Copper-catalyzed synthesis of polysubstituted benzimidazoles: an efficient one-pot synthetic approach to <i>N</i>-enylated benzimidazoles.
Mohaghegh, Farid; Jafarpour, Farnaz; Organic & biomolecular chemistry 23 (2025) 7742–7745; doi:10.1039/d5ob00418g

data_7160657
_publ_section_title
;
 Copper-catalyzed synthesis of polysubstituted benzimidazoles: an
 efficient one-pot synthetic approach to <i>N</i>-enylated benzimidazoles.
;
_journal_issue                   34
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              7742
_journal_page_last               7745
_journal_paper_doi               10.1039/d5ob00418g
_journal_volume                  23
_journal_year                    2025
_chemical_formula_moiety         'C30 H22 N2'
_chemical_formula_sum            'C30 H22 N2'
_chemical_formula_weight         410.49
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2021-05-03
_audit_creation_method
;

;
_audit_update_record
;
2025-03-08 deposited with the CCDC.	2025-08-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.69(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.024(2)
_cell_length_b                   20.330(4)
_cell_length_c                   11.444(2)
_cell_measurement_reflns_used    13784
_cell_measurement_temperature    290
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.3
_cell_volume                     2255.9(8)
_computing_cell_refinement       'Automar software package (3.3a, 2015)'
_computing_data_collection       'MAR345 dtb Program (1.24-4, 2013)'
_computing_data_reduction        'Automar software package (3.3a, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'PLATON (2018)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      290
_diffrn_detector                 'image-plate detector'
_diffrn_detector_area_resol_mean 0.81
_diffrn_detector_type            MAR345-dtb
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device       'one-circle diffractometer'
_diffrn_measurement_device_type  MAR-345dtb
_diffrn_measurement_method       'image-plate detector - phi oscillation'
_diffrn_radiation_monochromator  mirrors
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13784
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.327
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_target            Mo
_exptl_absorpt_coefficient_mu    0.071
_exptl_absorpt_correction_T_max  1.07265
_exptl_absorpt_correction_T_min  0.95457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'R.H. Blessing, Acta Crystallogr., Sect A 1995, 51, 33-38'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.142
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.055(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         3896
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.099
_refine_ls_R_factor_all          0.0726
_refine_ls_R_factor_gt           0.0642
_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^)+(0.0824P)^2^+0.6959P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.1816
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3393
_reflns_number_total             3896
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ob00418g2.cif
_cod_data_source_block           2_pl
_cod_depositor_comments          'Adding full bibliography for 7160657.cif.'
_cod_database_code               7160657
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.972
_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C10(H10), C12(H12), C14(H14), C18(H18), C20(H20), C22(H22),
 C24(H24), C28(H28), C7(H7), C15(H15), C2(H2), C9(H9), C5(H5), C21(H21),
 C23(H23), C3(H3), C25(H25)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C)
;
_submission_special_instructions 'No special instructions were received'