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_4023326
_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            'C12 H20 I N O3'
_chemical_formula_weight         353.19
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 105.701(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.8678(14)
_cell_length_b                   11.6482(13)
_cell_length_c                   12.8796(18)
_cell_measurement_temperature    143(1)
_cell_volume                     1425.2(3)
_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 0.953
_diffrn_measured_fraction_theta_max 0.953
_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  0.0150
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8968
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.77
_exptl_absorpt_coefficient_mu    2.245
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8072
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_density_diffrn    1.646
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.624
_refine_diff_density_min         -1.316
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         3113
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.0257
_refine_ls_R_factor_gt           0.0241
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0304P)^2^+0.9256P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0580
_refine_ls_wR_factor_ref         0.0592
_reflns_number_gt                2924
_reflns_number_total             3113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702153q-File003.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'P 21/n     '
_cod_database_code               4023326