Accessing N-heteroarylated indoles and benzimidazoles from 2-alkynyl cyclohexadienimines and cyclohexadienones through metal-catalyzed tandem reactions
Min Yang; Jie Tang; Renhua Fan; Chem.Commun. 48 (2012) 11775–; doi:10.1039/c2cc36113b

data_7108631
_publ_section_title
;
 Accessing N-heteroarylated indoles and benzimidazoles from 2-alkynyl
 cyclohexadienimines and cyclohexadienones through metal-catalyzed tandem
 reactions
;
_journal_name_full               Chem.Commun.
_journal_page_first              11775
_journal_paper_doi               10.1039/c2cc36113b
_journal_volume                  48
_journal_year                    2012
_chemical_formula_sum            'C39 H35 N2 O2 S'
_chemical_formula_weight         595.75
_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                 99.619(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   17.111(13)
_cell_length_b                   9.641(7)
_cell_length_c                   20.781(16)
_cell_measurement_reflns_used    1012
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.552
_cell_measurement_theta_min      2.860
_cell_volume                     3380(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_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      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0609
_diffrn_reflns_av_sigmaI/netI    0.0574
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14014
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.9935
_exptl_absorpt_correction_T_min  0.9806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.081
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     399
_refine_ls_number_reflns         6242
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1036P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1509
_refine_ls_wR_factor_ref         0.1704
_reflns_number_gt                4212
_reflns_number_total             6242
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36113b.txt
_cod_data_source_block           a20221b
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               7108631