#------------------------------------------------------------------------------
#$Date: 2022-11-24 12:12:12 +0200 (Thu, 24 Nov 2022) $
#$Revision: 279546 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/62/8106247.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_8106247
loop_
_publ_author_name
'Yeo, Chien Ing'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure and molecular packing of O-ethyl
 (2-chlorophenyl)carbamothioate, C9H10ClNOS
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              651
_journal_page_last               653
_journal_paper_doi               10.1515/ncrs-2017-0422
_journal_volume                  233
_journal_year                    2018
_chemical_formula_moiety         'C9 H10 Cl N O S'
_chemical_formula_sum            'C9 H10 Cl N O S'
_chemical_formula_weight         215.69
_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   mixed
_cell_angle_alpha                81.007(3)
_cell_angle_beta                 82.268(4)
_cell_angle_gamma                73.210(3)
_cell_formula_units_Z            4
_cell_length_a                   7.2277(3)
_cell_length_b                   9.9791(3)
_cell_length_c                   14.7725(7)
_cell_measurement_reflns_used    5271
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.5009
_cell_measurement_theta_min      2.4108
_cell_volume                     1003.01(7)
_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 1.000
_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  0.0412
_diffrn_reflns_av_unetI/netI     0.0492
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14831
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         2.416
_exptl_absorpt_coefficient_mu    0.547
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89707
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlisPro [1]'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.428
_exptl_crystal_description       prism
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     243
_refine_ls_number_reflns         4637
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0364
_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)+(0.0284P)²+0.3988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0736
_refine_ls_wR_factor_ref         0.0828
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3653
_reflns_number_total             4637
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2017-0422_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8106247
_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   0.875
_shelx_estimated_absorpt_t_max   0.922
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 0.23116(7) 0.89133(5) 0.55038(4) 0.01979(12) Uani 1 1 d . . . . .
S1 S 0.72551(7) 0.49578(5) 0.39208(4) 0.01832(12) Uani 1 1 d . . . . .
O1 O 0.88124(18) 0.69256(13) 0.42503(9) 0.0160(3) Uani 1 1 d . . . . .
N1 N 0.6098(2) 0.68018(16) 0.51302(12) 0.0158(4) Uani 1 1 d D . . . .
H1N H 0.516(2) 0.6395(19) 0.5275(14) 0.019 Uiso 1 1 d D U . . .
C1 C 0.7412(3) 0.62787(18) 0.44502(13) 0.0142(4) Uani 1 1 d . . . . .
C2 C 0.6172(3) 0.78160(18) 0.56952(13) 0.0131(4) Uani 1 1 d . . . . .
C3 C 0.4465(3) 0.88320(18) 0.59369(13) 0.0132(4) Uani 1 1 d . . . . .
C4 C 0.4447(3) 0.97812(19) 0.65309(14) 0.0174(4) Uani 1 1 d . . . . .
H4 H 0.3277 1.0472 0.6686 0.021 Uiso 1 1 calc R U . . .
C5 C 0.6130(3) 0.9722(2) 0.68978(14) 0.0187(4) Uani 1 1 d . . . . .
H5 H 0.6123 1.0371 0.7306 0.022 Uiso 1 1 calc R U . . .
C6 C 0.7832(3) 0.8711(2) 0.66676(14) 0.0186(4) Uani 1 1 d . . . . .
H6 H 0.8988 0.8663 0.6925 0.022 Uiso 1 1 calc R U . . .
C7 C 0.7861(3) 0.77709(19) 0.60657(13) 0.0151(4) Uani 1 1 d . . . . .
H7 H 0.9039 0.7092 0.5905 0.018 Uiso 1 1 calc R U . . .
C8 C 1.0369(3) 0.64433(19) 0.35395(14) 0.0162(4) Uani 1 1 d . . . . .
H8A H 0.9828 0.6474 0.2953 0.019 Uiso 1 1 calc R U . . .
H8B H 1.1125 0.5463 0.3728 0.019 Uiso 1 1 calc R U . . .
C9 C 1.1636(3) 0.7427(2) 0.34278(15) 0.0214(5) Uani 1 1 d . . . . .
H9A H 1.0855 0.8397 0.3268 0.032 Uiso 1 1 calc R U . . .
H9B H 1.2679 0.7168 0.2937 0.032 Uiso 1 1 calc R U . . .
H9C H 1.2200 0.7358 0.4006 0.032 Uiso 1 1 calc R U . . .
Cl2 Cl 1.28896(7) 0.21559(5) 0.84908(4) 0.02177(13) Uani 1 1 d . . . . .
S2 S 0.75835(7) 0.65221(5) 0.92706(4) 0.01836(12) Uani 1 1 d . . . . .
O2 O 0.66577(19) 0.47596(13) 0.83298(9) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.8997(2) 0.37710(16) 0.92427(11) 0.0153(3) Uani 1 1 d D . . . .
H2N H 0.984(2) 0.388(2) 0.9574(13) 0.018 Uiso 1 1 d D U . . .
C10 C 0.7728(3) 0.49736(19) 0.89268(13) 0.0147(4) Uani 1 1 d . . . . .
C11 C 0.9090(3) 0.23908(18) 0.90591(13) 0.0141(4) Uani 1 1 d . . . . .
C12 C 1.0862(3) 0.15144(19) 0.87418(13) 0.0145(4) Uani 1 1 d . . . . .
C13 C 1.1029(3) 0.01333(19) 0.86231(14) 0.0177(4) Uani 1 1 d . . . . .
H13 H 1.2249 -0.0461 0.8419 0.021 Uiso 1 1 calc R U . . .
C14 C 0.9424(3) -0.03740(19) 0.88013(14) 0.0183(4) Uani 1 1 d . . . . .
H14 H 0.9533 -0.1318 0.8715 0.022 Uiso 1 1 calc R U . . .
C15 C 0.7639(3) 0.04928(19) 0.91076(14) 0.0180(4) Uani 1 1 d . . . . .
H15 H 0.6529 0.0142 0.9224 0.022 Uiso 1 1 calc R U . . .
C16 C 0.7480(3) 0.18672(19) 0.92426(13) 0.0161(4) Uani 1 1 d . . . . .
H16 H 0.6265 0.2452 0.9461 0.019 Uiso 1 1 calc R U . . .
C17 C 0.5246(3) 0.59411(19) 0.78729(14) 0.0173(4) Uani 1 1 d . . . . .
H17A H 0.5179 0.5757 0.7240 0.021 Uiso 1 1 calc R U . . .
H17B H 0.5669 0.6810 0.7829 0.021 Uiso 1 1 calc R U . . .
C18 C 0.3270(3) 0.6155(2) 0.83930(16) 0.0255(5) Uani 1 1 d . . . . .
H18A H 0.2911 0.5264 0.8496 0.038 Uiso 1 1 calc R U . . .
H18B H 0.2318 0.6873 0.8035 0.038 Uiso 1 1 calc R U . . .
H18C H 0.3292 0.6467 0.8987 0.038 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 118.86(14) . .
C1 N1 C2 127.78(16) . .
C1 N1 H1N 114.7(14) . .
C2 N1 H1N 117.1(14) . .
O1 C1 N1 112.88(16) . .
O1 C1 S1 124.60(14) . .
N1 C1 S1 122.51(15) . .
C7 C2 C3 118.66(17) . .
C7 C2 N1 122.18(16) . .
C3 C2 N1 119.01(17) . .
C4 C3 C2 120.93(18) . .
C4 C3 Cl1 118.75(14) . .
C2 C3 Cl1 120.31(14) . .
C5 C4 C3 119.89(18) . .
C5 C4 H4 120.1 . .
C3 C4 H4 120.1 . .
C4 C5 C6 119.68(18) . .
C4 C5 H5 120.2 . .
C6 C5 H5 120.2 . .
C7 C6 C5 120.60(18) . .
C7 C6 H6 119.7 . .
C5 C6 H6 119.7 . .
C6 C7 C2 120.22(17) . .
C6 C7 H7 119.9 . .
C2 C7 H7 119.9 . .
O1 C8 C9 106.42(15) . .
O1 C8 H8A 110.4 . .
C9 C8 H8A 110.4 . .
O1 C8 H8B 110.4 . .
C9 C8 H8B 110.4 . .
H8A C8 H8B 108.6 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C10 O2 C17 120.55(14) . .
C10 N2 C11 125.83(16) . .
C10 N2 H2N 115.0(13) . .
C11 N2 H2N 119.1(13) . .
O2 C10 N2 111.77(15) . .
O2 C10 S2 126.09(14) . .
N2 C10 S2 122.14(15) . .
C16 C11 C12 119.04(17) . .
C16 C11 N2 121.36(17) . .
C12 C11 N2 119.48(17) . .
C13 C12 C11 120.80(18) . .
C13 C12 Cl2 119.37(14) . .
C11 C12 Cl2 119.83(14) . .
C14 C13 C12 119.77(18) . .
C14 C13 H13 120.1 . .
C12 C13 H13 120.1 . .
C13 C14 C15 120.14(17) . .
C13 C14 H14 119.9 . .
C15 C14 H14 119.9 . .
C16 C15 C14 120.09(18) . .
C16 C15 H15 120.0 . .
C14 C15 H15 120.0 . .
C15 C16 C11 120.15(17) . .
C15 C16 H16 119.9 . .
C11 C16 H16 119.9 . .
O2 C17 C18 110.98(16) . .
O2 C17 H17A 109.4 . .
C18 C17 H17A 109.4 . .
O2 C17 H17B 109.4 . .
C18 C17 H17B 109.4 . .
H17A C17 H17B 108.0 . .
C17 C18 H18A 109.5 . .
C17 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C17 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 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 1.7369(19) .
S1 C1 1.6718(19) .
O1 C1 1.329(2) .
O1 C8 1.458(2) .
N1 C1 1.343(2) .
N1 C2 1.425(2) .
N1 H1N 0.873(9) .
C2 C7 1.390(3) .
C2 C3 1.397(2) .
C3 C4 1.384(3) .
C4 C5 1.379(3) .
C4 H4 0.9500 .
C5 C6 1.387(3) .
C5 H5 0.9500 .
C6 C7 1.384(3) .
C6 H6 0.9500 .
C7 H7 0.9500 .
C8 C9 1.503(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
Cl2 C12 1.7368(19) .
S2 C10 1.6717(18) .
O2 C10 1.327(2) .
O2 C17 1.459(2) .
N2 C10 1.343(2) .
N2 C11 1.426(2) .
N2 H2N 0.872(9) .
C11 C16 1.387(3) .
C11 C12 1.394(3) .
C12 C13 1.385(3) .
C13 C14 1.373(3) .
C13 H13 0.9500 .
C14 C15 1.392(3) .
C14 H14 0.9500 .
C15 C16 1.386(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C18 1.501(3) .
C17 H17A 0.9900 .
C17 H17B 0.9900 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 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 178.51(15) . . . .
C8 O1 C1 S1 -1.8(2) . . . .
C2 N1 C1 O1 -7.3(3) . . . .
C2 N1 C1 S1 172.99(15) . . . .
C1 N1 C2 C7 -43.0(3) . . . .
C1 N1 C2 C3 141.49(19) . . . .
C7 C2 C3 C4 0.2(3) . . . .
N1 C2 C3 C4 175.91(17) . . . .
C7 C2 C3 Cl1 -179.11(14) . . . .
N1 C2 C3 Cl1 -3.4(2) . . . .
C2 C3 C4 C5 -0.5(3) . . . .
Cl1 C3 C4 C5 178.82(15) . . . .
C3 C4 C5 C6 0.1(3) . . . .
C4 C5 C6 C7 0.7(3) . . . .
C5 C6 C7 C2 -1.0(3) . . . .
C3 C2 C7 C6 0.5(3) . . . .
N1 C2 C7 C6 -175.01(17) . . . .
C1 O1 C8 C9 176.33(16) . . . .
C17 O2 C10 N2 -177.28(15) . . . .
C17 O2 C10 S2 2.7(3) . . . .
C11 N2 C10 O2 -6.6(3) . . . .
C11 N2 C10 S2 173.39(15) . . . .
C10 N2 C11 C16 -54.7(3) . . . .
C10 N2 C11 C12 129.3(2) . . . .
C16 C11 C12 C13 -1.0(3) . . . .
N2 C11 C12 C13 175.13(17) . . . .
C16 C11 C12 Cl2 179.02(15) . . . .
N2 C11 C12 Cl2 -4.9(3) . . . .
C11 C12 C13 C14 1.4(3) . . . .
Cl2 C12 C13 C14 -178.63(16) . . . .
C12 C13 C14 C15 -0.5(3) . . . .
C13 C14 C15 C16 -0.6(3) . . . .
C14 C15 C16 C11 1.0(3) . . . .
C12 C11 C16 C15 -0.2(3) . . . .
N2 C11 C16 C15 -176.25(17) . . . .
C10 O2 C17 C18 -93.4(2) . . . .
