Selective C-H trifluoromethylation of benzimidazoles through photoredox catalysis.
Gao, Guo-Lin; Yang, Chao; Xia, Wujiong; Chemical communications (Cambridge, England) 53 (2017) 1041–1044; doi:10.1039/c6cc08975e

data_7119296
_publ_section_title
;
 Selective C-H trifluoromethylation of benzimidazoles through photoredox
 catalysis.
;
_journal_issue                   6
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              1041
_journal_page_last               1044
_journal_paper_doi               10.1039/c6cc08975e
_journal_volume                  53
_journal_year                    2017
_chemical_formula_moiety         'C12 H11 F3 N2 O2'
_chemical_formula_sum            'C12 H11 F3 N2 O2'
_chemical_formula_weight         272.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_block_doi                 10.5517/ccdc.csd.cc1mwlgk
_audit_creation_date             2016-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-11-10 deposited with the CCDC.
2016-12-12 downloaded from the CCDC.
;
_cell_angle_alpha                102.706(11)
_cell_angle_beta                 105.918(10)
_cell_angle_gamma                97.358(10)
_cell_formula_units_Z            2
_cell_length_a                   7.2208(7)
_cell_length_b                   9.3833(13)
_cell_length_c                   9.5826(11)
_cell_measurement_reflns_used    1549
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.4560
_cell_measurement_theta_min      3.3650
_cell_volume                     596.67(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9737
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_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      9.00  67.00   1.00    1.00    --   18.81  37.00  60.00   58
  2  \w      8.00  88.00   1.00    1.00    --   18.81  57.00 -30.00   80
  3  \w    -11.00  16.00   1.00    1.00    --  -19.74 -94.00 -37.00   27
  4  \w    -29.00  40.00   1.00    1.00    --   18.81 -57.00  60.00   69
  5  \w    -34.00  39.00   1.00    1.00    --   18.81 -57.00-150.00   73
  6  \w    -20.00  60.00   1.00    1.00    --   18.81 -99.00-180.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0034559000
_diffrn_orient_matrix_UB_12      0.0699042000
_diffrn_orient_matrix_UB_13      -0.0164275000
_diffrn_orient_matrix_UB_21      0.1032125000
_diffrn_orient_matrix_UB_22      0.0224960000
_diffrn_orient_matrix_UB_23      0.0344784000
_diffrn_orient_matrix_UB_31      0.0144184000
_diffrn_orient_matrix_UB_32      -0.0293996000
_diffrn_orient_matrix_UB_33      -0.0701596000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            3924
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.348
_diffrn_reflns_theta_max         25.348
_diffrn_reflns_theta_min         2.995
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65465
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.515
_exptl_crystal_description       block
_exptl_crystal_F_000             280
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.094(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2172
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0553
_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^)+(0.0754P)^2^+0.2080P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1590
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1642
_reflns_number_total             2172
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6cc08975e2.cif
_cod_data_source_block           ggl20160418-1
_cod_depositor_comments
'Adding full bibliography for 7119293--7119296.cif.'
_cod_database_code               7119296
_chemical_oxdiff_formula         'C H N O F'
_reflns_odcompleteness_completeness 99.55
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C12(H12A,H12B,H12C)
;
_shelx_res_checksum              6324
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-05-11
_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 1.368
_oxdiff_exptl_absorpt_empirical_full_min 0.586