Asymmetric synthesis of gem-diaryl substituted cyclic sulfamidates and sulfamides by rhodium-catalyzed arylation of cyclic ketimines
Takahiro Nishimura; Yusuke Ebe; Hiroto Fujimoto; Tamio Hayashi; Chem.Commun. 49 (2013) 5504–; doi:10.1039/c3cc42071j

data_7109375
_publ_section_title
;
 Asymmetric synthesis of gem-diaryl substituted cyclic sulfamidates and
 sulfamides by rhodium-catalyzed arylation of cyclic ketimines
;
_journal_name_full               Chem.Commun.
_journal_page_first              5504
_journal_paper_doi               10.1039/c3cc42071j
_journal_volume                  49
_journal_year                    2013
_chemical_absolute_configuration ad
_chemical_formula_sum            'C14 H12 Cl N O3 S'
_chemical_formula_weight         309.76
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      4
_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                 114.5778(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4413(2)
_cell_length_b                   15.6524(3)
_cell_length_c                   9.8374(2)
_cell_measurement_reflns_used    7203
_cell_measurement_temperature    93(2)
_cell_measurement_theta_max      68.24
_cell_measurement_theta_min      4.94
_cell_volume                     1322.05(5)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      93(2)
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.959
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       \w
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.1017
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7504
_diffrn_reflns_theta_full        63.00
_diffrn_reflns_theta_max         63.00
_diffrn_reflns_theta_min         4.94
_exptl_absorpt_coefficient_mu    4.103
_exptl_absorpt_correction_T_max  0.8211
_exptl_absorpt_correction_T_min  0.4941
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;Higashi, T. (1995).
Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.403
_refine_diff_density_min         -0.433
_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   -0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     361
_refine_ls_number_reflns         3777
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0505
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0650P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1243
_refine_ls_wR_factor_ref         0.1379
_reflns_number_gt                3242
_reflns_number_total             3777
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc42071j.txt
_cod_data_source_block           1225yu
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7109375