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#$Date: 2022-10-24 11:32:12 +0300 (Mon, 24 Oct 2022) $
#$Revision: 278734 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/59/8105954.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_8105954
loop_
_publ_author_name
'Tan, Sang Loon'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of the co-crystal
 4-[(4-carboxyphenyl)disulfanyl]benzoic
 acid--(1E,4E)-1-N,4-N-bis(pyridin-4-ylmethylidene)cyclohexane-1,4-diamine
 (1/1), C14H10O4S2⋅C18H20N4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1121
_journal_page_last               1123
_journal_paper_doi               10.1515/ncrs-2019-0488
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C18 H20 N4, C14 H10 O4 S2'
_chemical_formula_sum            'C32 H30 N4 O4 S2'
_chemical_formula_weight         598.72
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 105.991(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.2034(7)
_cell_length_b                   5.0614(2)
_cell_length_c                   27.5987(12)
_cell_measurement_reflns_used    15460
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.1740
_cell_measurement_theta_min      4.2860
_cell_volume                     2847.3(2)
_computing_cell_refinement       'CrysAlisPro [1]'
_computing_data_collection       'CrysAlisPro [1]'
_computing_data_reduction        'CrysAlisPro [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [3]'
_computing_structure_solution    'SHELXT 2014/5 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 5.2558
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0625
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            34319
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.911
_diffrn_reflns_theta_min         3.332
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    2.071
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.871
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.397
_exptl_crystal_description       prism
_exptl_crystal_F_000             1256
_exptl_crystal_size_max          0.159
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.057
_refine_diff_density_max         0.431
_refine_diff_density_min         -0.484
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2996
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0431
_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)+(0.0698P)²+3.0892P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1246
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2795
_reflns_number_total             2996
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0488_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               8105954
_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_min   0.734
_shelx_estimated_absorpt_t_max   0.891
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'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
S1 S 0.70397(2) 1.25411(8) 0.47699(2) 0.02786(16) Uani 1 1 d . . . . .
O1 O 0.61712(6) 0.3255(3) 0.30000(5) 0.0291(3) Uani 1 1 d D . . . .
H1O H 0.6164(12) 0.211(4) 0.2777(7) 0.044 Uiso 1 1 d D U . . .
O2 O 0.72569(6) 0.2874(3) 0.31164(5) 0.0329(3) Uani 1 1 d . . . . .
N1 N 0.60383(7) -0.4412(3) 0.73461(5) 0.0272(3) Uani 1 1 d . . . . .
N2 N 0.52646(7) 0.1957(3) 0.59005(6) 0.0306(3) Uani 1 1 d . . . . .
C1 C 0.70173(8) 0.9950(3) 0.43315(6) 0.0242(3) Uani 1 1 d . . . . .
C2 C 0.63918(8) 0.9125(3) 0.40682(6) 0.0259(3) Uani 1 1 d . . . . .
H2 H 0.601792 0.989443 0.413862 0.031 Uiso 1 1 calc R U . . .
C3 C 0.63136(8) 0.7185(3) 0.37037(7) 0.0263(4) Uani 1 1 d . . . . .
H3 H 0.588525 0.663798 0.352179 0.032 Uiso 1 1 calc R U . . .
C4 C 0.68600(8) 0.6026(3) 0.36015(6) 0.0237(3) Uani 1 1 d . . . . .
C5 C 0.74839(8) 0.6844(4) 0.38727(7) 0.0284(4) Uani 1 1 d . . . . .
H5 H 0.785844 0.604956 0.380784 0.034 Uiso 1 1 calc R U . . .
C6 C 0.75666(8) 0.8798(4) 0.42354(7) 0.0291(4) Uani 1 1 d . . . . .
H6 H 0.799465 0.934929 0.441734 0.035 Uiso 1 1 calc R U . . .
C7 C 0.67887(8) 0.3894(3) 0.32177(6) 0.0250(3) Uani 1 1 d . . . . .
C8 C 0.54347(8) -0.3588(4) 0.70955(7) 0.0278(4) Uani 1 1 d . . . . .
H8 H 0.506677 -0.441202 0.716538 0.033 Uiso 1 1 calc R U . . .
C9 C 0.53257(8) -0.1595(4) 0.67407(7) 0.0277(4) Uani 1 1 d . . . . .
H9 H 0.489132 -0.109413 0.656416 0.033 Uiso 1 1 calc R U . . .
C10 C 0.58639(8) -0.0326(3) 0.66453(6) 0.0263(4) Uani 1 1 d . . . . .
C11 C 0.64912(8) -0.1116(4) 0.69167(7) 0.0296(4) Uani 1 1 d . . . . .
H11 H 0.686848 -0.024814 0.687188 0.035 Uiso 1 1 calc R U . . .
C12 C 0.65532(8) -0.3200(4) 0.72544(7) 0.0301(4) Uani 1 1 d . . . . .
H12 H 0.698118 -0.379035 0.742789 0.036 Uiso 1 1 calc R U . . .
C13 C 0.57796(9) 0.1793(4) 0.62631(7) 0.0297(4) Uani 1 1 d . . . . .
H13 H 0.611930 0.305537 0.629081 0.036 Uiso 1 1 calc R U . . .
C14 C 0.52312(9) 0.4082(4) 0.55304(7) 0.0319(4) Uani 1 1 d . . . . .
H14 H 0.546158 0.568047 0.570713 0.038 Uiso 1 1 calc R U . . .
C15 C 0.55623(10) 0.3195(4) 0.51338(8) 0.0380(5) Uani 1 1 d . . . . .
H15A H 0.536724 0.150136 0.498537 0.046 Uiso 1 1 calc R U . . .
H15B H 0.603466 0.289115 0.529606 0.046 Uiso 1 1 calc R U . . .
C16 C 0.54863(9) 0.5243(4) 0.47160(8) 0.0370(4) Uani 1 1 d . . . . .
H16A H 0.568568 0.455127 0.445665 0.044 Uiso 1 1 calc R U . . .
H16B H 0.572529 0.687005 0.485848 0.044 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'
S S 0.3331 0.5567 '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
C1 S1 S1 105.60(6) . 2_656
C7 O1 H1O 108.4(17) . .
C12 N1 C8 118.21(15) . .
C13 N2 C14 117.61(16) . .
C2 C1 C6 120.21(16) . .
C2 C1 S1 114.87(12) . .
C6 C1 S1 124.91(13) . .
C3 C2 C1 119.97(15) . .
C3 C2 H2 120.0 . .
C1 C2 H2 120.0 . .
C2 C3 C4 120.40(15) . .
C2 C3 H3 119.8 . .
C4 C3 H3 119.8 . .
C5 C4 C3 119.06(16) . .
C5 C4 C7 119.54(15) . .
C3 C4 C7 121.39(15) . .
C6 C5 C4 120.93(16) . .
C6 C5 H5 119.5 . .
C4 C5 H5 119.5 . .
C5 C6 C1 119.43(15) . .
C5 C6 H6 120.3 . .
C1 C6 H6 120.3 . .
O2 C7 O1 124.08(16) . .
O2 C7 C4 122.71(15) . .
O1 C7 C4 113.21(14) . .
N1 C8 C9 122.82(16) . .
N1 C8 H8 118.6 . .
C9 C8 H8 118.6 . .
C8 C9 C10 118.96(15) . .
C8 C9 H9 120.5 . .
C10 C9 H9 120.5 . .
C11 C10 C9 118.38(16) . .
C11 C10 C13 120.07(15) . .
C9 C10 C13 121.55(15) . .
C12 C11 C10 118.57(16) . .
C12 C11 H11 120.7 . .
C10 C11 H11 120.7 . .
N1 C12 C11 122.98(16) . .
N1 C12 H12 118.5 . .
C11 C12 H12 118.5 . .
N2 C13 C10 121.34(17) . .
N2 C13 H13 119.3 . .
C10 C13 H13 119.3 . .
N2 C14 C15 109.88(15) . .
N2 C14 C16 108.97(15) . 5_666
C15 C14 C16 110.29(16) . 5_666
N2 C14 H14 109.2 . .
C15 C14 H14 109.2 . .
C16 C14 H14 109.2 5_666 .
C14 C15 C16 111.69(16) . .
C14 C15 H15A 109.3 . .
C16 C15 H15A 109.3 . .
C14 C15 H15B 109.3 . .
C16 C15 H15B 109.3 . .
H15A C15 H15B 107.9 . .
C15 C16 C14 111.97(15) . 5_666
C15 C16 H16A 109.2 . .
C14 C16 H16A 109.2 5_666 .
C15 C16 H16B 109.2 . .
C14 C16 H16B 109.2 5_666 .
H16A C16 H16B 107.9 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.7762(17) .
S1 S1 2.0142(9) 2_656
O1 C7 1.321(2) .
O1 H1O 0.843(10) .
O2 C7 1.218(2) .
N1 C12 1.336(2) .
N1 C8 1.343(2) .
N2 C13 1.264(2) .
N2 C14 1.471(2) .
C1 C2 1.389(2) .
C1 C6 1.392(2) .
C2 C3 1.383(2) .
C2 H2 0.9500 .
C3 C4 1.395(2) .
C3 H3 0.9500 .
C4 C5 1.391(2) .
C4 C7 1.491(2) .
C5 C6 1.384(3) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C8 C9 1.380(2) .
C8 H8 0.9500 .
C9 C10 1.396(2) .
C9 H9 0.9500 .
C10 C11 1.393(2) .
C10 C13 1.480(2) .
C11 C12 1.390(3) .
C11 H11 0.9500 .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 C15 1.522(3) .
C14 C16 1.525(3) 5_666
C14 H14 1.0000 .
C15 C16 1.526(3) .
C15 H15A 0.9900 .
C15 H15B 0.9900 .
C16 H16A 0.9900 .
C16 H16B 0.9900 .
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
S1 S1 C1 C2 163.16(12) 2_656 . . .
S1 S1 C1 C6 -18.19(16) 2_656 . . .
C6 C1 C2 C3 -1.1(3) . . . .
S1 C1 C2 C3 177.67(13) . . . .
C1 C2 C3 C4 0.7(3) . . . .
C2 C3 C4 C5 0.2(3) . . . .
C2 C3 C4 C7 178.75(15) . . . .
C3 C4 C5 C6 -0.7(3) . . . .
C7 C4 C5 C6 -179.27(16) . . . .
C4 C5 C6 C1 0.3(3) . . . .
C2 C1 C6 C5 0.6(3) . . . .
S1 C1 C6 C5 -178.02(14) . . . .
C5 C4 C7 O2 -2.5(3) . . . .
C3 C4 C7 O2 178.98(17) . . . .
C5 C4 C7 O1 178.00(16) . . . .
C3 C4 C7 O1 -0.5(2) . . . .
C12 N1 C8 C9 1.6(3) . . . .
N1 C8 C9 C10 -1.7(3) . . . .
C8 C9 C10 C11 -0.5(3) . . . .
C8 C9 C10 C13 178.90(17) . . . .
C9 C10 C11 C12 2.6(3) . . . .
C13 C10 C11 C12 -176.80(17) . . . .
C8 N1 C12 C11 0.7(3) . . . .
C10 C11 C12 N1 -2.8(3) . . . .
C14 N2 C13 C10 -178.29(16) . . . .
C11 C10 C13 N2 155.41(18) . . . .
C9 C10 C13 N2 -24.0(3) . . . .
C13 N2 C14 C15 84.7(2) . . . .
C13 N2 C14 C16 -154.33(18) . . . 5_666
N2 C14 C15 C16 174.94(16) . . . .
C16 C14 C15 C16 54.8(3) 5_666 . . .
C14 C15 C16 C14 -55.7(3) . . . 5_666
