Cyclohepta[ b]indole Synthesis through [5 + 2] Cycloaddition: Bifunctional Indium(III)-Catalyzed Stereoselective Construction of 7-Membered Ring Fused Indoles.
Takeda, Takuya; Harada, Shinji; Okabe, Akito; Nishida, Atsushi; The Journal of organic chemistry 83 (2018) 11541–11551; doi:10.1021/acs.joc.8b01407

data_4035271
_publ_section_title
;
 Cyclohepta[ b]indole Synthesis through [5 + 2] Cycloaddition:
 Bifunctional Indium(III)-Catalyzed Stereoselective Construction of
 7-Membered Ring Fused Indoles.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11541
_journal_page_last               11551
_journal_paper_doi               10.1021/acs.joc.8b01407
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C29 H25 N O2'
_chemical_formula_sum            'C29 H25 N O2'
_chemical_formula_weight         419.52
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 103.7348(12)
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   14.5780(4)
_cell_length_b                   12.8873(3)
_cell_length_c                   23.6203(6)
_cell_measurement_reflns_used    18076
_cell_measurement_temperature    113
_cell_measurement_theta_max      68.17
_cell_measurement_theta_min      3.12
_cell_volume                     4310.68(19)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.5'
_computing_publication_material  'CrystalStructure 4.2.5 (Rigaku, 2017)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_diffrn_ambient_temperature      113
_diffrn_detector_area_resol_mean 10.000
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.1013
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            44830
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.240
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.121
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.633
_exptl_absorpt_correction_T_max  0.881
_exptl_absorpt_correction_T_min  0.636
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1776.00
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.35
_refine_diff_density_min         -0.44
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.924
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     585
_refine_ls_number_reflns         7886
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1786
_refine_ls_R_factor_gt           0.0982
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.1758P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2299
_refine_ls_wR_factor_ref         0.3115
_reflns_number_gt                3181
_reflns_number_total             7886
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b01407_si_004.cif
_cod_data_source_block           171212takeda01
_cod_depositor_comments
;

2020-08-05
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        4310.68(18)
_cod_original_formula_moiety     'C58 H50 N2 O4'
_cod_original_formula_sum        'C58 H50 N2 O4'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     839.04
_cod_database_code               4035271