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_4101902
_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_formula_sum            'C10.5 H16 Cl I N O3'
_chemical_formula_weight         366.59
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           56
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ab 2ac'
_symmetry_space_group_name_H-M   'P c c n'
_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            8
_cell_length_a                   13.863(2)
_cell_length_b                   30.022(4)
_cell_length_c                   6.2454(9)
_cell_measurement_reflns_used    1221
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      40.903
_cell_measurement_theta_min      5.428
_cell_volume                     2599.3(6)
_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 0.999
_diffrn_measured_fraction_theta_max 0.999
_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  0.1405
_diffrn_reflns_av_sigmaI/netI    0.1302
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            14035
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    2.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76333
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.874
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1440
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.642
_refine_diff_density_min         -1.015
_refine_diff_density_rms         0.136
_refine_ls_extinction_coef       0.0010(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   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2824
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.934
_refine_ls_R_factor_all          0.1607
_refine_ls_R_factor_gt           0.0772
_refine_ls_shift/su_max          0.050
_refine_ls_shift/su_mean         0.019
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1340P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2335
_refine_ls_wR_factor_ref         0.2632
_reflns_number_gt                1248
_reflns_number_total             2824
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja9082649_si_001.cif
_cod_data_source_block           cd27556
_cod_original_cell_volume        2599.3(7)
_cod_original_formula_sum        'C10.50 H16 Cl I N O3'
_cod_database_code               4101902