#------------------------------------------------------------------------------
#$Date: 2023-06-05 07:52:34 +0300 (Mon, 05 Jun 2023) $
#$Revision: 284317 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/93/7159307.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_7159307
loop_
_publ_author_name
'Liu, Yi'
'Gao, Wei'
'Yuan, Sitian'
'Ni, Mengjia'
'Hao, Tianxin'
'Zeng, Cuiying'
'Xu, Xinyi'
'Fu, Yang'
'Peng, Yiyuan'
'Ding, Qiuping'
_publ_section_title
;
 One-pot synthesis of 11-sulfenyl dibenzodiazepines via tandem
 sulfenylation/cyclization of o-isocyanodiaryl amines and diaryl
 disulfides.
;
_journal_issue                   20
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              4257
_journal_page_last               4263
_journal_paper_doi               10.1039/d3ob00220a
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C20 H16 N2 S'
_chemical_formula_sum            'C20 H16 N2 S'
_chemical_formula_weight         316.41
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-02
_audit_creation_method
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_audit_update_record
;
2022-07-02 deposited with the CCDC.	2023-04-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   8.3581(7)
_cell_length_b                   15.8178(11)
_cell_length_c                   24.7199(17)
_cell_measurement_reflns_used    2663
_cell_measurement_temperature    298
_cell_measurement_theta_max      26.5990
_cell_measurement_theta_min      3.7080
_cell_volume                     3268.1(4)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      298
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.839
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  -5.00   1.00   20.31    --  -15.76  77.00 120.00   37
  2  ω    -29.00   2.00   1.00   20.31    --  -15.76  77.00-180.00   31
  3  ω      6.00  40.00   1.00   20.31    --  -15.76  77.00-180.00   34
  4  ω     -8.00  39.00   1.00   20.31    --   16.70  77.00   0.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0578133000
_diffrn_orient_matrix_UB_12      -0.0053963000
_diffrn_orient_matrix_UB_13      -0.0207071000
_diffrn_orient_matrix_UB_21      0.0434148000
_diffrn_orient_matrix_UB_22      -0.0281133000
_diffrn_orient_matrix_UB_23      0.0168794000
_diffrn_orient_matrix_UB_31      -0.0442837000
_diffrn_orient_matrix_UB_32      -0.0345790000
_diffrn_orient_matrix_UB_33      -0.0104568000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.839
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9778
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.839
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.315
_diffrn_reflns_theta_min         3.296
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48236
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.080
_refine_ls_R_factor_all          0.0881
_refine_ls_R_factor_gt           0.0529
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0435P)²+0.7753P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1131
_refine_ls_wR_factor_ref         0.1286
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2517
_reflns_number_total             3757
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00220a2.cif
_cod_data_source_block           liuyi-3-28_auto
_cod_depositor_comments          'Adding full bibliography for 7159307.cif.'
_cod_database_code               7159307
_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.
;
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.967
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.405
_oxdiff_exptl_absorpt_empirical_full_min 0.451
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.50153(8) 0.37128(4) 0.67587(3) 0.0674(2) Uani 1 1 d . . . . .
N1 N 0.16771(19) 0.33856(10) 0.54199(6) 0.0435(4) Uani 1 1 d . . . . .
N2 N 0.36182(19) 0.25053(10) 0.61925(6) 0.0418(4) Uani 1 1 d . . . . .
C1 C 0.1582(2) 0.24873(12) 0.54706(7) 0.0405(4) Uani 1 1 d . . . . .
C2 C 0.0681(3) 0.19956(14) 0.51215(9) 0.0553(6) Uani 1 1 d . . . . .
H2 H 0.011417 0.225155 0.484224 0.066 Uiso 1 1 calc R U . . .
C3 C 0.0616(3) 0.11270(15) 0.51841(10) 0.0664(7) Uani 1 1 d . . . . .
H3 H 0.001046 0.080391 0.494550 0.080 Uiso 1 1 calc R U . . .
C4 C 0.1435(3) 0.07398(14) 0.55946(10) 0.0615(6) Uani 1 1 d . . . . .
H4 H 0.135211 0.015863 0.564429 0.074 Uiso 1 1 calc R U . . .
C5 C 0.2381(2) 0.12153(12) 0.59331(8) 0.0477(5) Uani 1 1 d . . . . .
H5 H 0.296849 0.094902 0.620331 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2471(2) 0.20902(12) 0.58769(7) 0.0380(4) Uani 1 1 d . . . . .
C7 C 0.3421(2) 0.32427(12) 0.63901(7) 0.0427(5) Uani 1 1 d . . . . .
C8 C 0.1964(2) 0.37725(11) 0.63655(7) 0.0441(5) Uani 1 1 d . . . . .
C9 C 0.1431(3) 0.42190(14) 0.68159(8) 0.0597(6) Uani 1 1 d . . . . .
H9 H 0.200360 0.418726 0.713779 0.072 Uiso 1 1 calc R U . . .
C10 C 0.0069(3) 0.47068(15) 0.67920(11) 0.0724(8) Uani 1 1 d . . . . .
H10 H -0.027997 0.499845 0.709662 0.087 Uiso 1 1 calc R U . . .
C11 C -0.0766(3) 0.47599(15) 0.63188(12) 0.0726(7) Uani 1 1 d . . . . .
H11 H -0.167700 0.509634 0.630099 0.087 Uiso 1 1 calc R U . . .
C12 C -0.0272(3) 0.43189(13) 0.58653(10) 0.0577(6) Uani 1 1 d . . . . .
H12 H -0.086346 0.435269 0.554730 0.069 Uiso 1 1 calc R U . . .
C13 C 0.1101(2) 0.38262(12) 0.58824(8) 0.0423(5) Uani 1 1 d . . . . .
C14 C 0.1229(3) 0.37373(15) 0.48949(8) 0.0662(7) Uani 1 1 d . . . . .
H14A H 0.179603 0.344518 0.461366 0.099 Uiso 1 1 calc R U . . .
H14B H 0.149735 0.432717 0.488471 0.099 Uiso 1 1 calc R U . . .
H14C H 0.009814 0.367066 0.484126 0.099 Uiso 1 1 calc R U . . .
C15 C 0.6334(3) 0.28449(14) 0.68337(8) 0.0528(6) Uani 1 1 d . . . . .
C16 C 0.7351(3) 0.26029(16) 0.64205(9) 0.0646(7) Uani 1 1 d . . . . .
H16 H 0.737133 0.290923 0.609943 0.078 Uiso 1 1 calc R U . . .
C17 C 0.8332(3) 0.1912(2) 0.64818(11) 0.0745(7) Uani 1 1 d . . . . .
H17 H 0.900547 0.174893 0.620119 0.089 Uiso 1 1 calc R U . . .
C18 C 0.8317(3) 0.14623(19) 0.69571(12) 0.0778(8) Uani 1 1 d . . . . .
H18 H 0.897126 0.099073 0.699674 0.093 Uiso 1 1 calc R U . . .
C19 C 0.7337(3) 0.17093(18) 0.73735(11) 0.0779(8) Uani 1 1 d . . . . .
H19 H 0.734295 0.141073 0.769760 0.093 Uiso 1 1 calc R U . . .
C20 C 0.6343(3) 0.23988(16) 0.73129(9) 0.0610(6) Uani 1 1 d . . . . .
H20 H 0.567840 0.256315 0.759563 0.073 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 0.0033 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'
S S 0.1246 0.1234 '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
C15 S1 C7 101.31(9) . . ?
C1 N1 C14 116.26(16) . . ?
C13 N1 C1 113.45(14) . . ?
C13 N1 C14 116.14(16) . . ?
C7 N2 C6 123.65(17) . . ?
C2 C1 N1 122.29(17) . . ?
C2 C1 C6 118.97(18) . . ?
C6 C1 N1 118.71(16) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(2) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.5(2) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.5 . . ?
C4 C5 C6 120.93(19) . . ?
C6 C5 H5 119.5 . . ?
C1 C6 N2 123.60(17) . . ?
C5 C6 N2 116.60(17) . . ?
C5 C6 C1 119.28(17) . . ?
N2 C7 S1 118.83(15) . . ?
N2 C7 C8 127.49(18) . . ?
C8 C7 S1 113.65(14) . . ?
C9 C8 C7 121.20(19) . . ?
C9 C8 C13 119.2(2) . . ?
C13 C8 C7 119.61(17) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 121.0(2) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(2) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(2) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.3(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 N1 118.83(17) . . ?
C12 C13 N1 122.03(19) . . ?
C12 C13 C8 119.13(19) . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S1 121.32(18) . . ?
C20 C15 S1 119.36(18) . . ?
C20 C15 C16 119.3(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 C15 120.3(2) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.0 . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.0(3) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.9 . . ?
C18 C19 C20 120.2(2) . . ?
C20 C19 H19 119.9 . . ?
C15 C20 C19 120.1(2) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.777(2) . ?
S1 C15 1.770(2) . ?
N1 C1 1.429(2) . ?
N1 C13 1.423(2) . ?
N1 C14 1.461(2) . ?
N2 C6 1.400(2) . ?
N2 C7 1.275(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.398(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.369(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.375(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.393(3) . ?
C7 C8 1.480(3) . ?
C8 C9 1.392(3) . ?
C8 C13 1.398(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.365(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.388(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.383(3) . ?
C15 C20 1.379(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.374(3) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.372(4) . ?
C19 H19 0.9300 . ?
C19 C20 1.379(3) . ?
C20 H20 0.9300 . ?
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
S1 C7 C8 C9 -41.1(2) . . . . ?
S1 C7 C8 C13 139.02(16) . . . . ?
S1 C15 C16 C17 -178.10(17) . . . . ?
S1 C15 C20 C19 178.52(17) . . . . ?
N1 C1 C2 C3 -179.8(2) . . . . ?
N1 C1 C6 N2 -9.0(3) . . . . ?
N1 C1 C6 C5 179.55(17) . . . . ?
N2 C7 C8 C9 137.0(2) . . . . ?
N2 C7 C8 C13 -42.8(3) . . . . ?
C1 N1 C13 C8 68.2(2) . . . . ?
C1 N1 C13 C12 -113.0(2) . . . . ?
C1 C2 C3 C4 0.4(4) . . . . ?
C2 C1 C6 N2 169.11(18) . . . . ?
C2 C1 C6 C5 -2.4(3) . . . . ?
C2 C3 C4 C5 -2.7(4) . . . . ?
C3 C4 C5 C6 2.4(3) . . . . ?
C4 C5 C6 N2 -171.96(19) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C6 N2 C7 S1 -177.25(13) . . . . ?
C6 N2 C7 C8 4.7(3) . . . . ?
C6 C1 C2 C3 2.2(3) . . . . ?
C7 S1 C15 C16 80.68(19) . . . . ?
C7 S1 C15 C20 -99.05(17) . . . . ?
C7 N2 C6 C1 42.5(3) . . . . ?
C7 N2 C6 C5 -145.77(19) . . . . ?
C7 C8 C9 C10 -179.6(2) . . . . ?
C7 C8 C13 N1 -1.8(3) . . . . ?
C7 C8 C13 C12 179.43(17) . . . . ?
C8 C9 C10 C11 -0.5(4) . . . . ?
C9 C8 C13 N1 178.36(17) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
C9 C10 C11 C12 1.0(4) . . . . ?
C10 C11 C12 C13 -1.2(4) . . . . ?
C11 C12 C13 N1 -177.88(19) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C13 N1 C1 C2 119.3(2) . . . . ?
C13 N1 C1 C6 -62.7(2) . . . . ?
C13 C8 C9 C10 0.3(3) . . . . ?
C14 N1 C1 C2 -19.3(3) . . . . ?
C14 N1 C1 C6 158.72(18) . . . . ?
C14 N1 C13 C8 -153.23(19) . . . . ?
C14 N1 C13 C12 25.6(3) . . . . ?
C15 S1 C7 N2 -10.70(18) . . . . ?
C15 S1 C7 C8 167.62(14) . . . . ?
C15 C16 C17 C18 -0.6(4) . . . . ?
C16 C15 C20 C19 -1.2(3) . . . . ?
C16 C17 C18 C19 -0.8(4) . . . . ?
C17 C18 C19 C20 1.2(4) . . . . ?
C18 C19 C20 C15 -0.2(3) . . . . ?
C20 C15 C16 C17 1.6(3) . . . . ?
