Neighboring Group Participation in the Additions of Iodonium and Bromonium Ions to N-Alkoxycarbonyl-2-azabicyclo[2.2.n]alk-5-enes (n = 1,2)
Grant R. Krow; Deepa Gandla; Weiwei Guo; Ryan A. Centafont; Guoliang Lin; Charles DeBrosse; Philip E. Sonnet; Ross, III, Charles W.; Harri G. Ramjit; Patrick J. Carroll; Kevin C. Cannon; Journal of Organic Chemistry 73 (2008) 2114–2121; doi:10.1021/jo702153q

data_4023325
_publ_section_title
;
 Neighboring Group Participation in the Additions of Iodonium and
 Bromonium Ions to N-Alkoxycarbonyl-2-azabicyclo[2.2.n]alk-5-enes
 (n = 1,2)
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2114
_journal_page_last               2121
_journal_paper_doi               10.1021/jo702153q
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C8 H16 Br N O2'
_chemical_formula_weight         238.13
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.3026(7)
_cell_length_b                   8.0682(4)
_cell_length_c                   21.4599(13)
_cell_measurement_temperature    143(1)
_cell_volume                     1957.0(2)
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR97 (Altomare, 1999)'
_diffrn_ambient_temperature      143(1)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Rigaku Mercury'
_diffrn_measurement_method       'phi and omega rotations'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0174
_diffrn_reflns_av_sigmaI/netI    0.0242
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            9540
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.62
_exptl_absorpt_coefficient_mu    4.164
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7030
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.805
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     111
_refine_ls_number_reflns         2235
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.982
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0245
_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^)+(0.0376P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0606
_refine_ls_wR_factor_ref         0.0629
_reflns_number_gt                1831
_reflns_number_total             2235
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702153q-File002.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P b c a '
_cod_database_code               4023325