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_4035272
_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 H27 N O3'
_chemical_formula_sum            'C29 H27 N O3'
_chemical_formula_weight         437.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            8
_cell_length_a                   20.4350(4)
_cell_length_b                   9.87597(18)
_cell_length_c                   22.7727(4)
_cell_measurement_reflns_used    22879
_cell_measurement_temperature    93
_cell_measurement_theta_max      68.13
_cell_measurement_theta_min      3.88
_cell_volume                     4595.88(15)
_computing_cell_refinement       'RAPID AUTO'
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_data_reduction        'RAPID AUTO'
_computing_molecular_graphics    'CrystalStructure 4.2.2'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      93
_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  0.1385
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            46168
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_theta_full        68.200
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_min         3.882
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.968
_exptl_absorpt_correction_T_min  0.466
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1856.00
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.31
_refine_diff_density_min         -0.58
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1764
_refine_ls_R_factor_gt           0.1193
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2710
_refine_ls_wR_factor_ref         0.3640
_reflns_number_gt                2160
_reflns_number_total             4185
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo8b01407_si_003.cif
_cod_data_source_block           170908takeda01
_cod_original_cell_volume        4595.89(14)
_cod_database_code               4035272