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#$Date: 2022-09-16 12:39:42 +0300 (Fri, 16 Sep 2022) $
#$Revision: 277924 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/57/8105789.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_8105789
loop_
_publ_author_name
'Yeo, Chien Ing'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of N-(2-methylphenyl)(propan-2-yloxy)carbothioamide,
 C11H15NOS
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              589
_journal_page_last               591
_journal_paper_doi               10.1515/ncrs-2019-0045
_journal_volume                  234
_journal_year                    2019
_chemical_formula_moiety         'C11 H15 N O S'
_chemical_formula_sum            'C11 H15 N O S'
_chemical_formula_weight         209.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90.999(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.3979(4)
_cell_length_b                   8.5384(4)
_cell_length_c                   18.2771(10)
_cell_measurement_reflns_used    2602
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.85
_cell_measurement_theta_min      2.63
_cell_volume                     1154.32(10)
_computing_cell_refinement       'APEX2 [2]'
_computing_data_collection       'APEX2 [2]'
_computing_data_reduction        'SAINT [2]'
_computing_molecular_graphics    'ORTEP-3 for Windows [5]'
_computing_publication_material  'SHELXL-2014/7 [4]'
_computing_structure_refinement  'SHELXL-2014/7 [4]'
_computing_structure_solution    'SHELXS-97 [3]'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0582
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            10515
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        27.500
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_min         2.633
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5782
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     133
_refine_ls_number_reflns         2649
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0409
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0568P)²+0.2832P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1015
_refine_ls_wR_factor_ref         0.1093
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2186
_reflns_number_total             2649
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0045_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105789
_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   0.936
_shelx_estimated_absorpt_t_max   0.973
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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 0.31646(5) 0.92776(5) 1.08505(2) 0.02241(14) Uani 1 1 d . . . . .
O1 O 0.08168(14) 0.74832(13) 1.00997(6) 0.0207(3) Uani 1 1 d . . . . .
N1 N 0.30848(17) 0.84343(16) 0.94626(7) 0.0204(3) Uani 1 1 d D . . . .
H1N H 0.4082(17) 0.8953(19) 0.9436(10) 0.025 Uiso 1 1 d D U . . .
C1 C 0.23022(19) 0.83559(18) 1.01114(8) 0.0184(3) Uani 1 1 d . . . . .
C2 C 0.2401(2) 0.78416(18) 0.87761(8) 0.0183(3) Uani 1 1 d . . . . .
C3 C 0.3557(2) 0.69622(19) 0.83442(9) 0.0233(4) Uani 1 1 d . . . . .
C4 C 0.2909(3) 0.6479(2) 0.76591(10) 0.0311(4) Uani 1 1 d . . . . .
H4 H 0.3679 0.5893 0.7351 0.037 Uiso 1 1 calc R U . . .
C5 C 0.1177(3) 0.6831(2) 0.74184(9) 0.0340(4) Uani 1 1 d . . . . .
H5 H 0.0767 0.6491 0.6949 0.041 Uiso 1 1 calc R U . . .
C6 C 0.0044(2) 0.7679(2) 0.78616(10) 0.0312(4) Uani 1 1 d . . . . .
H6 H -0.1154 0.7909 0.7700 0.037 Uiso 1 1 calc R U . . .
C7 C 0.0651(2) 0.81951(19) 0.85417(9) 0.0228(3) Uani 1 1 d . . . . .
H7 H -0.0123 0.8787 0.8845 0.027 Uiso 1 1 calc R U . . .
C8 C 0.5424(2) 0.6509(2) 0.86049(11) 0.0352(4) Uani 1 1 d . . . . .
H8A H 0.5997 0.5855 0.8234 0.053 Uiso 1 1 calc R U . . .
H8B H 0.5343 0.5922 0.9064 0.053 Uiso 1 1 calc R U . . .
H8C H 0.6149 0.7456 0.8687 0.053 Uiso 1 1 calc R U . . .
C9 C -0.0271(2) 0.73030(19) 1.07634(8) 0.0209(3) Uani 1 1 d . . . . .
H9 H -0.0288 0.8313 1.1040 0.025 Uiso 1 1 calc R U . . .
C10 C 0.0529(2) 0.6032(2) 1.12380(10) 0.0303(4) Uani 1 1 d . . . . .
H10A H 0.1774 0.6310 1.1377 0.045 Uiso 1 1 calc R U . . .
H10B H 0.0527 0.5042 1.0967 0.045 Uiso 1 1 calc R U . . .
H10C H -0.0192 0.5916 1.1680 0.045 Uiso 1 1 calc R U . . .
C11 C -0.2154(2) 0.6921(2) 1.04822(10) 0.0287(4) Uani 1 1 d . . . . .
H11A H -0.2581 0.7762 1.0158 0.043 Uiso 1 1 calc R U . . .
H11B H -0.2970 0.6821 1.0896 0.043 Uiso 1 1 calc R U . . .
H11C H -0.2129 0.5932 1.0210 0.043 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'
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 C9 120.57(12) . .
C1 N1 C2 127.49(13) . .
C1 N1 H1N 117.5(13) . .
C2 N1 H1N 114.9(13) . .
O1 C1 N1 112.77(13) . .
O1 C1 S1 125.35(11) . .
N1 C1 S1 121.88(12) . .
C7 C2 C3 121.32(15) . .
C7 C2 N1 120.31(14) . .
C3 C2 N1 118.32(13) . .
C2 C3 C4 117.61(15) . .
C2 C3 C8 121.89(15) . .
C4 C3 C8 120.49(16) . .
C5 C4 C3 121.58(17) . .
C5 C4 H4 119.2 . .
C3 C4 H4 119.2 . .
C4 C5 C6 119.80(16) . .
C4 C5 H5 120.1 . .
C6 C5 H5 120.1 . .
C5 C6 C7 120.13(16) . .
C5 C6 H6 119.9 . .
C7 C6 H6 119.9 . .
C6 C7 C2 119.54(16) . .
C6 C7 H7 120.2 . .
C2 C7 H7 120.2 . .
C3 C8 H8A 109.5 . .
C3 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C3 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
O1 C9 C10 109.56(13) . .
O1 C9 C11 104.80(12) . .
C10 C9 C11 113.03(14) . .
O1 C9 H9 109.8 . .
C10 C9 H9 109.8 . .
C11 C9 H9 109.8 . .
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 . .
C9 C11 H11A 109.5 . .
C9 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C9 C11 H11C 109.5 . .
H11A C11 H11C 109.5 . .
H11B C11 H11C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.6796(15) .
O1 C1 1.3275(18) .
O1 C9 1.4752(18) .
N1 C1 1.330(2) .
N1 C2 1.4367(19) .
N1 H1N 0.862(9) .
C2 C7 1.389(2) .
C2 C3 1.393(2) .
C3 C4 1.395(2) .
C3 C8 1.504(2) .
C4 C5 1.381(3) .
C4 H4 0.9500 .
C5 C6 1.381(3) .
C5 H5 0.9500 .
C6 C7 1.386(2) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 H8A 0.9800 .
C8 H8B 0.9800 .
C8 H8C 0.9800 .
C9 C10 1.504(2) .
C9 C11 1.512(2) .
C9 H9 1.0000 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 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
C9 O1 C1 N1 -177.91(13) . . . .
C9 O1 C1 S1 2.4(2) . . . .
C2 N1 C1 O1 7.1(2) . . . .
C2 N1 C1 S1 -173.17(12) . . . .
C1 N1 C2 C7 50.2(2) . . . .
C1 N1 C2 C3 -132.30(17) . . . .
C7 C2 C3 C4 1.5(2) . . . .
N1 C2 C3 C4 -176.07(14) . . . .
C7 C2 C3 C8 -177.20(16) . . . .
N1 C2 C3 C8 5.3(2) . . . .
C2 C3 C4 C5 -1.1(3) . . . .
C8 C3 C4 C5 177.61(18) . . . .
C3 C4 C5 C6 -0.1(3) . . . .
C4 C5 C6 C7 1.0(3) . . . .
C5 C6 C7 C2 -0.6(2) . . . .
C3 C2 C7 C6 -0.7(2) . . . .
N1 C2 C7 C6 176.81(14) . . . .
C1 O1 C9 C10 -83.51(17) . . . .
C1 O1 C9 C11 154.94(13) . . . .
