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_7115587
_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_absolute_configuration ad
_chemical_formula_sum            'C18 H18 F2 N O S'
_chemical_formula_weight         335.40
_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                   8.7675(12)
_cell_length_b                   10.5238(14)
_cell_length_c                   18.173(2)
_cell_measurement_reflns_used    1795
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42.051
_cell_measurement_theta_min      4.473
_cell_volume                     1676.8(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 0.999
_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  0.1205
_diffrn_reflns_av_sigmaI/netI    0.1110
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10158
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.24
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7258
_exptl_absorpt_correction_type   empirical
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.421
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.127
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.18(10)
_refine_ls_extinction_coef       0.0218(19)
_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   0.859
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         3793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.859
_refine_ls_R_factor_all          0.0858
_refine_ls_R_factor_gt           0.0545
_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^)+(0.0342P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1057
_refine_ls_wR_factor_ref         0.1171
_reflns_number_gt                2322
_reflns_number_total             3793
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc05042h2.cif
_cod_data_source_block           cd27130
_cod_original_sg_symbol_H-M      P2(1)2(1)2(1)
_cod_database_code               7115587