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_7154495
_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 syn
_chemical_formula_moiety         '2(C15 H32 N2 O6 S), H2 O'
_chemical_formula_sum            'C30 H66 N4 O13 S2'
_chemical_formula_weight         754.98
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-04-01
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-04-09 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                96.75(3)
_cell_angle_beta                 94.01(3)
_cell_angle_gamma                92.39(3)
_cell_formula_units_Z            2
_cell_length_a                   5.0940(10)
_cell_length_b                   12.212(2)
_cell_length_c                   30.472(6)
_cell_measurement_reflns_used    23752
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.252
_cell_measurement_theta_min      1.350
_cell_volume                     1875.5(6)
_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, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       '\p scans'
_diffrn_radiation_monochromator  'silicon double crystal'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_reflns_av_R_equivalents  0.1353
_diffrn_reflns_av_unetI/netI     0.1850
_diffrn_reflns_Laue_measured_fraction_full 0.914
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            23752
_diffrn_reflns_point_group_measured_fraction_full 0.881
_diffrn_reflns_point_group_measured_fraction_max 0.881
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.252
_diffrn_reflns_theta_min         1.350
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.337
_exptl_crystal_description       needle
_exptl_crystal_F_000             820
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.458
_refine_diff_density_min         -0.555
_refine_diff_density_rms         0.140
_refine_ls_abs_structure_details
;
 Flack x determined using 2095 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.23(12)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     911
_refine_ls_number_reflns         11954
_refine_ls_number_restraints     160
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.1915
_refine_ls_R_factor_gt           0.1302
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[\s^2^(Fo^2^)+(0.2000P)^2^]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3225
_refine_ls_wR_factor_ref         0.3624
_reflns_Friedel_coverage         0.929
_reflns_Friedel_fraction_full    0.849
_reflns_Friedel_fraction_max     0.848
_reflns_number_gt                6746
_reflns_number_total             11954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00851d2.cif
_cod_data_source_block           pp6-1
_cod_depositor_comments
'Adding full bibliography for 7154493--7154495.cif.'
_cod_database_code               7154495
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 H20E-O201
 0.86 with sigma of 0.01
 O201-H20F
 0.86 with sigma of 0.01
 O202-H20D
 0.86 with sigma of 0.01
 H20C-O202
 0.86 with sigma of 0.01
 H20F-H20E
 1.2 with sigma of 0.02
 H20C-H20D
 1.2 with sigma of 0.02
 O43_$1-H9
 2.4 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C75, N74, C76, C77, C78, C79, C80, C81, C82, C83, C84, N44, C45, C46, C47,
 C48, C21, C22, C20, C19, C18, C17, C16, C15, N14, S11, O13, S41, O42, C53, C54
 with sigma for 1-2 distances of 0.0001 and sigma for 1-3 distances of 0.0001
4.a Ternary CH refined with riding coordinates:
 C62(H62), C65(H65), C64(H64), C63(H63), C32(H32), C33(H33), C34(H34),
 C35(H35), C4(H4), C5(H5), C2(H2), C3(H3), C94(H94), C93(H93), C92(H92),
 C95(H95)
4.b Secondary CH2 refined with riding coordinates:
 C76(H76A,H76B), C75(H75A,H75B), C78(H78A,H78B), C77(H77A,H77B), C83(H83A,
 H83B), C79(H79A,H79B), C80(H80A,H80B), C66(H66A,H66B), C82(H82A,H82B),
 C81(H81A,H81B), C48(H48A,H48B), C45(H45A,H45B), C47(H47A,H47B), C51(H51A,H51B),
  C49(H49A,H49B), C36(H36A,H36B), C53(H53A,H53B), C46(H46A,H46B), C50(H50A,
 H50B), C52(H52A,H52B), C19(H19A,H19B), C21(H21A,H21B), C23(H23A,H23B),
 C17(H17A,H17B), C18(H18A,H18B), C15(H15A,H15B), C20(H20A,H20B), C16(H16A,H16B),
  C6(H6A,H6B), C22(H22A,H22B), C109(H10A,H10B), C106(H10C,H10D), C111(H11A,
 H11B), C105(H10E,H10F), C107(H10G,H10H), C112(H11C,H11D), C96(H96A,H96B),
 C108(H10I,H10J), C110(H11H,H11I), C113(H11J,H11K)
4.c Aromatic/amide H refined with riding coordinates:
 N74(H74), N70(H70), N40(H40), N44(H44), N14(H14), N10(H10), N100(H100),
 N104(H104)
4.d Idealised Me refined as rotating group:
 C84(H84A,H84B,H84C), C54(H54A,H54B,H54C), C24(H24A,H24B,H24C), C114(H11E,H11F,
 H11G)
4.e Idealised tetrahedral OH refined as rotating group:
 O67(H67), O68(H68), O69(H69), O37(H37), O39(H39), O38(H38), O7(H7), O9(H9),
 O8(H8), O98(H98), O97(H97), O99(H99)
;
_olex2_submission_special_instructions 'No special instructions were received'