Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles and 2-Arylbenzoxazoles via C-H Functionalization/C-N/C-O Bond Formation
Murali Mohan Guru; Md Ashif Ali; Tharmalingam Punniyamurthy; Journal of Organic Chemistry 76 (2011) 5295–5308; doi:10.1021/jo2005632

data_4026412
_publ_section_title
;
 Copper-Mediated Synthesis of Substituted 2-Aryl-N-benzylbenzimidazoles
 and 2-Arylbenzoxazoles via C-H Functionalization/C-N/C-O Bond Formation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5295
_journal_page_last               5308
_journal_paper_doi               10.1021/jo2005632
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C20 H15 Cl N2'
_chemical_formula_sum            'C20 H15 Cl N2'
_chemical_formula_weight         318.79
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_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                 91.041(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.2920(3)
_cell_length_b                   17.3537(9)
_cell_length_c                   14.9263(7)
_cell_measurement_reflns_used    9898
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      28.430
_cell_measurement_theta_min      1.83
_cell_volume                     1629.53(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      298(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0715
_diffrn_reflns_av_sigmaI/netI    0.0334
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24406
_diffrn_reflns_theta_full        28.43
_diffrn_reflns_theta_max         28.43
_diffrn_reflns_theta_min         1.80
_exptl_absorpt_coefficient_mu    0.235
_exptl_absorpt_correction_T_max  0.941
_exptl_absorpt_correction_T_min  0.923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 1997)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_description       square
_exptl_crystal_F_000             664.0
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_matrix_type           full
_refine_ls_number_parameters     209
_refine_ls_number_reflns         4009
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0589
_refine_ls_R_factor_gt           0.0413
_refine_ls_shift/su_max          0.015
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.0338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1218
_refine_ls_wR_factor_ref         0.1309
_reflns_number_gt                2826
_reflns_number_total             4009
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo2005632_si_001.cif
_cod_data_source_block           mg-1
_cod_original_sg_symbol_H-M      'P 1 21/c 1 '
_cod_database_code               4026412