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_4026432
_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 H22 N2 O'
_chemical_formula_sum            'C28 H22 N2 O'
_chemical_formula_weight         402.48
_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                 98.820(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.6754(6)
_cell_length_b                   18.9368(12)
_cell_length_c                   12.4873(9)
_cell_measurement_reflns_used    8000
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      26.00
_cell_measurement_theta_min      1.90
_cell_volume                     2027.2(2)
_computing_cell_refinement       'CELL (Stoe & Cie, 2000)'
_computing_data_collection       'EXPOSE (Stoe & Cie, 2000)'
_computing_data_reduction        'INTEGRATE (Stoe & Cie, 2000)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'STOE IPDS'
_diffrn_measurement_method       'phi rotation'
_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  0.0388
_diffrn_reflns_av_sigmaI/netI    0.0581
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15979
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         2.15
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       rod
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.153
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0101(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.818
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.818
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0298
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0349P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0598
_refine_ls_wR_factor_ref         0.0650
_reflns_number_gt                2355
_reflns_number_total             3881
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo200788k_si_001_2.cif
_cod_data_source_block           trans-5a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026432