Efficient Regio- and Stereoselective Formation of Azocan-2-ones via 8-EndoCyclization of α-Carbamoyl Radicals
Xinqiang Fang; Kun Liu; Chaozhong Li; Journal of the American Chemical Society 132 (2010) 2274–2283; doi:10.1021/ja9082649

data_4101905
_publ_section_title
;
 Efficient Regio- and Stereoselective Formation of Azocan-2-ones via
 8-EndoCyclization of \a-Carbamoyl Radicals
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2274
_journal_page_last               2283
_journal_paper_doi               10.1021/ja9082649
_journal_volume                  132
_journal_year                    2010
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H18 I N O3'
_chemical_formula_weight         387.20
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.9889(10)
_cell_length_b                   8.9128(12)
_cell_length_c                   22.255(3)
_cell_measurement_reflns_used    2928
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.393
_cell_measurement_theta_min      4.923
_cell_volume                     1584.6(4)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.0556
_diffrn_reflns_av_sigmaI/netI    0.0472
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            8212
_diffrn_reflns_theta_full        25.49
_diffrn_reflns_theta_max         25.49
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    2.027
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5522
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.422
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.186
_refine_diff_density_max         1.716
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.105
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(17)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2949
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0578
_refine_ls_shift/su_max          0.049
_refine_ls_shift/su_mean         0.003
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0944P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1488
_refine_ls_wR_factor_ref         0.1574
_reflns_number_gt                2297
_reflns_number_total             2949
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9082649_si_004.cif
_cod_data_source_block           cd29114
_cod_database_code               4101905