Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides, sulfamides and sulfamates.
Suthagar, Kajitha; Polson, Matthew I. J.; Fairbanks, Antony J.; Organic & biomolecular chemistry 13 (2015) 6573–6579; doi:10.1039/c5ob00851d

data_7154493
_publ_section_title
;
 Unexpected furanose/pyranose equilibration of N-glycosyl sulfonamides,
 sulfamides and sulfamates.
;
_journal_issue                   23
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              6573
_journal_page_last               6579
_journal_paper_doi               10.1039/c5ob00851d
_journal_volume                  13
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C6 H13 N O6 S'
_chemical_formula_sum            'C6 H13 N O6 S'
_chemical_formula_weight         227.23
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2014-10-15
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2015-03-30 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.14008(6)
_cell_length_b                   9.60877(9)
_cell_length_c                   18.4697(2)
_cell_measurement_reflns_used    25272
_cell_measurement_temperature    120.01(10)
_cell_measurement_theta_max      37.2320
_cell_measurement_theta_min      3.0750
_cell_volume                     912.216(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      120.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6501
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega    4.00   87.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840 -128.0000  158.3039 83

  2 omega   -2.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840   77.0000   30.0000 106

  3 omega  -40.00   52.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840  -57.0000  -90.0000 92

  4 omega   43.00   95.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840   37.0000 -180.0000 52

  5 omega   34.00  115.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840 -178.0000  -60.0000 81

  6 omega   -2.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840   77.0000 -120.0000 106

  7 omega   10.00  103.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840   37.0000    0.0000 93

  8 omega   10.00   71.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840   77.0000  120.0000 61

  9 omega  -43.00   44.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840  -37.0000    0.0000 87

 10 omega -101.00  -53.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.7215  148.0000 -108.5550 48

 11 omega    7.00  103.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840   37.0000    0.0000 96

 12 omega  -20.00   70.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840  -99.0000 -150.0000 90

 13 omega    3.00  100.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840   57.0000  150.0000 97

 14 omega   -2.00  104.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840   77.0000 -150.0000 106

 15 omega -101.00  -35.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.7215  148.0000 -108.5550 66

 16 omega  -53.00   42.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.7215   37.0000  -60.0000 95

 17 omega  -53.00   42.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.7215   37.0000   60.0000 95

 18 omega -101.00   -4.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.7215  -57.0000  -90.0000 97

 19 omega  -43.00   52.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       29.7840  -37.0000  150.0000 95

 20 omega -105.00  -80.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.7215  -77.0000 -150.0000 25

 21 omega  -98.00  -34.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -30.7215  145.0000 -142.8425 64
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0130264000
_diffrn_orient_matrix_UB_12      0.0458536000
_diffrn_orient_matrix_UB_13      -0.0298795000
_diffrn_orient_matrix_UB_21      -0.0653430000
_diffrn_orient_matrix_UB_22      -0.0486670000
_diffrn_orient_matrix_UB_23      -0.0224298000
_diffrn_orient_matrix_UB_31      -0.1208347000
_diffrn_orient_matrix_UB_32      0.0312585000
_diffrn_orient_matrix_UB_33      0.0089079000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0197
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            60915
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.317
_diffrn_reflns_theta_min         3.059
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.361
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.872
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_description       needle
_exptl_crystal_F_000             480
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methanol/diethyl ether'
_exptl_crystal_size_max          0.6961
_exptl_crystal_size_mid          0.0831
_exptl_crystal_size_min          0.0614
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.093
_refine_ls_abs_structure_details
;
 Flack x determined using 1755 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.028(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     140
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.173
_refine_ls_R_factor_all          0.0293
_refine_ls_R_factor_gt           0.0266
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.0491P)^2^+0.0637P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0799
_refine_ls_wR_factor_ref         0.0819
_reflns_Friedel_coverage         0.736
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                4204
_reflns_number_total             4421
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00851d2.cif
_cod_data_source_block           kjk3a
_cod_depositor_comments
'Adding full bibliography for 7154493--7154495.cif.'
_cod_original_cell_volume        912.217(16)
_cod_database_code               7154493
_shelxl_version_number           2013-2
_chemical_oxdiff_formula         C6H13N1O6S1
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     36.23
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N7-H7
 0.9 with sigma of 0.02
 O12-H12
 0.86 with sigma of 0.02
 O13-H13
 0.86 with sigma of 0.02
 O14-H14
 0.86 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B)
3.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_olex2_submission_special_instructions 'No special instructions were received'