Synthesis, characterization and crystal structures of novel fluorinated di(thiazolyl)benzene derivatives
Barłóg, Maciej; Kulai, Ihor; Ji, Xiaozhou; Bhuvanesh, Nattamai; Dey, Somnath; Sliwinski, Eric Pierre; Bazzi, Hassan S.; Fang, Lei; Al-Hashimi, Mohammed; Organic Chemistry Frontiers 6 (2019) 780–; doi:10.1039/C9QO00044E

data_1554713
_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       '\f and \w 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 \l/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 \l/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/[\s^2^(Fo^2^)+(0.0347P)^2^+1.3912P] where P=(Fo^2^+2Fc^2^)/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 > 2\s(I)'
_cod_data_source_file            c9qo00044e2.cif
_cod_data_source_block           f4p
_cod_database_code               1554713
_shelx_shelxl_version_number     2014/7
_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)
;
_shelx_res_checksum              56815
_shelx_hkl_checksum              36489
_olex2_submission_special_instructions 'No special instructions were received'