data_publication_text _publ_requested_journal J.Am.Chem.Soc. _publ_contact_author_name 'Professor Shahriar Mobashery' _publ_contact_author_address ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; _publ_contact_author_email mobashery@nd.edu _publ_contact_author_phone 1(574)6312933 _publ_contact_author_fax 1(574)6316652 loop_ _publ_author_name _publ_author_address 'Hesek, Dusan' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Lee, Mijoon' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Zhang, Welie' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; 'Noll, Bruce C.' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; ' Mobashery, Shahriar' ;University of Notre Dame Department of Chemistry and Biochemistry 251 Nieuwland Science Hall Notre Dame, IN 46556-5670 USA ; data_compound_8 # local ID: data_dh05_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 1,6-anhydro-2-azido-4-O-benzyl-2-deoxy-\b-D-glucopyranose _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N3 O4' _chemical_formula_sum 'C13 H15 N3 O4' _chemical_formula_weight 277.28 _chemical_absolute_configuration ad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_int_tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.7203(3) _cell_length_b 10.1187(4) _cell_length_c 18.5765(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1263.22(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5444 _cell_measurement_theta_min 2.3784 _cell_measurement_theta_max 69.1309 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'clear colorless' _exptl_crystal_size_max 0.41 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.458 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.923 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7063 _exptl_absorpt_correction_T_max 0.7719 _exptl_absorpt_process_details 'Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Siemens KFFCU2K-90' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART Apex CCD diffractometer' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 11708 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0141 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 4.76 _diffrn_reflns_theta_max 69.32 _reflns_number_total 2272 _reflns_number_gt 2269 _reflns_threshold_expression >2sigma(I) _publ_section_references ; Bruker-Nonius AXS. (2007). APEX2 and SAINT. Bruker-Nonius AXS, Madison, Wisconsin, USA. CCDC. (2005). enCIFer. The Cambridge Crystallographic Data Centre, Cambridge, UK. Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2007)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_molecular_graphics 'XP (Sheldrick, 2008)' _computing_publication_material 'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0361P)^2^+0.3116P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0146(7) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.06(15) _refine_ls_number_reflns 2272 _refine_ls_number_parameters 187 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0259 _refine_ls_wR_factor_ref 0.0660 _refine_ls_wR_factor_gt 0.0660 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.22767(18) 1.01546(12) 0.94555(6) 0.0210(3) Uani 1 1 d . . . N2 N 0.29882(17) 1.07649(11) 0.99685(6) 0.0189(3) Uani 1 1 d . . . N3 N 0.3815(2) 1.13801(13) 1.03820(7) 0.0285(3) Uani 1 1 d . . . O1 O -0.30993(14) 0.93508(10) 0.94472(5) 0.0188(2) Uani 1 1 d . . . O3 O -0.04741(15) 0.70251(10) 0.95705(5) 0.0200(2) Uani 1 1 d . . . H3O H 0.028(3) 0.664(2) 0.9847(11) 0.036(5) Uiso 1 1 d . . . O4 O 0.17882(13) 0.85088(9) 0.80395(5) 0.0164(2) Uani 1 1 d . . . O5 O -0.11843(14) 1.02844(9) 0.85853(5) 0.0189(2) Uani 1 1 d . . . C1 C -0.1327(2) 1.01055(13) 0.93352(7) 0.0180(3) Uani 1 1 d . . . H1 H -0.1431 1.0980 0.9583 0.022 Uiso 1 1 calc R . . C2 C 0.0483(2) 0.93414(13) 0.96121(7) 0.0173(3) Uani 1 1 d . . . H2 H 0.0361 0.9196 1.0143 0.021 Uiso 1 1 calc R . . C3 C 0.07159(19) 0.80007(13) 0.92224(7) 0.0147(3) Uani 1 1 d . . . H3 H 0.2142 0.7723 0.9249 0.018 Uiso 1 1 calc R . . C4 C 0.00909(19) 0.80673(13) 0.84256(7) 0.0156(3) Uani 1 1 d . . . H4 H -0.0274 0.7161 0.8257 0.019 Uiso 1 1 calc R . . C5 C -0.1690(2) 0.89946(13) 0.83149(7) 0.0175(3) Uani 1 1 d . . . H5 H -0.2075 0.9038 0.7795 0.021 Uiso 1 1 calc R . . C6 C -0.3470(2) 0.86418(14) 0.87826(7) 0.0192(3) Uani 1 1 d . . . H6A H -0.4728 0.8936 0.8557 0.023 Uiso 1 1 calc R . . H6B H -0.3537 0.7677 0.8868 0.023 Uiso 1 1 calc R . . C7 C 0.1687(2) 0.82731(15) 0.72785(7) 0.0217(3) Uani 1 1 d . . . H7A H 0.0552 0.8760 0.7066 0.026 Uiso 1 1 calc R . . H7B H 0.1504 0.7319 0.7182 0.026 Uiso 1 1 calc R . . C8 C 0.3614(2) 0.87477(14) 0.69566(7) 0.0183(3) Uani 1 1 d . . . C9 C 0.4882(2) 0.78889(15) 0.65915(7) 0.0206(3) Uani 1 1 d . . . H9 H 0.4545 0.6980 0.6551 0.025 Uiso 1 1 calc R . . C10 C 0.6631(2) 0.83505(15) 0.62873(7) 0.0222(3) Uani 1 1 d . . . H10 H 0.7485 0.7759 0.6038 0.027 Uiso 1 1 calc R . . C11 C 0.7138(2) 0.96774(14) 0.63455(7) 0.0209(3) Uani 1 1 d . . . H11 H 0.8327 0.9997 0.6131 0.025 Uiso 1 1 calc R . . C12 C 0.5897(2) 1.05335(14) 0.67201(7) 0.0211(3) Uani 1 1 d . . . H12 H 0.6249 1.1438 0.6768 0.025 Uiso 1 1 calc R . . C13 C 0.4152(2) 1.00725(14) 0.70225(8) 0.0201(3) Uani 1 1 d . . . H13 H 0.3311 1.0664 0.7278 0.024 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0188(6) 0.0250(6) 0.0193(6) -0.0032(5) 0.0003(5) -0.0057(5) N2 0.0173(6) 0.0165(6) 0.0229(6) 0.0016(5) -0.0005(5) 0.0005(5) N3 0.0295(7) 0.0261(7) 0.0298(6) -0.0053(6) -0.0063(6) -0.0068(5) O1 0.0147(4) 0.0236(5) 0.0180(4) -0.0009(4) 0.0016(4) -0.0008(4) O3 0.0211(5) 0.0183(5) 0.0206(5) 0.0070(4) -0.0019(4) -0.0013(4) O4 0.0139(4) 0.0206(5) 0.0147(4) -0.0007(4) 0.0023(4) -0.0016(4) O5 0.0195(5) 0.0165(4) 0.0206(5) 0.0037(4) 0.0011(4) 0.0018(4) C1 0.0194(7) 0.0151(6) 0.0195(6) -0.0003(5) 0.0027(5) -0.0013(5) C2 0.0175(7) 0.0191(7) 0.0153(6) -0.0011(5) 0.0004(5) -0.0026(5) C3 0.0123(6) 0.0151(6) 0.0167(6) 0.0025(5) 0.0003(5) 0.0013(5) C4 0.0141(6) 0.0163(7) 0.0165(6) -0.0004(5) 0.0005(5) -0.0004(5) C5 0.0168(7) 0.0205(7) 0.0150(6) 0.0011(5) -0.0013(5) -0.0002(6) C6 0.0148(6) 0.0246(7) 0.0182(6) -0.0013(5) -0.0018(5) 0.0007(5) C7 0.0190(7) 0.0305(8) 0.0155(6) -0.0040(5) 0.0004(5) -0.0038(6) C8 0.0170(7) 0.0251(7) 0.0129(6) 0.0013(5) -0.0025(5) -0.0009(5) C9 0.0242(7) 0.0198(7) 0.0177(6) -0.0030(5) -0.0004(6) -0.0027(6) C10 0.0206(7) 0.0281(7) 0.0178(6) -0.0045(6) 0.0012(6) 0.0007(6) C11 0.0172(7) 0.0292(7) 0.0163(6) 0.0053(6) 0.0000(5) -0.0022(6) C12 0.0234(7) 0.0182(7) 0.0218(6) 0.0039(6) -0.0057(6) -0.0021(6) C13 0.0185(6) 0.0215(7) 0.0203(6) 0.0009(6) -0.0017(6) 0.0033(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 N2 1.2321(17) . ? N1 C2 1.4880(18) . ? N2 N3 1.1342(17) . ? O1 C1 1.4301(16) . ? O1 C6 1.4494(16) . ? O3 C3 1.4255(16) . ? O3 H3O 0.82(2) . ? O4 C4 1.4195(15) . ? O4 C7 1.4352(15) . ? O5 C1 1.4079(16) . ? O5 C5 1.4393(16) . ? C1 C2 1.5305(19) . ? C1 H1 1.0000 . ? C2 C3 1.5456(17) . ? C2 H2 1.0000 . ? C3 C4 1.5402(17) . ? C3 H3 1.0000 . ? C4 C5 1.5347(19) . ? C4 H4 1.0000 . ? C5 C6 1.5207(19) . ? C5 H5 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.5050(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.393(2) . ? C8 C13 1.394(2) . ? C9 C10 1.385(2) . ? C9 H9 0.9500 . ? C10 C11 1.390(2) . ? C10 H10 0.9500 . ? C11 C12 1.390(2) . ? C11 H11 0.9500 . ? C12 C13 1.381(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C2 116.12(11) . . ? N3 N2 N1 171.51(15) . . ? C1 O1 C6 106.47(10) . . ? C3 O3 H3O 105.8(14) . . ? C4 O4 C7 114.04(10) . . ? C1 O5 C5 102.28(10) . . ? O5 C1 O1 105.62(10) . . ? O5 C1 C2 110.08(11) . . ? O1 C1 C2 110.08(10) . . ? O5 C1 H1 110.3 . . ? O1 C1 H1 110.3 . . ? C2 C1 H1 110.3 . . ? N1 C2 C1 107.38(11) . . ? N1 C2 C3 108.17(10) . . ? C1 C2 C3 111.49(11) . . ? N1 C2 H2 109.9 . . ? C1 C2 H2 109.9 . . ? C3 C2 H2 109.9 . . ? O3 C3 C4 108.25(10) . . ? O3 C3 C2 109.80(10) . . ? C4 C3 C2 112.59(11) . . ? O3 C3 H3 108.7 . . ? C4 C3 H3 108.7 . . ? C2 C3 H3 108.7 . . ? O4 C4 C5 111.51(10) . . ? O4 C4 C3 106.28(10) . . ? C5 C4 C3 111.60(10) . . ? O4 C4 H4 109.1 . . ? C5 C4 H4 109.1 . . ? C3 C4 H4 109.1 . . ? O5 C5 C6 101.49(10) . . ? O5 C5 C4 108.87(11) . . ? C6 C5 C4 113.16(11) . . ? O5 C5 H5 111.0 . . ? C6 C5 H5 111.0 . . ? C4 C5 H5 111.0 . . ? O1 C6 C5 103.62(10) . . ? O1 C6 H6A 111.0 . . ? C5 C6 H6A 111.0 . . ? O1 C6 H6B 111.0 . . ? C5 C6 H6B 111.0 . . ? H6A C6 H6B 109.0 . . ? O4 C7 C8 107.31(11) . . ? O4 C7 H7A 110.3 . . ? C8 C7 H7A 110.3 . . ? O4 C7 H7B 110.3 . . ? C8 C7 H7B 110.3 . . ? H7A C7 H7B 108.5 . . ? C9 C8 C13 118.95(13) . . ? C9 C8 C7 121.37(13) . . ? C13 C8 C7 119.68(13) . . ? C10 C9 C8 120.48(14) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 120.15(13) . . ? C9 C10 H10 119.9 . . ? C11 C10 H10 119.9 . . ? C10 C11 C12 119.59(13) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? C13 C12 C11 120.20(13) . . ? C13 C12 H12 119.9 . . ? C11 C12 H12 119.9 . . ? C12 C13 C8 120.61(13) . . ? C12 C13 H13 119.7 . . ? C8 C13 H13 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C5 O5 C1 O1 -43.07(12) . . . . ? C5 O5 C1 C2 75.74(12) . . . . ? C6 O1 C1 O5 24.00(12) . . . . ? C6 O1 C1 C2 -94.80(12) . . . . ? N2 N1 C2 C1 102.38(13) . . . . ? N2 N1 C2 C3 -137.17(12) . . . . ? O5 C1 C2 N1 61.90(13) . . . . ? O1 C1 C2 N1 177.93(10) . . . . ? O5 C1 C2 C3 -56.43(14) . . . . ? O1 C1 C2 C3 59.60(14) . . . . ? N1 C2 C3 O3 156.59(10) . . . . ? C1 C2 C3 O3 -85.57(13) . . . . ? N1 C2 C3 C4 -82.72(13) . . . . ? C1 C2 C3 C4 35.13(15) . . . . ? C7 O4 C4 C5 -75.23(13) . . . . ? C7 O4 C4 C3 162.95(11) . . . . ? O3 C3 C4 O4 -152.70(10) . . . . ? C2 C3 C4 O4 85.73(12) . . . . ? O3 C3 C4 C5 85.54(13) . . . . ? C2 C3 C4 C5 -36.03(15) . . . . ? C1 O5 C5 C6 43.78(12) . . . . ? C1 O5 C5 C4 -75.80(12) . . . . ? O4 C4 C5 O5 -61.70(13) . . . . ? C3 C4 C5 O5 56.99(13) . . . . ? O4 C4 C5 C6 -173.73(10) . . . . ? C3 C4 C5 C6 -55.05(14) . . . . ? C1 O1 C6 C5 3.62(13) . . . . ? O5 C5 C6 O1 -28.92(12) . . . . ? C4 C5 C6 O1 87.56(12) . . . . ? C4 O4 C7 C8 -177.92(11) . . . . ? O4 C7 C8 C9 119.32(14) . . . . ? O4 C7 C8 C13 -60.71(16) . . . . ? C13 C8 C9 C10 -1.2(2) . . . . ? C7 C8 C9 C10 178.76(12) . . . . ? C8 C9 C10 C11 0.2(2) . . . . ? C9 C10 C11 C12 1.0(2) . . . . ? C10 C11 C12 C13 -1.1(2) . . . . ? C11 C12 C13 C8 0.0(2) . . . . ? C9 C8 C13 C12 1.1(2) . . . . ? C7 C8 C13 C12 -178.84(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_distance_DA _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O3 H3O 0.82(2) 1.98(2) 176 2.7956(14) O1 4_567 ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 69.32 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.186 _refine_diff_density_min -0.188 _refine_diff_density_rms 0.036 _chemical_compound_source synthesized