data_0463sejk _ccdc_journal_manuscript_code jo-2010-00362n _publ_requested_journal J.Org.Chem. _publ_contact_author_name 'Herwig BERTHOLD' _publ_contact_author_address ;University of Hamburg Department of Chemistry Martin-Luther-King-Platz 6 20146 Hamburg Germany ; _publ_contact_author_email berthold@chemie.uni-hamburg.de _publ_contact_author_phone 49(40)34832205 _publ_contact_author_fax 49(40)42838x4325 loop_ _publ_author_name _publ_author_address 'Berthold, Herwig Josef' ;University of Hamburg Department of Chemistry Martin-Luther-King-Platz 6 20146 Hamburg Germany ; 'Thiem, Joachim' ;Department of Chemistry University of Hamburg Martin-Luther-King-Platz 6 20146 Hamburg Germany ; 'Schotten, Theo' ;CAN GmbH Grindelallee 117 20146 Hamburg Germany ; 'Hoffmann, Frank' ;University of Hamburg Department of Chemistry Martin-Luther-King-Platz 6 20146 Hamburg Germany ; 'Franke, Stephan' ;University of Hamburg Department of Chemistry Martin-Luther-King-Platz 6 20146 Hamburg Germany ; _audit_update_record ; 2010-04-14 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic '2,3,4,6-tetra-O-acetyl-\b-D-glucopyranosyl azide' _chemical_name_common 2,3,4,6-tetra-O-acetyl-\b-D-glucopyranosyl_azide _chemical_formula_moiety 'C14 H19 N3 O9' _chemical_formula_sum 'C14 H19 N3 O9' _exptl_crystal_recrystallization_method 'ethyl acetate / diethyl ether' _chemical_melting_point 400 _exptl_crystal_description block _exptl_crystal_colour grayish_colourless _diffrn_ambient_temperature 153(2) _chemical_formula_weight 373.32 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 '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 0.0061 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 '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_int_tables_number 19 _chemical_absolute_configuration ad _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.3509(4) _cell_length_b 14.7643(7) _cell_length_c 15.9289(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1728.78(15) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 412 _cell_measurement_theta_min 1.2 _cell_measurement_theta_max 27.0 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.121 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9497 _exptl_absorpt_correction_T_max 0.9715 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 1998)' _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX CCD area detector' _diffrn_measurement_method omega-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number none _diffrn_standards_interval_count none _diffrn_standards_interval_time none _diffrn_standards_decay_% 0 _diffrn_reflns_number 47253 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.88 _diffrn_reflns_theta_max 32.50 _reflns_number_total 3527 _reflns_number_gt 3195 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker AXS, 1998)' _computing_cell_refinement 'SAINT (Bruker AXS, 1998)' _computing_data_reduction 'SAINT (Bruker AXS, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0646P)^2^+0.0913P] 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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _refine_ls_number_reflns 3527 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0420 _refine_ls_R_factor_gt 0.0387 _refine_ls_wR_factor_ref 0.0953 _refine_ls_wR_factor_gt 0.0938 _refine_ls_goodness_of_fit_ref 0.991 _refine_ls_restrained_S_all 0.991 _refine_ls_shift/su_max 0.027 _refine_ls_shift/su_mean 0.001 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 O41 O 0.29141(12) 0.42963(7) -0.03703(6) 0.02041(18) Uani 1 1 d . . . O5 O 0.65249(13) 0.52370(6) 0.09103(6) 0.01983(18) Uani 1 1 d . . . O61 O 0.47745(14) 0.63721(6) -0.03069(6) 0.02345(19) Uani 1 1 d . . . O21 O 0.57287(14) 0.31839(6) 0.21318(6) 0.0232(2) Uani 1 1 d . . . O31 O 0.23709(13) 0.34297(6) 0.12997(6) 0.02163(19) Uani 1 1 d . . . O32 O 0.23348(17) 0.22830(8) 0.03616(7) 0.0355(3) Uani 1 1 d . . . O42 O 0.02117(16) 0.47832(10) 0.01215(8) 0.0401(3) Uani 1 1 d . . . O22 O 0.4607(2) 0.36350(8) 0.33815(7) 0.0458(3) Uani 1 1 d . . . O62 O 0.5333(2) 0.69032(10) -0.15930(8) 0.0506(4) Uani 1 1 d . . . N11 N 0.77895(17) 0.48975(9) 0.22119(7) 0.0274(3) Uani 1 1 d . . . N12 N 0.94400(18) 0.50733(9) 0.21343(8) 0.0294(3) Uani 1 1 d . . . N13 N 1.0913(2) 0.52643(13) 0.21661(11) 0.0470(4) Uani 1 1 d . . . C5 C 0.57290(17) 0.48915(8) 0.01539(8) 0.0179(2) Uani 1 1 d . . . H5 H 0.6447 0.4350 -0.0027 0.021 Uiso 1 1 calc R . . C31 C 0.16806(19) 0.26591(9) 0.09638(8) 0.0224(2) Uani 1 1 d . . . C3 C 0.40726(18) 0.37601(8) 0.09687(8) 0.0186(2) Uani 1 1 d . . . H3 H 0.4693 0.3263 0.0653 0.022 Uiso 1 1 calc R . . C2 C 0.52216(18) 0.40201(8) 0.17284(8) 0.0195(2) Uani 1 1 d . . . H2 H 0.4502 0.4408 0.2122 0.023 Uiso 1 1 calc R . . C6 C 0.58421(19) 0.55895(8) -0.05303(8) 0.0211(2) Uani 1 1 d . . . H6A H 0.7126 0.5770 -0.0615 0.025 Uiso 1 1 calc R . . H6B H 0.5383 0.5330 -0.1063 0.025 Uiso 1 1 calc R . . C1 C 0.69611(17) 0.45086(8) 0.14596(8) 0.0203(2) Uani 1 1 d . . . H1 H 0.7819 0.4077 0.1181 0.024 Uiso 1 1 calc R . . C41 C 0.10949(18) 0.44539(10) -0.04319(9) 0.0242(3) Uani 1 1 d . . . C4 C 0.38124(16) 0.45732(8) 0.03889(7) 0.0175(2) Uani 1 1 d . . . H4 H 0.3118 0.5066 0.0677 0.021 Uiso 1 1 calc R . . C42 C 0.0411(2) 0.41498(11) -0.12673(9) 0.0297(3) Uani 1 1 d . . . H42A H 0.0513 0.3489 -0.1308 0.044 Uiso 1 1 calc R . . H42B H 0.1138 0.4432 -0.1712 0.044 Uiso 1 1 calc R . . H42C H -0.0865 0.4328 -0.1331 0.044 Uiso 1 1 calc R . . C61 C 0.4665(2) 0.70063(11) -0.09171(10) 0.0297(3) Uani 1 1 d . . . C32 C 0.0038(2) 0.23483(11) 0.14321(10) 0.0320(3) Uani 1 1 d . . . H32A H -0.1043 0.2426 0.1079 0.048 Uiso 1 1 calc R . . H32B H -0.0097 0.2707 0.1946 0.048 Uiso 1 1 calc R . . H32C H 0.0175 0.1707 0.1579 0.048 Uiso 1 1 calc R . . C21 C 0.5295(2) 0.30641(10) 0.29565(8) 0.0278(3) Uani 1 1 d . . . C22 C 0.5769(3) 0.21234(11) 0.32230(10) 0.0373(4) Uani 1 1 d . . . H22A H 0.5833 0.2096 0.3837 0.056 Uiso 1 1 calc R . . H22B H 0.6950 0.1954 0.2984 0.056 Uiso 1 1 calc R . . H22C H 0.4834 0.1703 0.3022 0.056 Uiso 1 1 calc R . . C62 C 0.3687(3) 0.78308(12) -0.06222(13) 0.0460(4) Uani 1 1 d . . . H62A H 0.4449 0.8158 -0.0218 0.069 Uiso 1 1 calc R . . H62B H 0.2544 0.7653 -0.0352 0.069 Uiso 1 1 calc R . . H62C H 0.3424 0.8224 -0.1103 0.069 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 O41 0.0204(4) 0.0235(4) 0.0173(4) -0.0033(3) -0.0017(3) 0.0020(3) O5 0.0244(4) 0.0154(4) 0.0197(4) 0.0004(3) -0.0018(4) -0.0021(3) O61 0.0298(5) 0.0197(4) 0.0208(4) 0.0028(3) 0.0039(4) 0.0059(4) O21 0.0314(5) 0.0204(4) 0.0179(4) 0.0038(3) 0.0006(4) 0.0002(4) O31 0.0239(4) 0.0198(4) 0.0212(4) -0.0030(3) 0.0030(4) -0.0058(3) O32 0.0390(6) 0.0321(5) 0.0354(5) -0.0153(5) 0.0088(5) -0.0122(5) O42 0.0245(5) 0.0625(8) 0.0333(6) -0.0104(6) 0.0027(5) 0.0076(5) O22 0.0786(10) 0.0331(6) 0.0257(5) 0.0004(5) 0.0142(6) 0.0040(7) O62 0.0679(9) 0.0506(7) 0.0332(6) 0.0208(6) 0.0148(6) 0.0174(7) N11 0.0270(6) 0.0341(6) 0.0212(5) -0.0028(5) -0.0028(5) -0.0067(5) N12 0.0305(6) 0.0310(6) 0.0268(6) -0.0053(5) -0.0032(5) -0.0023(5) N13 0.0303(7) 0.0640(11) 0.0466(9) -0.0203(8) -0.0018(7) -0.0109(7) C5 0.0199(5) 0.0164(5) 0.0173(5) -0.0008(4) 0.0018(4) -0.0003(4) C31 0.0259(6) 0.0195(5) 0.0217(5) -0.0007(5) -0.0024(5) -0.0042(5) C3 0.0203(5) 0.0178(5) 0.0177(5) -0.0009(4) 0.0014(4) -0.0023(4) C2 0.0237(5) 0.0170(5) 0.0177(5) 0.0007(4) -0.0005(5) -0.0015(4) C6 0.0260(6) 0.0185(5) 0.0187(5) 0.0008(4) 0.0046(5) 0.0024(5) C1 0.0228(5) 0.0184(5) 0.0198(5) 0.0002(4) -0.0022(5) -0.0013(5) C41 0.0210(6) 0.0278(6) 0.0240(6) 0.0016(5) -0.0015(5) -0.0003(5) C4 0.0193(5) 0.0175(5) 0.0157(5) -0.0009(4) 0.0007(4) -0.0002(4) C42 0.0281(6) 0.0352(7) 0.0257(6) 0.0002(6) -0.0065(6) -0.0015(6) C61 0.0304(7) 0.0285(7) 0.0301(7) 0.0108(5) 0.0010(6) 0.0042(6) C32 0.0330(7) 0.0317(7) 0.0314(7) -0.0043(6) 0.0054(6) -0.0137(6) C21 0.0391(7) 0.0257(6) 0.0185(5) 0.0020(5) 0.0006(6) -0.0069(6) C22 0.0590(10) 0.0287(7) 0.0241(6) 0.0086(6) 0.0016(7) -0.0013(8) C62 0.0521(11) 0.0312(8) 0.0548(11) 0.0115(8) 0.0033(9) 0.0183(8) _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 O41 C41 1.3609(16) . ? O41 C4 1.4372(15) . ? O5 C1 1.4230(15) . ? O5 C5 1.4332(15) . ? O61 C61 1.3519(16) . ? O61 C6 1.4414(16) . ? O21 C21 1.3634(16) . ? O21 C2 1.4408(15) . ? O31 C31 1.3559(15) . ? O31 C3 1.4424(15) . ? O32 C31 1.2082(17) . ? O42 C41 1.1979(18) . ? O22 C21 1.193(2) . ? O62 C61 1.193(2) . ? N11 N12 1.2469(18) . ? N11 C1 1.4617(17) . ? N12 N13 1.120(2) . ? C5 C6 1.5022(17) . ? C5 C4 1.5316(17) . ? C5 H5 1.0000 . ? C31 C32 1.492(2) . ? C3 C2 1.5248(17) . ? C3 C4 1.5268(17) . ? C3 H3 1.0000 . ? C2 C1 1.5293(18) . ? C2 H2 1.0000 . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C1 H1 1.0000 . ? C41 C42 1.492(2) . ? C4 H4 1.0000 . ? C42 H42A 0.9800 . ? C42 H42B 0.9800 . ? C42 H42C 0.9800 . ? C61 C62 1.490(2) . ? C32 H32A 0.9800 . ? C32 H32B 0.9800 . ? C32 H32C 0.9800 . ? C21 C22 1.494(2) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? 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 C41 O41 C4 117.61(10) . . ? C1 O5 C5 109.87(9) . . ? C61 O61 C6 114.22(10) . . ? C21 O21 C2 118.70(11) . . ? C31 O31 C3 117.65(10) . . ? N12 N11 C1 113.95(12) . . ? N13 N12 N11 171.34(16) . . ? O5 C5 C6 110.07(10) . . ? O5 C5 C4 106.22(9) . . ? C6 C5 C4 116.02(11) . . ? O5 C5 H5 108.1 . . ? C6 C5 H5 108.1 . . ? C4 C5 H5 108.1 . . ? O32 C31 O31 123.37(13) . . ? O32 C31 C32 125.30(13) . . ? O31 C31 C32 111.33(12) . . ? O31 C3 C2 105.99(10) . . ? O31 C3 C4 112.23(10) . . ? C2 C3 C4 110.58(10) . . ? O31 C3 H3 109.3 . . ? C2 C3 H3 109.3 . . ? C4 C3 H3 109.3 . . ? O21 C2 C3 106.35(9) . . ? O21 C2 C1 108.22(10) . . ? C3 C2 C1 111.08(10) . . ? O21 C2 H2 110.4 . . ? C3 C2 H2 110.4 . . ? C1 C2 H2 110.4 . . ? O61 C6 C5 109.92(10) . . ? O61 C6 H6A 109.7 . . ? C5 C6 H6A 109.7 . . ? O61 C6 H6B 109.7 . . ? C5 C6 H6B 109.7 . . ? H6A C6 H6B 108.2 . . ? O5 C1 N11 107.53(10) . . ? O5 C1 C2 109.89(10) . . ? N11 C1 C2 107.70(10) . . ? O5 C1 H1 110.5 . . ? N11 C1 H1 110.5 . . ? C2 C1 H1 110.5 . . ? O42 C41 O41 123.29(13) . . ? O42 C41 C42 126.59(13) . . ? O41 C41 C42 110.11(12) . . ? O41 C4 C3 110.06(10) . . ? O41 C4 C5 107.71(9) . . ? C3 C4 C5 105.90(10) . . ? O41 C4 H4 111.0 . . ? C3 C4 H4 111.0 . . ? C5 C4 H4 111.0 . . ? C41 C42 H42A 109.5 . . ? C41 C42 H42B 109.5 . . ? H42A C42 H42B 109.5 . . ? C41 C42 H42C 109.5 . . ? H42A C42 H42C 109.5 . . ? H42B C42 H42C 109.5 . . ? O62 C61 O61 122.40(14) . . ? O62 C61 C62 125.97(15) . . ? O61 C61 C62 111.59(14) . . ? C31 C32 H32A 109.5 . . ? C31 C32 H32B 109.5 . . ? H32A C32 H32B 109.5 . . ? C31 C32 H32C 109.5 . . ? H32A C32 H32C 109.5 . . ? H32B C32 H32C 109.5 . . ? O22 C21 O21 123.66(14) . . ? O22 C21 C22 126.47(14) . . ? O21 C21 C22 109.86(13) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? 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 C1 N11 N12 N13 -178(100) . . . . ? C1 O5 C5 C6 -161.04(10) . . . . ? C1 O5 C5 C4 72.61(12) . . . . ? C3 O31 C31 O32 -6.36(19) . . . . ? C3 O31 C31 C32 173.62(11) . . . . ? C31 O31 C3 C2 -135.17(11) . . . . ? C31 O31 C3 C4 104.02(12) . . . . ? C21 O21 C2 C3 -123.71(12) . . . . ? C21 O21 C2 C1 116.87(13) . . . . ? O31 C3 C2 O21 70.64(12) . . . . ? C4 C3 C2 O21 -167.49(10) . . . . ? O31 C3 C2 C1 -171.83(10) . . . . ? C4 C3 C2 C1 -49.96(13) . . . . ? C61 O61 C6 C5 -174.58(12) . . . . ? O5 C5 C6 O61 -63.97(14) . . . . ? C4 C5 C6 O61 56.64(14) . . . . ? C5 O5 C1 N11 179.17(10) . . . . ? C5 O5 C1 C2 -63.87(12) . . . . ? N12 N11 C1 O5 -82.00(15) . . . . ? N12 N11 C1 C2 159.61(12) . . . . ? O21 C2 C1 O5 168.00(9) . . . . ? C3 C2 C1 O5 51.61(13) . . . . ? O21 C2 C1 N11 -75.15(12) . . . . ? C3 C2 C1 N11 168.46(11) . . . . ? C4 O41 C41 O42 -2.3(2) . . . . ? C4 O41 C41 C42 178.27(11) . . . . ? C41 O41 C4 C3 99.83(13) . . . . ? C41 O41 C4 C5 -145.16(11) . . . . ? O31 C3 C4 O41 -68.63(12) . . . . ? C2 C3 C4 O41 173.25(10) . . . . ? O31 C3 C4 C5 175.22(9) . . . . ? C2 C3 C4 C5 57.10(12) . . . . ? O5 C5 C4 O41 174.97(9) . . . . ? C6 C5 C4 O41 52.31(13) . . . . ? O5 C5 C4 C3 -67.30(11) . . . . ? C6 C5 C4 C3 170.04(10) . . . . ? C6 O61 C61 O62 3.1(2) . . . . ? C6 O61 C61 C62 -174.93(14) . . . . ? C2 O21 C21 O22 -4.5(2) . . . . ? C2 O21 C21 C22 174.21(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 32.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.385 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.057