#------------------------------------------------------------------------------
#$Date: 2024-04-05 01:33:35 +0300 (Fri, 05 Apr 2024) $
#$Revision: 290821 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/27/7132710.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7132710
loop_
_publ_author_name
'Koch, Katelyn N.'
'Teo, Aaron J.'
'Wheeler, Kraig A.'
_publ_section_title
;
 Dual space divergence in small molecule quasiracemates: benzoyl leucine
 and phenylalanine assemblies.
;
_journal_issue                   20
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2800
_journal_page_last               2803
_journal_paper_doi               10.1039/d3cc06212k
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration rmad
_chemical_formula_moiety         'C17 H17 N O3, C13 H16 Cl N O3'
_chemical_formula_sum            'C30 H33 Cl N2 O6'
_chemical_formula_weight         553.03
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-01-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_audit_update_record
;
2024-01-24 deposited with the CCDC.	2024-02-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.2860(10)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   10.7094(3)
_cell_length_b                   9.8205(3)
_cell_length_c                   14.5002(4)
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.03
_cell_measurement_theta_min      3.27
_cell_volume                     1420.97(7)
_computing_cell_refinement       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0303
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            31726
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.206
_diffrn_reflns_theta_min         3.271
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_exptl_absorpt_coefficient_mu    1.566
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6335
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Needle
_exptl_crystal_F_000             584
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: MeOH'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.188
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 2342 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(5)
_refine_ls_extinction_coef       0.0011(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     368
_refine_ls_number_reflns         5553
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0305
_refine_ls_R_factor_gt           0.0282
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0339P)²+0.2969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0693
_refine_ls_wR_factor_ref         0.0706
_reflns_Friedel_coverage         0.877
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                5264
_reflns_number_total             5553
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc06212k2.cif
_cod_data_source_block           21kaw34_a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7132699--7132715.cif.
;
_cod_database_code               7132710
_shelx_shelxl_version_number     2019/1
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C9A(H9A), C9B(H9B), C11B(H11B)
2.b Secondary CH2 refined with riding coordinates:
 C10A(H10A,H10B), C10B(H10C,H10D)
2.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C6A(H6A), C7A(H7A), C12A(H12A), C13A(H13A), C14A(H14A),
 C15A(H15A), C16A(H16A), C3B(H3B), C4B(H4B), C6B(H6B), C7B(H7B)
2.d Idealised Me refined as rotating group:
 C17A(H17A,H17B,H17C), C12B(H12B,H12C,H12D), C13B(H13B,H13C,H13D)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
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
O1A O 0.40364(15) 0.22409(16) 0.92280(11) 0.0178(3) Uani 1 1 d . . . . .
O2A O 0.59438(15) 0.54602(18) 0.94257(11) 0.0225(4) Uani 1 1 d . . . . .
H2A H 0.593(3) 0.601(4) 0.986(2) 0.034 Uiso 1 1 d . U . . .
O3A O 0.37081(14) 0.54336(15) 0.89758(10) 0.0179(3) Uani 1 1 d . . . . .
N1A N 0.35308(19) 0.32380(19) 0.77426(14) 0.0157(4) Uani 1 1 d . . . . .
H1A H 0.290(3) 0.345(3) 0.720(2) 0.019 Uiso 1 1 d . U . . .
C1A C 0.3246(2) 0.2380(2) 0.83601(15) 0.0143(4) Uani 1 1 d . . . . .
C2A C 0.1954(2) 0.1621(2) 0.79455(15) 0.0157(4) Uani 1 1 d . . . . .
C3A C 0.1370(2) 0.1109(2) 0.85879(16) 0.0180(4) Uani 1 1 d . . . . .
H3A H 0.178528 0.126642 0.927907 0.022 Uiso 1 1 calc R U . . .
C4A C 0.0185(2) 0.0369(2) 0.82285(16) 0.0208(5) Uani 1 1 d . . . . .
H4A H -0.020610 0.003163 0.867574 0.025 Uiso 1 1 calc R U . . .
C5A C -0.0439(2) 0.0116(2) 0.72143(17) 0.0191(5) Uani 1 1 d . . . . .
C6A C 0.0126(2) 0.0665(3) 0.65769(15) 0.0195(4) Uani 1 1 d . . . . .
H6A H -0.030752 0.053314 0.588421 0.023 Uiso 1 1 calc R U . . .
C7A C 0.1310(2) 0.1402(2) 0.69267(16) 0.0172(4) Uani 1 1 d . . . . .
H7A H 0.168588 0.175797 0.647584 0.021 Uiso 1 1 calc R U . . .
C8A C 0.4725(2) 0.5047(2) 0.88723(15) 0.0155(4) Uani 1 1 d . . . . .
C9A C 0.4753(2) 0.4039(2) 0.80817(15) 0.0157(4) Uani 1 1 d . . . . .
H9A H 0.553408 0.341348 0.837322 0.019 Uiso 1 1 calc R U . . .
C10A C 0.4903(2) 0.4796(2) 0.71938(16) 0.0184(4) Uani 1 1 d . . . . .
H10A H 0.407708 0.532386 0.684951 0.022 Uiso 1 1 calc R U . . .
H10B H 0.565747 0.544760 0.744102 0.022 Uiso 1 1 calc R U . . .
C11A C 0.5155(2) 0.3834(2) 0.64635(15) 0.0178(4) Uani 1 1 d . . . . .
C12A C 0.4114(2) 0.3261(2) 0.56767(16) 0.0211(5) Uani 1 1 d . . . . .
H12A H 0.321283 0.349437 0.557593 0.025 Uiso 1 1 calc R U . . .
C13A C 0.4378(3) 0.2351(3) 0.50380(17) 0.0252(5) Uani 1 1 d . . . . .
H13A H 0.365810 0.196061 0.450774 0.030 Uiso 1 1 calc R U . . .
C14A C 0.5686(3) 0.2009(3) 0.51694(17) 0.0253(5) Uani 1 1 d . . . . .
H14A H 0.586234 0.137832 0.473531 0.030 Uiso 1 1 calc R U . . .
C15A C 0.6738(3) 0.2592(3) 0.59375(19) 0.0256(5) Uani 1 1 d . . . . .
H15A H 0.763827 0.237575 0.602399 0.031 Uiso 1 1 calc R U . . .
C16A C 0.6466(2) 0.3494(3) 0.65794(17) 0.0231(5) Uani 1 1 d . . . . .
H16A H 0.718830 0.388616 0.710723 0.028 Uiso 1 1 calc R U . . .
C17A C -0.1689(2) -0.0748(3) 0.68141(19) 0.0255(5) Uani 1 1 d . . . . .
H17A H -0.247742 -0.015627 0.656144 0.038 Uiso 1 1 calc R U . . .
H17B H -0.176055 -0.132381 0.734478 0.038 Uiso 1 1 calc R U . . .
H17C H -0.163930 -0.132444 0.627678 0.038 Uiso 1 1 calc R U . . .
Cl1B Cl 0.68541(5) 1.07483(6) 0.85044(4) 0.02737(15) Uani 1 1 d . . . . .
O1B O 0.09683(16) 0.77207(17) 0.58789(11) 0.0206(3) Uani 1 1 d . . . . .
O2B O -0.08651(15) 0.45455(18) 0.54431(11) 0.0214(3) Uani 1 1 d . . . . .
H2B H -0.085(3) 0.395(4) 0.501(2) 0.032 Uiso 1 1 d . U . . .
O3B O 0.13809(15) 0.44391(16) 0.59809(10) 0.0193(3) Uani 1 1 d . . . . .
N1B N 0.15130(19) 0.65642(19) 0.73026(13) 0.0161(4) Uani 1 1 d . . . . .
H1B H 0.212(3) 0.626(3) 0.781(2) 0.019 Uiso 1 1 d . U . . .
C1B C 0.1771(2) 0.7526(2) 0.67421(16) 0.0168(4) Uani 1 1 d . . . . .
C2B C 0.3033(2) 0.8328(2) 0.71959(16) 0.0164(4) Uani 1 1 d . . . . .
C3B C 0.3566(2) 0.9011(2) 0.65814(16) 0.0201(5) Uani 1 1 d . . . . .
H3B H 0.312207 0.895979 0.588383 0.024 Uiso 1 1 calc R U . . .
C4B C 0.4737(2) 0.9764(3) 0.69736(17) 0.0213(5) Uani 1 1 d . . . . .
H4B H 0.509094 1.023708 0.655152 0.026 Uiso 1 1 calc R U . . .
C5B C 0.5380(2) 0.9814(2) 0.79925(17) 0.0198(5) Uani 1 1 d . . . . .
C6B C 0.4875(2) 0.9146(2) 0.86234(16) 0.0198(5) Uani 1 1 d . . . . .
H6B H 0.533218 0.918796 0.932004 0.024 Uiso 1 1 calc R U . . .
C7B C 0.3690(2) 0.8414(2) 0.82214(16) 0.0184(4) Uani 1 1 d . . . . .
H7B H 0.332385 0.796733 0.864698 0.022 Uiso 1 1 calc R U . . .
C8B C 0.0350(2) 0.4847(2) 0.60561(15) 0.0156(4) Uani 1 1 d . . . . .
C9B C 0.0314(2) 0.5729(2) 0.69131(14) 0.0161(4) Uani 1 1 d . . . . .
H9B H -0.048718 0.633925 0.666851 0.019 Uiso 1 1 calc R U . . .
C10B C 0.0178(2) 0.4789(2) 0.77223(15) 0.0171(4) Uani 1 1 d . . . . .
H10C H -0.034405 0.397566 0.739821 0.021 Uiso 1 1 calc R U . . .
H10D H 0.108428 0.447383 0.814402 0.021 Uiso 1 1 calc R U . . .
C11B C -0.0491(2) 0.5424(2) 0.83911(16) 0.0217(5) Uani 1 1 d . . . . .
H11B H -0.140337 0.574637 0.796248 0.026 Uiso 1 1 calc R U . . .
C12B C 0.0281(3) 0.6633(3) 0.89838(19) 0.0307(6) Uani 1 1 d . . . . .
H12B H -0.016393 0.696372 0.942377 0.046 Uiso 1 1 calc R U . . .
H12C H 0.030666 0.736254 0.853002 0.046 Uiso 1 1 calc R U . . .
H12D H 0.119756 0.635063 0.937921 0.046 Uiso 1 1 calc R U . . .
C13B C -0.0658(3) 0.4324(3) 0.90888(17) 0.0289(5) Uani 1 1 d . . . . .
H13B H 0.022324 0.407602 0.957125 0.043 Uiso 1 1 calc R U . . .
H13C H -0.108282 0.351871 0.870362 0.043 Uiso 1 1 calc R U . . .
H13D H -0.122156 0.467600 0.943753 0.043 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 0.00 0.2450
0.00 -1.00 0.00 0.2070
-1.00 0.00 -1.00 0.0260
1.00 0.00 1.00 0.0260
-1.00 0.00 0.00 0.0320
1.00 0.00 -1.00 0.0230
-1.00 0.00 1.00 0.0360
-1.00 -1.00 0.00 0.1300
0.00 0.00 1.00 0.0310
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
C8A O2A H2A 112(2) . . ?
C1A N1A H1A 118.2(19) . . ?
C1A N1A C9A 120.63(18) . . ?
C9A N1A H1A 119.5(19) . . ?
O1A C1A N1A 120.5(2) . . ?
O1A C1A C2A 122.95(19) . . ?
N1A C1A C2A 116.54(18) . . ?
C3A C2A C1A 119.16(18) . . ?
C3A C2A C7A 118.8(2) . . ?
C7A C2A C1A 122.02(19) . . ?
C2A C3A H3A 119.7 . . ?
C4A C3A C2A 120.6(2) . . ?
C4A C3A H3A 119.7 . . ?
C3A C4A H4A 119.7 . . ?
C3A C4A C5A 120.6(2) . . ?
C5A C4A H4A 119.7 . . ?
C4A C5A C17A 121.4(2) . . ?
C6A C5A C4A 118.4(2) . . ?
C6A C5A C17A 120.2(2) . . ?
C5A C6A H6A 119.3 . . ?
C5A C6A C7A 121.49(19) . . ?
C7A C6A H6A 119.3 . . ?
C2A C7A H7A 120.0 . . ?
C6A C7A C2A 120.0(2) . . ?
C6A C7A H7A 120.0 . . ?
O2A C8A C9A 111.78(18) . . ?
O3A C8A O2A 124.1(2) . . ?
O3A C8A C9A 124.09(19) . . ?
N1A C9A C8A 110.23(17) . . ?
N1A C9A H9A 108.9 . . ?
N1A C9A C10A 109.43(17) . . ?
C8A C9A H9A 108.9 . . ?
C8A C9A C10A 110.57(17) . . ?
C10A C9A H9A 108.9 . . ?
C9A C10A H10A 109.1 . . ?
C9A C10A H10B 109.1 . . ?
H10A C10A H10B 107.8 . . ?
C11A C10A C9A 112.44(18) . . ?
C11A C10A H10A 109.1 . . ?
C11A C10A H10B 109.1 . . ?
C12A C11A C10A 122.2(2) . . ?
C12A C11A C16A 118.3(2) . . ?
C16A C11A C10A 119.5(2) . . ?
C11A C12A H12A 119.7 . . ?
C13A C12A C11A 120.7(2) . . ?
C13A C12A H12A 119.7 . . ?
C12A C13A H13A 119.8 . . ?
C14A C13A C12A 120.4(2) . . ?
C14A C13A H13A 119.8 . . ?
C13A C14A H14A 120.1 . . ?
C13A C14A C15A 119.8(2) . . ?
C15A C14A H14A 120.1 . . ?
C14A C15A H15A 120.2 . . ?
C14A C15A C16A 119.6(2) . . ?
C16A C15A H15A 120.2 . . ?
C11A C16A H16A 119.4 . . ?
C15A C16A C11A 121.3(2) . . ?
C15A C16A H16A 119.4 . . ?
C5A C17A H17A 109.5 . . ?
C5A C17A H17B 109.5 . . ?
C5A C17A H17C 109.5 . . ?
H17A C17A H17B 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C8B O2B H2B 112(2) . . ?
C1B N1B H1B 121.5(19) . . ?
C1B N1B C9B 120.67(18) . . ?
C9B N1B H1B 115.4(19) . . ?
O1B C1B N1B 119.8(2) . . ?
O1B C1B C2B 122.9(2) . . ?
N1B C1B C2B 117.24(19) . . ?
C3B C2B C1B 119.16(19) . . ?
C3B C2B C7B 119.1(2) . . ?
C7B C2B C1B 121.72(19) . . ?
C2B C3B H3B 119.5 . . ?
C4B C3B C2B 120.9(2) . . ?
C4B C3B H3B 119.5 . . ?
C3B C4B H4B 120.6 . . ?
C5B C4B C3B 118.8(2) . . ?
C5B C4B H4B 120.6 . . ?
C4B C5B Cl1B 119.73(18) . . ?
C6B C5B Cl1B 118.60(17) . . ?
C6B C5B C4B 121.7(2) . . ?
C5B C6B H6B 120.5 . . ?
C5B C6B C7B 119.0(2) . . ?
C7B C6B H6B 120.5 . . ?
C2B C7B H7B 119.7 . . ?
C6B C7B C2B 120.5(2) . . ?
C6B C7B H7B 119.7 . . ?
O2B C8B C9B 111.51(18) . . ?
O3B C8B O2B 124.9(2) . . ?
O3B C8B C9B 123.50(18) . . ?
N1B C9B C8B 110.88(17) . . ?
N1B C9B H9B 108.8 . . ?
N1B C9B C10B 110.88(16) . . ?
C8B C9B H9B 108.8 . . ?
C8B C9B C10B 108.48(19) . . ?
C10B C9B H9B 108.8 . . ?
C9B C10B H10C 108.4 . . ?
C9B C10B H10D 108.4 . . ?
H10C C10B H10D 107.4 . . ?
C11B C10B C9B 115.65(18) . . ?
C11B C10B H10C 108.4 . . ?
C11B C10B H10D 108.4 . . ?
C10B C11B H11B 108.2 . . ?
C10B C11B C13B 108.92(19) . . ?
C12B C11B C10B 113.06(19) . . ?
C12B C11B H11B 108.2 . . ?
C12B C11B C13B 110.25(19) . . ?
C13B C11B H11B 108.2 . . ?
C11B C12B H12B 109.5 . . ?
C11B C12B H12C 109.5 . . ?
C11B C12B H12D 109.5 . . ?
H12B C12B H12C 109.5 . . ?
H12B C12B H12D 109.5 . . ?
H12C C12B H12D 109.5 . . ?
C11B C13B H13B 109.5 . . ?
C11B C13B H13C 109.5 . . ?
C11B C13B H13D 109.5 . . ?
H13B C13B H13C 109.5 . . ?
H13B C13B H13D 109.5 . . ?
H13C C13B H13D 109.5 . . ?
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
O1A C1A 1.243(3) . ?
O2A H2A 0.84(3) . ?
O2A C8A 1.324(3) . ?
O3A C8A 1.213(3) . ?
N1A H1A 0.86(3) . ?
N1A C1A 1.343(3) . ?
N1A C9A 1.451(3) . ?
C1A C2A 1.493(3) . ?
C2A C3A 1.391(3) . ?
C2A C7A 1.402(3) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.389(3) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.399(3) . ?
C5A C6A 1.384(3) . ?
C5A C17A 1.512(3) . ?
C6A H6A 0.9500 . ?
C6A C7A 1.387(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.523(3) . ?
C9A H9A 1.0000 . ?
C9A C10A 1.545(3) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C10A C11A 1.514(3) . ?
C11A C12A 1.392(3) . ?
C11A C16A 1.393(3) . ?
C12A H12A 0.9500 . ?
C12A C13A 1.388(3) . ?
C13A H13A 0.9500 . ?
C13A C14A 1.384(3) . ?
C14A H14A 0.9500 . ?
C14A C15A 1.388(4) . ?
C15A H15A 0.9500 . ?
C15A C16A 1.390(3) . ?
C16A H16A 0.9500 . ?
C17A H17A 0.9800 . ?
C17A H17B 0.9800 . ?
C17A H17C 0.9800 . ?
Cl1B C5B 1.742(2) . ?
O1B C1B 1.250(3) . ?
O2B H2B 0.86(3) . ?
O2B C8B 1.316(3) . ?
O3B C8B 1.216(3) . ?
N1B H1B 0.84(3) . ?
N1B C1B 1.339(3) . ?
N1B C9B 1.454(3) . ?
C1B C2B 1.494(3) . ?
C2B C3B 1.392(3) . ?
C2B C7B 1.398(3) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.388(3) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.386(3) . ?
C5B C6B 1.385(3) . ?
C6B H6B 0.9500 . ?
C6B C7B 1.390(3) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.527(3) . ?
C9B H9B 1.0000 . ?
C9B C10B 1.541(3) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
C10B C11B 1.532(3) . ?
C11B H11B 1.0000 . ?
C11B C12B 1.522(3) . ?
C11B C13B 1.534(3) . ?
C12B H12B 0.9800 . ?
C12B H12C 0.9800 . ?
C12B H12D 0.9800 . ?
C13B H13B 0.9800 . ?
C13B H13C 0.9800 . ?
C13B H13D 0.9800 . ?
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
_geom_hbond_publ_flag
O2A H2A O1A 0.84(3) 1.78(4) 2.615(2) 176(3) 2_657 yes
N1A H1A O3B 0.86(3) 2.15(3) 2.991(2) 166(3) . yes
O2B H2B O1B 0.86(3) 1.74(4) 2.597(2) 175(3) 2_546 yes
N1B H1B O3A 0.84(3) 2.08(3) 2.916(2) 174(3) . yes
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
O1A C1A C2A C3A 22.7(3) . . . . ?
O1A C1A C2A C7A -157.1(2) . . . . ?
O2A C8A C9A N1A 158.89(17) . . . . ?
O2A C8A C9A C10A -80.0(2) . . . . ?
O3A C8A C9A N1A -21.8(3) . . . . ?
O3A C8A C9A C10A 99.3(2) . . . . ?
N1A C1A C2A C3A -157.5(2) . . . . ?
N1A C1A C2A C7A 22.7(3) . . . . ?
N1A C9A C10A C11A -67.4(2) . . . . ?
C1A N1A C9A C8A -65.0(2) . . . . ?
C1A N1A C9A C10A 173.24(19) . . . . ?
C1A C2A C3A C4A -178.4(2) . . . . ?
C1A C2A C7A C6A 178.6(2) . . . . ?
C2A C3A C4A C5A 0.5(3) . . . . ?
C3A C2A C7A C6A -1.1(3) . . . . ?
C3A C4A C5A C6A -2.4(3) . . . . ?
C3A C4A C5A C17A 176.8(2) . . . . ?
C4A C5A C6A C7A 2.6(3) . . . . ?
C5A C6A C7A C2A -0.9(4) . . . . ?
C7A C2A C3A C4A 1.3(3) . . . . ?
C8A C9A C10A C11A 170.97(18) . . . . ?
C9A N1A C1A O1A -1.3(3) . . . . ?
C9A N1A C1A C2A 178.93(18) . . . . ?
C9A C10A C11A C12A 89.3(2) . . . . ?
C9A C10A C11A C16A -90.1(2) . . . . ?
C10A C11A C12A C13A -178.1(2) . . . . ?
C10A C11A C16A C15A 178.6(2) . . . . ?
C11A C12A C13A C14A -0.6(4) . . . . ?
C12A C11A C16A C15A -0.8(3) . . . . ?
C12A C13A C14A C15A -0.7(4) . . . . ?
C13A C14A C15A C16A 1.2(4) . . . . ?
C14A C15A C16A C11A -0.4(4) . . . . ?
C16A C11A C12A C13A 1.4(3) . . . . ?
C17A C5A C6A C7A -176.6(2) . . . . ?
Cl1B C5B C6B C7B 179.14(17) . . . . ?
O1B C1B C2B C3B -20.5(3) . . . . ?
O1B C1B C2B C7B 159.4(2) . . . . ?
O2B C8B C9B N1B -153.25(18) . . . . ?
O2B C8B C9B C10B 84.8(2) . . . . ?
O3B C8B C9B N1B 29.4(3) . . . . ?
O3B C8B C9B C10B -92.6(2) . . . . ?
N1B C1B C2B C3B 159.7(2) . . . . ?
N1B C1B C2B C7B -20.4(3) . . . . ?
N1B C9B C10B C11B 84.6(2) . . . . ?
C1B N1B C9B C8B 64.4(3) . . . . ?
C1B N1B C9B C10B -175.07(19) . . . . ?
C1B C2B C3B C4B -179.8(2) . . . . ?
C1B C2B C7B C6B 178.8(2) . . . . ?
C2B C3B C4B C5B 0.8(4) . . . . ?
C3B C2B C7B C6B -1.3(3) . . . . ?
C3B C4B C5B Cl1B 179.82(18) . . . . ?
C3B C4B C5B C6B -0.7(4) . . . . ?
C4B C5B C6B C7B -0.3(3) . . . . ?
C5B C6B C7B C2B 1.3(3) . . . . ?
C7B C2B C3B C4B 0.2(3) . . . . ?
C8B C9B C10B C11B -153.43(19) . . . . ?
C9B N1B C1B O1B 0.8(3) . . . . ?
C9B N1B C1B C2B -179.38(18) . . . . ?
C9B C10B C11B C12B -62.0(3) . . . . ?
C9B C10B C11B C13B 175.07(19) . . . . ?
