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#$Date: 2025-08-20 19:06:18 +0300 (Wed, 20 Aug 2025) $
#$Revision: 301834 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/71/4127142.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_4127142
loop_
_publ_author_name
'Paul, Mithun'
'Chakraborty, Shaunak'
'Desiraju, Gautam R.'
_publ_section_title
;
 Six-component Molecular Solids, ABC[D1-(x+y)ExFy]2.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b12501
_journal_year                    2018
_chemical_formula_moiety         'C8 H6 S2, C8 H12 N2, 2(C6 H5 Cl O2)'
_chemical_formula_sum            'C28 H28 Cl2 N2 O4 S2'
_chemical_formula_weight         591.54
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 134.41(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.082(9)
_cell_length_b                   21.71(2)
_cell_length_c                   11.352(9)
_cell_measurement_reflns_used    3510
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      33.7
_cell_measurement_theta_min      2.7
_cell_volume                     1423(3)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  CCD
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0790
_diffrn_reflns_av_unetI/netI     0.0470
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14613
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.876
_exptl_absorpt_coefficient_mu    0.412
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.640
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0995
_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)+(0.1079P)²+3.8292P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2777
_refine_ls_wR_factor_ref         0.2876
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2682
_reflns_number_total             3261
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja7b12501_si_003.cif
_cod_data_source_block           T2
_cod_database_code               4127142
_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   0.779
_shelx_estimated_absorpt_t_max   0.941
_shelxl_version_number           2013-2
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
S1 S 0.1363(4) -0.00569(9) -0.2501(3) 0.0862(6) Uani 1 1 d . .
C11 C 0.1702(14) -0.0813(4) -0.1971(11) 0.088(2) Uani 1 1 d . .
H11 H 0.2253 -0.0953 -0.0975 0.106 Uiso 1 1 calc R U
C12 C 0.1066(15) -0.1182(4) -0.3189(11) 0.092(2) Uani 1 1 d . .
H12 H 0.1152 -0.1609 -0.3101 0.110 Uiso 1 1 calc R U
C13 C 0.0255(12) -0.0872(3) -0.4615(10) 0.0783(19) Uani 1 1 d . .
H13 H -0.0259 -0.1067 -0.5552 0.094 Uiso 1 1 calc R U
C14 C 0.0331(10) -0.0237(3) -0.4425(8) 0.0662(16) Uani 1 1 d . .
N1 N -0.5465(7) -0.04835(18) -0.5987(5) 0.0467(9) Uani 1 1 d . .
C7 C -0.6701(11) 0.0204(3) -0.8183(7) 0.0674(15) Uani 1 1 d . .
H7A H -0.6798 -0.0184 -0.8634 0.101 Uiso 1 1 calc R U
H7B H -0.5675 0.0473 -0.8093 0.101 Uiso 1 1 calc R U
H7C H -0.8213 0.0387 -0.8895 0.101 Uiso 1 1 calc R U
C8 C -0.5791(8) 0.0104(2) -0.6507(6) 0.0451(10) Uani 1 1 d . .
C9 C -0.4676(8) -0.0595(2) -0.4512(6) 0.0471(11) Uani 1 1 d . .
C10 C -0.4364(12) -0.1264(3) -0.4011(8) 0.0705(16) Uani 1 1 d . .
H10A H -0.5663 -0.1499 -0.4933 0.106 Uiso 1 1 calc R U
H10B H -0.4266 -0.1295 -0.3120 0.106 Uiso 1 1 calc R U
H10C H -0.2967 -0.1421 -0.3661 0.106 Uiso 1 1 calc R U
Cl1 Cl 0.1752(2) -0.25421(7) -0.5369(2) 0.0653(5) Uani 1 1 d . .
O1 O 0.3223(6) -0.35505(17) -0.3098(5) 0.0586(10) Uani 1 1 d . .
H1 H 0.3512 -0.3857 -0.2558 0.088 Uiso 1 1 d R U
O2 O -0.2721(7) -0.21071(18) -0.6812(5) 0.0660(11) Uani 1 1 d . .
H2 H -0.4123 -0.2065 -0.7428 0.099 Uiso 1 1 d R U
C1 C 0.0200(8) -0.2839(2) -0.4965(6) 0.0429(10) Uani 1 1 d . .
C2 C 0.1092(8) -0.3334(2) -0.3866(6) 0.0454(10) Uani 1 1 d . .
C3 C -0.0235(9) -0.3576(2) -0.3598(7) 0.0561(13) Uani 1 1 d . .
H3 H 0.0331 -0.3900 -0.2866 0.067 Uiso 1 1 calc R U
C4 C -0.2357(10) -0.3330(3) -0.4419(7) 0.0586(13) Uani 1 1 d . .
H4 H -0.3225 -0.3497 -0.4239 0.070 Uiso 1 1 calc R U
C5 C -0.3278(10) -0.2842(3) -0.5510(7) 0.0567(13) Uani 1 1 d . .
H5 H -0.4731 -0.2684 -0.6051 0.068 Uiso 1 1 calc R U
C6 C -0.1980(9) -0.2594(2) -0.5778(6) 0.0496(11) Uani 1 1 d . .
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'
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
C11 S1 C14 92.5(4) . .
C12 C11 S1 111.0(7) . .
C12 C11 H11 124.5 . .
S1 C11 H11 124.5 . .
C11 C12 C13 115.2(7) . .
C11 C12 H12 122.4 . .
C13 C12 H12 122.4 . .
C14 C13 C12 111.0(7) . .
C14 C13 H13 124.5 . .
C12 C13 H13 124.5 . .
C13 C14 C14 128.3(8) . 3_554
C13 C14 S1 110.2(6) . .
C14 C14 S1 121.4(6) 3_554 .
C9 N1 C8 119.7(4) . .
C8 C7 H7A 109.5 . .
C8 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C8 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
N1 C8 C9 119.7(4) . 3_454
N1 C8 C7 117.6(5) . .
C9 C8 C7 122.7(5) 3_454 .
N1 C9 C8 120.6(4) . 3_454
N1 C9 C10 117.0(5) . .
C8 C9 C10 122.4(5) 3_454 .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C2 O1 H1 109.3 . .
C6 O2 H2 109.4 . .
C6 C1 C2 120.2(4) . .
C6 C1 Cl1 119.6(4) . .
C2 C1 Cl1 120.2(4) . .
O1 C2 C3 123.3(4) . .
O1 C2 C1 117.8(4) . .
C3 C2 C1 118.9(5) . .
C4 C3 C2 119.5(5) . .
C4 C3 H3 120.3 . .
C2 C3 H3 120.3 . .
C3 C4 C5 122.8(5) . .
C3 C4 H4 118.6 . .
C5 C4 H4 118.6 . .
C4 C5 C6 118.5(5) . .
C4 C5 H5 120.8 . .
C6 C5 H5 120.8 . .
O2 C6 C5 122.9(5) . .
O2 C6 C1 116.9(5) . .
C5 C6 C1 120.2(5) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C11 1.703(9) .
S1 C14 1.752(7) .
C11 C12 1.350(11) .
C11 H11 0.9300 .
C12 C13 1.421(11) .
C12 H12 0.9300 .
C13 C14 1.389(9) .
C13 H13 0.9300 .
C14 C14 1.440(14) 3_554
N1 C9 1.332(7) .
N1 C8 1.351(6) .
C7 C8 1.501(7) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 C9 1.416(7) 3_454
C9 C8 1.416(7) 3_454
C9 C10 1.515(7) .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
Cl1 C1 1.732(5) .
O1 C2 1.358(6) .
O1 H1 0.8200 .
O2 C6 1.367(6) .
O2 H2 0.8200 .
C1 C6 1.401(7) .
C1 C2 1.405(6) .
C2 C3 1.405(7) .
C3 C4 1.363(8) .
C3 H3 0.9300 .
C4 C5 1.386(8) .
C4 H4 0.9300 .
C5 C6 1.389(8) .
C5 H5 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_4
C14 S1 C11 C12 0.0(7) .
S1 C11 C12 C13 -0.5(10) .
C11 C12 C13 C14 0.9(10) .
C12 C13 C14 C14 179.9(8) 3_554
C12 C13 C14 S1 -0.9(8) .
C11 S1 C14 C13 0.5(5) .
C11 S1 C14 C14 179.8(7) 3_554
C9 N1 C8 C9 -0.9(8) 3_454
C9 N1 C8 C7 -179.5(5) .
C8 N1 C9 C8 0.9(8) 3_454
C8 N1 C9 C10 179.6(5) .
C6 C1 C2 O1 -179.3(4) .
Cl1 C1 C2 O1 2.6(6) .
C6 C1 C2 C3 -0.2(7) .
Cl1 C1 C2 C3 -178.3(4) .
O1 C2 C3 C4 179.8(5) .
C1 C2 C3 C4 0.8(8) .
C2 C3 C4 C5 -0.7(9) .
C3 C4 C5 C6 0.1(8) .
C4 C5 C6 O2 -179.1(5) .
C4 C5 C6 C1 0.5(8) .
C2 C1 C6 O2 179.2(4) .
Cl1 C1 C6 O2 -2.7(6) .
C2 C1 C6 C5 -0.4(7) .
Cl1 C1 C6 C5 177.7(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139125973
