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_7154494
_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         'C26 H28 O5'
_chemical_formula_sum            'C26 H28 O5'
_chemical_formula_weight         420.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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
;
2015-04-16 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.36(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.7090(9)
_cell_length_b                   38.306(8)
_cell_length_c                   11.942(2)
_cell_measurement_reflns_used    1484
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      18.2
_cell_measurement_theta_min      2.04
_cell_volume                     2154.1(7)
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_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_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.7108
_diffrn_reflns_av_R_equivalents  0.0889
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       48
_diffrn_reflns_limit_k_min       -48
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10557
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        26.550
_diffrn_reflns_theta_max         26.550
_diffrn_reflns_theta_min         1.063
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_description       needle
_exptl_crystal_F_000             896
_exptl_crystal_size_max          0.505
_exptl_crystal_size_mid          0.022
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.496
_refine_diff_density_min         -0.526
_refine_diff_density_rms         0.126
_refine_ls_abs_structure_details
;
 Flack x determined using 3136 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.1(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         8786
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.125
_refine_ls_R_factor_all          0.1008
_refine_ls_R_factor_gt           0.0840
_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^)+(0.0932P)^2^+3.6517P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2101
_refine_ls_wR_factor_ref         0.2231
_reflns_Friedel_coverage         0.968
_reflns_Friedel_fraction_full    0.984
_reflns_Friedel_fraction_max     0.984
_reflns_number_gt                7284
_reflns_number_total             8786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c5ob00851d2.cif
_cod_data_source_block           kja2r-m
_cod_depositor_comments
'Adding full bibliography for 7154493--7154495.cif.'
_cod_database_code               7154494
_shelxl_version_number           2013-2
_olex2_refinement_description
;
1. Others
 Fixed Sof: C25(0.5) H25(0.5) C23(0.5) H23(0.5) C24(0.5) H24(0.5) C22(0.5)
 H22(0.5) C26(0.5) H26(0.5) C19(0.5) H19(0.5) C18(0.5) H18(0.5) C27(0.5)
 H27(0.5) C21(0.5) H21(0.5) C20(0.5) H20(0.5)
 Fixed Uiso: H2(0.028) H67A(0.044) H67B(0.044) H54(0.03) H52(0.027) H5(0.028)
 H4(0.031) H57A(0.037) H57B(0.037) H80(0.046) H77(0.044) H29A(0.047)
 H29B(0.047) H53(0.032) H55(0.028) H3(0.035) H69(0.049) H6A(0.038) H6B(0.038)
 H59A(0.053) H59B(0.053) H70(0.077) H14(0.056) H65(0.079) H71(0.077) H79(0.064)
 H61(0.061) H25(0.058) H33(0.074) H73(0.057) H81(0.061) H72(0.075) H31(0.059)
 H63(0.065) H23(0.04) H16A(0.063) H16B(0.063) H8A(0.058) H8B(0.058) H64(0.065)
 H12(0.071) H35(0.075) H11(0.075) H13(0.082) H75A(0.078) H75B(0.078) H78(0.075)
 H24(0.06) H34(0.081) H10(0.074) H32(0.077) H22(0.047) H62(0.104) H26(0.054)
 H19(0.042) H18(0.038) H27(0.037) H21(0.052) H20(0.051) H003(0.051) H56(0.051)
 Fixed X: H2(1.0736) H67A(0.2058) H67B(0.2817) H54(0.6725) H52(0.5866)
 H5(1.0073) H4(1.1517) H57A(0.1146) H57B(0.014) H80(0.3826) H77(0.1197)
 H29A(0.9414) H29B(1.1615) H53(0.146) H55(0.5214) H3(0.6201) H69(0.5639)
 H6A(0.5996) H6B(0.4953) H59A(-0.1077) H59B(0.0014) H70(0.9051) H14(0.9499)
 H65(-0.0461) H71(1.1193) H79(0.043) H61(0.4433) H25(1.6166) H33(0.55)
 H73(0.6515) H81(0.5762) H72(0.9896) H31(0.5834) H63(0.4503) H23(1.0331)
 H16A(0.6672) H16B(0.7551) H8A(0.384) H8B(0.5025) H64(0.1227) H12(0.9856)
 H35(1.053) H11(0.6444) H13(1.132) H75A(0.4983) H75B(0.685) H78(-0.0875)
 H24(1.3987) H34(0.8684) H10(0.4626) H32(0.4069) H22(1.2111) H62(0.6095)
 H26(1.4348) H19(1.265) H18(0.943) H27(1.0765) H21(1.4666) H20(1.5452)
 Fixed Y: H2(0.552) H67A(0.3559) H67B(0.3501) H54(0.4129) H52(0.4492)
 H5(0.5408) H4(0.5906) H57A(0.4488) H57B(0.4703) H80(0.2989) H77(0.3323)
 H29A(0.6044) H29B(0.6255) H53(0.4094) H55(0.4629) H3(0.591) H69(0.3364)
 H6A(0.5511) H6B(0.5296) H59A(0.5181) H59B(0.4952) H70(0.2943) H14(0.4435)
 H65(0.5413) H71(0.262) H79(0.2668) H61(0.5579) H25(0.7336) H33(0.7414)
 H73(0.3126) H81(0.3489) H72(0.2707) H31(0.6677) H63(0.6258) H23(0.669)
 H16A(0.6446) H16B(0.6515) H8A(0.4818) H8B(0.5047) H64(0.5922) H12(0.3755)
 H35(0.6565) H11(0.4083) H13(0.3927) H75A(0.3974) H75B(0.3749) H78(0.2838)
 H24(0.7127) H34(0.7095) H10(0.4587) H32(0.7209) H22(0.6982) H62(0.6083)
 H26(0.7243) H19(0.6922) H18(0.6551) H27(0.6817) H21(0.7407) H20(0.7318)
 Fixed Z: H2(0.843) H67A(0.3969) H67B(0.5268) H54(0.6408) H52(0.4249)
 H5(0.5333) H4(0.6325) H57A(0.3498) H57B(0.458) H80(1.072) H77(0.7111)
 H29A(0.4115) H29B(0.4894) H53(0.5228) H55(0.7359) H3(0.7503) H69(0.2536)
 H6A(0.9218) H6B(0.8135) H59A(0.334) H59B(0.2304) H70(0.2068) H14(0.9075)
 H65(0.0916) H71(0.3501) H79(0.975) H61(0.3612) H25(0.8757) H33(0.3205)
 H73(0.5806) H81(0.9925) H72(0.5378) H31(0.5619) H63(0.1013) H23(1.0228)
 H16A(0.8736) H16B(0.7457) H8A(0.9401) H8B(1.043) H64(0.01) H12(1.1679)
 H35(0.2822) H11(1.2622) H13(0.9895) H75A(0.8539) H75B(0.7687) H78(0.7952)
 H24(1.0448) H34(0.2136) H10(1.1798) H32(0.4921) H22(0.7285) H62(0.2775)
 H26(0.7137) H19(1.1163) H18(1.0217) H27(0.6853) H21(0.8379) H20(1.014)
;
_olex2_submission_special_instructions 'No special instructions were received'