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_7159365
_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         'C8 H8 Br F3 N4'
_chemical_formula_sum            'C8 H8 Br F3 N4'
_chemical_formula_weight         297.09
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yc'
_space_group_name_H-M_alt        'P 1 2/c 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
;
2023-03-25 deposited with the CCDC.	2023-05-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.0520(10)
_cell_angle_gamma                90
_cell_formula_units_Z            32
_cell_length_a                   29.3359(4)
_cell_length_b                   9.24130(10)
_cell_length_c                   38.2126(6)
_cell_measurement_temperature    293(2)
_cell_volume                     10359.5(2)
_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_measured_fraction_theta_full 0.919
_diffrn_measured_fraction_theta_max 0.910
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0752
_diffrn_reflns_av_unetI/netI     0.0868
_diffrn_reflns_Laue_measured_fraction_full 0.919
_diffrn_reflns_Laue_measured_fraction_max 0.910
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            38924
_diffrn_reflns_point_group_measured_fraction_full 0.919
_diffrn_reflns_point_group_measured_fraction_max 0.910
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.275
_diffrn_reflns_theta_min         2.312
_exptl_absorpt_coefficient_mu    4.544
_exptl_absorpt_correction_type   none
_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    1.524
_exptl_crystal_description       plate
_exptl_crystal_F_000             4672
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         2.080
_refine_diff_density_min         -2.008
_refine_diff_density_rms         0.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.414
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1184
_refine_ls_number_reflns         17263
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.414
_refine_ls_R_factor_all          0.1346
_refine_ls_R_factor_gt           0.1209
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3440
_refine_ls_wR_factor_ref         0.3618
_reflns_Friedel_coverage         0.000
_reflns_number_gt                13394
_reflns_number_total             17263
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob00517h2.cif
_cod_data_source_block           1111
_cod_depositor_comments
'Adding full bibliography for 7159364--7159365.cif.'
_cod_database_code               7159365
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.805
_shelx_estimated_absorpt_t_min   0.659
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups, All N(H,H,H,H,H)
  groups, All Br(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N00C(H00C), N00H(H00H), N00Z(H00Z), N018(H01A,H01B), N01K(H01N,H01O),
 N01R(H01E,H01F), N01X(H01C,H01D), N1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N009(H009), N00A(H00A), N00E(H00E), N00K(H00K), N00M(H00M), N00Q(H00Q),
 N00V(H00V), N00W(H00W), C017(H017), C01G(H01G), C01P(H01P), C020(H020),
 C021(H021), C02L(H02L), C02X(H02X), C035(H035)
2.c X=CH2 refined with riding coordinates:
 N011(H01H,H01I), N01A(H01L,H01M), N01W(H01J,H01K)
2.d Idealised Me refined as rotating group:
 C02T(H02A,H02B,H02C), C02V(H02D,H02E,H02F), C02W(H02G,H02H,H02I), C02Z(H02J,
 H02K,H02M), C036(H03D,H03E,H03F), C039(H03A,H03B,H03C), C03H(H03G,H03H,H03I),
 C03I(H03J,H03K,H03L)
;
_shelx_res_checksum              78871
_olex2_submission_special_instructions 'No special instructions were received'