#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:56:51 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238072 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/47/1554712.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_1554712
loop_
_publ_author_name
'Barłóg, Maciej'
'Kulai, Ihor'
'Ji, Xiaozhou'
'Bhuvanesh, Nattamai'
'Dey, Somnath'
'Sliwinski, Eric Pierre'
'Bazzi, Hassan S.'
'Fang, Lei'
'Al-Hashimi, Mohammed'
_publ_section_title
;
 Synthesis, characterization and crystal structures of novel fluorinated
 di(thiazolyl)benzene derivatives
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              780
_journal_paper_doi               10.1039/C9QO00044E
_journal_volume                  6
_journal_year                    2019
_chemical_formula_moiety         'C12 H6 F2 N2 S2'
_chemical_formula_sum            'C12 H6 F2 N2 S2'
_chemical_formula_weight         280.31
_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_creation_date             2017-06-29
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.509(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.7427(3)
_cell_length_b                   5.5541(3)
_cell_length_c                   17.1753(8)
_cell_measurement_reflns_used    2797
_cell_measurement_temperature    100
_cell_measurement_theta_max      77.34
_cell_measurement_theta_min      5.15
_cell_volume                     547.79(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       APEX3
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker CMOS area detector'
_diffrn_detector_area_resol_mean 10.5
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.935
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker Micro-Source CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0313
_diffrn_reflns_Laue_measured_fraction_full 0.935
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            3760
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         78.795
_diffrn_reflns_theta_min         5.150
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1
_diffrn_source_target            Mo
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.514
_exptl_absorpt_correction_T_max  0.7542
_exptl_absorpt_correction_T_min  0.5449
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0974 before and 0.0450 after correction. The Ratio of minimum to maximum transmission is 0.7225. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.699
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1047
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0315
_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)+(0.0413P)²+0.3489P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0850
_reflns_Friedel_coverage         0.000
_reflns_number_gt                964
_reflns_number_total             1047
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9qo00044e2.cif
_cod_data_source_block           f2r
_cod_database_code               1554712
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.911
_shelx_estimated_absorpt_t_min   0.551
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6)
;
_olex2_submission_special_instructions 'No special instructions were received'
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
S1 S 0.40356(8) 0.52263(8) 0.31778(2) 0.02101(18) Uani 1 1 d .
F1 F 0.1885(2) 0.9110(2) 0.38417(6) 0.0244(3) Uani 1 1 d .
N1 N 0.7715(3) 0.4682(3) 0.40210(9) 0.0200(4) Uani 1 1 d .
C1 C 0.3023(3) 1.1446(3) 0.49160(10) 0.0187(4) Uani 1 1 d .
H1 H 0.166638 1.240449 0.484751 0.022 Uiso 1 1 calc R
C2 C 0.3454(4) 0.9551(3) 0.44247(10) 0.0190(4) Uani 1 1 d .
C3 C 0.5392(3) 0.8049(3) 0.44797(10) 0.0176(4) Uani 1 1 d .
C4 C 0.5852(3) 0.6045(3) 0.39493(10) 0.0180(4) Uani 1 1 d .
C5 C 0.7736(4) 0.2950(3) 0.34539(10) 0.0224(4) Uani 1 1 d .
H5 H 0.895694 0.180136 0.341909 0.027 Uiso 1 1 calc R
C6 C 0.5916(4) 0.2965(3) 0.29442(10) 0.0217(4) Uani 1 1 d .
H6 H 0.571834 0.187973 0.252113 0.026 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C6 S1 C4 89.71(9) . .
C4 N1 C5 110.48(16) . .
C2 C1 H1 120.4 . .
C2 C1 C3 119.25(18) . 3_676
C3 C1 H1 120.4 3_676 .
F1 C2 C1 117.87(17) . .
F1 C2 C3 117.70(16) . .
C1 C2 C3 124.43(18) . .
C1 C3 C4 119.51(17) 3_676 .
C2 C3 C1 116.33(16) . 3_676
C2 C3 C4 124.16(17) . .
N1 C4 S1 113.76(14) . .
N1 C4 C3 122.04(16) . .
C3 C4 S1 124.20(14) . .
N1 C5 H5 121.9 . .
C6 C5 N1 116.28(18) . .
C6 C5 H5 121.9 . .
S1 C6 H6 125.1 . .
C5 C6 S1 109.76(14) . .
C5 C6 H6 125.1 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C4 1.7396(18) .
S1 C6 1.707(2) .
F1 C2 1.363(2) .
N1 C4 1.315(2) .
N1 C5 1.369(2) .
C1 H1 0.9500 .
C1 C2 1.373(3) .
C1 C3 1.403(3) 3_676
C2 C3 1.393(3) .
C3 C4 1.464(2) .
C5 H5 0.9500 .
C5 C6 1.358(3) .
C6 H6 0.9500 .
