Radical Cyclizations of Cyclic Ene Sulfonamides Occur with β-Elimination of Sulfonyl Radicals to Form Polycyclic Imines
Hanmo Zhang; E. Ben Hay; Steven J. Geib; Dennis P. Curran; Journal of the American Chemical Society 135 (2013) 16610–16617; doi:10.1021/ja408387d

data_4121085
_publ_section_title
;
 Radical Cyclizations of Cyclic Ene Sulfonamides Occur with \b-Elimination
 of Sulfonyl Radicals to Form Polycyclic Imines
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16610
_journal_page_last               16617
_journal_paper_doi               10.1021/ja408387d
_journal_volume                  135
_journal_year                    2013
_chemical_formula_sum            'C20 H20 N2 O'
_chemical_formula_weight         304.38
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_symmetry_space_group_name_H-M   'C 1 2/c 1'
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_atom_sites_solution_secondary   difmap
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_cell_angle_beta                 102.83(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   32.01(3)
_cell_length_b                   5.880(5)
_cell_length_c                   17.369(14)
_cell_measurement_reflns_used    2470
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      26.76
_cell_measurement_theta_min      2.405
_cell_volume                     3188(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      203(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_diffrn_measurement_method       '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  0.0836
_diffrn_reflns_av_sigmaI/netI    0.0714
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12892
_diffrn_reflns_theta_full        28.17
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_min         2.41
_exptl_absorpt_coefficient_mu    0.079
_exptl_absorpt_correction_T_max  0.9859
_exptl_absorpt_correction_T_min  0.9783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_density_meas      0
_exptl_crystal_description       block
_exptl_crystal_F_000             1296
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3829
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0621
_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^)+(0.0780P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1471
_refine_ls_wR_factor_ref         0.1696
_reflns_number_gt                2215
_reflns_number_total             3829
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja408387d_si_002.cif
_cod_data_source_block           hz1011
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4121085