Rh(III)-Catalyzed Cascade C-H Activation/Amination Enables the Synthesis of 1,2-Disubstituted Benzimidazoles from Amidines and Arynes
Xu, Fen; Zhang, Shi-Yu; Huo, Jia-Qi; Zeng, Fan-Wang; Zhou, Fu-Kang; Barboni, Luciano; Organic & Biomolecular Chemistry  (2025) –; doi:10.1039/D6OB00074F

data_7161092
_publ_section_title
;
 Rh(III)-catalyzed cascade C-H activation/amination enables the synthesis
 of 1,2-disubstituted benzimidazoles from amidines and arynes.
;
_journal_issue                   15
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              3218
_journal_page_last               3222
_journal_paper_doi               10.1039/d6ob00074f
_journal_volume                  24
_journal_year                    2026
_chemical_formula_moiety         '0.62(C19 H14 N2)'
_chemical_formula_sum            'C11.69 H8.62 N1.23'
_chemical_formula_weight         166.35
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2026-01-06
_audit_creation_method
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314)
;
_audit_update_record
;
2026-01-09 deposited with the CCDC.	2026-03-25 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.687(7)
_cell_angle_gamma                90
_cell_formula_units_Z            13
_cell_length_a                   10.2133(6)
_cell_length_b                   16.6796(9)
_cell_length_c                   17.8803(12)
_cell_measurement_reflns_used    3038
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      28.8280
_cell_measurement_theta_min      4.6760
_cell_volume                     2932.5(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3031
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.829
_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    -59.00   3.00   1.00   15.53    --   11.93 -57.00-120.00   62
  2  \w    -29.00  88.00   1.00   15.53    --   11.93  19.00  30.00  117
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0719827000
_diffrn_orient_matrix_UB_12      0.0019109000
_diffrn_orient_matrix_UB_13      -0.0131729000
_diffrn_orient_matrix_UB_21      -0.0004790000
_diffrn_orient_matrix_UB_22      -0.0345850000
_diffrn_orient_matrix_UB_23      -0.0231534000
_diffrn_orient_matrix_UB_31      -0.0049222000
_diffrn_orient_matrix_UB_32      -0.0246565000
_diffrn_orient_matrix_UB_33      0.0314367000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0143
_diffrn_reflns_av_unetI/netI     0.0220
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            6869
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.785
_diffrn_reflns_theta_min         3.401
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       prism
_exptl_crystal_F_000             1136
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.030
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.181
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0466
_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^)+(0.1000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1636
_refine_ls_wR_factor_ref         0.1766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2626
_reflns_number_total             3483
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d6ob00074f2.cif
_cod_data_source_block           xf-20210104
_cod_depositor_comments
'Adding full bibliography for 7161092--7161093.cif.'
_cod_database_code               7161092
_shelxl_version_number           2013-2
_reflns_odcompleteness_completeness 99.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C9(H9), C15(H15), C19(H19), C3(H3), C11(H11), C18(H18), C10(H10),
 C4(H4), C16(H16), C1(H1), C2(H2), C12(H12), C17(H17)
;
_shelx_res_checksum              23391
_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 1.237
_oxdiff_exptl_absorpt_empirical_full_min 0.812