A Protocol to 2-Aminobenzimidazoles via Copper-Catalyzed Cascade Addition and Cyclization of o-Haloanilines and Carbodiimides
Fei Wang; Shangjun Cai; Qian Liao; Chanjuan Xi; Journal of Organic Chemistry 76 (2011) 3174–3180; doi:10.1021/jo200014v

data_4026232
_publ_contact_author
;
Dr. Chanjuan Xi
Department of Chemistry, Tsinghua University
Beijing 100084
China
;
_publ_section_title
;
 A Protocol to 2-Aminobenzimidazoles via Copper-Catalyzed Cascade Addition
 and Cyclization of o-Haloanilines and Carbodiimides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3174
_journal_page_last               3180
_journal_paper_doi               10.1021/jo200014v
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C19 H27 N3 O0'
_chemical_formula_weight         297.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           96
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P 4nw 2abw'
_symmetry_space_group_name_H-M   'P 43 21 2'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.1671(19)
_cell_length_b                   13.1671(19)
_cell_length_c                   19.597(4)
_cell_measurement_reflns_used    5081
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.3487
_cell_measurement_theta_min      1.5466
_cell_volume                     3397.6(10)
_computing_cell_refinement       'Bruker XSCANS'
_computing_data_collection       'Bruker XSCANS'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_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  0.0513
_diffrn_reflns_av_sigmaI/netI    0.0699
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6781
_diffrn_reflns_theta_full        25.34
_diffrn_reflns_theta_max         25.34
_diffrn_reflns_theta_min         1.86
_diffrn_standards_decay_%        none
_diffrn_standards_interval_count none
_diffrn_standards_interval_time  none
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_T_max  0.9938
_exptl_absorpt_correction_T_min  0.9631
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.163
_exptl_crystal_description       needle
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   10(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         3098
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.1037
_refine_ls_R_factor_gt           0.0877
_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^)+(0.0566P)^2^+1.5907P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1819
_refine_ls_wR_factor_ref         0.1905
_reflns_number_gt                2607
_reflns_number_total             3098
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo200014v_si_002.cif
_cod_data_source_block           a
_cod_database_code               4026232