Stereoselective sulfoxidation of α-mannopyranosyl thioglycosides: the exo-anomeric effect in action
Crich, David; Mataka, Jan; Sun, Sanxing; Wink, Donald J.; Lam, K.-C.; Rheingold, Arnold L.; Chemical Communications  (1998) 2763–; doi:10.1039/a804126a

data_7110353
_publ_section_title
;
 Stereoselective sulfoxidation of \a-mannopyranosyl thioglycosides: the
 exo-anomeric effect in action
;
_journal_issue                   24
_journal_name_full               'Chemical Communications'
_journal_page_first              2763
_journal_paper_doi               10.1039/a804126a
_journal_year                    1998
_chemical_formula_analytical     'C14 H23 O6 S1'
_chemical_formula_moiety         'C14 H23 O6 S1'
_chemical_formula_structural     'C14 H23 O6 S1'
_chemical_formula_sum            'C14 H23 O6 S'
_chemical_formula_weight         319.4
_chemical_melting_point          ?
_chemical_name_common
'  Compound 20: Mannosyl diacetonide ethyl sulfone'
_chemical_name_systematic
; 1-Deoxy-2,3;4,6-diisopropylidene-1-thia-
  1-\a-D-mannopyranoside S-Oxide
;
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00(9)
_cell_angle_beta                 99.73(6)
_cell_angle_gamma                90.00(9)
_cell_formula_units_Z            4
_cell_length_a                   11.282(7)
_cell_length_b                   9.766(10)
_cell_length_c                   15.555(12)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      9.59
_cell_measurement_theta_min      4.51
_cell_volume                     1689(2)
_computing_cell_refinement       'CAD-4 MS-DOS control software'
_computing_data_collection       'CAD-4 MS-DOS control software'
_computing_data_reduction        xtal_DIFDAT_ABSORB_SORTRF_ADDREF
_computing_molecular_graphics    xtal
_computing_publication_material  xtal_BONDLA_CIFIO
_computing_structure_refinement  xtal_CRYLSQ
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_measurement_device       'Enraf-Nonius CAD-4'
_diffrn_measurement_method       \w--2\q
_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  0.0398
_diffrn_reflns_av_sigmaI/netI    0.0779
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3371
_diffrn_reflns_theta_max         20.10
_diffrn_reflns_theta_min         1.33
_diffrn_standards_decay_%        10.5
_diffrn_standards_interval_time  600
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.214
_exptl_absorpt_process_details   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_description       block
_exptl_crystal_F_000             684
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.261
_refine_diff_density_min         -0.160
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.46(15)
_refine_ls_extinction_coef       0.0031(9)
_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_all   1.032
_refine_ls_goodness_of_fit_obs   1.131
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         3163
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.032
_refine_ls_restrained_S_obs      1.131
_refine_ls_R_factor_all          0.0830
_refine_ls_R_factor_obs          0.0412
_refine_ls_shift/esd_max         0.004
_refine_ls_shift/esd_mean        0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1214
_refine_ls_wR_factor_obs         0.0984
_reflns_number_observed          1884
_reflns_number_total             3163
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            804126asup1.cif
_cod_data_source_block           DWDC6
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value 'not measured' was changed to '?' -
the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0582P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_Hall     p_2yb
_cod_original_sg_symbol_H-M      p_1_21_1
_cod_original_formula_sum        'C14 H23 O6 S1'
_cod_database_code               7110353
_exptl_adsorpt_correction_type   none