#------------------------------------------------------------------------------
#$Date: 2022-06-24 10:32:15 +0300 (Fri, 24 Jun 2022) $
#$Revision: 276228 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105497.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_8105497
loop_
_publ_author_name
'Caracelli, Ignez'
'Zukerman-Schpector, Julio'
'Garcia, Ariel L. Llanes'
'Alvarez, Heiddy Márquez'
'Tiekink, Edward R.T.'
_publ_section_title
;
 Crystal structure of O-hexyl benzoylcarbamothioate, C14H19NO2S
;
_journal_issue                   6
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1469
_journal_page_last               1471
_journal_paper_doi               10.1515/ncrs-2020-0361
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C14 H19 N O2 S'
_chemical_formula_sum            'C14 H19 N O2 S'
_chemical_formula_weight         265.36
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 112.845(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.6849(10)
_cell_length_b                   18.740(2)
_cell_length_c                   10.0465(12)
_cell_measurement_reflns_used    7285
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.28
_cell_measurement_theta_min      2.17
_cell_volume                     1506.9(3)
_computing_cell_refinement       'SAINT [2]'
_computing_data_collection       'APEX2 [2]'
_computing_data_reduction        'SAINT [2]'
_computing_molecular_graphics    'ORTEP-3 for Windows [5]'
_computing_publication_material  'SHELXL-2018/3 [3]'
_computing_structure_refinement  'SHELXL-2018/3 [4]'
_computing_structure_solution    'SIR2014 [3]'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0602
_diffrn_reflns_av_unetI/netI     0.0295
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            44808
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.438
_diffrn_reflns_theta_min         2.174
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6727
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS [1]'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       irregular
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.295
_exptl_crystal_size_mid          0.127
_exptl_crystal_size_min          0.086
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         3095
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.1161
_refine_ls_R_factor_gt           0.0685
_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)+(0.0691P)²+1.3108P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1708
_refine_ls_wR_factor_ref         0.2023
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1838
_reflns_number_total             3095
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0361_suppl.cif
_cod_data_source_block           shelx
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105497
_shelx_shelxl_version_number     2018/3
_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   0.941
_shelx_estimated_absorpt_t_max   0.982
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.11624(17) 0.38660(6) 0.19203(11) 0.1009(5) Uani 1 1 d . . . . .
O1 O 0.1362(3) 0.35784(13) -0.0561(2) 0.0774(7) Uani 1 1 d . . . . .
O2 O 0.3238(4) 0.26347(13) 0.3469(2) 0.0834(8) Uani 1 1 d . . . . .
N1 N 0.2573(3) 0.27733(14) 0.1066(2) 0.0590(7) Uani 1 1 d D . . . .
H1N H 0.270(4) 0.2599(16) 0.032(2) 0.071 Uiso 1 1 d D U . . .
C1 C 0.1709(4) 0.34067(17) 0.0810(3) 0.0594(8) Uani 1 1 d . . . . .
C2 C 0.3222(4) 0.23946(17) 0.2342(3) 0.0588(8) Uani 1 1 d . . . . .
C3 C 0.0388(6) 0.4221(2) -0.1146(4) 0.0886(12) Uani 1 1 d . . . . .
H3A H 0.100500 0.463951 -0.065618 0.106 Uiso 1 1 calc R U . . .
H3B H -0.065645 0.420393 -0.100794 0.106 Uiso 1 1 calc R U . . .
C4 C 0.0056(6) 0.4254(2) -0.2707(4) 0.1014(15) Uani 1 1 d . . . . .
H4A H -0.052376 0.469685 -0.309502 0.122 Uiso 1 1 calc R U . . .
H4B H 0.111689 0.426643 -0.281772 0.122 Uiso 1 1 calc R U . . .
C5 C -0.0945(7) 0.3654(3) -0.3567(5) 0.1186(17) Uani 1 1 d . . . . .
H5A H -0.196047 0.361206 -0.338742 0.142 Uiso 1 1 calc R U . . .
H5B H -0.031647 0.321535 -0.324734 0.142 Uiso 1 1 calc R U . . .
C6 C -0.1411(8) 0.3740(4) -0.5196(6) 0.160(3) Uani 1 1 d . . . . .
H6A H -0.209413 0.416485 -0.552025 0.192 Uiso 1 1 calc R U . . .
H6B H -0.039607 0.381486 -0.536339 0.192 Uiso 1 1 calc R U . . .
C7 C -0.2306(9) 0.3141(6) -0.6063(7) 0.216(4) Uani 1 1 d . . . . .
H7A H -0.157706 0.272763 -0.579756 0.259 Uiso 1 1 calc R U . . .
H7B H -0.325726 0.303690 -0.581659 0.259 Uiso 1 1 calc R U . . .
C8 C -0.2876(9) 0.3228(5) -0.7542(7) 0.208(4) Uani 1 1 d . . . . .
H8A H -0.350621 0.366285 -0.781458 0.313 Uiso 1 1 calc R U . . .
H8B H -0.357663 0.283218 -0.801407 0.313 Uiso 1 1 calc R U . . .
H8C H -0.194147 0.325008 -0.782623 0.313 Uiso 1 1 calc R U . . .
C9 C 0.3910(4) 0.16785(17) 0.2267(3) 0.0595(8) Uani 1 1 d . . . . .
C10 C 0.3545(5) 0.13003(18) 0.0991(4) 0.0693(9) Uani 1 1 d . . . . .
H10 H 0.289553 0.150868 0.011070 0.083 Uiso 1 1 calc R U . . .
C11 C 0.4143(6) 0.0618(2) 0.1029(5) 0.0908(12) Uani 1 1 d . . . . .
H11 H 0.387487 0.036348 0.017329 0.109 Uiso 1 1 calc R U . . .
C12 C 0.5128(6) 0.0310(3) 0.2313(6) 0.1048(15) Uani 1 1 d . . . . .
H12 H 0.553510 -0.015058 0.232688 0.126 Uiso 1 1 calc R U . . .
C13 C 0.5514(6) 0.0680(3) 0.3579(5) 0.1029(14) Uani 1 1 d . . . . .
H13 H 0.618969 0.047254 0.445186 0.123 Uiso 1 1 calc R U . . .
C14 C 0.4906(5) 0.1356(2) 0.3560(4) 0.0831(11) Uani 1 1 d . . . . .
H14 H 0.516390 0.160218 0.442349 0.100 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 C3 118.7(3) . .
C1 N1 C2 128.0(2) . .
C1 N1 H1N 114(2) . .
C2 N1 H1N 118(2) . .
O1 C1 N1 106.9(2) . .
O1 C1 S1 125.1(3) . .
N1 C1 S1 127.9(2) . .
O2 C2 N1 121.9(3) . .
O2 C2 C9 121.6(3) . .
N1 C2 C9 116.5(2) . .
O1 C3 C4 107.8(3) . .
O1 C3 H3A 110.1 . .
C4 C3 H3A 110.1 . .
O1 C3 H3B 110.1 . .
C4 C3 H3B 110.1 . .
H3A C3 H3B 108.5 . .
C5 C4 C3 114.5(4) . .
C5 C4 H4A 108.6 . .
C3 C4 H4A 108.6 . .
C5 C4 H4B 108.6 . .
C3 C4 H4B 108.6 . .
H4A C4 H4B 107.6 . .
C4 C5 C6 113.3(5) . .
C4 C5 H5A 108.9 . .
C6 C5 H5A 108.9 . .
C4 C5 H5B 108.9 . .
C6 C5 H5B 108.9 . .
H5A C5 H5B 107.7 . .
C7 C6 C5 114.7(7) . .
C7 C6 H6A 108.6 . .
C5 C6 H6A 108.6 . .
C7 C6 H6B 108.6 . .
C5 C6 H6B 108.6 . .
H6A C6 H6B 107.6 . .
C8 C7 C6 116.1(8) . .
C8 C7 H7A 108.3 . .
C6 C7 H7A 108.3 . .
C8 C7 H7B 108.3 . .
C6 C7 H7B 108.3 . .
H7A C7 H7B 107.4 . .
C7 C8 H8A 109.5 . .
C7 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C7 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C14 C9 C10 118.5(3) . .
C14 C9 C2 117.6(3) . .
C10 C9 C2 123.8(3) . .
C11 C10 C9 120.0(3) . .
C11 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
C12 C11 C10 120.7(4) . .
C12 C11 H11 119.7 . .
C10 C11 H11 119.7 . .
C11 C12 C13 119.9(4) . .
C11 C12 H12 120.1 . .
C13 C12 H12 120.1 . .
C14 C13 C12 120.1(4) . .
C14 C13 H13 120.0 . .
C12 C13 H13 120.0 . .
C13 C14 C9 120.8(4) . .
C13 C14 H14 119.6 . .
C9 C14 H14 119.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.620(3) .
O1 C1 1.329(3) .
O1 C3 1.457(4) .
O2 C2 1.214(3) .
N1 C1 1.374(4) .
N1 C2 1.379(4) .
N1 H1N 0.858(10) .
C2 C9 1.483(4) .
C3 C4 1.482(5) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 C5 1.478(7) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 C6 1.534(7) .
C5 H5A 0.9700 .
C5 H5B 0.9700 .
C6 C7 1.449(9) .
C6 H6A 0.9700 .
C6 H6B 0.9700 .
C7 C8 1.382(8) .
C7 H7A 0.9700 .
C7 H7B 0.9700 .
C8 H8A 0.9600 .
C8 H8B 0.9600 .
C8 H8C 0.9600 .
C9 C14 1.389(5) .
C9 C10 1.390(4) .
C10 C11 1.375(5) .
C10 H10 0.9300 .
C11 C12 1.369(6) .
C11 H11 0.9300 .
C12 C13 1.372(6) .
C12 H12 0.9300 .
C13 C14 1.369(6) .
C13 H13 0.9300 .
C14 H14 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C3 O1 C1 N1 177.8(3) . . . .
C3 O1 C1 S1 -1.2(5) . . . .
C2 N1 C1 O1 178.7(3) . . . .
C2 N1 C1 S1 -2.4(5) . . . .
C1 N1 C2 O2 -8.0(5) . . . .
C1 N1 C2 C9 172.4(3) . . . .
C1 O1 C3 C4 -175.2(3) . . . .
O1 C3 C4 C5 62.3(5) . . . .
C3 C4 C5 C6 174.4(4) . . . .
C4 C5 C6 C7 176.4(6) . . . .
C5 C6 C7 C8 174.4(7) . . . .
O2 C2 C9 C14 -14.2(5) . . . .
N1 C2 C9 C14 165.4(3) . . . .
O2 C2 C9 C10 162.3(3) . . . .
N1 C2 C9 C10 -18.0(5) . . . .
C14 C9 C10 C11 1.1(5) . . . .
C2 C9 C10 C11 -175.4(3) . . . .
C9 C10 C11 C12 -1.4(6) . . . .
C10 C11 C12 C13 0.6(7) . . . .
C11 C12 C13 C14 0.4(8) . . . .
C12 C13 C14 C9 -0.7(7) . . . .
C10 C9 C14 C13 -0.1(6) . . . .
C2 C9 C14 C13 176.6(4) . . . .
