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#$Date: 2023-03-07 12:06:44 +0200 (Tue, 07 Mar 2023) $
#$Revision: 281698 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106863.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_8106863
loop_
_publ_author_name
'Barakat, Assem'
'Ghabbour, Hazem A.'
'Al-Majid, Abdullah Mohammed'
'Said, Mohamed M.'
'El Tamany, El Sayed H.'
'Fun, Hoong-Kun'
_publ_section_title
;
 Crystal structure of
 (Z)-5-(4-chlorobenzylidene)-2-thioxothiazolidin-4-one
 ---dimethylsulfoxide (1:1), C12H12ClNO2S3
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              319
_journal_page_last               320
_journal_paper_doi               10.1515/ncrs-2015-0167
_journal_volume                  231
_journal_year                    2016
_chemical_formula_sum            'C12 H12 Cl N O2 S3'
_chemical_formula_weight         333.86
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                91.807(6)
_cell_angle_beta                 96.032(6)
_cell_angle_gamma                96.667(6)
_cell_formula_units_Z            2
_cell_length_a                   4.4065(7)
_cell_length_b                   12.326(2)
_cell_length_c                   13.399(2)
_cell_measurement_reflns_used    9937
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.82
_cell_measurement_theta_min      2.21
_cell_volume                     718.1(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II D8 venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus micro tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3288
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        .
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.697
_exptl_absorpt_correction_T_max  0.8818
_exptl_absorpt_correction_T_min  0.6458
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADAB_Bruker_2014
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.812
_refine_diff_density_min         -0.644
_refine_diff_density_rms         0.147
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.160
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3288
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.160
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0668
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0301P)²+4.4276P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1605
_refine_ls_wR_factor_ref         0.1644
_reflns_number_gt                2867
_reflns_number_total             3288
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2015-0167_suppl.cif
_cod_data_source_block           t
_cod_original_cell_volume        718.2(2)
_cod_database_code               8106863
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.9984(3) 0.04988(10) 0.88059(8) 0.0203(3) Uani 1 1 d . . .
S1 S 0.6844(3) 0.54615(9) 0.29865(9) 0.0186(3) Uani 1 1 d . . .
S2 S 0.6614(3) 0.38124(9) 0.45512(8) 0.0115(3) Uani 1 1 d . . .
O1 O 0.0026(8) 0.1959(3) 0.3025(3) 0.0193(8) Uani 1 1 d . . .
N1 N 0.3073(9) 0.3584(3) 0.2890(3) 0.0120(8) Uani 1 1 d . . .
C1 C 0.5345(11) 0.4295(4) 0.3379(3) 0.0120(9) Uani 1 1 d . . .
C2 C 0.2088(11) 0.2641(4) 0.3373(3) 0.0121(9) Uani 1 1 d . . .
C3 C 0.4010(10) 0.2622(3) 0.4359(3) 0.0099(8) Uani 1 1 d . . .
C4 C 0.3582(11) 0.1752(4) 0.4936(3) 0.0115(9) Uani 1 1 d . . .
H4A H 0.1952 0.1212 0.4677 0.014 Uiso 1 1 calc R . .
C5 C 0.5194(11) 0.1504(4) 0.5887(3) 0.0121(9) Uani 1 1 d . . .
C6 C 0.4322(11) 0.0487(4) 0.6283(3) 0.0151(9) Uani 1 1 d . . .
H6A H 0.2706 0.0002 0.5928 0.018 Uiso 1 1 calc R . .
C7 C 0.5760(12) 0.0175(4) 0.7176(3) 0.0166(10) Uani 1 1 d . . .
H7A H 0.5143 -0.0515 0.7435 0.020 Uiso 1 1 calc R . .
C8 C 0.8111(12) 0.0885(4) 0.7686(3) 0.0148(9) Uani 1 1 d . . .
C9 C 0.9034(12) 0.1899(4) 0.7325(3) 0.0148(9) Uani 1 1 d . . .
H9A H 1.0655 0.2377 0.7685 0.018 Uiso 1 1 calc R . .
C10 C 0.7557(11) 0.2207(4) 0.6427(3) 0.0148(9) Uani 1 1 d . . .
H10A H 0.8163 0.2903 0.6179 0.018 Uiso 1 1 calc R . .
S3 S -0.2935(3) 0.35019(9) 0.07676(8) 0.0097(2) Uani 1 1 d . . .
O2 O 0.0564(8) 0.3619(3) 0.0906(2) 0.0150(7) Uani 1 1 d . . .
C11 C -0.4121(12) 0.2065(4) 0.0754(4) 0.0171(10) Uani 1 1 d . . .
H11A H -0.3365 0.1776 0.1394 0.026 Uiso 1 1 calc R . .
H11B H -0.3279 0.1700 0.0203 0.026 Uiso 1 1 calc R . .
H11C H -0.6371 0.1931 0.0657 0.026 Uiso 1 1 calc R . .
C12 C -0.3925(11) 0.3714(4) -0.0535(3) 0.0159(10) Uani 1 1 d . . .
H12A H -0.3124 0.4458 -0.0687 0.024 Uiso 1 1 calc R . .
H12B H -0.6167 0.3612 -0.0688 0.024 Uiso 1 1 calc R . .
H12C H -0.3028 0.3187 -0.0944 0.024 Uiso 1 1 calc R . .
H1N1 H 0.224(14) 0.368(5) 0.233(4) 0.016(14) Uiso 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'
S S 0.1246 0.1234 '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'
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
C3 S2 C1 92.1(2) . .
C1 N1 C2 117.9(4) . .
C1 N1 H1N1 124(4) . .
C2 N1 H1N1 118(4) . .
N1 C1 S1 127.3(4) . .
N1 C1 S2 110.9(3) . .
S1 C1 S2 121.9(3) . .
O1 C2 N1 124.1(4) . .
O1 C2 C3 126.9(4) . .
N1 C2 C3 109.0(4) . .
C4 C3 C2 119.6(4) . .
C4 C3 S2 130.4(3) . .
C2 C3 S2 110.0(3) . .
C3 C4 C5 130.8(4) . .
C3 C4 H4A 114.6 . .
C5 C4 H4A 114.6 . .
C10 C5 C6 118.1(4) . .
C10 C5 C4 124.3(4) . .
C6 C5 C4 117.6(4) . .
C7 C6 C5 121.6(4) . .
C7 C6 H6A 119.2 . .
C5 C6 H6A 119.2 . .
C6 C7 C8 118.8(4) . .
C6 C7 H7A 120.6 . .
C8 C7 H7A 120.6 . .
C7 C8 C9 121.5(4) . .
C7 C8 Cl1 119.4(4) . .
C9 C8 Cl1 119.0(4) . .
C8 C9 C10 119.2(4) . .
C8 C9 H9A 120.4 . .
C10 C9 H9A 120.4 . .
C9 C10 C5 120.8(4) . .
C9 C10 H10A 119.6 . .
C5 C10 H10A 119.6 . .
O2 S3 C11 105.2(2) . .
O2 S3 C12 104.9(2) . .
C11 S3 C12 98.4(2) . .
S3 C11 H11A 109.5 . .
S3 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
S3 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
S3 C12 H12A 109.5 . .
S3 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
S3 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C8 1.742(5) .
S1 C1 1.637(5) .
S2 C3 1.749(4) .
S2 C1 1.757(5) .
O1 C2 1.208(6) .
N1 C1 1.350(6) .
N1 C2 1.396(6) .
N1 H1N1 0.82(6) .
C2 C3 1.494(6) .
C3 C4 1.349(6) .
C4 C5 1.451(6) .
C4 H4A 0.9500 .
C5 C10 1.397(6) .
C5 C6 1.405(6) .
C6 C7 1.382(7) .
C6 H6A 0.9500 .
C7 C8 1.382(7) .
C7 H7A 0.9500 .
C8 C9 1.387(6) .
C9 C10 1.391(6) .
C9 H9A 0.9500 .
C10 H10A 0.9500 .
S3 O2 1.523(3) .
S3 C11 1.787(5) .
S3 C12 1.789(5) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
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
C2 N1 C1 S1 -178.6(4) . . . .
C2 N1 C1 S2 1.4(5) . . . .
C3 S2 C1 N1 0.3(4) . . . .
C3 S2 C1 S1 -179.6(3) . . . .
C1 N1 C2 O1 178.0(4) . . . .
C1 N1 C2 C3 -2.7(6) . . . .
O1 C2 C3 C4 2.8(7) . . . .
N1 C2 C3 C4 -176.4(4) . . . .
O1 C2 C3 S2 -178.0(4) . . . .
N1 C2 C3 S2 2.7(5) . . . .
C1 S2 C3 C4 177.3(5) . . . .
C1 S2 C3 C2 -1.8(3) . . . .
C2 C3 C4 C5 176.8(5) . . . .
S2 C3 C4 C5 -2.1(8) . . . .
C3 C4 C5 C10 3.4(8) . . . .
C3 C4 C5 C6 -176.3(5) . . . .
C10 C5 C6 C7 -0.6(7) . . . .
C4 C5 C6 C7 179.1(4) . . . .
C5 C6 C7 C8 -0.1(7) . . . .
C6 C7 C8 C9 0.4(7) . . . .
C6 C7 C8 Cl1 -179.2(4) . . . .
C7 C8 C9 C10 0.0(7) . . . .
Cl1 C8 C9 C10 179.6(4) . . . .
C8 C9 C10 C5 -0.7(7) . . . .
C6 C5 C10 C9 1.0(7) . . . .
C4 C5 C10 C9 -178.7(5) . . . .
