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_7108632
_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            'C29 H21 N O'
_chemical_formula_weight         399.47
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                110.153(9)
_cell_angle_beta                 113.335(9)
_cell_angle_gamma                91.558(9)
_cell_formula_units_Z            2
_cell_length_a                   9.856(7)
_cell_length_b                   10.337(7)
_cell_length_c                   12.127(8)
_cell_measurement_reflns_used    718
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.533
_cell_measurement_theta_min      2.285
_cell_volume                     1045.6(12)
_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 0.975
_diffrn_measured_fraction_theta_max 0.975
_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  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0519
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4553
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         1.98
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9887
_exptl_absorpt_correction_T_min  0.9812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.163
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0572
_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^)+(0.0669P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1485
_reflns_number_gt                2276
_reflns_number_total             3790
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2cc36113b.txt
_cod_data_source_block           a11227a
_cod_original_cell_volume        1045.7(12)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               7108632