Formation of Benzimidazoisoquinolinium and Benzimidazoisoindolinum Cyclic Systems by the Reaction of 2-(2-Alkynylphenyl)benzimidazoles with Iodine and Iodine-Iodine Interaction Including Halogen Bonding in Their Crystal Structures.
Matsumoto, Shoji; Kikuchi, Shu; Norita, Naoto; Masu, Hyuma; Akazome, Motohiro; The Journal of organic chemistry 81 (2016) 5322–5329; doi:10.1021/acs.joc.6b00607

data_4032014
_publ_section_title
;
 Formation of Benzimidazoisoquinolinium and Benzimidazoisoindolinum Cyclic
 Systems by the Reaction of 2-(2-Alkynylphenyl)benzimidazoles with Iodine
 and Iodine-Iodine Interaction Including Halogen Bonding in Their Crystal
 Structures.
;
_journal_issue                   13
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              5322
_journal_page_last               5329
_journal_paper_doi               10.1021/acs.joc.6b00607
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C24 H20 I4 N2 O'
_chemical_formula_weight         860.02
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 100.361(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5581(9)
_cell_length_b                   14.7892(9)
_cell_length_c                   14.3839(11)
_cell_measurement_reflns_used    9912
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      68.2894
_cell_measurement_theta_min      2.9880
_cell_volume                     2627.9(3)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0491
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27716
_diffrn_reflns_theta_full        68.492
_diffrn_reflns_theta_max         68.492
_diffrn_reflns_theta_min         4.307
_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_exptl_absorpt_coefficient_mu    37.387
_exptl_absorpt_correction_T_max  0.21
_exptl_absorpt_correction_T_min  0.12
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    2.174
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1592
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.060
_refine_diff_density_max         1.894
_refine_diff_density_min         -1.534
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4630
_refine_ls_number_restraints     25
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0971
_refine_ls_R_factor_gt           0.0842
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1650P)^2^+12.4549P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2457
_refine_ls_wR_factor_ref         0.2638
_reflns_number_gt                3688
_reflns_number_total             4630
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b00607_si_006.cif
_cod_data_source_block           3e_I3
_cod_database_code               4032014