Electrophilic Transannular Cyclization of Octadehydrodibenzo[12]annulene Reexamined: Indication of the Formation of Both anti- and syn-Indenofluorenes
Takashi Takeda; Koji Inukai; Kazukuni Tahara; Yoshito Tobe; Journal of Organic Chemistry 76 (2011) 9116–9121; doi:10.1021/jo2014593

data_4026685
_publ_section_title
;
 Electrophilic Transannular Cyclization of Octadehydrodibenzo[12]annulene
 Reexamined: Indication of the Formation of Both anti- and
 syn-Indenofluorenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9116
_journal_page_last               9121
_journal_paper_doi               10.1021/jo2014593
_journal_volume                  76
_journal_year                    2011
_chemical_compound_source        'synthesis as described'
_chemical_formula_moiety         'C18 H20 Br3 O2'
_chemical_formula_sum            'C18 H20 Br3 O2'
_chemical_formula_weight         508.07
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90
_cell_angle_beta                 91.606(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.0389(12)
_cell_length_b                   11.3271(16)
_cell_length_c                   16.240(2)
_cell_measurement_reflns_used    18369
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      54.95
_cell_measurement_theta_min      6.02
_cell_measurement_wavelength     0.71073
_cell_volume                     1846.0(4)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0997
_diffrn_reflns_av_unetI/netI     0.0695
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17900
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    6.562
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.828
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.997
_refine_diff_density_min         -1.136
_refine_diff_density_rms         0.172
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         4208
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.075
_refine_ls_R_factor_all          0.054
_refine_ls_R_factor_gt           0.0408
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0403P)^2^+2.1812P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1053
_reflns_number_gt                3515
_reflns_number_total             4208
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo2014593_si_002.cif
_cod_data_source_block           C18H20Br3O2
_cod_original_sg_symbol_H-M      'P 21/a'
_cod_database_code               4026685