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_1554722
_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_absolute_configuration unk
_chemical_formula_moiety         'C12 H8 N2 S2'
_chemical_formula_sum            'C12 H8 N2 S2'
_chemical_formula_weight         244.32
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-06-21
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_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
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.9825(7)
_cell_length_b                   9.7302(4)
_cell_length_c                   13.6524(4)
_cell_measurement_reflns_used    9889
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      65.290
_cell_measurement_theta_min      5.536
_cell_volume                     2123.12(14)
_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      100.0
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_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  0.0289
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10935
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        65.259
_diffrn_reflns_theta_max         65.259
_diffrn_reflns_theta_min         6.234
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.284
_exptl_absorpt_correction_T_max  0.7526
_exptl_absorpt_correction_T_min  0.5917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0983 before and 0.0489 after correction. The Ratio of minimum to maximum transmission is 0.7862. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_description       plate
_exptl_crystal_F_000             1008
_exptl_crystal_size_max          0.113
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.50(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.104
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         904
_refine_ls_number_restraints     510
_refine_ls_restrained_S_all      1.115
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0344P)^2^+2.5140P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0621
_reflns_Friedel_coverage         0.911
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                882
_reflns_number_total             904
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00044e2.cif
_cod_data_source_block           posa
_cod_database_code               1554722
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.865
_shelx_estimated_absorpt_t_min   0.643
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.50(4)
 0.50(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3. Restrained distances
 N2-C10A \\sim N2A-C10 \\sim N1-C1A \\sim N1A-C1
 with sigma of 0.01
 S2-C10 \\sim S2A-C10A \\sim S1-C1 \\sim S1A-C1A
 with sigma of 0.01
 N1-C2 \\sim N1A-C2A \\sim N2A-C9A \\sim N2-C9
 with sigma of 0.01
 S1-C3 \\sim S1A-C3 \\sim S2-C8 \\sim S2A-C8
 with sigma of 0.01
 C3-C2A \\sim C3-C2 \\sim C9A-C8 \\sim C9-C8
 with sigma of 0.01
 C4-C3 \\sim C8-C7
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 2A with sigma of 0.005 and sigma
for terminal atoms of 0.01
Uanis(S2) = Uanis(C9)
Uanis(C2) = Uanis(S1)
Uanis(N1) = Uanis(C1)
Uanis(C10) = Uanis(N2)
Uanis(N2A) = Uanis(C10A) = Uanis(C10) = Uanis(N2)
Uanis(S2) = Uanis(C9) = Uanis(C9A) = Uanis(S2A)
Uanis(C1) = Uanis(N1A) = Uanis(N1) = Uanis(C1A)
Uanis(S1) = Uanis(C2A) = Uanis(C2) = Uanis(S1A)
Uanis(C7) = Uanis(C8)
5. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
6. Others
 Fixed Sof: S1(0.25) C1(0.25) H1(0.25) N1A(0.25) C2A(0.25) H2A(0.25) S2(0.25)
 C10(0.25) H10(0.25) N2A(0.25) C9A(0.25) H9A(0.25) C5(0.5) H5(0.5) C6(0.5)
 H6(0.5) C6A(0.5) H6A(0.5) C5A(0.5) H5A(0.5) C2(0.25) H2(0.25) N1(0.25)
 C1A(0.25) H1A(0.25) S1A(0.25) S2A(0.25) C10A(0.25) H10A(0.25) N2(0.25)
 C9(0.25) H9(0.25)
7.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2A(H2A), C10(H10), C9A(H9A), C5(H5), C6(H6), C6A(H6A), C5A(H5A),
 C2(H2), C1A(H1A), C10A(H10A), C9(H9)
;
_shelx_res_checksum              54048
_shelx_hkl_checksum              63301
_olex2_submission_special_instructions 'No special instructions were received'