Iodine mediated intramolecular C2-amidative cyclization of indoles: a facile access to indole fused tetracycles.
Badigenchala, Sindhura; Rajeshkumar, Venkatachalam; Sekar, Govindasamy; Organic & biomolecular chemistry 14 (2016) 2297–2305; doi:10.1039/c5ob02449h

data_7155011
_publ_section_title
;
 Iodine mediated intramolecular C2-amidative cyclization of indoles: a
 facile access to indole fused tetracycles.
;
_journal_issue                   7
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              2297
_journal_page_last               2305
_journal_paper_doi               10.1039/c5ob02449h
_journal_volume                  14
_journal_year                    2016
_chemical_formula_moiety         'C34 H27 N3 O5 S2, C H Cl3 '
_chemical_formula_sum            'C35 H28 Cl3 N3 O5 S2'
_chemical_formula_weight         741.07
_chemical_name_systematic        Benzimidazoindoloindolol
_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
_audit_block_doi                 10.5517/cc1jp3x7
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-08-25 deposited with the CCDC.
2016-01-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.2453(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1831(2)
_cell_length_b                   17.6304(4)
_cell_length_c                   18.6382(5)
_cell_measurement_reflns_used    6996
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.35
_cell_measurement_theta_min      2.31
_cell_volume                     3343.59(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_av_unetI/netI     0.0260
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            26328
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.590
_exptl_absorpt_coefficient_mu    0.447
_exptl_absorpt_correction_T_max  0.896
_exptl_absorpt_correction_T_min  0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             1528
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CDCl3'
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.250
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         5880
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0715
_refine_ls_R_factor_gt           0.0495
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0725P)^2^+2.8243P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1514
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4265
_reflns_number_total             5880
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob02449h5.cif
_cod_data_source_block           39
_cod_database_code               7155011
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.859
_shelx_estimated_absorpt_t_max   0.896
_shelx_res_checksum              77479
_shelx_hkl_checksum              36284