Synthesis of cyclohepta[b]indoles by (4+3) cycloaddition of 2-vinylindoles or 4H-furo[3,2-b]indoles with oxyallyl cations.
Pirovano, Valentina; Brambilla, Elisa; Moretti, Andrea; Rizzato, Silvia; Abbiati, Giorgio; Nava, Donatella; Rossi, Elisabetta; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03117

data_4037892
_publ_section_title
;
 Synthesis of cyclohepta[b]indoles by (4+3) cycloaddition of
 2-vinylindoles or 4H-furo[3,2-b]indoles with oxyallyl cations.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03117
_journal_year                    2020
_chemical_formula_moiety         'C18 H17 N O4'
_chemical_formula_sum            'C18 H17 N O4'
_chemical_formula_weight         311.33
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      15
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 95.236(8)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.549(8)
_cell_length_b                   11.015(6)
_cell_length_c                   17.360(9)
_cell_measurement_reflns_used    9693
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      31.3
_cell_measurement_theta_min      2.3
_cell_measurement_wavelength     0.71073
_cell_volume                     2961(3)
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution
'SIR 2014: C. Giacovazzo et all., J. Appl. Cryst.(2015) 48, 306'
_diffrn_ambient_temperature      296(2)
_diffrn_detector                 CCD_plate
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.927
_diffrn_measurement_device       'Bruker apex II ccd diffractometer'
_diffrn_measurement_method       omega-scan
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.927
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21326
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_theta_full        25.2
_diffrn_reflns_theta_max         31.6
_diffrn_reflns_theta_min         2.3
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7462
_exptl_absorpt_correction_T_min  0.6602
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Sadabs 2.01 (Bruker AXS, 1999)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.3969
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.42
_exptl_crystal_size_min          0.26
_refine_diff_density_max         0.297
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       0.0069(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     260
_refine_ls_number_reflns         4584
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0599P)^2^+2.0043P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1252
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0
_reflns_number_gt                3512
_reflns_number_total             4584
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03117_si_001.cif
_cod_data_source_block           6a
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4037892