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_1554711
_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         '1.4(C8.54 H4.27 F0.71 N1.42 S1.42)'
_chemical_formula_sum            'C12 H6 F N2 S2'
_chemical_formula_weight         261.31
_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     direct
_audit_creation_date             2017-08-18
_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                 95.890(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.9315(6)
_cell_length_b                   4.9497(5)
_cell_length_c                   18.794(2)
_cell_measurement_reflns_used    3497
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.701
_cell_measurement_theta_min      3.272
_cell_volume                     548.86(10)
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.964
_diffrn_measured_fraction_theta_max 0.964
_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  0.0586
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            1289
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        22.487
_diffrn_reflns_theta_max         22.487
_diffrn_reflns_theta_min         2.179
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.472
_exptl_absorpt_correction_T_max  0.745
_exptl_absorpt_correction_T_min  0.558
_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 0.1439 before and 0.0601 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 0.1654 before and 0.0805 after correction.
 The Ratio of minimum to maximum transmission is 0.76.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 10163 reflections, Rint = 0.0586
 (7686 with I > 3sig(I), Rint = 0.0567)
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_description       block
_exptl_crystal_F_000             266
_exptl_crystal_size_max          0.222
_exptl_crystal_size_mid          0.135
_exptl_crystal_size_min          0.094
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.090
_refine_ls_extinction_coef       0.031(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.174
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1289
_refine_ls_number_restraints     468
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0928
_refine_ls_R_factor_gt           0.0818
_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^)+(0.0262P)^2^+1.6061P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1515
_refine_ls_wR_factor_ref         0.1590
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1156
_reflns_number_total             1289
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00044e2.cif
_cod_data_source_block           4
_cod_original_cell_volume        548.85(10)
_cod_database_code               1554711
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.902
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.860(3)
 0.140(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 C3-C1_$1 \\sim C2_$1-C1_$1 \\sim C3_$1-C2_$1 \\sim C3_$1-C1 \\sim C2-C1 \\sim
C3-C2 \\sim C3A-C1A_$1
 \\sim C2A_$1-C1A_$1 \\sim C3A_$1-C2A_$1 \\sim C3A_$1-C1A \\sim C2A-C1A \\sim
C3A-C2A
 with sigma of 0.005
4. Uiso/Uaniso restraints and constraints
C1 \\sim C2 \\sim C3 \\sim C4 \\sim C5 \\sim C6 \\sim F3 \\sim N2 \\sim S1
\\sim C1A \\sim C2A \\sim C3A \\sim C4A \\sim C5A \\sim C6A \\sim F3A \\sim N2A
\\sim S1A: within 2A with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(N2) = Uanis(N2A)
Uanis(S1A) = Uanis(S1)
Uanis(F3) = Uanis(F3A)
Uanis(C2) = Uanis(C2A)
Uanis(C1) = Uanis(C1A)
Uanis(C3) = Uanis(C3A)
5. Rigid body (RIGU) restrains
 C1, C2, C3, C4, C5, C6, F3, N2, S1, C1A, C2A, C3A, C4A, C5A, C6A, F3A, N2A, S1A
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
6. Same fragment restrains
{C1, C2, C3, C4, C5, C6, F3, N2, S1} sigma for 1-2: 0.005, 1-3: 0.04
as
{C1A, C2A, C3A, C4A, C5A, C6A, F3A, N2A, S1A}
7. Others
 Sof(C1A)=Sof(H1A)=Sof(C2A)=Sof(C3A)=Sof(C4A)=Sof(C5A)=Sof(H5A)=Sof(C6A)=
 Sof(H6A)=Sof(N2A)=Sof(S1A)=1-FVAR(1)
 Sof(F3A)=0.5*(1-FVAR(2))
 Sof(F3)=0.5*FVAR(2)
 Sof(C1)=Sof(H1)=Sof(C2)=Sof(C3)=Sof(C4)=Sof(C5)=Sof(H5)=Sof(C6)=Sof(H6)=
 Sof(N2)=Sof(S1)=FVAR(1)
8.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C6(H6), C1A(H1A), C5A(H5A), C6A(H6A)
;
_shelx_res_checksum              81644
_shelx_hkl_checksum              81650
_olex2_submission_special_instructions 'No special instructions were received'