Stereoselective [3+2] cycloaddition of N-tert-butanesulfinyl imines to arynes facilitated by a removable PhSO2CF2 group: synthesis and transformation of cyclic sulfoximines
Wenchao Ye; Laijun Zhang; Chuanfa Ni; Jian Rong; Jinbo Hu; Chem.Commun. 50 (2014) 10596–; doi:10.1039/C4cc05042H

data_7115592
_publ_section_title
;
 Stereoselective [3+2] cycloaddition of N-tert-butanesulfinyl imines to
 arynes facilitated by a removable PhSO2CF2 group: synthesis and
 transformation of cyclic sulfoximines
;
_journal_name_full               Chem.Commun.
_journal_page_first              10596
_journal_paper_doi               10.1039/C4cc05042H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C21 H16 Br N O3 S'
_chemical_formula_sum            'C21 H16 Br N O3 S'
_chemical_formula_weight         442.32
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 92.78(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.876(2)
_cell_length_b                   11.292(2)
_cell_length_c                   16.818(3)
_cell_measurement_reflns_used    6898
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      66.94
_cell_measurement_theta_min      4.72
_cell_volume                     1873.3(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.947
_diffrn_measured_fraction_theta_max 0.947
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_sigmaI/netI    0.0190
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12287
_diffrn_reflns_theta_full        67.33
_diffrn_reflns_theta_max         67.33
_diffrn_reflns_theta_min         4.72
_exptl_absorpt_coefficient_mu    4.218
_exptl_absorpt_correction_T_max  0.7859
_exptl_absorpt_correction_T_min  0.2472
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.568
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       column
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.634
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       0.00028(11)
_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   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         3191
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0423P)^2^+1.9087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0985
_refine_ls_wR_factor_ref         0.1002
_reflns_number_gt                2980
_reflns_number_total             3191
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05042h2.cif
_cod_data_source_block           040
_cod_original_cell_volume        1873.4(7)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7115592