Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and benzothiazoles <i>via</i> condensation of diamines or amino(thio)phenols with CF<sub>3</sub>CN.
Lin, Bo; Yao, Yunfei; Wu, Minze; Qin, Lu; Chen, Shouxiong; You, Yi; Weng, Zhiqiang; Organic & biomolecular chemistry 21 (2023) 4788–4793; doi:10.1039/d3ob00517h

data_7159364
_publ_section_title
;
 Synthesis of 2-trifluoromethyl benzimidazoles, benzoxazoles, and
 benzothiazoles <i>via</i> condensation of diamines or amino(thio)phenols
 with CF<sub>3</sub>CN.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              4788
_journal_page_last               4793
_journal_paper_doi               10.1039/d3ob00517h
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H10 F6 N4'
_chemical_formula_sum            'C16 H10 F6 N4'
_chemical_formula_weight         372.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2023-03-24
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-03-24 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.958(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.1807(3)
_cell_length_b                   21.2316(5)
_cell_length_c                   16.3707(4)
_cell_measurement_reflns_used    3683
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.8110
_cell_measurement_theta_min      3.4740
_cell_volume                     3418.67(16)
_computing_cell_refinement       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.121a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.988
_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     64.00  93.00   0.50    2.00    --   42.40  54.00 162.00   58
  2  \w     19.00  45.00   0.50    2.00    --   42.40  54.00 162.00   52
  3  \w     28.00 117.00   0.50    2.00    --   93.70 -54.00  18.00  178
  4  \w     85.00 139.00   0.50    2.00    --   93.70  54.00 162.00  108
  5  \w     17.00  71.00   0.50    2.00    --   42.40  82.00  30.00  108
  6  \w     17.00  85.00   0.50    2.00    --   42.40  77.00 -90.00  136
  7  \w     44.00  70.00   0.50    2.00    --   42.40  82.00  90.00   52
  8  \w    106.00 131.00   0.50    2.00    --   42.40  82.00  30.00   50
  9  \w     92.00 127.00   0.50    2.00    --   42.40  77.00 -90.00   70
 10  \w    -47.00   4.00   0.50    2.00    --   42.40 -77.00 -60.00  102
 11  \w     43.00  68.00   0.50    2.00    --   42.40 -82.00   0.00   50
 12  \w    101.00 126.00   0.50    2.00    --   42.40  82.00  90.00   50
 13  \w    -33.00  28.00   0.50    2.00    --   42.40 -82.00   0.00  122
 14  \w     16.00  41.00   0.50    2.00    --   42.40  82.00  90.00   50
 15  \w    -27.00  -2.00   0.50    2.00    --   42.40 -54.00  18.00   50
 16  \w     23.00  60.00   0.50    2.00    --   42.40 -77.00 -60.00   74
 17  \w     55.00 118.00   0.50    2.00    --   93.70 -59.00-180.00  126
 18  \w      4.00  29.00   0.50    2.00    --   93.70 -59.00-180.00   50
 19  \w      5.00 120.00   0.50    2.00    --   93.70 -82.00  30.00  230
 20  \w     68.00  93.00   0.50    2.00    --   93.70  33.00-120.00   50
 21  \w      7.00  68.00   0.50    2.00    --   93.70 -50.00 -60.00  122
 22  \w     35.00  67.00   0.50    2.00    --   93.70 -68.00 150.00   64
 23  \w    100.00 183.00   0.50    2.00    --   93.70  42.00 -90.00  166
 24  \w     73.00  98.00   0.50    2.00    --   93.70 -59.00 -60.00   50
 25  \w      6.00  37.00   0.50    2.00    --   93.70 -59.00 -60.00   62
 26  \w    100.00 165.00   0.50    2.00    --   93.70  33.00-120.00  130
 27  \w     12.00 106.00   0.50    2.00    --   93.70 -33.00-180.00  188
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type
'XtaLAB Pro II AFC12 (RINC): Kappa dual home/near'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1482707000
_diffrn_orient_matrix_UB_12      -0.0001264000
_diffrn_orient_matrix_UB_13      0.0066385000
_diffrn_orient_matrix_UB_21      -0.0383816000
_diffrn_orient_matrix_UB_22      0.0476418000
_diffrn_orient_matrix_UB_23      -0.0733101000
_diffrn_orient_matrix_UB_31      -0.0330762000
_diffrn_orient_matrix_UB_32      -0.0547126000
_diffrn_orient_matrix_UB_33      -0.0637631000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8658
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         68.229
_diffrn_reflns_theta_min         3.485
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.30730
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.41.121a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic light colourless'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.447
_exptl_crystal_description       block
_exptl_crystal_F_000             1504
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.574
_refine_diff_density_min         -0.460
_refine_diff_density_rms         0.106
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     239
_refine_ls_number_reflns         3105
_refine_ls_number_restraints     48
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.1253
_refine_ls_R_factor_gt           0.0998
_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^)+(0.1725P)^2^+5.1864P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2869
_refine_ls_wR_factor_ref         0.3057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2108
_reflns_number_total             3105
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00517h2.cif
_cod_data_source_block           yyf20230323-n-ph_auto
_cod_depositor_comments
'Adding full bibliography for 7159364--7159365.cif.'
_cod_original_cell_volume        3418.66(16)
_cod_database_code               7159364
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNF
_shelx_estimated_absorpt_t_max   0.889
_shelx_estimated_absorpt_t_min   0.889
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(F001) \\sim Ueq, Uanis(F006) \\sim Ueq, Uanis(C00O) \\sim Ueq,
Uanis(F008) \\sim Ueq, Uanis(F00A) \\sim Ueq, Uanis(F00F) \\sim Ueq,
Uanis(C00M) \\sim Ueq, Uanis(F0) \\sim Ueq, : with sigma of 0.1 and sigma for
terminal atoms of 0.2
3.a Aromatic/amide H refined with riding coordinates:
 N002(H002), C00E(H00E), C00H(H00H), C00I(H00I), C00M(H00M), C00O(H00O),
 C1(H1), C2(H2), C3(H3)
;
_shelx_res_checksum              39510
_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 2.363
_oxdiff_exptl_absorpt_empirical_full_min 0.393