Radical Migration-Addition of N-tert-Butanesulfinyl Imines with Organozinc Reagents
Wei Huang; Jian-Liang Ye; Wei Zheng; Han-Qing Dong; Bang-Guo Wei; Journal of Organic Chemistry 78 (2013) 11229–11237; doi:10.1021/jo401640c

data_4028743
_publ_section_title
;
 Radical Migration-Addition of N-tert-Butanesulfinyl Imines with
 Organozinc Reagents
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              11229
_journal_page_last               11237
_journal_paper_doi               10.1021/jo401640c
_journal_volume                  78
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C15 H22 Br N O3 S'
_chemical_formula_weight         376.31
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_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                 94.020(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.2067(14)
_cell_length_b                   7.1568(9)
_cell_length_c                   22.836(3)
_cell_measurement_reflns_used    2237
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38.988
_cell_measurement_theta_min      5.282
_cell_volume                     1827.0(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 0.989
_diffrn_measured_fraction_theta_max 0.989
_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  0.0778
_diffrn_reflns_av_sigmaI/netI    0.1279
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            10843
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.79
_exptl_absorpt_coefficient_mu    2.372
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.4343
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             776
_exptl_crystal_size_max          0.436
_exptl_crystal_size_mid          0.369
_exptl_crystal_size_min          0.147
_refine_diff_density_max         0.473
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.081
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.005(12)
_refine_ls_extinction_coef       0.0207(14)
_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   0.827
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         7378
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.827
_refine_ls_R_factor_all          0.1109
_refine_ls_R_factor_gt           0.0637
_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^)+(0.0711P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1373
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                3653
_reflns_number_total             7378
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo401640c_si_001.cif
_cod_data_source_block           cd28166
_cod_original_cell_volume        1827.1(4)
_cod_database_code               4028743