#------------------------------------------------------------------------------
#$Date: 2020-11-29 04:34:11 +0200 (Sun, 29 Nov 2020) $
#$Revision: 259294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241489.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_7241489
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            'C19 H17 N O S'
_chemical_formula_weight         307.39
_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
_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                 117.231(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.044(2)
_cell_length_b                   5.7630(7)
_cell_length_c                   18.072(2)
_cell_measurement_reflns_used    2157
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      26.1226
_cell_measurement_theta_min      2.5350
_cell_volume                     1578.4(3)
_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      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  0.1042
_diffrn_reflns_av_unetI/netI     0.1026
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            11516
_diffrn_reflns_theta_full        26.41
_diffrn_reflns_theta_max         26.41
_diffrn_reflns_theta_min         2.69
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.54
_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    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.280
_exptl_crystal_size_min          0.020
_refine_diff_density_max         1.130
_refine_diff_density_min         -1.062
_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     201
_refine_ls_number_reflns         3228
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1248
_refine_ls_R_factor_gt           0.0903
_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)+(0.1470P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2083
_refine_ls_wR_factor_ref         0.2399
_reflns_number_gt                2163
_reflns_number_total             3228
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01336f2.cif
_cod_data_source_block           fg916m
_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               7241489
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_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 0.2836(2) 0.5192(6) 0.5629(2) 0.0190(8) Uani d . . . 1 . .
C C2 0.4427(3) 0.5154(8) 0.6506(3) 0.0328(10) Uani d . . . 1 . .
H H2A 0.456055 0.462607 0.606017 0.049 Uiso calc U . R 1 . .
H H2B 0.485665 0.448967 0.703683 0.049 Uiso calc U . R 1 . .
H H2C 0.445951 0.685107 0.653958 0.049 Uiso calc U . R 1 . .
C C3 0.3434(2) 0.2898(6) 0.6917(2) 0.0212(8) Uani d . . . 1 . .
C C4 0.3761(2) 0.3610(6) 0.7735(2) 0.0210(8) Uani d . . . 1 . .
H H4 0.403802 0.508425 0.789391 0.025 Uiso calc U . R 1 . .
C C5 0.3693(3) 0.2205(6) 0.8332(2) 0.0222(8) Uani d . . . 1 . .
C C6 0.4059(3) 0.2997(7) 0.9224(2) 0.0307(10) Uani d . . . 1 . .
H H6A 0.469197 0.265417 0.951831 0.046 Uiso calc U . R 1 . .
H H6B 0.375571 0.21804 0.949489 0.046 Uiso calc U . R 1 . .
H H6C 0.396768 0.46723 0.923836 0.046 Uiso calc U . R 1 . .
C C7 0.3280(3) 0.0061(6) 0.8079(2) 0.0227(8) Uani d . . . 1 . .
H H7 0.321977 -0.092218 0.847148 0.027 Uiso calc U . R 1 . .
C C8 0.2956(3) -0.0656(6) 0.7258(2) 0.0236(8) Uani d . . . 1 . .
H H8 0.267624 -0.212516 0.709689 0.028 Uiso calc U . R 1 . .
C C9 0.3034(3) 0.0729(6) 0.6674(2) 0.0225(8) Uani d . . . 1 . .
H H9 0.281857 0.021625 0.61149 0.027 Uiso calc U . R 1 . .
C C10 0.1269(2) 0.4919(6) 0.4893(2) 0.0204(8) Uani d . . . 1 . .
C C11 0.0920(2) 0.3315(6) 0.4274(2) 0.0182(8) Uani d . . . 1 . .
H H11 0.123678 0.194085 0.429407 0.022 Uiso calc U . R 1 . .
C C12 0.0071(2) 0.3732(6) 0.3596(2) 0.0188(8) Uani d . . . 1 . .
C C13 -0.0330(3) 0.2137(6) 0.2929(2) 0.0204(8) Uani d . . . 1 . .
H H13 -0.003571 0.073016 0.293685 0.024 Uiso calc U . R 1 . .
C C14 -0.1136(3) 0.2604(6) 0.2275(2) 0.0230(8) Uani d . . . 1 . .
H H14 -0.139095 0.153641 0.182631 0.028 Uiso calc U . R 1 . .
C C15 -0.1591(3) 0.4648(6) 0.2262(2) 0.0221(8) Uani d . . . 1 . .
H H15 -0.215095 0.495195 0.18058 0.027 Uiso calc U . R 1 . .
C C16 -0.1229(2) 0.6210(6) 0.2905(2) 0.0215(8) Uani d . . . 1 . .
H H16 -0.154416 0.758206 0.289276 0.026 Uiso calc U . R 1 . .
C C17 -0.0388(2) 0.5789(6) 0.3590(2) 0.0188(8) Uani d . . . 1 . .
C C18 0.0011(3) 0.7387(6) 0.4256(2) 0.0216(8) Uani d . . . 1 . .
H H18 -0.029088 0.87737 0.425352 0.026 Uiso calc U . R 1 . .
C C19 0.0827(3) 0.6957(6) 0.4902(2) 0.0227(8) Uani d . . . 1 . .
H H19 0.108822 0.802426 0.53504 0.027 Uiso calc U . R 1 . .
N N1 0.3531(2) 0.4393(5) 0.63265(18) 0.0204(7) Uani d . . . 1 . .
O O1 0.20747(17) 0.4409(4) 0.55989(15) 0.0231(6) Uani d . . . 1 . .
S S1 0.29030(7) 0.69061(16) 0.49283(6) 0.0243(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
O1 C1 N1 . . 109.8(3) ?
O1 C1 S1 . . 124.8(3) ?
N1 C1 S1 . . 125.4(3) ?
C4 C3 C9 . . 120.3(3) ?
C4 C3 N1 . . 119.2(3) ?
C9 C3 N1 . . 120.5(3) ?
C3 C4 C5 . . 121.2(3) ?
C7 C5 C4 . . 118.0(3) ?
C7 C5 C6 . . 121.3(3) ?
C4 C5 C6 . . 120.7(3) ?
C8 C7 C5 . . 120.7(3) ?
C9 C8 C7 . . 121.1(3) ?
C8 C9 C3 . . 118.8(3) ?
C11 C10 C19 . . 123.0(4) ?
C11 C10 O1 . . 118.7(3) ?
C19 C10 O1 . . 118.0(3) ?
C10 C11 C12 . . 118.9(3) ?
C17 C12 C13 . . 119.1(3) ?
C17 C12 C11 . . 119.2(3) ?
C13 C12 C11 . . 121.8(3) ?
C14 C13 C12 . . 120.6(3) ?
C13 C14 C15 . . 120.5(4) ?
C16 C15 C14 . . 120.4(4) ?
C15 C16 C17 . . 120.5(3) ?
C12 C17 C18 . . 119.1(3) ?
C12 C17 C16 . . 118.9(3) ?
C18 C17 C16 . . 122.0(3) ?
C19 C18 C17 . . 120.9(3) ?
C18 C19 C10 . . 118.9(3) ?
C1 N1 C3 . . 123.1(3) ?
C1 N1 C2 . . 118.6(3) ?
C3 N1 C2 . . 118.3(3) ?
C1 O1 C10 . . 119.0(3) ?
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 O1 . 1.352(4) ?
C1 N1 . 1.355(5) ?
C1 S1 . 1.650(4) ?
C2 N1 . 1.476(5) ?
C3 C4 . 1.381(5) ?
C3 C9 . 1.395(5) ?
C3 N1 . 1.440(5) ?
C4 C5 . 1.396(5) ?
C5 C7 . 1.391(5) ?
C5 C6 . 1.509(5) ?
C7 C8 . 1.387(5) ?
C8 C9 . 1.378(5) ?
C10 C11 . 1.359(5) ?
C10 C19 . 1.400(5) ?
C10 O1 . 1.413(4) ?
C11 C12 . 1.426(5) ?
C12 C17 . 1.418(5) ?
C12 C13 . 1.418(5) ?
C13 C14 . 1.368(5) ?
C14 C15 . 1.404(5) ?
C15 C16 . 1.373(5) ?
C16 C17 . 1.422(5) ?
C17 C18 . 1.418(5) ?
C18 C19 . 1.368(5) ?
