#------------------------------------------------------------------------------
#$Date: 2020-11-29 04:34:11 +0200 (Sun, 29 Nov 2020) $
#$Revision: 259294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241481.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_7241481
loop_
_publ_author_name
'Tan, Davin'
'Ng, Zi Xuan'
'Ganguly, Rakesh'
'Li, Yongxin'
'Soo, Han Sen'
'Mohamed, Sharmarke'
'García, Felipe'
_publ_section_title
;
 Investigating the solid-state assembly of pharmaceutically-relevant
 N,N-dimethyl-O-thiocarbamates in the absence of labile hydrogen bonds
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01336F
_journal_year                    2020
_chemical_formula_sum            'C10 H13 N O2 S'
_chemical_formula_weight         211.27
_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   geom
_audit_update_record
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 99.0234(16)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7175(4)
_cell_length_b                   9.9546(4)
_cell_length_c                   12.4668(5)
_cell_measurement_reflns_used    7134
_cell_measurement_temperature    123.(2)
_cell_measurement_theta_max      30.9102
_cell_measurement_theta_min      2.6312
_cell_volume                     1068.47(8)
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'XS, VERSION 2013/1'
_diffrn_ambient_temperature      123.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Photon II CPADs detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Multilayer Mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0819
_diffrn_reflns_av_unetI/netI     0.0533
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            20239
_diffrn_reflns_theta_full        31.01
_diffrn_reflns_theta_max         31.01
_diffrn_reflns_theta_min         2.63
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.277
_exptl_absorpt_correction_T_max  0.94
_exptl_absorpt_correction_T_min  0.75
_exptl_absorpt_correction_type   'Numerical Mu Calculated'
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             448
_exptl_crystal_size_max          0.474
_exptl_crystal_size_mid          0.395
_exptl_crystal_size_min          0.228
_refine_diff_density_max         0.340
_refine_diff_density_min         -0.284
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0420
_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)+(0.0403P)²+0.3768P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0977
_refine_ls_wR_factor_ref         0.1094
_reflns_number_gt                2661
_reflns_number_total             3393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01336f2.cif
_cod_data_source_block           fg749m
_cod_database_code               7241481
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.27586(16) 0.59734(14) 0.45215(11) 0.0237(3) Uani d . . . 1 . .
C C2 0.33861(17) 0.67232(14) 0.37735(12) 0.0253(3) Uani d . . . 1 . .
H H2 0.416127 0.737601 0.400824 0.03 Uiso calc U . R 1 . .
C C3 0.28805(17) 0.65221(14) 0.26685(12) 0.0250(3) Uani d . . . 1 . .
H H3 0.33205 0.702486 0.214481 0.03 Uiso calc U . R 1 . .
C C4 0.17298(15) 0.55818(13) 0.23403(11) 0.0220(3) Uani d . . . 1 . .
C C5 0.1823(2) 0.60052(17) 0.04676(12) 0.0343(4) Uani d . . . 1 . .
H H5A 0.166154 0.697379 0.053593 0.052 Uiso calc U . R 1 . .
H H5B 0.133453 0.570392 -0.025404 0.052 Uiso calc U . R 1 . .
H H5C 0.29387 0.581414 0.056436 0.052 Uiso calc U . R 1 . .
C C6 0.11033(16) 0.48354(14) 0.31080(11) 0.0249(3) Uani d . . . 1 . .
H H6 0.031132 0.419522 0.287886 0.03 Uiso calc U . R 1 . .
C C7 0.16254(17) 0.50190(14) 0.42025(12) 0.0261(3) Uani d . . . 1 . .
H H7 0.12126 0.44976 0.472831 0.031 Uiso calc U . R 1 . .
C C8 0.26827(15) 0.70216(13) 0.62278(11) 0.0206(3) Uani d . . . 1 . .
C C9 0.47555(17) 0.61835(15) 0.76306(12) 0.0302(3) Uani d . . . 1 . .
H H9A 0.439914 0.533261 0.790103 0.045 Uiso calc U . R 1 . .
H H9B 0.543847 0.664116 0.821724 0.045 Uiso calc U . R 1 . .
H H9C 0.532721 0.600484 0.70287 0.045 Uiso calc U . R 1 . .
C C10 0.28518(19) 0.79085(17) 0.80448(12) 0.0331(3) Uani d . . . 1 . .
H H10A 0.293817 0.884947 0.783092 0.05 Uiso calc U . R 1 . .
H H10B 0.347972 0.776229 0.875885 0.05 Uiso calc U . R 1 . .
H H10C 0.176299 0.769793 0.80811 0.05 Uiso calc U . R 1 . .
N N1 0.34082(14) 0.70409(12) 0.72479(9) 0.0235(2) Uani d . . . 1 . .
O O1 0.11430(12) 0.53116(11) 0.12784(8) 0.0291(2) Uani d . . . 1 . .
O O2 0.33507(12) 0.61100(11) 0.56320(8) 0.0296(2) Uani d . . . 1 . .
S S1 0.11627(4) 0.79641(4) 0.57294(3) 0.02570(11) Uani d . . . 1 . .
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C7 . . 121.37(13) ?
C2 C1 O2 . . 119.48(13) ?
C7 C1 O2 . . 119.00(13) ?
C1 C2 C3 . . 119.69(13) ?
C4 C3 C2 . . 119.41(13) ?
O1 C4 C3 . . 124.16(13) ?
O1 C4 C6 . . 115.69(12) ?
C3 C4 C6 . . 120.15(12) ?
C7 C6 C4 . . 120.37(13) ?
C6 C7 C1 . . 118.99(13) ?
N1 C8 O2 . . 110.62(11) ?
N1 C8 S1 . . 125.55(11) ?
O2 C8 S1 . . 123.84(10) ?
C8 N1 C10 . . 120.15(12) ?
C8 N1 C9 . . 122.58(12) ?
C10 N1 C9 . . 117.25(11) ?
C4 O1 C5 . . 117.14(11) ?
C8 O2 C1 . . 118.66(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.373(2) ?
C1 C7 . 1.383(2) ?
C1 O2 . 1.4061(16) ?
C2 C3 . 1.3934(19) ?
C3 C4 . 1.3860(19) ?
C4 O1 . 1.3690(16) ?
C4 C6 . 1.389(2) ?
C5 O1 . 1.4273(19) ?
C6 C7 . 1.3812(19) ?
C8 N1 . 1.3286(17) ?
C8 O2 . 1.3602(16) ?
C8 S1 . 1.6625(14) ?
C9 N1 . 1.4696(18) ?
C10 N1 . 1.4558(19) ?
