Stereoselective Formation of Glycosyl Sulfoxides and Their Subsequent Equilibration: Ring Inversion of an α-Xylopyranosyl Sulfoxide Dependent on the Configuration at Sulfur
David Crich; Jan Mataka; Lev N. Zakharov; Arnold L. Rheingold; Donald J. Wink; Journal of the American Chemical Society 124 (2002) 6028–6036; doi:10.1021/ja0122694

data_4114816
_publ_contact_author_address
; Department of Chemistry (m/c 111)
   University of Illinois at Chicago
   845 W. Taylor Street
   Chicago, Illinois 60607
   USA
;
_publ_contact_author_email       dwink@uic.edu
_publ_contact_author_fax         (312)9960431
_publ_contact_author_name        'Dr. Donald J. Wink'
_publ_contact_author_phone       (312)4137383
_publ_section_title
;
 Stereoselective Formation of Glycosyl Sulfoxides and Their Subsequent
 Equilibration: Ring Inversion of an \a-Xylopyranosyl Sulfoxide Dependent
 on the Configuration at Sulfur
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              6028
_journal_page_last               6036
_journal_paper_doi               10.1021/ja0122694
_journal_volume                  124
_journal_year                    2002
_chemical_formula_sum            'C29 H26 O8 S'
_chemical_formula_weight         534.56
_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                   7.452(4)
_cell_length_b                   10.874(5)
_cell_length_c                   31.285(13)
_cell_measurement_temperature    213(2)
_cell_volume                     2535(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_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      213(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_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  0.0896
_diffrn_reflns_av_sigmaI/netI    0.0997
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            11738
_diffrn_reflns_theta_full        23.33
_diffrn_reflns_theta_max         23.33
_diffrn_reflns_theta_min         1.30
_exptl_absorpt_coefficient_mu    0.180
_exptl_absorpt_correction_T_max  0.9479
_exptl_absorpt_correction_T_min  0.9314
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      0
_exptl_crystal_description       chunk
_exptl_crystal_F_000             1120
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.313
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     343
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.313
_refine_ls_R_factor_all          0.1168
_refine_ls_R_factor_gt           0.0961
_refine_ls_shift/su_max          0.031
_refine_ls_shift/su_mean         0.006
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s2(Fo2)+(0.0800P)2+0.0000P] where P=(Fo2+2Fc2)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2025
_refine_ls_wR_factor_ref         0.2106
_reflns_number_gt                2976
_reflns_number_total             3644
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja0122694_2.cif
_cod_data_source_block           Compound20
_cod_database_code               4114816