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#$Date: 2024-09-06 04:57:20 +0300 (Fri, 06 Sep 2024) $
#$Revision: 294636 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/16/00/7160061.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_7160061
loop_
_publ_author_name
'Gong, Yingbin'
'Yan, Leilei'
'Guo, Zhiqiang'
_publ_section_title
;
 Na₂CO₃-promoted synthesis of thiocarbamates from
 isocyanates and thiols under mild conditions.
;
_journal_issue                   31
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              6277
_journal_page_last               6281
_journal_paper_doi               10.1039/d4ob01068j
_journal_volume                  22
_journal_year                    2024
_chemical_formula_sum            'C14 H13 N O2 S'
_chemical_formula_weight         259.31
_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   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2021-11-06 deposited with the CCDC.	2024-07-17 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 107.970(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3641(8)
_cell_length_b                   11.7805(7)
_cell_length_c                   8.6325(5)
_cell_measurement_reflns_used    7183
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      3.02
_cell_volume                     1292.77(13)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.990
_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  0.0304
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            12988
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.351
_diffrn_reflns_theta_min         3.024
_exptl_absorpt_coefficient_mu    0.243
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.340
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         3196
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0381
_refine_ls_shift/su_max          0.023
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0556P)²+0.3874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1149
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2717
_reflns_number_total             3196
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ob01068j2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7160060--7160061.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7160061
_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   0.958
_shelx_estimated_absorpt_t_max   0.988
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
C1 C 0.81893(12) 0.70200(14) 1.07557(17) 0.0402(3) Uani 1 1 d . . . . .
C2 C 0.86713(15) 0.79769(17) 1.0419(3) 0.0575(5) Uani 1 1 d . . . . .
H2 H 0.8288 0.8643 1.0106 0.069 Uiso 1 1 calc R U . . .
C3 C 0.97294(17) 0.7947(2) 1.0548(3) 0.0712(6) Uani 1 1 d . . . . .
H3 H 1.0057 0.8588 1.0301 0.085 Uiso 1 1 calc R U . . .
C4 C 1.02916(16) 0.6966(2) 1.1043(3) 0.0700(6) Uani 1 1 d . . . . .
H4 H 1.1006 0.6947 1.1156 0.084 Uiso 1 1 calc R U . . .
C5 C 0.98035(15) 0.6012(2) 1.1373(2) 0.0647(5) Uani 1 1 d . . . . .
H5 H 1.0196 0.5354 1.1706 0.078 Uiso 1 1 calc R U . . .
C6 C 0.87358(13) 0.60057(16) 1.1221(2) 0.0490(4) Uani 1 1 d . . . . .
C7 C 0.82002(19) 0.49531(19) 1.1535(3) 0.0751(6) Uani 1 1 d . . . . .
H7A H 0.7933 0.5081 1.2433 0.113 Uiso 1 1 calc R U . . .
H7B H 0.8695 0.4338 1.1791 0.113 Uiso 1 1 calc R U . . .
H7C H 0.7629 0.4766 1.0581 0.113 Uiso 1 1 calc R U . . .
C8 C 0.63442(11) 0.67837(11) 0.92559(17) 0.0332(3) Uani 1 1 d . . . . .
C9 C 0.42692(11) 0.63754(13) 0.75326(17) 0.0360(3) Uani 1 1 d . . . . .
C10 C 0.44405(12) 0.53148(13) 0.69589(19) 0.0403(3) Uani 1 1 d . . . . .
H10 H 0.4962 0.4844 0.7605 0.048 Uiso 1 1 calc R U . . .
C11 C 0.38401(12) 0.49561(12) 0.54348(19) 0.0397(3) Uani 1 1 d . . . . .
H11 H 0.3970 0.4253 0.5046 0.048 Uiso 1 1 calc R U . . .
C12 C 0.30434(11) 0.56423(13) 0.44816(18) 0.0371(3) Uani 1 1 d . . . . .
C13 C 0.28322(12) 0.66785(13) 0.50844(19) 0.0408(3) Uani 1 1 d . . . . .
H13 H 0.2272 0.7121 0.4475 0.049 Uiso 1 1 calc R U . . .
C14 C 0.34564(12) 0.70509(13) 0.65935(19) 0.0393(3) Uani 1 1 d . . . . .
H14 H 0.3331 0.7756 0.6980 0.047 Uiso 1 1 calc R U . . .
N1 N 0.70921(10) 0.70680(12) 1.06269(15) 0.0425(3) Uani 1 1 d . . . . .
H1 H 0.6913 0.7286 1.1455 0.051 Uiso 1 1 calc R U . . .
O1 O 0.65209(8) 0.64979(10) 0.80032(12) 0.0417(3) Uani 1 1 d . . . . .
O2 O 0.24513(9) 0.53429(11) 0.29476(14) 0.0520(3) Uani 1 1 d . . . . .
H2A H 0.2701 0.4772 0.2666 0.078 Uiso 1 1 calc R U . . .
S1 S 0.50556(3) 0.68722(4) 0.94594(5) 0.04477(14) Uani 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'
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
_geom_angle_publ_flag
C2 C1 C6 121.78(16) . . ?
C2 C1 N1 119.04(15) . . ?
C6 C1 N1 119.17(15) . . ?
C1 C2 C3 119.76(19) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
C4 C3 C2 119.6(2) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 120.30(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 121.58(19) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 116.96(18) . . ?
C5 C6 C7 121.38(18) . . ?
C1 C6 C7 121.67(16) . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 123.84(13) . . ?
O1 C8 S1 123.90(11) . . ?
N1 C8 S1 112.26(10) . . ?
C10 C9 C14 119.53(13) . . ?
C10 C9 S1 121.13(11) . . ?
C14 C9 S1 119.33(11) . . ?
C11 C10 C9 120.29(14) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.11(14) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
O2 C12 C11 122.34(14) . . ?
O2 C12 C13 117.85(13) . . ?
C11 C12 C13 119.82(14) . . ?
C14 C13 C12 119.86(14) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 120.26(14) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?
C8 N1 C1 121.71(12) . . ?
C8 N1 H1 119.1 . . ?
C1 N1 H1 119.1 . . ?
C12 O2 H2A 109.5 . . ?
C9 S1 C8 101.48(6) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(3) . ?
C1 C6 1.394(2) . ?
C1 N1 1.4371(19) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.373(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.498(3) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O1 1.2231(17) . ?
C8 N1 1.3350(18) . ?
C8 S1 1.7871(14) . ?
C9 C10 1.389(2) . ?
C9 C14 1.388(2) . ?
C9 S1 1.7706(15) . ?
C10 C11 1.379(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.387(2) . ?
C11 H11 0.9300 . ?
C12 O2 1.3629(18) . ?
C12 C13 1.390(2) . ?
C13 C14 1.384(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 H1 0.8600 . ?
O2 H2A 0.8200 . ?
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
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.3(3) . . . . ?
N1 C1 C2 C3 179.56(17) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
C2 C3 C4 C5 1.5(3) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
C4 C5 C6 C7 178.2(2) . . . . ?
C2 C1 C6 C5 1.6(2) . . . . ?
N1 C1 C6 C5 -178.23(15) . . . . ?
C2 C1 C6 C7 -177.98(19) . . . . ?
N1 C1 C6 C7 2.2(2) . . . . ?
C14 C9 C10 C11 3.0(2) . . . . ?
S1 C9 C10 C11 -178.09(11) . . . . ?
C9 C10 C11 C12 -1.6(2) . . . . ?
C10 C11 C12 O2 177.80(14) . . . . ?
C10 C11 C12 C13 -1.8(2) . . . . ?
O2 C12 C13 C14 -175.87(14) . . . . ?
C11 C12 C13 C14 3.7(2) . . . . ?
C12 C13 C14 C9 -2.3(2) . . . . ?
C10 C9 C14 C13 -1.1(2) . . . . ?
S1 C9 C14 C13 -179.97(11) . . . . ?
O1 C8 N1 C1 -2.3(2) . . . . ?
S1 C8 N1 C1 177.86(12) . . . . ?
C2 C1 N1 C8 92.71(19) . . . . ?
C6 C1 N1 C8 -87.44(19) . . . . ?
C10 C9 S1 C8 56.72(13) . . . . ?
C14 C9 S1 C8 -124.40(12) . . . . ?
O1 C8 S1 C9 3.44(14) . . . . ?
N1 C8 S1 C9 -176.72(11) . . . . ?
