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#$Date: 2022-11-22 12:39:48 +0200 (Tue, 22 Nov 2022) $
#$Revision: 279464 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106201.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_8106201
loop_
_publ_author_name
'Yeo, Chien Ing'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of N-(2-chlorophenyl)methoxycarbothioamide, C8H8ClNOS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              517
_journal_page_last               518
_journal_paper_doi               10.1515/ncrs-2017-0409
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C8 H8 Cl N O S'
_chemical_formula_sum            'C8 H8 Cl N O S'
_chemical_formula_weight         201.66
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                66.279(12)
_cell_angle_beta                 72.245(9)
_cell_angle_gamma                87.699(8)
_cell_formula_units_Z            2
_cell_length_a                   6.7658(5)
_cell_length_b                   8.0344(10)
_cell_length_c                   9.6285(12)
_cell_measurement_reflns_used    2208
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.9953
_cell_measurement_theta_min      2.4301
_cell_volume                     454.31(10)
_computing_cell_refinement       'CrysAlis PRO [1]'
_computing_data_collection       'CrysAlis PRO [1]'
_computing_data_reduction        'CrysAlis PRO [1]'
_computing_molecular_graphics    'ORTEP-3 for Windows [4]'
_computing_publication_material  'SHELXL-2014/7 [3]'
_computing_structure_refinement  'SHELXL-2014/7 [3]'
_computing_structure_solution    'SHELXS-97 [2]'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4041
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
'Agilent Technologies SuperNova Dual diffractometer with Atlas detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  Mirror
_diffrn_radiation_source         'SuperNova (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3419
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.049
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_min         2.435
_exptl_absorpt_coefficient_mu    0.598
_exptl_absorpt_correction_T_max  0.9156
_exptl_absorpt_correction_T_min  0.8648
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.910
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     113
_refine_ls_number_reflns         1612
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0555
_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)+(0.1126P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1472
_refine_ls_wR_factor_ref         0.1577
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1412
_reflns_number_total             1612
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0409_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8106201
_shelx_shelxl_version_number     2014/7
_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   0.865
_shelx_estimated_absorpt_t_max   0.916
loop_
_space_group_symop_operation_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_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
Cl1 Cl 0.74319(9) 0.15138(8) 0.31896(8) 0.0279(3) Uani 1 1 d . . . . .
S1 S 0.20199(10) 0.36917(9) 0.67712(7) 0.0257(3) Uani 1 1 d . . . . .
O1 O 0.0511(3) 0.2195(2) 0.52448(19) 0.0214(5) Uani 1 1 d . . . . .
N1 N 0.3755(3) 0.3487(3) 0.3994(2) 0.0206(5) Uani 1 1 d D . . . .
H1N H 0.482(3) 0.408(3) 0.399(3) 0.025 Uiso 1 1 d D U . . .
C1 C 0.2063(4) 0.3101(3) 0.5286(3) 0.0187(6) Uani 1 1 d . . . . .
C2 C 0.3925(4) 0.3038(3) 0.2674(3) 0.0190(6) Uani 1 1 d . . . . .
C3 C 0.5623(4) 0.2137(3) 0.2164(3) 0.0204(6) Uani 1 1 d . . . . .
C4 C 0.5892(4) 0.1769(3) 0.0841(3) 0.0243(6) Uani 1 1 d . . . . .
H4 H 0.7059 0.1172 0.0497 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4467(4) 0.2268(3) 0.0020(3) 0.0248(6) Uani 1 1 d . . . . .
H5 H 0.4644 0.2010 -0.0889 0.030 Uiso 1 1 calc R U . . .
C6 C 0.2763(4) 0.3155(3) 0.0527(3) 0.0252(6) Uani 1 1 d . . . . .
H6 H 0.1769 0.3488 -0.0030 0.030 Uiso 1 1 calc R U . . .
C7 C 0.2518(4) 0.3548(3) 0.1830(3) 0.0222(6) Uani 1 1 d . . . . .
H7 H 0.1370 0.4176 0.2153 0.027 Uiso 1 1 calc R U . . .
C8 C -0.1426(4) 0.1699(4) 0.6562(3) 0.0270(6) Uani 1 1 d . . . . .
H8A H -0.2418 0.1017 0.6381 0.040 Uiso 1 1 calc R U . . .
H8B H -0.2012 0.2808 0.6633 0.040 Uiso 1 1 calc R U . . .
H8C H -0.1155 0.0938 0.7563 0.040 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'
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
C1 O1 C8 118.53(18) . .
C1 N1 C2 125.8(2) . .
C1 N1 H1N 114.7(17) . .
C2 N1 H1N 119.6(17) . .
O1 C1 N1 112.6(2) . .
O1 C1 S1 125.27(18) . .
N1 C1 S1 122.1(2) . .
C7 C2 C3 118.7(2) . .
C7 C2 N1 121.9(2) . .
C3 C2 N1 119.3(2) . .
C4 C3 C2 120.7(2) . .
C4 C3 Cl1 119.75(18) . .
C2 C3 Cl1 119.52(18) . .
C5 C4 C3 120.0(2) . .
C5 C4 H4 120.0 . .
C3 C4 H4 120.0 . .
C4 C5 C6 119.7(2) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C7 C6 C5 120.2(2) . .
C7 C6 H6 119.9 . .
C5 C6 H6 119.9 . .
C6 C7 C2 120.6(2) . .
C6 C7 H7 119.7 . .
C2 C7 H7 119.7 . .
O1 C8 H8A 109.5 . .
O1 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
O1 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C3 1.736(3) .
S1 C1 1.671(2) .
O1 C1 1.321(3) .
O1 C8 1.451(3) .
N1 C1 1.343(3) .
N1 C2 1.426(3) .
N1 H1N 0.875(10) .
C2 C7 1.381(4) .
C2 C3 1.400(3) .
C3 C4 1.378(3) .
C4 C5 1.376(4) .
C4 H4 0.9500 .
C5 C6 1.395(3) .
C5 H5 0.9500 .
C6 C7 1.374(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 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
C8 O1 C1 N1 -179.52(19) . . . .
C8 O1 C1 S1 1.8(3) . . . .
C2 N1 C1 O1 1.4(3) . . . .
C2 N1 C1 S1 -179.88(17) . . . .
C1 N1 C2 C7 54.3(3) . . . .
C1 N1 C2 C3 -129.1(3) . . . .
C7 C2 C3 C4 0.2(4) . . . .
N1 C2 C3 C4 -176.6(2) . . . .
C7 C2 C3 Cl1 179.06(19) . . . .
N1 C2 C3 Cl1 2.3(3) . . . .
C2 C3 C4 C5 -0.8(4) . . . .
Cl1 C3 C4 C5 -179.70(19) . . . .
C3 C4 C5 C6 0.4(4) . . . .
C4 C5 C6 C7 0.7(4) . . . .
C5 C6 C7 C2 -1.4(4) . . . .
C3 C2 C7 C6 0.9(4) . . . .
N1 C2 C7 C6 177.6(2) . . . .
