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_4026431
_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, C H4 O'
_chemical_formula_sum            'C29 H26 N2 O2'
_chemical_formula_weight         434.52
_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                 94.271(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.4719(7)
_cell_length_b                   11.9181(9)
_cell_length_c                   15.2769(10)
_cell_measurement_reflns_used    7264
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.95
_cell_measurement_theta_min      2.10
_cell_volume                     2264.5(3)
_computing_cell_refinement       'CELL in IPDS-I (Stoe & Cie, 2000)'
_computing_data_collection       'EXPOSE in IPDS-I (Stoe & Cie, 2000)'
_computing_data_reduction        'INTEGRATE in IPDS-I (Stoe & Cie, 2000)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_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 0.994
_diffrn_measured_fraction_theta_max 0.987
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0823
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            16666
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.01
_diffrn_reflns_theta_min         2.04
_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    1.275
_exptl_crystal_description       rod
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.0083(6)
_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   0.771
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     301
_refine_ls_number_reflns         4405
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.771
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0336
_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^)+(0.0368P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0674
_refine_ls_wR_factor_ref         0.0748
_reflns_number_gt                2316
_reflns_number_total             4405
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo200788k_si_001_1.cif
_cod_data_source_block           trans-4a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4026431