Tunable base-controlled chemoselective synthesis of trifluoromethyl-containing <i>N</i>-substituted benzimidazole-2-thiones and monofluorinated 4<i>H</i>-benzo[4,5]imidazo[2,1-<i>b</i>][1,3]thiazine.
Deng, Yupian; Qian, Yuhao; Huang, Jiaqi; Sun, Zhudi; Zhuge, Ronghua; Huang, Qingchun; Cao, Song; Organic & biomolecular chemistry 23 (2025) 1588–1595; doi:10.1039/d4ob01999g

data_7160309
_publ_section_title
;
 Tunable base-controlled chemoselective synthesis of
 trifluoromethyl-containing <i>N</i>-substituted benzimidazole-2-thiones
 and monofluorinated
 4<i>H</i>-benzo[4,5]imidazo[2,1-<i>b</i>][1,3]thiazine.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              1588
_journal_page_last               1595
_journal_paper_doi               10.1039/d4ob01999g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C18 H16 F3 N S2'
_chemical_formula_sum            'C18 H16 F3 N S2'
_chemical_formula_weight         367.44
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2024-07-29
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-11-26 deposited with the CCDC.	2024-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                78.756(11)
_cell_angle_beta                 87.061(10)
_cell_angle_gamma                87.682(9)
_cell_formula_units_Z            4
_cell_length_a                   9.8048(11)
_cell_length_b                   9.9049(12)
_cell_length_c                   18.453(3)
_cell_measurement_reflns_used    2032
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.7860
_cell_measurement_theta_min      2.7510
_cell_volume                     1754.5(4)
_computing_cell_refinement       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_collection       'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.42.99a (Rigaku OD, 2023)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -37.00  46.00   1.00    5.00    --   16.96 -77.00  60.00   83
  2  \w    -48.00  31.00   1.00    5.00    --   16.96 -57.00-180.00   79
  3  \w    -51.00  32.00   1.00    5.00    --   16.96 -57.00 -60.00   83
  4  \w     -2.00  46.00   1.00    5.00    --   16.96  57.00 -60.00   48
  5  \w     50.00  84.00   1.00    5.00    --   16.96  57.00 -60.00   34
  6  \w    -39.00  10.00   1.00    5.00    --  -17.43 -77.00  90.00   49
  7  \w    -23.00  10.00   1.00    5.00    --  -17.43 -77.00 -60.00   33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0506745000
_diffrn_orient_matrix_UB_12      -0.0524128000
_diffrn_orient_matrix_UB_13      0.0103651000
_diffrn_orient_matrix_UB_21      0.0507145000
_diffrn_orient_matrix_UB_22      0.0436649000
_diffrn_orient_matrix_UB_23      -0.0196049000
_diffrn_orient_matrix_UB_31      0.0106038000
_diffrn_orient_matrix_UB_32      0.0261211000
_diffrn_orient_matrix_UB_33      0.0323600000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0769
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12956
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.253
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.332
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54419
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.99a (Rigaku Oxford Diffraction, 2023)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         6131
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1150
_refine_ls_R_factor_gt           0.0600
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0312P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0905
_refine_ls_wR_factor_ref         0.1111
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3634
_reflns_number_total             6131
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ob01999g2.cif
_cod_data_source_block           exp_14554_auto
_cod_depositor_comments
'Adding full bibliography for 7160308--7160309.cif.'
_cod_database_code               7160309
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.971
_shelx_estimated_absorpt_t_min   0.937
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C23(H23)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C20(H20A,H20B), C21(H21A,H21B),
 C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C10(H10), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16),
 C17(H17), C25(H25), C26(H26), C28(H28), C29(H29), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.538
_oxdiff_exptl_absorpt_empirical_full_min 0.683