#------------------------------------------------------------------------------
#$Date: 2020-11-29 04:34:11 +0200 (Sun, 29 Nov 2020) $
#$Revision: 259294 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/14/7241478.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_7241478
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 H6 F5 N O S'
_chemical_formula_weight         271.21
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -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                91.215(13)
_cell_angle_beta                 104.219(11)
_cell_angle_gamma                94.232(12)
_cell_formula_units_Z            2
_cell_length_a                   6.358(2)
_cell_length_b                   7.684(3)
_cell_length_c                   11.573(4)
_cell_measurement_reflns_used    7101
_cell_measurement_temperature    301.(2)
_cell_measurement_theta_max      29.6158
_cell_measurement_theta_min      3.3638
_cell_volume                     546.1(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      301.(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_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  0.0625
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18881
_diffrn_reflns_theta_full        29.69
_diffrn_reflns_theta_max         29.69
_diffrn_reflns_theta_min         2.66
_diffrn_source                   'Incoatec microfocus source'
_diffrn_source_type              'Bruker D8 Quest'
_exptl_absorpt_coefficient_mu    0.347
_exptl_absorpt_correction_T_max  0.91
_exptl_absorpt_correction_T_min  0.73
_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    1.649
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             272
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.280
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.255
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         3036
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0930
_refine_ls_R_factor_gt           0.0594
_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)+(0.0664P)²+0.2503P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1431
_refine_ls_wR_factor_ref         0.1678
_reflns_number_gt                1976
_reflns_number_total             3036
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01336f2.cif
_cod_data_source_block           fg754m
_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               7241478
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.7456(3) 0.2432(3) 0.76802(19) 0.0508(5) Uani d . . . 1 . .
C C2 0.7511(4) 0.0980(3) 0.8353(2) 0.0532(5) Uani d . . . 1 . .
C C3 0.7458(4) 0.1125(3) 0.9536(2) 0.0567(6) Uani d . . . 1 . .
C C4 0.7359(4) 0.2726(4) 1.0041(2) 0.0590(6) Uani d . . . 1 . .
C C5 0.7305(4) 0.4193(3) 0.9380(2) 0.0576(6) Uani d . . . 1 . .
C C6 0.7345(4) 0.4036(3) 0.8200(2) 0.0543(6) Uani d . . . 1 . .
C C7 0.9226(3) 0.2438(3) 0.60981(19) 0.0480(5) Uani d . . . 1 . .
C C8 0.6545(5) 0.2188(6) 0.4166(3) 0.0924(11) Uani d . . . 1 . .
H H8A 0.55414 0.247981 0.462474 0.139 Uiso calc U . R 1 . .
H H8B 0.620016 0.100286 0.385946 0.139 Uiso calc U . R 1 . .
H H8C 0.643738 0.295676 0.351479 0.139 Uiso calc U . R 1 . .
C C9 1.0503(6) 0.2504(5) 0.4305(3) 0.0791(9) Uani d . . . 1 . .
H H9A 1.147515 0.161282 0.456707 0.119 Uiso calc U . R 1 . .
H H9B 1.129127 0.363146 0.447958 0.119 Uiso calc U . R 1 . .
H H9C 0.988836 0.235064 0.346142 0.119 Uiso calc U . R 1 . .
F F1 0.7627(3) -0.0595(2) 0.78732(18) 0.0862(6) Uani d . . . 1 . .
F F2 0.7515(3) -0.0292(3) 1.01839(18) 0.0923(6) Uani d . . . 1 . .
F F3 0.7310(3) 0.2867(3) 1.11887(14) 0.0970(6) Uani d . . . 1 . .
F F4 0.7214(3) 0.5762(2) 0.9876(2) 0.0932(6) Uani d . . . 1 . .
F F5 0.7267(3) 0.5459(2) 0.75541(19) 0.0896(6) Uani d . . . 1 . .
N N1 0.8761(3) 0.2376(3) 0.49262(17) 0.0564(5) Uani d . . . 1 . .
O O1 0.7317(3) 0.2265(3) 0.64738(14) 0.0702(6) Uani d . . . 1 . .
S S1 1.16327(10) 0.26609(12) 0.70363(6) 0.0740(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'
F F 0.0171 0.0103 '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 C6 . . 119.1(2) ?
C2 C1 O1 . . 120.3(2) ?
C6 C1 O1 . . 120.3(2) ?
F1 C2 C1 . . 120.4(2) ?
F1 C2 C3 . . 119.0(2) ?
C1 C2 C3 . . 120.6(2) ?
F2 C3 C4 . . 120.2(2) ?
F2 C3 C2 . . 120.2(2) ?
C4 C3 C2 . . 119.7(2) ?
F3 C4 C3 . . 119.7(2) ?
F3 C4 C5 . . 119.9(3) ?
C3 C4 C5 . . 120.5(2) ?
F4 C5 C4 . . 120.4(2) ?
F4 C5 C6 . . 120.1(2) ?
C4 C5 C6 . . 119.5(2) ?
F5 C6 C1 . . 119.8(2) ?
F5 C6 C5 . . 119.5(2) ?
C1 C6 C5 . . 120.8(2) ?
N1 C7 O1 . . 109.53(19) ?
N1 C7 S1 . . 128.09(17) ?
O1 C7 S1 . . 122.38(16) ?
C7 N1 C9 . . 120.3(2) ?
C7 N1 C8 . . 123.8(2) ?
C9 N1 C8 . . 115.9(2) ?
C1 O1 C7 . . 118.28(17) ?
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 . 1.372(3) ?
C1 C6 . 1.374(4) ?
C1 O1 . 1.380(3) ?
C2 F1 . 1.335(3) ?
C2 C3 . 1.380(3) ?
C3 F2 . 1.333(3) ?
C3 C4 . 1.363(4) ?
C4 F3 . 1.339(3) ?
C4 C5 . 1.373(4) ?
C5 F4 . 1.335(3) ?
C5 C6 . 1.375(4) ?
C6 F5 . 1.335(3) ?
C7 N1 . 1.314(3) ?
C7 O1 . 1.384(3) ?
C7 S1 . 1.639(2) ?
C8 N1 . 1.461(4) ?
C9 N1 . 1.459(3) ?
