data_global
#==============================================================================

# PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic      2019-04-16
_journal_date_to_coeditor         ?
_journal_date_from_coeditor       ?
_journal_date_accepted     2019-09-05
_journal_date_printers_first      ?
_journal_date_printers_final      ?
_journal_date_proofs_out          ?
_journal_date_proofs_in           ?
_journal_coeditor_name            ?
_journal_coeditor_code      LQ5023
_journal_coeditor_notes
; ?
;
_journal_paper_category      FA
_journal_techeditor_code      M191236
_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-97 
data_MC_PP 
_database_code_depnum_ccdc_archive 'CCDC 1906693'
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H26 N2 O2' 
_chemical_formula_weight          302.41 
  
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' 
  
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    Pbca 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
 '-x, -y, -z' 
 'x-1/2, y, -z-1/2' 
 'x, -y-1/2, z-1/2' 
 '-x-1/2, y-1/2, z' 
  
_cell_length_a                    5.5482(17) 
_cell_length_b                    12.167(3) 
_cell_length_c                    24.556(6) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1657.6(8) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     113(2) 
_cell_measurement_reflns_used           3581 
_cell_measurement_theta_min             3.3 
_cell_measurement_theta_max             27.5 
  
_exptl_crystal_description        Prism 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.212 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              656 
_exptl_absorpt_coefficient_mu     0.079 
_exptl_absorpt_correction_type    MULTI-SCAN 
_exptl_absorpt_correction_T_min   0.9844 
_exptl_absorpt_correction_T_max   0.9906 
_exptl_absorpt_process_details    'REQAB (Rigaku, 1998)' 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       113(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   multilayer 
_diffrn_measurement_device_type   'Rigaku XtaLAB P200' 
_diffrn_measurement_method        'ω and φ scans' 
_diffrn_detector_area_resol_mean  5.814 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             14815 
_diffrn_reflns_av_R_equivalents   0.0534 
_diffrn_reflns_av_sigmaI/netI     0.0272 
_diffrn_reflns_limit_h_min        -6 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        15 
_diffrn_reflns_limit_l_min        -31 
_diffrn_reflns_limit_l_max        31 
_diffrn_reflns_theta_min          3.32 
_diffrn_reflns_theta_max          27.55 
_reflns_number_total              1882 
_reflns_number_gt                 1509 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection   'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)' 
_computing_cell_refinement    'CrystalClear-SM Expert 2.1 b42' 
_computing_data_reduction     'CrystalClear-SM Expert 2.1 b42' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'CrystalStructure 4.1' 
_computing_publication_material   'CrystalStructure 4.1 (Rigaku, 2014)' 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0602P)²+0.6510P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          1882 
_refine_ls_number_parameters      105 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0563 
_refine_ls_R_factor_gt            0.0441 
_refine_ls_wR_factor_ref          0.1238 
_refine_ls_wR_factor_gt           0.1171 
_refine_ls_goodness_of_fit_ref    1.055 
_refine_ls_restrained_S_all       1.055 
_refine_ls_shift/su_max           0.002 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O -0.01637(18) 0.31953(9) 0.08127(4) 0.0275(3) Uani 1 1 d . . . 
H1D H -0.1137 0.3703 0.0740 0.041 Uiso 1 1 calc R . . 
N1 N 0.1342(2) 0.04624(10) 0.95399(5) 0.0234(3) Uani 1 1 d D . . 
H1 H 0.023(2) 0.0457(15) 0.9276(6) 0.028 Uiso 1 1 d D . . 
C1 C 0.6841(3) 0.23141(14) 0.19250(6) 0.0315(4) Uani 1 1 d . . . 
H1A H 0.6041 0.1740 0.2139 0.047 Uiso 1 1 calc R . . 
H1B H 0.8039 0.2689 0.2152 0.047 Uiso 1 1 calc R . . 
H1C H 0.7644 0.1980 0.1610 0.047 Uiso 1 1 calc R . . 
C2 C 0.4993(2) 0.31344(13) 0.17303(6) 0.0251(3) Uani 1 1 d . . . 
C3 C 0.3239(2) 0.28236(12) 0.13540(6) 0.0242(3) Uani 1 1 d . . . 
H3 H 0.3251 0.2097 0.1213 0.029 Uiso 1 1 calc R . . 
C4 C 0.1468(2) 0.35574(12) 0.11808(5) 0.0226(3) Uani 1 1 d . . . 
C5 C 0.1451(3) 0.46315(12) 0.13857(6) 0.0251(3) Uani 1 1 d . . . 
H5 H 0.0245 0.5138 0.1274 0.030 Uiso 1 1 calc R . . 
C6 C 0.3220(3) 0.49470(13) 0.17540(6) 0.0277(3) Uani 1 1 d . . . 
H6 H 0.3226 0.5677 0.1891 0.033 Uiso 1 1 calc R . . 
C7 C 0.4980(3) 0.42116(14) 0.19255(6) 0.0280(3) Uani 1 1 d . . . 
H7 H 0.6180 0.4443 0.2177 0.034 Uiso 1 1 calc R . . 
C8 C 0.0479(3) 0.11574(12) 0.99920(6) 0.0274(3) Uani 1 1 d . . . 
H8A H 0.0065 0.1894 0.9848 0.033 Uiso 1 1 calc R . . 
H8B H 0.1797 0.1250 1.0260 0.033 Uiso 1 1 calc R . . 
C9 C 0.1718(3) -0.06783(12) 0.97202(6) 0.0263(3) Uani 1 1 d . . . 
H9A H 0.3114 -0.0703 0.9971 0.032 Uiso 1 1 calc R . . 
H9B H 0.2108 -0.1139 0.9400 0.032 Uiso 1 1 calc R . . 
  
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.0214(5) 0.0276(5) 0.0334(5) -0.0014(4) -0.0066(4) 0.0017(4) 
N1 0.0177(6) 0.0287(6) 0.0239(6) 0.0008(5) 0.0003(5) -0.0005(5) 
C1 0.0221(8) 0.0388(9) 0.0335(7) 0.0061(6) -0.0037(6) 0.0019(6) 
C2 0.0173(7) 0.0333(8) 0.0248(6) 0.0058(6) 0.0016(5) -0.0010(6) 
C3 0.0190(7) 0.0264(7) 0.0272(7) 0.0018(5) 0.0017(5) -0.0009(5) 
C4 0.0163(7) 0.0272(7) 0.0242(7) 0.0025(5) 0.0014(5) -0.0026(5) 
C5 0.0196(7) 0.0278(7) 0.0280(7) 0.0021(5) 0.0009(5) 0.0026(6) 
C6 0.0262(8) 0.0289(8) 0.0281(7) -0.0021(6) 0.0012(6) -0.0021(6) 
C7 0.0208(8) 0.0375(8) 0.0257(7) 0.0002(6) -0.0029(5) -0.0037(6) 
C8 0.0247(8) 0.0261(7) 0.0314(7) -0.0011(6) 0.0043(6) -0.0029(6) 
C9 0.0217(7) 0.0282(8) 0.0290(7) -0.0002(6) 0.0043(6) 0.0017(6) 
  
_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 C4 1.3529(17) . ? 
O1 H1D 0.8400 . ? 
N1 C9 1.4716(19) . ? 
N1 C8 1.4752(19) . ? 
N1 H1 0.894(9) . ? 
C1 C2 1.508(2) . ? 
C1 H1A 0.9800 . ? 
C1 H1B 0.9800 . ? 
C1 H1C 0.9800 . ? 
C2 C3 1.394(2) . ? 
C2 C7 1.395(2) . ? 
C3 C4 1.394(2) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.400(2) . ? 
C5 C6 1.389(2) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.390(2) . ? 
C6 H6 0.9500 . ? 
C7 H7 0.9500 . ? 
C8 C9 1.525(2) 5_557 ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 C8 1.525(2) 5_557 ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
  
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 
C4 O1 H1D 109.5 . . ? 
C9 N1 C8 111.11(11) . . ? 
C9 N1 H1 108.0(12) . . ? 
C8 N1 H1 109.1(11) . . ? 
C2 C1 H1A 109.5 . . ? 
C2 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
C2 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
C3 C2 C7 118.60(13) . . ? 
C3 C2 C1 120.33(14) . . ? 
C7 C2 C1 121.07(13) . . ? 
C4 C3 C2 121.37(14) . . ? 
C4 C3 H3 119.3 . . ? 
C2 C3 H3 119.3 . . ? 
O1 C4 C3 117.83(13) . . ? 
O1 C4 C5 122.66(12) . . ? 
C3 C4 C5 119.51(13) . . ? 
C6 C5 C4 119.17(13) . . ? 
C6 C5 H5 120.4 . . ? 
C4 C5 H5 120.4 . . ? 
C5 C6 C7 121.07(14) . . ? 
C5 C6 H6 119.5 . . ? 
C7 C6 H6 119.5 . . ? 
C6 C7 C2 120.27(14) . . ? 
C6 C7 H7 119.9 . . ? 
C2 C7 H7 119.9 . . ? 
N1 C8 C9 112.89(12) . 5_557 ? 
N1 C8 H8A 109.0 . . ? 
C9 C8 H8A 109.0 5_557 . ? 
N1 C8 H8B 109.0 . . ? 
C9 C8 H8B 109.0 5_557 . ? 
H8A C8 H8B 107.8 . . ? 
N1 C9 C8 112.74(12) . 5_557 ? 
N1 C9 H9A 109.0 . . ? 
C8 C9 H9A 109.0 5_557 . ? 
N1 C9 H9B 109.0 . . ? 
C8 C9 H9B 109.0 5_557 . ? 
H9A C9 H9B 107.8 . . ? 
  
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 
C7 C2 C3 C4 -1.3(2) . . . . ? 
C1 C2 C3 C4 178.00(13) . . . . ? 
C2 C3 C4 O1 179.67(12) . . . . ? 
C2 C3 C4 C5 0.3(2) . . . . ? 
O1 C4 C5 C6 -178.64(13) . . . . ? 
C3 C4 C5 C6 0.7(2) . . . . ? 
C4 C5 C6 C7 -0.7(2) . . . . ? 
C5 C6 C7 C2 -0.2(2) . . . . ? 
C3 C2 C7 C6 1.2(2) . . . . ? 
C1 C2 C7 C6 -178.04(13) . . . . ? 
C9 N1 C8 C9 -52.21(17) . . . 5_557 ? 
C8 N1 C9 C8 52.13(17) . . . 5_557 ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O1 H1D N1  0.84 1.86 2.6789(16) 164.6 4_456 
  
_diffrn_measured_fraction_theta_max    0.984 
_diffrn_reflns_theta_full              27.55 
_diffrn_measured_fraction_theta_full   0.984 
_refine_diff_density_max    0.271 
_refine_diff_density_min   -0.193 
_refine_diff_density_rms    0.043 
 
data_OC_PP
_database_code_depnum_ccdc_archive 'CCDC 1907006'
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C18 H26 N2 O2' 
_chemical_formula_weight          302.41 
  
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' 
  
_symmetry_cell_setting            Monoclinic 
_symmetry_space_group_name_H-M    P2(1)/n 
  
loop_ 
 _symmetry_equiv_pos_as_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                    5.6352(8) 
_cell_length_b                    13.4281(17) 
_cell_length_c                    11.2825(15) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  93.703(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      852.0(2) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     133(2) 
_cell_measurement_reflns_used           2692 
_cell_measurement_theta_min             3.0 
_cell_measurement_theta_max             27.5 
  
_exptl_crystal_description        Prism 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.179 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              328 
_exptl_absorpt_coefficient_mu     0.077 
_exptl_absorpt_correction_type    MULTI-SCAN 
_exptl_absorpt_correction_T_min   0.9848 
_exptl_absorpt_correction_T_max   0.9908 
_exptl_absorpt_process_details    'REQAB (Rigaku, 1998)' 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       133(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   multilayer 
_diffrn_measurement_device_type   'Rigaku XtaLAB P200' 
_diffrn_measurement_method        'ω and φ scans' 
_diffrn_detector_area_resol_mean  5.814 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             8549 
_diffrn_reflns_av_R_equivalents   0.0384 
_diffrn_reflns_av_sigmaI/netI     0.0221 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -17 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -14 
_diffrn_reflns_limit_l_max        14 
_diffrn_reflns_theta_min          3.03 
_diffrn_reflns_theta_max          27.56 
_reflns_number_total              1950 
_reflns_number_gt                 1756 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection   'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)' 
_computing_cell_refinement    'CrystalClear-SM Expert 2.1 b42' 
_computing_data_reduction     'CrystalClear-SM Expert 2.1 b42' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'CrystalStructure 4.1' 
_computing_publication_material   'CrystalStructure 4.1 (Rigaku, 2014)' 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0688P)²+0.1842P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.085(10) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          1950 
_refine_ls_number_parameters      106 
_refine_ls_number_restraints      1 
_refine_ls_R_factor_all           0.0445 
_refine_ls_R_factor_gt            0.0412 
_refine_ls_wR_factor_ref          0.1260 
_refine_ls_wR_factor_gt           0.1226 
_refine_ls_goodness_of_fit_ref    1.065 
_refine_ls_restrained_S_all       1.066 
_refine_ls_shift/su_max           0.003 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 1.05690(15) 0.57651(6) 0.75902(8) 0.0372(3) Uani 1 1 d . . . 
H1A H 1.1454 0.5742 0.7020 0.056 Uiso 1 1 calc R . . 
C1 C 0.89645(18) 0.65072(8) 0.74061(10) 0.0285(3) Uani 1 1 d . . . 
C2 C 0.9026(2) 0.71750(8) 0.64681(11) 0.0336(3) Uani 1 1 d . . . 
H2 H 1.0266 0.7132 0.5939 0.040 Uiso 1 1 calc R . . 
C3 C 0.7294(2) 0.79034(9) 0.62972(11) 0.0369(3) Uani 1 1 d . . . 
H3 H 0.7347 0.8352 0.5649 0.044 Uiso 1 1 calc R . . 
C4 C 0.5483(2) 0.79791(9) 0.70711(11) 0.0368(3) Uani 1 1 d . . . 
H4 H 0.4299 0.8480 0.6962 0.044 Uiso 1 1 calc R . . 
C5 C 0.5435(2) 0.73109(9) 0.80048(10) 0.0334(3) Uani 1 1 d . . . 
H5 H 0.4192 0.7360 0.8532 0.040 Uiso 1 1 calc R . . 
C6 C 0.71360(19) 0.65741(8) 0.81964(9) 0.0296(3) Uani 1 1 d . . . 
C7 C 0.7031(3) 0.58354(10) 0.91929(11) 0.0431(3) Uani 1 1 d . . . 
H7A H 0.5596 0.5954 0.9619 0.065 Uiso 1 1 calc R . . 
H7B H 0.8440 0.5912 0.9741 0.065 Uiso 1 1 calc R . . 
H7C H 0.6987 0.5158 0.8868 0.065 Uiso 1 1 calc R . . 
N1 N 0.38092(16) 0.55195(7) 0.59346(8) 0.0297(2) Uani 1 1 d D . . 
H1 H 0.495(2) 0.5917(9) 0.6211(12) 0.036 Uiso 1 1 d D . . 
C8 C 0.4569(3) 0.44838(10) 0.60656(11) 0.0423(3) Uani 1 1 d . . . 
H8A H 0.3215 0.4042 0.5825 0.051 Uiso 1 1 calc R . . 
H8B H 0.5031 0.4351 0.6912 0.051 Uiso 1 1 calc R . . 
C9 C 0.3347(2) 0.57641(10) 0.46770(11) 0.0430(3) Uani 1 1 d . . . 
H9A H 0.2989 0.6484 0.4601 0.052 Uiso 1 1 calc R . . 
H9B H 0.1927 0.5392 0.4361 0.052 Uiso 1 1 calc R . . 
  
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.0336(5) 0.0373(5) 0.0417(5) 0.0029(3) 0.0105(3) 0.0073(3) 
C1 0.0254(5) 0.0279(5) 0.0324(5) -0.0066(4) 0.0038(4) -0.0024(4) 
C2 0.0309(6) 0.0322(6) 0.0390(6) -0.0019(4) 0.0121(4) -0.0022(4) 
C3 0.0402(6) 0.0315(6) 0.0398(6) 0.0024(4) 0.0088(5) 0.0008(5) 
C4 0.0350(6) 0.0334(6) 0.0423(6) -0.0059(5) 0.0053(5) 0.0063(5) 
C5 0.0313(5) 0.0363(6) 0.0335(6) -0.0113(4) 0.0093(4) -0.0011(4) 
C6 0.0316(5) 0.0303(5) 0.0273(5) -0.0076(4) 0.0055(4) -0.0047(4) 
C7 0.0508(8) 0.0453(7) 0.0346(6) 0.0011(5) 0.0131(5) 0.0008(6) 
N1 0.0263(4) 0.0321(5) 0.0306(5) -0.0076(3) 0.0028(3) 0.0014(4) 
C8 0.0507(7) 0.0426(7) 0.0351(6) 0.0085(5) 0.0146(5) 0.0160(6) 
C9 0.0447(7) 0.0477(7) 0.0375(6) 0.0062(5) 0.0088(5) 0.0238(6) 
  
_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 C1 1.3525(13) . ? 
O1 H1A 0.8400 . ? 
C1 C2 1.3893(16) . ? 
C1 C6 1.4084(15) . ? 
C2 C3 1.3863(16) . ? 
C2 H2 0.9500 . ? 
C3 C4 1.3890(17) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.3854(17) . ? 
C4 H4 0.9500 . ? 
C5 C6 1.3846(17) . ? 
C5 H5 0.9500 . ? 
C6 C7 1.5034(16) . ? 
C7 H7A 0.9800 . ? 
C7 H7B 0.9800 . ? 
C7 H7C 0.9800 . ? 
N1 C8 1.4598(15) . ? 
N1 C9 1.4633(15) . ? 
N1 H1 0.879(8) . ? 
C8 C9 1.5231(17) 3_666 ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 C8 1.5231(17) 3_666 ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
  
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 H1A 109.5 . . ? 
O1 C1 C2 122.90(10) . . ? 
O1 C1 C6 117.32(10) . . ? 
C2 C1 C6 119.76(10) . . ? 
C3 C2 C1 120.63(10) . . ? 
C3 C2 H2 119.7 . . ? 
C1 C2 H2 119.7 . . ? 
C2 C3 C4 120.22(11) . . ? 
C2 C3 H3 119.9 . . ? 
C4 C3 H3 119.9 . . ? 
C5 C4 C3 118.80(11) . . ? 
C5 C4 H4 120.6 . . ? 
C3 C4 H4 120.6 . . ? 
C6 C5 C4 122.29(10) . . ? 
C6 C5 H5 118.9 . . ? 
C4 C5 H5 118.9 . . ? 
C5 C6 C1 118.30(10) . . ? 
C5 C6 C7 121.86(10) . . ? 
C1 C6 C7 119.81(10) . . ? 
C6 C7 H7A 109.5 . . ? 
C6 C7 H7B 109.5 . . ? 
H7A C7 H7B 109.5 . . ? 
C6 C7 H7C 109.5 . . ? 
H7A C7 H7C 109.5 . . ? 
H7B C7 H7C 109.5 . . ? 
C8 N1 C9 110.16(9) . . ? 
C8 N1 H1 109.8(9) . . ? 
C9 N1 H1 106.8(9) . . ? 
N1 C8 C9 112.58(10) . 3_666 ? 
N1 C8 H8A 109.1 . . ? 
C9 C8 H8A 109.1 3_666 . ? 
N1 C8 H8B 109.1 . . ? 
C9 C8 H8B 109.1 3_666 . ? 
H8A C8 H8B 107.8 . . ? 
N1 C9 C8 112.89(10) . 3_666 ? 
N1 C9 H9A 109.0 . . ? 
C8 C9 H9A 109.0 3_666 . ? 
N1 C9 H9B 109.0 . . ? 
C8 C9 H9B 109.0 3_666 . ? 
H9A C9 H9B 107.8 . . ? 
  
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 
O1 C1 C2 C3 177.96(10) . . . . ? 
C6 C1 C2 C3 -0.42(17) . . . . ? 
C1 C2 C3 C4 0.55(18) . . . . ? 
C2 C3 C4 C5 -0.50(18) . . . . ? 
C3 C4 C5 C6 0.34(18) . . . . ? 
C4 C5 C6 C1 -0.22(17) . . . . ? 
C4 C5 C6 C7 -178.32(11) . . . . ? 
O1 C1 C6 C5 -178.22(9) . . . . ? 
C2 C1 C6 C5 0.26(16) . . . . ? 
O1 C1 C6 C7 -0.08(15) . . . . ? 
C2 C1 C6 C7 178.40(11) . . . . ? 
C9 N1 C8 C9 53.02(16) . . . 3_666 ? 
C8 N1 C9 C8 -53.20(17) . . . 3_666 ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
O1 H1A N1  0.84 1.89 2.7152(12) 168.7 1_655 
  
_diffrn_measured_fraction_theta_max    0.986 
_diffrn_reflns_theta_full              27.56 
_diffrn_measured_fraction_theta_full   0.986 
_refine_diff_density_max    0.262 
_refine_diff_density_min   -0.237 
_refine_diff_density_rms    0.037 
 
data_PC_PP
_database_code_depnum_ccdc_archive 'CCDC 1907017'
  
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C11 H18 N2 O' 
_chemical_formula_weight          194.27 
  
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' 
  
_symmetry_cell_setting            Orthorhombic 
_symmetry_space_group_name_H-M    P2(1)2(1)2(1) 
  
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x+1/2, -y, z+1/2' 
 '-x, y+1/2, -z+1/2' 
 'x+1/2, -y+1/2, -z' 
  
_cell_length_a                    5.9035(10) 
_cell_length_b                    8.3771(16) 
_cell_length_c                    21.980(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  90.00 
_cell_angle_gamma                 90.00 
_cell_volume                      1087.0(3) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     113(2) 
_cell_measurement_reflns_used           4015 
_cell_measurement_theta_min             3.1 
_cell_measurement_theta_max             27.5 
  
_exptl_crystal_description        Prism 
_exptl_crystal_colour             Colorless 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.18 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.187 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              424 
_exptl_absorpt_coefficient_mu     0.077 
_exptl_absorpt_correction_type    MULTI-SCAN 
_exptl_absorpt_correction_T_min   0.9848 
_exptl_absorpt_correction_T_max   0.9908 
_exptl_absorpt_process_details    'REQAB (Rigaku, 1998)' 
  
_exptl_special_details 
; 
 ? 
; 
  
_diffrn_ambient_temperature       113(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'rotating anode' 
_diffrn_radiation_monochromator   multilayer 
_diffrn_measurement_device_type   'Rigaku XtaLAB P200' 
_diffrn_measurement_method        'ω and φ scans' 
_diffrn_detector_area_resol_mean  5.814 
_diffrn_standards_number          0 
_diffrn_standards_interval_count  0 
_diffrn_standards_interval_time   0 
_diffrn_standards_decay_%         0 
_diffrn_reflns_number             13953 
_diffrn_reflns_av_R_equivalents   0.0152 
_diffrn_reflns_av_sigmaI/netI     0.0085 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -10 
_diffrn_reflns_limit_k_max        10 
_diffrn_reflns_limit_l_min        -28 
_diffrn_reflns_limit_l_max        28 
_diffrn_reflns_theta_min          3.06 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              2501 
_reflns_number_gt                 2450 
_reflns_threshold_expression      >2sigma(I) 
  
_computing_data_collection   'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)' 
_computing_cell_refinement    'CrystalClear-SM Expert 2.1 b42' 
_computing_data_reduction     'CrystalClear-SM Expert 2.1 b42' 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     'CrystalStructure 4.1' 
_computing_publication_material   'CrystalStructure 4.1 (Rigaku, 2014)' 
  
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
; 
  
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
 'calc w=1/[σ²(Fo²)+(0.0454P)²+0.1727P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     mixed 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_abs_structure_details 
 'Flack H D (1983), Acta Cryst. A39, 876-881' 
_refine_ls_abs_structure_Flack    1.0(10) 
_refine_ls_number_reflns          2501 
_refine_ls_number_parameters      140 
_refine_ls_number_restraints      3 
_refine_ls_R_factor_all           0.0278 
_refine_ls_R_factor_gt            0.0273 
_refine_ls_wR_factor_ref          0.0758 
_refine_ls_wR_factor_gt           0.0754 
_refine_ls_goodness_of_fit_ref    1.071 
_refine_ls_restrained_S_all       1.071 
_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_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
O1 O 0.39211(13) 0.63315(9) 0.33726(3) 0.02266(17) Uani 1 1 d D . . 
N1 N 0.90704(15) 0.94136(10) 0.21857(4) 0.01684(17) Uani 1 1 d D . . 
N2 N 0.90347(15) 0.62322(10) 0.17321(4) 0.01810(18) Uani 1 1 d D . . 
C1 C 0.1148(2) 1.06978(13) 0.52140(5) 0.0257(2) Uani 1 1 d . . . 
H1A H 0.1361 1.0192 0.5612 0.039 Uiso 1 1 calc R . . 
H1B H -0.0453 1.0973 0.5160 0.039 Uiso 1 1 calc R . . 
H1C H 0.2069 1.1669 0.5191 0.039 Uiso 1 1 calc R . . 
C2 C 0.18682(18) 0.95544(11) 0.47181(4) 0.01729(19) Uani 1 1 d . . . 
C3 C 0.40116(18) 0.96339(11) 0.44497(4) 0.0187(2) Uani 1 1 d . . . 
H3 H 0.5043 1.0437 0.4578 0.022 Uiso 1 1 calc R . . 
C4 C 0.46673(16) 0.85630(12) 0.39988(4) 0.0183(2) Uani 1 1 d . . . 
H4 H 0.6128 0.8650 0.3821 0.022 Uiso 1 1 calc R . . 
C5 C 0.31938(17) 0.73627(11) 0.38066(4) 0.01672(19) Uani 1 1 d . . . 
C6 C 0.10444(18) 0.72662(11) 0.40730(4) 0.01792(19) Uani 1 1 d . . . 
H6 H 0.0015 0.6460 0.3947 0.022 Uiso 1 1 calc R . . 
C7 C 0.04103(17) 0.83510(11) 0.45229(4) 0.0177(2) Uani 1 1 d . . . 
H7 H -0.1052 0.8268 0.4701 0.021 Uiso 1 1 calc R . . 
C8 C 0.75804(17) 0.81811(12) 0.24503(4) 0.0175(2) Uani 1 1 d . . . 
H8A H 0.6190 0.8686 0.2613 0.021 Uiso 1 1 calc R . . 
H8B H 0.8368 0.7640 0.2790 0.021 Uiso 1 1 calc R . . 
C9 C 0.69543(18) 0.69674(12) 0.19657(4) 0.0190(2) Uani 1 1 d . . . 
H9A H 0.5956 0.6138 0.2142 0.023 Uiso 1 1 calc R . . 
H9B H 0.6129 0.7500 0.1630 0.023 Uiso 1 1 calc R . . 
C10 C 1.04757(17) 0.74491(12) 0.14504(4) 0.0196(2) Uani 1 1 d . . . 
H10A H 0.9649 0.7977 0.1114 0.024 Uiso 1 1 calc R . . 
H10B H 1.1855 0.6945 0.1281 0.024 Uiso 1 1 calc R . . 
C11 C 1.11294(17) 0.86751(12) 0.19295(4) 0.01859(19) Uani 1 1 d . . . 
H11A H 1.2003 0.8151 0.2258 0.022 Uiso 1 1 calc R . . 
H11B H 1.2098 0.9508 0.1744 0.022 Uiso 1 1 calc R . . 
H1 H 0.952(2) 1.0047(14) 0.2491(5) 0.025(3) Uiso 1 1 d D . . 
H2 H 0.861(2) 0.5524(15) 0.1451(5) 0.032(4) Uiso 1 1 d D . . 
H1D H 0.281(2) 0.5751(19) 0.3238(8) 0.054(5) Uiso 1 1 d D . . 
  
loop_ 
 _atom_site_aniso_label 
 _atom_site_aniso_U_11 
 _atom_site_aniso_U_22 
 _atom_site_aniso_U_33 
 _atom_site_aniso_U_23 
 _atom_site_aniso_U_13 
 _atom_site_aniso_U_12 
O1 0.0204(3) 0.0234(4) 0.0242(4) -0.0073(3) 0.0032(3) -0.0020(3) 
N1 0.0184(4) 0.0135(3) 0.0186(4) -0.0007(3) 0.0005(3) -0.0013(3) 
N2 0.0208(4) 0.0150(4) 0.0185(4) -0.0035(3) -0.0013(3) -0.0010(3) 
C1 0.0300(5) 0.0241(5) 0.0231(5) -0.0063(4) -0.0009(4) 0.0017(5) 
C2 0.0206(4) 0.0161(4) 0.0152(4) 0.0015(3) -0.0030(4) 0.0020(4) 
C3 0.0197(4) 0.0176(4) 0.0188(4) 0.0012(4) -0.0056(4) -0.0041(4) 
C4 0.0146(4) 0.0217(5) 0.0185(4) 0.0026(4) -0.0015(4) -0.0015(4) 
C5 0.0175(4) 0.0165(4) 0.0161(4) 0.0010(3) -0.0008(4) 0.0007(4) 
C6 0.0174(4) 0.0167(4) 0.0197(4) 0.0000(3) -0.0015(4) -0.0039(4) 
C7 0.0161(4) 0.0196(4) 0.0172(4) 0.0026(3) 0.0005(3) 0.0003(4) 
C8 0.0186(4) 0.0164(4) 0.0175(4) 0.0002(3) 0.0022(3) 0.0001(4) 
C9 0.0161(4) 0.0187(4) 0.0221(5) -0.0002(4) 0.0000(4) -0.0032(4) 
C10 0.0195(4) 0.0228(5) 0.0166(4) -0.0003(4) 0.0029(4) 0.0007(4) 
C11 0.0153(4) 0.0186(4) 0.0219(4) 0.0007(4) 0.0001(4) -0.0011(4) 
  
_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 C5 1.3568(12) . ? 
O1 H1D 0.869(9) . ? 
N1 C11 1.4755(13) . ? 
N1 C8 1.4758(12) . ? 
N1 H1 0.896(8) . ? 
N2 C10 1.4650(13) . ? 
N2 C9 1.4667(13) . ? 
N2 H2 0.892(9) . ? 
C1 C2 1.5120(14) . ? 
C1 H1A 0.9800 . ? 
C1 H1B 0.9800 . ? 
C1 H1C 0.9800 . ? 
C2 C7 1.3933(14) . ? 
C2 C3 1.3978(14) . ? 
C3 C4 1.3916(14) . ? 
C3 H3 0.9500 . ? 
C4 C5 1.3951(14) . ? 
C4 H4 0.9500 . ? 
C5 C6 1.3998(14) . ? 
C6 C7 1.3942(14) . ? 
C6 H6 0.9500 . ? 
C7 H7 0.9500 . ? 
C8 C9 1.5182(13) . ? 
C8 H8A 0.9900 . ? 
C8 H8B 0.9900 . ? 
C9 H9A 0.9900 . ? 
C9 H9B 0.9900 . ? 
C10 C11 1.5208(14) . ? 
C10 H10A 0.9900 . ? 
C10 H10B 0.9900 . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
  
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 
C5 O1 H1D 110.9(12) . . ? 
C11 N1 C8 110.37(8) . . ? 
C11 N1 H1 106.9(9) . . ? 
C8 N1 H1 107.2(9) . . ? 
C10 N2 C9 110.00(8) . . ? 
C10 N2 H2 109.5(10) . . ? 
C9 N2 H2 106.7(10) . . ? 
C2 C1 H1A 109.5 . . ? 
C2 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
C2 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
C7 C2 C3 117.62(9) . . ? 
C7 C2 C1 120.45(9) . . ? 
C3 C2 C1 121.92(9) . . ? 
C4 C3 C2 121.45(9) . . ? 
C4 C3 H3 119.3 . . ? 
C2 C3 H3 119.3 . . ? 
C3 C4 C5 120.46(9) . . ? 
C3 C4 H4 119.8 . . ? 
C5 C4 H4 119.8 . . ? 
O1 C5 C4 118.33(9) . . ? 
O1 C5 C6 122.97(9) . . ? 
C4 C5 C6 118.70(9) . . ? 
C7 C6 C5 120.16(9) . . ? 
C7 C6 H6 119.9 . . ? 
C5 C6 H6 119.9 . . ? 
C2 C7 C6 121.62(9) . . ? 
C2 C7 H7 119.2 . . ? 
C6 C7 H7 119.2 . . ? 
N1 C8 C9 109.70(8) . . ? 
N1 C8 H8A 109.7 . . ? 
C9 C8 H8A 109.7 . . ? 
N1 C8 H8B 109.7 . . ? 
C9 C8 H8B 109.7 . . ? 
H8A C8 H8B 108.2 . . ? 
N2 C9 C8 108.84(8) . . ? 
N2 C9 H9A 109.9 . . ? 
C8 C9 H9A 109.9 . . ? 
N2 C9 H9B 109.9 . . ? 
C8 C9 H9B 109.9 . . ? 
H9A C9 H9B 108.3 . . ? 
N2 C10 C11 108.94(8) . . ? 
N2 C10 H10A 109.9 . . ? 
C11 C10 H10A 109.9 . . ? 
N2 C10 H10B 109.9 . . ? 
C11 C10 H10B 109.9 . . ? 
H10A C10 H10B 108.3 . . ? 
N1 C11 C10 109.78(8) . . ? 
N1 C11 H11A 109.7 . . ? 
C10 C11 H11A 109.7 . . ? 
N1 C11 H11B 109.7 . . ? 
C10 C11 H11B 109.7 . . ? 
H11A C11 H11B 108.2 . . ? 
  
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 
C7 C2 C3 C4 0.64(14) . . . . ? 
C1 C2 C3 C4 179.19(9) . . . . ? 
C2 C3 C4 C5 -0.65(14) . . . . ? 
C3 C4 C5 O1 -179.00(8) . . . . ? 
C3 C4 C5 C6 0.43(14) . . . . ? 
O1 C5 C6 C7 179.15(9) . . . . ? 
C4 C5 C6 C7 -0.25(14) . . . . ? 
C3 C2 C7 C6 -0.46(14) . . . . ? 
C1 C2 C7 C6 -179.03(9) . . . . ? 
C5 C6 C7 C2 0.27(14) . . . . ? 
C11 N1 C8 C9 -58.19(10) . . . . ? 
C10 N2 C9 C8 -61.73(10) . . . . ? 
N1 C8 C9 N2 59.51(10) . . . . ? 
C9 N2 C10 C11 61.48(10) . . . . ? 
C8 N1 C11 C10 57.92(10) . . . . ? 
N2 C10 C11 N1 -59.06(10) . . . . ? 
  
loop_ 
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
N1 H1 N2  0.896(8) 2.152(9) 3.0382(12) 170.2(13) 3_755 
O1 H1D N1  0.869(9) 1.831(10) 2.6843(12) 166.7(18) 3_645 
  
_diffrn_measured_fraction_theta_max    0.997 
_diffrn_reflns_theta_full              27.50 
_diffrn_measured_fraction_theta_full   0.997 
_refine_diff_density_max    0.190 
_refine_diff_density_min   -0.170 
_refine_diff_density_rms    0.033 
