Selective Synthesis of 2-Substituted and 1,2-Disubstituted Benzimidazoles Directly from Aromatic Diamines and Alcohols Catalyzed by Molecularly Defined Nonphosphine Manganese(I) Complex.
Das, Kalicharan; Mondal, Avijit; Srimani, Dipankar; The Journal of organic chemistry 83 (2018) 9553–9560; doi:10.1021/acs.joc.8b01316

data_4035379
_publ_section_title
;
 Selective Synthesis of 2-Substituted and 1,2-Disubstituted Benzimidazoles
 Directly from Aromatic Diamines and Alcohols Catalyzed by Molecularly
 Defined Nonphosphine Manganese(I) Complex.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9553
_journal_page_last               9560
_journal_paper_doi               10.1021/acs.joc.8b01316
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C13 H16 Br Mn N2 O3 S'
_chemical_formula_weight         415.19
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.629(18)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9663(16)
_cell_length_b                   14.830(3)
_cell_length_c                   14.187(2)
_cell_measurement_reflns_used    734
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.0360
_cell_measurement_theta_min      3.7670
_cell_volume                     1664.9(5)
_computing_cell_refinement       NA
_computing_data_collection       NA
_computing_data_reduction        NA
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.2760
_diffrn_measured_fraction_theta_full 0.9963
_diffrn_measured_fraction_theta_max 0.8816
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1090
_diffrn_reflns_av_sigmaI/netI    0.1978
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            6005
_diffrn_reflns_theta_full        26.3154
_diffrn_reflns_theta_max         24.50
_diffrn_reflns_theta_min         2.92
_diffrn_standards_number         7522
_exptl_absorpt_coefficient_mu    3.327
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29978
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.656
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       dumble
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_refine_diff_density_max         0.973
_refine_diff_density_min         -0.500
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.903
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2766
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.903
_refine_ls_R_factor_all          0.2034
_refine_ls_R_factor_gt           0.0923
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0040P)^2^+25.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1579
_refine_ls_wR_factor_ref         0.2151
_reflns_number_gt                1123
_reflns_number_total             2766
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b01316_si_002.cif
_cod_data_source_block           exp_4204
_cod_database_code               4035379