H35 118.7 . . ?
C36 C37 C38 117.0(9) . . ?
C36 C37 H37 121.5 . . ?
C38 C37 H37 121.5 . . ?
C40 C39 C38 120.8(9) . . ?
C40 C39 H39 119.6 . . ?
C38 C39 H39 119.6 . . ?
C52 C53 C54 118.1(8) . . ?
C52 C53 H53 120.9 . . ?
C54 C53 H53 120.9 . . ?
C46 C45 C44 120.4(9) . . ?
C46 C45 H45 119.8 . . ?
C44 C45 H45 119.8 . . ?
C56 C55 C54 122.9(8) . . ?
C56 C55 H55 118.5 . . ?
C54 C55 H55 118.5 . . ?
C52 C51 C59 120.1(9) . . ?
C52 C51 H51 119.9 . . ?
C59 C51 H51 119.9 . . ?
C33 C32 C31 114.8(11) . . ?
C33 C32 H32 122.6 . . ?
C31 C32 H32 122.6 . . ?
C45 C46 C47 122.7(10) . . ?
C45 C46 H46 118.7 . . ?
C47 C46 H46 118.7 . . ?
C37 C38 C39 120.7(10) . . ?
C37 C38 H38 119.7 . . ?
C39 C38 H38 119.7 . . ?
C46 C47 C48 118.3(8) . . ?
C46 C47 H47 120.9 . . ?
C48 C47 H47 120.9 . . ?
C51 C52 C53 124.4(9) . . ?
C51 C52 H52 117.8 . . ?
C53 C52 H52 117.8 . . ?
C29 C30 C31 119.5(10) . . ?
C29 C30 H30 120.3 . . ?
C31 C30 H30 120.3 . . ?
C30 C31 C32 123.5(11) . . ?
C30 C31 H31 118.3 . . ?
C32 C31 H31 118.3 . . ?
 
_refine_diff_density_max    0.356
_refine_diff_density_min   -0.253
_refine_diff_density_rms    0.049


 
data_15NRES-TMP-DPE-I
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C40 H46 N8 O8' 
_chemical_formula_weight          766.85

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.5319(7)
_cell_length_b                    8.6425(8)
_cell_length_c                    15.3925(14)
_cell_angle_alpha                 78.729(6)
_cell_angle_beta                  75.782(5)
_cell_angle_gamma                 89.099(6)
_cell_volume                      951.99(15)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     9035
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.5
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.338          
_exptl_crystal_F_000              406
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.095
_shelx_estimated_absorpt_T_min    0.981
_shelx_estimated_absorpt_T_max    0.981
_exptl_absorpt_correction_type    'Multi-scan' 
_exptl_absorpt_correction_T_min   0.887
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9956
_diffrn_reflns_av_unetI/netI      0.0290
_diffrn_reflns_av_R_equivalents   0.0225
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.008
_diffrn_reflns_theta_max          27.485
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.998
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.998
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.998
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4348
_reflns_number_gt                 3565
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0593P)²+0.3903P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4348
_refine_ls_number_parameters      257
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0526
_refine_ls_R_factor_gt            0.0432
_refine_ls_wR_factor_ref          0.1237
_refine_ls_wR_factor_gt           0.1140
_refine_ls_goodness_of_fit_ref    1.066
_refine_ls_restrained_S_all       1.066
_refine_ls_shift/su_max           0.032
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O2 O 0.74232(14) 0.39058(12) 0.11433(7) 0.0209(2) Uani 1 1 d . . . . .
H2 H 0.656114 0.354233 0.100021 0.031 Uiso 1 1 calc R U . . .
O4 O 1.09634(15) 0.60447(14) 0.10504(8) 0.0295(3) Uani 1 1 d . . . . .
O1 O 0.90113(15) 0.72439(14) 0.28963(8) 0.0291(3) Uani 1 1 d . . . . .
H1 H 0.861090 0.783612 0.324982 0.044 Uiso 1 1 calc R U . . .
O3 O 1.05902(15) 0.42111(14) 0.22552(8) 0.0319(3) Uani 1 1 d . . . . .
N4 N 1.00179(16) 0.52678(14) 0.17525(8) 0.0187(3) Uani 1 1 d . . . . .
N2 N 0.79637(17) 0.90020(14) 0.41860(9) 0.0212(3) Uani 1 1 d . . . . .
N3 N 0.70851(17) 1.09154(15) 0.54523(9) 0.0217(3) Uani 1 1 d . . . . .
N1 N 0.47151(17) 0.22009(15) 0.08590(9) 0.0223(3) Uani 1 1 d . . . . .
C2 C 0.80734(18) 0.56332(16) 0.20322(9) 0.0172(3) Uani 1 1 d . . . . .
C3 C 0.7619(2) 0.66648(17) 0.26358(10) 0.0202(3) Uani 1 1 d . . . . .
C1 C 0.67929(19) 0.49019(16) 0.17162(9) 0.0176(3) Uani 1 1 d . . . . .
C6 C 0.4957(2) 0.52497(18) 0.20210(10) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.405532 0.478685 0.182706 0.026 Uiso 1 1 calc R U . . .
C8 C 0.80473(19) 0.84553(17) 0.50524(10) 0.0209(3) Uani 1 1 d . . . . .
C9 C 0.76027(19) 0.94317(18) 0.56908(10) 0.0208(3) Uani 1 1 d . . . . .
C19 C 0.15438(19) 0.08327(18) 0.06372(10) 0.0195(3) Uani 1 1 d . . . . .
C15 C 0.3473(2) 0.30740(18) 0.05113(10) 0.0232(3) Uani 1 1 d . . . . .
H15 H 0.368715 0.416089 0.034077 0.028 Uiso 1 1 calc R U . . .
C17 C 0.2838(2) -0.00883(18) 0.09885(10) 0.0229(3) Uani 1 1 d . . . . .
H17 H 0.266533 -0.117947 0.115558 0.027 Uiso 1 1 calc R U . . .
C4 C 0.5774(2) 0.70031(18) 0.29286(10) 0.0229(3) Uani 1 1 d . . . . .
H4 H 0.541560 0.769534 0.332744 0.028 Uiso 1 1 calc R U . . .
C5 C 0.4486(2) 0.62885(18) 0.26140(11) 0.0235(3) Uani 1 1 d . . . . .
H5 H 0.325796 0.651604 0.280908 0.028 Uiso 1 1 calc R U . . .
C16 C 0.4379(2) 0.06370(19) 0.10860(10) 0.0236(3) Uani 1 1 d . . . . .
H16 H 0.522913 0.000599 0.132177 0.028 Uiso 1 1 calc R U . . .
C13 C 0.74639(19) 1.04844(17) 0.39377(10) 0.0201(3) Uani 1 1 d . . . . .
C12 C 0.70169(19) 1.14479(17) 0.45881(10) 0.0203(3) Uani 1 1 d . . . . .
C18 C 0.1893(2) 0.24508(18) 0.03924(10) 0.0226(3) Uani 1 1 d . . . . .
H18 H 0.107141 0.310915 0.015044 0.027 Uiso 1 1 calc R U . . .
C20 C -0.0153(2) 0.01207(19) 0.04939(10) 0.0225(3) Uani 1 1 d . . . . .
H20A H -0.116916 0.081197 0.062692 0.027 Uiso 1 1 calc R U . . .
H20B H -0.046770 -0.088678 0.091195 0.027 Uiso 1 1 calc R U . . .
C14 C 0.7450(2) 1.1043(2) 0.29547(11) 0.0291(4) Uani 1 1 d . . . . .
H14A H 0.791068 1.023800 0.261646 0.044 Uiso 1 1 calc R U . . .
H14B H 0.821061 1.198464 0.270702 0.044 Uiso 1 1 calc R U . . .
H14C H 0.621835 1.126606 0.291093 0.044 Uiso 1 1 calc R U . . .
C11 C 0.6494(2) 1.31371(18) 0.43376(12) 0.0293(4) Uani 1 1 d . . . . .
H11A H 0.599114 1.353313 0.488462 0.044 Uiso 1 1 calc R U . . .
H11B H 0.559710 1.318830 0.398559 0.044 Uiso 1 1 calc R U . . .
H11C H 0.756146 1.376576 0.398295 0.044 Uiso 1 1 calc R U . . .
C7 C 0.8638(2) 0.67898(19) 0.52806(13) 0.0311(4) Uani 1 1 d . . . . .
H7A H 0.759832 0.607622 0.541623 0.047 Uiso 1 1 calc R U . . .
H7B H 0.914717 0.667003 0.580284 0.047 Uiso 1 1 calc R U . . .
H7C H 0.954621 0.655764 0.476880 0.047 Uiso 1 1 calc R U . . .
C10 C 0.7688(2) 0.8892(2) 0.66667(11) 0.0327(4) Uani 1 1 d . . . . .
H10A H 0.742964 0.975651 0.698146 0.049 Uiso 1 1 calc R U . . .
H10B H 0.889008 0.852494 0.668499 0.049 Uiso 1 1 calc R U . . .
H10C H 0.679746 0.804871 0.695820 0.049 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O2 C1 1.3500(17) . ?
O2 H2 0.8200 . ?
O4 N4 1.2162(16) . ?
O1 C3 1.3465(17) . ?
O1 H1 0.8200 . ?
O3 N4 1.2223(16) . ?
N4 C2 1.4693(18) . ?
N2 C13 1.3391(19) . ?
N2 C8 1.3415(19) . ?
N3 C12 1.3331(19) . ?
N3 C9 1.3423(19) . ?
N1 C16 1.340(2) . ?
N1 C15 1.341(2) . ?
C2 C3 1.390(2) . ?
C2 C1 1.3914(19) . ?
C3 C4 1.397(2) . ?
C1 C6 1.395(2) . ?
C6 C5 1.384(2) . ?
C6 H6 0.9300 . ?
C8 C9 1.394(2) . ?
C8 C7 1.501(2) . ?
C9 C10 1.500(2) . ?
C19 C18 1.387(2) . ?
C19 C17 1.394(2) . ?
C19 C20 1.5090(19) . ?
C15 C18 1.380(2) . ?
C15 H15 0.9300 . ?
C17 C16 1.381(2) . ?
C17 H17 0.9300 . ?
C4 C5 1.387(2) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 H16 0.9300 . ?
C13 C12 1.400(2) . ?
C13 C14 1.498(2) . ?
C12 C11 1.507(2) . ?
C18 H18 0.9300 . ?
C20 C20 1.536(3) 2 ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 O2 H2 109.5 . . ?
C3 O1 H1 109.5 . . ?
O4 N4 O3 124.07(13) . . ?
O4 N4 C2 118.56(12) . . ?
O3 N4 C2 117.36(12) . . ?
C13 N2 C8 119.87(13) . . ?
C12 N3 C9 118.73(13) . . ?
C16 N1 C15 116.70(13) . . ?
C3 C2 C1 123.72(13) . . ?
C3 C2 N4 116.85(12) . . ?
C1 C2 N4 119.38(12) . . ?
O1 C3 C2 116.59(13) . . ?
O1 C3 C4 125.43(13) . . ?
C2 C3 C4 117.97(13) . . ?
O2 C1 C2 117.47(12) . . ?
O2 C1 C6 125.16(13) . . ?
C2 C1 C6 117.37(13) . . ?
C5 C6 C1 119.55(13) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
N2 C8 C9 119.78(13) . . ?
N2 C8 C7 117.04(14) . . ?
C9 C8 C7 123.18(14) . . ?
N3 C9 C8 120.93(13) . . ?
N3 C9 C10 116.87(14) . . ?
C8 C9 C10 122.20(14) . . ?
C18 C19 C17 117.45(13) . . ?
C18 C19 C20 120.28(13) . . ?
C17 C19 C20 122.23(13) . . ?
N1 C15 C18 123.69(14) . . ?
N1 C15 H15 118.2 . . ?
C18 C15 H15 118.2 . . ?
C16 C17 C19 119.28(14) . . ?
C16 C17 H17 120.4 . . ?
C19 C17 H17 120.4 . . ?
C5 C4 C3 118.84(14) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C6 C5 C4 122.54(14) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N1 C16 C17 123.52(14) . . ?
N1 C16 H16 118.2 . . ?
C17 C16 H16 118.2 . . ?
N2 C13 C12 119.62(13) . . ?
N2 C13 C14 117.43(13) . . ?
C12 C13 C14 122.94(14) . . ?
N3 C12 C13 121.07(13) . . ?
N3 C12 C11 117.26(13) . . ?
C13 C12 C11 121.65(14) . . ?
C15 C18 C19 119.34(14) . . ?
C15 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C19 C20 C20 110.92(15) . 2 ?
C19 C20 H20A 109.5 . . ?
C20 C20 H20A 109.5 2 . ?
C19 C20 H20B 109.5 . . ?
C20 C20 H20B 109.5 2 . ?
H20A C20 H20B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
 
_refine_diff_density_max    0.335
_refine_diff_density_min   -0.326
_refine_diff_density_rms    0.053


 
data_16NRES-TMP-22BP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C38 H42 N8 O8' 
_chemical_formula_weight          738.79

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.4104(7)
_cell_length_b                    8.8964(9)
_cell_length_c                    15.7722(15)
_cell_angle_alpha                 95.531(7)
_cell_angle_beta                  101.446(7)
_cell_angle_gamma                 111.676(8)
_cell_volume                      930.47(17)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     8594
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.5
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.318          
_exptl_crystal_F_000              390
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.095
_shelx_estimated_absorpt_T_min    0.981
_shelx_estimated_absorpt_T_max    0.981
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.850
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube' 
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9757
_diffrn_reflns_av_unetI/netI      0.0359
_diffrn_reflns_av_R_equivalents   0.0270
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -20
_diffrn_reflns_limit_l_max        20
_diffrn_reflns_theta_min          3.012
_diffrn_reflns_theta_max          27.481
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.999
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.999
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.999
_reflns_number_total              4270
_reflns_number_gt                 3261
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0713P)²+0.4390P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4270
_refine_ls_number_parameters      248
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0682
_refine_ls_R_factor_gt            0.0517
_refine_ls_wR_factor_ref          0.1503
_refine_ls_wR_factor_gt           0.1371
_refine_ls_goodness_of_fit_ref    1.055
_refine_ls_restrained_S_all       1.055
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.6072(2) 0.54850(19) 0.39526(11) 0.0435(4) Uani 1 1 d . . . . .
O2 O 0.6668(2) 0.75298(18) 0.32810(11) 0.0417(4) Uani 1 1 d . . . . .
O3 O 0.33133(19) 0.37213(15) 0.21274(9) 0.0304(3) Uani 1 1 d . . . . .
H3 H 0.254544 0.297527 0.171892 0.046 Uiso 1 1 calc R U . . .
O4 O 0.36697(18) 0.80485(15) 0.41924(8) 0.0280(3) Uani 1 1 d . . . . .
H4 H 0.300636 0.852008 0.436226 0.042 Uiso 1 1 calc R U . . .
N4 N 0.5521(2) 0.63146(17) 0.34811(9) 0.0228(3) Uani 1 1 d . . . . .
C15 C 0.3358(2) 0.5858(2) 0.31408(11) 0.0204(3) Uani 1 1 d . . . . .
C16 C 0.2297(3) 0.4542(2) 0.24416(11) 0.0221(4) Uani 1 1 d . . . . .
C17 C 0.2482(2) 0.6802(2) 0.35159(11) 0.0214(4) Uani 1 1 d . . . . .
C18 C 0.0265(3) 0.4174(2) 0.20989(12) 0.0261(4) Uani 1 1 d . . . . .
H18 H -0.048787 0.330866 0.162732 0.031 Uiso 1 1 calc R U . . .
C19 C -0.0623(3) 0.5108(2) 0.24662(12) 0.0260(4) Uani 1 1 d . . . . .
H19 H -0.197832 0.485379 0.223393 0.031 Uiso 1 1 calc R U . . .
C20 C 0.0443(3) 0.6404(2) 0.31671(12) 0.0252(4) Uani 1 1 d . . . . .
H20 H -0.019211 0.700573 0.340390 0.030 Uiso 1 1 calc R U . . .
N1 N 0.0879(2) 0.12529(19) 0.07224(10) 0.0289(4) Uani 1 1 d . . . . .
C7 C 0.2525(3) 0.3251(2) -0.01269(15) 0.0401(5) Uani 1 1 d . . . . .
H7A H 0.266513 0.401110 0.038138 0.060 Uiso 1 1 calc R U . . .
H7B H 0.193097 0.354556 -0.064817 0.060 Uiso 1 1 calc R U . . .
H7C H 0.382217 0.328867 -0.015618 0.060 Uiso 1 1 calc R U . . .
C8 C 0.1197(3) 0.1531(2) -0.00606(13) 0.0294(4) Uani 1 1 d . . . . .
C9 C -0.0316(3) -0.0262(2) 0.08106(13) 0.0271(4) Uani 1 1 d . . . . .
C10 C -0.0658(3) -0.0514(3) 0.16873(13) 0.0362(5) Uani 1 1 d . . . . .
H10A H -0.004228 0.052402 0.208802 0.054 Uiso 1 1 calc R U . . .
H10B H -0.007992 -0.125167 0.190118 0.054 Uiso 1 1 calc R U . . .
H10C H -0.207422 -0.097657 0.164242 0.054 Uiso 1 1 calc R U . . .
N2 N 0.5635(2) 1.1208(2) 0.10899(11) 0.0312(4) Uani 1 1 d . . . . .
C1 C 0.4262(3) 0.9491(3) 0.20808(13) 0.0331(4) Uani 1 1 d . . . . .
H1 H 0.413547 0.938380 0.264924 0.040 Uiso 1 1 calc R U . . .
C2 C 0.3378(3) 0.8147(3) 0.14009(14) 0.0377(5) Uani 1 1 d . . . . .
H2 H 0.260065 0.712103 0.150072 0.045 Uiso 1 1 calc R U . . .
C3 C 0.3657(3) 0.8337(2) 0.05689(13) 0.0315(4) Uani 1 1 d . . . . .
H3A H 0.307894 0.744201 0.010436 0.038 Uiso 1 1 calc R U . . .
C4 C 0.4808(2) 0.9877(2) 0.04417(11) 0.0240(4) Uani 1 1 d . . . . .
C5 C 0.5335(3) 1.0991(2) 0.18930(13) 0.0313(4) Uani 1 1 d . . . . .
H5 H 0.588433 1.190728 0.234447 0.038 Uiso 1 1 calc R U . . .
N3 N 0.1436(2) 0.94649(17) 0.48337(9) 0.0216(3) Uani 1 1 d . . . . .
C11 C 0.0386(3) 0.7194(2) 0.56171(14) 0.0334(4) Uani 1 1 d . . . . .
H11A H 0.154265 0.708107 0.548174 0.050 Uiso 1 1 calc R U . . .
H11B H -0.079137 0.622377 0.533187 0.050 Uiso 1 1 calc R U . . .
H11C H 0.054573 0.733242 0.624250 0.050 Uiso 1 1 calc R U . . .
C12 C 0.0171(3) 0.8669(2) 0.52969(11) 0.0223(4) Uani 1 1 d . . . . .
C13 C 0.1294(3) 1.0790(2) 0.45359(11) 0.0221(4) Uani 1 1 d . . . . .
C14 C 0.2786(3) 1.1669(2) 0.40453(13) 0.0307(4) Uani 1 1 d . . . . .
H14A H 0.358103 1.277334 0.436110 0.046 Uiso 1 1 calc R U . . .
H14B H 0.208699 1.169920 0.346960 0.046 Uiso 1 1 calc R U . . .
H14C H 0.364376 1.109819 0.399134 0.046 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 N4 1.213(2) . ?
O2 N4 1.218(2) . ?
O3 C16 1.353(2) . ?
O4 C17 1.349(2) . ?
N4 C15 1.469(2) . ?
C15 C16 1.390(2) . ?
C15 C17 1.392(2) . ?
C16 C18 1.394(2) . ?
C17 C20 1.396(2) . ?
C18 C19 1.386(3) . ?
C19 C20 1.382(3) . ?
N1 C8 1.332(2) . ?
N1 C9 1.350(2) . ?
C7 C8 1.509(3) . ?
C8 C9 1.412(3) 2 ?
C9 C10 1.478(3) . ?
N2 C4 1.344(2) . ?
N2 C5 1.348(2) . ?
C1 C5 1.374(3) . ?
C1 C2 1.380(3) . ?
C2 C3 1.385(3) . ?
C3 C4 1.379(3) . ?
C4 C4 1.497(3) 2_675 ?
N3 C12 1.340(2) . ?
N3 C13 1.342(2) . ?
C11 C12 1.502(2) . ?
C12 C13 1.398(2) 2_576 ?
C13 C14 1.500(2) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O1 N4 O2 123.57(15) . . ?
O1 N4 C15 118.77(15) . . ?
O2 N4 C15 117.65(14) . . ?
C16 C15 C17 123.10(15) . . ?
C16 C15 N4 118.63(14) . . ?
C17 C15 N4 118.23(14) . . ?
O3 C16 C15 117.79(15) . . ?
O3 C16 C18 124.29(15) . . ?
C15 C16 C18 117.91(15) . . ?
O4 C17 C15 117.56(14) . . ?
O4 C17 C20 124.41(15) . . ?
C15 C17 C20 118.03(15) . . ?
C19 C18 C16 119.51(16) . . ?
C20 C19 C18 122.07(16) . . ?
C19 C20 C17 119.37(16) . . ?
C8 N1 C9 120.16(16) . . ?
N1 C8 C9 121.21(18) . 2 ?
N1 C8 C7 118.12(17) . . ?
C9 C8 C7 120.67(18) 2 . ?
N1 C9 C8 118.63(17) . 2 ?
N1 C9 C10 118.49(17) . . ?
C8 C9 C10 122.88(18) 2 . ?
C4 N2 C5 117.49(16) . . ?
C5 C1 C2 118.02(18) . . ?
C1 C2 C3 119.53(19) . . ?
C4 C3 C2 118.79(18) . . ?
N2 C4 C3 122.52(17) . . ?
N2 C4 C4 117.07(19) . 2_675 ?
C3 C4 C4 120.4(2) . 2_675 ?
N2 C5 C1 123.59(18) . . ?
C12 N3 C13 119.53(15) . . ?
N3 C12 C13 120.24(15) . 2_576 ?
N3 C12 C11 117.65(15) . . ?
C13 C12 C11 122.11(16) 2_576 . ?
N3 C13 C12 120.23(16) . 2_576 ?
N3 C13 C14 117.49(15) . . ?
C12 C13 C14 122.27(16) 2_576 . ?
 
_refine_diff_density_max    0.641
_refine_diff_density_min   -0.286
_refine_diff_density_rms    0.054


 
data_17NRE-TMP-22TBP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C22 H23 N3 O4 S2' 
_chemical_formula_weight          457.55

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.6512(11)
_cell_length_b                    8.9495(13)
_cell_length_c                    18.121(3)
_cell_angle_alpha                 87.883(6)
_cell_angle_beta                  78.725(6)
_cell_angle_gamma                 65.728(5)
_cell_volume                      1108.0(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     9432
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.7
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.371          
_exptl_crystal_F_000              480
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.274
_shelx_estimated_absorpt_T_min    0.947
_shelx_estimated_absorpt_T_max    0.947
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.805
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             11118
_diffrn_reflns_av_unetI/netI      0.0504
_diffrn_reflns_av_R_equivalents   0.0385
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.038
_diffrn_reflns_theta_max          27.481
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.995
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.995
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              5059
_reflns_number_gt                 3698
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1022P)²+1.3547P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5059
_refine_ls_number_parameters      286
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0892
_refine_ls_R_factor_gt            0.0671
_refine_ls_wR_factor_ref          0.2055
_refine_ls_wR_factor_gt           0.1878
_refine_ls_goodness_of_fit_ref    1.066
_refine_ls_restrained_S_all       1.066
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S2 S 1.09372(13) -0.15221(11) 0.59467(5) 0.0363(3) Uani 1 1 d . . . . .
S1 S 0.77371(16) 0.24729(13) 1.00457(7) 0.0509(3) Uani 1 1 d . . . . .
O1 O 0.3983(3) 0.3740(3) 0.64814(13) 0.0288(5) Uani 1 1 d . . . . .
H1 H 0.401961 0.314966 0.613782 0.043 Uiso 1 1 calc R U . . .
O2 O -0.0179(3) 0.7223(3) 0.85409(12) 0.0285(5) Uani 1 1 d . . . . .
H2 H -0.129666 0.758699 0.878993 0.043 Uiso 1 1 calc R U . . .
O4 O 0.4648(3) 0.4560(3) 0.79685(15) 0.0378(6) Uani 1 1 d . . . . .
N2 N 0.3433(3) 0.5694(3) 0.77070(13) 0.0195(5) Uani 1 1 d . . . . .
N1 N 0.6362(3) 0.8868(3) 0.94558(13) 0.0184(5) Uani 1 1 d . . . . .
O3 O 0.3512(4) 0.7021(3) 0.76095(17) 0.0431(7) Uani 1 1 d . . . . .
N3 N 0.4442(3) 0.1301(3) 0.55041(13) 0.0219(5) Uani 1 1 d . . . . .
C20 C 1.0204(4) 0.0623(3) 0.89161(16) 0.0204(6) Uani 1 1 d . . . . .
H20 H 1.118317 -0.025764 0.861618 0.024 Uiso 1 1 calc R U . . .
C2 C 0.1796(4) 0.5466(3) 0.75046(15) 0.0171(5) Uani 1 1 d . . . . .
C9 C 0.5137(4) 1.0333(3) 0.92630(16) 0.0197(6) Uani 1 1 d . . . . .
C1 C -0.0056(4) 0.6289(3) 0.79521(16) 0.0196(6) Uani 1 1 d . . . . .
C8 C 0.6242(4) 0.8510(3) 1.01825(15) 0.0187(6) Uani 1 1 d . . . . .
C6 C -0.1620(4) 0.6081(3) 0.77621(16) 0.0214(6) Uani 1 1 d . . . . .
H6 H -0.287371 0.660846 0.804963 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2144(4) 0.4446(3) 0.68839(16) 0.0209(6) Uani 1 1 d . . . . .
C13 C 0.4317(4) 0.1561(4) 0.47811(16) 0.0226(6) Uani 1 1 d . . . . .
C12 C 0.5110(4) -0.0244(4) 0.57306(16) 0.0227(6) Uani 1 1 d . . . . .
C4 C 0.0552(4) 0.4263(4) 0.66999(17) 0.0247(6) Uani 1 1 d . . . . .
H4 H 0.072658 0.359818 0.628518 0.030 Uiso 1 1 calc R U . . .
C5 C -0.1288(4) 0.5080(4) 0.71407(17) 0.0236(6) Uani 1 1 d . . . . .
H5 H -0.234087 0.495167 0.701443 0.028 Uiso 1 1 calc R U . . .
C16 C 0.8646(5) 0.1493(4) 0.58579(18) 0.0286(7) Uani 1 1 d . . . . .
H16 H 0.792347 0.249906 0.567610 0.034 Uiso 1 1 calc R U . . .
C7 C 0.7596(4) 0.6845(4) 1.03695(17) 0.0260(6) Uani 1 1 d . . . . .
H7A H 0.832741 0.619946 0.991235 0.039 Uiso 1 1 calc R U . . .
H7B H 0.684922 0.631526 1.066419 0.039 Uiso 1 1 calc R U . . .
H7C H 0.848053 0.695277 1.065196 0.039 Uiso 1 1 calc R U . . .
C15 C 0.9822(4) 0.0104(4) 0.54077(18) 0.0257(6) Uani 1 1 d . . . . .
C17 C 0.8665(5) 0.1210(4) 0.6639(2) 0.0326(7) Uani 1 1 d . . . . .
H17 H 0.793850 0.201264 0.702255 0.039 Uiso 1 1 calc R U . . .
C10 C 0.5312(5) 1.0644(4) 0.84435(17) 0.0302(7) Uani 1 1 d . . . . .
H10A H 0.636932 0.971850 0.816076 0.045 Uiso 1 1 calc R U . . .
H10B H 0.556333 1.160698 0.835004 0.045 Uiso 1 1 calc R U . . .
H10C H 0.411405 1.080673 0.829204 0.045 Uiso 1 1 calc R U . . .
C18 C 0.9843(5) -0.0340(4) 0.6762(2) 0.0339(7) Uani 1 1 d . . . . .
H18 H 1.003702 -0.072142 0.723678 0.041 Uiso 1 1 calc R U . . .
C11 C 0.5196(5) -0.0479(4) 0.65492(17) 0.0329(7) Uani 1 1 d . . . . .
H11A H 0.490447 0.055316 0.679365 0.049 Uiso 1 1 calc R U . . .
H11B H 0.648268 -0.124784 0.659618 0.049 Uiso 1 1 calc R U . . .
H11C H 0.425508 -0.089300 0.678130 0.049 Uiso 1 1 calc R U . . .
C14 C 0.3532(5) 0.3308(4) 0.4552(2) 0.0363(8) Uani 1 1 d . . . . .
H14A H 0.320684 0.403131 0.498395 0.054 Uiso 1 1 calc R U . . .
H14B H 0.238248 0.354230 0.434975 0.054 Uiso 1 1 calc R U . . .
H14C H 0.450652 0.346831 0.417641 0.054 Uiso 1 1 calc R U . . .
C19 C 0.9611(5) 0.0636(4) 0.9744(2) 0.0327(7) Uani 1 1 d . . . . .
C22 C 0.7748(7) 0.3176(5) 0.9174(3) 0.0617(14) Uani 1 1 d . . . . .
H22 H 0.689373 0.421302 0.906609 0.074 Uiso 1 1 calc R U . . .
C21 C 0.9102(9) 0.2096(7) 0.8658(3) 0.0670(15) Uani 1 1 d . . . . .
H21 H 0.929119 0.232568 0.815078 0.080 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S2 C18 1.705(4) . ?
S2 C15 1.732(3) . ?
S1 C22 1.678(5) . ?
S1 C19 1.697(4) . ?
O1 C3 1.346(3) . ?
O1 H1 0.8200 . ?
O2 C1 1.345(3) . ?
O2 H2 0.8200 . ?
O4 N2 1.216(3) . ?
N2 O3 1.219(3) . ?
N2 C2 1.463(3) . ?
N1 C8 1.338(4) . ?
N1 C9 1.342(4) . ?
N3 C13 1.337(4) . ?
N3 C12 1.342(4) . ?
C20 C21 1.365(6) . ?
C20 C19 1.479(5) . ?
C20 H20 0.9300 . ?
C2 C3 1.389(4) . ?
C2 C1 1.394(4) . ?
C9 C8 1.400(4) 2_677 ?
C9 C10 1.491(4) . ?
C1 C6 1.390(4) . ?
C8 C7 1.497(4) . ?
C6 C5 1.382(4) . ?
C6 H6 0.9300 . ?
C3 C4 1.396(4) . ?
C13 C12 1.392(4) 2_656 ?
C13 C14 1.502(4) . ?
C12 C11 1.501(4) . ?
C4 C5 1.382(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 C15 1.374(4) . ?
C16 C17 1.431(5) . ?
C16 H16 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C15 C15 1.454(6) 2_756 ?
C17 C18 1.347(5) . ?
C17 H17 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C18 H18 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C19 C19 1.446(6) 2_757 ?
C22 C21 1.322(8) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C18 S2 C15 92.07(16) . . ?
C22 S1 C19 93.1(2) . . ?
C3 O1 H1 109.5 . . ?
C1 O2 H2 109.5 . . ?
O4 N2 O3 122.8(3) . . ?
O4 N2 C2 118.9(2) . . ?
O3 N2 C2 118.3(2) . . ?
C8 N1 C9 119.6(2) . . ?
C13 N3 C12 119.1(3) . . ?
C21 C20 C19 109.9(3) . . ?
C21 C20 H20 125.0 . . ?
C19 C20 H20 125.0 . . ?
C3 C2 C1 123.0(3) . . ?
C3 C2 N2 119.1(2) . . ?
C1 C2 N2 117.9(2) . . ?
N1 C9 C8 120.4(3) . 2_677 ?
N1 C9 C10 117.1(2) . . ?
C8 C9 C10 122.5(3) 2_677 . ?
O2 C1 C6 125.1(2) . . ?
O2 C1 C2 116.7(2) . . ?
C6 C1 C2 118.2(3) . . ?
N1 C8 C9 120.0(2) . 2_677 ?
N1 C8 C7 117.8(2) . . ?
C9 C8 C7 122.2(3) 2_677 . ?
C5 C6 C1 119.2(3) . . ?
C5 C6 H6 120.4 . . ?
C1 C6 H6 120.4 . . ?
O1 C3 C2 118.0(2) . . ?
O1 C3 C4 124.0(3) . . ?
C2 C3 C4 117.9(2) . . ?
N3 C13 C12 120.4(3) . 2_656 ?
N3 C13 C14 117.5(3) . . ?
C12 C13 C14 122.1(3) 2_656 . ?
N3 C12 C13 120.5(3) . 2_656 ?
N3 C12 C11 117.4(3) . . ?
C13 C12 C11 122.1(3) 2_656 . ?
C5 C4 C3 119.3(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 122.4(3) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?
C15 C16 C17 112.1(3) . . ?
C15 C16 H16 124.0 . . ?
C17 C16 H16 124.0 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C16 C15 C15 128.5(4) . 2_756 ?
C16 C15 S2 110.7(2) . . ?
C15 C15 S2 120.8(3) 2_756 . ?
C18 C17 C16 113.0(3) . . ?
C18 C17 H17 123.5 . . ?
C16 C17 H17 123.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C17 C18 S2 112.2(3) . . ?
C17 C18 H18 123.9 . . ?
S2 C18 H18 123.9 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C19 C19 C20 129.2(4) 2_757 . ?
C19 C19 S1 122.2(4) 2_757 . ?
C20 C19 S1 108.5(2) . . ?
C21 C22 S1 112.7(3) . . ?
C21 C22 H22 123.6 . . ?
S1 C22 H22 123.6 . . ?
C22 C21 C20 115.7(4) . . ?
C22 C21 H21 122.2 . . ?
C20 C21 H21 122.2 . . ?
 
_refine_diff_density_max    0.929
_refine_diff_density_min   -0.786
_refine_diff_density_rms    0.089


 
data_18NRES-TMP-PYR-ACR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C62 H50 N6 O8' 
_chemical_formula_weight          1007.08

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.6840(18)
_cell_length_b                    9.266(2)
_cell_length_c                    18.043(4)
_cell_angle_alpha                 96.343(7)
_cell_angle_beta                  94.419(7)
_cell_angle_gamma                 107.054(7)
_cell_volume                      1212.6(5)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     8502
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       28.2
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.379          
_exptl_crystal_F_000              528
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.093
_shelx_estimated_absorpt_T_min    0.982
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.600
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             12080
_diffrn_reflns_av_unetI/netI      0.1228
_diffrn_reflns_av_R_equivalents   0.0924
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.023
_diffrn_reflns_theta_max          27.483
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.993
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              5501
_reflns_number_gt                 2857
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1336P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.008(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5501
_refine_ls_number_parameters      348
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1418
_refine_ls_R_factor_gt            0.0855
_refine_ls_wR_factor_ref          0.2544
_refine_ls_wR_factor_gt           0.2084
_refine_ls_goodness_of_fit_ref    0.950
_refine_ls_restrained_S_all       0.950
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C12 C 0.3986(4) -0.0782(4) 0.62510(17) 0.0294(8) Uani 1 1 d . . . . .
H12 H 0.472191 0.000707 0.660698 0.035 Uiso 1 1 calc R U . . .
C4 C 0.1211(5) 0.2104(4) 0.35485(18) 0.0328(8) Uani 1 1 d . . . . .
H4 H 0.073186 0.236607 0.311209 0.039 Uiso 1 1 calc R U . . .
N1 N 0.3446(3) 0.1032(3) 0.54927(13) 0.0231(6) Uani 1 1 d . . . . .
C23 C 0.4342(5) 0.1425(4) 0.85978(18) 0.0332(8) Uani 1 1 d . . . . .
H23 H 0.459398 0.233810 0.839840 0.040 Uiso 1 1 calc R U . . .
O2 O 0.8896(3) 0.6054(3) 0.86315(12) 0.0344(6) Uani 1 1 d . . . . .
H2A H 0.879897 0.676527 0.892198 0.052 Uiso 1 1 calc R U . . .
O1 O 0.6141(3) 0.2941(3) 0.63979(12) 0.0317(6) Uani 1 1 d . . . . .
H1 H 0.516177 0.251094 0.613858 0.048 Uiso 1 1 calc R U . . .
N3 N 0.9075(3) 0.4172(3) 0.73826(13) 0.0249(6) Uani 1 1 d . . . . .
C28 C -0.1367(5) -0.0178(4) 0.84754(17) 0.0352(8) Uani 1 1 d . . . . .
H28A H -0.173519 -0.122267 0.824530 0.053 Uiso 1 1 calc R U . . .
H28B H -0.043804 0.042202 0.821257 0.053 Uiso 1 1 calc R U . . .
H28C H -0.240661 0.019725 0.845378 0.053 Uiso 1 1 calc R U . . .
C31 C 0.0661(5) 0.2799(4) 0.94073(18) 0.0361(8) Uani 1 1 d . . . . .
H31A H 0.117229 0.362262 0.980953 0.054 Uiso 1 1 calc R U . . .
H31B H -0.046056 0.288971 0.917377 0.054 Uiso 1 1 calc R U . . .
H31C H 0.151463 0.283702 0.904306 0.054 Uiso 1 1 calc R U . . .
N2 N -0.0884(3) -0.1366(3) 0.95681(14) 0.0281(6) Uani 1 1 d . . . . .
C5 C 0.0873(4) 0.0624(4) 0.36312(17) 0.0311(8) Uani 1 1 d . . . . .
H5 H 0.015253 -0.012216 0.325228 0.037 Uiso 1 1 calc R U . . .
O3 O 1.0112(3) 0.5027(3) 0.70384(15) 0.0510(8) Uani 1 1 d . . . . .
O4 O 0.9380(3) 0.3068(3) 0.75920(15) 0.0472(7) Uani 1 1 d . . . . .
C13 C 0.3170(4) -0.0428(4) 0.55916(16) 0.0241(7) Uani 1 1 d . . . . .
C27 C 0.4649(4) 0.0021(4) 0.96269(16) 0.0248(7) Uani 1 1 d . . . . .
C7 C 0.1316(4) -0.1305(4) 0.43997(16) 0.0256(7) Uani 1 1 d . . . . .
H7 H 0.059828 -0.208483 0.403479 0.031 Uiso 1 1 calc R U . . .
C30 C 0.0283(4) 0.1321(4) 0.97105(16) 0.0270(7) Uani 1 1 d . . . . .
C29 C -0.0624(4) -0.0071(4) 0.92751(17) 0.0267(7) Uani 1 1 d . . . . .
C22 C 0.5044(4) 0.1417(4) 0.93314(17) 0.0274(7) Uani 1 1 d . . . . .
C19 C 0.5855(4) 0.3765(3) 0.70048(16) 0.0236(7) Uani 1 1 d . . . . .
C1 C 0.2699(4) 0.1364(4) 0.48630(17) 0.0246(7) Uani 1 1 d . . . . .
C9 C 0.1869(4) -0.3169(4) 0.51880(18) 0.0307(8) Uani 1 1 d . . . . .
H9 H 0.118181 -0.398006 0.483194 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2082(4) -0.1667(4) 0.50465(17) 0.0251(7) Uani 1 1 d . . . . .
C18 C 0.4211(4) 0.4007(4) 0.71390(17) 0.0276(7) Uani 1 1 d . . . . .
H18 H 0.316017 0.354034 0.680521 0.033 Uiso 1 1 calc R U . . .
C6 C 0.1596(4) 0.0185(4) 0.42869(16) 0.0247(7) Uani 1 1 d . . . . .
C2 C 0.3011(4) 0.2905(4) 0.47550(18) 0.0284(7) Uani 1 1 d . . . . .
H2 H 0.371873 0.367865 0.512493 0.034 Uiso 1 1 calc R U . . .
C11 C 0.3724(5) -0.2223(4) 0.63741(18) 0.0348(8) Uani 1 1 d . . . . .
H11 H 0.425175 -0.242226 0.681754 0.042 Uiso 1 1 calc R U . . .
C14 C 0.7368(4) 0.4466(3) 0.75300(16) 0.0217(7) Uani 1 1 d . . . . .
C3 C 0.2289(5) 0.3264(4) 0.41188(18) 0.0306(8) Uani 1 1 d . . . . .
H3 H 0.250277 0.428119 0.405568 0.037 Uiso 1 1 calc R U . . .
C15 C 0.7318(4) 0.5427(3) 0.81698(16) 0.0261(7) Uani 1 1 d . . . . .
C26 C 0.3542(4) -0.1348(4) 0.91779(17) 0.0285(7) Uani 1 1 d . . . . .
C17 C 0.4155(5) 0.4958(4) 0.77792(18) 0.0309(8) Uani 1 1 d . . . . .
H17 H 0.304575 0.511924 0.786842 0.037 Uiso 1 1 calc R U . . .
C25 C 0.2879(4) -0.1268(4) 0.84461(17) 0.0323(8) Uani 1 1 d . . . . .
H25 H 0.215534 -0.215379 0.814509 0.039 Uiso 1 1 calc R U . . .
C10 C 0.2642(5) -0.3454(4) 0.58304(19) 0.0359(8) Uani 1 1 d . . . . .
H10 H 0.246834 -0.445483 0.591775 0.043 Uiso 1 1 calc R U . . .
C16 C 0.5679(4) 0.5676(4) 0.82901(17) 0.0296(8) Uani 1 1 d . . . . .
H16 H 0.559735 0.632003 0.871055 0.036 Uiso 1 1 calc R U . . .
C20 C 0.6839(4) 0.2734(4) 1.05002(19) 0.0330(8) Uani 1 1 d . . . . .
H20 H 0.757635 0.363433 1.078588 0.040 Uiso 1 1 calc R U . . .
C21 C 0.6163(5) 0.2772(4) 0.97978(19) 0.0331(8) Uani 1 1 d . . . . .
H21 H 0.642640 0.369797 0.960994 0.040 Uiso 1 1 calc R U . . .
C24 C 0.3273(5) 0.0089(4) 0.81623(18) 0.0356(8) Uani 1 1 d . . . . .
H24 H 0.281728 0.011148 0.767246 0.043 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C12 C11 1.337(5) . ?
C12 C13 1.417(4) . ?
C4 C5 1.346(5) . ?
C4 C3 1.415(5) . ?
N1 C1 1.340(4) . ?
N1 C13 1.341(4) . ?
C23 C24 1.384(5) . ?
C23 C22 1.392(4) . ?
O2 C15 1.351(3) . ?
O1 C19 1.335(3) . ?
N3 O4 1.207(3) . ?
N3 O3 1.210(3) . ?
N3 C14 1.454(4) . ?
C28 C29 1.492(4) . ?
C31 C30 1.488(4) . ?
N2 C29 1.332(4) . ?
N2 C30 1.339(4) 2_557 ?
C5 C6 1.418(4) . ?
C13 C8 1.430(4) . ?
C27 C22 1.412(4) . ?
C27 C27 1.420(6) 2_657 ?
C27 C26 1.422(4) . ?
C7 C6 1.375(4) . ?
C7 C8 1.385(4) . ?
C30 C29 1.390(4) . ?
C22 C21 1.431(5) . ?
C19 C18 1.380(4) . ?
C19 C14 1.387(4) . ?
C1 C2 1.415(4) . ?
C1 C6 1.436(4) . ?
C9 C10 1.349(5) . ?
C9 C8 1.407(4) . ?
C18 C17 1.385(4) . ?
C2 C3 1.353(4) . ?
C11 C10 1.423(5) . ?
C14 C15 1.388(4) . ?
C15 C16 1.374(4) . ?
C26 C25 1.396(4) . ?
C26 C20 1.430(4) 2_657 ?
C17 C16 1.380(4) . ?
C25 C24 1.370(5) . ?
C20 C21 1.340(5) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C11 C12 C13 121.6(3) . . ?
C5 C4 C3 120.7(3) . . ?
C1 N1 C13 119.8(3) . . ?
C24 C23 C22 120.7(3) . . ?
O4 N3 O3 122.7(3) . . ?
O4 N3 C14 118.8(3) . . ?
O3 N3 C14 118.4(3) . . ?
C29 N2 C30 119.7(3) . 2_557 ?
C4 C5 C6 121.1(3) . . ?
N1 C13 C12 119.9(3) . . ?
N1 C13 C8 122.2(3) . . ?
C12 C13 C8 117.9(3) . . ?
C22 C27 C27 120.2(4) . 2_657 ?
C22 C27 C26 120.0(3) . . ?
C27 C27 C26 119.7(4) 2_657 . ?
C6 C7 C8 121.2(3) . . ?
N2 C30 C29 119.9(3) 2_557 . ?
N2 C30 C31 117.3(3) 2_557 . ?
C29 C30 C31 122.8(3) . . ?
N2 C29 C30 120.5(3) . . ?
N2 C29 C28 117.6(3) . . ?
C30 C29 C28 121.9(3) . . ?
C23 C22 C27 119.0(3) . . ?
C23 C22 C21 122.3(3) . . ?
C27 C22 C21 118.6(3) . . ?
O1 C19 C18 125.7(3) . . ?
O1 C19 C14 116.3(3) . . ?
C18 C19 C14 118.0(3) . . ?
N1 C1 C2 119.7(3) . . ?
N1 C1 C6 121.4(3) . . ?
C2 C1 C6 118.9(3) . . ?
C10 C9 C8 121.3(3) . . ?
C7 C8 C9 123.8(3) . . ?
C7 C8 C13 117.3(3) . . ?
C9 C8 C13 118.9(3) . . ?
C19 C18 C17 118.9(3) . . ?
C7 C6 C5 123.7(3) . . ?
C7 C6 C1 118.1(3) . . ?
C5 C6 C1 118.2(3) . . ?
C3 C2 C1 120.6(3) . . ?
C12 C11 C10 120.4(3) . . ?
C19 C14 C15 123.2(3) . . ?
C19 C14 N3 117.0(3) . . ?
C15 C14 N3 119.8(3) . . ?
C2 C3 C4 120.6(3) . . ?
O2 C15 C16 124.6(3) . . ?
O2 C15 C14 117.3(3) . . ?
C16 C15 C14 118.1(3) . . ?
C25 C26 C27 118.3(3) . . ?
C25 C26 C20 123.3(3) . 2_657 ?
C27 C26 C20 118.3(3) . 2_657 ?
C16 C17 C18 122.6(3) . . ?
C24 C25 C26 121.3(3) . . ?
C9 C10 C11 119.9(3) . . ?
C15 C16 C17 119.2(3) . . ?
C21 C20 C26 121.8(3) . 2_657 ?
C20 C21 C22 121.3(3) . . ?
C25 C24 C23 120.6(3) . . ?
 
_refine_diff_density_max    0.601
_refine_diff_density_min   -0.525
_refine_diff_density_rms    0.113


 
data_19NTES-TMP-PYR-4DMAP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C50 H52 N8 O8' 
_chemical_formula_weight          892.99

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.7634(12)
_cell_length_b                    8.9486(14)
_cell_length_c                    16.368(3)
_cell_angle_alpha                 83.021(6)
_cell_angle_beta                  82.842(6)
_cell_angle_gamma                 88.111(6)
_cell_volume                      1119.7(3)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     9566
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       27.7
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.324          
_exptl_crystal_F_000              472
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.091
_shelx_estimated_absorpt_T_min    0.982
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.764
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             11576
_diffrn_reflns_av_unetI/netI      0.0516
_diffrn_reflns_av_R_equivalents   0.0397
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -21
_diffrn_reflns_limit_l_max        21
_diffrn_reflns_theta_min          3.067
_diffrn_reflns_theta_max          27.482
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              5114
_reflns_number_gt                 3585
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0718P)²+1.6202P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.005(2)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          5114
_refine_ls_number_parameters      305
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0865
_refine_ls_R_factor_gt            0.0630
_refine_ls_wR_factor_ref          0.2061
_refine_ls_wR_factor_gt           0.1944
_refine_ls_goodness_of_fit_ref    1.105
_refine_ls_restrained_S_all       1.105
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O4 O 0.9664(3) 0.6218(2) 0.35641(14) 0.0311(5) Uani 1 1 d . . . . .
H4 H 1.040209 0.668948 0.373751 0.047 Uiso 1 1 calc R U . . .
N1 N 0.7532(3) 0.4694(3) 0.27859(14) 0.0226(5) Uani 1 1 d . . . . .
O3 O 0.8895(3) 0.2465(2) 0.18933(14) 0.0322(5) Uani 1 1 d . . . . .
H3 H 0.941730 0.197163 0.154721 0.048 Uiso 1 1 calc R U . . .
C14 C 1.4707(3) 0.9246(3) 0.00892(17) 0.0227(6) Uani 1 1 d . . . . .
C5 C 1.2219(4) 0.4850(3) 0.30280(18) 0.0252(6) Uani 1 1 d . . . . .
H5 H 1.296170 0.537553 0.328934 0.030 Uiso 1 1 calc R U . . .
C1 C 0.9398(3) 0.4334(3) 0.27193(16) 0.0212(5) Uani 1 1 d . . . . .
O1 O 0.6651(3) 0.4366(3) 0.34456(14) 0.0428(6) Uani 1 1 d . . . . .
O2 O 0.6945(3) 0.5323(3) 0.21745(16) 0.0487(7) Uani 1 1 d . . . . .
C3 C 1.1821(4) 0.2929(3) 0.21445(18) 0.0276(6) Uani 1 1 d . . . . .
H3A H 1.229767 0.219142 0.182549 0.033 Uiso 1 1 calc R U . . .
C8 C 1.4317(4) 0.8451(3) -0.05669(19) 0.0282(6) Uani 1 1 d . . . . .
C2 C 1.0039(4) 0.3222(3) 0.22311(17) 0.0236(6) Uani 1 1 d . . . . .
C12 C 1.4501(4) 0.8543(3) 0.09164(18) 0.0272(6) Uani 1 1 d . . . . .
C6 C 1.0438(4) 0.5165(3) 0.31258(16) 0.0226(6) Uani 1 1 d . . . . .
C4 C 1.2877(4) 0.3754(3) 0.25409(18) 0.0276(6) Uani 1 1 d . . . . .
H4A H 1.406764 0.356307 0.247698 0.033 Uiso 1 1 calc R U . . .
C7 C 1.4527(4) 0.9207(4) -0.13959(19) 0.0331(7) Uani 1 1 d . . . . .
H7 H 1.426328 0.870442 -0.182823 0.040 Uiso 1 1 calc R U . . .
C13 C 1.4904(4) 0.9375(4) 0.15622(19) 0.0333(7) Uani 1 1 d . . . . .
H13 H 1.476793 0.892173 0.210804 0.040 Uiso 1 1 calc R U . . .
C11 C 1.3931(4) 0.7051(4) 0.1068(2) 0.0353(7) Uani 1 1 d . . . . .
H11 H 1.379326 0.657217 0.160878 0.042 Uiso 1 1 calc R U . . .
C9 C 1.3749(4) 0.6968(4) -0.0375(2) 0.0373(8) Uani 1 1 d . . . . .
H9 H 1.348593 0.643525 -0.079647 0.045 Uiso 1 1 calc R U . . .
C10 C 1.3574(4) 0.6287(4) 0.0434(2) 0.0409(8) Uani 1 1 d . . . . .
H10 H 1.320935 0.529597 0.054945 0.049 Uiso 1 1 calc R U . . .
N2 N 0.0153(3) 0.0765(3) 0.06661(14) 0.0235(5) Uani 1 1 d . . . . .
C17 C -0.0266(3) -0.0691(3) 0.07848(17) 0.0224(6) Uani 1 1 d . . . . .
C16 C 0.0430(3) 0.1466(3) -0.01085(17) 0.0228(6) Uani 1 1 d . . . . .
C18 C -0.0504(4) -0.1448(3) 0.16599(18) 0.0324(7) Uani 1 1 d . . . . .
H18A H 0.039526 -0.219640 0.173301 0.049 Uiso 1 1 calc R U . . .
H18B H -0.161592 -0.191865 0.177063 0.049 Uiso 1 1 calc R U . . .
H18C H -0.044489 -0.071213 0.203585 0.049 Uiso 1 1 calc R U . . .
C15 C 0.0957(4) 0.3082(3) -0.0211(2) 0.0319(7) Uani 1 1 d . . . . .
H15A H 0.067804 0.348953 0.030636 0.048 Uiso 1 1 calc R U . . .
H15B H 0.034574 0.364627 -0.062572 0.048 Uiso 1 1 calc R U . . .
H15C H 0.218437 0.314497 -0.037994 0.048 Uiso 1 1 calc R U . . .
N3 N 0.1487(3) 0.8039(3) 0.41817(17) 0.0341(6) Uani 1 1 d . . . . .
N4 N 0.3087(3) 1.1481(3) 0.54141(15) 0.0284(5) Uani 1 1 d . . . . .
C23 C 0.2588(3) 1.0356(3) 0.50138(17) 0.0243(6) Uani 1 1 d . . . . .
C22 C 0.2488(4) 0.8856(3) 0.53792(19) 0.0299(6) Uani 1 1 d . . . . .
H22 H 0.279286 0.859630 0.591049 0.036 Uiso 1 1 calc R U . . .
C25 C 0.3480(4) 1.1189(4) 0.62660(19) 0.0344(7) Uani 1 1 d . . . . .
H25A H 0.251559 1.070105 0.660726 0.052 Uiso 1 1 calc R U . . .
H25B H 0.368849 1.212455 0.646552 0.052 Uiso 1 1 calc R U . . .
H25C H 0.449529 1.055056 0.628717 0.052 Uiso 1 1 calc R U . . .
C21 C 0.2136(4) 1.0639(3) 0.42001(18) 0.0295(6) Uani 1 1 d . . . . .
H21 H 0.220125 1.160708 0.391909 0.035 Uiso 1 1 calc R U . . .
C20 C 0.1939(4) 0.7771(3) 0.4950(2) 0.0321(7) Uani 1 1 d . . . . .
H20 H 0.187586 0.678755 0.521010 0.039 Uiso 1 1 calc R U . . .
C24 C 0.3248(4) 1.3006(3) 0.4999(2) 0.0339(7) Uani 1 1 d . . . . .
H24A H 0.403275 1.300921 0.449724 0.051 Uiso 1 1 calc R U . . .
H24B H 0.368797 1.363717 0.535728 0.051 Uiso 1 1 calc R U . . .
H24C H 0.212958 1.338187 0.486920 0.051 Uiso 1 1 calc R U . . .
C19 C 0.1598(4) 0.9472(4) 0.38265(19) 0.0327(7) Uani 1 1 d . . . . .
H19 H 0.129024 0.968814 0.329300 0.039 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O4 C6 1.336(3) . ?
N1 O1 1.213(3) . ?
N1 O2 1.219(3) . ?
N1 C1 1.467(3) . ?
O3 C2 1.344(3) . ?
C14 C12 1.414(4) . ?
C14 C14 1.423(5) 2_875 ?
C14 C8 1.426(4) . ?
C5 C4 1.383(4) . ?
C5 C6 1.395(4) . ?
C1 C2 1.392(4) . ?
C1 C6 1.393(4) . ?
C3 C4 1.388(4) . ?
C3 C2 1.393(4) . ?
C8 C9 1.399(4) . ?
C8 C7 1.433(4) . ?
C12 C11 1.404(4) . ?
C12 C13 1.434(4) . ?
C7 C13 1.342(5) 2_875 ?
C11 C10 1.371(5) . ?
C9 C10 1.381(5) . ?
N2 C17 1.338(4) . ?
N2 C16 1.340(4) . ?
C17 C16 1.396(4) 2 ?
C17 C18 1.500(4) . ?
C16 C15 1.500(4) . ?
N3 C20 1.340(4) . ?
N3 C19 1.343(4) . ?
N4 C23 1.357(4) . ?
N4 C24 1.451(4) . ?
N4 C25 1.455(4) . ?
C23 C22 1.402(4) . ?
C23 C21 1.411(4) . ?
C22 C20 1.372(4) . ?
C21 C19 1.374(4) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O1 N1 O2 123.1(2) . . ?
O1 N1 C1 118.7(2) . . ?
O2 N1 C1 118.1(2) . . ?
C12 C14 C14 120.0(3) . 2_875 ?
C12 C14 C8 120.2(3) . . ?
C14 C14 C8 119.8(3) 2_875 . ?
C4 C5 C6 119.8(3) . . ?
C2 C1 C6 123.7(2) . . ?
C2 C1 N1 118.3(2) . . ?
C6 C1 N1 117.9(2) . . ?
C4 C3 C2 119.1(3) . . ?
C9 C8 C14 118.7(3) . . ?
C9 C8 C7 122.8(3) . . ?
C14 C8 C7 118.5(3) . . ?
O3 C2 C1 118.0(2) . . ?
O3 C2 C3 124.0(2) . . ?
C1 C2 C3 117.9(3) . . ?
C11 C12 C14 118.4(3) . . ?
C11 C12 C13 122.8(3) . . ?
C14 C12 C13 118.8(3) . . ?
O4 C6 C1 117.8(2) . . ?
O4 C6 C5 125.1(2) . . ?
C1 C6 C5 117.2(2) . . ?
C5 C4 C3 122.3(3) . . ?
C13 C7 C8 121.5(3) 2_875 . ?
C7 C13 C12 121.4(3) 2_875 . ?
C10 C11 C12 121.1(3) . . ?
C10 C9 C8 120.6(3) . . ?
C11 C10 C9 121.0(3) . . ?
C17 N2 C16 119.3(2) . . ?
N2 C17 C16 120.3(2) . 2 ?
N2 C17 C18 117.6(2) . . ?
C16 C17 C18 122.1(3) 2 . ?
N2 C16 C17 120.4(2) . 2 ?
N2 C16 C15 117.3(2) . . ?
C17 C16 C15 122.3(3) 2 . ?
C20 N3 C19 116.2(3) . . ?
C23 N4 C24 120.6(2) . . ?
C23 N4 C25 121.0(3) . . ?
C24 N4 C25 118.4(2) . . ?
N4 C23 C22 122.4(3) . . ?
N4 C23 C21 121.4(3) . . ?
C22 C23 C21 116.1(3) . . ?
C20 C22 C23 119.8(3) . . ?
C19 C21 C23 119.4(3) . . ?
N3 C20 C22 124.2(3) . . ?
N3 C19 C21 124.2(3) . . ?
 
_refine_diff_density_max    0.501
_refine_diff_density_min   -0.344
_refine_diff_density_rms    0.073


 
data_20NRES-TMP-22BP-DPE-I
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C42 H42 N8 O8' 
_chemical_formula_weight          786.83

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.5543(17)
_cell_length_b                    8.914(2)
_cell_length_c                    14.713(3)
_cell_angle_alpha                 85.797(7)
_cell_angle_beta                  88.497(6)
_cell_angle_gamma                 89.487(6)
_cell_volume                      987.7(4)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     7266
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.323          
_exptl_crystal_F_000              414
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.094
_shelx_estimated_absorpt_T_min    0.981
_shelx_estimated_absorpt_T_max    0.981
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.772
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             10148
_diffrn_reflns_av_unetI/netI      0.0584
_diffrn_reflns_av_R_equivalents   0.0425
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        19
_diffrn_reflns_theta_min          3.002
_diffrn_reflns_theta_max          27.484
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.995
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.995
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.995
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4515
_reflns_number_gt                 2412
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0952P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4515
_refine_ls_number_parameters      264
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1221
_refine_ls_R_factor_gt            0.0629
_refine_ls_wR_factor_ref          0.1925
_refine_ls_wR_factor_gt           0.1624
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_restrained_S_all       1.032
_refine_ls_shift/su_max           0.027
_refine_ls_shift/su_mean          0.002
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O2 O 0.1600(2) 0.37317(19) 0.11278(11) 0.0614(5) Uani 1 1 d . . . . .
H2 H 0.254062 0.331732 0.100473 0.092 Uiso 1 1 calc R U . . .
O1 O -0.0942(2) 0.7499(2) 0.27973(12) 0.0677(6) Uani 1 1 d . . . . .
H1 H -0.071858 0.814464 0.314610 0.102 Uiso 1 1 calc R U . . .
N4 N -0.1307(3) 0.5315(2) 0.16364(13) 0.0453(5) Uani 1 1 d . . . . .
N1 N -0.0334(3) 0.9191(2) 0.42699(13) 0.0489(5) Uani 1 1 d . . . . .
O3 O -0.1949(3) 0.6154(2) 0.10577(15) 0.0842(7) Uani 1 1 d . . . . .
N2 N 0.4546(3) 0.2088(2) 0.07952(14) 0.0559(6) Uani 1 1 d . . . . .
O4 O -0.2040(3) 0.4208(3) 0.19732(16) 0.0852(7) Uani 1 1 d . . . . .
N3 N 0.5702(3) 0.1811(2) 0.53041(14) 0.0585(6) Uani 1 1 d . . . . .
C2 C 0.0444(3) 0.5674(2) 0.19581(13) 0.0381(5) Uani 1 1 d . . . . .
C3 C 0.1897(3) 0.4842(2) 0.16750(14) 0.0426(6) Uani 1 1 d . . . . .
C1 C 0.0578(3) 0.6813(3) 0.25424(15) 0.0477(6) Uani 1 1 d . . . . .
C21 C 0.5280(3) 0.0723(3) 0.47670(15) 0.0452(6) Uani 1 1 d . . . . .
C15 C 0.7913(3) 0.0807(3) 0.05792(16) 0.0510(6) Uani 1 1 d . . . . .
C9 C 0.0225(3) 1.0620(3) 0.41331(16) 0.0469(6) Uani 1 1 d . . . . .
C8 C -0.0562(3) 0.8566(2) 0.51181(17) 0.0487(6) Uani 1 1 d . . . . .
C13 C 0.6599(4) 0.0086(3) 0.10983(17) 0.0564(7) Uani 1 1 d . . . . .
H13 H 0.681623 -0.085788 0.138799 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3550(3) 0.5233(3) 0.19673(17) 0.0543(7) Uani 1 1 d . . . . .
H4 H 0.455705 0.471716 0.178294 0.065 Uiso 1 1 calc R U . . .
C6 C 0.2240(4) 0.7181(3) 0.28279(18) 0.0607(7) Uani 1 1 d . . . . .
H6 H 0.237432 0.795123 0.321363 0.073 Uiso 1 1 calc R U . . .
C5 C 0.3692(4) 0.6389(3) 0.25317(18) 0.0605(7) Uani 1 1 d . . . . .
H5 H 0.480853 0.664467 0.271979 0.073 Uiso 1 1 calc R U . . .
C20 C 0.5357(4) 0.0945(3) 0.38258(17) 0.0573(7) Uani 1 1 d . . . . .
H20 H 0.507225 0.016978 0.346712 0.069 Uiso 1 1 calc R U . . .
C11 C 0.4966(4) 0.0749(3) 0.11920(17) 0.0588(7) Uani 1 1 d . . . . .
H11 H 0.410637 0.023422 0.155247 0.071 Uiso 1 1 calc R U . . .
C16 C 0.9742(4) 0.0151(3) 0.04730(18) 0.0656(8) Uani 1 1 d . . . . .
H16A H 1.058883 0.084016 0.069508 0.079 Uiso 1 1 calc R U . . .
H16B H 0.981071 -0.078259 0.085312 0.079 Uiso 1 1 calc R U . . .
C14 C 0.7471(4) 0.2181(3) 0.0162(2) 0.0692(8) Uani 1 1 d . . . . .
H14 H 0.830182 0.271278 -0.020806 0.083 Uiso 1 1 calc R U . . .
C18 C 0.6284(4) 0.3442(3) 0.3971(2) 0.0672(8) Uani 1 1 d . . . . .
H18 H 0.662858 0.438368 0.371579 0.081 Uiso 1 1 calc R U . . .
C17 C 0.6191(4) 0.3141(3) 0.4892(2) 0.0669(8) Uani 1 1 d . . . . .
H17 H 0.648378 0.390453 0.525743 0.080 Uiso 1 1 calc R U . . .
C12 C 0.5805(4) 0.2775(3) 0.0290(2) 0.0694(8) Uani 1 1 d . . . . .
H12 H 0.555202 0.371434 0.000301 0.083 Uiso 1 1 calc R U . . .
C19 C 0.5855(4) 0.2314(3) 0.34296(19) 0.0687(8) Uani 1 1 d . . . . .
H19 H 0.590348 0.248188 0.279808 0.082 Uiso 1 1 calc R U . . .
C10 C 0.0461(4) 1.1256(3) 0.31701(18) 0.0723(8) Uani 1 1 d . . . . .
H10A H -0.011855 1.062217 0.277117 0.108 Uiso 1 1 calc R U . . .
H10B H 0.170090 1.130590 0.301141 0.108 Uiso 1 1 calc R U . . .
H10C H -0.004745 1.224772 0.310887 0.108 Uiso 1 1 calc R U . . .
C7 C -0.1188(4) 0.6964(3) 0.5224(2) 0.0729(9) Uani 1 1 d . . . . .
H7A H -0.137476 0.661082 0.463346 0.109 Uiso 1 1 calc R U . . .
H7B H -0.227874 0.691294 0.557449 0.109 Uiso 1 1 calc R U . . .
H7C H -0.031006 0.634569 0.553213 0.109 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O2 C3 1.344(3) . ?
O2 H2 0.8200 . ?
O1 C1 1.354(3) . ?
O1 H1 0.8200 . ?
N4 O3 1.201(3) . ?
N4 O4 1.204(3) . ?
N4 C2 1.462(3) . ?
N1 C8 1.336(3) . ?
N1 C9 1.345(3) . ?
N2 C12 1.319(3) . ?
N2 C11 1.330(3) . ?
N3 C17 1.342(3) . ?
N3 C21 1.340(3) . ?
C2 C1 1.383(3) . ?
C2 C3 1.391(3) . ?
C3 C4 1.387(3) . ?
C1 C6 1.384(3) . ?
C21 C20 1.384(3) . ?
C21 C21 1.475(5) 2_656 ?
C15 C13 1.372(4) . ?
C15 C14 1.371(3) . ?
C15 C16 1.504(3) . ?
C9 C8 1.393(3) 2_576 ?
C9 C10 1.494(3) . ?
C8 C7 1.504(3) . ?
C13 C11 1.371(4) . ?
C13 H13 0.9300 . ?
C4 C5 1.377(4) . ?
C4 H4 0.9300 . ?
C6 C5 1.378(4) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C20 C19 1.365(4) . ?
C20 H20 0.9300 . ?
C11 H11 0.9300 . ?
C16 C16 1.479(5) 2_755 ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C14 C12 1.374(4) . ?
C14 H14 0.9300 . ?
C18 C17 1.362(4) . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C12 H12 0.9300 . ?
C19 H19 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C3 O2 H2 109.5 . . ?
C1 O1 H1 109.5 . . ?
O3 N4 O4 123.4(2) . . ?
O3 N4 C2 118.1(2) . . ?
O4 N4 C2 118.5(2) . . ?
C8 N1 C9 120.0(2) . . ?
C12 N2 C11 116.1(2) . . ?
C17 N3 C21 117.2(2) . . ?
C1 C2 C3 122.9(2) . . ?
C1 C2 N4 118.47(18) . . ?
C3 C2 N4 118.62(18) . . ?
O2 C3 C4 124.8(2) . . ?
O2 C3 C2 117.7(2) . . ?
C4 C3 C2 117.5(2) . . ?
O1 C1 C6 124.2(2) . . ?
O1 C1 C2 117.3(2) . . ?
C6 C1 C2 118.5(2) . . ?
N3 C21 C20 121.9(2) . . ?
N3 C21 C21 116.4(2) . 2_656 ?
C20 C21 C21 121.7(3) . 2_656 ?
C13 C15 C14 116.1(2) . . ?
C13 C15 C16 122.6(2) . . ?
C14 C15 C16 121.3(2) . . ?
N1 C9 C8 119.4(2) . 2_576 ?
N1 C9 C10 117.6(2) . . ?
C8 C9 C10 123.1(2) 2_576 . ?
N1 C8 C9 120.7(2) . 2_576 ?
N1 C8 C7 117.3(2) . . ?
C9 C8 C7 122.0(2) 2_576 . ?
C15 C13 C11 120.3(2) . . ?
C15 C13 H13 119.8 . . ?
C11 C13 H13 119.8 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C5 C6 C1 119.0(2) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
C4 C5 C6 122.4(3) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C19 C20 C21 119.3(2) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
N2 C11 C13 123.5(2) . . ?
N2 C11 H11 118.2 . . ?
C13 C11 H11 118.2 . . ?
C16 C16 C15 114.4(3) 2_755 . ?
C16 C16 H16A 108.7 2_755 . ?
C15 C16 H16A 108.7 . . ?
C16 C16 H16B 108.7 2_755 . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C15 C14 C12 120.3(3) . . ?
C15 C14 H14 119.9 . . ?
C12 C14 H14 119.9 . . ?
C17 C18 C19 118.0(3) . . ?
C17 C18 H18 121.0 . . ?
C19 C18 H18 121.0 . . ?
N3 C17 C18 124.1(3) . . ?
N3 C17 H17 117.9 . . ?
C18 C17 H17 117.9 . . ?
N2 C12 C14 123.7(2) . . ?
N2 C12 H12 118.1 . . ?
C14 C12 H12 118.1 . . ?
C20 C19 C18 119.5(3) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
 
_refine_diff_density_max    0.257
_refine_diff_density_min   -0.206
_refine_diff_density_rms    0.046


 
data_21NRES-TMP-22BP-DPE-II
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C42 H40 N8 O8' 
_chemical_formula_weight          784.82

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.504(3)
_cell_length_b                    9.428(4)
_cell_length_c                    14.102(6)
_cell_angle_alpha                 94.052(8)
_cell_angle_beta                  91.192(7)
_cell_angle_gamma                 90.498(8)
_cell_volume                      995.0(7)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     4722
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       28.1
 
_exptl_crystal_description        'Prism'
_exptl_crystal_colour             'Colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.310          
_exptl_crystal_F_000              412
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.093
_shelx_estimated_absorpt_T_min    0.982
_shelx_estimated_absorpt_T_max    0.982
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.531
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    ?
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             7618
_diffrn_reflns_av_unetI/netI      0.2076
_diffrn_reflns_av_R_equivalents   0.1474
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.050
_diffrn_reflns_theta_max          25.000
_diffrn_reflns_theta_full         25.000
_diffrn_measured_fraction_theta_max   0.993
_diffrn_measured_fraction_theta_full  0.993
_diffrn_reflns_Laue_measured_fraction_max    0.993
_diffrn_reflns_Laue_measured_fraction_full   0.993
_diffrn_reflns_point_group_measured_fraction_max   0.993
_diffrn_reflns_point_group_measured_fraction_full  0.993
_reflns_number_total              3479
_reflns_number_gt                 1160
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0989P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3479
_refine_ls_number_parameters      268
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2708
_refine_ls_R_factor_gt            0.0931
_refine_ls_wR_factor_ref          0.2601
_refine_ls_wR_factor_gt           0.1895
_refine_ls_goodness_of_fit_ref    0.944
_refine_ls_restrained_S_all       0.944
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.9198(10) 0.6853(7) 0.2538(4) 0.0561(18) Uani 1 1 d . . . . .
C34 C 0.4327(12) 0.7608(12) 0.8657(6) 0.091(3) Uani 1 1 d . . . . .
H34 H 0.433257 0.735672 0.800709 0.109 Uiso 1 1 calc R U . . .
O1 O 0.8452(6) 0.3620(5) 0.3756(3) 0.0678(14) Uani 1 1 d . . . . .
H1 H 0.752205 0.322579 0.389173 0.102 Uiso 1 1 calc R U . . .
N2 N 0.5427(7) 0.2065(6) 0.4074(4) 0.0587(16) Uani 1 1 d . . . . .
C2 C 0.9455(9) 0.5629(7) 0.3021(4) 0.0492(17) Uani 1 1 d . . . . .
C4 C 0.6329(9) 0.5264(7) 0.3149(4) 0.0550(18) Uani 1 1 d . . . . .
H4 H 0.536371 0.474360 0.334815 0.066 Uiso 1 1 calc R U . . .
N1 N 0.9845(7) 0.9181(6) 0.0769(4) 0.0533(14) Uani 1 1 d . . . . .
C3 C 0.8069(9) 0.4818(7) 0.3323(4) 0.0477(17) Uani 1 1 d . . . . .
N3 N 1.1325(8) 0.5226(6) 0.3236(5) 0.0578(16) Uani 1 1 d . . . . .
C12 C 0.2237(9) 0.0592(7) 0.4484(4) 0.0527(18) Uani 1 1 d . . . . .
C6 C 0.7450(10) 0.7281(7) 0.2348(4) 0.066(2) Uani 1 1 d . . . . .
H6 H 0.723069 0.807440 0.200885 0.079 Uiso 1 1 calc R U . . .
C16 C 0.9573(8) 0.8590(7) -0.0114(5) 0.0495(17) Uani 1 1 d . . . . .
C5 C 0.6054(9) 0.6487(7) 0.2679(5) 0.0586(19) Uani 1 1 d . . . . .
H5 H 0.489182 0.678780 0.258087 0.070 Uiso 1 1 calc R U . . .
O2 O 1.0670(6) 0.7546(4) 0.2244(3) 0.0682(14) Uani 1 1 d . . . . .
H2 H 1.035990 0.822180 0.194688 0.102 Uiso 1 1 calc R U . . .
O3 O 1.2044(7) 0.5777(7) 0.3936(4) 0.102(2) Uani 1 1 d . . . . .
O4 O 1.2023(7) 0.4401(6) 0.2677(5) 0.108(2) Uani 1 1 d . . . . .
C15 C 1.0266(8) 1.0586(7) 0.0898(4) 0.0487(17) Uani 1 1 d . . . . .
C13 C 0.0639(9) -0.0232(8) 0.4712(5) 0.0585(19) Uani 1 1 d . . . . .
C14 C 1.0544(11) 1.1204(7) 0.1909(5) 0.079(2) Uani 1 1 d . . . . .
H14A H 1.008927 1.055124 0.233928 0.118 Uiso 1 1 calc R U . . .
H14B H 0.992530 1.208912 0.199244 0.118 Uiso 1 1 calc R U . . .
H14C H 1.179406 1.136333 0.203608 0.118 Uiso 1 1 calc R U . . .
C11 C 0.2596(9) 0.1973(7) 0.4844(5) 0.063(2) Uani 1 1 d . . . . .
H11 H 0.177827 0.244517 0.523584 0.076 Uiso 1 1 calc R U . . .
C8 C 0.3565(9) -0.0024(7) 0.3920(4) 0.0582(19) Uani 1 1 d . . . . .
H8 H 0.342176 -0.095551 0.366492 0.070 Uiso 1 1 calc R U . . .
C9 C 0.5091(9) 0.0728(8) 0.3733(5) 0.064(2) Uani 1 1 d . . . . .
H9 H 0.593553 0.027671 0.334629 0.077 Uiso 1 1 calc R U . . .
C10 C 0.4171(10) 0.2664(7) 0.4624(5) 0.069(2) Uani 1 1 d . . . . .
H10 H 0.435684 0.359371 0.487504 0.082 Uiso 1 1 calc R U . . .
C17 C 0.9080(9) 0.7029(7) -0.0208(5) 0.071(2) Uani 1 1 d . . . . .
H17A H 0.969445 0.656926 -0.073322 0.106 Uiso 1 1 calc R U . . .
H17B H 0.781656 0.692411 -0.031667 0.106 Uiso 1 1 calc R U . . .
H17C H 0.941381 0.660074 0.036654 0.106 Uiso 1 1 calc R U . . .
C21 C 0.4743(8) 0.9252(6) 0.9863(5) 0.0560(18) Uani 1 1 d . . . . .
C22 C 0.4236(9) 0.8324(8) 1.0521(5) 0.063(2) Uani 1 1 d . . . . .
H22 H 0.422148 0.861696 1.116423 0.076 Uiso 1 1 calc R U . . .
C18 C 0.3800(10) 0.6546(9) 0.9252(7) 0.087(3) Uani 1 1 d . . . . .
H18 H 0.350549 0.562795 0.901132 0.104 Uiso 1 1 calc R U . . .
C23 C 0.3746(10) 0.6943(8) 1.0208(7) 0.079(2) Uani 1 1 d . . . . .
H23 H 0.338762 0.629798 1.063733 0.095 Uiso 1 1 calc R U . . .
N19 N 0.4764(9) 0.8795(8) 0.8906(4) 0.078(2) Uani 1 1 d . . . . .
H13 H 0.078(9) -0.126(7) 0.453(4) 0.09(2) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C1 O2 1.365(7) . ?
C1 C2 1.394(8) . ?
C1 C6 1.401(9) . ?
C34 N19 1.190(9) . ?
C34 C18 1.410(10) . ?
O1 C3 1.352(7) . ?
N2 C10 1.337(7) . ?
N2 C9 1.338(7) . ?
C2 C3 1.378(8) . ?
C2 N3 1.487(8) . ?
C4 C5 1.385(8) . ?
C4 C3 1.397(8) . ?
N1 C16 1.339(7) . ?
N1 C15 1.358(7) . ?
N3 O3 1.199(6) . ?
N3 O4 1.199(6) . ?
C12 C11 1.386(8) . ?
C12 C8 1.394(8) . ?
C12 C13 1.476(8) . ?
C6 C5 1.390(8) . ?
C16 C15 1.401(8) 2_775 ?
C16 C17 1.511(8) . ?
C15 C14 1.511(8) . ?
C13 C13 1.327(12) 2_556 ?
C11 C10 1.395(8) . ?
C8 C9 1.381(8) . ?
C21 C22 1.377(8) . ?
C21 N19 1.388(8) . ?
C21 C21 1.481(12) 2_677 ?
C22 C23 1.389(9) . ?
C18 C23 1.375(10) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
O2 C1 C2 117.9(6) . . ?
O2 C1 C6 123.4(7) . . ?
C2 C1 C6 118.6(6) . . ?
N19 C34 C18 126.2(9) . . ?
C10 N2 C9 115.6(5) . . ?
C3 C2 C1 123.0(7) . . ?
C3 C2 N3 119.6(6) . . ?
C1 C2 N3 117.4(5) . . ?
C5 C4 C3 119.4(6) . . ?
C16 N1 C15 119.3(5) . . ?
O1 C3 C2 118.7(6) . . ?
O1 C3 C4 123.1(5) . . ?
C2 C3 C4 118.2(6) . . ?
O3 N3 O4 124.6(7) . . ?
O3 N3 C2 118.0(6) . . ?
O4 N3 C2 117.3(6) . . ?
C11 C12 C8 114.9(6) . . ?
C11 C12 C13 124.2(6) . . ?
C8 C12 C13 120.9(6) . . ?
C5 C6 C1 118.2(7) . . ?
N1 C16 C15 120.3(6) . 2_775 ?
N1 C16 C17 116.7(6) . . ?
C15 C16 C17 123.0(6) 2_775 . ?
C4 C5 C6 122.4(7) . . ?
N1 C15 C16 120.4(5) . 2_775 ?
N1 C15 C14 117.3(6) . . ?
C16 C15 C14 122.3(6) 2_775 . ?
C13 C13 C12 125.3(9) 2_556 . ?
C12 C11 C10 120.8(6) . . ?
C9 C8 C12 121.1(6) . . ?
N2 C9 C8 123.9(6) . . ?
N2 C10 C11 123.7(6) . . ?
C22 C21 N19 119.7(6) . . ?
C22 C21 C21 122.2(8) . 2_677 ?
N19 C21 C21 118.0(9) . 2_677 ?
C21 C22 C23 118.9(7) . . ?
C23 C18 C34 116.3(8) . . ?
C18 C23 C22 118.8(8) . . ?
C34 N19 C21 119.9(8) . . ?
 
_refine_diff_density_max    0.253
_refine_diff_density_min   -0.245
_refine_diff_density_rms    0.062


 
data_22NRES-TMP-22TBP-DPE-I
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C40 H40 N6 O8 S2' 
_chemical_formula_weight          796.90

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.489(3)
_cell_length_b                    9.107(3)
_cell_length_c                    14.187(5)
_cell_angle_alpha                 97.784(7)
_cell_angle_beta                  93.611(7)
_cell_angle_gamma                 90.872(6)
_cell_volume                      956.5(6)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     5609
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.383          
_exptl_crystal_F_000              418
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.201
_shelx_estimated_absorpt_T_min    0.961
_shelx_estimated_absorpt_T_max    0.961
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.613
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication' 
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             8562
_diffrn_reflns_av_unetI/netI      0.1187
_diffrn_reflns_av_R_equivalents   0.0861
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.004
_diffrn_reflns_theta_max          27.481
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.975
_diffrn_measured_fraction_theta_full  0.984
_diffrn_reflns_Laue_measured_fraction_max    0.975
_diffrn_reflns_Laue_measured_fraction_full   0.984
_diffrn_reflns_point_group_measured_fraction_max   0.975
_diffrn_reflns_point_group_measured_fraction_full  0.984
_reflns_number_total              4278
_reflns_number_gt                 2146
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1067P)²+0.7121P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          4278
_refine_ls_number_parameters      255
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1682
_refine_ls_R_factor_gt            0.0890
_refine_ls_wR_factor_ref          0.2651
_refine_ls_wR_factor_gt           0.2229
_refine_ls_goodness_of_fit_ref    1.080
_refine_ls_restrained_S_all       1.080
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
N2 N -0.0381(5) 0.2106(4) 0.4129(3) 0.0372(9) Uani 1 1 d . . . . .
C1 C -0.0119(6) 0.0695(5) 0.3811(4) 0.0413(12) Uani 1 1 d . . . . .
H1A H -0.108574 0.013409 0.350304 0.050 Uiso 1 1 calc R U . . .
C2 C 0.1056(6) 0.2882(5) 0.4571(3) 0.0407(12) Uani 1 1 d . . . . .
H2A H 0.090992 0.387175 0.481222 0.049 Uiso 1 1 calc R U . . .
C3 C 0.1517(6) -0.0004(5) 0.3908(3) 0.0382(11) Uani 1 1 d . . . . .
H3 H 0.162050 -0.100204 0.367608 0.046 Uiso 1 1 calc R U . . .
C4 C 0.2730(6) 0.2290(5) 0.4686(3) 0.0380(11) Uani 1 1 d . . . . .
H4 H 0.368235 0.287968 0.498460 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2980(6) 0.0812(5) 0.4354(3) 0.0299(10) Uani 1 1 d . . . . .
C6 C 0.4790(6) 0.0139(6) 0.4484(3) 0.0377(11) Uani 1 1 d . . . . .
H6A H 0.570212 0.080050 0.430787 0.045 Uiso 1 1 calc R U . . .
H6B H 0.482314 -0.079128 0.406300 0.045 Uiso 1 1 calc R U . . .
O1 O 0.6673(4) 0.3733(3) 0.3799(2) 0.0378(8) Uani 1 1 d . . . . .
H1 H 0.757434 0.325799 0.388906 0.057 Uiso 1 1 d R U . . .
O2 O 0.4421(4) 0.7509(3) 0.2137(2) 0.0397(8) Uani 1 1 d . . . . .
H2 H 0.466938 0.800814 0.172104 0.060 Uiso 1 1 d R U . . .
O3 O 0.2909(4) 0.4448(4) 0.2642(3) 0.0568(11) Uani 1 1 d . . . . .
O4 O 0.3285(5) 0.5975(4) 0.3924(2) 0.0547(10) Uani 1 1 d . . . . .
N3 N 0.3833(5) 0.5318(4) 0.3206(3) 0.0306(9) Uani 1 1 d . . . . .
C7 C 0.7054(6) 0.4825(5) 0.3294(3) 0.0283(10) Uani 1 1 d . . . . .
C8 C 0.5662(5) 0.5663(4) 0.2967(3) 0.0267(9) Uani 1 1 d . . . . .
C9 C 0.5917(6) 0.6803(5) 0.2428(3) 0.0305(10) Uani 1 1 d . . . . .
C10 C 0.7633(6) 0.7174(5) 0.2232(3) 0.0366(11) Uani 1 1 d . . . . .
H10 H 0.784185 0.795052 0.188696 0.044 Uiso 1 1 calc R U . . .
C11 C 0.9048(6) 0.6365(5) 0.2562(3) 0.0338(10) Uani 1 1 d . . . . .
H11 H 1.020866 0.662221 0.243788 0.041 Uiso 1 1 calc R U . . .
C12 C 0.8789(6) 0.5202(5) 0.3062(3) 0.0331(10) Uani 1 1 d . . . . .
H12 H 0.975993 0.466075 0.324857 0.040 Uiso 1 1 calc R U . . .
S1 S 0.0354(2) 0.81487(17) -0.11311(11) 0.0627(5) Uani 1 1 d . . . . .
C17 C 0.1035(8) 0.6659(6) -0.0610(5) 0.0626(16) Uani 1 1 d . . . . .
H17 H 0.127089 0.574163 -0.094770 0.075 Uiso 1 1 calc R U . . .
C18 C 0.1191(8) 0.6954(6) 0.0333(4) 0.0563(15) Uani 1 1 d . . . . .
H18 H 0.154012 0.625008 0.072094 0.068 Uiso 1 1 calc R U . . .
C19 C 0.0784(6) 0.8431(5) 0.0707(4) 0.0421(12) Uani 1 1 d . . . . .
H19 H 0.084706 0.880748 0.135117 0.051 Uiso 1 1 calc R U . . .
C20 C 0.0275(7) 0.9234(6) -0.0033(4) 0.0462(13) Uani 1 1 d . . . . .
N1 N 0.5146(5) 0.9158(4) 0.0728(3) 0.0315(8) Uani 1 1 d . . . . .
C13 C 0.4688(8) 1.1244(6) 0.1933(3) 0.0525(14) Uani 1 1 d . . . . .
H13A H 0.489034 1.047811 0.232812 0.079 Uiso 1 1 calc R U . . .
H13B H 0.351578 1.163210 0.201886 0.079 Uiso 1 1 calc R U . . .
H13C H 0.557029 1.202456 0.210801 0.079 Uiso 1 1 calc R U . . .
C14 C 0.4823(6) 1.0612(5) 0.0907(3) 0.0340(10) Uani 1 1 d . . . . .
C15 C 0.5335(6) 0.8531(5) -0.0165(3) 0.0328(10) Uani 1 1 d . . . . .
C16 C 0.5771(7) 0.6920(5) -0.0320(4) 0.0463(13) Uani 1 1 d . . . . .
H16A H 0.561294 0.649638 0.025437 0.069 Uiso 1 1 calc R U . . .
H16B H 0.698981 0.681399 -0.048533 0.069 Uiso 1 1 calc R U . . .
H16C H 0.498834 0.641632 -0.082739 0.069 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
N2 C1 1.325(6) . ?
N2 C2 1.350(6) . ?
C1 C3 1.397(6) . ?
C1 H1A 0.9300 . ?
C2 C4 1.382(6) . ?
C2 H2A 0.9300 . ?
C3 C5 1.384(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.384(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.507(6) . ?
C6 C6 1.534(9) 2_656 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
O1 C7 1.339(5) . ?
O1 H1 0.8199 . ?
O2 C9 1.370(5) . ?
O2 H2 0.8200 . ?
O3 N3 1.219(5) . ?
O4 N3 1.208(5) . ?
N3 C8 1.471(5) . ?
C7 C8 1.394(5) . ?
C7 C12 1.408(6) . ?
C8 C9 1.387(6) . ?
C9 C10 1.379(6) . ?
C10 C11 1.393(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.370(6) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
S1 C17 1.701(6) . ?
S1 C20 1.733(5) . ?
C17 C18 1.326(8) . ?
C17 H17 0.9300 . ?
C18 C19 1.422(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.396(7) . ?
C19 H19 0.9300 . ?
C20 C20 1.453(11) 2_575 ?
N1 C15 1.334(6) . ?
N1 C14 1.342(5) . ?
C13 C14 1.501(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.394(6) 2_675 ?
C15 C16 1.498(6) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 N2 C2 116.1(4) . . ?
N2 C1 C3 124.2(4) . . ?
N2 C1 H1A 117.9 . . ?
C3 C1 H1A 117.9 . . ?
N2 C2 C4 123.7(4) . . ?
N2 C2 H2A 118.2 . . ?
C4 C2 H2A 118.2 . . ?
C5 C3 C1 119.0(4) . . ?
C5 C3 H3 120.5 . . ?
C1 C3 H3 120.5 . . ?
C2 C4 C5 119.5(4) . . ?
C2 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C3 C5 C4 117.5(4) . . ?
C3 C5 C6 122.1(4) . . ?
C4 C5 C6 120.3(4) . . ?
C5 C6 C6 111.8(5) . 2_656 ?
C5 C6 H6A 109.3 . . ?
C6 C6 H6A 109.3 2_656 . ?
C5 C6 H6B 109.3 . . ?
C6 C6 H6B 109.3 2_656 . ?
H6A C6 H6B 107.9 . . ?
C7 O1 H1 109.6 . . ?
C9 O2 H2 109.4 . . ?
O4 N3 O3 123.1(4) . . ?
O4 N3 C8 118.3(4) . . ?
O3 N3 C8 118.4(4) . . ?
O1 C7 C8 118.9(4) . . ?
O1 C7 C12 124.5(4) . . ?
C8 C7 C12 116.5(4) . . ?
C9 C8 C7 123.3(4) . . ?
C9 C8 N3 118.5(4) . . ?
C7 C8 N3 118.2(4) . . ?
O2 C9 C10 124.0(4) . . ?
O2 C9 C8 117.0(4) . . ?
C10 C9 C8 119.0(4) . . ?
C9 C10 C11 118.8(4) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 122.2(4) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C7 120.2(4) . . ?
C11 C12 H12 119.9 . . ?
C7 C12 H12 119.9 . . ?
C17 S1 C20 91.7(3) . . ?
C18 C17 S1 112.2(5) . . ?
C18 C17 H17 123.9 . . ?
S1 C17 H17 123.9 . . ?
C17 C18 C19 114.9(6) . . ?
C17 C18 H18 122.6 . . ?
C19 C18 H18 122.6 . . ?
C20 C19 C18 110.2(5) . . ?
C20 C19 H19 124.9 . . ?
C18 C19 H19 124.9 . . ?
C19 C20 C20 128.2(6) . 2_575 ?
C19 C20 S1 110.9(4) . . ?
C20 C20 S1 120.8(5) 2_575 . ?
C15 N1 C14 119.8(4) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 120.5(4) . 2_675 ?
N1 C14 C13 116.6(4) . . ?
C15 C14 C13 122.9(4) 2_675 . ?
N1 C15 C14 119.7(4) . 2_675 ?
N1 C15 C16 117.7(4) . . ?
C14 C15 C16 122.6(4) 2_675 . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C2 N2 C1 C3 0.0(7) . . . . ?
C1 N2 C2 C4 1.0(7) . . . . ?
N2 C1 C3 C5 -0.7(8) . . . . ?
N2 C2 C4 C5 -1.4(7) . . . . ?
C1 C3 C5 C4 0.3(7) . . . . ?
C1 C3 C5 C6 -179.9(4) . . . . ?
C2 C4 C5 C3 0.7(7) . . . . ?
C2 C4 C5 C6 -179.2(4) . . . . ?
C3 C5 C6 C6 -104.7(6) . . . 2_656 ?
C4 C5 C6 C6 75.1(7) . . . 2_656 ?
O1 C7 C8 C9 -179.1(4) . . . . ?
C12 C7 C8 C9 0.9(6) . . . . ?
O1 C7 C8 N3 0.8(6) . . . . ?
C12 C7 C8 N3 -179.1(4) . . . . ?
O4 N3 C8 C9 -88.5(5) . . . . ?
O3 N3 C8 C9 87.3(5) . . . . ?
O4 N3 C8 C7 91.5(5) . . . . ?
O3 N3 C8 C7 -92.6(5) . . . . ?
C7 C8 C9 O2 178.5(4) . . . . ?
N3 C8 C9 O2 -1.5(6) . . . . ?
C7 C8 C9 C10 -2.6(7) . . . . ?
N3 C8 C9 C10 177.5(4) . . . . ?
O2 C9 C10 C11 -179.5(4) . . . . ?
C8 C9 C10 C11 1.7(7) . . . . ?
C9 C10 C11 C12 0.9(7) . . . . ?
C10 C11 C12 C7 -2.6(7) . . . . ?
O1 C7 C12 C11 -178.3(4) . . . . ?
C8 C7 C12 C11 1.7(6) . . . . ?
C20 S1 C17 C18 0.1(5) . . . . ?
S1 C17 C18 C19 -0.6(7) . . . . ?
C17 C18 C19 C20 0.9(7) . . . . ?
C18 C19 C20 C20 178.9(6) . . . 2_575 ?
C18 C19 C20 S1 -0.8(5) . . . . ?
C17 S1 C20 C19 0.4(4) . . . . ?
C17 S1 C20 C20 -179.3(6) . . . 2_575 ?
C15 N1 C14 C15 0.8(7) . . . 2_675 ?
C15 N1 C14 C13 -178.0(4) . . . . ?
C14 N1 C15 C14 -0.8(7) . . . 2_675 ?
C14 N1 C15 C16 177.5(4) . . . . ?
 
_refine_diff_density_max    0.338
_refine_diff_density_min   -0.656
_refine_diff_density_rms    0.080


 
data_23NRES-TMP-22TBP-DPE-II
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C40 H38 N6 O8 S2' 
_chemical_formula_weight          794.88

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.514(3)
_cell_length_b                    9.272(3)
_cell_length_c                    13.852(5)
_cell_angle_alpha                 83.832(7)
_cell_angle_beta                  89.887(7)
_cell_angle_gamma                 88.173(7)
_cell_volume                      958.9(6)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     6283
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       27.8
 
_exptl_crystal_description        'Block'
_exptl_crystal_colour             'Yellow'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.376          
_exptl_crystal_F_000              416
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.201
_shelx_estimated_absorpt_T_min    0.961
_shelx_estimated_absorpt_T_max    0.961
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.680
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             7607
_diffrn_reflns_av_unetI/netI      0.0787
_diffrn_reflns_av_R_equivalents   0.0603
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.088
_diffrn_reflns_theta_max          24.994
_diffrn_reflns_theta_full         24.994
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              3352
_reflns_number_gt                 1949
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0844P)²+1.4085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3352
_refine_ls_number_parameters      255
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1301
_refine_ls_R_factor_gt            0.0784
_refine_ls_wR_factor_ref          0.2416
_refine_ls_wR_factor_gt           0.2175
_refine_ls_goodness_of_fit_ref    1.108
_refine_ls_restrained_S_all       1.108
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.4549(3) 0.6806(2) 0.88675(13) 0.0855(7) Uani 1 1 d . . . . .
C15 C 0.4254(7) 0.6582(6) 1.0729(4) 0.0545(14) Uani 1 1 d . . . . .
H15 H 0.425706 0.623078 1.138384 0.065 Uiso 1 1 calc R U . . .
C16 C 0.4711(7) 0.5761(6) 0.9965(4) 0.0583(15) Uani 1 1 d . . . . .
C13 C 0.3899(9) 0.8278(8) 0.9397(6) 0.081(2) Uani 1 1 d . . . . .
H13 H 0.364003 0.918041 0.905753 0.098 Uiso 1 1 calc R U . . .
C14 C 0.3795(9) 0.8009(8) 1.0358(5) 0.0769(19) Uani 1 1 d . . . . .
H14 H 0.344279 0.871635 1.075361 0.092 Uiso 1 1 calc R U . . .
O3 O 0.1468(4) -0.1418(4) 0.6242(3) 0.0510(10) Uani 1 1 d . . . . .
H3 H 0.238364 -0.185294 0.610227 0.076 Uiso 1 1 calc R U . . .
O4 O -0.0720(4) 0.2514(4) 0.7796(3) 0.0543(10) Uani 1 1 d . . . . .
H4 H -0.040830 0.318842 0.808677 0.081 Uiso 1 1 calc R U . . .
C1 C 0.0477(6) 0.0608(5) 0.6999(3) 0.0362(11) Uani 1 1 d . . . . .
N3 N 0.9876(5) 0.5835(4) 0.0751(3) 0.0428(10) Uani 1 1 d . . . . .
N2 N -0.1354(5) 0.0268(5) 0.6766(3) 0.0440(10) Uani 1 1 d . . . . .
C18 C 0.9620(6) 0.6439(5) -0.0153(4) 0.0408(12) Uani 1 1 d . . . . .
N1 N 0.4509(6) 0.7004(5) 0.5911(3) 0.0479(11) Uani 1 1 d . . . . .
C2 C 0.0739(6) 0.1778(5) 0.7507(3) 0.0395(11) Uani 1 1 d . . . . .
C6 C 0.1882(6) -0.0274(5) 0.6701(3) 0.0366(11) Uani 1 1 d . . . . .
C5 C 0.3599(6) 0.0104(5) 0.6911(4) 0.0442(12) Uani 1 1 d . . . . .
H5 H 0.456960 -0.045350 0.673056 0.053 Uiso 1 1 calc R U . . .
C4 C 0.3861(7) 0.1311(6) 0.7388(4) 0.0506(14) Uani 1 1 d . . . . .
H4A H 0.501912 0.157644 0.750217 0.061 Uiso 1 1 calc R U . . .
O2 O -0.2137(6) -0.0569(5) 0.7317(4) 0.0940(17) Uani 1 1 d . . . . .
C11 C 0.7723(6) 0.5568(5) 0.5507(3) 0.0409(12) Uani 1 1 d . . . . .
C3 C 0.2470(7) 0.2132(6) 0.7700(4) 0.0518(14) Uani 1 1 d . . . . .
H3A H 0.268661 0.292136 0.803900 0.062 Uiso 1 1 calc R U . . .
C12 C 0.9351(7) 0.4761(5) 0.5277(3) 0.0453(13) Uani 1 1 d . . . . .
H12 H 0.946805 0.380556 0.555795 0.054 Uiso 1 1 calc R U . . .
C19 C 1.0264(7) 0.4402(5) 0.0923(4) 0.0428(12) Uani 1 1 d . . . . .
C9 C 0.6427(7) 0.4898(6) 0.6081(4) 0.0469(13) Uani 1 1 d . . . . .
H9 H 0.660616 0.394042 0.634719 0.056 Uiso 1 1 calc R U . . .
C10 C 0.7351(7) 0.6995(5) 0.5149(4) 0.0513(14) Uani 1 1 d . . . . .
H10 H 0.817659 0.750957 0.475983 0.062 Uiso 1 1 calc R U . . .
C7 C 0.4856(7) 0.5644(6) 0.6265(4) 0.0474(13) Uani 1 1 d . . . . .
H7 H 0.400498 0.516437 0.665582 0.057 Uiso 1 1 calc R U . . .
C8 C 0.5765(8) 0.7649(6) 0.5369(4) 0.0559(15) Uani 1 1 d . . . . .
H8 H 0.555588 0.861222 0.512101 0.067 Uiso 1 1 calc R U . . .
O1 O -0.2028(6) 0.0918(6) 0.6056(3) 0.0919(16) Uani 1 1 d . . . . .
C20 C 1.0497(10) 0.3791(7) 0.1961(4) 0.0716(18) Uani 1 1 d . . . . .
H20A H 1.000226 0.446456 0.237670 0.107 Uiso 1 1 calc R U . . .
H20B H 1.174221 0.362521 0.210112 0.107 Uiso 1 1 calc R U . . .
H20C H 0.989615 0.288945 0.207179 0.107 Uiso 1 1 calc R U . . .
C17 C 0.9163(8) 0.8033(5) -0.0295(4) 0.0583(15) Uani 1 1 d . . . . .
H17A H 0.793654 0.817900 -0.048497 0.088 Uiso 1 1 calc R U . . .
H17B H 0.990700 0.849492 -0.079238 0.088 Uiso 1 1 calc R U . . .
H17C H 0.935095 0.844578 0.030181 0.088 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
S1 C13 1.676(8) . ?
S1 C16 1.716(6) . ?
C15 C14 1.400(9) . ?
C15 C16 1.405(8) . ?
C16 C16 1.456(12) 2_667 ?
C13 C14 1.330(9) . ?
O3 C6 1.339(5) . ?
O4 C2 1.356(5) . ?
C1 C2 1.374(6) . ?
C1 C6 1.404(6) . ?
C1 N2 1.465(6) . ?
N3 C18 1.328(6) . ?
N3 C19 1.347(6) . ?
N2 O2 1.196(5) . ?
N2 O1 1.201(6) . ?
C18 C19 1.388(7) 2_765 ?
C18 C17 1.499(7) . ?
N1 C7 1.321(6) . ?
N1 C8 1.322(7) . ?
C2 C3 1.385(7) . ?
C6 C5 1.387(7) . ?
C5 C4 1.379(7) . ?
C4 C3 1.369(7) . ?
C11 C9 1.377(7) . ?
C11 C10 1.382(7) . ?
C11 C12 1.466(6) . ?
C12 C12 1.299(9) 2_766 ?
C19 C20 1.497(7) . ?
C9 C7 1.386(7) . ?
C10 C8 1.369(7) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C13 S1 C16 92.0(3) . . ?
C14 C15 C16 109.9(6) . . ?
C15 C16 C16 127.6(7) . 2_667 ?
C15 C16 S1 110.8(5) . . ?
C16 C16 S1 121.6(6) 2_667 . ?
C14 C13 S1 112.4(6) . . ?
C13 C14 C15 114.9(7) . . ?
C2 C1 C6 122.8(4) . . ?
C2 C1 N2 118.3(4) . . ?
C6 C1 N2 118.9(4) . . ?
C18 N3 C19 119.9(4) . . ?
O2 N2 O1 123.3(5) . . ?
O2 N2 C1 118.9(4) . . ?
O1 N2 C1 117.7(5) . . ?
N3 C18 C19 120.3(4) . 2_765 ?
N3 C18 C17 117.4(4) . . ?
C19 C18 C17 122.3(5) 2_765 . ?
C7 N1 C8 116.4(4) . . ?
O4 C2 C1 117.8(4) . . ?
O4 C2 C3 123.8(4) . . ?
C1 C2 C3 118.4(4) . . ?
O3 C6 C5 125.0(4) . . ?
O3 C6 C1 117.7(4) . . ?
C5 C6 C1 117.3(4) . . ?
C4 C5 C6 119.7(4) . . ?
C3 C4 C5 122.1(5) . . ?
C9 C11 C10 116.0(4) . . ?
C9 C11 C12 120.4(4) . . ?
C10 C11 C12 123.6(4) . . ?
C4 C3 C2 119.6(5) . . ?
C12 C12 C11 126.9(6) 2_766 . ?
N3 C19 C18 119.8(4) . 2_765 ?
N3 C19 C20 117.0(4) . . ?
C18 C19 C20 123.2(5) 2_765 . ?
C11 C9 C7 120.3(5) . . ?
C8 C10 C11 119.8(5) . . ?
N1 C7 C9 123.1(5) . . ?
N1 C8 C10 124.4(5) . . ?
 
_refine_diff_density_max    0.333
_refine_diff_density_min   -0.257
_refine_diff_density_rms    0.067


 
data_24NRES-TMP-22BP-22TBP-DPE-I
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C41 H41 N7 O8 S' 
_chemical_formula_weight          791.87

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.4741(15)
_cell_length_b                    9.2215(19)
_cell_length_c                    14.295(3)
_cell_angle_alpha                 96.245(7)
_cell_angle_beta                  92.609(7)
_cell_angle_gamma                 92.314(7)
_cell_volume                      977.4(3)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     7836
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.345          
_exptl_crystal_F_000              416
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.146
_shelx_estimated_absorpt_T_min    0.971
_shelx_estimated_absorpt_T_max    0.971
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.659
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication' 
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9903
_diffrn_reflns_av_unetI/netI      0.0664
_diffrn_reflns_av_R_equivalents   0.0506
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          3.021
_diffrn_reflns_theta_max          27.480
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.988
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.988
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.988
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              4424
_reflns_number_gt                 3102
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0453P)²+0.7428P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.015(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4424
_refine_ls_number_parameters      284
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0973
_refine_ls_R_factor_gt            0.0697
_refine_ls_wR_factor_ref          0.1704
_refine_ls_wR_factor_gt           0.1577
_refine_ls_goodness_of_fit_ref    1.134
_refine_ls_restrained_S_all       1.134
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O1 O 0.3046(3) -0.0630(2) 0.76531(16) 0.0484(6) Uani 1 1 d . . . . .
O4 O 0.6773(2) -0.1253(2) 0.87982(14) 0.0354(5) Uani 1 1 d . . . . .
H4 H 0.766227 -0.173305 0.885983 0.053 Uiso 1 1 calc R U . . .
O3 O 0.4520(2) 0.2504(2) 0.71538(13) 0.0361(5) Uani 1 1 d . . . . .
H3 H 0.474644 0.294543 0.670228 0.054 Uiso 1 1 calc R U . . .
O2 O 0.3323(3) 0.0888(3) 0.89189(14) 0.0473(6) Uani 1 1 d . . . . .
C1 C 0.5771(3) 0.0671(3) 0.79747(17) 0.0254(6) Uani 1 1 d . . . . .
N3 N -0.5206(3) -0.4174(2) 0.42577(15) 0.0272(5) Uani 1 1 d . . . . .
C7 C -0.5355(4) -0.3785(3) 0.69120(19) 0.0399(7) Uani 1 1 d . . . . .
H7A H -0.653083 -0.341975 0.698533 0.060 Uiso 1 1 calc R U . . .
H7B H -0.447117 -0.300289 0.707684 0.060 Uiso 1 1 calc R U . . .
H7C H -0.517601 -0.453664 0.731694 0.060 Uiso 1 1 calc R U . . .
C13 C 0.1527(4) -0.4930(3) 0.89083(19) 0.0347(7) Uani 1 1 d . . . . .
H13 H 0.161014 -0.590677 0.867833 0.042 Uiso 1 1 calc R U . . .
N1 N -0.0303(3) -0.2841(3) 0.91280(16) 0.0329(6) Uani 1 1 d . . . . .
C9 C -0.5390(3) -0.3562(3) 0.51438(18) 0.0259(6) Uani 1 1 d . . . . .
N2 N 0.3912(3) 0.0265(2) 0.81988(15) 0.0264(5) Uani 1 1 d . . . . .
C19 C -0.0795(4) -0.3354(3) 0.4457(2) 0.0378(7) Uani 1 1 d . . . . .
H19 H -0.085922 -0.368162 0.381712 0.045 Uiso 1 1 calc R U . . .
C17 C -0.1104(4) -0.1562(4) 0.5744(3) 0.0475(8) Uani 1 1 d . . . . .
C5 C 0.8926(4) 0.0344(3) 0.8109(2) 0.0345(7) Uani 1 1 d . . . . .
H5 H 0.990539 -0.014201 0.832180 0.041 Uiso 1 1 calc R U . . .
C10 C -0.5863(4) -0.1983(3) 0.5279(2) 0.0329(6) Uani 1 1 d . . . . .
H10A H -0.561832 -0.153482 0.471961 0.049 Uiso 1 1 calc R U . . .
H10B H -0.515860 -0.148486 0.580394 0.049 Uiso 1 1 calc R U . . .
H10C H -0.711270 -0.192321 0.539783 0.049 Uiso 1 1 calc R U . . .
C8 C -0.5176(3) -0.4401(3) 0.59065(18) 0.0274(6) Uani 1 1 d . . . . .
C12 C 0.3023(3) -0.4149(3) 0.93588(17) 0.0270(6) Uani 1 1 d . . . . .
C6 C 0.7179(3) -0.0117(3) 0.83059(18) 0.0277(6) Uani 1 1 d . . . . .
C15 C 0.2791(4) -0.2701(3) 0.96993(19) 0.0320(6) Uani 1 1 d . . . . .
H15 H 0.374137 -0.213643 1.001115 0.038 Uiso 1 1 calc R U . . .
C14 C -0.0089(4) -0.4248(3) 0.8803(2) 0.0342(6) Uani 1 1 d . . . . .
H14 H -0.106316 -0.478762 0.849536 0.041 Uiso 1 1 calc R U . . .
C4 C 0.9189(4) 0.1530(3) 0.75949(19) 0.0336(6) Uani 1 1 d . . . . .
H4A H 1.035223 0.182570 0.747400 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6011(3) 0.1854(3) 0.74473(18) 0.0276(6) Uani 1 1 d . . . . .
C11 C 0.4811(4) -0.4839(3) 0.94871(18) 0.0323(6) Uani 1 1 d . . . . .
H11A H 0.575951 -0.418788 0.931134 0.039 Uiso 1 1 calc R U . . .
H11B H 0.481705 -0.574332 0.907124 0.039 Uiso 1 1 calc R U . . .
C16 C 0.1143(4) -0.2106(3) 0.95720(19) 0.0351(7) Uani 1 1 d . . . . .
H16 H 0.102433 -0.113618 0.980776 0.042 Uiso 1 1 calc R U . . .
C18 C -0.1231(4) -0.1947(4) 0.4789(3) 0.0457(8) Uani 1 1 d . . . . .
H18 H -0.159614 -0.128920 0.437764 0.055 Uiso 1 1 calc R U . . .
C3 C 0.7764(4) 0.2284(3) 0.72574(19) 0.0337(6) Uani 1 1 d . . . . .
H3A H 0.797367 0.306492 0.690989 0.040 Uiso 1 1 calc R U . . .
C20 C -0.0261(4) -0.4241(3) 0.5126(2) 0.0331(6) Uani 1 1 d . . . . .
S1 S -0.0328(4) -0.3253(6) 0.61324(19) 0.0750(12) Uani 0.5 1 d . . P . .
C17A C -0.0589(9) -0.2387(7) 0.6481(5) 0.0352(16) Uani 0.5 1 d . . P . .
N17B N -0.0117(18) -0.3937(11) 0.6151(10) 0.085(5) Uani 0.5 1 d . . P . .
H1 H -0.056(5) -0.214(5) 0.714(3) 0.003(10) Uiso 0.5 1 d . . P . .
H17 H -0.128(5) -0.064(4) 0.601(3) 0.069(12) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O1 N2 1.217(3) . ?
O4 C6 1.356(3) . ?
O3 C2 1.358(3) . ?
O2 N2 1.231(3) . ?
C1 C6 1.397(3) . ?
C1 C2 1.403(4) . ?
C1 N2 1.482(3) . ?
N3 C9 1.345(3) . ?
N3 C8 1.354(3) 2_446 ?
C7 C8 1.501(4) . ?
C13 C14 1.394(4) . ?
C13 C12 1.397(4) . ?
N1 C16 1.348(4) . ?
N1 C14 1.348(4) . ?
C9 C8 1.411(4) . ?
C9 C10 1.507(4) . ?
C19 C20 1.380(4) . ?
C19 C18 1.389(4) . ?
C17 C18 1.370(5) . ?
C17 C17A 1.415(7) . ?
C17 S1 1.819(6) . ?
C5 C4 1.395(4) . ?
C5 C6 1.407(4) . ?
C12 C15 1.391(4) . ?
C12 C11 1.515(3) . ?
C15 C16 1.381(4) . ?
C4 C3 1.392(4) . ?
C2 C3 1.401(4) . ?
C11 C11 1.543(5) 2_647 ?
C20 N17B 1.459(14) . ?
C20 C20 1.480(5) 2_546 ?
C20 S1 1.621(4) . ?
S1 N17B 0.659(10) . ?
S1 C17A 0.927(6) . ?
C17A N17B 1.516(11) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C6 C1 C2 123.6(2) . . ?
C6 C1 N2 119.0(2) . . ?
C2 C1 N2 117.3(2) . . ?
C9 N3 C8 120.1(2) . 2_446 ?
C14 C13 C12 120.1(3) . . ?
C16 N1 C14 116.4(2) . . ?
N3 C9 C8 120.1(2) . . ?
N3 C9 C10 117.6(2) . . ?
C8 C9 C10 122.2(2) . . ?
O1 N2 O2 123.9(2) . . ?
O1 N2 C1 118.5(2) . . ?
O2 N2 C1 117.6(2) . . ?
C20 C19 C18 116.5(3) . . ?
C18 C17 C17A 130.0(4) . . ?
C18 C17 S1 99.9(3) . . ?
C17A C17 S1 30.1(3) . . ?
C4 C5 C6 120.0(2) . . ?
N3 C8 C9 119.7(2) 2_446 . ?
N3 C8 C7 117.4(2) 2_446 . ?
C9 C8 C7 122.8(2) . . ?
C15 C12 C13 116.7(2) . . ?
C15 C12 C11 121.1(2) . . ?
C13 C12 C11 122.1(2) . . ?
O4 C6 C1 118.1(2) . . ?
O4 C6 C5 124.8(2) . . ?
C1 C6 C5 117.1(2) . . ?
C16 C15 C12 119.7(3) . . ?
N1 C14 C13 122.9(3) . . ?
C3 C4 C5 122.0(3) . . ?
O3 C2 C3 124.4(2) . . ?
O3 C2 C1 117.5(2) . . ?
C3 C2 C1 118.1(2) . . ?
C12 C11 C11 111.9(3) . 2_647 ?
N1 C16 C15 124.2(3) . . ?
C17 C18 C19 117.7(3) . . ?
C4 C3 C2 119.2(3) . . ?
C19 C20 N17B 129.6(5) . . ?
C19 C20 C20 122.4(3) . 2_546 ?
N17B C20 C20 108.0(5) . 2_546 ?
C19 C20 S1 105.7(3) . . ?
N17B C20 S1 24.0(4) . . ?
C20 C20 S1 131.9(4) 2_546 . ?
N17B S1 C17A 145.3(16) . . ?
N17B S1 C20 64.1(14) . . ?
C17A S1 C20 150.2(6) . . ?
N17B S1 C17 163.9(14) . . ?
C17A S1 C17 50.0(5) . . ?
C20 S1 C17 100.2(2) . . ?
S1 C17A C17 99.8(7) . . ?
S1 C17A N17B 14.3(7) . . ?
C17 C17A N17B 114.0(7) . . ?
S1 N17B C20 91.9(15) . . ?
S1 N17B C17A 20.3(10) . . ?
C20 N17B C17A 112.1(8) . . ?
 
_refine_diff_density_max    0.228
_refine_diff_density_min   -0.278
_refine_diff_density_rms    0.055


 
data_25NRES-TMP-22BP-22TBP-DPE-II
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C41 H39 N7 O8 S' 
_chemical_formula_weight          789.85

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.1246   0.1234
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    7.4078(12)
_cell_length_b                    9.3192(15)
_cell_length_c                    13.815(2)
_cell_angle_alpha                 94.239(7)
_cell_angle_beta                  91.445(6)
_cell_angle_gamma                 90.299(6)
_cell_volume                      950.8(3)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     7341
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.379          
_exptl_crystal_F_000              414
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.100
_exptl_crystal_size_mid           0.070
_exptl_crystal_size_min           0.050
_exptl_absorpt_coefficient_mu     0.150
_shelx_estimated_absorpt_T_min    0.985
_shelx_estimated_absorpt_T_max    0.993
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.812
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication' 
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube' 
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             9734
_diffrn_reflns_av_unetI/netI      0.0587
_diffrn_reflns_av_R_equivalents   0.0442
_diffrn_reflns_limit_h_min        -9
_diffrn_reflns_limit_h_max        9
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -17
_diffrn_reflns_limit_l_max        17
_diffrn_reflns_theta_min          3.090
_diffrn_reflns_theta_max          27.484
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.994
_diffrn_measured_fraction_theta_full  0.997
_diffrn_reflns_Laue_measured_fraction_max    0.994
_diffrn_reflns_Laue_measured_fraction_full   0.997
_diffrn_reflns_point_group_measured_fraction_max   0.994
_diffrn_reflns_point_group_measured_fraction_full  0.997
_reflns_number_total              4336
_reflns_number_gt                 2799
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0563P)²+0.4009P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    mixed
_refine_ls_hydrogen_treatment     mixed
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.011(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4336
_refine_ls_number_parameters      293
_refine_ls_number_restraints      174
_refine_ls_R_factor_all           0.0971
_refine_ls_R_factor_gt            0.0580
_refine_ls_wR_factor_ref          0.1459
_refine_ls_wR_factor_gt           0.1265
_refine_ls_goodness_of_fit_ref    1.046
_refine_ls_restrained_S_all       1.042
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
O4 O 0.6433(2) 0.64374(17) 0.12183(12) 0.0320(4) Uani 1 1 d . . . . .
H4 H 0.738463 0.687582 0.109558 0.048 Uiso 1 1 calc R U . . .
O1 O 0.4240(2) 0.24695(17) 0.27519(12) 0.0322(4) Uani 1 1 d . . . . .
H1 H 0.453552 0.193892 0.319460 0.048 Uiso 1 1 calc R U . . .
N2 N 0.3576(2) 0.48036(19) 0.17526(14) 0.0261(4) Uani 1 1 d . . . . .
N1 N 0.5126(2) 0.08228(19) 0.42214(13) 0.0249(4) Uani 1 1 d . . . . .
N3 N 0.9500(2) 0.7970(2) 0.09144(13) 0.0286(4) Uani 1 1 d . . . . .
O2 O 0.2830(2) 0.4222(2) 0.10341(13) 0.0545(6) Uani 1 1 d . . . . .
O3 O 0.2854(2) 0.5662(2) 0.23126(16) 0.0564(6) Uani 1 1 d . . . . .
C8 C 0.6858(3) 0.5236(2) 0.16592(15) 0.0245(5) Uani 1 1 d . . . . .
C9 C 0.5450(3) 0.4398(2) 0.19608(15) 0.0233(5) Uani 1 1 d . . . . .
C10 C 0.5724(3) 0.3167(2) 0.24643(15) 0.0249(5) Uani 1 1 d . . . . .
C3 C 1.2717(3) 0.9420(2) 0.05052(15) 0.0247(5) Uani 1 1 d . . . . .
C15 C 0.5420(3) 0.1421(2) 0.51243(16) 0.0244(5) Uani 1 1 d . . . . .
C14 C 0.4721(3) -0.0589(2) 0.40793(16) 0.0251(5) Uani 1 1 d . . . . .
C6 C 1.4340(3) 1.0241(2) 0.02852(16) 0.0275(5) Uani 1 1 d . . . . .
H6 H 1.445520 1.119526 0.057467 0.033 Uiso 1 1 calc R U . . .
C1 C 0.9849(3) 0.9324(2) 0.12778(17) 0.0291(5) Uani 1 1 d . . . . .
H1A H 0.897895 0.979401 0.168126 0.035 Uiso 1 1 calc R U . . .
C7 C 0.8612(3) 0.4779(2) 0.18412(17) 0.0298(5) Uani 1 1 d . . . . .
H7 H 0.960930 0.531226 0.163414 0.036 Uiso 1 1 calc R U . . .
C4 C 1.2368(3) 0.8013(2) 0.01448(17) 0.0288(5) Uani 1 1 d . . . . .
H4A H 1.322465 0.750730 -0.024887 0.035 Uiso 1 1 calc R U . . .
C2 C 1.1405(3) 1.0068(2) 0.10949(16) 0.0277(5) Uani 1 1 d . . . . .
H2 H 1.158388 1.102339 0.137150 0.033 Uiso 1 1 calc R U . . .
C11 C 0.7492(3) 0.2745(2) 0.26437(16) 0.0302(5) Uani 1 1 d . . . . .
H11 H 0.772852 0.191282 0.298285 0.036 Uiso 1 1 calc R U . . .
C5 C 1.0772(3) 0.7352(2) 0.03612(17) 0.0313(5) Uani 1 1 d . . . . .
H5 H 1.056514 0.639209 0.009872 0.038 Uiso 1 1 calc R U . . .
C12 C 0.8902(3) 0.3548(3) 0.23241(17) 0.0314(5) Uani 1 1 d . . . . .
H12 H 1.010602 0.324553 0.243919 0.038 Uiso 1 1 calc R U . . .
C16 C 0.5931(3) 0.2988(2) 0.52371(18) 0.0334(6) Uani 1 1 d . . . . .
H16A H 0.723330 0.308418 0.537177 0.050 Uiso 1 1 calc R U . . .
H16B H 0.527417 0.346359 0.577658 0.050 Uiso 1 1 calc R U . . .
H16C H 0.562005 0.343865 0.463669 0.050 Uiso 1 1 calc R U . . .
C13 C 0.4429(4) -0.1190(3) 0.30502(17) 0.0377(6) Uani 1 1 d . . . . .
H13A H 0.316111 -0.147826 0.294453 0.056 Uiso 1 1 calc R U . . .
H13B H 0.520348 -0.202883 0.292552 0.056 Uiso 1 1 calc R U . . .
H13C H 0.473112 -0.045434 0.260769 0.056 Uiso 1 1 calc R U . . .
S1 S 0.9630(9) 0.8522(6) 0.3867(4) 0.0383(16) Uani 0.25 1 d . U P A 1
C20 C 0.9725(3) 0.9247(2) 0.48836(17) 0.0298(5) Uani 1 1 d . U . . .
C19 C 0.9239(3) 0.8333(3) 0.55728(19) 0.0345(6) Uani 1 1 d . U . . .
H19 H 0.923337 0.864610 0.624285 0.041 Uiso 1 1 calc R U . . .
C18 C 0.8755(3) 0.6932(3) 0.5248(2) 0.0394(6) Uani 1 1 d . U . . .
H18 H 0.841107 0.625584 0.569258 0.047 Uiso 1 1 calc R U . . .
C17 C 0.8788(4) 0.6547(3) 0.4266(2) 0.0443(7) Uani 1 1 d . U . . .
C21 C 0.9262(15) 0.7354(10) 0.3558(8) 0.047(2) Uani 0.5 1 d . U P A .
S1' S 0.9408(12) 0.7923(8) 0.3760(6) 0.071(2) Uani 0.25 1 d . U P A 2
N4 N 0.9767(18) 0.9010(8) 0.3933(9) 0.052(3) Uani 0.5 1 d . U P A 2
H17 H 0.846(4) 0.556(3) 0.398(2) 0.065(9) Uiso 1 1 d . . . . .
H1B H 0.930(5) 0.729(4) 0.283(3) 0.003(9) Uiso 0.5 1 d . . P . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
O4 C8 1.348(2) . ?
O4 H4 0.8400 . ?
O1 C10 1.357(2) . ?
O1 H1 0.8400 . ?
N2 O3 1.208(2) . ?
N2 O2 1.214(2) . ?
N2 C9 1.468(3) . ?
N1 C15 1.340(3) . ?
N1 C14 1.347(3) . ?
N3 C5 1.335(3) . ?
N3 C1 1.345(3) . ?
C8 C9 1.390(3) . ?
C8 C7 1.392(3) . ?
C9 C10 1.399(3) . ?
C10 C11 1.391(3) . ?
C3 C4 1.389(3) . ?
C3 C2 1.395(3) . ?
C3 C6 1.472(3) . ?
C15 C14 1.398(3) 2_656 ?
C15 C16 1.503(3) . ?
C14 C13 1.499(3) . ?
C6 C6 1.330(4) 2_875 ?
C6 H6 0.9500 . ?
C1 C2 1.380(3) . ?
C1 H1A 0.9500 . ?
C7 C12 1.385(3) . ?
C7 H7 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4A 0.9500 . ?
C2 H2 0.9500 . ?
C11 C12 1.381(3) . ?
C11 H11 0.9500 . ?
C5 H5 0.9500 . ?
C12 H12 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
S1 C21 1.168(11) . ?
S1 C20 1.513(6) . ?
S1 C17 2.058(7) . ?
S1 H1B 1.78(4) . ?
C20 N4 1.317(13) . ?
C20 C19 1.377(3) . ?
C20 C20 1.469(5) 2_776 ?
C20 S1' 1.919(9) . ?
C19 C18 1.391(3) . ?
C19 H19 0.9500 . ?
C18 C17 1.378(4) . ?
C18 H18 0.9500 . ?
C17 C21 1.330(11) . ?
C17 S1' 1.576(8) . ?
C17 H17 1.00(3) . ?
C21 S1' 0.589(10) . ?
C21 N4 1.630(12) . ?
C21 H1B 1.01(4) . ?
S1' N4 1.055(11) . ?
S1' H1B 1.38(4) . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C8 O4 H4 109.5 . . ?
C10 O1 H1 109.5 . . ?
O3 N2 O2 123.9(2) . . ?
O3 N2 C9 118.59(19) . . ?
O2 N2 C9 117.50(18) . . ?
C15 N1 C14 119.94(18) . . ?
C5 N3 C1 115.99(18) . . ?
O4 C8 C9 117.92(19) . . ?
O4 C8 C7 124.56(18) . . ?
C9 C8 C7 117.52(19) . . ?
C8 C9 C10 123.06(19) . . ?
C8 C9 N2 119.60(18) . . ?
C10 C9 N2 117.33(17) . . ?
O1 C10 C11 124.43(19) . . ?
O1 C10 C9 117.53(18) . . ?
C11 C10 C9 118.04(18) . . ?
C4 C3 C2 116.30(19) . . ?
C4 C3 C6 123.95(19) . . ?
C2 C3 C6 119.7(2) . . ?
N1 C15 C14 120.20(19) . 2_656 ?
N1 C15 C16 117.63(19) . . ?
C14 C15 C16 122.2(2) 2_656 . ?
N1 C14 C15 119.8(2) . 2_656 ?
N1 C14 C13 117.12(19) . . ?
C15 C14 C13 123.0(2) 2_656 . ?
C6 C6 C3 125.4(3) 2_875 . ?
C6 C6 H6 117.3 2_875 . ?
C3 C6 H6 117.3 . . ?
N3 C1 C2 123.4(2) . . ?
N3 C1 H1A 118.3 . . ?
C2 C1 H1A 118.3 . . ?
C12 C7 C8 120.0(2) . . ?
C12 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C5 C4 C3 119.7(2) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C12 C11 C10 119.4(2) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
N3 C5 C4 124.4(2) . . ?
N3 C5 H5 117.8 . . ?
C4 C5 H5 117.8 . . ?
C11 C12 C7 122.0(2) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C21 S1 C20 133.1(9) . . ?
C21 S1 C17 37.2(6) . . ?
C20 S1 C17 96.0(3) . . ?
C21 S1 H1B 32.3(12) . . ?
C20 S1 H1B 165.3(13) . . ?
C17 S1 H1B 69.4(12) . . ?
N4 C20 C19 129.5(4) . . ?
N4 C20 C20 107.0(4) . 2_776 ?
C19 C20 C20 123.5(3) . 2_776 ?
C19 C20 S1 112.3(3) . . ?
C20 C20 S1 124.2(4) 2_776 . ?
N4 C20 S1' 31.6(5) . . ?
C19 C20 S1' 97.9(3) . . ?
C20 C20 S1' 138.6(4) 2_776 . ?
C20 C19 C18 117.3(2) . . ?
C20 C19 H19 121.3 . . ?
C18 C19 H19 121.3 . . ?
C17 C18 C19 118.4(3) . . ?
C17 C18 H18 120.8 . . ?
C19 C18 H18 120.8 . . ?
C21 C17 C18 128.0(5) . . ?
C21 C17 S1' 21.3(5) . . ?
C18 C17 S1' 106.8(4) . . ?
C21 C17 S1 32.0(4) . . ?
C18 C17 S1 96.0(2) . . ?
C21 C17 H17 109.5(18) . . ?
C18 C17 H17 122.5(18) . . ?
S1' C17 H17 130.7(18) . . ?
S1 C17 H17 141.5(18) . . ?
S1' C21 C17 103.7(16) . . ?
S1 C21 C17 110.8(9) . . ?
S1' C21 N4 10.0(14) . . ?
C17 C21 N4 113.6(9) . . ?
S1' C21 H1B 117(3) . . ?
S1 C21 H1B 110(2) . . ?
C17 C21 H1B 139(2) . . ?
N4 C21 H1B 107(2) . . ?
C21 S1' N4 164(2) . . ?
C21 S1' C17 55.0(13) . . ?
N4 S1' C17 140.4(13) . . ?
C21 S1' C20 154.5(16) . . ?
N4 S1' C20 40.9(9) . . ?
C17 S1' C20 99.6(5) . . ?
C21 S1' H1B 41.0(19) . . ?
N4 S1' H1B 123.6(19) . . ?
C17 S1' H1B 95.9(16) . . ?
C20 S1' H1B 164.5(16) . . ?
S1' N4 C20 107.5(13) . . ?
S1' N4 C21 5.5(8) . . ?
C20 N4 C21 113.0(9) . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
O4 C8 C9 C10 -177.0(2) . . . . ?
C7 C8 C9 C10 2.5(3) . . . . ?
O4 C8 C9 N2 2.8(3) . . . . ?
C7 C8 C9 N2 -177.7(2) . . . . ?
O3 N2 C9 C8 -85.8(3) . . . . ?
O2 N2 C9 C8 96.0(2) . . . . ?
O3 N2 C9 C10 94.0(3) . . . . ?
O2 N2 C9 C10 -84.2(3) . . . . ?
C8 C9 C10 O1 177.6(2) . . . . ?
N2 C9 C10 O1 -2.3(3) . . . . ?
C8 C9 C10 C11 -1.9(3) . . . . ?
N2 C9 C10 C11 178.25(19) . . . . ?
C14 N1 C15 C14 -1.0(3) . . . 2_656 ?
C14 N1 C15 C16 177.87(19) . . . . ?
C15 N1 C14 C15 1.0(3) . . . 2_656 ?
C15 N1 C14 C13 -179.4(2) . . . . ?
C4 C3 C6 C6 0.6(4) . . . 2_875 ?
C2 C3 C6 C6 -178.2(3) . . . 2_875 ?
C5 N3 C1 C2 0.7(3) . . . . ?
O4 C8 C7 C12 178.2(2) . . . . ?
C9 C8 C7 C12 -1.3(3) . . . . ?
C2 C3 C4 C5 1.4(3) . . . . ?
C6 C3 C4 C5 -177.4(2) . . . . ?
N3 C1 C2 C3 0.1(3) . . . . ?
C4 C3 C2 C1 -1.2(3) . . . . ?
C6 C3 C2 C1 177.7(2) . . . . ?
O1 C10 C11 C12 -179.3(2) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C1 N3 C5 C4 -0.4(3) . . . . ?
C3 C4 C5 N3 -0.7(4) . . . . ?
C10 C11 C12 C7 1.0(4) . . . . ?
C8 C7 C12 C11 -0.4(4) . . . . ?
C21 S1 C20 C19 -1.5(13) . . . . ?
C17 S1 C20 C19 -0.1(4) . . . . ?
C21 S1 C20 C20 178.3(11) . . . 2_776 ?
C17 S1 C20 C20 179.7(3) . . . 2_776 ?
N4 C20 C19 C18 1.8(8) . . . . ?
C20 C20 C19 C18 -179.7(3) 2_776 . . . ?
S1 C20 C19 C18 0.2(4) . . . . ?
S1' C20 C19 C18 0.3(4) . . . . ?
C20 C19 C18 C17 -0.1(3) . . . . ?
C19 C18 C17 C21 1.1(7) . . . . ?
C19 C18 C17 S1' -0.2(4) . . . . ?
C19 C18 C17 S1 0.0(3) . . . . ?
C20 S1 C21 C17 2.3(17) . . . . ?
C18 C17 C21 S1' -3.5(19) . . . . ?
C18 C17 C21 S1 -2.1(14) . . . . ?
C18 C17 C21 N4 -2.9(12) . . . . ?
S1' C17 C21 N4 0.6(13) . . . . ?
C17 C21 S1' N4 177(7) . . . . ?
N4 C21 S1' C17 -177(7) . . . . ?
C17 C21 S1' C20 7(4) . . . . ?
N4 C21 S1' C20 -169(11) . . . . ?
C18 C17 S1' C21 177.1(15) . . . . ?
C21 C17 S1' N4 -179(3) . . . . ?
C18 C17 S1' N4 -2(2) . . . . ?
C21 C17 S1' C20 -176.8(18) . . . . ?
C18 C17 S1' C20 0.3(4) . . . . ?
C21 S1' N4 C20 -173(7) . . . . ?
C17 S1' N4 C20 3(3) . . . . ?
C17 S1' N4 C21 176(9) . . . . ?
C20 S1' N4 C21 173(7) . . . . ?
C19 C20 N4 S1' -2.8(18) . . . . ?
C20 C20 N4 S1' 178.5(11) 2_776 . . . ?
C19 C20 N4 C21 -3.6(14) . . . . ?
C20 C20 N4 C21 177.7(8) 2_776 . . . ?
S1' C20 N4 C21 -0.7(7) . . . . ?
C17 C21 N4 S1' -3(8) . . . . ?
S1' C21 N4 C20 7(7) . . . . ?
C17 C21 N4 C20 3.8(14) . . . . ?
 
_refine_diff_density_max    0.265
_refine_diff_density_min   -0.357
_refine_diff_density_rms    0.052


 
data_26CRES-TMP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C14 H16 Cl2 N2 O2' 
_chemical_formula_weight          315.19

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/n'
_space_group_name_Hall            '-P 2yn'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x-1/2, -y-1/2, z-1/2'
 
_cell_length_a                    9.302(3)
_cell_length_b                    9.394(2)
_cell_length_c                    17.660(6)
_cell_angle_alpha                 90
_cell_angle_beta                  104.075(16)
_cell_angle_gamma                 90
_cell_volume                      1497.0(8)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     3729
_cell_measurement_theta_min       2.2
_cell_measurement_theta_max       27.5
 
_exptl_crystal_description        'Prism'
_exptl_crystal_colour             'Colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.398          
_exptl_crystal_F_000              656
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.436
_shelx_estimated_absorpt_T_min    0.918
_shelx_estimated_absorpt_T_max    0.918
_exptl_absorpt_correction_type   'Multi-scan'
_exptl_absorpt_correction_T_min   0.613
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication' 
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube' 
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             15055
_diffrn_reflns_av_unetI/netI      0.1374
_diffrn_reflns_av_R_equivalents   0.1507
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          2.281
_diffrn_reflns_theta_max          27.494
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.991
_diffrn_measured_fraction_theta_full  1.000
_diffrn_reflns_Laue_measured_fraction_max    0.991
_diffrn_reflns_Laue_measured_fraction_full   1.000
_diffrn_reflns_point_group_measured_fraction_max   0.991
_diffrn_reflns_point_group_measured_fraction_full  1.000
_reflns_number_total              3400
_reflns_number_gt                 1828
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3400
_refine_ls_number_parameters      187
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1639
_refine_ls_R_factor_gt            0.0791
_refine_ls_wR_factor_ref          0.3390
_refine_ls_wR_factor_gt           0.1969
_refine_ls_goodness_of_fit_ref    1.012
_refine_ls_restrained_S_all       1.012
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 0.52858(14) -0.11638(13) 0.24050(7) 0.0358(4) Uani 1 1 d . . . . .
Cl2 Cl 1.08751(13) 0.06257(12) 0.37253(7) 0.0355(4) Uani 1 1 d . . . . .
O1 O 0.4420(4) 0.1124(3) 0.3340(2) 0.0349(9) Uani 1 1 d . . . . .
H1 H 0.421413 0.187826 0.352249 0.052 Uiso 1 1 calc R U . . .
O2 O 0.9414(3) 0.2674(4) 0.4518(2) 0.0329(8) Uani 1 1 d . . . . .
H2 H 0.897244 0.333702 0.466265 0.049 Uiso 1 1 calc R U . . .
N1 N 0.3674(4) 0.3345(4) 0.4217(2) 0.0274(8) Uani 1 1 d . . . . .
N2 N 0.2101(4) 0.5320(4) 0.4841(2) 0.0280(9) Uani 1 1 d . . . . .
C12 C 0.2528(5) 0.4096(5) 0.5218(3) 0.0265(10) Uani 1 1 d . . . . .
C13 C 0.3321(5) 0.3089(5) 0.4898(3) 0.0289(10) Uani 1 1 d . . . . .
C6 C 0.6893(5) 0.1942(5) 0.3933(3) 0.0281(10) Uani 1 1 d . . . . .
H6 H 0.652073 0.262907 0.421317 0.034 Uiso 1 1 calc R U . . .
C5 C 0.8432(5) 0.1829(4) 0.4028(3) 0.0276(10) Uani 1 1 d . . . . .
C4 C 0.8971(5) 0.0766(5) 0.3617(3) 0.0276(10) Uani 1 1 d . . . . .
C1 C 0.5910(5) 0.1044(5) 0.3427(3) 0.0269(10) Uani 1 1 d . . . . .
C3 C 0.8005(5) -0.0123(4) 0.3111(3) 0.0272(10) Uani 1 1 d . . . . .
H3 H 0.837437 -0.081085 0.282939 0.033 Uiso 1 1 calc R U . . .
C2 C 0.6485(5) 0.0009(4) 0.3020(3) 0.0279(10) Uani 1 1 d . . . . .
C9 C 0.2467(5) 0.5584(4) 0.4171(3) 0.0260(10) Uani 1 1 d . . . . .
C8 C 0.3261(5) 0.4584(5) 0.3847(3) 0.0269(10) Uani 1 1 d . . . . .
C11 C 0.2102(6) 0.3831(5) 0.5972(3) 0.0361(12) Uani 1 1 d . . . . .
H11A H 0.156628 0.463642 0.609485 0.054 Uiso 1 1 calc R U . . .
H11B H 0.298005 0.368715 0.638190 0.054 Uiso 1 1 calc R U . . .
H11C H 0.148808 0.299781 0.592164 0.054 Uiso 1 1 calc R U . . .
C10 C 0.1954(6) 0.6975(5) 0.3759(3) 0.0369(12) Uani 1 1 d . . . . .
H10A H 0.121759 0.678620 0.328574 0.055 Uiso 1 1 calc R U . . .
H10B H 0.278286 0.745189 0.363788 0.055 Uiso 1 1 calc R U . . .
H10C H 0.153664 0.756832 0.409364 0.055 Uiso 1 1 calc R U . . .
C14 C 0.3817(6) 0.1705(5) 0.5297(3) 0.0411(13) Uani 1 1 d . . . . .
H14A H 0.430699 0.114848 0.497862 0.062 Uiso 1 1 calc R U . . .
H14B H 0.297150 0.119211 0.537486 0.062 Uiso 1 1 calc R U . . .
H14C H 0.449008 0.188528 0.579304 0.062 Uiso 1 1 calc R U . . .
C7 C 0.3682(6) 0.4853(5) 0.3096(3) 0.0368(11) Uani 1 1 d . . . . .
H7A H 0.429369 0.408784 0.299545 0.055 Uiso 1 1 calc R U . . .
H7B H 0.421977 0.573250 0.313151 0.055 Uiso 1 1 calc R U . . .
H7C H 0.280308 0.491193 0.267889 0.055 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl1 C2 1.746(5) . ?
Cl2 C4 1.739(5) . ?
O1 C1 1.359(6) . ?
O1 H1 0.8200 . ?
O2 C5 1.353(5) . ?
O2 H2 0.8200 . ?
N1 C13 1.344(6) . ?
N1 C8 1.344(6) . ?
N2 C9 1.332(6) . ?
N2 C12 1.339(6) . ?
C12 C13 1.400(6) . ?
C12 C11 1.499(6) . ?
C13 C14 1.497(6) . ?
C6 C1 1.396(6) . ?
C6 C5 1.404(6) . ?
C6 H6 0.9300 . ?
C5 C4 1.398(6) . ?
C4 C3 1.383(6) . ?
C1 C2 1.390(6) . ?
C3 C2 1.390(6) . ?
C3 H3 0.9300 . ?
C9 C8 1.399(6) . ?
C9 C10 1.515(6) . ?
C8 C7 1.493(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 O1 H1 109.5 . . ?
C5 O2 H2 109.5 . . ?
C13 N1 C8 119.1(4) . . ?
C9 N2 C12 119.5(4) . . ?
N2 C12 C13 120.0(4) . . ?
N2 C12 C11 118.3(4) . . ?
C13 C12 C11 121.6(4) . . ?
N1 C13 C12 120.5(4) . . ?
N1 C13 C14 117.5(4) . . ?
C12 C13 C14 122.0(4) . . ?
C1 C6 C5 121.4(4) . . ?
C1 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
O2 C5 C4 118.7(4) . . ?
O2 C5 C6 122.8(4) . . ?
C4 C5 C6 118.5(4) . . ?
C3 C4 C5 120.5(4) . . ?
C3 C4 Cl2 120.6(3) . . ?
C5 C4 Cl2 118.8(4) . . ?
O1 C1 C2 119.3(4) . . ?
O1 C1 C6 122.0(4) . . ?
C2 C1 C6 118.6(4) . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C2 C1 120.8(4) . . ?
C3 C2 Cl1 119.6(3) . . ?
C1 C2 Cl1 119.7(4) . . ?
N2 C9 C8 120.8(4) . . ?
N2 C9 C10 117.9(4) . . ?
C8 C9 C10 121.3(4) . . ?
N1 C8 C9 120.0(4) . . ?
N1 C8 C7 118.2(4) . . ?
C9 C8 C7 121.8(4) . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C8 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
 
_refine_diff_density_max    1.630
_refine_diff_density_min   -1.582
_refine_diff_density_rms    0.294


 
data_27CRES-PHE
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C72 H48 Cl4 N10 O4' 
_chemical_formula_weight          1259.00

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    10.807(5)
_cell_length_b                    12.145(5)
_cell_length_c                    12.466(6)
_cell_angle_alpha                 108.220(8)
_cell_angle_beta                  104.061(7)
_cell_angle_gamma                 101.072(7)
_cell_volume                      1442.3(11)
_cell_formula_units_Z             1
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     7173
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       27.7
 
_exptl_crystal_description        'Prism'
_exptl_crystal_colour             'Colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.449          
_exptl_crystal_F_000              650
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.270
_shelx_estimated_absorpt_T_min    0.948
_shelx_estimated_absorpt_T_max    0.948
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.413
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             11846
_diffrn_reflns_av_unetI/netI      0.1296
_diffrn_reflns_av_R_equivalents   0.1036
_diffrn_reflns_limit_h_min        -14
_diffrn_reflns_limit_h_max        13
_diffrn_reflns_limit_k_min        -15
_diffrn_reflns_limit_k_max        15
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.041
_diffrn_reflns_theta_max          27.485
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.959
_diffrn_measured_fraction_theta_full  0.975
_diffrn_reflns_Laue_measured_fraction_max    0.959
_diffrn_reflns_Laue_measured_fraction_full   0.975
_diffrn_reflns_point_group_measured_fraction_max   0.959
_diffrn_reflns_point_group_measured_fraction_full  0.975
_reflns_number_total              6333
_reflns_number_gt                 3189
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1435P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          6333
_refine_ls_number_parameters      408
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1675
_refine_ls_R_factor_gt            0.0880
_refine_ls_wR_factor_ref          0.2692
_refine_ls_wR_factor_gt           0.2076
_refine_ls_goodness_of_fit_ref    0.974
_refine_ls_restrained_S_all       0.974
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl01 Cl 0.20780(12) -0.03104(11) 0.94958(10) 0.0367(3) Uani 1 1 d . . . . .
Cl02 Cl 0.00215(12) 0.34369(11) 1.08446(10) 0.0373(4) Uani 1 1 d . . . . .
O2 O 0.0875(3) 0.4082(3) 0.9012(3) 0.0371(8) Uani 1 1 d . . . . .
H2 H 0.117313 0.425655 0.852210 0.056 Uiso 1 1 calc R U . . .
O1 O 0.2811(3) 0.0814(3) 0.7878(3) 0.0391(8) Uani 1 1 d . . . . .
H1 H 0.299973 0.115369 0.743980 0.059 Uiso 1 1 calc R U . . .
N3 N 0.3382(4) 0.2067(3) 0.6457(3) 0.0288(9) Uani 1 1 d . . . . .
N5 N 0.5352(4) 0.0651(3) 0.4295(3) 0.0310(9) Uani 1 1 d . . . . .
N1 N 0.1729(4) 0.4791(4) 0.7303(3) 0.0300(9) Uani 1 1 d . . . . .
N2 N 0.2504(4) 0.5775(4) 0.5690(3) 0.0330(9) Uani 1 1 d . . . . .
N4 N 0.4017(4) 0.3300(3) 0.4977(3) 0.0300(9) Uani 1 1 d . . . . .
C4 C 0.1097(4) 0.1615(4) 1.0051(4) 0.0303(11) Uani 1 1 d . . . . .
H4 H 0.084480 0.133461 1.060279 0.036 Uiso 1 1 calc R U . . .
C19 C 0.4272(4) 0.3175(4) 0.6922(4) 0.0282(10) Uani 1 1 d . . . . .
C7 C 0.2672(4) 0.5875(4) 0.7696(4) 0.0312(11) Uani 1 1 d . . . . .
C12 C 0.3050(5) 0.6374(4) 0.6882(4) 0.0313(11) Uani 1 1 d . . . . .
C2 C 0.1178(4) 0.3093(4) 0.9115(4) 0.0303(11) Uani 1 1 d . . . . .
C6 C 0.2161(4) 0.1434(4) 0.8543(4) 0.0297(10) Uani 1 1 d . . . . .
C34 C 0.4449(4) -0.0462(4) 0.3798(4) 0.0292(10) Uani 1 1 d . . . . .
C20 C 0.4888(4) 0.3741(4) 0.8178(4) 0.0317(11) Uani 1 1 d . . . . .
H20 H 0.470152 0.334021 0.867157 0.038 Uiso 1 1 calc R U . . .
C1 C 0.1854(4) 0.2451(4) 0.8423(4) 0.0311(11) Uani 1 1 d . . . . .
H1A H 0.210240 0.272338 0.786499 0.037 Uiso 1 1 calc R U . . .
C25 C 0.3126(4) 0.2196(4) 0.4517(4) 0.0282(10) Uani 1 1 d . . . . .
C14 C 0.0946(5) 0.4038(4) 0.4042(4) 0.0342(11) Uani 1 1 d . . . . .
H14 H 0.120403 0.434296 0.350740 0.041 Uiso 1 1 calc R U . . .
C33 C 0.5917(4) 0.1117(4) 0.5500(4) 0.0296(10) Uani 1 1 d . . . . .
C8 C 0.3297(5) 0.6544(4) 0.8945(4) 0.0324(11) Uani 1 1 d . . . . .
H8 H 0.306812 0.623307 0.948666 0.039 Uiso 1 1 calc R U . . .
C26 C 0.2500(5) 0.1620(5) 0.3257(4) 0.0359(12) Uani 1 1 d . . . . .
H26 H 0.272573 0.200565 0.276355 0.043 Uiso 1 1 calc R U . . .
C30 C 0.2769(4) 0.1556(4) 0.5252(4) 0.0292(10) Uani 1 1 d . . . . .
C24 C 0.4575(4) 0.3795(4) 0.6171(4) 0.0302(11) Uani 1 1 d . . . . .
C13 C 0.1572(4) 0.4705(4) 0.5298(4) 0.0301(10) Uani 1 1 d . . . . .
C18 C 0.1174(5) 0.4202(4) 0.6115(4) 0.0306(11) Uani 1 1 d . . . . .
C23 C 0.5509(5) 0.4977(4) 0.6709(4) 0.0353(11) Uani 1 1 d . . . . .
H23 H 0.572889 0.538429 0.623049 0.042 Uiso 1 1 calc R U . . .
C35 C 0.3822(5) -0.0987(5) 0.2544(4) 0.0370(12) Uani 1 1 d . . . . .
H35 H 0.405556 -0.057980 0.206992 0.044 Uiso 1 1 calc R U . . .
C17 C 0.0160(5) 0.3086(4) 0.5634(4) 0.0364(12) Uani 1 1 d . . . . .
H17 H -0.011629 0.275591 0.614594 0.044 Uiso 1 1 calc R U . . .
C5 C 0.1758(4) 0.1003(4) 0.9364(4) 0.0301(10) Uani 1 1 d . . . . .
C3 C 0.0803(4) 0.2642(4) 0.9932(4) 0.0324(11) Uani 1 1 d . . . . .
C21 C 0.5762(5) 0.4884(4) 0.8658(4) 0.0341(11) Uani 1 1 d . . . . .
H21 H 0.615744 0.525923 0.948190 0.041 Uiso 1 1 calc R U . . .
C15 C -0.0014(5) 0.2971(5) 0.3621(4) 0.0378(12) Uani 1 1 d . . . . .
H15 H -0.041243 0.254795 0.280259 0.045 Uiso 1 1 calc R U . . .
C32 C 0.6871(5) 0.2280(4) 0.6063(4) 0.0373(12) Uani 1 1 d . . . . .
H32 H 0.708354 0.272438 0.561282 0.045 Uiso 1 1 calc R U . . .
C29 C 0.1795(5) 0.0418(4) 0.4721(4) 0.0363(11) Uani 1 1 d . . . . .
H29 H 0.154675 0.001357 0.519275 0.044 Uiso 1 1 calc R U . . .
C16 C -0.0416(5) 0.2491(5) 0.4437(4) 0.0379(12) Uani 1 1 d . . . . .
H16 H -0.108372 0.175962 0.414034 0.045 Uiso 1 1 calc R U . . .
C11 C 0.4023(5) 0.7524(5) 0.7348(4) 0.0364(12) Uani 1 1 d . . . . .
H11 H 0.427097 0.786074 0.682931 0.044 Uiso 1 1 calc R U . . .
C9 C 0.4230(5) 0.7641(5) 0.9349(4) 0.0376(12) Uani 1 1 d . . . . .
H9 H 0.463336 0.806896 1.016689 0.045 Uiso 1 1 calc R U . . .
C31 C 0.7475(5) 0.2740(5) 0.7278(5) 0.0409(13) Uani 1 1 d . . . . .
H31 H 0.812263 0.348808 0.764881 0.049 Uiso 1 1 calc R U . . .
C36 C 0.2879(5) -0.2086(5) 0.2030(4) 0.0403(13) Uani 1 1 d . . . . .
H36 H 0.246091 -0.241166 0.120751 0.048 Uiso 1 1 calc R U . . .
C28 C 0.1223(5) -0.0080(5) 0.3520(5) 0.0412(13) Uani 1 1 d . . . . .
H28 H 0.058149 -0.083133 0.317398 0.049 Uiso 1 1 calc R U . . .
C22 C 0.6079(5) 0.5512(5) 0.7918(4) 0.0422(13) Uani 1 1 d . . . . .
H22 H 0.667480 0.628715 0.826263 0.051 Uiso 1 1 calc R U . . .
C10 C 0.4593(5) 0.8135(5) 0.8551(4) 0.0403(12) Uani 1 1 d . . . . .
H10 H 0.522861 0.888551 0.884694 0.048 Uiso 1 1 calc R U . . .
C27 C 0.1577(5) 0.0514(5) 0.2766(4) 0.0425(13) Uani 1 1 d . . . . .
H27 H 0.117608 0.014534 0.194237 0.051 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl01 C5 1.743(5) . ?
Cl02 C3 1.741(5) . ?
O2 C2 1.338(5) . ?
O2 H2 0.8200 . ?
O1 C6 1.358(5) . ?
O1 H1 0.8200 . ?
N3 C19 1.347(6) . ?
N3 C30 1.363(5) . ?
N5 C34 1.356(6) . ?
N5 C33 1.357(5) . ?
N1 C18 1.344(6) . ?
N1 C7 1.361(6) . ?
N2 C13 1.343(6) . ?
N2 C12 1.348(5) . ?
N4 C24 1.344(5) . ?
N4 C25 1.345(6) . ?
C4 C5 1.378(6) . ?
C4 C3 1.387(6) . ?
C4 H4 0.9300 . ?
C19 C20 1.419(6) . ?
C19 C24 1.431(6) . ?
C7 C8 1.424(6) . ?
C7 C12 1.433(6) . ?
C12 C11 1.423(7) . ?
C2 C3 1.403(6) . ?
C2 C1 1.410(6) . ?
C6 C1 1.381(6) . ?
C6 C5 1.406(6) . ?
C34 C35 1.416(6) . ?
C34 C33 1.428(6) 2_656 ?
C20 C21 1.372(7) . ?
C20 H20 0.9300 . ?
C1 H1A 0.9300 . ?
C25 C26 1.425(6) . ?
C25 C30 1.446(6) . ?
C14 C15 1.351(7) . ?
C14 C13 1.430(6) . ?
C14 H14 0.9300 . ?
C33 C32 1.420(7) . ?
C8 C9 1.365(7) . ?
C8 H8 0.9300 . ?
C26 C27 1.360(7) . ?
C26 H26 0.9300 . ?
C30 C29 1.410(6) . ?
C24 C23 1.429(6) . ?
C13 C18 1.448(6) . ?
C18 C17 1.414(7) . ?
C23 C22 1.363(6) . ?
C23 H23 0.9300 . ?
C35 C36 1.363(7) . ?
C35 H35 0.9300 . ?
C17 C16 1.356(6) . ?
C17 H17 0.9300 . ?
C21 C22 1.429(7) . ?
C21 H21 0.9300 . ?
C15 C16 1.431(7) . ?
C15 H15 0.9300 . ?
C32 C31 1.372(7) . ?
C32 H32 0.9300 . ?
C29 C28 1.354(7) . ?
C29 H29 0.9300 . ?
C16 H16 0.9300 . ?
C11 C10 1.364(6) . ?
C11 H11 0.9300 . ?
C9 C10 1.405(7) . ?
C9 H9 0.9300 . ?
C31 C36 1.412(7) 2_656 ?
C31 H31 0.9300 . ?
C36 H36 0.9300 . ?
C28 C27 1.428(7) . ?
C28 H28 0.9300 . ?
C22 H22 0.9300 . ?
C10 H10 0.9300 . ?
C27 H27 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 O2 H2 109.5 . . ?
C6 O1 H1 109.5 . . ?
C19 N3 C30 118.2(4) . . ?
C34 N5 C33 117.0(4) . . ?
C18 N1 C7 116.9(4) . . ?
C13 N2 C12 117.3(4) . . ?
C24 N4 C25 116.6(4) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N3 C19 C20 119.1(4) . . ?
N3 C19 C24 121.0(4) . . ?
C20 C19 C24 119.9(4) . . ?
N1 C7 C8 119.7(4) . . ?
N1 C7 C12 121.6(4) . . ?
C8 C7 C12 118.7(4) . . ?
N2 C12 C11 119.7(4) . . ?
N2 C12 C7 121.3(4) . . ?
C11 C12 C7 119.0(4) . . ?
O2 C2 C3 119.8(4) . . ?
O2 C2 C1 123.3(4) . . ?
C3 C2 C1 117.0(4) . . ?
O1 C6 C1 122.6(4) . . ?
O1 C6 C5 118.5(4) . . ?
C1 C6 C5 118.9(4) . . ?
N5 C34 C35 119.3(4) . . ?
N5 C34 C33 122.2(4) . 2_656 ?
C35 C34 C33 118.5(4) . 2_656 ?
C21 C20 C19 119.3(4) . . ?
C21 C20 H20 120.3 . . ?
C19 C20 H20 120.3 . . ?
C6 C1 C2 122.5(4) . . ?
C6 C1 H1A 118.8 . . ?
C2 C1 H1A 118.8 . . ?
N4 C25 C26 119.3(4) . . ?
N4 C25 C30 122.7(4) . . ?
C26 C25 C30 118.0(4) . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
N5 C33 C32 119.1(4) . . ?
N5 C33 C34 120.8(4) . 2_656 ?
C32 C33 C34 120.0(4) . 2_656 ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C27 C26 C25 120.7(5) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
N3 C30 C29 120.6(4) . . ?
N3 C30 C25 119.3(4) . . ?
C29 C30 C25 120.1(4) . . ?
N4 C24 C23 119.0(4) . . ?
N4 C24 C19 122.2(4) . . ?
C23 C24 C19 118.8(4) . . ?
N2 C13 C14 119.7(4) . . ?
N2 C13 C18 121.7(4) . . ?
C14 C13 C18 118.6(4) . . ?
N1 C18 C17 120.5(4) . . ?
N1 C18 C13 121.1(4) . . ?
C17 C18 C13 118.4(4) . . ?
C22 C23 C24 120.5(5) . . ?
C22 C23 H23 119.8 . . ?
C24 C23 H23 119.8 . . ?
C36 C35 C34 120.3(5) . . ?
C36 C35 H35 119.9 . . ?
C34 C35 H35 119.9 . . ?
C16 C17 C18 121.0(5) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C4 C5 C6 119.7(4) . . ?
C4 C5 Cl01 120.3(4) . . ?
C6 C5 Cl01 120.0(4) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 Cl02 120.5(4) . . ?
C2 C3 Cl02 118.5(4) . . ?
C20 C21 C22 121.4(4) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 H21 119.3 . . ?
C14 C15 C16 120.0(5) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C31 C32 C33 119.4(5) . . ?
C31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
C28 C29 C30 119.4(5) . . ?
C28 C29 H29 120.3 . . ?
C30 C29 H29 120.3 . . ?
C17 C16 C15 121.0(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C10 C11 C12 120.4(5) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C8 C9 C10 121.1(4) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 H9 119.4 . . ?
C32 C31 C36 120.5(5) . 2_656 ?
C32 C31 H31 119.8 . . ?
C36 C31 H31 119.8 2_656 . ?
C35 C36 C31 121.3(4) . 2_656 ?
C35 C36 H36 119.4 . . ?
C31 C36 H36 119.4 2_656 . ?
C29 C28 C27 121.9(5) . . ?
C29 C28 H28 119.0 . . ?
C27 C28 H28 119.0 . . ?
C23 C22 C21 120.1(5) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C11 C10 C9 120.6(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C26 C27 C28 119.9(5) . . ?
C26 C27 H27 120.1 . . ?
C28 C27 H27 120.1 . . ?
 
_refine_diff_density_max    0.683
_refine_diff_density_min   -0.668
_refine_diff_density_rms    0.102


 
data_28CRES-DMP
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C12 H12 Cl2 N2 O2' 
_chemical_formula_weight          287.14

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            14
_space_group_name_H-M_alt         'P 21/c'
_space_group_name_Hall            '-P 2ybc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y-1/2, z-1/2'
 
_cell_length_a                    8.188(12)
_cell_length_b                    15.73(2)
_cell_length_c                    11.247(16)
_cell_angle_alpha                 90
_cell_angle_beta                  110.491(16)
_cell_angle_gamma                 90
_cell_volume                      1357(3)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     3075
_cell_measurement_theta_min       3.23
_cell_measurement_theta_max       27.49
 
_exptl_crystal_description        'Block' 
_exptl_crystal_colour             'COlorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.406          
_exptl_crystal_F_000              592
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.410
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.473
_shelx_estimated_absorpt_T_min    0.830
_shelx_estimated_absorpt_T_max    0.911
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.950
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             7471
_diffrn_reflns_av_unetI/netI      0.0888
_diffrn_reflns_av_R_equivalents   0.1147
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -20
_diffrn_reflns_limit_k_max        20
_diffrn_reflns_limit_l_min        -12
_diffrn_reflns_limit_l_max        14
_diffrn_reflns_theta_min          3.232
_diffrn_reflns_theta_max          27.494
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.987
_diffrn_measured_fraction_theta_full  0.990
_diffrn_reflns_Laue_measured_fraction_max    0.987
_diffrn_reflns_Laue_measured_fraction_full   0.990
_diffrn_reflns_point_group_measured_fraction_max   0.987
_diffrn_reflns_point_group_measured_fraction_full  0.990
_reflns_number_total              3075
_reflns_number_gt                 2111
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1001P)²+0.2332P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          3075
_refine_ls_number_parameters      167
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0925
_refine_ls_R_factor_gt            0.0666
_refine_ls_wR_factor_ref          0.2057
_refine_ls_wR_factor_gt           0.1824
_refine_ls_goodness_of_fit_ref    1.040
_refine_ls_restrained_S_all       1.040
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl01 Cl 1.09648(11) 0.69449(6) 0.75323(10) 0.0749(3) Uani 1 1 d . . . . .
Cl02 Cl 0.58993(13) 0.71985(7) 0.29686(9) 0.0774(4) Uani 1 1 d . . . . .
O1 O 0.8356(3) 0.59886(16) 0.8224(2) 0.0651(6) Uani 1 1 d . . . . .
H1 H 0.753466 0.587013 0.845110 0.098 Uiso 1 1 calc R U . . .
O2 O 0.3852(3) 0.62137(17) 0.4089(2) 0.0694(7) Uani 1 1 d . . . . .
H2 H 0.326541 0.597031 0.444489 0.104 Uiso 1 1 calc R U . . .
N2 N 0.1360(3) 0.54121(16) 0.4782(3) 0.0532(6) Uani 1 1 d . . . . .
N1 N 0.5952(4) 0.5317(2) 0.9295(3) 0.0687(8) Uani 1 1 d . . . . .
C007 C 0.5471(3) 0.63644(17) 0.4938(3) 0.0462(6) Uani 1 1 d . . . . .
C1 C 0.6066(3) 0.60794(18) 0.6177(3) 0.0492(7) Uani 1 1 d . . . . .
H1A H 0.532392 0.576151 0.646760 0.059 Uiso 1 1 calc R U . . .
C2 C 0.7741(3) 0.62546(17) 0.7000(3) 0.0463(6) Uani 1 1 d . . . . .
C4 C 0.8289(4) 0.70046(17) 0.5320(3) 0.0511(7) Uani 1 1 d . . . . .
H4 H 0.903713 0.731617 0.502717 0.061 Uiso 1 1 calc R U . . .
C5 C 0.6612(4) 0.68367(18) 0.4516(3) 0.0479(6) Uani 1 1 d . . . . .
C7 C -0.0218(4) 0.5365(2) 0.3857(3) 0.0523(7) Uani 1 1 d . . . . .
C3 C 0.8862(4) 0.67152(17) 0.6549(3) 0.0495(7) Uani 1 1 d . . . . .
C10 C 0.6135(4) 0.4497(2) 0.9665(3) 0.0630(9) Uani 1 1 d . . . . .
C8 C 0.1541(4) 0.50547(19) 0.5892(3) 0.0550(7) Uani 1 1 d . . . . .
H8 H 0.262369 0.508976 0.653787 0.066 Uiso 1 1 calc R U . . .
C11 C 0.4842(4) 0.5799(3) 0.9625(3) 0.0700(9) Uani 1 1 d . . . . .
H11 H 0.471294 0.636453 0.936788 0.084 Uiso 1 1 calc R U . . .
C9 C 0.7407(5) 0.3957(3) 0.9327(4) 0.0833(12) Uani 1 1 d . . . . .
H9A H 0.717136 0.399152 0.843048 0.125 Uiso 1 1 calc R U . . .
H9B H 0.729705 0.337703 0.955653 0.125 Uiso 1 1 calc R U . . .
H9C H 0.856969 0.415341 0.977796 0.125 Uiso 1 1 calc R U . . .
C6 C -0.0478(5) 0.5743(3) 0.2602(4) 0.0769(10) Uani 1 1 d . . . . .
H6A H 0.044082 0.614208 0.267707 0.115 Uiso 1 1 calc R U . . .
H6B H -0.158069 0.603112 0.229773 0.115 Uiso 1 1 calc R U . . .
H6C H -0.046107 0.530262 0.201581 0.115 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl01 C3 1.727(4) . ?
Cl02 C5 1.727(4) . ?
O1 C2 1.356(4) . ?
O1 H1 0.8200 . ?
O2 C007 1.356(4) . ?
O2 H2 0.8200 . ?
N2 C8 1.330(4) . ?
N2 C7 1.347(4) . ?
N1 C11 1.332(5) . ?
N1 C10 1.347(5) . ?
C007 C1 1.380(5) . ?
C007 C5 1.400(4) . ?
C1 C2 1.388(4) . ?
C1 H1A 0.9300 . ?
C2 C3 1.397(4) . ?
C4 C3 1.373(5) . ?
C4 C5 1.380(4) . ?
C4 H4 0.9300 . ?
C7 C8 1.379(4) 3_566 ?
C7 C6 1.477(5) . ?
C10 C11 1.393(4) 3_667 ?
C10 C9 1.492(5) . ?
C8 H8 0.9300 . ?
C11 H11 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C007 O2 H2 109.5 . . ?
C8 N2 C7 117.6(2) . . ?
C11 N1 C10 118.2(3) . . ?
O2 C007 C1 124.5(2) . . ?
O2 C007 C5 117.3(3) . . ?
C1 C007 C5 118.3(3) . . ?
C007 C1 C2 121.7(2) . . ?
C007 C1 H1A 119.1 . . ?
C2 C1 H1A 119.1 . . ?
O1 C2 C1 123.0(2) . . ?
O1 C2 C3 118.1(3) . . ?
C1 C2 C3 118.9(3) . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C007 120.6(3) . . ?
C4 C5 Cl02 120.4(2) . . ?
C007 C5 Cl02 119.1(2) . . ?
N2 C7 C8 118.6(3) . 3_566 ?
N2 C7 C6 119.6(3) . . ?
C8 C7 C6 121.9(3) 3_566 . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 Cl01 119.2(2) . . ?
C2 C3 Cl01 120.7(3) . . ?
N1 C10 C11 118.2(3) . 3_667 ?
N1 C10 C9 118.6(3) . . ?
C11 C10 C9 123.2(4) 3_667 . ?
N2 C8 C7 123.8(3) . 3_566 ?
N2 C8 H8 118.1 . . ?
C7 C8 H8 118.1 3_566 . ?
N1 C11 C10 123.6(4) . 3_667 ?
N1 C11 H11 118.2 . . ?
C10 C11 H11 118.2 3_667 . ?
C10 C9 H9A 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C10 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
 
_refine_diff_density_max    0.290
_refine_diff_density_min   -0.401
_refine_diff_density_rms    0.066


 
data_29CRES-TMP-PYR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C44 H42 Cl4 N4 O4' 
_chemical_formula_weight          832.61

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    42.727(11)
_cell_length_b                    8.899(3)
_cell_length_c                    22.920(6)
_cell_angle_alpha                 90
_cell_angle_beta                  114.062(8)
_cell_angle_gamma                 90
_cell_volume                      7958(4)
_cell_formula_units_Z             8
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     10775
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       28.2
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Colorless
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.390          
_exptl_crystal_F_000              3472
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.347
_shelx_estimated_absorpt_T_min    0.934
_shelx_estimated_absorpt_T_max    0.934
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.797
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        ?
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             37117
_diffrn_reflns_av_unetI/netI      0.0758
_diffrn_reflns_av_R_equivalents   0.0818
_diffrn_reflns_limit_h_min        -55
_diffrn_reflns_limit_h_max        55
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -29
_diffrn_reflns_limit_l_max        29
_diffrn_reflns_theta_min          2.999
_diffrn_reflns_theta_max          27.484
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.996
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.996
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.996
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              9097
_reflns_number_gt                 5937
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     ?
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0471P)²+0.8588P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          9097
_refine_ls_number_parameters      517
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0929
_refine_ls_R_factor_gt            0.0525
_refine_ls_wR_factor_ref          0.1170
_refine_ls_wR_factor_gt           0.1038
_refine_ls_goodness_of_fit_ref    1.019
_refine_ls_restrained_S_all       1.019
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C29 C 0.09173(6) 0.2370(3) 0.36649(11) 0.0269(6) Uani 1 1 d . . . . .
C30 C 0.08913(6) 0.3890(3) 0.38485(13) 0.0343(6) Uani 1 1 d . . . . .
H30 H 0.079142 0.461347 0.353435 0.041 Uiso 1 1 calc R U . . .
C31 C 0.10096(6) 0.4288(3) 0.44715(13) 0.0316(6) Uani 1 1 d . . . . .
H31 H 0.098996 0.528335 0.457519 0.038 Uiso 1 1 calc R U . . .
C32 C 0.11633(6) 0.3228(3) 0.49729(12) 0.0253(6) Uani 1 1 d . . . . .
C33 C 0.12849(6) 0.3615(3) 0.56164(12) 0.0312(6) Uani 1 1 d . . . . .
H33 H 0.127174 0.460726 0.573128 0.037 Uiso 1 1 calc R U . . .
C34 C 0.14252(6) 0.2536(3) 0.60868(12) 0.0329(6) Uani 1 1 d . . . . .
H34 H 0.150522 0.281509 0.651416 0.039 Uiso 1 1 calc R U . . .
C35 C 0.14484(6) 0.1055(3) 0.59323(12) 0.0299(6) Uani 1 1 d . . . . .
H35 H 0.154243 0.034722 0.625572 0.036 Uiso 1 1 calc R U . . .
C36 C 0.13328(6) 0.0611(3) 0.52987(11) 0.0232(5) Uani 1 1 d . . . . .
C37 C 0.13551(6) -0.0909(3) 0.51095(12) 0.0303(6) Uani 1 1 d . . . . .
H37 H 0.144685 -0.164048 0.542321 0.036 Uiso 1 1 calc R U . . .
C38 C 0.12486(6) -0.1301(3) 0.44991(13) 0.0310(6) Uani 1 1 d . . . . .
H38 H 0.127289 -0.229423 0.439828 0.037 Uiso 1 1 calc R U . . .
C39 C 0.10966(6) -0.0232(3) 0.39903(12) 0.0251(6) Uani 1 1 d . . . . .
C40 C 0.09821(6) -0.0621(3) 0.33507(12) 0.0336(6) Uani 1 1 d . . . . .
H40 H 0.100254 -0.160882 0.323901 0.040 Uiso 1 1 calc R U . . .
C41 C 0.08376(7) 0.0446(3) 0.28765(13) 0.0380(7) Uani 1 1 d . . . . .
H41 H 0.076197 0.016612 0.244993 0.046 Uiso 1 1 calc R U . . .
C42 C 0.08046(6) 0.1909(3) 0.30285(12) 0.0361(7) Uani 1 1 d . . . . .
H42 H 0.070568 0.260773 0.270282 0.043 Uiso 1 1 calc R U . . .
C43 C 0.10672(6) 0.1286(3) 0.41530(11) 0.0220(5) Uani 1 1 d . . . . .
C44 C 0.11881(6) 0.1708(3) 0.48079(11) 0.0208(5) Uani 1 1 d . . . . .
Cl1 Cl 0.03900(2) 0.65258(7) 0.23691(3) 0.03210(17) Uani 1 1 d . . . . .
Cl2 Cl 0.14923(2) 0.43438(7) 0.20717(3) 0.02848(16) Uani 1 1 d . . . . .
O1 O 0.00136(4) 0.43055(18) 0.14016(8) 0.0282(4) Uani 1 1 d . . . . .
H1 H -0.007847 0.358648 0.117197 0.042 Uiso 1 1 calc R U . . .
O2 O 0.09899(4) 0.25334(19) 0.10676(8) 0.0311(4) Uani 1 1 d . . . . .
H2 H 0.084268 0.200532 0.080357 0.047 Uiso 1 1 calc R U . . .
C7 C 0.03513(6) 0.4303(3) 0.15345(11) 0.0213(5) Uani 1 1 d . . . . .
C8 C 0.05657(6) 0.5309(2) 0.19928(11) 0.0215(5) Uani 1 1 d . . . . .
C9 C 0.09145(6) 0.5321(3) 0.21555(11) 0.0226(5) Uani 1 1 d . . . . .
H9 H 0.105508 0.597566 0.246905 0.027 Uiso 1 1 calc R U . . .
C10 C 0.10547(6) 0.4363(3) 0.18543(11) 0.0208(5) Uani 1 1 d . . . . .
C11 C 0.08457(6) 0.3390(3) 0.13742(11) 0.0213(5) Uani 1 1 d . . . . .
C12 C 0.04976(6) 0.3368(2) 0.12312(11) 0.0218(5) Uani 1 1 d . . . . .
H12 H 0.035769 0.270344 0.092152 0.026 Uiso 1 1 calc R U . . .
Cl3 Cl 0.21849(2) 0.27185(8) 0.21401(3) 0.03723(18) Uani 1 1 d . . . . .
Cl4 Cl 0.34675(2) 0.38423(7) 0.23559(3) 0.03100(16) Uani 1 1 d . . . . .
O3 O 0.21856(4) 0.0435(2) 0.12444(9) 0.0354(5) Uani 1 1 d . . . . .
H3 H 0.218830 -0.015829 0.097258 0.053 Uiso 1 1 calc R U . . .
O4 O 0.33236(4) 0.14334(19) 0.14121(8) 0.0281(4) Uani 1 1 d . . . . .
H4 H 0.327330 0.075155 0.114900 0.042 Uiso 1 1 calc R U . . .
C1 C 0.30574(6) 0.1698(3) 0.15749(11) 0.0219(5) Uani 1 1 d . . . . .
C2 C 0.30896(6) 0.2820(3) 0.20209(10) 0.0222(5) Uani 1 1 d . . . . .
C3 C 0.28254(6) 0.3125(3) 0.22007(11) 0.0246(5) Uani 1 1 d . . . . .
H3A H 0.285008 0.387214 0.250013 0.029 Uiso 1 1 calc R U . . .
C4 C 0.25243(6) 0.2321(3) 0.19353(11) 0.0243(5) Uani 1 1 d . . . . .
C5 C 0.24852(6) 0.1187(3) 0.14911(11) 0.0244(5) Uani 1 1 d . . . . .
C6 C 0.27521(6) 0.0902(3) 0.13169(11) 0.0251(6) Uani 1 1 d . . . . .
H6 H 0.272694 0.015482 0.101738 0.030 Uiso 1 1 calc R U . . .
N1 N 0.02741(5) 0.1845(2) 0.43765(9) 0.0215(4) Uani 1 1 d . . . . .
N2 N 0.05231(5) -0.0574(2) 0.51781(9) 0.0227(4) Uani 1 1 d . . . . .
C13 C 0.01265(6) 0.0319(3) 0.34227(11) 0.0306(6) Uani 1 1 d . . . . .
H13A H 0.003709 0.127034 0.322942 0.046 Uiso 1 1 calc R U . . .
H13B H -0.005430 -0.041314 0.328798 0.046 Uiso 1 1 calc R U . . .
H13C H 0.030365 0.000092 0.329407 0.046 Uiso 1 1 calc R U . . .
C14 C 0.02715(5) 0.0470(3) 0.41337(11) 0.0207(5) Uani 1 1 d . . . . .
C15 C 0.04012(6) -0.0754(3) 0.45442(11) 0.0213(5) Uani 1 1 d . . . . .
C16 C 0.04063(7) -0.2311(3) 0.42960(12) 0.0328(6) Uani 1 1 d . . . . .
H16A H 0.050655 -0.299105 0.464885 0.049 Uiso 1 1 calc R U . . .
H16B H 0.053930 -0.231377 0.404481 0.049 Uiso 1 1 calc R U . . .
H16C H 0.017613 -0.262295 0.403569 0.049 Uiso 1 1 calc R U . . .
C17 C 0.06461(7) 0.0940(3) 0.61296(11) 0.0346(6) Uani 1 1 d . . . . .
H17A H 0.046123 0.124887 0.623803 0.052 Uiso 1 1 calc R U . . .
H17B H 0.082625 0.167400 0.628199 0.052 Uiso 1 1 calc R U . . .
H17C H 0.073248 -0.001372 0.632454 0.052 Uiso 1 1 calc R U . . .
C18 C 0.05186(6) 0.0801(3) 0.54168(11) 0.0226(5) Uani 1 1 d . . . . .
C19 C 0.03936(6) 0.2023(3) 0.50104(11) 0.0211(5) Uani 1 1 d . . . . .
C20 C 0.03843(7) 0.3573(3) 0.52550(12) 0.0324(6) Uani 1 1 d . . . . .
H20A H 0.033111 0.428254 0.491226 0.049 Uiso 1 1 calc R U . . .
H20B H 0.060373 0.381025 0.558728 0.049 Uiso 1 1 calc R U . . .
H20C H 0.021192 0.362169 0.542236 0.049 Uiso 1 1 calc R U . . .
N3 N 0.18702(5) 0.4077(2) 0.44886(9) 0.0248(5) Uani 1 1 d . . . . .
N4 N 0.21437(5) 0.1804(2) 0.53673(9) 0.0256(5) Uani 1 1 d . . . . .
C21 C 0.17497(7) 0.2388(3) 0.35900(12) 0.0369(7) Uani 1 1 d . . . . .
H21A H 0.164118 0.328350 0.336497 0.055 Uiso 1 1 calc R U . . .
H21B H 0.158549 0.158469 0.347685 0.055 Uiso 1 1 calc R U . . .
H21C H 0.193508 0.211744 0.347625 0.055 Uiso 1 1 calc R U . . .
C22 C 0.18857(6) 0.2664(3) 0.42941(11) 0.0240(5) Uani 1 1 d . . . . .
C23 C 0.20276(6) 0.1522(3) 0.47414(11) 0.0245(5) Uani 1 1 d . . . . .
C24 C 0.20581(7) -0.0055(3) 0.45395(13) 0.0353(6) Uani 1 1 d . . . . .
H24A H 0.220892 -0.007056 0.432322 0.053 Uiso 1 1 calc R U . . .
H24B H 0.183597 -0.041435 0.425653 0.053 Uiso 1 1 calc R U . . .
H24C H 0.214900 -0.069097 0.490964 0.053 Uiso 1 1 calc R U . . .
C25 C 0.22639(7) 0.3500(3) 0.62686(12) 0.0399(7) Uani 1 1 d . . . . .
H25A H 0.234335 0.257294 0.649535 0.060 Uiso 1 1 calc R U . . .
H25B H 0.208581 0.391155 0.637389 0.060 Uiso 1 1 calc R U . . .
H25C H 0.245081 0.419908 0.638800 0.060 Uiso 1 1 calc R U . . .
C26 C 0.21262(6) 0.3212(3) 0.55635(11) 0.0251(5) Uani 1 1 d . . . . .
C27 C 0.19902(6) 0.4361(3) 0.51159(11) 0.0236(5) Uani 1 1 d . . . . .
C28 C 0.19736(7) 0.5950(3) 0.53174(13) 0.0376(7) Uani 1 1 d . . . . .
H28A H 0.220099 0.630365 0.557233 0.056 Uiso 1 1 calc R U . . .
H28B H 0.183800 0.599157 0.556358 0.056 Uiso 1 1 calc R U . . .
H28C H 0.187102 0.657329 0.494552 0.056 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
C29 C42 1.398(3) . ?
C29 C43 1.417(3) . ?
C29 C30 1.434(4) . ?
C30 C31 1.353(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.423(3) . ?
C31 H31 0.9300 . ?
C32 C33 1.392(3) . ?
C32 C44 1.420(3) . ?
C33 C34 1.384(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.379(3) . ?
C34 H34 0.9300 . ?
C35 C36 1.387(3) . ?
C35 H35 0.9300 . ?
C36 C44 1.426(3) . ?
C36 C37 1.435(3) . ?
C37 C38 1.329(3) . ?
C37 H37 0.9300 . ?
C38 C39 1.438(3) . ?
C38 H38 0.9300 . ?
C39 C40 1.387(3) . ?
C39 C43 1.421(3) . ?
C40 C41 1.384(4) . ?
C40 H40 0.9300 . ?
C41 C42 1.370(4) . ?
C41 H41 0.9300 . ?
C42 H42 0.9300 . ?
C43 C44 1.424(3) . ?
Cl1 C8 1.734(2) . ?
Cl2 C10 1.728(2) . ?
O1 C7 1.347(3) . ?
O1 H1 0.8200 . ?
O2 C11 1.345(3) . ?
O2 H2 0.8200 . ?
C7 C12 1.386(3) . ?
C7 C8 1.400(3) . ?
C8 C9 1.381(3) . ?
C9 C10 1.378(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.399(3) . ?
C11 C12 1.386(3) . ?
C12 H12 0.9300 . ?
Cl3 C4 1.733(2) . ?
Cl4 C2 1.736(2) . ?
O3 C5 1.347(3) . ?
O3 H3 0.8200 . ?
O4 C1 1.355(3) . ?
O4 H4 0.8200 . ?
C1 C6 1.387(3) . ?
C1 C2 1.395(3) . ?
C2 C3 1.377(3) . ?
C3 C4 1.378(3) . ?
C3 H3A 0.9300 . ?
C4 C5 1.395(3) . ?
C5 C6 1.377(3) . ?
C6 H6 0.9300 . ?
N1 C19 1.339(3) . ?
N1 C14 1.342(3) . ?
N2 C15 1.338(3) . ?
N2 C18 1.343(3) . ?
C13 C14 1.495(3) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.398(3) . ?
C15 C16 1.501(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.502(3) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.389(3) . ?
C19 C20 1.496(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N3 C27 1.339(3) . ?
N3 C22 1.345(3) . ?
N4 C23 1.337(3) . ?
N4 C26 1.344(3) . ?
C21 C22 1.496(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 C23 1.394(3) . ?
C23 C24 1.500(3) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C26 1.499(3) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 C27 1.396(3) . ?
C27 C28 1.498(3) . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C42 C29 C43 118.4(2) . . ?
C42 C29 C30 123.2(2) . . ?
C43 C29 C30 118.3(2) . . ?
C31 C30 C29 121.1(2) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 122.0(2) . . ?
C30 C31 H31 119.0 . . ?
C32 C31 H31 119.0 . . ?
C33 C32 C44 118.8(2) . . ?
C33 C32 C31 122.8(2) . . ?
C44 C32 C31 118.4(2) . . ?
C34 C33 C32 120.6(2) . . ?
C34 C33 H33 119.7 . . ?
C32 C33 H33 119.7 . . ?
C35 C34 C33 121.1(2) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C34 C35 C36 120.6(2) . . ?
C34 C35 H35 119.7 . . ?
C36 C35 H35 119.7 . . ?
C35 C36 C44 119.1(2) . . ?
C35 C36 C37 123.0(2) . . ?
C44 C36 C37 117.9(2) . . ?
C38 C37 C36 121.9(2) . . ?
C38 C37 H37 119.0 . . ?
C36 C37 H37 119.0 . . ?
C37 C38 C39 121.8(2) . . ?
C37 C38 H38 119.1 . . ?
C39 C38 H38 119.1 . . ?
C40 C39 C43 118.9(2) . . ?
C40 C39 C38 122.7(2) . . ?
C43 C39 C38 118.4(2) . . ?
C41 C40 C39 120.7(3) . . ?
C41 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
C42 C41 C40 120.8(3) . . ?
C42 C41 H41 119.6 . . ?
C40 C41 H41 119.6 . . ?
C41 C42 C29 121.1(3) . . ?
C41 C42 H42 119.4 . . ?
C29 C42 H42 119.4 . . ?
C29 C43 C39 120.0(2) . . ?
C29 C43 C44 120.4(2) . . ?
C39 C43 C44 119.6(2) . . ?
C32 C44 C43 119.8(2) . . ?
C32 C44 C36 119.8(2) . . ?
C43 C44 C36 120.4(2) . . ?
C7 O1 H1 109.5 . . ?
C11 O2 H2 109.5 . . ?
O1 C7 C12 123.2(2) . . ?
O1 C7 C8 118.8(2) . . ?
C12 C7 C8 118.0(2) . . ?
C9 C8 C7 120.7(2) . . ?
C9 C8 Cl1 119.97(18) . . ?
C7 C8 Cl1 119.27(17) . . ?
C10 C9 C8 120.1(2) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 Cl2 120.14(18) . . ?
C11 C10 Cl2 119.30(18) . . ?
O2 C11 C12 123.0(2) . . ?
O2 C11 C10 118.7(2) . . ?
C12 C11 C10 118.3(2) . . ?
C7 C12 C11 122.2(2) . . ?
C7 C12 H12 118.9 . . ?
C11 C12 H12 118.9 . . ?
C5 O3 H3 109.5 . . ?
C1 O4 H4 109.5 . . ?
O4 C1 C6 122.9(2) . . ?
O4 C1 C2 118.9(2) . . ?
C6 C1 C2 118.2(2) . . ?
C3 C2 C1 120.8(2) . . ?
C3 C2 Cl4 119.49(18) . . ?
C1 C2 Cl4 119.69(18) . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3A 120.1 . . ?
C4 C3 H3A 120.1 . . ?
C3 C4 C5 120.7(2) . . ?
C3 C4 Cl3 120.53(18) . . ?
C5 C4 Cl3 118.75(18) . . ?
O3 C5 C6 123.0(2) . . ?
O3 C5 C4 118.5(2) . . ?
C6 C5 C4 118.5(2) . . ?
C5 C6 C1 121.9(2) . . ?
C5 C6 H6 119.0 . . ?
C1 C6 H6 119.0 . . ?
C19 N1 C14 119.5(2) . . ?
C15 N2 C18 119.17(19) . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 119.8(2) . . ?
N1 C14 C13 117.7(2) . . ?
C15 C14 C13 122.5(2) . . ?
N2 C15 C14 120.6(2) . . ?
N2 C15 C16 117.5(2) . . ?
C14 C15 C16 121.8(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N2 C18 C19 120.3(2) . . ?
N2 C18 C17 117.3(2) . . ?
C19 C18 C17 122.3(2) . . ?
N1 C19 C18 120.5(2) . . ?
N1 C19 C20 117.4(2) . . ?
C18 C19 C20 122.2(2) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C27 N3 C22 118.9(2) . . ?
C23 N4 C26 119.2(2) . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C22 C23 120.2(2) . . ?
N3 C22 C21 117.5(2) . . ?
C23 C22 C21 122.3(2) . . ?
N4 C23 C22 120.8(2) . . ?
N4 C23 C24 117.7(2) . . ?
C22 C23 C24 121.4(2) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 H25A 109.5 . . ?
C26 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C26 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N4 C26 C27 120.0(2) . . ?
N4 C26 C25 118.0(2) . . ?
C27 C26 C25 122.0(2) . . ?
N3 C27 C26 120.9(2) . . ?
N3 C27 C28 117.6(2) . . ?
C26 C27 C28 121.5(2) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
 
loop_
 _geom_torsion_atom_site_label_1
 _geom_torsion_atom_site_label_2
 _geom_torsion_atom_site_label_3
 _geom_torsion_atom_site_label_4
 _geom_torsion
 _geom_torsion_site_symmetry_1
 _geom_torsion_site_symmetry_2
 _geom_torsion_site_symmetry_3
 _geom_torsion_site_symmetry_4
 _geom_torsion_publ_flag
C42 C29 C30 C31 -178.8(2) . . . . ?
C43 C29 C30 C31 0.7(4) . . . . ?
C29 C30 C31 C32 -0.3(4) . . . . ?
C30 C31 C32 C33 -179.7(2) . . . . ?
C30 C31 C32 C44 -0.7(4) . . . . ?
C44 C32 C33 C34 -0.4(4) . . . . ?
C31 C32 C33 C34 178.5(2) . . . . ?
C32 C33 C34 C35 0.0(4) . . . . ?
C33 C34 C35 C36 0.4(4) . . . . ?
C34 C35 C36 C44 -0.2(3) . . . . ?
C34 C35 C36 C37 179.0(2) . . . . ?
C35 C36 C37 C38 -178.7(2) . . . . ?
C44 C36 C37 C38 0.6(3) . . . . ?
C36 C37 C38 C39 -1.5(4) . . . . ?
C37 C38 C39 C40 -179.6(2) . . . . ?
C37 C38 C39 C43 1.2(3) . . . . ?
C43 C39 C40 C41 -0.7(3) . . . . ?
C38 C39 C40 C41 -180.0(2) . . . . ?
C39 C40 C41 C42 0.0(4) . . . . ?
C40 C41 C42 C29 0.4(4) . . . . ?
C43 C29 C42 C41 0.0(4) . . . . ?
C30 C29 C42 C41 179.4(2) . . . . ?
C42 C29 C43 C39 -0.7(3) . . . . ?
C30 C29 C43 C39 179.8(2) . . . . ?
C42 C29 C43 C44 179.5(2) . . . . ?
C30 C29 C43 C44 0.0(3) . . . . ?
C40 C39 C43 C29 1.1(3) . . . . ?
C38 C39 C43 C29 -179.7(2) . . . . ?
C40 C39 C43 C44 -179.1(2) . . . . ?
C38 C39 C43 C44 0.1(3) . . . . ?
C33 C32 C44 C43 -179.6(2) . . . . ?
C31 C32 C44 C43 1.4(3) . . . . ?
C33 C32 C44 C36 0.5(3) . . . . ?
C31 C32 C44 C36 -178.4(2) . . . . ?
C29 C43 C44 C32 -1.0(3) . . . . ?
C39 C43 C44 C32 179.2(2) . . . . ?
C29 C43 C44 C36 178.8(2) . . . . ?
C39 C43 C44 C36 -1.0(3) . . . . ?
C35 C36 C44 C32 -0.2(3) . . . . ?
C37 C36 C44 C32 -179.5(2) . . . . ?
C35 C36 C44 C43 180.0(2) . . . . ?
C37 C36 C44 C43 0.7(3) . . . . ?
O1 C7 C8 C9 178.4(2) . . . . ?
C12 C7 C8 C9 -2.7(3) . . . . ?
O1 C7 C8 Cl1 -0.4(3) . . . . ?
C12 C7 C8 Cl1 178.57(17) . . . . ?
C7 C8 C9 C10 1.7(3) . . . . ?
Cl1 C8 C9 C10 -179.52(17) . . . . ?
C8 C9 C10 C11 1.1(3) . . . . ?
C8 C9 C10 Cl2 -178.36(17) . . . . ?
C9 C10 C11 O2 176.4(2) . . . . ?
Cl2 C10 C11 O2 -4.2(3) . . . . ?
C9 C10 C11 C12 -2.8(3) . . . . ?
Cl2 C10 C11 C12 176.61(17) . . . . ?
O1 C7 C12 C11 179.7(2) . . . . ?
C8 C7 C12 C11 0.9(3) . . . . ?
O2 C11 C12 C7 -177.3(2) . . . . ?
C10 C11 C12 C7 1.9(3) . . . . ?
O4 C1 C2 C3 -179.9(2) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
O4 C1 C2 Cl4 -0.1(3) . . . . ?
C6 C1 C2 Cl4 179.99(17) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
Cl4 C2 C3 C4 179.82(17) . . . . ?
C2 C3 C4 C5 0.7(4) . . . . ?
C2 C3 C4 Cl3 -178.40(18) . . . . ?
C3 C4 C5 O3 -179.9(2) . . . . ?
Cl3 C4 C5 O3 -0.7(3) . . . . ?
C3 C4 C5 C6 -0.9(4) . . . . ?
Cl3 C4 C5 C6 178.26(18) . . . . ?
O3 C5 C6 C1 179.6(2) . . . . ?
C4 C5 C6 C1 0.7(4) . . . . ?
O4 C1 C6 C5 179.8(2) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
C19 N1 C14 C15 -1.6(3) . . . . ?
C19 N1 C14 C13 178.31(19) . . . . ?
C18 N2 C15 C14 0.2(3) . . . . ?
C18 N2 C15 C16 -179.2(2) . . . . ?
N1 C14 C15 N2 1.1(3) . . . . ?
C13 C14 C15 N2 -178.8(2) . . . . ?
N1 C14 C15 C16 -179.6(2) . . . . ?
C13 C14 C15 C16 0.5(3) . . . . ?
C15 N2 C18 C19 -1.0(3) . . . . ?
C15 N2 C18 C17 177.8(2) . . . . ?
C14 N1 C19 C18 0.8(3) . . . . ?
C14 N1 C19 C20 -178.8(2) . . . . ?
N2 C18 C19 N1 0.5(3) . . . . ?
C17 C18 C19 N1 -178.3(2) . . . . ?
N2 C18 C19 C20 -179.9(2) . . . . ?
C17 C18 C19 C20 1.4(3) . . . . ?
C27 N3 C22 C23 -0.6(3) . . . . ?
C27 N3 C22 C21 -179.9(2) . . . . ?
C26 N4 C23 C22 -0.9(3) . . . . ?
C26 N4 C23 C24 178.7(2) . . . . ?
N3 C22 C23 N4 1.4(3) . . . . ?
C21 C22 C23 N4 -179.3(2) . . . . ?
N3 C22 C23 C24 -178.1(2) . . . . ?
C21 C22 C23 C24 1.2(3) . . . . ?
C23 N4 C26 C27 -0.4(3) . . . . ?
C23 N4 C26 C25 -178.9(2) . . . . ?
C22 N3 C27 C26 -0.7(3) . . . . ?
C22 N3 C27 C28 179.2(2) . . . . ?
N4 C26 C27 N3 1.2(3) . . . . ?
C25 C26 C27 N3 179.7(2) . . . . ?
N4 C26 C27 C28 -178.7(2) . . . . ?
C25 C26 C27 C28 -0.2(4) . . . . ?
 
_refine_diff_density_max    0.282
_refine_diff_density_min   -0.352
_refine_diff_density_rms    0.064


 
data_30CRES-PHE-PYR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C84 H54 Cl4 N4 O4' 
_chemical_formula_weight          1325.11

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            15
_space_group_name_H-M_alt         'C 2/c'
_space_group_name_Hall            '-C 2yc'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y, -z+1/2'
 'x+1/2, y+1/2, z'
 '-x+1/2, y+1/2, -z+1/2'
 '-x, -y, -z'
 'x, -y, z-1/2'
 '-x+1/2, -y+1/2, -z'
 'x+1/2, -y+1/2, z-1/2'
 
_cell_length_a                    33.873(7)
_cell_length_b                    10.374(2)
_cell_length_c                    18.332(4)
_cell_angle_alpha                 90
_cell_angle_beta                  91.186(6)
_cell_angle_gamma                 90
_cell_volume                      6441(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     15951
_cell_measurement_theta_min       3.0
_cell_measurement_theta_max       28.3
 
_exptl_crystal_description        'Prism'
_exptl_crystal_colour             Red
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.367          
_exptl_crystal_F_000              2744
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.243
_shelx_estimated_absorpt_T_min    0.953
_shelx_estimated_absorpt_T_max    0.953
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.651
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             32417
_diffrn_reflns_av_unetI/netI      0.1127
_diffrn_reflns_av_R_equivalents   0.1362
_diffrn_reflns_limit_h_min        -43
_diffrn_reflns_limit_h_max        43
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.017
_diffrn_reflns_theta_max          27.485
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              7363
_reflns_number_gt                 2992
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0680P)²+1.3656P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          7363
_refine_ls_number_parameters      435
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.2010
_refine_ls_R_factor_gt            0.0776
_refine_ls_wR_factor_ref          0.2050
_refine_ls_wR_factor_gt           0.1610
_refine_ls_goodness_of_fit_ref    1.048
_refine_ls_restrained_S_all       1.048
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl1 Cl 0.39237(3) -0.02075(13) 0.77470(7) 0.0796(4) Uani 1 1 d . . . . .
Cl2 Cl 0.43057(3) 0.47769(13) 0.72874(7) 0.0818(4) Uani 1 1 d . . . . .
O2 O 0.32313(8) 0.0394(3) 0.68232(15) 0.0575(8) Uani 1 1 d . . . . .
H2 H 0.304329 0.060846 0.656152 0.086 Uiso 1 1 calc R U . . .
O1 O 0.35872(8) 0.4805(3) 0.63652(15) 0.0606(8) Uani 1 1 d . . . . .
H1 H 0.340178 0.474161 0.607270 0.091 Uiso 1 1 calc R U . . .
N2 N 0.23957(9) 0.4064(3) 0.42075(15) 0.0415(8) Uani 1 1 d . . . . .
N1 N 0.29864(9) 0.4416(3) 0.53032(16) 0.0423(8) Uani 1 1 d . . . . .
C1 C 0.34774(11) 0.1408(4) 0.69182(19) 0.0430(9) Uani 1 1 d . . . . .
C13 C 0.27801(11) 0.4102(3) 0.40435(19) 0.0399(9) Uani 1 1 d . . . . .
C5 C 0.36541(11) 0.3647(4) 0.6689(2) 0.0462(10) Uani 1 1 d . . . . .
C35 C 0.24525(11) 0.7561(3) 0.53758(17) 0.0369(8) Uani 1 1 d . . . . .
C7 C 0.26012(11) 0.4357(3) 0.54723(19) 0.0399(9) Uani 1 1 d . . . . .
C36 C 0.27587(11) 0.7687(3) 0.59090(19) 0.0418(9) Uani 1 1 d . . . . .
C12 C 0.23020(10) 0.4177(3) 0.4916(2) 0.0398(9) Uani 1 1 d . . . . .
C18 C 0.30786(11) 0.4278(3) 0.4593(2) 0.0439(9) Uani 1 1 d . . . . .
C6 C 0.34050(10) 0.2599(4) 0.65868(18) 0.0424(9) Uani 1 1 d . . . . .
H6 H 0.318190 0.269216 0.628719 0.051 Uiso 1 1 calc R U . . .
C8 C 0.24820(12) 0.4483(3) 0.62101(19) 0.0472(10) Uani 1 1 d . . . . .
H8 H 0.267182 0.460218 0.657768 0.057 Uiso 1 1 calc R U . . .
C40 C 0.20562(11) 0.7568(3) 0.55845(19) 0.0436(9) Uani 1 1 d . . . . .
C11 C 0.19009(11) 0.4125(4) 0.5123(2) 0.0490(10) Uani 1 1 d . . . . .
H11 H 0.170336 0.401096 0.476923 0.059 Uiso 1 1 calc R U . . .
C2 C 0.38121(11) 0.1279(4) 0.73623(19) 0.0498(11) Uani 1 1 d . . . . .
C9 C 0.20972(13) 0.4431(4) 0.6381(2) 0.0546(11) Uani 1 1 d . . . . .
H9 H 0.202452 0.452098 0.686480 0.066 Uiso 1 1 calc R U . . .
C37 C 0.26599(14) 0.7825(4) 0.6635(2) 0.0534(11) Uani 1 1 d . . . . .
H37 H 0.285887 0.792659 0.698774 0.064 Uiso 1 1 calc R U . . .
C14 C 0.28971(12) 0.3974(4) 0.3310(2) 0.0517(11) Uani 1 1 d . . . . .
H14 H 0.270686 0.387313 0.294125 0.062 Uiso 1 1 calc R U . . .
C41 C 0.17529(12) 0.7442(4) 0.5037(2) 0.0535(11) Uani 1 1 d . . . . .
H41 H 0.148997 0.744284 0.517347 0.064 Uiso 1 1 calc R U . . .
C4 C 0.39868(10) 0.3490(5) 0.7146(2) 0.0527(11) Uani 1 1 d . . . . .
C42 C 0.18394(12) 0.7324(4) 0.4331(2) 0.0523(11) Uani 1 1 d . . . . .
H42 H 0.163494 0.724801 0.398678 0.063 Uiso 1 1 calc R U . . .
C3 C 0.40611(11) 0.2316(5) 0.7473(2) 0.0564(12) Uani 1 1 d . . . . .
H3 H 0.428329 0.222149 0.777512 0.068 Uiso 1 1 calc R U . . .
C38 C 0.22718(15) 0.7813(4) 0.6842(2) 0.0602(12) Uani 1 1 d . . . . .
H38 H 0.221352 0.788557 0.733379 0.072 Uiso 1 1 calc R U . . .
C39 C 0.19692(13) 0.7695(4) 0.6338(2) 0.0543(11) Uani 1 1 d . . . . .
H39 H 0.170851 0.769922 0.648715 0.065 Uiso 1 1 calc R U . . .
C10 C 0.18038(13) 0.4241(4) 0.5836(2) 0.0574(11) Uani 1 1 d . . . . .
H10 H 0.154017 0.419375 0.596506 0.069 Uiso 1 1 calc R U . . .
C15 C 0.32835(14) 0.3997(4) 0.3143(2) 0.0628(12) Uani 1 1 d . . . . .
H15 H 0.335631 0.389713 0.265945 0.075 Uiso 1 1 calc R U . . .
C17 C 0.34773(12) 0.4301(4) 0.4397(2) 0.0606(12) Uani 1 1 d . . . . .
H17 H 0.367349 0.440669 0.475468 0.073 Uiso 1 1 calc R U . . .
C16 C 0.35771(13) 0.4168(4) 0.3685(3) 0.0688(13) Uani 1 1 d . . . . .
H16 H 0.384142 0.419128 0.355821 0.083 Uiso 1 1 calc R U . . .
C33 C 0.45405(11) 0.8518(5) 0.4665(3) 0.0607(12) Uani 1 1 d . . . . .
C34 C 0.45977(11) 0.9794(5) 0.4404(2) 0.0630(13) Uani 1 1 d . . . . .
C26 C 0.44068(14) 1.0853(6) 0.4745(3) 0.0745(14) Uani 1 1 d . . . . .
C22 C 0.48449(14) 0.9996(7) 0.3804(3) 0.0807(16) Uani 1 1 d . . . . .
C27 C 0.41760(14) 1.0609(7) 0.5355(3) 0.0857(17) Uani 1 1 d . . . . .
H27 H 0.405238 1.129847 0.558037 0.103 Uiso 1 1 calc R U . . .
C29 C 0.43037(13) 0.8328(6) 0.5294(3) 0.0704(14) Uani 1 1 d . . . . .
C19 C 0.47245(15) 0.7471(7) 0.4325(3) 0.0814(16) Uani 1 1 d . . . . .
C28 C 0.41266(14) 0.9435(7) 0.5624(3) 0.0872(17) Uani 1 1 d . . . . .
H28 H 0.397401 0.932595 0.603563 0.105 Uiso 1 1 calc R U . . .
C21 C 0.50326(17) 0.8920(10) 0.3485(3) 0.108(3) Uani 1 1 d . . . . .
H21 H 0.520197 0.905375 0.309987 0.130 Uiso 1 1 calc R U . . .
C25 C 0.44672(18) 1.2105(6) 0.4460(4) 0.101(2) Uani 1 1 d . . . . .
H25 H 0.434344 1.281426 0.466570 0.121 Uiso 1 1 calc R U . . .
C23 C 0.49019(19) 1.1257(10) 0.3554(3) 0.111(2) Uani 1 1 d . . . . .
H23 H 0.506939 1.141068 0.316744 0.134 Uiso 1 1 calc R U . . .
C20 C 0.49739(19) 0.7734(9) 0.3720(4) 0.110(3) Uani 1 1 d . . . . .
H20 H 0.509738 0.705148 0.348744 0.132 Uiso 1 1 calc R U . . .
C32 C 0.46591(19) 0.6220(7) 0.4598(5) 0.110(2) Uani 1 1 d . . . . .
H32 H 0.476841 0.550659 0.437048 0.132 Uiso 1 1 calc R U . . .
C24 C 0.4711(2) 1.2260(8) 0.3876(5) 0.121(3) Uani 1 1 d . . . . .
H24 H 0.474857 1.308570 0.369253 0.145 Uiso 1 1 calc R U . . .
C30 C 0.42580(17) 0.7089(8) 0.5550(4) 0.106(2) Uani 1 1 d . . . . .
H30 H 0.410780 0.694581 0.596092 0.128 Uiso 1 1 calc R U . . .
C31 C 0.4431(2) 0.6064(8) 0.5208(5) 0.126(3) Uani 1 1 d . . . . .
H31 H 0.439289 0.523935 0.539242 0.152 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl1 C2 1.734(4) . ?
Cl2 C4 1.733(4) . ?
O2 C1 1.352(4) . ?
O2 H2 0.8200 . ?
O1 C5 1.357(4) . ?
O1 H1 0.8200 . ?
N2 C13 1.343(4) . ?
N2 C12 1.348(4) . ?
N1 C7 1.349(4) . ?
N1 C18 1.353(4) . ?
C1 C2 1.389(5) . ?
C1 C6 1.396(5) . ?
C13 C14 1.416(5) . ?
C13 C18 1.424(5) . ?
C5 C6 1.386(5) . ?
C5 C4 1.400(5) . ?
C35 C40 1.404(5) . ?
C35 C36 1.416(5) . ?
C35 C35 1.427(6) 7_566 ?
C7 C8 1.426(5) . ?
C7 C12 1.435(5) . ?
C36 C37 1.387(5) . ?
C36 C42 1.439(5) 7_566 ?
C12 C11 1.419(5) . ?
C18 C17 1.405(5) . ?
C6 H6 0.9300 . ?
C8 C9 1.348(5) . ?
C8 H8 0.9300 . ?
C40 C39 1.424(5) . ?
C40 C41 1.427(5) . ?
C11 C10 1.359(5) . ?
C11 H11 0.9300 . ?
C2 C3 1.380(5) . ?
C9 C10 1.409(5) . ?
C9 H9 0.9300 . ?
C37 C38 1.375(5) . ?
C37 H37 0.9300 . ?
C14 C15 1.351(5) . ?
C14 H14 0.9300 . ?
C41 C42 1.339(5) . ?
C41 H41 0.9300 . ?
C4 C3 1.379(6) . ?
C42 H42 0.9300 . ?
C3 H3 0.9300 . ?
C38 C39 1.371(5) . ?
C38 H38 0.9300 . ?
C39 H39 0.9300 . ?
C10 H10 0.9300 . ?
C15 C16 1.404(6) . ?
C15 H15 0.9300 . ?
C17 C16 1.362(5) . ?
C17 H17 0.9300 . ?
C16 H16 0.9300 . ?
C33 C19 1.404(6) . ?
C33 C34 1.423(6) . ?
C33 C29 1.432(6) . ?
C34 C22 1.412(6) . ?
C34 C26 1.425(6) . ?
C26 C27 1.401(7) . ?
C26 C25 1.417(7) . ?
C22 C23 1.401(8) . ?
C22 C21 1.416(8) . ?
C27 C28 1.326(7) . ?
C27 H27 0.9300 . ?
C29 C30 1.378(7) . ?
C29 C28 1.435(7) . ?
C19 C32 1.411(8) . ?
C19 C20 1.433(8) . ?
C28 H28 0.9300 . ?
C21 C20 1.321(8) . ?
C21 H21 0.9300 . ?
C25 C24 1.376(8) . ?
C25 H25 0.9300 . ?
C23 C24 1.365(9) . ?
C23 H23 0.9300 . ?
C20 H20 0.9300 . ?
C32 C31 1.382(9) . ?
C32 H32 0.9300 . ?
C24 H24 0.9300 . ?
C30 C31 1.371(9) . ?
C30 H30 0.9300 . ?
C31 H31 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C1 O2 H2 109.5 . . ?
C5 O1 H1 109.5 . . ?
C13 N2 C12 117.5(3) . . ?
C7 N1 C18 117.4(3) . . ?
O2 C1 C2 119.6(4) . . ?
O2 C1 C6 122.0(3) . . ?
C2 C1 C6 118.4(4) . . ?
N2 C13 C14 120.1(3) . . ?
N2 C13 C18 121.5(3) . . ?
C14 C13 C18 118.4(4) . . ?
O1 C5 C6 122.7(3) . . ?
O1 C5 C4 119.3(4) . . ?
C6 C5 C4 118.0(4) . . ?
C40 C35 C36 120.1(3) . . ?
C40 C35 C35 120.0(4) . 7_566 ?
C36 C35 C35 119.9(4) . 7_566 ?
N1 C7 C8 120.5(3) . . ?
N1 C7 C12 121.0(3) . . ?
C8 C7 C12 118.5(4) . . ?
C37 C36 C35 119.0(4) . . ?
C37 C36 C42 122.8(4) . 7_566 ?
C35 C36 C42 118.2(3) . 7_566 ?
N2 C12 C11 120.0(3) . . ?
N2 C12 C7 121.3(3) . . ?
C11 C12 C7 118.7(3) . . ?
N1 C18 C17 119.1(4) . . ?
N1 C18 C13 121.3(3) . . ?
C17 C18 C13 119.6(4) . . ?
C5 C6 C1 122.3(3) . . ?
C5 C6 H6 118.9 . . ?
C1 C6 H6 118.9 . . ?
C9 C8 C7 120.7(4) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C35 C40 C39 118.9(4) . . ?
C35 C40 C41 119.1(3) . . ?
C39 C40 C41 122.0(4) . . ?
C10 C11 C12 120.4(4) . . ?
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C3 C2 C1 120.0(4) . . ?
C3 C2 Cl1 120.4(3) . . ?
C1 C2 Cl1 119.5(3) . . ?
C8 C9 C10 120.8(4) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C38 C37 C36 121.0(4) . . ?
C38 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
C15 C14 C13 120.4(4) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C42 C41 C40 121.3(4) . . ?
C42 C41 H41 119.3 . . ?
C40 C41 H41 119.3 . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 Cl2 120.5(3) . . ?
C5 C4 Cl2 119.5(4) . . ?
C41 C42 C36 121.5(4) . 7_566 ?
C41 C42 H42 119.2 . . ?
C36 C42 H42 119.2 7_566 . ?
C4 C3 C2 121.3(4) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C39 C38 C37 121.4(4) . . ?
C39 C38 H38 119.3 . . ?
C37 C38 H38 119.3 . . ?
C38 C39 C40 119.7(4) . . ?
C38 C39 H39 120.2 . . ?
C40 C39 H39 120.2 . . ?
C11 C10 C9 120.9(4) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C14 C15 C16 121.1(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C16 C17 C18 120.2(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C16 C15 120.4(4) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C19 C33 C34 120.4(5) . . ?
C19 C33 C29 120.8(5) . . ?
C34 C33 C29 118.8(5) . . ?
C22 C34 C33 119.2(5) . . ?
C22 C34 C26 120.6(6) . . ?
C33 C34 C26 120.2(5) . . ?
C27 C26 C25 123.1(6) . . ?
C27 C26 C34 118.5(5) . . ?
C25 C26 C34 118.3(6) . . ?
C23 C22 C34 118.8(6) . . ?
C23 C22 C21 122.3(7) . . ?
C34 C22 C21 118.9(6) . . ?
C28 C27 C26 122.7(6) . . ?
C28 C27 H27 118.7 . . ?
C26 C27 H27 118.7 . . ?
C30 C29 C33 118.1(6) . . ?
C30 C29 C28 123.5(6) . . ?
C33 C29 C28 118.4(5) . . ?
C33 C19 C32 118.6(6) . . ?
C33 C19 C20 118.1(6) . . ?
C32 C19 C20 123.3(7) . . ?
C27 C28 C29 121.4(5) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C20 C21 C22 121.9(7) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 H21 119.0 . . ?
C24 C25 C26 119.1(7) . . ?
C24 C25 H25 120.4 . . ?
C26 C25 H25 120.4 . . ?
C24 C23 C22 120.0(7) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C21 C20 C19 121.6(7) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C31 C32 C19 119.3(7) . . ?
C31 C32 H32 120.4 . . ?
C19 C32 H32 120.4 . . ?
C23 C24 C25 123.1(8) . . ?
C23 C24 H24 118.5 . . ?
C25 C24 H24 118.5 . . ?
C31 C30 C29 121.0(7) . . ?
C31 C30 H30 119.5 . . ?
C29 C30 H30 119.5 . . ?
C30 C31 C32 122.0(8) . . ?
C30 C31 H31 119.0 . . ?
C32 C31 H31 119.0 . . ?
 
_refine_diff_density_max    0.259
_refine_diff_density_min   -0.343
_refine_diff_density_rms    0.055


 
data_31CRES-DMP-PYR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C28 H22 Cl2 N2 O2' 
_chemical_formula_weight          489.37

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.8453(13)
_cell_length_b                    10.4891(15)
_cell_length_c                    12.6940(19)
_cell_angle_alpha                 94.129(7)
_cell_angle_beta                  94.866(7)
_cell_angle_gamma                 98.239(7)
_cell_volume                      1157.1(3)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     10718
_cell_measurement_theta_min       3.2
_cell_measurement_theta_max       27.6
 
_exptl_crystal_description        'Prism'
_exptl_crystal_colour             'Colorless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.405          
_exptl_crystal_F_000              508
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.310
_shelx_estimated_absorpt_T_min    0.941
_shelx_estimated_absorpt_T_max    0.941
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.800
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             12258
_diffrn_reflns_av_unetI/netI      0.0426
_diffrn_reflns_av_R_equivalents   0.0323
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        11
_diffrn_reflns_limit_k_min        -13
_diffrn_reflns_limit_k_max        13
_diffrn_reflns_limit_l_min        -16
_diffrn_reflns_limit_l_max        16
_diffrn_reflns_theta_min          3.223
_diffrn_reflns_theta_max          27.484
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.997
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.997
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.997
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              5291
_reflns_number_gt                 4119
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0838P)²+0.2470P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          5291
_refine_ls_number_parameters      311
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0599
_refine_ls_R_factor_gt            0.0428
_refine_ls_wR_factor_ref          0.1471
_refine_ls_wR_factor_gt           0.1188
_refine_ls_goodness_of_fit_ref    1.078
_refine_ls_restrained_S_all       1.078
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl01 Cl 1.02959(6) 0.68667(6) 0.08882(4) 0.03253(16) Uani 1 1 d . . . . .
Cl02 Cl 1.11357(6) 0.23705(5) 0.24945(4) 0.03074(16) Uani 1 1 d . . . . .
O2 O 0.93694(17) 0.32455(14) 0.41690(12) 0.0285(3) Uani 1 1 d . . . . .
H2 H 0.859281 0.332969 0.446050 0.043 Uiso 1 1 calc R U . . .
O1 O 0.84868(17) 0.72004(15) 0.26951(13) 0.0291(4) Uani 1 1 d . . . . .
H1 H 0.787264 0.719435 0.314426 0.044 Uiso 1 1 calc R U . . .
N1 N 0.66632(19) 0.34726(16) 0.50690(13) 0.0218(4) Uani 1 1 d . . . . .
N2 N 0.39818(19) 0.30727(16) 0.60654(13) 0.0214(4) Uani 1 1 d . . . . .
C24 C 0.5297(2) 0.32823(18) 0.44994(16) 0.0211(4) Uani 1 1 d . . . . .
C27 C 0.5353(2) 0.32621(18) 0.66345(16) 0.0207(4) Uani 1 1 d . . . . .
C26 C 0.6687(2) 0.34588(19) 0.61191(16) 0.0212(4) Uani 1 1 d . . . . .
H26 H 0.763077 0.358546 0.652424 0.025 Uiso 1 1 calc R U . . .
C2 C 0.9548(2) 0.41021(19) 0.34255(16) 0.0220(4) Uani 1 1 d . . . . .
C22 C 0.4328(2) -0.01332(18) 0.46247(16) 0.0216(4) Uani 1 1 d . . . . .
C4 C 1.0627(2) 0.4679(2) 0.18094(16) 0.0252(5) Uani 1 1 d . . . . .
H4 H 1.121591 0.450104 0.125941 0.030 Uiso 1 1 calc R U . . .
C6 C 0.9108(2) 0.6100(2) 0.26842(16) 0.0224(4) Uani 1 1 d . . . . .
C14 C 0.5053(2) 0.0681(2) 0.01210(15) 0.0236(4) Uani 1 1 d . . . . .
C3 C 1.0399(2) 0.3818(2) 0.25794(17) 0.0233(4) Uani 1 1 d . . . . .
C5 C 0.9981(2) 0.5796(2) 0.18580(16) 0.0239(4) Uani 1 1 d . . . . .
C25 C 0.3962(2) 0.30791(19) 0.50115(16) 0.0232(4) Uani 1 1 d . . . . .
H25 H 0.301945 0.294239 0.460407 0.028 Uiso 1 1 calc R U . . .
C1 C 0.8940(2) 0.5248(2) 0.34687(16) 0.0236(4) Uani 1 1 d . . . . .
H1A H 0.840331 0.545386 0.404086 0.028 Uiso 1 1 calc R U . . .
C23 C 0.5253(3) 0.3302(2) 0.33194(16) 0.0272(5) Uani 1 1 d . . . . .
H23A H 0.552130 0.417458 0.314233 0.041 Uiso 1 1 calc R U . . .
H23B H 0.423828 0.296163 0.300171 0.041 Uiso 1 1 calc R U . . .
H23C H 0.597139 0.278119 0.305729 0.041 Uiso 1 1 calc R U . . .
C13 C 0.3727(3) 0.1291(2) 0.00019(17) 0.0289(5) Uani 1 1 d . . . . .
C17 C 0.4491(3) -0.01394(19) 0.35222(17) 0.0263(5) Uani 1 1 d . . . . .
C15 C 0.7259(3) 0.0354(2) 0.38824(18) 0.0295(5) Uani 1 1 d . . . . .
H15 H 0.822237 0.050610 0.363411 0.035 Uiso 1 1 calc R U . . .
C28 C 0.5403(3) 0.3277(2) 0.78120(17) 0.0292(5) Uani 1 1 d . . . . .
H28A H 0.507648 0.405628 0.809350 0.044 Uiso 1 1 calc R U . . .
H28B H 0.643272 0.324378 0.810329 0.044 Uiso 1 1 calc R U . . .
H28C H 0.473176 0.254202 0.799760 0.044 Uiso 1 1 calc R U . . .
C20 C 0.1564(3) -0.0670(2) 0.42490(19) 0.0309(5) Uani 1 1 d . . . . .
H20 H 0.059246 -0.086203 0.447883 0.037 Uiso 1 1 calc R U . . .
C9 C 0.6502(2) 0.1428(2) 0.04835(16) 0.0280(5) Uani 1 1 d . . . . .
C16 C 0.6004(3) 0.0107(2) 0.31812(18) 0.0287(5) Uani 1 1 d . . . . .
H16 H 0.611820 0.009630 0.245921 0.034 Uiso 1 1 calc R U . . .
C21 C 0.2854(2) -0.03872(18) 0.49956(17) 0.0246(4) Uani 1 1 d . . . . .
C7 C 0.7712(3) -0.0503(3) 0.03708(19) 0.0359(6) Uani 1 1 d . . . . .
H7 H 0.859079 -0.089127 0.045646 0.043 Uiso 1 1 calc R U . . .
C10 C 0.6580(3) 0.2758(2) 0.07180(18) 0.0361(6) Uani 1 1 d . . . . .
H10 H 0.751888 0.325325 0.096226 0.043 Uiso 1 1 calc R U . . .
C19 C 0.1722(3) -0.0667(2) 0.3173(2) 0.0328(5) Uani 1 1 d . . . . .
H19 H 0.085368 -0.084739 0.268892 0.039 Uiso 1 1 calc R U . . .
C18 C 0.3157(3) -0.0398(2) 0.28101(18) 0.0295(5) Uani 1 1 d . . . . .
H18 H 0.323884 -0.038831 0.208505 0.035 Uiso 1 1 calc R U . . .
C8 C 0.7821(3) 0.0782(3) 0.05991(18) 0.0346(5) Uani 1 1 d . . . . .
H8 H 0.877172 0.126070 0.083677 0.041 Uiso 1 1 calc R U . . .
C12 C 0.3877(3) 0.2629(2) 0.02408(18) 0.0375(6) Uani 1 1 d . . . . .
H12 H 0.301626 0.304159 0.016175 0.045 Uiso 1 1 calc R U . . .
C11 C 0.5291(3) 0.3348(2) 0.05935(18) 0.0405(6) Uani 1 1 d . . . . .
H11 H 0.536959 0.423676 0.074749 0.049 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl01 C5 1.738(2) . ?
Cl02 C3 1.736(2) . ?
O2 C2 1.353(2) . ?
O2 H2 0.8200 . ?
O1 C6 1.347(2) . ?
O1 H1 0.8200 . ?
N1 C26 1.333(3) . ?
N1 C24 1.336(3) . ?
N2 C25 1.337(3) . ?
N2 C27 1.339(3) . ?
C24 C25 1.393(3) . ?
C24 C23 1.497(3) . ?
C27 C26 1.394(3) . ?
C27 C28 1.490(3) . ?
C26 H26 0.9300 . ?
C2 C1 1.385(3) . ?
C2 C3 1.402(3) . ?
C22 C17 1.419(3) . ?
C22 C21 1.419(3) . ?
C22 C22 1.440(4) 2_656 ?
C4 C5 1.375(3) . ?
C4 C3 1.385(3) . ?
C4 H4 0.9300 . ?
C6 C1 1.388(3) . ?
C6 C5 1.399(3) . ?
C14 C13 1.416(3) . ?
C14 C9 1.424(3) . ?
C14 C14 1.428(4) 2_655 ?
C25 H25 0.9300 . ?
C1 H1A 0.9300 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C13 C12 1.400(3) . ?
C13 C7 1.438(3) 2_655 ?
C17 C18 1.405(3) . ?
C17 C16 1.435(3) . ?
C15 C16 1.345(3) . ?
C15 C21 1.434(3) 2_656 ?
C15 H15 0.9300 . ?
C28 H28A 0.9600 . ?
C28 H28B 0.9600 . ?
C28 H28C 0.9600 . ?
C20 C19 1.384(3) . ?
C20 C21 1.403(3) . ?
C20 H20 0.9300 . ?
C9 C10 1.396(3) . ?
C9 C8 1.433(3) . ?
C16 H16 0.9300 . ?
C7 C8 1.346(4) . ?
C7 H7 0.9300 . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C19 C18 1.386(3) . ?
C19 H19 0.9300 . ?
C18 H18 0.9300 . ?
C8 H8 0.9300 . ?
C12 C11 1.385(4) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C2 O2 H2 109.5 . . ?
C6 O1 H1 109.5 . . ?
C26 N1 C24 117.85(17) . . ?
C25 N2 C27 117.60(17) . . ?
N1 C24 C25 119.68(18) . . ?
N1 C24 C23 118.42(18) . . ?
C25 C24 C23 121.90(18) . . ?
N2 C27 C26 119.64(18) . . ?
N2 C27 C28 118.54(18) . . ?
C26 C27 C28 121.81(19) . . ?
N1 C26 C27 122.63(18) . . ?
N1 C26 H26 118.7 . . ?
C27 C26 H26 118.7 . . ?
O2 C2 C1 122.99(18) . . ?
O2 C2 C3 118.29(18) . . ?
C1 C2 C3 118.71(19) . . ?
C17 C22 C21 120.72(19) . . ?
C17 C22 C22 119.6(2) . 2_656 ?
C21 C22 C22 119.7(2) . 2_656 ?
C5 C4 C3 120.02(18) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
O1 C6 C1 122.95(18) . . ?
O1 C6 C5 119.27(18) . . ?
C1 C6 C5 117.78(19) . . ?
C13 C14 C9 120.0(2) . . ?
C13 C14 C14 120.4(2) . 2_655 ?
C9 C14 C14 119.6(2) . 2_655 ?
C4 C3 C2 120.07(19) . . ?
C4 C3 Cl02 120.46(16) . . ?
C2 C3 Cl02 119.46(16) . . ?
C4 C5 C6 121.31(19) . . ?
C4 C5 Cl01 119.12(16) . . ?
C6 C5 Cl01 119.55(17) . . ?
N2 C25 C24 122.61(18) . . ?
N2 C25 H25 118.7 . . ?
C24 C25 H25 118.7 . . ?
C2 C1 C6 122.03(19) . . ?
C2 C1 H1A 119.0 . . ?
C6 C1 H1A 119.0 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 C13 C14 118.7(2) . . ?
C12 C13 C7 123.0(2) . 2_655 ?
C14 C13 C7 118.2(2) . 2_655 ?
C18 C17 C22 118.3(2) . . ?
C18 C17 C16 122.9(2) . . ?
C22 C17 C16 118.9(2) . . ?
C16 C15 C21 121.5(2) . 2_656 ?
C16 C15 H15 119.2 . . ?
C21 C15 H15 119.2 2_656 . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C19 C20 C21 120.6(2) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C10 C9 C14 118.8(2) . . ?
C10 C9 C8 122.6(2) . . ?
C14 C9 C8 118.6(2) . . ?
C15 C16 C17 121.5(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
C20 C21 C22 118.6(2) . . ?
C20 C21 C15 122.5(2) . 2_656 ?
C22 C21 C15 118.84(19) . 2_656 ?
C8 C7 C13 121.7(2) . 2_655 ?
C8 C7 H7 119.1 . . ?
C13 C7 H7 119.1 2_655 . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C20 C19 C18 120.8(2) . . ?
C20 C19 H19 119.6 . . ?
C18 C19 H19 119.6 . . ?
C19 C18 C17 120.9(2) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C7 C8 C9 121.4(2) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C11 C12 C13 120.9(2) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C10 C11 C12 120.5(2) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
 
_refine_diff_density_max    0.375
_refine_diff_density_min   -0.356
_refine_diff_density_rms    0.074


 
data_32CRES-TMP-PHE-PYR
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C80 H66 Cl8 N8 O8' 
_chemical_formula_weight          1551.00

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0033   0.0016
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H'  'H'   0.0000   0.0000
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'Cl'  'Cl'   0.1484   0.1585
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N'  'N'   0.0061   0.0033
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0106   0.0060
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       monoclinic
_space_group_IT_number            4
_space_group_name_H-M_alt         'P 21'
_space_group_name_Hall            'P 2yb'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, y+1/2, -z'
 
_cell_length_a                    17.219(5)
_cell_length_b                    22.693(7)
_cell_length_c                    18.331(5)
_cell_angle_alpha                 90
_cell_angle_beta                  91.312(6)
_cell_angle_gamma                 90
_cell_volume                      7161(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     16938
_cell_measurement_theta_min       3.1
_cell_measurement_theta_max       27.8
 
_exptl_crystal_description        Block
_exptl_crystal_colour             Yellow
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.439          
_exptl_crystal_F_000              3208
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.200
_exptl_crystal_size_mid           0.200
_exptl_crystal_size_min           0.200
_exptl_absorpt_coefficient_mu     0.380
_shelx_estimated_absorpt_T_min    0.928
_shelx_estimated_absorpt_T_max    0.928
_exptl_absorpt_correction_type    'Multi-scan'
_exptl_absorpt_correction_T_min   0.453
_exptl_absorpt_correction_T_max   1.000
_exptl_absorpt_process_details    'Jacobson, R. (1998) Private communication'
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71075
_diffrn_radiation_type            MoK\a
_diffrn_source                    'Sealed Tube'
_diffrn_measurement_device_type   'Rigaku Mercury375R (2x2 bin mode)'
_diffrn_measurement_method        'profile data from ω-scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             59375
_diffrn_reflns_av_unetI/netI      0.1593
_diffrn_reflns_av_R_equivalents   0.1068
_diffrn_reflns_limit_h_min        -22
_diffrn_reflns_limit_h_max        22
_diffrn_reflns_limit_k_min        -29
_diffrn_reflns_limit_k_max        29
_diffrn_reflns_limit_l_min        -23
_diffrn_reflns_limit_l_max        23
_diffrn_reflns_theta_min          3.073
_diffrn_reflns_theta_max          27.485
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.986
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.986
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.926
_diffrn_reflns_point_group_measured_fraction_full  0.956
_reflns_number_total              30424
_reflns_number_gt                 16751
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.832
_reflns_Friedel_fraction_max      0.864
_reflns_Friedel_fraction_full     0.913
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        ?
_computing_cell_refinement        ?
_computing_data_reduction         ?
_computing_structure_solution     'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1617P)²+25.0287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_abs_structure_details
;
 Flack x determined using 4452 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    0.29(6)
_chemical_absolute_configuration  ?
_refine_ls_number_reflns          30424
_refine_ls_number_parameters      1889
_refine_ls_number_restraints      1
_refine_ls_R_factor_all           0.1864
_refine_ls_R_factor_gt            0.1229
_refine_ls_wR_factor_ref          0.3590
_refine_ls_wR_factor_gt           0.3145
_refine_ls_goodness_of_fit_ref    1.026
_refine_ls_restrained_S_all       1.026
_refine_ls_shift/su_max           0.000
_refine_ls_shift/su_mean          0.000
 
loop_
 _atom_site_label
 _atom_site_type_symbol
 _atom_site_fract_x
 _atom_site_fract_y
 _atom_site_fract_z
 _atom_site_U_iso_or_equiv
 _atom_site_adp_type
 _atom_site_occupancy
 _atom_site_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
Cl01 Cl 1.1263(3) 0.28918(18) 0.2565(2) 0.0533(11) Uani 1 1 d . . . . .
Cl02 Cl 0.7011(3) 0.70734(18) 0.6768(3) 0.0537(11) Uani 1 1 d . . . . .
Cl03 Cl 0.0865(3) 0.74664(17) 1.0546(2) 0.0516(10) Uani 1 1 d . . . . .
Cl04 Cl 0.5665(3) 0.26764(19) 0.3663(2) 0.0565(11) Uani 1 1 d . . . . .
Cl05 Cl 0.6340(3) 0.74659(18) -0.1301(2) 0.0540(11) Uani 1 1 d . . . . .
Cl06 Cl 0.1375(3) 0.73408(19) 0.7646(2) 0.0542(11) Uani 1 1 d . . . . .
Cl07 Cl 0.6033(3) 0.27509(19) 1.1733(2) 0.0547(11) Uani 1 1 d . . . . .
Cl08 Cl 0.0983(3) 0.26074(19) 0.4477(3) 0.0586(12) Uani 1 1 d . . . . .
Cl09 Cl 1.1165(3) 0.72645(19) 0.2806(3) 0.0558(11) Uani 1 1 d . . . . .
Cl0A Cl 0.1112(3) 0.27331(19) 0.7434(3) 0.0594(12) Uani 1 1 d . . . . .
Cl0B Cl 0.6509(3) 0.25345(18) 0.6512(2) 0.0546(11) Uani 1 1 d . . . . .
Cl0C Cl 1.1484(3) 0.26634(18) -0.0362(2) 0.0527(11) Uani 1 1 d . . . . .
Cl0D Cl 0.6127(3) 0.74278(19) 0.3957(2) 0.0579(12) Uani 1 1 d . . . . .
Cl0E Cl 0.5468(3) 0.7304(2) 0.1518(3) 0.0594(12) Uani 1 1 d . . . . .
Cl0F Cl 1.1660(3) 0.73085(19) 0.5721(3) 0.0602(12) Uani 1 1 d . . . . .
Cl0G Cl 0.6869(3) 0.27278(19) 0.8911(3) 0.0594(12) Uani 1 1 d . . . . .
O00H O 1.0265(6) 0.6219(4) 0.3114(6) 0.043(3) Uani 1 1 d . . . . .
H00H H 0.999635 0.593196 0.321054 0.064 Uiso 1 1 calc R U . . .
O00I O 0.5169(6) 0.6373(5) 0.4171(6) 0.045(3) Uani 1 1 d . . . . .
H00I H 0.489699 0.608669 0.425989 0.067 Uiso 1 1 calc R U . . .
O00J O 0.5923(6) 0.6086(5) 0.6695(6) 0.044(3) Uani 1 1 d . . . . .
H00J H 0.563070 0.580190 0.665376 0.066 Uiso 1 1 calc R U . . .
O00K O 0.7371(7) 0.6470(5) -0.0916(6) 0.048(3) Uani 1 1 d . . . . .
H00K H 0.765647 0.619853 -0.078548 0.071 Uiso 1 1 calc R U . . .
O00L O 0.6615(6) 0.6354(5) 0.1607(6) 0.043(3) Uani 1 1 d . . . . .
H00L H 0.694214 0.609116 0.160919 0.064 Uiso 1 1 calc R U . . .
O00M O 0.1889(6) 0.6455(5) 1.0643(6) 0.046(3) Uani 1 1 d . . . . .
H00M H 0.216945 0.616288 1.064427 0.069 Uiso 1 1 calc R U . . .
O00N O 1.0615(7) 0.6282(5) 0.5725(6) 0.053(3) Uani 1 1 d . . . . .
H00N H 1.033690 0.598907 0.570458 0.079 Uiso 1 1 calc R U . . .
O00O O 1.0289(7) 0.3895(5) 0.2196(5) 0.047(3) Uani 1 1 d . . . . .
H00O H 1.001202 0.417602 0.208305 0.070 Uiso 1 1 calc R U . . .
O00P O 1.0462(6) 0.3699(4) -0.0407(6) 0.043(3) Uani 1 1 d . . . . .
H00P H 1.017748 0.398819 -0.040490 0.064 Uiso 1 1 calc R U . . .
N00Q N 0.3035(6) 0.5542(5) 1.0630(6) 0.028(2) Uani 1 1 d . . . . .
O00R O 0.6653(6) 0.3733(5) 0.3695(6) 0.041(2) Uani 1 1 d . . . . .
H00R H 0.692787 0.402681 0.372649 0.062 Uiso 1 1 calc R U . . .
N00S N 0.4193(7) 0.5417(5) 0.4492(7) 0.033(3) Uani 1 1 d . . . . .
O00T O 0.5816(7) 0.3739(5) 0.8771(6) 0.047(3) Uani 1 1 d . . . . .
H00T H 0.551519 0.401925 0.874789 0.070 Uiso 1 1 calc R U . . .
O00U O 0.2113(7) 0.3563(5) 0.4566(6) 0.050(3) Uani 1 1 d . . . . .
H00U H 0.243220 0.382918 0.461154 0.075 Uiso 1 1 calc R U . . .
N00V N 0.8326(7) 0.5555(5) -0.0494(6) 0.032(3) Uani 1 1 d . . . . .
N00W N 0.3367(7) 0.5404(6) 0.8540(7) 0.040(3) Uani 1 1 d . . . . .
O00X O 0.2283(7) 0.6313(5) 0.8059(6) 0.052(3) Uani 1 1 d . . . . .
H00X H 0.254003 0.602806 0.819639 0.079 Uiso 1 1 calc R U . . .
O00Y O 0.7378(6) 0.3617(5) 0.6243(6) 0.046(3) Uani 1 1 d . . . . .
H00Y H 0.763883 0.390418 0.613010 0.069 Uiso 1 1 calc R U . . .
N00Z N 0.9121(8) 0.5415(5) 0.3496(7) 0.038(3) Uani 1 1 d . . . . .
N010 N 0.4601(8) 0.4590(6) 0.8689(6) 0.038(3) Uani 1 1 d . . . . .
O011 O 0.5127(7) 0.3792(5) 1.1308(6) 0.049(3) Uani 1 1 d . . . . .
H011 H 0.486832 0.407511 1.116793 0.074 Uiso 1 1 calc R U . . .
O012 O 0.2231(8) 0.3688(5) 0.7181(6) 0.057(3) Uani 1 1 d . . . . .
H012 H 0.254222 0.394672 0.707759 0.086 Uiso 1 1 calc R U . . .
N013 N 0.9387(7) 0.4663(5) -0.0315(6) 0.034(3) Uani 1 1 d . . . . .
N014 N 0.7844(7) 0.4629(5) 0.3729(6) 0.033(3) Uani 1 1 d . . . . .
N015 N 0.8375(7) 0.4504(5) 0.5877(6) 0.034(3) Uani 1 1 d . . . . .
N016 N 0.9478(8) 0.5360(6) 0.5635(7) 0.042(3) Uani 1 1 d . . . . .
N017 N 0.7883(7) 0.5530(6) 0.1625(7) 0.039(3) Uani 1 1 d . . . . .
N018 N 0.3153(7) 0.4514(5) 0.4723(7) 0.036(3) Uani 1 1 d . . . . .
N019 N 0.4671(7) 0.5262(6) 0.6652(7) 0.037(3) Uani 1 1 d . . . . .
C01A C 0.1768(9) 0.6641(6) 0.9948(8) 0.031(3) Uani 1 1 d . . . . .
C01B C 0.9089(8) 0.5656(6) -0.0537(7) 0.028(3) Uani 1 1 d . . . . .
C01C C 0.9634(9) 0.5199(7) -0.0449(8) 0.037(3) Uani 1 1 d . . . . .
C01D C 1.0739(8) 0.6489(6) 0.5023(8) 0.032(3) Uani 1 1 d . . . . .
C01E C 1.0368(8) 0.3803(6) 0.0887(8) 0.035(3) Uani 1 1 d . . . . .
H01E H 1.004580 0.412885 0.082045 0.042 Uiso 1 1 calc R U . . .
C01F C 0.1202(10) 0.7335(6) 0.9106(9) 0.045(4) Uani 1 1 d . . . . .
H01F H 0.089461 0.766540 0.901823 0.054 Uiso 1 1 calc R U . . .
C01G C 0.8610(8) 0.5722(7) 0.1568(8) 0.034(3) Uani 1 1 d . . . . .
C01H C 0.7754(8) 0.5208(6) 0.3584(7) 0.030(3) Uani 1 1 d . . . . .
C01I C 0.8384(9) 0.5605(6) 0.3462(7) 0.035(3) Uani 1 1 d . . . . .
C01J C 0.9255(8) 0.5301(6) 0.1631(8) 0.032(3) Uani 1 1 d . . . . .
N01K N 0.4148(7) 0.4692(6) 1.0801(7) 0.038(3) Uani 1 1 d . . . . .
C01L C 0.1410(9) 0.2996(6) 0.6590(9) 0.041(4) Uani 1 1 d . . . . .
C01M C 0.5462(9) 0.3768(7) 1.0034(8) 0.037(3) Uani 1 1 d . . . . .
H01M H 0.513202 0.408544 0.994284 0.045 Uiso 1 1 calc R U . . .
C01N C 0.1936(9) 0.3435(6) 0.6549(8) 0.033(3) Uani 1 1 d . . . . .
C01O C 0.6101(8) 0.2690(6) 0.5087(8) 0.036(3) Uani 1 1 d . . . . .
H01O H 0.579572 0.235460 0.513691 0.044 Uiso 1 1 calc R U . . .
C01P C 0.6976(9) 0.4734(6) 0.1837(9) 0.038(3) Uani 1 1 d . . . . .
H01P H 0.655269 0.498167 0.175490 0.046 Uiso 1 1 calc R U . . .
C01Q C 0.6982(8) 0.3402(6) 0.5626(8) 0.034(3) Uani 1 1 d . . . . .
N01R N 0.9139(7) 0.4735(6) 0.1792(7) 0.038(3) Uani 1 1 d . . . . .
C01S C 0.3437(8) 0.5529(6) 0.4472(7) 0.031(3) Uani 1 1 d . . . . .
N01T N 0.3410(7) 0.4504(6) 0.6852(7) 0.040(3) Uani 1 1 d . . . . .
C01U C 1.1367(9) 0.7207(6) 0.4273(9) 0.043(4) Uani 1 1 d . . . . .
H01U H 1.169084 0.753341 0.423358 0.051 Uiso 1 1 calc R U . . .
C01V C 0.5950(8) 0.6379(6) 0.6042(8) 0.034(3) Uani 1 1 d . . . . .
C01W C 0.3798(10) 0.6086(7) 0.6447(8) 0.043(4) Uani 1 1 d . . . . .
H01W H 0.420666 0.634823 0.638955 0.051 Uiso 1 1 calc R U . . .
C01X C 1.0556(9) 0.6449(6) 0.3727(8) 0.037(3) Uani 1 1 d . . . . .
C01Y C 0.4117(9) 0.5570(7) 0.8456(8) 0.039(4) Uani 1 1 d . . . . .
C01Z C 0.6604(9) 0.3484(6) 0.4341(8) 0.034(3) Uani 1 1 d . . . . .
C020 C 0.8239(11) 0.6210(7) 0.3298(9) 0.047(4) Uani 1 1 d . . . . .
H020 H 0.865435 0.646239 0.321979 0.057 Uiso 1 1 calc R U . . .
C021 C 0.1977(9) 0.4862(8) 1.0777(9) 0.044(4) Uani 1 1 d . . . . .
H02B H 0.170631 0.522125 1.087804 0.066 Uiso 1 1 calc R U . . .
H02C H 0.188443 0.458153 1.115799 0.066 Uiso 1 1 calc R U . . .
H02D H 0.179422 0.470426 1.031874 0.066 Uiso 1 1 calc R U . . .
C022 C 0.4745(8) 0.5157(7) 0.8581(8) 0.034(3) Uani 1 1 d . . . . .
C023 C 0.3345(9) 0.5275(7) 1.2613(7) 0.037(3) Uani 1 1 d . . . . .
C024 C 0.7004(9) 0.6404(6) 0.0350(8) 0.036(3) Uani 1 1 d . . . . .
H024 H 0.735249 0.609632 0.042775 0.043 Uiso 1 1 calc R U . . .
C025 C 0.6559(9) 0.6597(7) 0.0925(9) 0.039(4) Uani 1 1 d . . . . .
C026 C 0.4357(9) 0.5232(7) 1.0662(8) 0.039(3) Uani 1 1 d . . . . .
C027 C 1.0544(9) 0.3631(6) 0.1583(8) 0.033(3) Uani 1 1 d . . . . .
C028 C 0.3946(8) 0.5474(7) 0.6599(8) 0.037(3) Uani 1 1 d . . . . .
C029 C 0.6424(8) 0.7143(6) -0.0441(9) 0.038(3) Uani 1 1 d . . . . .
C02A C 0.1970(9) 0.4973(7) 1.2691(8) 0.038(3) Uani 1 1 d . . . . .
H02A H 0.144379 0.506059 1.264680 0.045 Uiso 1 1 calc R U . . .
C02B C 0.2174(8) 0.3647(7) 0.5873(8) 0.039(4) Uani 1 1 d . . . . .
H02J H 0.252559 0.395753 0.585432 0.047 Uiso 1 1 calc R U . . .
C02C C 0.7771(9) 0.4948(7) 0.1773(8) 0.036(3) Uani 1 1 d . . . . .
C02D C 1.0038(9) 0.5505(7) 0.1544(8) 0.040(4) Uani 1 1 d . . . . .
H02H H 1.045435 0.524523 0.158774 0.048 Uiso 1 1 calc R U . . .
C02E C 0.9242(9) 0.4838(6) 0.3674(8) 0.036(3) Uani 1 1 d . . . . .
C02F C 0.8706(9) 0.5503(6) 0.5596(8) 0.035(3) Uani 1 1 d . . . . .
C02G C 0.4444(8) 0.4848(6) 0.4647(7) 0.031(3) Uani 1 1 d . . . . .
C02H C 0.8760(9) 0.6317(8) 0.1424(9) 0.045(4) Uani 1 1 d . . . . .
H02I H 0.835045 0.658222 0.137659 0.053 Uiso 1 1 calc R U . . .
C02I C 0.3793(9) 0.5673(6) 1.0580(8) 0.035(3) Uani 1 1 d . . . . .
C02J C 0.3849(9) 0.4437(6) 0.8744(8) 0.034(3) Uani 1 1 d . . . . .
C02K C 0.4285(8) 0.6207(7) 0.8306(9) 0.040(4) Uani 1 1 d . . . . .
H02K H 0.389383 0.648646 0.824912 0.048 Uiso 1 1 calc R U . . .
C02L C 1.0421(8) 0.6235(6) 0.4400(8) 0.036(3) Uani 1 1 d . . . . .
H02L H 1.010489 0.590525 0.444489 0.043 Uiso 1 1 calc R U . . .
C02M C 0.1886(9) 0.3393(6) 0.5220(8) 0.035(3) Uani 1 1 d . . . . .
C02N C 0.8606(8) 0.4440(6) 0.3775(7) 0.031(3) Uani 1 1 d . . . . .
C02O C 0.6024(8) 0.7052(6) 0.0830(9) 0.037(3) Uani 1 1 d . . . . .
C02P C 0.1979(9) 0.6585(6) 0.8642(8) 0.037(3) Uani 1 1 d . . . . .
C02Q C 0.7023(8) 0.3713(7) 0.4957(9) 0.039(3) Uani 1 1 d . . . . .
H02Q H 0.731525 0.405566 0.492136 0.047 Uiso 1 1 calc R U . . .
C02R C 0.6974(9) 0.5420(8) 0.3529(8) 0.041(4) Uani 1 1 d . . . . .
H02R H 0.655328 0.517103 0.360269 0.050 Uiso 1 1 calc R U . . .
C02S C 0.8636(8) 0.5735(8) 0.7516(8) 0.038(3) Uani 1 1 d . . . . .
C02T C 0.7612(10) 0.5042(7) 0.7728(8) 0.044(4) Uani 1 1 d . . . . .
H02T H 0.708369 0.496801 0.777452 0.053 Uiso 1 1 calc R U . . .
C02U C 0.9169(8) 0.5273(7) 0.7614(7) 0.034(3) Uani 1 1 d . . . . .
C02V C 0.7313(9) 0.5207(8) 0.5699(10) 0.049(4) Uani 1 1 d . . . . .
H02E H 0.702106 0.484884 0.574502 0.073 Uiso 1 1 calc R U . . .
H02F H 0.718799 0.538839 0.523806 0.073 Uiso 1 1 calc R U . . .
H02G H 0.718551 0.547086 0.608707 0.073 Uiso 1 1 calc R U . . .
C02W C 0.6076(9) 0.7006(6) 0.4753(9) 0.038(3) Uani 1 1 d . . . . .
C02X C 0.2529(9) 0.5297(8) 0.6623(9) 0.045(4) Uani 1 1 d . . . . .
H02X H 0.211264 0.504378 0.669727 0.054 Uiso 1 1 calc R U . . .
C02Y C 1.1035(9) 0.6960(6) 0.3649(10) 0.043(4) Uani 1 1 d . . . . .
C02Z C 1.1225(10) 0.6978(6) 0.4947(10) 0.049(4) Uani 1 1 d . . . . .
C030 C 0.2911(9) 0.5068(7) 0.4596(8) 0.039(4) Uani 1 1 d . . . . .
C031 C 0.3224(9) 0.4841(7) 0.8684(8) 0.037(3) Uani 1 1 d . . . . .
C032 C 0.9664(11) 0.6422(8) 0.7288(9) 0.052(4) Uani 1 1 d . . . . .
H032 H 0.982106 0.680221 0.717302 0.062 Uiso 1 1 calc R U . . .
C033 C 0.2493(10) 0.4637(7) 0.8754(9) 0.046(4) Uani 1 1 d . . . . .
H033 H 0.208787 0.490654 0.870923 0.055 Uiso 1 1 calc R U . . .
C034 C 0.1306(9) 0.7132(7) 0.9820(9) 0.041(4) Uani 1 1 d . . . . .
C035 C 0.3320(9) 0.5082(7) 0.6675(9) 0.042(4) Uani 1 1 d . . . . .
C036 C 0.2062(9) 0.5169(9) 0.4576(9) 0.049(4) Uani 1 1 d . . . . .
H03B H 0.179772 0.479712 0.453805 0.073 Uiso 1 1 calc R U . . .
H03C H 0.192425 0.540926 0.416261 0.073 Uiso 1 1 calc R U . . .
H03D H 0.191378 0.536470 0.501573 0.073 Uiso 1 1 calc R U . . .
C037 C 0.3646(11) 0.6298(7) 1.2335(9) 0.048(4) Uani 1 1 d . . . . .
H037 H 0.401109 0.659340 1.226816 0.057 Uiso 1 1 calc R U . . .
C038 C 0.9331(11) 0.6290(7) -0.0674(9) 0.046(4) Uani 1 1 d . . . . .
H03M H 0.952901 0.632358 -0.115768 0.069 Uiso 1 1 calc R U . . .
H03N H 0.972696 0.640182 -0.032433 0.069 Uiso 1 1 calc R U . . .
H03O H 0.888906 0.654386 -0.062753 0.069 Uiso 1 1 calc R U . . .
C039 C 0.7245(8) 0.4887(8) -0.0315(9) 0.043(4) Uani 1 1 d . . . . .
H03P H 0.697568 0.525362 -0.024952 0.065 Uiso 1 1 calc R U . . .
H03Q H 0.714039 0.462955 0.008661 0.065 Uiso 1 1 calc R U . . .
H03R H 0.706926 0.470647 -0.076215 0.065 Uiso 1 1 calc R U . . .
C03A C 0.2875(11) 0.6430(7) 1.2280(8) 0.044(4) Uani 1 1 d . . . . .
H03A H 0.272040 0.681164 1.216004 0.053 Uiso 1 1 calc R U . . .
C03B C 0.8917(9) 0.4697(7) 0.7772(8) 0.039(4) Uani 1 1 d . . . . .
C03C C 0.8499(11) 0.6117(7) 0.5417(10) 0.054(4) Uani 1 1 d . . . . .
H03T H 0.896216 0.635213 0.540705 0.081 Uiso 1 1 calc R U . . .
H03V H 0.815907 0.626866 0.577955 0.081 Uiso 1 1 calc R U . . .
H03W H 0.824151 0.612944 0.494728 0.081 Uiso 1 1 calc R U . . .
C03D C 0.9695(8) 0.4821(7) 0.5779(7) 0.036(3) Uani 1 1 d . . . . .
C03E C 0.4786(9) 0.4688(7) 0.6795(8) 0.038(3) Uani 1 1 d . . . . .
C03F C 0.3180(11) 0.6140(7) 0.4339(9) 0.046(4) Uani 1 1 d . . . . .
H03E H 0.362464 0.639508 0.433296 0.070 Uiso 1 1 calc R U . . .
H03F H 0.284122 0.626067 0.471914 0.070 Uiso 1 1 calc R U . . .
H03G H 0.290773 0.616145 0.387656 0.070 Uiso 1 1 calc R U . . .
C03G C 0.8170(9) 0.5068(8) 0.5740(8) 0.040(4) Uani 1 1 d . . . . .
C03H C 0.2166(9) 0.4429(8) 1.2853(9) 0.047(4) Uani 1 1 d . . . . .
H03H H 0.177986 0.415467 1.294566 0.057 Uiso 1 1 calc R U . . .
C03I C 0.8898(10) 0.6297(9) 0.7351(9) 0.053(5) Uani 1 1 d . . . . .
H03I H 0.853612 0.659736 0.728064 0.063 Uiso 1 1 calc R U . . .
C03J C 0.5547(8) 0.6211(6) 0.5437(8) 0.035(3) Uani 1 1 d . . . . .
H03 H 0.524110 0.587418 0.545468 0.042 Uiso 1 1 calc R U . . .
C03K C 0.8080(9) 0.4998(7) -0.0343(7) 0.034(3) Uani 1 1 d . . . . .
C03L C 0.4208(11) 0.3788(7) 0.4922(10) 0.047(4) Uani 1 1 d . . . . .
H03J H 0.445560 0.378226 0.539639 0.070 Uiso 1 1 calc R U . . .
H03K H 0.457387 0.366872 0.456272 0.070 Uiso 1 1 calc R U . . .
H03L H 0.377484 0.352231 0.491363 0.070 Uiso 1 1 calc R U . . .
C03M C 0.3906(9) 0.5702(8) 1.2498(8) 0.042(4) Uani 1 1 d . . . . .
C03N C 0.6510(9) 0.7160(6) 0.5360(10) 0.045(4) Uani 1 1 d . . . . .
H0AA H 0.684527 0.747965 0.532863 0.054 Uiso 1 1 calc R U . . .
C03O C 1.0162(10) 0.6102(8) 0.1390(9) 0.049(4) Uani 1 1 d . . . . .
H03X H 1.066432 0.623607 0.131278 0.059 Uiso 1 1 calc R U . . .
C03P C 0.9523(12) 0.6513(9) 0.1351(10) 0.059(5) Uani 1 1 d . . . . .
H03Y H 0.961989 0.691158 0.127729 0.071 Uiso 1 1 calc R U . . .
C03Q C 0.6945(9) 0.6657(7) -0.0337(9) 0.043(4) Uani 1 1 d . . . . .
C03R C 0.1097(9) 0.2740(6) 0.5919(11) 0.051(5) Uani 1 1 d . . . . .
H2AA H 0.073701 0.243535 0.594077 0.062 Uiso 1 1 calc R U . . .
C03S C 0.5655(11) 0.5967(8) 0.8350(9) 0.052(4) Uani 1 1 d . . . . .
H03S H 0.615980 0.610693 0.830910 0.062 Uiso 1 1 calc R U . . .
C03T C 0.2138(9) 0.6379(7) 0.9346(8) 0.037(3) Uani 1 1 d . . . . .
H1AA H 0.248621 0.606998 0.942009 0.045 Uiso 1 1 calc R U . . .
C03U C 0.7834(10) 0.5602(8) 0.7575(9) 0.047(4) Uani 1 1 d . . . . .
H03U H 0.746330 0.589590 0.750921 0.056 Uiso 1 1 calc R U . . .
C03V C 0.5515(9) 0.3556(6) 1.0728(8) 0.038(3) Uani 1 1 d . . . . .
C03W C 0.1531(9) 0.7069(7) 0.8552(8) 0.037(3) Uani 1 1 d . . . . .
C03X C 0.8127(9) 0.4569(7) 0.7821(8) 0.038(3) Uani 1 1 d . . . . .
C03Y C 0.5865(10) 0.3542(8) 0.9462(9) 0.050(4) Uani 1 1 d . . . . .
C03Z C 0.3976(10) 0.3517(7) 1.3043(9) 0.046(4) Uani 1 1 d . . . . .
H03Z H 0.412206 0.312958 1.313708 0.055 Uiso 1 1 calc R U . . .
C040 C 0.5569(10) 0.4480(7) 0.6850(8) 0.040(4) Uani 1 1 d . . . . .
H040 H 0.598484 0.473459 0.678413 0.048 Uiso 1 1 calc R U . . .
C041 C 0.6868(9) 0.6003(7) 0.3365(10) 0.045(4) Uani 1 1 d . . . . .
H041 H 0.636181 0.614244 0.331994 0.054 Uiso 1 1 calc R U . . .
C042 C 0.6413(10) 0.2805(8) 1.0321(8) 0.046(4) Uani 1 1 d . . . . .
H042 H 0.674142 0.248714 1.041769 0.055 Uiso 1 1 calc R U . . .
C043 C 1.0217(10) 0.5976(8) 0.7397(9) 0.048(4) Uani 1 1 d . . . . .
H043 H 1.074054 0.606433 0.734945 0.057 Uiso 1 1 calc R U . . .
C044 C 0.2844(8) 0.4985(6) 1.0741(8) 0.034(3) Uani 1 1 d . . . . .
C045 C 0.8409(9) 0.4536(6) 0.1858(8) 0.036(3) Uani 1 1 d . . . . .
C046 C 1.0297(9) 0.4369(8) 0.7843(8) 0.044(4) Uani 1 1 d . . . . .
H046 H 1.066966 0.407744 0.791846 0.053 Uiso 1 1 calc R U . . .
C047 C 0.4353(10) 0.4535(7) 1.2797(8) 0.040(4) Uani 1 1 d . . . . .
C048 C 0.5574(12) 0.6531(8) 0.4778(9) 0.053(5) Uani 1 1 d . . . . .
C049 C 0.4691(11) 0.5539(8) 1.2552(9) 0.052(4) Uani 1 1 d . . . . .
H049 H 0.506773 0.582800 1.249636 0.062 Uiso 1 1 calc R U . . .
C04A C 1.0632(10) 0.3531(7) 0.0294(9) 0.045(4) Uani 1 1 d . . . . .
C04B C 0.8432(10) 0.3537(7) 0.8116(9) 0.046(4) Uani 1 1 d . . . . .
H04B H 0.826497 0.315512 0.820621 0.055 Uiso 1 1 calc R U . . .
C04C C 0.4154(9) 0.4290(7) 0.6924(8) 0.036(3) Uani 1 1 d . . . . .
C04D C 0.2496(10) 0.5429(8) 1.2582(8) 0.045(4) Uani 1 1 d . . . . .
C04E C 0.5993(10) 0.3056(8) 1.0853(9) 0.046(4) Uani 1 1 d . . . . .
C04F C 0.2324(12) 0.6004(7) 1.2399(9) 0.053(5) Uani 1 1 d . . . . .
H04F H 0.180340 0.611014 1.235293 0.064 Uiso 1 1 calc R U . . .
C04G C 0.3994(10) 0.6316(8) 1.0414(11) 0.053(5) Uani 1 1 d . . . . .
H04A H 0.414609 0.634954 0.991564 0.079 Uiso 1 1 calc R U . . .
H04C H 0.441369 0.644133 1.073089 0.079 Uiso 1 1 calc R U . . .
H04D H 0.354731 0.655894 1.049266 0.079 Uiso 1 1 calc R U . . .
C04H C 0.6881(9) 0.4176(7) 0.2017(8) 0.040(4) Uani 1 1 d . . . . .
H04P H 0.637841 0.404324 0.209193 0.048 Uiso 1 1 calc R U . . .
C04I C 0.5045(13) 0.6344(9) 0.8259(10) 0.063(5) Uani 1 1 d . . . . .
H04O H 0.516395 0.673399 0.815409 0.076 Uiso 1 1 calc R U . . .
C04J C 0.3394(9) 0.4561(6) 1.0848(8) 0.035(3) Uani 1 1 d . . . . .
C04K C 0.3936(10) 0.4384(7) 0.4758(8) 0.041(4) Uani 1 1 d . . . . .
C04L C 0.8613(9) 0.4551(6) -0.0240(7) 0.034(3) Uani 1 1 d . . . . .
C04M C 0.3189(10) 0.3931(7) 1.0972(9) 0.048(4) Uani 1 1 d . . . . .
H04E H 0.299456 0.376150 1.052419 0.072 Uiso 1 1 calc R U . . .
H04G H 0.279794 0.390662 1.133542 0.072 Uiso 1 1 calc R U . . .
H04H H 0.364341 0.371955 1.113596 0.072 Uiso 1 1 calc R U . . .
C04N C 0.6160(8) 0.2964(6) 0.4436(8) 0.035(3) Uani 1 1 d . . . . .
C04O C 0.3550(10) 0.4681(7) 1.2762(8) 0.038(4) Uani 1 1 d . . . . .
C04P C 0.6526(11) 0.2934(8) 0.5700(9) 0.049(4) Uani 1 1 d . . . . .
C04Q C 0.2954(11) 0.3626(8) 0.8948(10) 0.056(5) Uani 1 1 d . . . . .
H04Q H 0.284908 0.322858 0.902272 0.068 Uiso 1 1 calc R U . . .
C04R C 0.6473(8) 0.6867(7) 0.6010(10) 0.043(4) Uani 1 1 d . . . . .
C04S C 0.7890(12) 0.3988(8) 0.8000(8) 0.050(4) Uani 1 1 d . . . . .
H04S H 0.736371 0.390651 0.804038 0.060 Uiso 1 1 calc R U . . .
C04T C 0.3087(11) 0.6264(9) 0.6393(10) 0.055(5) Uani 1 1 d . . . . .
H04T H 0.300640 0.666355 0.630533 0.066 Uiso 1 1 calc R U . . .
C04U C 0.8347(12) 0.3931(8) -0.0052(9) 0.054(5) Uani 1 1 d . . . . .
H04L H 0.878241 0.366761 -0.005805 0.081 Uiso 1 1 calc R U . . .
H04M H 0.796070 0.380375 -0.040363 0.081 Uiso 1 1 calc R U . . .
H04N H 0.812844 0.393123 0.042558 0.081 Uiso 1 1 calc R U . . .
C04V C 0.5304(8) 0.4753(8) 0.4649(9) 0.044(4) Uani 1 1 d . . . . .
H04I H 0.543211 0.448456 0.426533 0.067 Uiso 1 1 calc R U . . .
H04J H 0.547072 0.459147 0.511027 0.067 Uiso 1 1 calc R U . . .
H04K H 0.556126 0.512276 0.457225 0.067 Uiso 1 1 calc R U . . .
C04W C 0.7525(9) 0.3750(6) 0.2108(9) 0.041(4) Uani 1 1 d . . . . .
H04W H 0.743124 0.335715 0.221881 0.049 Uiso 1 1 calc R U . . .
C04X C 0.8250(10) 0.3951(7) 0.2023(9) 0.043(4) Uani 1 1 d . . . . .
H04X H 0.866174 0.368883 0.207750 0.052 Uiso 1 1 calc R U . . .
C04Y C 1.1331(10) 0.2859(7) 0.1066(9) 0.044(4) Uani 1 1 d . . . . .
H04Y H 1.167375 0.254454 0.111684 0.052 Uiso 1 1 calc R U . . .
C04Z C 1.1115(9) 0.3038(7) 0.0412(9) 0.045(4) Uani 1 1 d . . . . .
C050 C 0.5522(9) 0.5351(8) 0.8509(9) 0.047(4) Uani 1 1 d . . . . .
H050 H 0.593579 0.508943 0.856249 0.056 Uiso 1 1 calc R U . . .
C051 C 0.9486(11) 0.3634(9) 0.3964(10) 0.055(5) Uani 1 1 d . . . . .
H051 H 0.958252 0.323802 0.406163 0.066 Uiso 1 1 calc R U . . .
C052 C 0.5693(12) 0.3875(8) 0.7009(8) 0.055(5) Uani 1 1 d . . . . .
H052 H 0.619059 0.371593 0.703049 0.066 Uiso 1 1 calc R U . . .
C053 C 1.0471(9) 0.5313(8) -0.0504(9) 0.048(4) Uani 1 1 d . . . . .
H05F H 1.064570 0.554480 -0.009436 0.071 Uiso 1 1 calc R U . . .
H05G H 1.056702 0.552283 -0.094760 0.071 Uiso 1 1 calc R U . . .
H05H H 1.074697 0.494520 -0.050615 0.071 Uiso 1 1 calc R U . . .
C054 C 1.0567(10) 0.4660(8) 0.5800(9) 0.048(4) Uani 1 1 d . . . . .
H05I H 1.069397 0.445409 0.536136 0.072 Uiso 1 1 calc R U . . .
H05J H 1.067831 0.441299 0.621456 0.072 Uiso 1 1 calc R U . . .
H05N H 1.087142 0.501390 0.583776 0.072 Uiso 1 1 calc R U . . .
C055 C 0.9489(10) 0.4230(7) 0.7906(8) 0.042(4) Uani 1 1 d . . . . .
C056 C 1.0138(9) 0.4043(8) 0.3863(9) 0.047(4) Uani 1 1 d . . . . .
H056 H 1.064384 0.389909 0.388917 0.056 Uiso 1 1 calc R U . . .
C057 C 0.7506(11) 0.6421(8) 0.3256(10) 0.054(5) Uani 1 1 d . . . . .
H057 H 0.740846 0.681744 0.316130 0.065 Uiso 1 1 calc R U . . .
C058 C 1.1048(9) 0.3139(6) 0.1693(9) 0.042(4) Uani 1 1 d . . . . .
C059 C 1.0524(10) 0.4931(8) 0.7673(9) 0.048(4) Uani 1 1 d . . . . .
H059 H 1.105110 0.500275 0.761959 0.057 Uiso 1 1 calc R U . . .
C05A C 0.9144(9) 0.4378(6) 0.5897(8) 0.036(3) Uani 1 1 d . . . . .
C05B C 0.4909(10) 0.5005(9) 1.2676(10) 0.051(4) Uani 1 1 d . . . . .
H05B H 0.543662 0.491695 1.268914 0.061 Uiso 1 1 calc R U . . .
C05C C 0.2400(12) 0.5896(10) 0.6457(10) 0.064(6) Uani 1 1 d . . . . .
H05S H 0.190177 0.604824 0.639195 0.077 Uiso 1 1 calc R U . . .
C05D C 0.9264(12) 0.3670(8) 0.8094(9) 0.055(5) Uani 1 1 d . . . . .
H05D H 0.963170 0.338208 0.820469 0.066 Uiso 1 1 calc R U . . .
C05E C 0.2971(9) 0.4249(8) 1.2889(9) 0.044(4) Uani 1 1 d . . . . .
C05F C 1.0002(10) 0.5408(9) 0.7573(9) 0.050(4) Uani 1 1 d . . . . .
C05G C 0.5218(10) 0.5353(8) 1.0631(10) 0.052(4) Uani 1 1 d . . . . .
H05A H 0.550093 0.501161 1.079648 0.078 Uiso 1 1 calc R U . . .
H05C H 0.534670 0.568212 1.093956 0.078 Uiso 1 1 calc R U . . .
H05E H 0.535367 0.544136 1.013817 0.078 Uiso 1 1 calc R U . . .
C05H C 0.9354(10) 0.3732(7) 0.6064(9) 0.047(4) Uani 1 1 d . . . . .
H05O H 0.926653 0.365051 0.656885 0.070 Uiso 1 1 calc R U . . .
H05P H 0.989158 0.366589 0.596063 0.070 Uiso 1 1 calc R U . . .
H05R H 0.903625 0.347685 0.576493 0.070 Uiso 1 1 calc R U . . .
C05I C 0.5968(12) 0.7336(8) 0.0083(12) 0.072(7) Uani 1 1 d . . . . .
H05V H 0.561797 0.764106 -0.000797 0.086 Uiso 1 1 calc R U . . .
C05J C 0.6333(9) 0.3042(7) 0.9622(10) 0.045(4) Uani 1 1 d . . . . .
C05K C 0.8770(9) 0.3826(7) 0.3919(10) 0.046(4) Uani 1 1 d . . . . .
H05K H 0.836166 0.356347 0.397967 0.056 Uiso 1 1 calc R U . . .
C05L C 0.4543(11) 0.3930(7) 1.2929(10) 0.052(4) Uani 1 1 d . . . . .
H05L H 0.506069 0.381376 1.293837 0.062 Uiso 1 1 calc R U . . .
C05M C 0.3700(10) 0.3827(7) 0.8892(9) 0.045(4) Uani 1 1 d . . . . .
H05M H 0.411381 0.356623 0.895038 0.054 Uiso 1 1 calc R U . . .
C05N C 0.5051(12) 0.3534(8) 0.7128(10) 0.058(5) Uani 1 1 d . . . . .
H05T H 0.514446 0.314247 0.725066 0.070 Uiso 1 1 calc R U . . .
C05O C 0.4288(11) 0.3703(8) 0.7089(9) 0.054(4) Uani 1 1 d . . . . .
H05U H 0.388426 0.343979 0.716740 0.064 Uiso 1 1 calc R U . . .
C05P C 0.1325(10) 0.2941(6) 0.5265(9) 0.043(4) Uani 1 1 d . . . . .
C05Q C 0.3179(12) 0.3662(8) 1.3021(9) 0.055(5) Uani 1 1 d . . . . .
H05Q H 0.280236 0.337530 1.309165 0.065 Uiso 1 1 calc R U . . .
C1 C 1.0020(9) 0.4613(7) 0.3733(9) 0.043(4) Uani 1 1 d . . . . .
H1 H 1.044050 0.486521 0.368177 0.052 Uiso 1 1 calc R U . . .
C2 C 0.2313(11) 0.4073(10) 0.8882(10) 0.064(5) Uani 1 1 d . . . . .
H2 H 0.179757 0.395984 0.893060 0.077 Uiso 1 1 calc R U . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_atom_site_label_2
 _geom_bond_distance
 _geom_bond_site_symmetry_2
 _geom_bond_publ_flag
Cl01 C058 1.727(17) . ?
Cl02 C04R 1.718(16) . ?
Cl03 C034 1.723(17) . ?
Cl04 C04N 1.762(15) . ?
Cl05 C029 1.741(16) . ?
Cl06 C03W 1.787(15) . ?
Cl07 C04E 1.755(17) . ?
Cl08 C05P 1.722(16) . ?
Cl09 C02Y 1.713(17) . ?
Cl0A C01L 1.747(16) . ?
Cl0B C04P 1.744(17) . ?
Cl0C C04Z 1.783(15) . ?
Cl0D C02W 1.748(16) . ?
Cl0E C02O 1.701(16) . ?
Cl0F C02Z 1.758(17) . ?
Cl0G C05J 1.763(15) . ?
O00H C01X 1.328(18) . ?
O00H H00H 0.8200 . ?
O00I C048 1.35(2) . ?
O00I H00I 0.8200 . ?
O00J C01V 1.371(18) . ?
O00J H00J 0.8200 . ?
O00K C03Q 1.373(19) . ?
O00K H00K 0.8200 . ?
O00L C025 1.367(19) . ?
O00L H00L 0.8200 . ?
O00M C01A 1.354(17) . ?
O00M H00M 0.8200 . ?
O00N C01D 1.391(18) . ?
O00N H00N 0.8200 . ?
O00O C027 1.355(17) . ?
O00O H00O 0.8200 . ?
O00P C04A 1.365(19) . ?
O00P H00P 0.8200 . ?
N00Q C044 1.323(18) . ?
N00Q C02I 1.344(18) . ?
O00R C01Z 1.317(18) . ?
O00R H00R 0.8200 . ?
N00S C01S 1.326(18) . ?
N00S C02G 1.388(17) . ?
O00T C03Y 1.34(2) . ?
O00T H00T 0.8200 . ?
O00U C02M 1.326(18) . ?
O00U H00U 0.8200 . ?
N00V C01B 1.338(18) . ?
N00V C03K 1.364(19) . ?
N00W C031 1.33(2) . ?
N00W C01Y 1.36(2) . ?
O00X C02P 1.350(19) . ?
O00X H00X 0.8200 . ?
O00Y C01Q 1.397(18) . ?
O00Y H00Y 0.8200 . ?
N00Z C01I 1.34(2) . ?
N00Z C02E 1.366(19) . ?
N010 C022 1.325(19) . ?
N010 C02J 1.34(2) . ?
O011 C03V 1.375(19) . ?
O011 H011 0.8200 . ?
O012 C01N 1.380(18) . ?
O012 H012 0.8200 . ?
N013 C01C 1.313(19) . ?
N013 C04L 1.367(19) . ?
N014 C01H 1.349(18) . ?
N014 C02N 1.380(18) . ?
N015 C03G 1.35(2) . ?
N015 C05A 1.355(19) . ?
N016 C03D 1.31(2) . ?
N016 C02F 1.37(2) . ?
N017 C01G 1.330(18) . ?
N017 C02C 1.36(2) . ?
N018 C030 1.34(2) . ?
N018 C04K 1.38(2) . ?
N019 C028 1.340(19) . ?
N019 C03E 1.34(2) . ?
C01A C034 1.39(2) . ?
C01A C03T 1.42(2) . ?
C01B C01C 1.41(2) . ?
C01B C038 1.520(19) . ?
C01C C053 1.47(2) . ?
C01D C02L 1.38(2) . ?
C01D C02Z 1.40(2) . ?
C01E C04A 1.34(2) . ?
C01E C027 1.36(2) . ?
C01E H01E 0.9300 . ?
C01F C03W 1.32(2) . ?
C01F C034 1.39(2) . ?
C01F H01F 0.9300 . ?
C01G C02H 1.40(2) . ?
C01G C01J 1.47(2) . ?
C01H C02R 1.43(2) . ?
C01H C01I 1.432(18) . ?
C01I C020 1.43(2) . ?
C01J N01R 1.333(18) . ?
C01J C02D 1.44(2) . ?
N01K C026 1.30(2) . ?
N01K C04J 1.336(19) . ?
C01L C01N 1.35(2) . ?
C01L C03R 1.45(2) . ?
C01M C03V 1.36(2) . ?
C01M C03Y 1.37(2) . ?
C01M H01M 0.9300 . ?
C01N C02B 1.40(2) . ?
C01O C04N 1.35(2) . ?
C01O C04P 1.44(2) . ?
C01O H01O 0.9300 . ?
C01P C04H 1.32(2) . ?
C01P C02C 1.46(2) . ?
C01P H01P 0.9300 . ?
C01Q C04P 1.33(2) . ?
C01Q C02Q 1.42(2) . ?
N01R C045 1.344(19) . ?
C01S C030 1.40(2) . ?
C01S C03F 1.47(2) . ?
N01T C035 1.36(2) . ?
N01T C04C 1.37(2) . ?
C01U C02Z 1.37(2) . ?
C01U C02Y 1.39(2) . ?
C01U H01U 0.9300 . ?
C01V C03J 1.35(2) . ?
C01V C04R 1.43(2) . ?
C01W C04T 1.29(2) . ?
C01W C028 1.44(2) . ?
C01W H01W 0.9300 . ?
C01X C02L 1.35(2) . ?
C01X C02Y 1.43(2) . ?
C01Y C022 1.45(2) . ?
C01Y C02K 1.50(2) . ?
C01Z C04N 1.42(2) . ?
C01Z C02Q 1.42(2) . ?
C020 C057 1.35(3) . ?
C020 H020 0.9300 . ?
C021 C044 1.52(2) . ?
C021 H02B 0.9600 . ?
C021 H02C 0.9600 . ?
C021 H02D 0.9600 . ?
C022 C050 1.42(2) . ?
C023 C03M 1.39(2) . ?
C023 C04O 1.42(2) . ?
C023 C04D 1.50(2) . ?
C024 C03Q 1.38(2) . ?
C024 C025 1.39(2) . ?
C024 H024 0.9300 . ?
C025 C02O 1.39(2) . ?
C026 C02I 1.40(2) . ?
C026 C05G 1.51(2) . ?
C027 C058 1.43(2) . ?
C028 C035 1.41(2) . ?
C029 C05I 1.33(3) . ?
C029 C03Q 1.43(2) . ?
C02A C03H 1.31(2) . ?
C02A C04D 1.39(2) . ?
C02A H02A 0.9300 . ?
C02B C02M 1.41(2) . ?
C02B H02J 0.9300 . ?
C02C C045 1.45(2) . ?
C02D C03O 1.40(2) . ?
C02D H02H 0.9300 . ?
C02E C02N 1.435(19) . ?
C02E C1 1.44(2) . ?
C02F C03G 1.38(2) . ?
C02F C03C 1.47(2) . ?
C02G C04K 1.39(2) . ?
C02G C04V 1.50(2) . ?
C02H C03P 1.40(2) . ?
C02H H02I 0.9300 . ?
C02I C04G 1.53(2) . ?
C02J C031 1.42(2) . ?
C02J C05M 1.44(2) . ?
C02K C04I 1.35(3) . ?
C02K H02K 0.9300 . ?
C02L H02L 0.9300 . ?
C02M C05P 1.41(2) . ?
C02N C05K 1.45(2) . ?
C02O C05I 1.51(3) . ?
C02P C03W 1.35(2) . ?
C02P C03T 1.39(2) . ?
C02Q H02Q 0.9300 . ?
C02R C041 1.37(2) . ?
C02R H02R 0.9300 . ?
C02S C03I 1.39(2) . ?
C02S C02U 1.40(2) . ?
C02S C03U 1.42(2) . ?
C02T C03U 1.36(2) . ?
C02T C03X 1.40(2) . ?
C02T H02T 0.9300 . ?
C02U C03B 1.41(2) . ?
C02U C05F 1.47(2) . ?
C02V C03G 1.51(2) . ?
C02V H02E 0.9600 . ?
C02V H02F 0.9600 . ?
C02V H02G 0.9600 . ?
C02W C03N 1.37(2) . ?
C02W C048 1.38(2) . ?
C02X C05C 1.41(3) . ?
C02X C035 1.45(2) . ?
C02X H02X 0.9300 . ?
C030 C036 1.48(2) . ?
C031 C033 1.35(2) . ?
C032 C03I 1.36(3) . ?
C032 C043 1.40(2) . ?
C032 H032 0.9300 . ?
C033 C2 1.34(3) . ?
C033 H033 0.9300 . ?
C036 H03B 0.9600 . ?
C036 H03C 0.9600 . ?
C036 H03D 0.9600 . ?
C037 C03A 1.36(2) . ?
C037 C03M 1.45(2) . ?
C037 H037 0.9300 . ?
C038 H03M 0.9600 . ?
C038 H03N 0.9600 . ?
C038 H03O 0.9600 . ?
C039 C03K 1.46(2) . ?
C039 H03P 0.9600 . ?
C039 H03Q 0.9600 . ?
C039 H03R 0.9600 . ?
C03A C04F 1.38(3) . ?
C03A H03A 0.9300 . ?
C03B C03X 1.40(2) . ?
C03B C055 1.46(2) . ?
C03C H03T 0.9600 . ?
C03C H03V 0.9600 . ?
C03C H03W 0.9600 . ?
C03D C05A 1.40(2) . ?
C03D C054 1.55(2) . ?
C03E C040 1.43(2) . ?
C03E C04C 1.44(2) . ?
C03F H03E 0.9600 . ?
C03F H03F 0.9600 . ?
C03F H03G 0.9600 . ?
C03H C05E 1.45(2) . ?
C03H H03H 0.9300 . ?
C03I H03I 0.9300 . ?
C03J C048 1.41(2) . ?
C03J H03 0.9300 . ?
C03K C04L 1.38(2) . ?
C03L C04K 1.46(2) . ?
C03L H03J 0.9600 . ?
C03L H03K 0.9600 . ?
C03L H03L 0.9600 . ?
C03M C049 1.40(2) . ?
C03N C04R 1.37(2) . ?
C03N H0AA 0.9300 . ?
C03O C03P 1.44(3) . ?
C03O H03X 0.9300 . ?
C03P H03Y 0.9300 . ?
C03R C05P 1.35(2) . ?
C03R H2AA 0.9300 . ?
C03S C04I 1.36(3) . ?
C03S C050 1.45(2) . ?
C03S H03S 0.9300 . ?
C03T H1AA 0.9300 . ?
C03U H03U 0.9300 . ?
C03V C04E 1.42(2) . ?
C03X C04S 1.42(2) . ?
C03Y C05J 1.42(2) . ?
C03Z C05L 1.37(2) . ?
C03Z C05Q 1.41(3) . ?
C03Z H03Z 0.9300 . ?
C040 C052 1.42(2) . ?
C040 H040 0.9300 . ?
C041 C057 1.47(2) . ?
C041 H041 0.9300 . ?
C042 C04E 1.35(2) . ?
C042 C05J 1.39(2) . ?
C042 H042 0.9300 . ?
C043 C05F 1.38(2) . ?
C043 H043 0.9300 . ?
C044 C04J 1.36(2) . ?
C045 C04X 1.39(2) . ?
C046 C059 1.37(2) . ?
C046 C055 1.43(2) . ?
C046 H046 0.9300 . ?
C047 C04O 1.42(2) . ?
C047 C05L 1.43(2) . ?
C047 C05B 1.45(2) . ?
C049 C05B 1.29(3) . ?
C049 H049 0.9300 . ?
C04A C04Z 1.41(2) . ?
C04B C04S 1.40(2) . ?
C04B C05D 1.47(3) . ?
C04B H04B 0.9300 . ?
C04C C05O 1.38(2) . ?
C04D C04F 1.38(2) . ?
C04F H04F 0.9300 . ?
C04G H04A 0.9600 . ?
C04G H04C 0.9600 . ?
C04G H04D 0.9600 . ?
C04H C04W 1.478(18) . ?
C04H H04P 0.9300 . ?
C04I H04O 0.9300 . ?
C04J C04M 1.49(2) . ?
C04L C04U 1.52(2) . ?
C04M H04E 0.9600 . ?
C04M H04G 0.9600 . ?
C04M H04H 0.9600 . ?
C04O C05E 1.42(2) . ?
C04Q C05M 1.37(2) . ?
C04Q C2 1.50(3) . ?
C04Q H04Q 0.9300 . ?
C04S H04S 0.9300 . ?
C04T C05C 1.45(3) . ?
C04T H04T 0.9300 . ?
C04U H04L 0.9600 . ?
C04U H04M 0.9600 . ?
C04U H04N 0.9600 . ?
C04V H04I 0.9600 . ?
C04V H04J 0.9600 . ?
C04V H04K 0.9600 . ?
C04W C04X 1.34(2) . ?
C04W H04W 0.9300 . ?
C04X H04X 0.9300 . ?
C04Y C04Z 1.31(2) . ?
C04Y C058 1.41(2) . ?
C04Y H04Y 0.9300 . ?
C050 H050 0.9300 . ?
C051 C05K 1.31(2) . ?
C051 C056 1.47(2) . ?
C051 H051 0.9300 . ?
C052 C05N 1.37(3) . ?
C052 H052 0.9300 . ?
C053 H05F 0.9600 . ?
C053 H05G 0.9600 . ?
C053 H05H 0.9600 . ?
C054 H05I 0.9600 . ?
C054 H05J 0.9600 . ?
C054 H05N 0.9600 . ?
C055 C05D 1.37(2) . ?
C056 C1 1.33(2) . ?
C056 H056 0.9300 . ?
C057 H057 0.9300 . ?
C059 C05F 1.42(2) . ?
C059 H059 0.9300 . ?
C05A C05H 1.54(2) . ?
C05B H05B 0.9300 . ?
C05C H05S 0.9300 . ?
C05D H05D 0.9300 . ?
C05E C05Q 1.40(2) . ?
C05G H05A 0.9600 . ?
C05G H05C 0.9600 . ?
C05G H05E 0.9600 . ?
C05H H05O 0.9600 . ?
C05H H05P 0.9600 . ?
C05H H05R 0.9600 . ?
C05I H05V 0.9300 . ?
C05K H05K 0.9300 . ?
C05L H05L 0.9300 . ?
C05M H05M 0.9300 . ?
C05N C05O 1.37(3) . ?
C05N H05T 0.9300 . ?
C05O H05U 0.9300 . ?
C05Q H05Q 0.9300 . ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
 
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_atom_site_label_2
 _geom_angle_atom_site_label_3
 _geom_angle
 _geom_angle_site_symmetry_1
 _geom_angle_site_symmetry_3
 _geom_angle_publ_flag
C01X O00H H00H 109.5 . . ?
C048 O00I H00I 109.5 . . ?
C01V O00J H00J 109.5 . . ?
C03Q O00K H00K 109.5 . . ?
C025 O00L H00L 109.5 . . ?
C01A O00M H00M 109.5 . . ?
C01D O00N H00N 109.5 . . ?
C027 O00O H00O 109.5 . . ?
C04A O00P H00P 109.5 . . ?
C044 N00Q C02I 117.9(12) . . ?
C01Z O00R H00R 109.5 . . ?
C01S N00S C02G 118.9(12) . . ?
C03Y O00T H00T 109.5 . . ?
C02M O00U H00U 109.5 . . ?
C01B N00V C03K 118.7(12) . . ?
C031 N00W C01Y 117.9(13) . . ?
C02P O00X H00X 109.5 . . ?
C01Q O00Y H00Y 109.5 . . ?
C01I N00Z C02E 117.3(13) . . ?
C022 N010 C02J 116.4(13) . . ?
C03V O011 H011 109.5 . . ?
C01N O012 H012 109.5 . . ?
C01C N013 C04L 120.9(13) . . ?
C01H N014 C02N 114.8(12) . . ?
C03G N015 C05A 117.1(13) . . ?
C03D N016 C02F 120.4(13) . . ?
C01G N017 C02C 118.0(13) . . ?
C030 N018 C04K 120.4(13) . . ?
C028 N019 C03E 119.8(13) . . ?
O00M C01A C034 119.0(14) . . ?
O00M C01A C03T 122.7(12) . . ?
C034 C01A C03T 118.2(13) . . ?
N00V C01B C01C 121.5(12) . . ?
N00V C01B C038 116.4(13) . . ?
C01C C01B C038 122.2(13) . . ?
N013 C01C C01B 119.1(14) . . ?
N013 C01C C053 119.9(15) . . ?
C01B C01C C053 121.0(14) . . ?
C02L C01D O00N 123.9(12) . . ?
C02L C01D C02Z 118.4(14) . . ?
O00N C01D C02Z 117.7(13) . . ?
C04A C01E C027 123.7(14) . . ?
C04A C01E H01E 118.1 . . ?
C027 C01E H01E 118.1 . . ?
C03W C01F C034 121.5(15) . . ?
C03W C01F H01F 119.3 . . ?
C034 C01F H01F 119.3 . . ?
N017 C01G C02H 120.5(14) . . ?
N017 C01G C01J 119.5(13) . . ?
C02H C01G C01J 119.9(12) . . ?
N014 C01H C02R 116.5(13) . . ?
N014 C01H C01I 124.1(13) . . ?
C02R C01H C01I 119.4(13) . . ?
N00Z C01I C020 118.7(14) . . ?
N00Z C01I C01H 120.7(13) . . ?
C020 C01I C01H 120.7(15) . . ?
N01R C01J C02D 118.7(14) . . ?
N01R C01J C01G 121.8(13) . . ?
C02D C01J C01G 119.5(13) . . ?
C026 N01K C04J 119.6(13) . . ?
C01N C01L C03R 119.0(14) . . ?
C01N C01L Cl0A 120.8(13) . . ?
C03R C01L Cl0A 120.2(12) . . ?
C03V C01M C03Y 124.0(15) . . ?
C03V C01M H01M 118.0 . . ?
C03Y C01M H01M 118.0 . . ?
C01L C01N O012 119.7(13) . . ?
C01L C01N C02B 120.9(14) . . ?
O012 C01N C02B 119.4(12) . . ?
C04N C01O C04P 117.7(13) . . ?
C04N C01O H01O 121.2 . . ?
C04P C01O H01O 121.2 . . ?
C04H C01P C02C 117.5(14) . . ?
C04H C01P H01P 121.3 . . ?
C02C C01P H01P 121.3 . . ?
C04P C01Q O00Y 118.4(13) . . ?
C04P C01Q C02Q 121.8(14) . . ?
O00Y C01Q C02Q 119.6(12) . . ?
C01J N01R C045 119.3(13) . . ?
N00S C01S C030 119.3(13) . . ?
N00S C01S C03F 118.3(14) . . ?
C030 C01S C03F 122.3(14) . . ?
C035 N01T C04C 117.7(13) . . ?
C02Z C01U C02Y 120.7(13) . . ?
C02Z C01U H01U 119.6 . . ?
C02Y C01U H01U 119.6 . . ?
C03J C01V O00J 123.6(12) . . ?
C03J C01V C04R 119.8(14) . . ?
O00J C01V C04R 116.5(13) . . ?
C04T C01W C028 118.8(17) . . ?
C04T C01W H01W 120.6 . . ?
C028 C01W H01W 120.6 . . ?
O00H C01X C02L 124.2(14) . . ?
O00H C01X C02Y 116.2(14) . . ?
C02L C01X C02Y 119.6(14) . . ?
N00W C01Y C022 120.9(14) . . ?
N00W C01Y C02K 118.4(14) . . ?
C022 C01Y C02K 120.5(14) . . ?
O00R C01Z C04N 120.8(13) . . ?
O00R C01Z C02Q 121.1(14) . . ?
C04N C01Z C02Q 118.0(13) . . ?
C057 C020 C01I 120.8(16) . . ?
C057 C020 H020 119.6 . . ?
C01I C020 H020 119.6 . . ?
C044 C021 H02B 109.5 . . ?
C044 C021 H02C 109.5 . . ?
H02B C021 H02C 109.5 . . ?
C044 C021 H02D 109.5 . . ?
H02B C021 H02D 109.5 . . ?
H02C C021 H02D 109.5 . . ?
N010 C022 C050 119.8(14) . . ?
N010 C022 C01Y 120.7(13) . . ?
C050 C022 C01Y 119.2(15) . . ?
C03M C023 C04O 121.4(15) . . ?
C03M C023 C04D 120.8(14) . . ?
C04O C023 C04D 117.8(15) . . ?
C03Q C024 C025 121.9(13) . . ?
C03Q C024 H024 119.0 . . ?
C025 C024 H024 119.0 . . ?
O00L C025 C024 122.5(14) . . ?
O00L C025 C02O 116.6(14) . . ?
C024 C025 C02O 120.9(15) . . ?
N01K C026 C02I 119.9(14) . . ?
N01K C026 C05G 117.0(14) . . ?
C02I C026 C05G 123.0(15) . . ?
O00O C027 C01E 125.4(13) . . ?
O00O C027 C058 115.9(13) . . ?
C01E C027 C058 118.7(13) . . ?
N019 C028 C035 118.7(14) . . ?
N019 C028 C01W 121.5(14) . . ?
C035 C028 C01W 119.8(14) . . ?
C05I C029 C03Q 122.4(16) . . ?
C05I C029 Cl05 118.5(13) . . ?
C03Q C029 Cl05 119.0(12) . . ?
C03H C02A C04D 124.5(16) . . ?
C03H C02A H02A 117.7 . . ?
C04D C02A H02A 117.7 . . ?
C01N C02B C02M 120.5(13) . . ?
C01N C02B H02J 119.8 . . ?
C02M C02B H02J 119.8 . . ?
N017 C02C C045 122.5(13) . . ?
N017 C02C C01P 118.4(14) . . ?
C045 C02C C01P 119.1(13) . . ?
C03O C02D C01J 118.8(15) . . ?
C03O C02D H02H 120.6 . . ?
C01J C02D H02H 120.6 . . ?
N00Z C02E C02N 121.4(15) . . ?
N00Z C02E C1 119.8(13) . . ?
C02N C02E C1 118.7(14) . . ?
N016 C02F C03G 118.3(14) . . ?
N016 C02F C03C 117.8(14) . . ?
C03G C02F C03C 124.0(15) . . ?
C04K C02G N00S 122.8(13) . . ?
C04K C02G C04V 121.2(14) . . ?
N00S C02G C04V 116.0(13) . . ?
C03P C02H C01G 120.2(16) . . ?
C03P C02H H02I 119.9 . . ?
C01G C02H H02I 119.9 . . ?
N00Q C02I C026 120.4(14) . . ?
N00Q C02I C04G 116.6(13) . . ?
C026 C02I C04G 122.9(14) . . ?
N010 C02J C031 123.9(14) . . ?
N010 C02J C05M 116.0(13) . . ?
C031 C02J C05M 120.0(14) . . ?
C04I C02K C01Y 115.1(16) . . ?
C04I C02K H02K 122.4 . . ?
C01Y C02K H02K 122.4 . . ?
C01X C02L C01D 122.1(14) . . ?
C01X C02L H02L 118.9 . . ?
C01D C02L H02L 118.9 . . ?
O00U C02M C02B 123.0(13) . . ?
O00U C02M C05P 118.6(14) . . ?
C02B C02M C05P 118.4(13) . . ?
N014 C02N C02E 121.6(13) . . ?
N014 C02N C05K 119.5(13) . . ?
C02E C02N C05K 118.9(14) . . ?
C025 C02O C05I 117.2(14) . . ?
C025 C02O Cl0E 122.6(12) . . ?
C05I C02O Cl0E 120.2(12) . . ?
O00X C02P C03W 120.4(14) . . ?
O00X C02P C03T 120.5(14) . . ?
C03W C02P C03T 119.0(15) . . ?
C01Q C02Q C01Z 118.0(14) . . ?
C01Q C02Q H02Q 121.0 . . ?
C01Z C02Q H02Q 121.0 . . ?
C041 C02R C01H 117.5(15) . . ?
C041 C02R H02R 121.3 . . ?
C01H C02R H02R 121.3 . . ?
C03I C02S C02U 120.0(14) . . ?
C03I C02S C03U 122.3(16) . . ?
C02U C02S C03U 117.7(15) . . ?
C03U C02T C03X 124.1(16) . . ?
C03U C02T H02T 117.9 . . ?
C03X C02T H02T 117.9 . . ?
C02S C02U C03B 121.1(14) . . ?
C02S C02U C05F 118.2(15) . . ?
C03B C02U C05F 120.7(15) . . ?
C03G C02V H02E 109.5 . . ?
C03G C02V H02F 109.5 . . ?
H02E C02V H02F 109.5 . . ?
C03G C02V H02G 109.5 . . ?
H02E C02V H02G 109.5 . . ?
H02F C02V H02G 109.5 . . ?
C03N C02W C048 120.0(14) . . ?
C03N C02W Cl0D 120.1(11) . . ?
C048 C02W Cl0D 119.8(12) . . ?
C05C C02X C035 118.8(17) . . ?
C05C C02X H02X 120.6 . . ?
C035 C02X H02X 120.6 . . ?
C01U C02Y C01X 118.3(14) . . ?
C01U C02Y Cl09 121.4(11) . . ?
C01X C02Y Cl09 120.3(13) . . ?
C01U C02Z C01D 120.8(15) . . ?
C01U C02Z Cl0F 118.9(11) . . ?
C01D C02Z Cl0F 120.2(13) . . ?
N018 C030 C01S 121.7(14) . . ?
N018 C030 C036 116.8(14) . . ?
C01S C030 C036 121.5(15) . . ?
N00W C031 C033 121.7(15) . . ?
N00W C031 C02J 119.6(14) . . ?
C033 C031 C02J 118.7(15) . . ?
C03I C032 C043 119.7(17) . . ?
C03I C032 H032 120.1 . . ?
C043 C032 H032 120.1 . . ?
C2 C033 C031 124.4(17) . . ?
C2 C033 H033 117.8 . . ?
C031 C033 H033 117.8 . . ?
C01A C034 C01F 119.0(15) . . ?
C01A C034 Cl03 119.0(12) . . ?
C01F C034 Cl03 122.0(12) . . ?
N01T C035 C028 123.4(14) . . ?
N01T C035 C02X 116.3(15) . . ?
C028 C035 C02X 120.1(15) . . ?
C030 C036 H03B 109.5 . . ?
C030 C036 H03C 109.5 . . ?
H03B C036 H03C 109.5 . . ?
C030 C036 H03D 109.5 . . ?
H03B C036 H03D 109.5 . . ?
H03C C036 H03D 109.5 . . ?
C03A C037 C03M 121.1(15) . . ?
C03A C037 H037 119.5 . . ?
C03M C037 H037 119.5 . . ?
C01B C038 H03M 109.5 . . ?
C01B C038 H03N 109.5 . . ?
H03M C038 H03N 109.5 . . ?
C01B C038 H03O 109.5 . . ?
H03M C038 H03O 109.5 . . ?
H03N C038 H03O 109.5 . . ?
C03K C039 H03P 109.5 . . ?
C03K C039 H03Q 109.5 . . ?
H03P C039 H03Q 109.5 . . ?
C03K C039 H03R 109.5 . . ?
H03P C039 H03R 109.5 . . ?
H03Q C039 H03R 109.5 . . ?
C037 C03A C04F 120.4(16) . . ?
C037 C03A H03A 119.8 . . ?
C04F C03A H03A 119.8 . . ?
C03X C03B C02U 120.8(15) . . ?
C03X C03B C055 119.3(15) . . ?
C02U C03B C055 119.8(14) . . ?
C02F C03C H03T 109.5 . . ?
C02F C03C H03V 109.5 . . ?
H03T C03C H03V 109.5 . . ?
C02F C03C H03W 109.5 . . ?
H03T C03C H03W 109.5 . . ?
H03V C03C H03W 109.5 . . ?
N016 C03D C05A 120.8(14) . . ?
N016 C03D C054 120.0(14) . . ?
C05A C03D C054 119.2(15) . . ?
N019 C03E C040 118.0(14) . . ?
N019 C03E C04C 122.2(13) . . ?
C040 C03E C04C 119.8(14) . . ?
C01S C03F H03E 109.5 . . ?
C01S C03F H03F 109.5 . . ?
H03E C03F H03F 109.5 . . ?
C01S C03F H03G 109.5 . . ?
H03E C03F H03G 109.5 . . ?
H03F C03F H03G 109.5 . . ?
N015 C03G C02F 122.7(14) . . ?
N015 C03G C02V 117.2(15) . . ?
C02F C03G C02V 119.9(15) . . ?
C02A C03H C05E 121.2(17) . . ?
C02A C03H H03H 119.4 . . ?
C05E C03H H03H 119.4 . . ?
C032 C03I C02S 122.1(16) . . ?
C032 C03I H03I 118.9 . . ?
C02S C03I H03I 118.9 . . ?
C01V C03J C048 122.2(14) . . ?
C01V C03J H03 118.9 . . ?
C048 C03J H03 118.9 . . ?
N00V C03K C04L 120.1(14) . . ?
N00V C03K C039 118.5(13) . . ?
C04L C03K C039 121.4(15) . . ?
C04K C03L H03J 109.5 . . ?
C04K C03L H03K 109.5 . . ?
H03J C03L H03K 109.5 . . ?
C04K C03L H03L 109.5 . . ?
H03J C03L H03L 109.5 . . ?
H03K C03L H03L 109.5 . . ?
C023 C03M C049 118.6(16) . . ?
C023 C03M C037 117.9(15) . . ?
C049 C03M C037 123.5(16) . . ?
C04R C03N C02W 123.2(14) . . ?
C04R C03N H0AA 118.4 . . ?
C02W C03N H0AA 118.4 . . ?
C02D C03O C03P 121.0(16) . . ?
C02D C03O H03X 119.5 . . ?
C03P C03O H03X 119.5 . . ?
C02H C03P C03O 120.5(17) . . ?
C02H C03P H03Y 119.7 . . ?
C03O C03P H03Y 119.7 . . ?
O00K C03Q C024 123.0(14) . . ?
O00K C03Q C029 118.6(15) . . ?
C024 C03Q C029 118.3(14) . . ?
C05P C03R C01L 120.5(14) . . ?
C05P C03R H2AA 119.7 . . ?
C01L C03R H2AA 119.7 . . ?
C04I C03S C050 120.4(17) . . ?
C04I C03S H03S 119.8 . . ?
C050 C03S H03S 119.8 . . ?
C02P C03T C01A 119.8(14) . . ?
C02P C03T H1AA 120.1 . . ?
C01A C03T H1AA 120.1 . . ?
C02T C03U C02S 119.7(15) . . ?
C02T C03U H03U 120.2 . . ?
C02S C03U H03U 120.2 . . ?
C01M C03V O011 124.1(14) . . ?
C01M C03V C04E 117.4(15) . . ?
O011 C03V C04E 118.5(13) . . ?
C01F C03W C02P 122.2(15) . . ?
C01F C03W Cl06 119.9(12) . . ?
C02P C03W Cl06 117.9(12) . . ?
C03B C03X C02T 116.6(15) . . ?
C03B C03X C04S 119.6(15) . . ?
C02T C03X C04S 123.7(16) . . ?
O00T C03Y C01M 125.0(15) . . ?
O00T C03Y C05J 118.9(14) . . ?
C01M C03Y C05J 115.9(16) . . ?
C05L C03Z C05Q 122.1(16) . . ?
C05L C03Z H03Z 118.9 . . ?
C05Q C03Z H03Z 118.9 . . ?
C052 C040 C03E 118.1(16) . . ?
C052 C040 H040 120.9 . . ?
C03E C040 H040 120.9 . . ?
C02R C041 C057 124.0(15) . . ?
C02R C041 H041 118.0 . . ?
C057 C041 H041 118.0 . . ?
C04E C042 C05J 117.1(15) . . ?
C04E C042 H042 121.4 . . ?
C05J C042 H042 121.4 . . ?
C05F C043 C032 121.5(17) . . ?
C05F C043 H043 119.2 . . ?
C032 C043 H043 119.2 . . ?
N00Q C044 C04J 121.5(13) . . ?
N00Q C044 C021 115.5(13) . . ?
C04J C044 C021 123.0(14) . . ?
N01R C045 C04X 122.1(15) . . ?
N01R C045 C02C 118.8(13) . . ?
C04X C045 C02C 119.1(14) . . ?
C059 C046 C055 120.3(16) . . ?
C059 C046 H046 119.8 . . ?
C055 C046 H046 119.8 . . ?
C04O C047 C05L 116.6(15) . . ?
C04O C047 C05B 117.9(14) . . ?
C05L C047 C05B 125.5(16) . . ?
O00I C048 C02W 119.4(15) . . ?
O00I C048 C03J 123.0(15) . . ?
C02W C048 C03J 117.5(15) . . ?
C05B C049 C03M 122.5(18) . . ?
C05B C049 H049 118.8 . . ?
C03M C049 H049 118.8 . . ?
C01E C04A O00P 124.6(14) . . ?
C01E C04A C04Z 116.9(15) . . ?
O00P C04A C04Z 118.5(14) . . ?
C04S C04B C05D 119.6(16) . . ?
C04S C04B H04B 120.2 . . ?
C05D C04B H04B 120.2 . . ?
N01T C04C C05O 120.7(15) . . ?
N01T C04C C03E 118.1(13) . . ?
C05O C04C C03E 121.2(15) . . ?
C04F C04D C02A 127.0(17) . . ?
C04F C04D C023 115.7(16) . . ?
C02A C04D C023 117.2(15) . . ?
C042 C04E C03V 122.6(15) . . ?
C042 C04E Cl07 119.0(13) . . ?
C03V C04E Cl07 118.3(13) . . ?
C03A C04F C04D 124.0(18) . . ?
C03A C04F H04F 118.0 . . ?
C04D C04F H04F 118.0 . . ?
C02I C04G H04A 109.5 . . ?
C02I C04G H04C 109.5 . . ?
H04A C04G H04C 109.5 . . ?
C02I C04G H04D 109.5 . . ?
H04A C04G H04D 109.5 . . ?
H04C C04G H04D 109.5 . . ?
C01P C04H C04W 124.0(15) . . ?
C01P C04H H04P 118.0 . . ?
C04W C04H H04P 118.0 . . ?
C02K C04I C03S 126(2) . . ?
C02K C04I H04O 116.8 . . ?
C03S C04I H04O 116.8 . . ?
N01K C04J C044 120.6(13) . . ?
N01K C04J C04M 117.1(14) . . ?
C044 C04J C04M 122.2(14) . . ?
N018 C04K C02G 116.8(14) . . ?
N018 C04K C03L 121.0(14) . . ?
C02G C04K C03L 122.2(15) . . ?
N013 C04L C03K 119.8(14) . . ?
N013 C04L C04U 119.7(14) . . ?
C03K C04L C04U 120.6(15) . . ?
C04J C04M H04E 109.5 . . ?
C04J C04M H04G 109.5 . . ?
H04E C04M H04G 109.5 . . ?
C04J C04M H04H 109.5 . . ?
H04E C04M H04H 109.5 . . ?
H04G C04M H04H 109.5 . . ?
C01O C04N C01Z 122.9(13) . . ?
C01O C04N Cl04 119.6(11) . . ?
C01Z C04N Cl04 117.5(11) . . ?
C023 C04O C05E 121.0(16) . . ?
C023 C04O C047 117.8(14) . . ?
C05E C04O C047 121.2(15) . . ?
C01Q C04P C01O 121.3(15) . . ?
C01Q C04P Cl0B 121.6(12) . . ?
C01O C04P Cl0B 116.7(12) . . ?
C05M C04Q C2 117.2(17) . . ?
C05M C04Q H04Q 121.4 . . ?
C2 C04Q H04Q 121.4 . . ?
C03N C04R C01V 117.1(14) . . ?
C03N C04R Cl02 122.5(12) . . ?
C01V C04R Cl02 120.5(13) . . ?
C04B C04S C03X 121.4(17) . . ?
C04B C04S H04S 119.3 . . ?
C03X C04S H04S 119.3 . . ?
C01W C04T C05C 125.8(19) . . ?
C01W C04T H04T 117.1 . . ?
C05C C04T H04T 117.1 . . ?
C04L C04U H04L 109.5 . . ?
C04L C04U H04M 109.5 . . ?
H04L C04U H04M 109.5 . . ?
C04L C04U H04N 109.5 . . ?
H04L C04U H04N 109.5 . . ?
H04M C04U H04N 109.5 . . ?
C02G C04V H04I 109.5 . . ?
C02G C04V H04J 109.5 . . ?
H04I C04V H04J 109.5 . . ?
C02G C04V H04K 109.5 . . ?
H04I C04V H04K 109.5 . . ?
H04J C04V H04K 109.5 . . ?
C04X C04W C04H 117.5(14) . . ?
C04X C04W H04W 121.2 . . ?
C04H C04W H04W 121.2 . . ?
C04W C04X C045 122.6(15) . . ?
C04W C04X H04X 118.7 . . ?
C045 C04X H04X 118.7 . . ?
C04Z C04Y C058 120.7(15) . . ?
C04Z C04Y H04Y 119.6 . . ?
C058 C04Y H04Y 119.6 . . ?
C04Y C04Z C04A 122.6(15) . . ?
C04Y C04Z Cl0C 118.8(12) . . ?
C04A C04Z Cl0C 118.5(13) . . ?
C022 C050 C03S 118.2(15) . . ?
C022 C050 H050 120.9 . . ?
C03S C050 H050 120.9 . . ?
C05K C051 C056 120.2(17) . . ?
C05K C051 H051 119.9 . . ?
C056 C051 H051 119.9 . . ?
C05N C052 C040 117.4(18) . . ?
C05N C052 H052 121.3 . . ?
C040 C052 H052 121.3 . . ?
C01C C053 H05F 109.5 . . ?
C01C C053 H05G 109.5 . . ?
H05F C053 H05G 109.5 . . ?
C01C C053 H05H 109.5 . . ?
H05F C053 H05H 109.5 . . ?
H05G C053 H05H 109.5 . . ?
C03D C054 H05I 109.5 . . ?
C03D C054 H05J 109.5 . . ?
H05I C054 H05J 109.5 . . ?
C03D C054 H05N 109.5 . . ?
H05I C054 H05N 109.5 . . ?
H05J C054 H05N 109.5 . . ?
C05D C055 C046 120.3(16) . . ?
C05D C055 C03B 121.2(16) . . ?
C046 C055 C03B 118.4(15) . . ?
C1 C056 C051 121.4(16) . . ?
C1 C056 H056 119.3 . . ?
C051 C056 H056 119.3 . . ?
C020 C057 C041 117.6(16) . . ?
C020 C057 H057 121.2 . . ?
C041 C057 H057 121.2 . . ?
C04Y C058 C027 117.2(15) . . ?
C04Y C058 Cl01 122.6(12) . . ?
C027 C058 Cl01 120.2(12) . . ?
C046 C059 C05F 123.9(16) . . ?
C046 C059 H059 118.1 . . ?
C05F C059 H059 118.1 . . ?
N015 C05A C03D 120.6(14) . . ?
N015 C05A C05H 115.5(13) . . ?
C03D C05A C05H 123.8(14) . . ?
C049 C05B C047 121.8(17) . . ?
C049 C05B H05B 119.1 . . ?
C047 C05B H05B 119.1 . . ?
C02X C05C C04T 116.6(18) . . ?
C02X C05C H05S 121.7 . . ?
C04T C05C H05S 121.7 . . ?
C055 C05D C04B 118.6(17) . . ?
C055 C05D H05D 120.7 . . ?
C04B C05D H05D 120.7 . . ?
C05Q C05E C04O 120.5(16) . . ?
C05Q C05E C03H 121.2(16) . . ?
C04O C05E C03H 118.2(16) . . ?
C043 C05F C059 124.8(16) . . ?
C043 C05F C02U 118.3(16) . . ?
C059 C05F C02U 116.8(17) . . ?
C026 C05G H05A 109.5 . . ?
C026 C05G H05C 109.5 . . ?
H05A C05G H05C 109.5 . . ?
C026 C05G H05E 109.5 . . ?
H05A C05G H05E 109.5 . . ?
H05C C05G H05E 109.5 . . ?
C05A C05H H05O 109.5 . . ?
C05A C05H H05P 109.5 . . ?
H05O C05H H05P 109.5 . . ?
C05A C05H H05R 109.5 . . ?
H05O C05H H05R 109.5 . . ?
H05P C05H H05R 109.5 . . ?
C029 C05I C02O 119.1(15) . . ?
C029 C05I H05V 120.4 . . ?
C02O C05I H05V 120.4 . . ?
C042 C05J C03Y 122.8(14) . . ?
C042 C05J Cl0G 118.7(12) . . ?
C03Y C05J Cl0G 118.4(14) . . ?
C051 C05K C02N 120.9(16) . . ?
C051 C05K H05K 119.6 . . ?
C02N C05K H05K 119.6 . . ?
C03Z C05L C047 121.4(16) . . ?
C03Z C05L H05L 119.3 . . ?
C047 C05L H05L 119.3 . . ?
C04Q C05M C02J 120.5(16) . . ?
C04Q C05M H05M 119.7 . . ?
C02J C05M H05M 119.7 . . ?
C05O C05N C052 127.6(18) . . ?
C05O C05N H05T 116.2 . . ?
C052 C05N H05T 116.2 . . ?
C05N C05O C04C 115.8(17) . . ?
C05N C05O H05U 122.1 . . ?
C04C C05O H05U 122.1 . . ?
C03R C05P C02M 120.6(15) . . ?
C03R C05P Cl08 119.8(12) . . ?
C02M C05P Cl08 119.4(12) . . ?
C05E C05Q C03Z 118.1(17) . . ?
C05E C05Q H05Q 120.9 . . ?
C03Z C05Q H05Q 120.9 . . ?
C056 C1 C02E 119.9(15) . . ?
C056 C1 H1 120.1 . . ?
C02E C1 H1 120.1 . . ?
C033 C2 C04Q 119.1(17) . . ?
C033 C2 H2 120.4 . . ?
C04Q C2 H2 120.4 . . ?
 
_refine_diff_density_max    0.701
_refine_diff_density_min   -0.658
_refine_diff_density_rms    0.123





















































































