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#$Date: 2025-04-05 05:48:08 +0300 (Sat, 05 Apr 2025) $
#$Revision: 298876 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/74/7717468.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_7717468
loop_
_publ_author_name
'Sai Kumar, Gobbilla'
'Bano, Kulsum'
'Biswal, Priyabrata'
'Dey, Soumyadip'
'Kumar, Ravi'
'Sau, Abhijit'
'Chandrasekhar, Vadapalli'
'Panda, Tarun K.'
_publ_section_title
;
 Indium-catalyzed hydrosilylation of nitroarenes to aromatic amines.
;
_journal_issue                   4
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              1552
_journal_page_last               1559
_journal_paper_doi               10.1039/d4dt02861a
_journal_volume                  54
_journal_year                    2025
_chemical_formula_sum            'C22 H32 Cl In N6 O2'
_chemical_formula_weight         562.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2024-07-28 deposited with the CCDC.	2024-11-11 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.026(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.309(2)
_cell_length_b                   9.8212(9)
_cell_length_c                   15.5256(14)
_cell_measurement_reflns_used    76971
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      27.163
_cell_measurement_theta_min      2.410
_cell_volume                     2529.7(4)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_collection
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies,Version 1.171.35.19 (release 27-10-2011CrysAlis171 .NET)(compiled Oct 27'
_computing_molecular_graphics    'ORTEP 3.0 & Olex 2.1'
_computing_publication_material  WinGX
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  Bruker
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0749
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            76971
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.163
_diffrn_reflns_theta_min         2.410
_diffrn_source                   'Bruker (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    1.069
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.790
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.478
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         5619
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0309
_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)+(0.0263P)²+0.9528P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0676
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4228
_reflns_number_total             5619
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4dt02861a2.cif
_cod_data_source_block           shelx_CCDC2
_cod_depositor_comments
'Adding full bibliography for 7717466--7717468.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7717468
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
In1 In 0.18418(2) 0.73308(2) 0.30179(2) 0.04446(7) Uani 1 1 d . . . . .
Cl1 Cl 0.10068(4) 0.82860(8) 0.37702(5) 0.0625(2) Uani 1 1 d . . . . .
O1 O 0.10733(17) 1.1374(3) 0.1484(2) 0.1008(8) Uani 1 1 d . . . . .
O2 O 0.56013(15) 0.3536(3) 0.35967(18) 0.0885(7) Uani 1 1 d . . . . .
N1 N 0.21833(14) 0.5452(2) 0.38597(16) 0.0552(6) Uani 1 1 d . . . . .
N2 N 0.09812(13) 0.5792(2) 0.21351(16) 0.0570(6) Uani 1 1 d . . . . .
N3 N 0.10209(14) 0.8443(2) 0.14589(16) 0.0565(6) Uani 1 1 d . . . . .
N4 N 0.28019(12) 0.8730(2) 0.37283(15) 0.0480(5) Uani 1 1 d . . . . .
N5 N 0.27908(13) 0.6894(2) 0.24126(16) 0.0532(6) Uani 1 1 d . . . . .
N6 N 0.39908(15) 0.4566(2) 0.28523(19) 0.0629(7) Uani 1 1 d . . . . .
C1 C 0.2750(2) 0.4989(3) 0.4689(2) 0.0692(9) Uani 1 1 d . . . . .
H1 H 0.314595 0.551893 0.514566 0.083 Uiso 1 1 calc R U . . .
C2 C 0.2653(2) 0.3598(4) 0.4756(3) 0.0837(11) Uani 1 1 d . . . . .
H2 H 0.296637 0.303873 0.526098 0.100 Uiso 1 1 calc R U . . .
C3 C 0.2014(2) 0.3201(3) 0.3948(3) 0.0824(10) Uani 1 1 d . . . . .
H3 H 0.180791 0.232365 0.379675 0.099 Uiso 1 1 calc R U . . .
C4 C 0.17282(18) 0.4360(3) 0.3393(2) 0.0597(7) Uani 1 1 d . . . . .
C5 C 0.10988(18) 0.4584(3) 0.2480(2) 0.0629(8) Uani 1 1 d . . . . .
H5 H 0.077604 0.386613 0.213513 0.075 Uiso 1 1 calc R U . . .
C6 C 0.03543(19) 0.6169(4) 0.1224(2) 0.0744(9) Uani 1 1 d . . . . .
H6A H -0.011318 0.650562 0.129933 0.089 Uiso 1 1 calc R U . . .
H6B H 0.019242 0.538548 0.080423 0.089 Uiso 1 1 calc R U . . .
C7 C 0.0688(2) 0.7266(4) 0.0810(2) 0.0832(11) Uani 1 1 d . . . . .
H7A H 0.110906 0.687919 0.066314 0.100 Uiso 1 1 calc R U . . .
H7B H 0.026215 0.758536 0.021956 0.100 Uiso 1 1 calc R U . . .
C8 C 0.03701(18) 0.9307(4) 0.1466(2) 0.0706(9) Uani 1 1 d . . . . .
H8A H 0.009931 0.883628 0.179810 0.085 Uiso 1 1 calc R U . . .
H8B H -0.002140 0.946125 0.081746 0.085 Uiso 1 1 calc R U . . .
C9 C 0.0667(2) 1.0627(4) 0.1929(3) 0.0893(12) Uani 1 1 d . . . . .
H9A H 0.021503 1.115911 0.191318 0.107 Uiso 1 1 calc R U . . .
H9B H 0.103113 1.047542 0.258961 0.107 Uiso 1 1 calc R U . . .
C10 C 0.1500(2) 0.9278(4) 0.1054(2) 0.0823(11) Uani 1 1 d . . . . .
H10A H 0.198013 0.877909 0.112827 0.099 Uiso 1 1 calc R U . . .
H10B H 0.117743 0.942066 0.037933 0.099 Uiso 1 1 calc R U . . .
C11 C 0.1738(2) 1.0634(4) 0.1544(3) 0.0979(13) Uani 1 1 d . . . . .
H11A H 0.209784 1.048975 0.220740 0.117 Uiso 1 1 calc R U . . .
H11B H 0.202814 1.115181 0.125607 0.117 Uiso 1 1 calc R U . . .
C12 C 0.29667(18) 0.9749(3) 0.43663(19) 0.0557(7) Uani 1 1 d . . . . .
H12 H 0.262371 1.004096 0.463149 0.067 Uiso 1 1 calc R U . . .
C13 C 0.37112(19) 1.0295(3) 0.4568(2) 0.0658(8) Uani 1 1 d . . . . .
H13 H 0.395918 1.100431 0.498720 0.079 Uiso 1 1 calc R U . . .
C14 C 0.40219(18) 0.9584(3) 0.4029(2) 0.0636(8) Uani 1 1 d . . . . .
H14 H 0.451973 0.972390 0.401627 0.076 Uiso 1 1 calc R U . . .
C15 C 0.34490(15) 0.8625(3) 0.35105(19) 0.0499(6) Uani 1 1 d . . . . .
C16 C 0.34175(17) 0.7636(3) 0.2827(2) 0.0559(7) Uani 1 1 d . . . . .
H16 H 0.385629 0.752845 0.267924 0.067 Uiso 1 1 calc R U . . .
C17 C 0.28044(19) 0.5867(3) 0.1738(2) 0.0741(9) Uani 1 1 d . . . . .
H17A H 0.312621 0.620260 0.142192 0.089 Uiso 1 1 calc R U . . .
H17B H 0.225976 0.572675 0.125682 0.089 Uiso 1 1 calc R U . . .
C18 C 0.3143(2) 0.4524(3) 0.2202(3) 0.0803(10) Uani 1 1 d . . . . .
H18A H 0.283834 0.421764 0.254748 0.096 Uiso 1 1 calc R U . . .
H18B H 0.306747 0.385844 0.171028 0.096 Uiso 1 1 calc R U . . .
C19 C 0.4230(3) 0.3331(4) 0.3423(3) 0.0915(12) Uani 1 1 d . . . . .
H19A H 0.412261 0.254734 0.300645 0.110 Uiso 1 1 calc R U . . .
H19B H 0.391242 0.323741 0.378528 0.110 Uiso 1 1 calc R U . . .
C20 C 0.5109(3) 0.3360(4) 0.4091(3) 0.1047(14) Uani 1 1 d . . . . .
H20A H 0.520758 0.409980 0.454028 0.126 Uiso 1 1 calc R U . . .
H20B H 0.525281 0.251475 0.444634 0.126 Uiso 1 1 calc R U . . .
C21 C 0.5377(2) 0.4765(4) 0.3081(3) 0.0768(10) Uani 1 1 d . . . . .
H21A H 0.571946 0.491795 0.275456 0.092 Uiso 1 1 calc R U . . .
H21B H 0.545577 0.551550 0.351725 0.092 Uiso 1 1 calc R U . . .
C22 C 0.45135(18) 0.4730(3) 0.2369(2) 0.0664(8) Uani 1 1 d . . . . .
H22A H 0.438064 0.556956 0.200511 0.080 Uiso 1 1 calc R U . . .
H22B H 0.443146 0.397980 0.193097 0.080 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
In In -0.7276 1.3100 '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'
O O 0.0106 0.0060 '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'
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'
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
N4 In1 N1 105.60(8) . . ?
N4 In1 N2 169.36(8) . . ?
N1 In1 N2 75.00(9) . . ?
N4 In1 N5 74.71(8) . . ?
N1 In1 N5 90.69(8) . . ?
N2 In1 N5 94.69(8) . . ?
N4 In1 Cl1 92.89(6) . . ?
N1 In1 Cl1 96.62(6) . . ?
N2 In1 Cl1 97.61(7) . . ?
N5 In1 Cl1 166.97(6) . . ?
N4 In1 N3 104.22(8) . . ?
N1 In1 N3 148.06(9) . . ?
N2 In1 N3 73.57(9) . . ?
N5 In1 N3 86.31(8) . . ?
Cl1 In1 N3 93.04(6) . . ?
C11 O1 C9 108.9(3) . . ?
C21 O2 C20 108.2(3) . . ?
C1 N1 C4 107.1(3) . . ?
C1 N1 In1 139.8(2) . . ?
C4 N1 In1 112.87(19) . . ?
C5 N2 C6 124.8(3) . . ?
C5 N2 In1 115.3(2) . . ?
C6 N2 In1 119.9(2) . . ?
C8 N3 C7 110.7(3) . . ?
C8 N3 C10 107.7(2) . . ?
C7 N3 C10 106.4(3) . . ?
C8 N3 In1 113.78(17) . . ?
C7 N3 In1 102.91(17) . . ?
C10 N3 In1 114.96(17) . . ?
C12 N4 C15 106.8(2) . . ?
C12 N4 In1 137.43(19) . . ?
C15 N4 In1 115.75(17) . . ?
C16 N5 C17 118.0(2) . . ?
C16 N5 In1 110.73(18) . . ?
C17 N5 In1 130.95(19) . . ?
C18 N6 C22 112.9(3) . . ?
C18 N6 C19 110.9(3) . . ?
C22 N6 C19 108.2(2) . . ?
N1 C1 C2 109.5(3) . . ?
N1 C1 H1 125.3 . . ?
C2 C1 H1 125.3 . . ?
C3 C2 C1 107.5(3) . . ?
C3 C2 H2 126.3 . . ?
C1 C2 H2 126.3 . . ?
C2 C3 C4 106.8(3) . . ?
C2 C3 H3 126.6 . . ?
C4 C3 H3 126.6 . . ?
N1 C4 C3 109.2(3) . . ?
N1 C4 C5 117.8(3) . . ?
C3 C4 C5 133.0(3) . . ?
N2 C5 C4 118.9(3) . . ?
N2 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
N2 C6 C7 107.7(3) . . ?
N2 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
N2 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
N3 C7 C6 113.0(3) . . ?
N3 C7 H7A 109.0 . . ?
C6 C7 H7A 109.0 . . ?
N3 C7 H7B 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N3 C8 C9 112.4(3) . . ?
N3 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N3 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
O1 C9 C8 112.4(3) . . ?
O1 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
O1 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 N3 111.3(3) . . ?
C11 C10 H10A 109.4 . . ?
N3 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
N3 C10 H10B 109.4 . . ?
H10A C10 H10B 108.0 . . ?
O1 C11 C10 111.8(3) . . ?
O1 C11 H11A 109.3 . . ?
C10 C11 H11A 109.3 . . ?
O1 C11 H11B 109.3 . . ?
C10 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N4 C12 C13 110.5(3) . . ?
N4 C12 H12 124.8 . . ?
C13 C12 H12 124.8 . . ?
C12 C13 C14 106.7(3) . . ?
C12 C13 H13 126.6 . . ?
C14 C13 H13 126.6 . . ?
C13 C14 C15 106.9(3) . . ?
C13 C14 H14 126.6 . . ?
C15 C14 H14 126.6 . . ?
N4 C15 C14 109.1(2) . . ?
N4 C15 C16 118.1(2) . . ?
C14 C15 C16 132.8(3) . . ?
N5 C16 C15 120.6(2) . . ?
N5 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
N5 C17 C18 112.9(3) . . ?
N5 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N5 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
N6 C18 C17 114.3(3) . . ?
N6 C18 H18A 108.7 . . ?
C17 C18 H18A 108.7 . . ?
N6 C18 H18B 108.7 . . ?
C17 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
N6 C19 C20 111.3(3) . . ?
N6 C19 H19A 109.4 . . ?
C20 C19 H19A 109.4 . . ?
N6 C19 H19B 109.4 . . ?
C20 C19 H19B 109.4 . . ?
H19A C19 H19B 108.0 . . ?
O2 C20 C19 111.7(3) . . ?
O2 C20 H20A 109.3 . . ?
C19 C20 H20A 109.3 . . ?
O2 C20 H20B 109.3 . . ?
C19 C20 H20B 109.3 . . ?
H20A C20 H20B 107.9 . . ?
O2 C21 C22 111.3(3) . . ?
O2 C21 H21A 109.4 . . ?
C22 C21 H21A 109.4 . . ?
O2 C21 H21B 109.4 . . ?
C22 C21 H21B 109.4 . . ?
H21A C21 H21B 108.0 . . ?
N6 C22 C21 109.9(3) . . ?
N6 C22 H22A 109.7 . . ?
C21 C22 H22A 109.7 . . ?
N6 C22 H22B 109.7 . . ?
C21 C22 H22B 109.7 . . ?
H22A C22 H22B 108.2 . . ?
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
In1 N4 2.134(2) . ?
In1 N1 2.194(2) . ?
In1 N2 2.195(2) . ?
In1 N5 2.338(2) . ?
In1 Cl1 2.4684(7) . ?
In1 N3 2.497(2) . ?
O1 C11 1.387(4) . ?
O1 C9 1.416(4) . ?
O2 C21 1.410(4) . ?
O2 C20 1.420(4) . ?
N1 C1 1.345(4) . ?
N1 C4 1.363(4) . ?
N2 C5 1.282(4) . ?
N2 C6 1.443(4) . ?
N3 C8 1.467(3) . ?
N3 C7 1.484(4) . ?
N3 C10 1.517(4) . ?
N4 C12 1.350(3) . ?
N4 C15 1.367(3) . ?
N5 C16 1.280(3) . ?
N5 C17 1.462(3) . ?
N6 C18 1.451(4) . ?
N6 C22 1.454(4) . ?
N6 C19 1.456(4) . ?
C1 C2 1.387(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.361(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.390(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.416(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.509(5) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.470(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.504(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.372(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.386(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.422(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.505(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.501(5) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.498(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
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
C7 H7A Cl1 0.97 2.87 3.497(3) 123.3 4_575 yes
C8 H8A Cl1 0.97 2.85 3.410(3) 117.7 . yes
C9 H9A Cl1 0.97 2.91 3.817(4) 155.6 2 yes
C9 H9B Cl1 0.97 2.84 3.513(4) 127.4 . yes
C7 H7A Cl1 0.97 2.87 3.497(3) 123.3 4_575 yes
C8 H8A Cl1 0.97 2.85 3.410(3) 117.7 . yes
C9 H9A Cl1 0.97 2.91 3.817(4) 155.6 2 yes
C9 H9B Cl1 0.97 2.84 3.513(4) 127.4 . 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
C4 N1 C1 C2 -0.5(3) . . . . ?
In1 N1 C1 C2 -174.5(2) . . . . ?
N1 C1 C2 C3 0.3(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C1 N1 C4 C3 0.6(3) . . . . ?
In1 N1 C4 C3 176.4(2) . . . . ?
C1 N1 C4 C5 -178.2(3) . . . . ?
In1 N1 C4 C5 -2.5(3) . . . . ?
C2 C3 C4 N1 -0.5(4) . . . . ?
C2 C3 C4 C5 178.1(3) . . . . ?
C6 N2 C5 C4 -178.8(3) . . . . ?
In1 N2 C5 C4 3.1(4) . . . . ?
N1 C4 C5 N2 -0.4(4) . . . . ?
C3 C4 C5 N2 -178.9(3) . . . . ?
C5 N2 C6 C7 -144.7(3) . . . . ?
In1 N2 C6 C7 33.3(3) . . . . ?
C8 N3 C7 C6 -76.2(3) . . . . ?
C10 N3 C7 C6 167.0(3) . . . . ?
In1 N3 C7 C6 45.7(3) . . . . ?
N2 C6 C7 N3 -54.2(4) . . . . ?
C7 N3 C8 C9 -167.5(3) . . . . ?
C10 N3 C8 C9 -51.5(3) . . . . ?
In1 N3 C8 C9 77.2(3) . . . . ?
C11 O1 C9 C8 -61.3(4) . . . . ?
N3 C8 C9 O1 58.6(4) . . . . ?
C8 N3 C10 C11 50.6(3) . . . . ?
C7 N3 C10 C11 169.3(3) . . . . ?
In1 N3 C10 C11 -77.5(3) . . . . ?
C9 O1 C11 C10 60.5(4) . . . . ?
N3 C10 C11 O1 -57.2(4) . . . . ?
C15 N4 C12 C13 -0.5(3) . . . . ?
In1 N4 C12 C13 179.6(2) . . . . ?
N4 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C12 N4 C15 C14 0.6(3) . . . . ?
In1 N4 C15 C14 -179.51(18) . . . . ?
C12 N4 C15 C16 -178.4(2) . . . . ?
In1 N4 C15 C16 1.5(3) . . . . ?
C13 C14 C15 N4 -0.4(3) . . . . ?
C13 C14 C15 C16 178.3(3) . . . . ?
C17 N5 C16 C15 -178.2(3) . . . . ?
In1 N5 C16 C15 -3.6(3) . . . . ?
N4 C15 C16 N5 1.7(4) . . . . ?
C14 C15 C16 N5 -177.0(3) . . . . ?
C16 N5 C17 C18 88.3(4) . . . . ?
In1 N5 C17 C18 -84.9(3) . . . . ?
C22 N6 C18 C17 -70.8(3) . . . . ?
C19 N6 C18 C17 167.6(3) . . . . ?
N5 C17 C18 N6 -66.1(4) . . . . ?
C18 N6 C19 C20 179.4(3) . . . . ?
C22 N6 C19 C20 55.1(4) . . . . ?
C21 O2 C20 C19 58.5(4) . . . . ?
N6 C19 C20 O2 -57.3(4) . . . . ?
C20 O2 C21 C22 -60.9(4) . . . . ?
C18 N6 C22 C21 -180.0(3) . . . . ?
C19 N6 C22 C21 -56.8(4) . . . . ?
O2 C21 C22 N6 61.7(4) . . . . ?
