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_1554718
_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 H5 F N2 S2'
_chemical_formula_sum            'C12 H5 F N2 S2'
_chemical_formula_weight         260.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-04-18
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_audit_update_record
;
2018-07-19 deposited with the CCDC.
2019-01-30 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.338(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   3.8093(3)
_cell_length_b                   6.6644(4)
_cell_length_c                   21.5126(15)
_cell_measurement_reflns_used    5991
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.103
_cell_measurement_theta_min      4.122
_cell_volume                     544.57(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_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_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.992
_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  0.0605
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            8852
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.212
_diffrn_reflns_theta_min         4.122
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.358
_exptl_absorpt_correction_T_max  0.5856
_exptl_absorpt_correction_T_min  0.4198
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1319 before and 0.0823 after correction. The Ratio of minimum to maximum transmission is 0.7169. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.049
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.567
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.314
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     86
_refine_ls_number_reflns         1034
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.313
_refine_ls_R_factor_all          0.0979
_refine_ls_R_factor_gt           0.0846
_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^)+3.4260P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1564
_refine_ls_wR_factor_ref         0.1609
_reflns_Friedel_coverage         0.000
_reflns_number_gt                885
_reflns_number_total             1034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00044e2.cif
_cod_data_source_block           f1s
_cod_database_code               1554718
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.862
_shelx_estimated_absorpt_t_min   0.815
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 F1A-C2 \\sim F1-C1
 with sigma of 0.005
3. Uiso/Uaniso restraints and constraints
Uanis(F1) = Uanis(F1A)
4. Others
 Sof(F1A)=Sof(H1)=0.5*(1-FVAR(2))
 Sof(F1)=Sof(H2)=0.5*FVAR(2)
5.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C5(H5), C6(H6)
;
_shelx_res_checksum              5785
_shelx_hkl_checksum              67722
_olex2_submission_special_instructions 'No special instructions were received'