#------------------------------------------------------------------------------
#$Date: 2020-11-29 04:34:11 +0200 (Sun, 29 Nov 2020) $
#$Revision: 259294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241487.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_7241487
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            'C13 H13 N O S'
_chemical_formula_weight         231.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yc'
_space_group_name_H-M_alt        'P 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_update_record
;
2018-03-21 deposited with the CCDC.	2020-10-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.293(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   11.9751(10)
_cell_length_b                   5.8514(5)
_cell_length_c                   8.4304(6)
_cell_measurement_reflns_used    2858
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      33.2346
_cell_measurement_theta_min      3.4818
_cell_volume                     574.90(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    'XT, VERSION 2014/5'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0973
_diffrn_reflns_av_unetI/netI     0.1417
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8996
_diffrn_reflns_theta_full        35.04
_diffrn_reflns_theta_max         35.04
_diffrn_reflns_theta_min         3.48
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.33
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.452
_refine_diff_density_min         -1.486
_refine_ls_abs_structure_details
;

Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         4562
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1215
_refine_ls_R_factor_gt           0.0936
_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)+(0.1498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2256
_refine_ls_wR_factor_ref         0.2591
_reflns_number_gt                3303
_reflns_number_total             4562
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01336f2.cif
_cod_data_source_block           fg834m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7241487
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, 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 0.4477(4) 0.5567(8) 0.5947(5) 0.0162(8) Uani d . . . 1 . .
H H1 0.489943 0.457746 0.676028 0.019 Uiso calc U . R 1 . .
C C2 0.3377(4) 0.5024(8) 0.5135(6) 0.0162(8) Uani d . . . 1 . .
H H2 0.304074 0.363876 0.538486 0.019 Uiso calc U . R 1 . .
C C3 0.2739(4) 0.6502(8) 0.3932(5) 0.0150(7) Uani d . . . 1 . .
C C4 0.1593(4) 0.5997(9) 0.3114(6) 0.0181(8) Uani d . . . 1 . .
H H4 0.12459 0.461562 0.334902 0.022 Uiso calc U . R 1 . .
C C5 0.0981(4) 0.7492(9) 0.1985(6) 0.0196(9) Uani d . . . 1 . .
H H5 0.021218 0.713883 0.144989 0.024 Uiso calc U . R 1 . .
C C6 0.1482(4) 0.9550(9) 0.1610(6) 0.0202(9) Uani d . . . 1 . .
H H6 0.105563 1.056009 0.081509 0.024 Uiso calc U . R 1 . .
C C7 0.2584(4) 1.0085(7) 0.2397(6) 0.0161(8) Uani d . . . 1 . .
H H7 0.291444 1.147725 0.214826 0.019 Uiso calc U . R 1 . .
C C8 0.3240(4) 0.8586(8) 0.3578(5) 0.0148(7) Uani d . . . 1 . .
C C9 0.4380(4) 0.9114(8) 0.4410(5) 0.0150(7) Uani d . . . 1 . .
H H9 0.473276 1.04893 0.417641 0.018 Uiso calc U . R 1 . .
C C10 0.4966(4) 0.7623(8) 0.5550(5) 0.0156(7) Uani d . . . 1 . .
C C11 0.6991(4) 0.7135(8) 0.6396(5) 0.0150(7) Uani d . . . 1 . .
C C12 0.9026(4) 0.7025(9) 0.7567(6) 0.0226(9) Uani d . . . 1 . .
H H12A 0.906232 0.564647 0.823703 0.034 Uiso calc U . R 1 . .
H H12B 0.961993 0.810375 0.810232 0.034 Uiso calc U . R 1 . .
H H12C 0.915272 0.661302 0.649516 0.034 Uiso calc U . R 1 . .
C C13 0.7821(5) 1.0060(8) 0.8400(7) 0.0220(10) Uani d . . . 1 . .
H H13A 0.7208 1.10751 0.783021 0.033 Uiso calc U . R 1 . .
H H13B 0.855184 1.088824 0.863723 0.033 Uiso calc U . R 1 . .
H H13C 0.764815 0.953978 0.94223 0.033 Uiso calc U . R 1 . .
N N1 0.7903(3) 0.8080(7) 0.7368(5) 0.0169(7) Uani d . . . 1 . .
O O1 0.6031(3) 0.8335(6) 0.6461(4) 0.0167(6) Uani d . . . 1 . .
S S1 0.70054(14) 0.4877(2) 0.52109(18) 0.0202(3) 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 C10 . . 118.8(4) ?
C2 C1 H1 . . 120.6 ?
C10 C1 H1 . . 120.6 ?
C1 C2 C3 . . 120.8(4) ?
C1 C2 H2 . . 119.6 ?
C3 C2 H2 . . 119.6 ?
C2 C3 C4 . . 121.6(4) ?
C2 C3 C8 . . 119.4(4) ?
C4 C3 C8 . . 119.0(4) ?
C5 C4 C3 . . 120.4(4) ?
C5 C4 H4 . . 119.8 ?
C3 C4 H4 . . 119.8 ?
C4 C5 C6 . . 120.7(4) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C7 C6 C5 . . 119.9(4) ?
C7 C6 H6 . . 120.1 ?
C5 C6 H6 . . 120.1 ?
C6 C7 C8 . . 120.9(4) ?
C6 C7 H7 . . 119.5 ?
C8 C7 H7 . . 119.5 ?
C9 C8 C7 . . 121.8(4) ?
C9 C8 C3 . . 119.2(4) ?
C7 C8 C3 . . 119.0(4) ?
C10 C9 C8 . . 119.3(4) ?
C10 C9 H9 . . 120.4 ?
C8 C9 H9 . . 120.4 ?
C9 C10 O1 . . 117.0(4) ?
C9 C10 C1 . . 122.5(4) ?
O1 C10 C1 . . 120.1(4) ?
N1 C11 O1 . . 110.1(4) ?
N1 C11 S1 . . 125.6(3) ?
O1 C11 S1 . . 124.2(3) ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
N1 C13 H13A . . 109.5 ?
N1 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
N1 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C11 N1 C12 . . 120.2(4) ?
C11 N1 C13 . . 122.5(4) ?
C12 N1 C13 . . 117.0(4) ?
C11 O1 C10 . . 119.9(4) ?
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 . 1.374(7) ?
C1 C10 . 1.412(7) ?
C1 H1 . 0.95 ?
C2 C3 . 1.416(6) ?
C2 H2 . 0.95 ?
C3 C4 . 1.419(6) ?
C3 C8 . 1.421(6) ?
C4 C5 . 1.374(7) ?
C4 H4 . 0.95 ?
C5 C6 . 1.413(7) ?
C5 H5 . 0.95 ?
C6 C7 . 1.370(7) ?
C6 H6 . 0.95 ?
C7 C8 . 1.420(6) ?
C7 H7 . 0.95 ?
C8 C9 . 1.418(6) ?
C9 C10 . 1.367(6) ?
C9 H9 . 0.95 ?
C10 O1 . 1.393(5) ?
C11 N1 . 1.327(6) ?
C11 O1 . 1.358(5) ?
C11 S1 . 1.659(5) ?
C12 N1 . 1.454(6) ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 N1 . 1.465(7) ?
C13 H13A . 0.98 ?
C13 H13B . 0.98 ?
C13 H13C . 0.98 ?
