Synthesis of Benzocyclohepta[b]indoles by Lewis Acid Catalyzed Annulation of Two 3-(1H-Isochromen-1-yl)-1H-indoles.
Xie, Ye-Xiang; Tang, Ri-Yuan; Song, Ren-Jie; Xiang, Jian-Nan; Li, Jin-Heng; The Journal of organic chemistry 79 (2014) 686–691; doi:10.1021/jo4024667

data_4028984
_publ_section_title
;
 Synthesis of Benzocyclohepta[b]indoles by Lewis Acid Catalyzed Annulation
 of Two 3-(1H-Isochromen-1-yl)-1H-indoles.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              686
_journal_page_last               691
_journal_paper_doi               10.1021/jo4024667
_journal_volume                  79
_journal_year                    2014
_chemical_formula_sum            'C46 H34 N2 O2'
_chemical_formula_weight         646.75
_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                 108.0860(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.1459(11)
_cell_length_b                   11.8659(8)
_cell_length_c                   18.6686(12)
_cell_measurement_reflns_used    5194
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      50.239
_cell_measurement_theta_min      4.340
_cell_volume                     3399.9(4)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0463
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            18109
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         26.00
_diffrn_reflns_theta_min         2.01
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62054
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.426
_exptl_crystal_size_mid          0.357
_exptl_crystal_size_min          0.223
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.925
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     459
_refine_ls_number_reflns         6683
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.925
_refine_ls_R_factor_all          0.0639
_refine_ls_R_factor_gt           0.0432
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1124
_reflns_number_gt                4606
_reflns_number_total             6683
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo4024667_si_001.cif
_cod_data_source_block           cd201465
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4028984