#------------------------------------------------------------------------------
#$Date: 2020-11-29 04:34:11 +0200 (Sun, 29 Nov 2020) $
#$Revision: 259294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241490.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_7241490
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            'C9 H9 Cl2 N O S'
_chemical_formula_weight         250.13
_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
_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                 97.9720(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2726(2)
_cell_length_b                   7.4019(2)
_cell_length_c                   19.9994(4)
_cell_measurement_reflns_used    9316
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      33.1700
_cell_measurement_theta_min      3.1408
_cell_volume                     1066.18(5)
_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 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0378
_diffrn_reflns_av_unetI/netI     0.0310
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            19201
_diffrn_reflns_theta_full        33.18
_diffrn_reflns_theta_max         33.18
_diffrn_reflns_theta_min         3.14
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.769
_exptl_absorpt_correction_T_max  0.84
_exptl_absorpt_correction_T_min  0.67
_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    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             512
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.320
_exptl_crystal_size_min          0.240
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.451
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         4034
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0426
_refine_ls_R_factor_gt           0.0321
_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)+(0.0288P)²+0.5814P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0802
_reflns_number_gt                3407
_reflns_number_total             4034
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01336f2.cif
_cod_data_source_block           fg794m
_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               7241490
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 0.62629(16) 0.66304(16) 0.56124(6) 0.0152(2) Uani d . . . 1 . .
C C2 0.45804(18) 0.66681(17) 0.58660(6) 0.0172(2) Uani d . . . 1 . .
C C3 0.30168(18) 0.74428(17) 0.55053(6) 0.0194(2) Uani d . . . 1 . .
H H3 0.188188 0.748948 0.56895 0.023 Uiso calc U . R 1 . .
C C4 0.31341(17) 0.81516(17) 0.48688(6) 0.0189(2) Uani d . . . 1 . .
H H4 0.207269 0.86959 0.461794 0.023 Uiso calc U . R 1 . .
C C5 0.47814(17) 0.80721(17) 0.45971(6) 0.0184(2) Uani d . . . 1 . .
H H5 0.484181 0.853061 0.415706 0.022 Uiso calc U . R 1 . .
C C6 0.63472(17) 0.73183(17) 0.49712(6) 0.0163(2) Uani d . . . 1 . .
C C7 0.86789(16) 0.65753(17) 0.65356(6) 0.0156(2) Uani d . . . 1 . .
C C8 1.06045(19) 0.5890(2) 0.75940(6) 0.0237(3) Uani d . . . 1 . .
H H8A 1.106153 0.712628 0.755576 0.036 Uiso calc U . R 1 . .
H H8B 1.166017 0.506676 0.769916 0.036 Uiso calc U . R 1 . .
H H8C 0.982338 0.583609 0.795535 0.036 Uiso calc U . R 1 . .
C C9 0.9288(2) 0.34056(17) 0.68528(7) 0.0217(2) Uani d . . . 1 . .
H H9A 0.841739 0.318049 0.644157 0.033 Uiso calc U . R 1 . .
H H9B 0.880129 0.286953 0.724064 0.033 Uiso calc U . R 1 . .
H H9C 1.049244 0.286176 0.680691 0.033 Uiso calc U . R 1 . .
Cl Cl1 0.44602(5) 0.56766(5) 0.66426(2) 0.02388(8) Uani d . . . 1 . .
Cl Cl2 0.84210(4) 0.72563(5) 0.46460(2) 0.02472(8) Uani d . . . 1 . .
N N1 0.95151(15) 0.53566(15) 0.69563(5) 0.01743(19) Uani d . . . 1 . .
O O1 0.77818(12) 0.57615(12) 0.59636(4) 0.01787(17) Uani d . . . 1 . .
S S1 0.87199(5) 0.88066(4) 0.66384(2) 0.02075(8) 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'
Cl Cl 0.1484 0.1585 '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 C2 . . 120.41(10) ?
O1 C1 C6 . . 120.34(11) ?
C2 C1 C6 . . 118.94(11) ?
C3 C2 C1 . . 121.34(11) ?
C3 C2 Cl1 . . 120.22(10) ?
C1 C2 Cl1 . . 118.43(9) ?
C2 C3 C4 . . 118.90(12) ?
C5 C4 C3 . . 120.66(11) ?
C4 C5 C6 . . 119.68(11) ?
C1 C6 C5 . . 120.42(11) ?
C1 C6 Cl2 . . 119.43(9) ?
C5 C6 Cl2 . . 120.14(9) ?
N1 C7 O1 . . 110.72(10) ?
N1 C7 S1 . . 126.83(9) ?
O1 C7 S1 . . 122.41(9) ?
C7 N1 C8 . . 121.15(11) ?
C7 N1 C9 . . 123.33(10) ?
C8 N1 C9 . . 115.29(10) ?
C7 O1 C1 . . 118.19(9) ?
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 . 1.3828(14) ?
C1 C2 . 1.3883(17) ?
C1 C6 . 1.3890(16) ?
C2 C3 . 1.3838(18) ?
C2 Cl1 . 1.7310(12) ?
C3 C4 . 1.3903(18) ?
C4 C5 . 1.3836(18) ?
C5 C6 . 1.3897(17) ?
C6 Cl2 . 1.7239(12) ?
C7 N1 . 1.3228(15) ?
C7 O1 . 1.3747(14) ?
C7 S1 . 1.6641(13) ?
C8 N1 . 1.4595(16) ?
C9 N1 . 1.4649(17) ?
