#------------------------------------------------------------------------------
#$Date: 2019-11-24 13:56:51 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238072 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/47/1554713.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_1554713
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         'C14 H6 F4 S2'
_chemical_formula_sum            'C14 H6 F4 S2'
_chemical_formula_weight         314.31
_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
_audit_creation_date             2017-06-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.341(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.2999(3)
_cell_length_b                   5.0655(3)
_cell_length_c                   18.6515(11)
_cell_measurement_reflns_used    4287
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.096
_cell_measurement_theta_min      4.742
_cell_volume                     595.20(6)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1110
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.090
_diffrn_reflns_theta_min         4.742
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.434
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.389
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1131 before and 0.0572 after correction.
 The Ratio of minimum to maximum transmission is 0.52.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1755 before and 0.1014 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 11761 reflections, Rint = 0.0724
 (9057 with I > 3sig(I), Rint = 0.0710)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.754
_exptl_crystal_description       needle
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.244
_exptl_crystal_size_mid          0.053
_exptl_crystal_size_min          0.021
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.332
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.147
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     91
_refine_ls_number_reflns         1110
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.147
_refine_ls_R_factor_all          0.0472
_refine_ls_R_factor_gt           0.0429
_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)+(0.0347P)²+1.3912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1048
_refine_ls_wR_factor_ref         0.1070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1019
_reflns_number_total             1110
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9qo00044e2.cif
_cod_data_source_block           f4p
_cod_database_code               1554713
_shelx_shelxl_version_number     2014/7
_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   0.913
_shelx_estimated_absorpt_t_min   0.411
_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), C2(H2), C3(H3)
;
_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 0.38499(11) 1.00713(15) 0.33096(4) 0.0210(2) Uani 1 1 d .
F1 F 0.1976(2) 0.5928(3) 0.39976(8) 0.0201(4) Uani 1 1 d .
F2 F 0.1305(2) 0.2316(4) 0.49483(9) 0.0227(4) Uani 1 1 d .
C1 C 0.5479(5) 1.2385(6) 0.29432(15) 0.0229(7) Uani 1 1 d .
H1 H 0.5074 1.3529 0.2563 0.028 Uiso 1 1 calc R
C2 C 0.7415(5) 1.2400(6) 0.32587(15) 0.0217(6) Uani 1 1 d .
H2 H 0.8524 1.3559 0.3120 0.026 Uiso 1 1 calc R
C3 C 0.7632(4) 1.0528(5) 0.38142(14) 0.0146(5) Uani 1 1 d .
H3 H 0.8896 1.0288 0.4087 0.018 Uiso 1 1 calc R
C4 C 0.5780(4) 0.9070(6) 0.39186(14) 0.0160(6) Uani 1 1 d .
C5 C 0.5380(4) 0.7028(6) 0.44588(14) 0.0153(6) Uani 1 1 d .
C6 C 0.3528(4) 0.5534(6) 0.44899(14) 0.0157(6) Uani 1 1 d .
C7 C 0.3165(4) 0.3618(6) 0.50015(14) 0.0157(6) Uani 1 1 d .
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'
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
C1 S1 C4 92.42(14) . .
S1 C1 H1 124.0 . .
C2 C1 S1 111.9(2) . .
C2 C1 H1 124.0 . .
C1 C2 H2 123.2 . .
C1 C2 C3 113.6(3) . .
C3 C2 H2 123.2 . .
C2 C3 H3 123.8 . .
C4 C3 C2 112.4(2) . .
C4 C3 H3 123.8 . .
C3 C4 S1 109.7(2) . .
C3 C4 C5 128.0(2) . .
C5 C4 S1 122.2(2) . .
C6 C5 C4 124.0(3) . .
C6 C5 C7 112.9(3) . 3_666
C7 C5 C4 123.1(2) 3_666 .
F1 C6 C5 119.6(3) . .
F1 C6 C7 116.8(2) . .
C7 C6 C5 123.6(3) . .
F2 C7 C5 120.3(3) . 3_666
F2 C7 C6 116.2(2) . .
C6 C7 C5 123.5(2) . 3_666
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.704(3) .
S1 C4 1.735(3) .
F1 C6 1.352(3) .
F2 C7 1.348(3) .
C1 H1 0.9500 .
C1 C2 1.351(4) .
C2 H2 0.9500 .
C2 C3 1.410(4) .
C3 H3 0.9500 .
C3 C4 1.396(4) .
C4 C5 1.467(4) .
C5 C6 1.392(4) .
C5 C7 1.396(4) 3_666
C6 C7 1.381(4) .
C7 C5 1.396(4) 3_666
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
S1 C1 C2 C3 -0.3(3) . .
S1 C4 C5 C6 6.7(4) . .
S1 C4 C5 C7 -173.3(2) . 3_666
F1 C6 C7 F2 0.9(4) . .
F1 C6 C7 C5 179.6(2) . 3_666
C1 S1 C4 C3 -0.8(2) . .
C1 S1 C4 C5 177.8(2) . .
C1 C2 C3 C4 -0.3(4) . .
C2 C3 C4 S1 0.7(3) . .
C2 C3 C4 C5 -177.7(3) . .
C3 C4 C5 C6 -175.1(3) . .
C3 C4 C5 C7 4.9(4) . 3_666
C4 S1 C1 C2 0.6(2) . .
C4 C5 C6 F1 0.4(4) . .
C4 C5 C6 C7 -179.9(3) . .
C5 C6 C7 F2 -178.8(2) . .
C5 C6 C7 C5 -0.2(5) . 3_666
C7 C5 C6 F1 -179.6(2) 3_666 .
C7 C5 C6 C7 0.1(4) 3_666 .
