An Aza Cyclopropylcarbinyl-Homoallyl Radical Rearrangement-Radical Cyclization Cascade. Synthesis of Dibenzoimidazoazepine and Oxazepine Derivatives
Alexander F. Khlebnikov; Mikhail S. Novikov; Petr P. Petrovskii; Helen Stoeckli-Evans; Journal of Organic Chemistry 76 (2011) 5384–5391; doi:10.1021/jo200788k

data_4026433
_publ_section_title
;
 An Aza Cyclopropylcarbinyl-Homoallyl Radical Rearrangement-Radical
 Cyclization Cascade. Synthesis of Dibenzoimidazoazepine and Oxazepine
 Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5384
_journal_page_last               5391
_journal_paper_doi               10.1021/jo200788k
_journal_volume                  76
_journal_year                    2011
_chemical_formula_moiety         'C28 H18 Br2 N2 O'
_chemical_formula_sum            'C28 H18 Br2 N2 O'
_chemical_formula_weight         558.26
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 90.052(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   13.3684(6)
_cell_length_b                   15.8505(8)
_cell_length_c                   32.3270(19)
_cell_measurement_reflns_used    18531
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.03
_cell_measurement_theta_min      1.80
_cell_volume                     6850.0(6)
_computing_cell_refinement       'X-Area V1.52'
_computing_data_collection       'X-Area V1.52 (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32 V1.48 (Stoe & Cie, 2009)'
_computing_molecular_graphics    'PLATON  (Spek, 2009)'
_computing_publication_material  'SHELXL-97 & PLATON'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'STOE IPDS-2'
_diffrn_measurement_method       '\f + \w 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  0.2094
_diffrn_reflns_av_sigmaI/netI    0.1596
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            56776
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.70
_diffrn_reflns_theta_min         1.26
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.575
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6065
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'MULscanABS in PLATON (Spek, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       lath
_exptl_crystal_F_000             3336
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.217
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.722
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.133
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     892
_refine_ls_number_reflns         12892
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.1701
_refine_ls_R_factor_gt           0.0804
_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^)+(0.0769P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1647
_refine_ls_wR_factor_ref         0.2016
_reflns_number_gt                5934
_reflns_number_total             12892
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo200788k_si_001_3.cif
_cod_data_source_block           6a
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026433