CuI/I2-Promoted Electrophilic Tandem Cyclization of 2-Ethynylbenzaldehydes with ortho-Benzenediamines: Synthesis of Iodoisoquinoline-Fused Benzimidazoles
Huang-Che Ouyang; Ri-Yuan Tang; Ping Zhong; Xing-Guo Zhang; Jin-Heng Li; Journal of Organic Chemistry 76 (2011) 223–228; doi:10.1021/jo102060j

data_4025965
_publ_section_title
;
 CuI/I2-Promoted Electrophilic Tandem Cyclization of
 2-Ethynylbenzaldehydes with ortho-Benzenediamines: Synthesis of
 Iodoisoquinoline-Fused Benzimidazoles
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              223
_journal_page_last               228
_journal_paper_doi               10.1021/jo102060j
_journal_volume                  76
_journal_year                    2011
_chemical_formula_sum            'C21 H13 I N2'
_chemical_formula_weight         420.23
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 102.295(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0443(8)
_cell_length_b                   16.3435(15)
_cell_length_c                   11.2531(10)
_cell_measurement_reflns_used    4258
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      55.429
_cell_measurement_theta_min      4.985
_cell_volume                     1625.2(3)
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_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  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9496
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         2.23
_exptl_absorpt_coefficient_mu    1.974
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5725
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.717
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.307
_exptl_crystal_size_mid          0.285
_exptl_crystal_size_min          0.190
_refine_diff_density_max         0.726
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.980
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3516
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.980
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0325
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0785
_refine_ls_wR_factor_ref         0.0813
_reflns_number_gt                2954
_reflns_number_total             3516
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo102060j_si_001.cif
_cod_data_source_block           cd201167
_cod_database_code               4025965