##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in          #
# Acta Crystallographica Section E. It conforms to the requirements of       #
# Notes for Authors for Acta Crystallographica Section E, and has been       #
# peer reviewed under the auspices of the IUCr Commission on Journals.       #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic.                                       #
#                                                                            #
# Software is freely available for graphical display of the structure(s)     #
# in this CIF. For information consult the CIF software page                 #
# http://www.iucr.org/resources/cif/software.                                #
#                                                                            #
# This file may be used for bona fide research purposes within the           #
# scientific community so long as proper attribution is given to the journal # 
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data_I
_database_code_depnum_ccdc_archive 'CCDC 1432732'
_audit_creation_method     SHELXL-2014/6
_journal_data_validation_number     ?
_journal_date_recd_electronic     2015-10-10
_journal_date_accepted     2015-10-22
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2015
_journal_volume     71
_journal_issue     11
_journal_page_first     1401
_journal_page_last     1407
_journal_paper_category     GO
_journal_paper_doi     10.1107/S2056989015020046
_journal_coeditor_code     PK2566
_publ_contact_author
;
Jeffery A. Bertke
University of Illinois
School of Chemical Sciences, Box 59-1
505 South Mathews Avenue
Urbana, Illinois  61801
USA
;
_publ_contact_author_name     ?
_publ_contact_author_address     ?
_publ_contact_author_email     'jbertke@illinois.edu'
_publ_contact_author_fax     ?
_publ_contact_author_phone
;
1  217 300 6645
;
_publ_section_title
;\
Crystal structure and absolute configuration of
(3S,4aS,8aS)-N-tert-butyl-2-[(S)-3-\
(2-chloro-4-nitrobenzamido)-2-hydroxypropyl]decahydroisoquinoline-3-\
carboxamide and
(3S,4aS,8aS)-N-tert-butyl-2-{(S)-2-\
[(S)-1-(2-chloro-4-nitrobenzoyl)pyrrolidin-2-yl]-2-hydroxyethyl}\
decahydroisoquinoline-3-carboxamide
;
_publ_section_title_footnote     .
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Maxson, Tucker' .
;
Department of Chemistry
University of Illinois
345 Roger Adams Lab
600 South Mathews Avenue
Urbana, IL 61801
USA
;
    'Bertke, Jeffery A.' .
;
University of Illinois
School of Chemical Sciences, Box 59-1
505 South Mathews Avenue
Urbana, Illinois 61801
USA
;
    'Gray, Danielle L.' .
;
University of Illinois
School of Chemical Sciences, Box 59-1
505 South Mathews Avenue
Urbana, Illinois 61801
USA
;
    'Mitchell, Douglas A.' .
;
Department of Chemistry
University of Illinois
345 Roger Adams Lab
600 South Mathews Avenue
Urbana, IL 61801
USA
;
_publ_section_synopsis
;
The crystal structure and absolute configuration of two new nelfinavir analogs
have been determined. Intermolecular hydrogen bonding leads to two-dimensional
sheets in one analog and one-dimensional chains in the other.
;
_chemical_name_systematic
;\
(3S,4aS,8aS)-N-tert-Butyl-\
2-[(S)-3-(2-chloro-4-nitrobenzamido)-2-hydroxypropyl]\
decahydroisoquinoline-3-carboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C24 H35 Cl N4 O5'
_chemical_formula_sum     'C24 H35 Cl N4 O5'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C24 H35 Cl N4 O5'
_chemical_formula_weight     495.01
_chemical_melting_point     ?
_symmetry_cell_setting     orthorhombic
_symmetry_space_group_name_H-M     'P2(1)2(1)2 '
_symmetry_space_group_name_Hall     'P 2 2ab'
_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.
;
_space_group_crystal_system     orthorhombic
_space_group_name_H-M_alt     'P 21 21 2'
_space_group_name_Hall     'P 2 2ab'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, -y, z'
    '-x+1/2, y+1/2, -z'
    'x+1/2, -y+1/2, -z'
_cell_length_a     18.8408(7)
_cell_length_b     20.2263(8)
_cell_length_c     6.7923(3)
_cell_angle_alpha     90
_cell_angle_beta     90
_cell_angle_gamma     90
_cell_volume     2588.41(18)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     9966
_cell_measurement_theta_min     2.29
_cell_measurement_theta_max     24.52
_cell_measurement_temperature     193(2)
_exptl_crystal_description     'prism'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.368
_exptl_crystal_size_mid     0.356
_exptl_crystal_size_min     0.286
_exptl_crystal_density_diffrn     1.270
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1056
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    -2.00 1.00 0.00 0.1550
    2.00 -1.00 0.00 0.1440
    0.00 2.00 1.00 0.1300
    0.00 -2.00 -1.00 0.1430
    2.00 0.00 -1.00 0.1820
    1.00 1.00 0.00 0.1540
    -2.00 -4.00 1.00 0.1260
    -1.00 -2.00 -2.00 0.1510
    1.00 2.00 0.00 0.1640
    -1.00 -2.00 2.00 0.1290
    2.00 1.00 1.00 0.1260
    -1.00 3.00 0.00 0.1470
    -3.00 3.00 -1.00 0.1730
    -1.00 -3.00 -1.00 0.1510
    -1.00 2.00 -2.00 0.1690
    0.00 -1.00 0.00 0.1670
    4.00 1.00 0.00 0.1230
    -4.00 1.00 1.00 0.1530
    -4.00 -1.00 0.00 0.1870
_exptl_absorpt_coefficient_mu     0.188
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(SHELXTL/XPREP; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.934
_shelx_estimated_absorpt_T_max     0.948
_exptl_absorpt_correction_T_min     0.9526
_exptl_absorpt_correction_T_max     0.9604
_exptl_special_details
;
One distinct cell was identified using APEX2 (Bruker, 2014). Four frame
series were integrated and filtered for statistical outliers using
SAINT (Bruker, 2014) then corrected for absorption by integration using
SHELXTL/XPREP V2005/2 (Bruker, 2014) before using
SAINT/SADABS (Bruker, 2014) to sort, merge, and scale the
combined data No decay correction was applied.
;
_diffrn_ambient_temperature     193(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Siemens Platform/APEXII CCD'
_diffrn_measurement_method     'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     30342
_diffrn_reflns_av_R_equivalents     0.0265
_diffrn_reflns_theta_min     1.477
_diffrn_reflns_theta_max     26.279
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     0.999
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -23
_diffrn_reflns_limit_h_max     23
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -8
_diffrn_reflns_limit_l_max     8
_diffrn_standards_number     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Structure was phased by direct (Sheldrick, 2015). Systematic conditions
suggested the ambiguous space group. The space group choice was confirmed by
successful convergence of the full-matrix least-squares refinement on
F². The final map had no significant features. A final analysis of
variance between observed and calculated structure factors showed no
dependence on amplitude or resolution.
;
_reflns_number_total     5243
_reflns_number_gt     4694
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0407
_refine_ls_R_factor_gt     0.0351
_refine_ls_wR_factor_gt     0.0819
_refine_ls_wR_factor_ref     0.0854
_refine_ls_goodness_of_fit_ref     1.027
_refine_ls_restrained_S_all     1.041
_refine_ls_number_reflns     5243
_refine_ls_number_parameters     333
_refine_ls_number_restraints     53
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0355P)²+0.5785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.001
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.343
_refine_diff_density_min     -0.434
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack (1983); Hooft et al. (2008); 2720 Friedels
;
_refine_ls_abs_structure_Flack     -0.008(18)
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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014), XPREP (Bruker, 2014), and SADABS (Bruker,
2014)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008) and CrystalMaker (CrystalMaker, 1994)
;
_computing_publication_material
;
XCIF (Bruker, 2014) and publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.29551(15) 0.69804(7) 0.67519(15) 0.0735(5) Uani d 0.941(8) A 1
    Cl Cl1B 0.326(2) 0.6888(7) 0.664(3) 0.0735(5) Uani d 0.059(8) A 2
    O O1 0.3558(8) 0.8988(8) 0.2519(16) 0.086(2) Uani d 0.60(2) B 1
    O O2 0.4046(8) 0.9713(5) 0.445(2) 0.116(3) Uani d 0.60(2) B 1
    N N1 0.3808(6) 0.9169(5) 0.4064(12) 0.0715(17) Uani d 0.60(2) B 1
    O O1B 0.3725(13) 0.9134(12) 0.271(3) 0.086(2) Uani d 0.40(2) B 2
    O O2B 0.4360(11) 0.9754(7) 0.453(3) 0.116(3) Uani d 0.40(2) B 2
    N N1B 0.3991(9) 0.9260(7) 0.431(2) 0.0715(17) Uani d 0.40(2) B 2
    C C1 0.38040(11) 0.78173(14) 0.8790(4) 0.0477(6) Uani d 1 . .
    C C2 0.34335(12) 0.77084(14) 0.7057(4) 0.0520(7) Uani d 1 . .
    C C3 0.34488(14) 0.81498(16) 0.5532(4) 0.0585(7) Uani d 1 . .
    H H3A 0.3207 0.8062 0.4333 0.070 Uiso calc 1 . .
    C C4 0.38270(16) 0.87247(16) 0.5797(5) 0.0635(8) Uani d 1 . .
    C C5 0.41913(17) 0.88668(15) 0.7505(5) 0.0675(8) Uani d 1 . .
    H H5A 0.4439 0.9272 0.7658 0.081 Uiso calc 1 . .
    C C6 0.41831(14) 0.84036(15) 0.8974(5) 0.0594(7) Uani d 1 . .
    H H6A 0.4443 0.8485 1.0148 0.071 Uiso calc 1 . .
    C C7 0.38161(12) 0.73281(14) 1.0445(4) 0.0478(6) Uani d 1 . .
    O O3 0.32755(9) 0.71943(11) 1.1373(3) 0.0644(5) Uani d 1 . .
    O O4 0.48956(9) 0.73984(10) 1.4849(3) 0.0534(5) Uani d 1 . .
    H H4B 0.5165(17) 0.7479(17) 1.585(5) 0.080 Uiso d 1 . .
    O O5 0.56221(7) 0.75831(7) 0.8387(2) 0.0372(3) Uani d 1 . .
    N N2 0.44567(10) 0.70759(11) 1.0807(3) 0.0438(5) Uani d 1 . .
    H H2 0.4786(16) 0.7171(15) 1.005(5) 0.066 Uiso d 1 . .
    N N3 0.60919(9) 0.66293(9) 1.1177(3) 0.0368(4) Uani d 1 . .
    N N4 0.67223(10) 0.80363(9) 0.8528(3) 0.0417(4) Uani d 1 . .
    H H4 0.7145(16) 0.7950(14) 0.884(4) 0.063 Uiso d 1 . .
    C C8 0.46111(12) 0.66114(13) 1.2385(4) 0.0459(6) Uani d 1 . .
    H H8A 0.4766 0.6186 1.1805 0.055 Uiso calc 1 . .
    H H8B 0.4172 0.6528 1.3145 0.055 Uiso calc 1 . .
    C C9 0.51828(11) 0.68604(12) 1.3772(3) 0.0420(5) Uani d 1 . .
    H H9A 0.5310 0.6499 1.4712 0.050 Uiso calc 1 . .
    C C10 0.58565(11) 0.70901(12) 1.2713(3) 0.0386(5) Uani d 1 . .
    H H10A 0.5767 0.7528 1.2109 0.046 Uiso calc 1 . .
    H H10B 0.6242 0.7144 1.3691 0.046 Uiso calc 1 . .
    C C11 0.65713(11) 0.69212(11) 0.9715(3) 0.0380(5) Uani d 1 . .
    H H11A 0.7036 0.7026 1.0353 0.046 Uiso calc 1 . .
    C C12 0.66899(13) 0.64166(11) 0.8056(4) 0.0410(5) Uani d 1 . .
    H H12A 0.6230 0.6318 0.7413 0.049 Uiso calc 1 . .
    H H12B 0.7010 0.6610 0.7054 0.049 Uiso calc 1 . .
    C C13 0.70138(14) 0.57736(12) 0.8829(4) 0.0494(6) Uani d 1 . .
    H H13A 0.7500 0.5880 0.9326 0.059 Uiso calc 1 . .
    C C14 0.70957(16) 0.52528(13) 0.7203(4) 0.0590(7) Uani d 1 . .
    H H14A 0.7303 0.5467 0.6025 0.071 Uiso calc 1 . .
    H H14B 0.7434 0.4910 0.7656 0.071 Uiso calc 1 . .
    C C15 0.64047(16) 0.49205(14) 0.6624(4) 0.0611(7) Uani d 1 . .
    H H15A 0.6503 0.4565 0.5661 0.073 Uiso calc 1 . .
    H H15B 0.6089 0.5248 0.5988 0.073 Uiso calc 1 . .
    C C16 0.60342(19) 0.46287(13) 0.8419(5) 0.0696(9) Uani d 1 . .
    H H16A 0.6333 0.4276 0.8999 0.084 Uiso calc 1 . .
    H H16B 0.5576 0.4430 0.8019 0.084 Uiso calc 1 . .
    C C17 0.59030(17) 0.51683(13) 0.9945(4) 0.0610(8) Uani d 1 . .
    H H17A 0.5575 0.5502 0.9387 0.073 Uiso calc 1 . .
    H H17B 0.5671 0.4971 1.1115 0.073 Uiso calc 1 . .
    C C18 0.65836(16) 0.55060(13) 1.0574(4) 0.0550(7) Uani d 1 . .
    H H18A 0.6883 0.5165 1.1243 0.066 Uiso calc 1 . .
    C C19 0.64454(15) 0.60538(13) 1.2068(4) 0.0505(6) Uani d 1 . .
    H H19A 0.6145 0.5878 1.3143 0.061 Uiso calc 1 . .
    H H19B 0.6902 0.6196 1.2650 0.061 Uiso calc 1 . .
    C C20 0.62618(10) 0.75493(11) 0.8828(3) 0.0354(5) Uani d 1 . .
    C C21 0.65543(13) 0.87079(12) 0.7767(4) 0.0480(6) Uani d 1 . .
    C C22 0.60827(17) 0.90585(14) 0.9239(5) 0.0679(8) Uani d 1 . .
    H H22A 0.5644 0.8805 0.9422 0.102 Uiso calc 1 . .
    H H22B 0.5967 0.9501 0.8746 0.102 Uiso calc 1 . .
    H H22C 0.6332 0.9097 1.0500 0.102 Uiso calc 1 . .
    C C23 0.62113(16) 0.86682(14) 0.5736(5) 0.0606(8) Uani d 1 . .
    H H23A 0.5739 0.8468 0.5852 0.091 Uiso calc 1 . .
    H H23B 0.6507 0.8397 0.4866 0.091 Uiso calc 1 . .
    H H23C 0.6167 0.9114 0.5184 0.091 Uiso calc 1 . .
    C C24 0.72639(15) 0.90696(15) 0.7599(6) 0.0682(9) Uani d 1 . .
    H H24A 0.7496 0.9079 0.8890 0.102 Uiso calc 1 . .
    H H24B 0.7182 0.9523 0.7145 0.102 Uiso calc 1 . .
    H H24C 0.7569 0.8838 0.6655 0.102 Uiso calc 1 . .
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C2 . 1.739(3) ?
    Cl1B C2 . 1.716(12) ?
    O1 N1 . 1.207(7) ?
    O2 N1 . 1.217(7) ?
    N1 C4 . 1.482(7) ?
    O1B N1B . 1.226(9) ?
    O2B N1B . 1.228(10) ?
    N1B C4 . 1.511(9) ?
    C1 C2 . 1.386(3) ?
    C1 C6 . 1.390(4) ?
    C1 C7 . 1.498(4) ?
    C2 C3 . 1.368(4) ?
    C3 C4 . 1.376(5) ?
    C3 H3A . 0.9500 ?
    C4 C5 . 1.379(5) ?
    C5 C6 . 1.368(4) ?
    C5 H5A . 0.9500 ?
    C6 H6A . 0.9500 ?
    C7 O3 . 1.228(3) ?
    C7 N2 . 1.333(3) ?
    O4 C9 . 1.418(3) ?
    O4 H4B . 0.87(4) ?
    O5 C20 . 1.244(2) ?
    N2 C8 . 1.455(3) ?
    N2 H2 . 0.83(3) ?
    N3 C11 . 1.467(3) ?
    N3 C10 . 1.467(3) ?
    N3 C19 . 1.471(3) ?
    N4 C20 . 1.329(3) ?
    N4 C21 . 1.487(3) ?
    N4 H4 . 0.84(3) ?
    C8 C9 . 1.517(3) ?
    C8 H8A . 0.9900 ?
    C8 H8B . 0.9900 ?
    C9 C10 . 1.531(3) ?
    C9 H9A . 1.0000 ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 C20 . 1.522(3) ?
    C11 C12 . 1.536(3) ?
    C11 H11A . 1.0000 ?
    C12 C13 . 1.529(3) ?
    C12 H12A . 0.9900 ?
    C12 H12B . 0.9900 ?
    C13 C14 . 1.534(4) ?
    C13 C18 . 1.535(4) ?
    C13 H13A . 1.0000 ?
    C14 C15 . 1.517(4) ?
    C14 H14A . 0.9900 ?
    C14 H14B . 0.9900 ?
    C15 C16 . 1.524(4) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.525(4) ?
    C16 H16A . 0.9900 ?
    C16 H16B . 0.9900 ?
    C17 C18 . 1.514(4) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 C19 . 1.525(4) ?
    C18 H18A . 1.0000 ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C21 C22 . 1.514(4) ?
    C21 C23 . 1.526(4) ?
    C21 C24 . 1.528(3) ?
    C22 H22A . 0.9800 ?
    C22 H22B . 0.9800 ?
    C22 H22C . 0.9800 ?
    C23 H23A . 0.9800 ?
    C23 H23B . 0.9800 ?
    C23 H23C . 0.9800 ?
    C24 H24A . 0.9800 ?
    C24 H24B . 0.9800 ?
    C24 H24C . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1 N1 O2 . . 127.3(9) ?
    O1 N1 C4 . . 121.0(9) ?
    O2 N1 C4 . . 111.6(9) ?
    O1B N1B O2B . . 120.6(14) ?
    O1B N1B C4 . . 111.2(14) ?
    O2B N1B C4 . . 128.1(14) ?
    C2 C1 C6 . . 118.1(3) ?
    C2 C1 C7 . . 122.7(2) ?
    C6 C1 C7 . . 119.2(2) ?
    C3 C2 C1 . . 121.9(3) ?
    C3 C2 Cl1B . . 120.7(7) ?
    C1 C2 Cl1B . . 113.0(8) ?
    C3 C2 Cl1 . . 118.2(2) ?
    C1 C2 Cl1 . . 119.8(2) ?
    C2 C3 C4 . . 117.6(3) ?
    C2 C3 H3A . . 121.2 ?
    C4 C3 H3A . . 121.2 ?
    C3 C4 C5 . . 123.0(3) ?
    C3 C4 N1 . . 113.4(5) ?
    C5 C4 N1 . . 123.7(5) ?
    C3 C4 N1B . . 128.6(7) ?
    C5 C4 N1B . . 108.1(7) ?
    C6 C5 C4 . . 117.7(3) ?
    C6 C5 H5A . . 121.1 ?
    C4 C5 H5A . . 121.1 ?
    C5 C6 C1 . . 121.6(3) ?
    C5 C6 H6A . . 119.2 ?
    C1 C6 H6A . . 119.2 ?
    O3 C7 N2 . . 124.9(3) ?
    O3 C7 C1 . . 121.2(2) ?
    N2 C7 C1 . . 113.9(2) ?
    C9 O4 H4B . . 109(2) ?
    C7 N2 C8 . . 124.3(2) ?
    C7 N2 H2 . . 118(2) ?
    C8 N2 H2 . . 117(2) ?
    C11 N3 C10 . . 114.32(17) ?
    C11 N3 C19 . . 108.55(18) ?
    C10 N3 C19 . . 110.33(18) ?
    C20 N4 C21 . . 126.27(19) ?
    C20 N4 H4 . . 115(2) ?
    C21 N4 H4 . . 119(2) ?
    N2 C8 C9 . . 112.7(2) ?
    N2 C8 H8A . . 109.1 ?
    C9 C8 H8A . . 109.1 ?
    N2 C8 H8B . . 109.1 ?
    C9 C8 H8B . . 109.1 ?
    H8A C8 H8B . . 107.8 ?
    O4 C9 C8 . . 107.70(19) ?
    O4 C9 C10 . . 109.00(19) ?
    C8 C9 C10 . . 113.42(19) ?
    O4 C9 H9A . . 108.9 ?
    C8 C9 H9A . . 108.9 ?
    C10 C9 H9A . . 108.9 ?
    N3 C10 C9 . . 113.06(18) ?
    N3 C10 H10A . . 109.0 ?
    C9 C10 H10A . . 109.0 ?
    N3 C10 H10B . . 109.0 ?
    C9 C10 H10B . . 109.0 ?
    H10A C10 H10B . . 107.8 ?
    N3 C11 C20 . . 111.60(17) ?
    N3 C11 C12 . . 108.59(18) ?
    C20 C11 C12 . . 108.67(18) ?
    N3 C11 H11A . . 109.3 ?
    C20 C11 H11A . . 109.3 ?
    C12 C11 H11A . . 109.3 ?
    C13 C12 C11 . . 111.81(19) ?
    C13 C12 H12A . . 109.3 ?
    C11 C12 H12A . . 109.3 ?
    C13 C12 H12B . . 109.3 ?
    C11 C12 H12B . . 109.3 ?
    H12A C12 H12B . . 107.9 ?
    C12 C13 C14 . . 112.2(2) ?
    C12 C13 C18 . . 110.74(19) ?
    C14 C13 C18 . . 111.5(2) ?
    C12 C13 H13A . . 107.4 ?
    C14 C13 H13A . . 107.4 ?
    C18 C13 H13A . . 107.4 ?
    C15 C14 C13 . . 113.9(2) ?
    C15 C14 H14A . . 108.8 ?
    C13 C14 H14A . . 108.8 ?
    C15 C14 H14B . . 108.8 ?
    C13 C14 H14B . . 108.8 ?
    H14A C14 H14B . . 107.7 ?
    C14 C15 C16 . . 110.9(3) ?
    C14 C15 H15A . . 109.5 ?
    C16 C15 H15A . . 109.5 ?
    C14 C15 H15B . . 109.5 ?
    C16 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 108.0 ?
    C15 C16 C17 . . 109.9(2) ?
    C15 C16 H16A . . 109.7 ?
    C17 C16 H16A . . 109.7 ?
    C15 C16 H16B . . 109.7 ?
    C17 C16 H16B . . 109.7 ?
    H16A C16 H16B . . 108.2 ?
    C18 C17 C16 . . 112.2(3) ?
    C18 C17 H17A . . 109.2 ?
    C16 C17 H17A . . 109.2 ?
    C18 C17 H17B . . 109.2 ?
    C16 C17 H17B . . 109.2 ?
    H17A C17 H17B . . 107.9 ?
    C17 C18 C19 . . 111.8(2) ?
    C17 C18 C13 . . 112.8(2) ?
    C19 C18 C13 . . 110.4(2) ?
    C17 C18 H18A . . 107.2 ?
    C19 C18 H18A . . 107.2 ?
    C13 C18 H18A . . 107.2 ?
    N3 C19 C18 . . 112.3(2) ?
    N3 C19 H19A . . 109.2 ?
    C18 C19 H19A . . 109.2 ?
    N3 C19 H19B . . 109.2 ?
    C18 C19 H19B . . 109.2 ?
    H19A C19 H19B . . 107.9 ?
    O5 C20 N4 . . 123.7(2) ?
    O5 C20 C11 . . 120.82(19) ?
    N4 C20 C11 . . 115.44(18) ?
    N4 C21 C22 . . 108.9(2) ?
    N4 C21 C23 . . 110.9(2) ?
    C22 C21 C23 . . 111.9(2) ?
    N4 C21 C24 . . 106.1(2) ?
    C22 C21 C24 . . 109.8(2) ?
    C23 C21 C24 . . 109.2(2) ?
    C21 C22 H22A . . 109.5 ?
    C21 C22 H22B . . 109.5 ?
    H22A C22 H22B . . 109.5 ?
    C21 C22 H22C . . 109.5 ?
    H22A C22 H22C . . 109.5 ?
    H22B C22 H22C . . 109.5 ?
    C21 C23 H23A . . 109.5 ?
    C21 C23 H23B . . 109.5 ?
    H23A C23 H23B . . 109.5 ?
    C21 C23 H23C . . 109.5 ?
    H23A C23 H23C . . 109.5 ?
    H23B C23 H23C . . 109.5 ?
    C21 C24 H24A . . 109.5 ?
    C21 C24 H24B . . 109.5 ?
    H24A C24 H24B . . 109.5 ?
    C21 C24 H24C . . 109.5 ?
    H24A C24 H24C . . 109.5 ?
    H24B C24 H24C . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C6 C1 C2 C3 . . . . 1.8(4) ?
    C7 C1 C2 C3 . . . . -177.6(2) ?
    C6 C1 C2 Cl1B . . . . 158.4(14) ?
    C7 C1 C2 Cl1B . . . . -20.9(14) ?
    C6 C1 C2 Cl1 . . . . 179.7(2) ?
    C7 C1 C2 Cl1 . . . . 0.3(3) ?
    C1 C2 C3 C4 . . . . -2.3(4) ?
    Cl1B C2 C3 C4 . . . . -157.2(15) ?
    Cl1 C2 C3 C4 . . . . 179.8(2) ?
    C2 C3 C4 C5 . . . . 0.7(4) ?
    C2 C3 C4 N1 . . . . -179.8(5) ?
    C2 C3 C4 N1B . . . . 173.4(9) ?
    O1 N1 C4 C3 . . . . -9.0(13) ?
    O2 N1 C4 C3 . . . . 168.9(8) ?
    O1 N1 C4 C5 . . . . 170.5(10) ?
    O2 N1 C4 C5 . . . . -11.6(11) ?
    O1B N1B C4 C3 . . . . 1(2) ?
    O2B N1B C4 C3 . . . . -175.8(15) ?
    O1B N1B C4 C5 . . . . 174.8(17) ?
    O2B N1B C4 C5 . . . . -2(2) ?
    C3 C4 C5 C6 . . . . 1.4(4) ?
    N1 C4 C5 C6 . . . . -178.1(6) ?
    N1B C4 C5 C6 . . . . -172.6(8) ?
    C4 C5 C6 C1 . . . . -2.0(4) ?
    C2 C1 C6 C5 . . . . 0.5(4) ?
    C7 C1 C6 C5 . . . . 179.9(2) ?
    C2 C1 C7 O3 . . . . -65.7(3) ?
    C6 C1 C7 O3 . . . . 115.0(3) ?
    C2 C1 C7 N2 . . . . 115.6(3) ?
    C6 C1 C7 N2 . . . . -63.7(3) ?
    O3 C7 N2 C8 . . . . -1.1(4) ?
    C1 C7 N2 C8 . . . . 177.5(2) ?
    C7 N2 C8 C9 . . . . -122.8(3) ?
    N2 C8 C9 O4 . . . . 69.4(2) ?
    N2 C8 C9 C10 . . . . -51.3(3) ?
    C11 N3 C10 C9 . . . . 160.33(18) ?
    C19 N3 C10 C9 . . . . -77.0(2) ?
    O4 C9 C10 N3 . . . . -165.33(18) ?
    C8 C9 C10 N3 . . . . -45.4(3) ?
    C10 N3 C11 C20 . . . . -52.4(2) ?
    C19 N3 C11 C20 . . . . -176.07(18) ?
    C10 N3 C11 C12 . . . . -172.21(17) ?
    C19 N3 C11 C12 . . . . 64.2(2) ?
    N3 C11 C12 C13 . . . . -59.4(2) ?
    C20 C11 C12 C13 . . . . 178.98(19) ?
    C11 C12 C13 C14 . . . . 176.8(2) ?
    C11 C12 C13 C18 . . . . 51.5(3) ?
    C12 C13 C14 C15 . . . . -75.8(3) ?
    C18 C13 C14 C15 . . . . 49.0(3) ?
    C13 C14 C15 C16 . . . . -54.1(3) ?
    C14 C15 C16 C17 . . . . 57.2(3) ?
    C15 C16 C17 C18 . . . . -57.7(3) ?
    C16 C17 C18 C19 . . . . 178.8(2) ?
    C16 C17 C18 C13 . . . . 53.7(3) ?
    C12 C13 C18 C17 . . . . 77.4(3) ?
    C14 C13 C18 C17 . . . . -48.3(3) ?
    C12 C13 C18 C19 . . . . -48.5(3) ?
    C14 C13 C18 C19 . . . . -174.2(2) ?
    C11 N3 C19 C18 . . . . -64.1(3) ?
    C10 N3 C19 C18 . . . . 170.0(2) ?
    C17 C18 C19 N3 . . . . -70.8(3) ?
    C13 C18 C19 N3 . . . . 55.7(3) ?
    C21 N4 C20 O5 . . . . 4.6(4) ?
    C21 N4 C20 C11 . . . . -177.1(2) ?
    N3 C11 C20 O5 . . . . -41.3(3) ?
    C12 C11 C20 O5 . . . . 78.4(3) ?
    N3 C11 C20 N4 . . . . 140.4(2) ?
    C12 C11 C20 N4 . . . . -99.9(2) ?
    C20 N4 C21 C22 . . . . 64.5(3) ?
    C20 N4 C21 C23 . . . . -59.1(3) ?
    C20 N4 C21 C24 . . . . -177.5(2) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    O4 H4B O5 1_556 0.87(4) 1.94(4) 2.791(2) 169(3)
    N2 H2 O5 . 0.83(3) 2.11(3) 2.928(3) 169(3)
    N4 H4 O3 4_567 0.84(3) 2.15(3) 2.964(2) 161(3)
_shelxl_version_number     2014/6
data_II
_database_code_depnum_ccdc_archive 'CCDC 1432733'
_audit_creation_method     SHELXL-2014/6
_chemical_name_systematic
;\
(3S,4aS,8aS)-N-tert-Butyl-\
2-{(S)-2-[(S)-1-(2-chloro-4-nitrobenzoyl)pyrrolidin-2-yl]-\
2-hydroxyethyl}decahydroisoquinoline-3-carboxamide
;
_chemical_name_common     ?
_chemical_formula_moiety     'C27 H39 Cl N4 O5'
_chemical_formula_sum     'C27 H39 Cl N4 O5'
_chemical_formula_structural     ?
_chemical_formula_analytical     ?
_chemical_formula_iupac     'C27 H39 Cl N4 O5'
_chemical_formula_weight     535.07
_chemical_melting_point     ?
_symmetry_cell_setting     monoclinic
_symmetry_space_group_name_H-M     'P2(1)   '
_symmetry_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.
;
_space_group_crystal_system     monoclinic
_space_group_name_H-M_alt     'P 21'
_space_group_name_Hall     'P 2yb'
loop_
    _space_group_symop_operation_xyz
    'x, y, z'
    '-x, y+1/2, -z'
_cell_length_a     6.4341(7)
_cell_length_b     20.280(2)
_cell_length_c     11.0377(12)
_cell_angle_alpha     90
_cell_angle_beta     105.2480(10)
_cell_angle_gamma     90
_cell_volume     1389.5(3)
_cell_formula_units_Z     2
_cell_measurement_reflns_used     7806
_cell_measurement_theta_min     2.77
_cell_measurement_theta_max     26.27
_cell_measurement_temperature     168(2)
_exptl_crystal_description     'plates'
_exptl_crystal_colour     'colourless'
_exptl_crystal_size_max     0.864
_exptl_crystal_size_mid     0.654
_exptl_crystal_size_min     0.152
_exptl_crystal_density_diffrn     1.279
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     572
loop_
    _exptl_crystal_face_index_h
    _exptl_crystal_face_index_k
    _exptl_crystal_face_index_l
    _exptl_crystal_face_perp_dist
    1.00 0.00 0.00 0.3910
    -1.00 0.00 0.00 0.2620
    0.00 -1.00 0.00 0.3300
    0.00 1.00 0.00 0.1820
    0.00 0.00 1.00 0.0380
    0.00 0.00 -1.00 0.0760
    0.00 -1.00 -2.00 0.1560
    1.00 -3.00 -1.00 0.2890
    1.00 -3.00 -3.00 0.2160
    1.00 -5.00 0.00 0.2260
_exptl_absorpt_coefficient_mu     0.180
_exptl_absorpt_correction_type     integration
_exptl_absorpt_process_details
;
(SHELXTL/XPREP; Bruker, 2014)
;
_shelx_estimated_absorpt_T_min     0.860
_shelx_estimated_absorpt_T_max     0.973
_exptl_absorpt_correction_T_min     0.8920
_exptl_absorpt_correction_T_max     0.9802
_exptl_special_details
;
One distinct cell was identified using APEX2 (Bruker, 2014). Four frame
series were integrated and filtered for statistical outliers using
SAINT (Bruker, 2014) then corrected for absorption by integration using
SHELXTL/XPREP V2005/2 (Bruker, 2014) before using
SAINT/SADABS (Bruker, 2014) to sort, merge, and scale the
combined data. No decay correction was applied.
;
_diffrn_ambient_temperature     168(2)
_diffrn_radiation_type     'MoK\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'normal-focus sealed tube'
_diffrn_radiation_monochromator     'graphite'
_diffrn_measurement_device_type     ?
_diffrn_measurement_device     'Siemens Platform/APEXII CCD'
_diffrn_measurement_method     'profile data from φ and ω scans'
_diffrn_detector_area_resol_mean     ?
_diffrn_reflns_number     16374
_diffrn_reflns_av_R_equivalents     0.0243
_diffrn_reflns_theta_min     1.912
_diffrn_reflns_theta_max     26.363
_diffrn_reflns_theta_full     25.242
_diffrn_measured_fraction_theta_max     1.000
_diffrn_measured_fraction_theta_full     1.000
_diffrn_reflns_limit_h_min     -8
_diffrn_reflns_limit_h_max     8
_diffrn_reflns_limit_k_min     -25
_diffrn_reflns_limit_k_max     25
_diffrn_reflns_limit_l_min     -13
_diffrn_reflns_limit_l_max     13
_diffrn_standards_number     ?
_diffrn_standards_interval_time     ?
_diffrn_standards_decay_%     ?
_refine_special_details
;
Structure was phased by direct (Sheldrick, 2015) methods. Systematic conditions
suggested the ambiguous space group. The space group choice was confirmed by
successful convergence of the full-matrix least-squares refinement on
F². The final map had no significant features. A final analysis of
variance between observed and calculated structure factors showed little
dependence on amplitude and resolution.
;
_reflns_number_total     5627
_reflns_number_gt     5222
_reflns_threshold_expression     'I > 2σ(I)'
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0357
_refine_ls_R_factor_gt     0.0323
_refine_ls_wR_factor_gt     0.0799
_refine_ls_wR_factor_ref     0.0824
_refine_ls_goodness_of_fit_ref     1.039
_refine_ls_restrained_S_all     1.040
_refine_ls_number_reflns     5627
_refine_ls_number_parameters     377
_refine_ls_number_restraints     14
_refine_ls_hydrogen_treatment     mixed
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
              'w=1/[σ²(Fo²)+(0.0447P)²+0.1276P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary     ?
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.243
_refine_diff_density_min     -0.212
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     .
_refine_ls_abs_structure_details
;
Flack (1983); Hooft et al. (2008); 2720 Friedels
;
_refine_ls_abs_structure_Flack     0.036(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'
    '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'
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_cell_refinement
;
SAINT (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2014), XPREP (Bruker, 2014), and SADABS (Bruker,
2014)
;
_computing_structure_solution
;
SHELXS2014 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2015) and CrystalMaker (CrystalMaker, 1994)
;
_computing_publication_material
;
XCIF (Bruker, 2014) and publCIF (Westrip, 2010)
;
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    Cl Cl1 0.18218(12) 0.27617(3) 0.58986(6) 0.05313(19) Uani d 1 . .
    O O1 0.7185(5) 0.41190(18) 0.9393(3) 0.0657(8) Uani d 0.967(8) A 1
    O O2 0.5309(5) 0.48339(16) 1.0083(3) 0.0796(11) Uani d 0.967(8) A 1
    O O1B 0.658(13) 0.391(2) 0.970(8) 0.0657(8) Uani d 0.033(8) A 2
    O O2B 0.605(14) 0.4966(13) 0.961(9) 0.0796(11) Uani d 0.033(8) A 2
    N N1 0.5493(4) 0.43973(13) 0.9347(2) 0.0521(6) Uani d 1 . .
    O O3 -0.3816(17) 0.3687(9) 0.5659(16) 0.064(2) Uani d 0.58(2) . .
    C C7 -0.1974(15) 0.3696(13) 0.5438(6) 0.044(3) Uani d 0.58(2) B .
    O O3B -0.341(3) 0.3487(9) 0.584(2) 0.064(2) Uani d 0.42(2) B 2
    C C7B -0.209(2) 0.3832(18) 0.5437(8) 0.044(3) Uani d 0.42(2) B 2
    O O4 -0.0271(3) 0.50975(9) 0.45504(16) 0.0466(4) Uani d 1 . .
    H H4B -0.124(4) 0.5375(14) 0.441(3) 0.070 Uiso d 1 . .
    O O5 0.6776(3) 0.60681(10) 0.43924(17) 0.0497(5) Uani d 1 . .
    N N2 -0.1962(3) 0.38062(11) 0.4242(2) 0.0434(5) Uani d 1 . .
    N N3 0.1541(3) 0.56188(9) 0.25105(17) 0.0349(4) Uani d 1 . .
    N N4 0.3515(3) 0.61688(10) 0.48165(17) 0.0354(4) Uani d 1 . .
    H H4C 0.211(5) 0.6126(16) 0.452(3) 0.053 Uiso d 1 . .
    C C1 0.1816(4) 0.34965(12) 0.6715(2) 0.0407(6) Uani d 1 . .
    C C2 0.3653(5) 0.36560(13) 0.7648(2) 0.0419(5) Uani d 1 . .
    H H2A 0.4918 0.3393 0.7794 0.050 Uiso calc 1 . .
    C C3 0.3571(4) 0.42136(13) 0.8359(2) 0.0425(6) Uani d 1 . .
    C C4 0.1757(5) 0.46054(15) 0.8176(3) 0.0515(7) Uani d 1 . .
    H H4A 0.1728 0.4977 0.8697 0.062 Uiso calc 1 . .
    C C5 -0.0004(5) 0.44390(15) 0.7217(3) 0.0505(6) Uani d 1 . .
    H H5A -0.1264 0.4703 0.7071 0.061 Uiso calc 1 . .
    C C6 0.0008(4) 0.38941(13) 0.6450(2) 0.0417(6) Uani d 1 . .
    C C8 -0.0147(4) 0.40027(12) 0.3737(2) 0.0355(5) Uani d 1 . .
    H H8A 0.1254 0.3883 0.4342 0.043 Uiso calc 1 . .
    C C9 -0.0526(4) 0.35761(14) 0.2539(3) 0.0481(6) Uani d 1 . .
    H H9A -0.0348 0.3849 0.1829 0.058 Uiso calc 1 C 1
    H H9B 0.0544 0.3214 0.2674 0.058 Uiso calc 1 C 1
    C C10 -0.2747(10) 0.3296(4) 0.2237(6) 0.0504(15) Uani d 0.669(16) B 1
    H H10A -0.2719 0.2816 0.2401 0.060 Uiso calc 0.669(16) B 1
    H H10B -0.3527 0.3379 0.1350 0.060 Uiso calc 0.669(16) B 1
    C C11 -0.3755(11) 0.3670(4) 0.3125(7) 0.0423(15) Uani d 0.669(16) B 1
    H H11A -0.4415 0.4086 0.2737 0.051 Uiso calc 0.669(16) B 1
    H H11B -0.4878 0.3400 0.3353 0.051 Uiso calc 0.669(16) B 1
    C C10B -0.2980(17) 0.3525(8) 0.2257(15) 0.0504(15) Uani d 0.331(16) B 2
    H H10C -0.3618 0.3898 0.1705 0.060 Uiso calc 0.331(16) B 2
    H H10D -0.3439 0.3114 0.1777 0.060 Uiso calc 0.331(16) B 2
    C C11B -0.392(2) 0.3527(9) 0.3383(12) 0.0423(15) Uani d 0.331(16) B 2
    H H11C -0.5191 0.3818 0.3268 0.051 Uiso calc 0.331(16) B 2
    H H11D -0.4263 0.3079 0.3630 0.051 Uiso calc 0.331(16) B 2
    C C12 -0.0208(4) 0.47423(12) 0.3446(2) 0.0370(5) Uani d 1 . .
    H H12A -0.1522 0.4846 0.2757 0.044 Uiso calc 1 . .
    C C13 0.1800(4) 0.49527(12) 0.3056(2) 0.0380(5) Uani d 1 . .
    H H13A 0.3061 0.4945 0.3799 0.046 Uiso calc 1 . .
    H H13B 0.2073 0.4636 0.2433 0.046 Uiso calc 1 . .
    C C14 0.3607(3) 0.59631(12) 0.2673(2) 0.0357(5) Uani d 1 . .
    H H14A 0.4542 0.5706 0.2250 0.043 Uiso calc 1 . .
    C C15 0.3232(4) 0.66580(12) 0.2091(2) 0.0369(5) Uani d 1 . .
    H H15A 0.2424 0.6925 0.2564 0.044 Uiso calc 1 . .
    H H15B 0.4642 0.6874 0.2172 0.044 Uiso calc 1 . .
    C C16 0.1982(4) 0.66434(13) 0.0704(2) 0.0380(5) Uani d 1 . .
    H H16A 0.2901 0.6415 0.0230 0.046 Uiso calc 1 . .
    C C17 0.1487(4) 0.73367(15) 0.0150(2) 0.0462(6) Uani d 1 . .
    H H17A 0.2833 0.7598 0.0349 0.055 Uiso calc 1 . .
    H H17B 0.0968 0.7302 -0.0776 0.055 Uiso calc 1 . .
    C C18 -0.0196(4) 0.76982(15) 0.0644(2) 0.0470(6) Uani d 1 . .
    H H18A 0.0388 0.7786 0.1552 0.056 Uiso calc 1 . .
    H H18B -0.0528 0.8127 0.0209 0.056 Uiso calc 1 . .
    C C19 -0.2244(4) 0.72936(14) 0.0435(2) 0.0451(6) Uani d 1 . .
    H H19A -0.2910 0.7249 -0.0478 0.054 Uiso calc 1 . .
    H H19B -0.3279 0.7527 0.0807 0.054 Uiso calc 1 . .
    C C20 -0.1805(4) 0.66089(12) 0.1020(2) 0.0381(5) Uani d 1 . .
    H H20A -0.3159 0.6351 0.0816 0.046 Uiso calc 1 . .
    H H20B -0.1306 0.6652 0.1945 0.046 Uiso calc 1 . .
    C C21 -0.0090(4) 0.62377(13) 0.0539(2) 0.0374(5) Uani d 1 . .
    H H21A -0.0699 0.6159 -0.0380 0.045 Uiso calc 1 . .
    C C22 0.0428(4) 0.55715(13) 0.1167(2) 0.0396(5) Uani d 1 . .
    H H22A -0.0929 0.5322 0.1070 0.048 Uiso calc 1 . .
    H H22B 0.1344 0.5321 0.0736 0.048 Uiso calc 1 . .
    C C23 0.4782(3) 0.60558(11) 0.4055(2) 0.0359(5) Uani d 1 . .
    C C24 0.4216(4) 0.62935(12) 0.6177(2) 0.0390(5) Uani d 1 . .
    C C25 0.2182(7) 0.6384(4) 0.6614(5) 0.0498(13) Uani d 0.811(17) D 1
    H H25A 0.1300 0.5984 0.6430 0.075 Uiso calc 0.811(17) D 1
    H H25B 0.1361 0.6760 0.6173 0.075 Uiso calc 0.811(17) D 1
    H H25C 0.2573 0.6467 0.7521 0.075 Uiso calc 0.811(17) D 1
    C C26 0.5534(13) 0.5704(3) 0.6839(4) 0.0572(14) Uani d 0.811(17) D 1
    H H26A 0.4678 0.5300 0.6631 0.086 Uiso calc 0.811(17) D 1
    H H26B 0.5913 0.5773 0.7750 0.086 Uiso calc 0.811(17) D 1
    H H26C 0.6853 0.5662 0.6559 0.086 Uiso calc 0.811(17) D 1
    C C27 0.5599(11) 0.6921(3) 0.6388(7) 0.0569(15) Uani d 0.811(17) D 1
    H H27A 0.4787 0.7283 0.5894 0.085 Uiso calc 0.811(17) D 1
    H H27B 0.6918 0.6842 0.6124 0.085 Uiso calc 0.811(17) D 1
    H H27C 0.5977 0.7037 0.7281 0.085 Uiso calc 0.811(17) D 1
    C C25B 0.227(4) 0.6608(14) 0.651(3) 0.0498(13) Uani d 0.189(17) D 2
    H H25D 0.0945 0.6390 0.6040 0.075 Uiso calc 0.189(17) D 2
    H H25E 0.2201 0.7078 0.6299 0.075 Uiso calc 0.189(17) D 2
    H H25F 0.2418 0.6558 0.7415 0.075 Uiso calc 0.189(17) D 2
    C C26B 0.461(5) 0.5602(8) 0.678(2) 0.0572(14) Uani d 0.189(17) D 2
    H H26D 0.3258 0.5351 0.6569 0.086 Uiso calc 0.189(17) D 2
    H H26E 0.5122 0.5647 0.7697 0.086 Uiso calc 0.189(17) D 2
    H H26F 0.5692 0.5369 0.6465 0.086 Uiso calc 0.189(17) D 2
    C C27B 0.612(4) 0.6761(14) 0.659(3) 0.0569(15) Uani d 0.189(17) D 2
    H H27D 0.7446 0.6534 0.6543 0.085 Uiso calc 0.189(17) D 2
    H H27E 0.6262 0.6903 0.7457 0.085 Uiso calc 0.189(17) D 2
    H H27F 0.5895 0.7148 0.6037 0.085 Uiso calc 0.189(17) D 2
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    Cl1 C1 . 1.742(2) ?
    O1 N1 . 1.215(3) ?
    O2 N1 . 1.228(3) ?
    O1B N1 . 1.210(15) ?
    O2B N1 . 1.219(15) ?
    N1 C3 . 1.466(3) ?
    O3 C7B . 1.236(18) ?
    O3 C7 . 1.271(11) ?
    C7 O3B . 1.20(2) ?
    C7 N2 . 1.341(7) ?
    C7 C6 . 1.512(7) ?
    O3B C7B . 1.271(14) ?
    C7B N2 . 1.343(10) ?
    C7B C6 . 1.513(10) ?
    O4 C12 . 1.425(3) ?
    O4 H4B . 0.824(14) ?
    O5 C23 . 1.239(3) ?
    N2 C8 . 1.475(3) ?
    N2 C11 . 1.476(5) ?
    N2 C11B . 1.477(10) ?
    N3 C22 . 1.470(3) ?
    N3 C14 . 1.470(3) ?
    N3 C13 . 1.471(3) ?
    N4 C23 . 1.336(3) ?
    N4 C24 . 1.472(3) ?
    N4 H4C . 0.88(3) ?
    C1 C6 . 1.382(4) ?
    C1 C2 . 1.387(4) ?
    C2 C3 . 1.385(4) ?
    C2 H2A . 0.9500 ?
    C3 C4 . 1.382(4) ?
    C4 C5 . 1.374(4) ?
    C4 H4A . 0.9500 ?
    C5 C6 . 1.393(4) ?
    C5 H5A . 0.9500 ?
    C8 C12 . 1.532(3) ?
    C8 C9 . 1.545(3) ?
    C8 H8A . 1.0000 ?
    C9 C10 . 1.492(6) ?
    C9 C10B . 1.531(11) ?
    C9 H9A . 0.9900 ?
    C9 H9B . 0.9900 ?
    C10 C11 . 1.514(7) ?
    C10 H10A . 0.9900 ?
    C10 H10B . 0.9900 ?
    C11 H11A . 0.9900 ?
    C11 H11B . 0.9900 ?
    C10B C11B . 1.519(11) ?
    C10B H10C . 0.9900 ?
    C10B H10D . 0.9900 ?
    C11B H11C . 0.9900 ?
    C11B H11D . 0.9900 ?
    C12 C13 . 1.526(3) ?
    C12 H12A . 1.0000 ?
    C13 H13A . 0.9900 ?
    C13 H13B . 0.9900 ?
    C14 C23 . 1.525(3) ?
    C14 C15 . 1.541(3) ?
    C14 H14A . 1.0000 ?
    C15 C16 . 1.531(3) ?
    C15 H15A . 0.9900 ?
    C15 H15B . 0.9900 ?
    C16 C17 . 1.533(4) ?
    C16 C21 . 1.536(3) ?
    C16 H16A . 1.0000 ?
    C17 C18 . 1.522(4) ?
    C17 H17A . 0.9900 ?
    C17 H17B . 0.9900 ?
    C18 C19 . 1.518(4) ?
    C18 H18A . 0.9900 ?
    C18 H18B . 0.9900 ?
    C19 C20 . 1.526(4) ?
    C19 H19A . 0.9900 ?
    C19 H19B . 0.9900 ?
    C20 C21 . 1.541(3) ?
    C20 H20A . 0.9900 ?
    C20 H20B . 0.9900 ?
    C21 C22 . 1.515(4) ?
    C21 H21A . 1.0000 ?
    C22 H22A . 0.9900 ?
    C22 H22B . 0.9900 ?
    C24 C25 . 1.520(4) ?
    C24 C27B . 1.524(13) ?
    C24 C27 . 1.535(5) ?
    C24 C26 . 1.535(4) ?
    C24 C25B . 1.536(13) ?
    C24 C26B . 1.545(12) ?
    C25 H25A . 0.9800 ?
    C25 H25B . 0.9800 ?
    C25 H25C . 0.9800 ?
    C26 H26A . 0.9800 ?
    C26 H26B . 0.9800 ?
    C26 H26C . 0.9800 ?
    C27 H27A . 0.9800 ?
    C27 H27B . 0.9800 ?
    C27 H27C . 0.9800 ?
    C25B H25D . 0.9800 ?
    C25B H25E . 0.9800 ?
    C25B H25F . 0.9800 ?
    C26B H26D . 0.9800 ?
    C26B H26E . 0.9800 ?
    C26B H26F . 0.9800 ?
    C27B H27D . 0.9800 ?
    C27B H27E . 0.9800 ?
    C27B H27F . 0.9800 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    O1B N1 O2B . . 126(3) ?
    O1 N1 O2 . . 123.3(3) ?
    O1B N1 C3 . . 110(3) ?
    O1 N1 C3 . . 119.0(2) ?
    O2B N1 C3 . . 124(3) ?
    O2 N1 C3 . . 117.8(3) ?
    C7B O3 C7 . . 13(3) ?
    O3B C7 O3 . . 22.9(9) ?
    O3B C7 N2 . . 128.8(12) ?
    O3 C7 N2 . . 116.0(12) ?
    O3B C7 C6 . . 113.6(12) ?
    O3 C7 C6 . . 120.7(10) ?
    N2 C7 C6 . . 117.5(7) ?
    C7 O3B C7B . . 13(3) ?
    O3 C7B O3B . . 22.8(9) ?
    O3 C7B N2 . . 118.4(11) ?
    O3B C7B N2 . . 122.9(19) ?
    O3 C7B C6 . . 123.1(11) ?
    O3B C7B C6 . . 109.5(15) ?
    N2 C7B C6 . . 117.2(9) ?
    C12 O4 H4B . . 112(2) ?
    C7 N2 C7B . . 12(3) ?
    C7 N2 C8 . . 128.8(4) ?
    C7B N2 C8 . . 128.2(5) ?
    C7 N2 C11 . . 125.8(5) ?
    C8 N2 C11 . . 105.0(4) ?
    C7 N2 C11B . . 110.1(7) ?
    C7B N2 C11B . . 112.6(8) ?
    C8 N2 C11B . . 119.2(6) ?
    C22 N3 C14 . . 109.84(18) ?
    C22 N3 C13 . . 109.01(18) ?
    C14 N3 C13 . . 112.62(18) ?
    C23 N4 C24 . . 126.7(2) ?
    C23 N4 H4C . . 118.8(19) ?
    C24 N4 H4C . . 114.2(19) ?
    C6 C1 C2 . . 121.8(2) ?
    C6 C1 Cl1 . . 120.4(2) ?
    C2 C1 Cl1 . . 117.8(2) ?
    C3 C2 C1 . . 117.3(2) ?
    C3 C2 H2A . . 121.3 ?
    C1 C2 H2A . . 121.3 ?
    C4 C3 C2 . . 122.9(2) ?
    C4 C3 N1 . . 118.5(2) ?
    C2 C3 N1 . . 118.6(2) ?
    C5 C4 C3 . . 117.7(2) ?
    C5 C4 H4A . . 121.2 ?
    C3 C4 H4A . . 121.2 ?
    C4 C5 C6 . . 121.9(3) ?
    C4 C5 H5A . . 119.1 ?
    C6 C5 H5A . . 119.1 ?
    C1 C6 C5 . . 118.2(2) ?
    C1 C6 C7 . . 120.0(10) ?
    C5 C6 C7 . . 121.4(9) ?
    C1 C6 C7B . . 130.1(13) ?
    C5 C6 C7B . . 111.7(13) ?
    C7 C6 C7B . . 11(2) ?
    N2 C8 C12 . . 111.36(19) ?
    N2 C8 C9 . . 102.10(19) ?
    C12 C8 C9 . . 112.3(2) ?
    N2 C8 H8A . . 110.3 ?
    C12 C8 H8A . . 110.3 ?
    C9 C8 H8A . . 110.3 ?
    C10 C9 C8 . . 109.3(3) ?
    C10B C9 C8 . . 97.7(6) ?
    C10 C9 H9A . . 109.8 ?
    C8 C9 H9A . . 109.8 ?
    C10 C9 H9B . . 109.8 ?
    C8 C9 H9B . . 109.8 ?
    H9A C9 H9B . . 108.3 ?
    C9 C10 C11 . . 102.3(6) ?
    C9 C10 H10A . . 111.3 ?
    C11 C10 H10A . . 111.3 ?
    C9 C10 H10B . . 111.3 ?
    C11 C10 H10B . . 111.3 ?
    H10A C10 H10B . . 109.2 ?
    N2 C11 C10 . . 105.1(5) ?
    N2 C11 H11A . . 110.7 ?
    C10 C11 H11A . . 110.7 ?
    N2 C11 H11B . . 110.7 ?
    C10 C11 H11B . . 110.7 ?
    H11A C11 H11B . . 108.8 ?
    C11B C10B C9 . . 116.4(11) ?
    C11B C10B H10C . . 108.2 ?
    C9 C10B H10C . . 108.2 ?
    C11B C10B H10D . . 108.2 ?
    C9 C10B H10D . . 108.2 ?
    H10C C10B H10D . . 107.3 ?
    N2 C11B C10B . . 94.0(9) ?
    N2 C11B H11C . . 112.9 ?
    C10B C11B H11C . . 112.9 ?
    N2 C11B H11D . . 112.9 ?
    C10B C11B H11D . . 112.9 ?
    H11C C11B H11D . . 110.3 ?
    O4 C12 C13 . . 108.45(19) ?
    O4 C12 C8 . . 108.7(2) ?
    C13 C12 C8 . . 110.82(18) ?
    O4 C12 H12A . . 109.6 ?
    C13 C12 H12A . . 109.6 ?
    C8 C12 H12A . . 109.6 ?
    N3 C13 C12 . . 111.04(18) ?
    N3 C13 H13A . . 109.4 ?
    C12 C13 H13A . . 109.4 ?
    N3 C13 H13B . . 109.4 ?
    C12 C13 H13B . . 109.4 ?
    H13A C13 H13B . . 108.0 ?
    N3 C14 C23 . . 112.03(19) ?
    N3 C14 C15 . . 110.24(17) ?
    C23 C14 C15 . . 106.64(18) ?
    N3 C14 H14A . . 109.3 ?
    C23 C14 H14A . . 109.3 ?
    C15 C14 H14A . . 109.3 ?
    C16 C15 C14 . . 112.51(19) ?
    C16 C15 H15A . . 109.1 ?
    C14 C15 H15A . . 109.1 ?
    C16 C15 H15B . . 109.1 ?
    C14 C15 H15B . . 109.1 ?
    H15A C15 H15B . . 107.8 ?
    C15 C16 C17 . . 112.4(2) ?
    C15 C16 C21 . . 109.89(19) ?
    C17 C16 C21 . . 111.2(2) ?
    C15 C16 H16A . . 107.7 ?
    C17 C16 H16A . . 107.7 ?
    C21 C16 H16A . . 107.7 ?
    C18 C17 C16 . . 113.0(2) ?
    C18 C17 H17A . . 109.0 ?
    C16 C17 H17A . . 109.0 ?
    C18 C17 H17B . . 109.0 ?
    C16 C17 H17B . . 109.0 ?
    H17A C17 H17B . . 107.8 ?
    C19 C18 C17 . . 110.9(2) ?
    C19 C18 H18A . . 109.5 ?
    C17 C18 H18A . . 109.5 ?
    C19 C18 H18B . . 109.5 ?
    C17 C18 H18B . . 109.5 ?
    H18A C18 H18B . . 108.1 ?
    C18 C19 C20 . . 111.8(2) ?
    C18 C19 H19A . . 109.3 ?
    C20 C19 H19A . . 109.3 ?
    C18 C19 H19B . . 109.3 ?
    C20 C19 H19B . . 109.3 ?
    H19A C19 H19B . . 107.9 ?
    C19 C20 C21 . . 111.6(2) ?
    C19 C20 H20A . . 109.3 ?
    C21 C20 H20A . . 109.3 ?
    C19 C20 H20B . . 109.3 ?
    C21 C20 H20B . . 109.3 ?
    H20A C20 H20B . . 108.0 ?
    C22 C21 C16 . . 110.13(19) ?
    C22 C21 C20 . . 111.7(2) ?
    C16 C21 C20 . . 112.0(2) ?
    C22 C21 H21A . . 107.6 ?
    C16 C21 H21A . . 107.6 ?
    C20 C21 H21A . . 107.6 ?
    N3 C22 C21 . . 113.16(18) ?
    N3 C22 H22A . . 108.9 ?
    C21 C22 H22A . . 108.9 ?
    N3 C22 H22B . . 108.9 ?
    C21 C22 H22B . . 108.9 ?
    H22A C22 H22B . . 107.8 ?
    O5 C23 N4 . . 124.3(2) ?
    O5 C23 C14 . . 120.3(2) ?
    N4 C23 C14 . . 115.23(18) ?
    N4 C24 C25 . . 106.6(3) ?
    N4 C24 C27B . . 114.8(14) ?
    N4 C24 C27 . . 107.9(3) ?
    C25 C24 C27 . . 111.4(4) ?
    N4 C24 C26 . . 109.6(3) ?
    C25 C24 C26 . . 110.9(3) ?
    C27 C24 C26 . . 110.3(3) ?
    N4 C24 C25B . . 105.5(12) ?
    C27B C24 C25B . . 108.3(18) ?
    N4 C24 C26B . . 104.9(9) ?
    C27B C24 C26B . . 114.1(13) ?
    C25B C24 C26B . . 108.9(13) ?
    C24 C25 H25A . . 109.5 ?
    C24 C25 H25B . . 109.5 ?
    H25A C25 H25B . . 109.5 ?
    C24 C25 H25C . . 109.5 ?
    H25A C25 H25C . . 109.5 ?
    H25B C25 H25C . . 109.5 ?
    C24 C26 H26A . . 109.5 ?
    C24 C26 H26B . . 109.5 ?
    H26A C26 H26B . . 109.5 ?
    C24 C26 H26C . . 109.5 ?
    H26A C26 H26C . . 109.5 ?
    H26B C26 H26C . . 109.5 ?
    C24 C27 H27A . . 109.5 ?
    C24 C27 H27B . . 109.5 ?
    H27A C27 H27B . . 109.5 ?
    C24 C27 H27C . . 109.5 ?
    H27A C27 H27C . . 109.5 ?
    H27B C27 H27C . . 109.5 ?
    C24 C25B H25D . . 109.5 ?
    C24 C25B H25E . . 109.5 ?
    H25D C25B H25E . . 109.5 ?
    C24 C25B H25F . . 109.5 ?
    H25D C25B H25F . . 109.5 ?
    H25E C25B H25F . . 109.5 ?
    C24 C26B H26D . . 109.5 ?
    C24 C26B H26E . . 109.5 ?
    H26D C26B H26E . . 109.5 ?
    C24 C26B H26F . . 109.5 ?
    H26D C26B H26F . . 109.5 ?
    H26E C26B H26F . . 109.5 ?
    C24 C27B H27D . . 109.5 ?
    C24 C27B H27E . . 109.5 ?
    H27D C27B H27E . . 109.5 ?
    C24 C27B H27F . . 109.5 ?
    H27D C27B H27F . . 109.5 ?
    H27E C27B H27F . . 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_site_symmetry_1
    _geom_torsion_site_symmetry_2
    _geom_torsion_site_symmetry_3
    _geom_torsion_site_symmetry_4
    _geom_torsion
    _geom_torsion_publ_flag
    C7B O3 C7 O3B . . . . 154(6) ?
    C7B O3 C7 N2 . . . . -77(3) ?
    C7B O3 C7 C6 . . . . 76(3) ?
    O3 C7 O3B C7B . . . . -26(5) ?
    N2 C7 O3B C7B . . . . -88(4) ?
    C6 C7 O3B C7B . . . . 88(3) ?
    C7 O3 C7B O3B . . . . -25(5) ?
    C7 O3 C7B N2 . . . . 83(4) ?
    C7 O3 C7B C6 . . . . -84(4) ?
    C7 O3B C7B O3 . . . . 153(6) ?
    C7 O3B C7B N2 . . . . 68(4) ?
    C7 O3B C7B C6 . . . . -76(3) ?
    O3B C7 N2 C7B . . . . 95(4) ?
    O3 C7 N2 C7B . . . . 72(4) ?
    C6 C7 N2 C7B . . . . -81(4) ?
    O3B C7 N2 C8 . . . . -174(2) ?
    O3 C7 N2 C8 . . . . 163.8(14) ?
    C6 C7 N2 C8 . . . . 11(3) ?
    O3 C7 N2 C11 . . . . -25(3) ?
    C6 C7 N2 C11 . . . . -177.9(10) ?
    O3B C7 N2 C11B . . . . -10(4) ?
    O3 C7 N2 C11B . . . . -32(3) ?
    C6 C7 N2 C11B . . . . 174.6(15) ?
    O3 C7B N2 C7 . . . . -87(5) ?
    O3B C7B N2 C7 . . . . -61(4) ?
    C6 C7B N2 C7 . . . . 80(4) ?
    O3 C7B N2 C8 . . . . 174.9(19) ?
    O3B C7B N2 C8 . . . . -159.1(18) ?
    C6 C7B N2 C8 . . . . -18(4) ?
    O3 C7B N2 C11B . . . . -7(4) ?
    O3B C7B N2 C11B . . . . 19(4) ?
    C6 C7B N2 C11B . . . . 161(2) ?
    C6 C1 C2 C3 . . . . 3.5(3) ?
    Cl1 C1 C2 C3 . . . . -174.92(18) ?
    C1 C2 C3 C4 . . . . 0.3(4) ?
    C1 C2 C3 N1 . . . . -179.6(2) ?
    O1B N1 C3 C4 . . . . 155(6) ?
    O1 N1 C3 C4 . . . . -168.9(3) ?
    O2B N1 C3 C4 . . . . -36(7) ?
    O2 N1 C3 C4 . . . . 10.2(4) ?
    O1B N1 C3 C2 . . . . -26(6) ?
    O1 N1 C3 C2 . . . . 10.9(4) ?
    O2B N1 C3 C2 . . . . 144(7) ?
    O2 N1 C3 C2 . . . . -169.9(3) ?
    C2 C3 C4 C5 . . . . -2.2(4) ?
    N1 C3 C4 C5 . . . . 177.7(2) ?
    C3 C4 C5 C6 . . . . 0.4(4) ?
    C2 C1 C6 C5 . . . . -5.2(4) ?
    Cl1 C1 C6 C5 . . . . 173.2(2) ?
    C2 C1 C6 C7 . . . . -179.1(6) ?
    Cl1 C1 C6 C7 . . . . -0.7(6) ?
    C2 C1 C6 C7B . . . . 176.1(9) ?
    Cl1 C1 C6 C7B . . . . -5.5(10) ?
    C4 C5 C6 C1 . . . . 3.2(4) ?
    C4 C5 C6 C7 . . . . 177.0(7) ?
    C4 C5 C6 C7B . . . . -177.9(8) ?
    O3B C7 C6 C1 . . . . 105(2) ?
    O3 C7 C6 C1 . . . . 129(2) ?
    N2 C7 C6 C1 . . . . -79(2) ?
    O3B C7 C6 C5 . . . . -69(3) ?
    O3 C7 C6 C5 . . . . -44(3) ?
    N2 C7 C6 C5 . . . . 107.5(16) ?
    O3B C7 C6 C7B . . . . -95(4) ?
    O3 C7 C6 C7B . . . . -71(4) ?
    N2 C7 C6 C7B . . . . 81(4) ?
    O3 C7B C6 C1 . . . . 110(3) ?
    O3B C7B C6 C1 . . . . 90(2) ?
    N2 C7B C6 C1 . . . . -57(3) ?
    O3 C7B C6 C5 . . . . -69(3) ?
    O3B C7B C6 C5 . . . . -89(3) ?
    N2 C7B C6 C5 . . . . 125(2) ?
    O3 C7B C6 C7 . . . . 87(5) ?
    O3B C7B C6 C7 . . . . 67(4) ?
    N2 C7B C6 C7 . . . . -80(4) ?
    C7 N2 C8 C12 . . . . -100.6(15) ?
    C7B N2 C8 C12 . . . . -85(2) ?
    C11 N2 C8 C12 . . . . 86.4(4) ?
    C11B N2 C8 C12 . . . . 96.6(9) ?
    C7 N2 C8 C9 . . . . 139.3(15) ?
    C7B N2 C8 C9 . . . . 155(2) ?
    C11 N2 C8 C9 . . . . -33.6(4) ?
    C11B N2 C8 C9 . . . . -23.5(9) ?
    N2 C8 C9 C10 . . . . 14.1(5) ?
    C12 C8 C9 C10 . . . . -105.3(4) ?
    N2 C8 C9 C10B . . . . 29.1(7) ?
    C12 C8 C9 C10B . . . . -90.3(7) ?
    C8 C9 C10 C11 . . . . 10.2(8) ?
    C7 N2 C11 C10 . . . . -131.3(15) ?
    C8 N2 C11 C10 . . . . 42.0(7) ?
    C9 C10 C11 N2 . . . . -31.3(9) ?
    C8 C9 C10B C11B . . . . -31.8(15) ?
    C7 N2 C11B C10B . . . . -161.4(15) ?
    C7B N2 C11B C10B . . . . -174(2) ?
    C8 N2 C11B C10B . . . . 4.3(16) ?
    C9 C10B C11B N2 . . . . 18.3(18) ?
    N2 C8 C12 O4 . . . . 55.0(2) ?
    C9 C8 C12 O4 . . . . 168.76(19) ?
    N2 C8 C12 C13 . . . . 174.05(19) ?
    C9 C8 C12 C13 . . . . -72.1(2) ?
    C22 N3 C13 C12 . . . . -85.1(2) ?
    C14 N3 C13 C12 . . . . 152.70(18) ?
    O4 C12 C13 N3 . . . . -73.4(2) ?
    C8 C12 C13 N3 . . . . 167.38(18) ?
    C22 N3 C14 C23 . . . . 177.20(18) ?
    C13 N3 C14 C23 . . . . -61.1(2) ?
    C22 N3 C14 C15 . . . . 58.6(2) ?
    C13 N3 C14 C15 . . . . -179.68(18) ?
    N3 C14 C15 C16 . . . . -56.0(2) ?
    C23 C14 C15 C16 . . . . -177.86(18) ?
    C14 C15 C16 C17 . . . . 176.37(19) ?
    C14 C15 C16 C21 . . . . 52.0(2) ?
    C15 C16 C17 C18 . . . . -70.8(3) ?
    C21 C16 C17 C18 . . . . 52.9(3) ?
    C16 C17 C18 C19 . . . . -55.0(3) ?
    C17 C18 C19 C20 . . . . 55.7(3) ?
    C18 C19 C20 C21 . . . . -55.3(3) ?
    C15 C16 C21 C22 . . . . -51.3(2) ?
    C17 C16 C21 C22 . . . . -176.4(2) ?
    C15 C16 C21 C20 . . . . 73.6(2) ?
    C17 C16 C21 C20 . . . . -51.5(3) ?
    C19 C20 C21 C22 . . . . 177.21(19) ?
    C19 C20 C21 C16 . . . . 53.1(3) ?
    C14 N3 C22 C21 . . . . -61.1(2) ?
    C13 N3 C22 C21 . . . . 175.09(19) ?
    C16 C21 C22 N3 . . . . 57.2(2) ?
    C20 C21 C22 N3 . . . . -67.9(2) ?
    C24 N4 C23 O5 . . . . -3.2(4) ?
    C24 N4 C23 C14 . . . . -178.2(2) ?
    N3 C14 C23 O5 . . . . 149.4(2) ?
    C15 C14 C23 O5 . . . . -89.9(2) ?
    N3 C14 C23 N4 . . . . -35.4(3) ?
    C15 C14 C23 N4 . . . . 85.3(2) ?
    C23 N4 C24 C25 . . . . -179.4(4) ?
    C23 N4 C24 C27B . . . . 43.0(15) ?
    C23 N4 C24 C27 . . . . 60.9(4) ?
    C23 N4 C24 C26 . . . . -59.3(5) ?
    C23 N4 C24 C25B . . . . 162.1(12) ?
    C23 N4 C24 C26B . . . . -83.0(13) ?
loop_
    _geom_hbond_atom_site_label_D
    _geom_hbond_atom_site_label_H
    _geom_hbond_atom_site_label_A
    _geom_hbond_site_symmetry_A
    _geom_hbond_distance_DH
    _geom_hbond_distance_HA
    _geom_hbond_distance_DA
    _geom_hbond_angle_DHA
    N4 H4C O4 . 0.88(3) 2.60(3) 3.219(3) 129(3)
    O4 H4B O5 1_455 0.824(14) 1.894(16) 2.709(2) 170(4)
_shelxl_version_number     2014/6
