Catalytic asymmetric oxidation of cyclic dithioacetals: highly diastereo- and enantioselective synthesis of the S-oxides by a chiral aluminum(salalen) complex
Fujisaki, Junichi; Matsumoto, Kenji; Matsumoto, Kazuhiro; Katsuki, Tsutomu; Journal of the American Chemical Society 133 (2011) 56–61; doi:10.1021/ja106877x

data_4121889
_publ_section_title
;
 Catalytic asymmetric oxidation of cyclic dithioacetals: highly diastereo-
 and enantioselective synthesis of the S-oxides by a chiral
 aluminum(salalen) complex
;
_journal_coden_ASTM              JACSAT
_journal_issue                   1
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              56
_journal_page_last               61
_journal_paper_doi               10.1021/ja106877x
_journal_volume                  133
_journal_year                    2011
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H12 O S2'
_chemical_formula_sum            'C12 H12 O S2'
_chemical_formula_weight         236.33
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.0880(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.2896(14)
_cell_length_b                   5.7582(6)
_cell_length_c                   15.3496(16)
_cell_measurement_reflns_used    9908
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.42
_cell_measurement_theta_min      2.38
_cell_volume                     1128.6(2)
_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      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating-anode X-ray tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0122
_diffrn_reflns_av_sigmaI/netI    0.0136
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12914
_diffrn_reflns_theta_full        27.43
_diffrn_reflns_theta_max         27.43
_diffrn_reflns_theta_min         1.38
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.9171
_exptl_absorpt_correction_T_min  0.8099
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.130
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         5109
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0186
_refine_ls_R_factor_gt           0.0184
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0323P)^2^+0.1303P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0499
_refine_ls_wR_factor_ref         0.0501
_reflns_number_gt                5055
_reflns_number_total             5109
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4101612
_cod_data_source_file            ja106877x_si_002.cif
_cod_data_source_block           phenylethynyl_SSO
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)
_cod_database_code               4121889