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_1554710
_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 H8 F2 S2'
_chemical_formula_sum            'C14 H8 F2 S2'
_chemical_formula_weight         278.32
_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     direct
_audit_creation_date             2017-05-25
_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                 94.273(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.4893(9)
_cell_length_b                   3.8493(4)
_cell_length_c                   19.835(2)
_cell_measurement_reflns_used    5897
_cell_measurement_temperature    110.0
_cell_measurement_theta_max      27.512
_cell_measurement_theta_min      2.728
_cell_volume                     570.23(11)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      110.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.079
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_number            976
_diffrn_reflns_point_group_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        24.977
_diffrn_reflns_theta_max         24.977
_diffrn_reflns_theta_min         2.727
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.468
_exptl_absorpt_correction_T_max  0.7314
_exptl_absorpt_correction_T_min  0.4838
_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 0.1756 before and 0.0872 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1821 before and 0.0930 after correction.
 The Ratio of minimum to maximum transmission is 0.54.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 13183 reflections, Rint = 0.0842
 (10786 with I > 3sig(I), Rint = 0.0823)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.512
_exptl_crystal_size_mid          0.423
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     107
_refine_ls_number_reflns         976
_refine_ls_number_restraints     220
_refine_ls_restrained_S_all      1.224
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0787
_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^+2.8130P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1626
_refine_ls_wR_factor_ref         0.1703
_reflns_Friedel_coverage         0.000
_reflns_number_gt                854
_reflns_number_total             976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00044e2.cif
_cod_data_source_block           f2p
_cod_database_code               1554710
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Shared sites
{C4, C4A}
3. Uiso/Uaniso restraints and constraints
C4 \\sim C5 \\sim C6 \\sim C7 \\sim S8 \\sim C4A \\sim C5A \\sim C6A \\sim C7A
\\sim S8A: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C4) = Uanis(C4A)
Uanis(S8) = Uanis(C5A)
Uanis(C5) = Uanis(S8A)
4. Rigid body (RIGU) restrains
 C4, C5, C6, C7, S8, C4A, C5A, C6A, C7A, S8A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
5. Same fragment restrains
{C4, C5, C6, C7, S8} sigma for 1-2: 0.02, 1-3: 0.04
as
{C4A, C5A, C6A, C7A, S8A}
6. Others
 Sof(C4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(S8A)=1-
 FVAR(1)
 Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7)=Sof(S8)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C7(H7), C5A(H5A), C6A(H6A), C7A(H7A)
;
_shelx_res_checksum              43681
_shelx_hkl_checksum              7566
_olex2_submission_special_instructions 'No special instructions were received'