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_30 # local ID: data_dh80_0ma _audit_creation_method SHELXL-97 _chemical_name_systematic ? _chemical_name_common 'Azido tetraacetyl 2-deoxy-\b-D-glucopyranose' _chemical_melting_point ? _chemical_formula_moiety 'C18 H22 N4 O9' _chemical_formula_sum 'C18 H22 N4 O9' _chemical_formula_weight 438.40 _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 2' _symmetry_space_group_name_Hall 'P 2 2ab' _symmetry_int_tables_number 18 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z' '-x, -y, z' _cell_length_a 17.5877(2) _cell_length_b 21.7941(2) _cell_length_c 5.7479(1) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2203.22(5) _cell_formula_units_Z 4 _cell_measurement_temperature 291(2) _cell_measurement_reflns_used 5487 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 52.27 _exptl_crystal_description plate _exptl_crystal_colour 'clear colorless' _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.919 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_process_details 'Sheldrick, G. M. (2007). SADABS. University of G\"ottingen, Germany.' _exptl_special_details ; ? ; _diffrn_ambient_temperature 291(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 20360 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 69.77 _reflns_number_total 4020 _reflns_number_gt 3453 _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^)+(0.0478P)^2^+0.1972P] 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 constr _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 0.01(19) _refine_ls_number_reflns 4020 _refine_ls_number_parameters 309 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0398 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0899 _refine_ls_wR_factor_gt 0.0856 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _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 0.19006(9) 0.65203(7) 0.4334(3) 0.0639(4) Uani 1 1 d . . . N2 N 0.15505(9) 0.67266(7) 0.2632(4) 0.0662(4) Uani 1 1 d . . . N3 N 0.12226(12) 0.69775(10) 0.1241(5) 0.0928(6) Uani 1 1 d . . . N4 N 0.33048(8) 0.61637(6) 0.6475(3) 0.0552(4) Uani 1 1 d . . . O3 O 0.32409(6) 0.49276(6) 0.8298(2) 0.0583(3) Uani 1 1 d . A . O4 O 0.24725(7) 0.40535(5) 0.5271(3) 0.0672(4) Uani 1 1 d . . . O5 O 0.15742(7) 0.55012(5) 0.3778(2) 0.0580(3) Uani 1 1 d . . . O6 O 0.06405(7) 0.44850(6) 0.5021(3) 0.0712(4) Uani 1 1 d . B . O7 O 0.4324(11) 0.4590(17) 0.676(4) 0.115(5) Uani 0.40(5) 1 d P A 1 O7' O 0.4160(11) 0.4406(8) 0.6500(19) 0.106(3) Uani 0.60(5) 1 d P A 2 O9 O 0.19403(14) 0.37548(9) 0.8633(4) 0.1280(8) Uani 1 1 d . . . O11 O 0.048(2) 0.3482(4) 0.460(3) 0.141(7) Uani 0.49(4) 1 d P B 1 O11' O 0.0107(6) 0.3630(8) 0.388(2) 0.097(4) Uani 0.51(4) 1 d P B 2 O21 O 0.28553(8) 0.66729(6) 0.9713(2) 0.0719(4) Uani 1 1 d . . . O24 O 0.40495(8) 0.59454(7) 0.3270(3) 0.0721(4) Uani 1 1 d . . . C1 C 0.22051(10) 0.59075(7) 0.3986(3) 0.0540(4) Uani 1 1 d . . . H1 H 0.2524 0.5892 0.2590 0.065 Uiso 1 1 calc R . . C2 C 0.26658(9) 0.57497(7) 0.6147(3) 0.0515(4) Uani 1 1 d . . . H2 H 0.2329 0.5798 0.7494 0.062 Uiso 1 1 calc R . . C3 C 0.29167(9) 0.50786(7) 0.6073(3) 0.0513(4) Uani 1 1 d . . . H3 H 0.3294 0.5018 0.4839 0.062 Uiso 1 1 calc R . . C4 C 0.22274(10) 0.46765(7) 0.5639(3) 0.0527(4) Uani 1 1 d . . . H4 H 0.1885 0.4695 0.6981 0.063 Uiso 1 1 calc R . . C5 C 0.18078(10) 0.48783(7) 0.3462(3) 0.0570(4) Uani 1 1 d . . . H5 H 0.2153 0.4854 0.2128 0.068 Uiso 1 1 calc R . . C6 C 0.11091(12) 0.45018(9) 0.2964(4) 0.0684(5) Uani 1 1 d . . . H6A H 0.0828 0.4682 0.1684 0.082 Uiso 1 1 calc R . . H6B H 0.1255 0.4088 0.2526 0.082 Uiso 1 1 calc R . . C7 C 0.39079(13) 0.46098(10) 0.8318(4) 0.0722(5) Uani 1 1 d . . . C8 C 0.41370(15) 0.44558(13) 1.0704(5) 0.0949(8) Uani 1 1 d . A . H8A H 0.4612 0.4239 1.0673 0.142 Uiso 1 1 calc R . . H8B H 0.3755 0.4202 1.1408 0.142 Uiso 1 1 calc R . . H8C H 0.4193 0.4826 1.1593 0.142 Uiso 1 1 calc R . . C9 C 0.22607(14) 0.36260(9) 0.6863(5) 0.0827(7) Uani 1 1 d . . . C10 C 0.24859(19) 0.30056(11) 0.6049(8) 0.1261(12) Uani 1 1 d . . . H10A H 0.2082 0.2832 0.5140 0.189 Uiso 1 1 calc R . . H10B H 0.2585 0.2747 0.7368 0.189 Uiso 1 1 calc R . . H10C H 0.2936 0.3036 0.5113 0.189 Uiso 1 1 calc R . . C11 C 0.02443(13) 0.39822(10) 0.5418(5) 0.0802(6) Uani 1 1 d . . . C12 C -0.01980(14) 0.40137(13) 0.7599(5) 0.0905(7) Uani 1 1 d . B . H12A H 0.0125 0.3912 0.8889 0.136 Uiso 1 1 calc R . . H12B H -0.0613 0.3728 0.7526 0.136 Uiso 1 1 calc R . . H12C H -0.0393 0.4422 0.7799 0.136 Uiso 1 1 calc R . . C21 C 0.33293(10) 0.66056(7) 0.8227(3) 0.0561(4) Uani 1 1 d . . . C22 C 0.40448(11) 0.69616(8) 0.7883(3) 0.0595(5) Uani 1 1 d . . . C23 C 0.44038(10) 0.67388(8) 0.6053(4) 0.0601(5) Uani 1 1 d . . . C24 C 0.39355(10) 0.62354(8) 0.5025(3) 0.0561(4) Uani 1 1 d . . . C25 C 0.42397(15) 0.74730(11) 0.9498(5) 0.0868(7) Uani 1 1 d . . . H25A H 0.4172 0.7339 1.1076 0.124(11) Uiso 1 1 calc R . . H25B H 0.3913 0.7817 0.9197 0.145(13) Uiso 1 1 calc R . . H25C H 0.4760 0.7592 0.9262 0.142(12) Uiso 1 1 calc R . . C26 C 0.51532(11) 0.69217(11) 0.5023(5) 0.0834(7) Uani 1 1 d . . . H26A H 0.5550 0.6676 0.5691 0.125 Uiso 1 1 calc R . . H26B H 0.5249 0.7347 0.5349 0.125 Uiso 1 1 calc R . . H26C H 0.5141 0.6860 0.3370 0.125 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 0.0689(10) 0.0480(8) 0.0747(11) 0.0036(7) 0.0015(8) 0.0047(7) N2 0.0551(9) 0.0512(8) 0.0921(13) 0.0013(9) 0.0039(9) 0.0006(8) N3 0.0806(12) 0.0834(12) 0.1143(17) 0.0078(12) -0.0163(13) 0.0230(10) N4 0.0514(8) 0.0501(8) 0.0643(9) -0.0059(6) 0.0121(7) -0.0072(6) O3 0.0551(7) 0.0618(7) 0.0579(7) -0.0001(5) 0.0005(6) 0.0056(6) O4 0.0716(8) 0.0422(6) 0.0877(9) -0.0033(6) 0.0038(7) 0.0024(5) O5 0.0525(6) 0.0479(6) 0.0737(8) 0.0022(6) -0.0019(6) -0.0023(5) O6 0.0620(7) 0.0576(7) 0.0940(10) -0.0077(7) 0.0027(7) -0.0122(6) O7 0.071(6) 0.195(13) 0.079(7) -0.003(7) 0.015(4) 0.036(8) O7' 0.114(6) 0.127(6) 0.078(3) -0.017(3) -0.013(4) 0.076(5) O9 0.171(2) 0.0775(11) 0.1354(17) 0.0339(11) 0.0601(17) 0.0141(12) O11 0.193(17) 0.060(3) 0.171(7) -0.011(4) 0.031(10) -0.031(5) O11' 0.086(5) 0.080(5) 0.123(5) -0.037(3) 0.007(3) -0.035(3) O21 0.0829(9) 0.0629(7) 0.0698(9) -0.0084(7) 0.0233(8) -0.0115(7) O24 0.0617(8) 0.0750(8) 0.0797(9) -0.0151(8) 0.0203(7) -0.0053(7) C1 0.0542(9) 0.0438(9) 0.0639(11) 0.0020(7) 0.0086(8) -0.0028(7) C2 0.0484(9) 0.0465(8) 0.0596(10) -0.0019(8) 0.0095(8) -0.0062(7) C3 0.0513(9) 0.0493(9) 0.0532(10) 0.0013(7) 0.0039(7) 0.0006(7) C4 0.0551(9) 0.0413(8) 0.0617(11) -0.0006(7) 0.0049(8) 0.0002(7) C5 0.0599(10) 0.0476(9) 0.0636(11) -0.0024(8) 0.0039(9) -0.0028(8) C6 0.0720(12) 0.0606(11) 0.0728(13) -0.0057(9) -0.0054(10) -0.0080(9) C7 0.0679(13) 0.0755(13) 0.0733(14) -0.0014(11) -0.0026(12) 0.0182(10) C8 0.0901(16) 0.1103(18) 0.0845(17) -0.0003(13) -0.0166(13) 0.0275(15) C9 0.0756(14) 0.0492(11) 0.123(2) 0.0119(12) 0.0040(15) 0.0009(10) C10 0.122(2) 0.0494(12) 0.207(4) 0.0126(17) 0.016(3) 0.0105(13) C11 0.0794(14) 0.0632(13) 0.0982(18) 0.0001(12) -0.0082(13) -0.0188(11) C12 0.0745(15) 0.1027(18) 0.0945(17) 0.0148(14) -0.0095(12) -0.0266(13) C21 0.0616(10) 0.0466(9) 0.0600(11) 0.0031(7) 0.0041(9) -0.0021(8) C22 0.0590(10) 0.0504(9) 0.0690(12) 0.0029(8) -0.0040(9) -0.0074(8) C23 0.0456(9) 0.0548(9) 0.0798(13) 0.0074(9) 0.0005(9) -0.0023(8) C24 0.0462(9) 0.0531(9) 0.0690(12) 0.0012(9) 0.0077(8) 0.0024(7) C25 0.0987(18) 0.0712(13) 0.0904(18) -0.0106(12) -0.0030(14) -0.0228(13) C26 0.0518(11) 0.0862(14) 0.1122(19) 0.0016(13) 0.0072(12) -0.0125(10) _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 1.240(3) . ? N1 C1 1.453(2) . ? N2 N3 1.127(3) . ? N4 C21 1.394(2) . ? N4 C24 1.396(2) . ? N4 C2 1.453(2) . ? O3 C7 1.362(2) . ? O3 C3 1.438(2) . ? O4 C9 1.358(3) . ? O4 C4 1.440(2) . ? O5 C1 1.425(2) . ? O5 C5 1.430(2) . ? O6 C11 1.319(2) . ? O6 C6 1.441(3) . ? O7 C7 1.158(15) . ? O7' C7 1.219(10) . ? O9 C9 1.196(3) . ? O11 C11 1.256(13) . ? O11' C11 1.195(6) . ? O21 C21 1.202(2) . ? O24 C24 1.207(2) . ? C1 C2 1.522(2) . ? C1 H1 0.9800 . ? C2 C3 1.528(2) . ? C2 H2 0.9800 . ? C3 C4 1.517(2) . ? C3 H3 0.9800 . ? C4 C5 1.518(3) . ? C4 H4 0.9800 . ? C5 C6 1.505(3) . ? C5 H5 0.9800 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.469(4) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.485(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 C12 1.477(4) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C21 C22 1.492(3) . ? C22 C23 1.319(3) . ? C22 C25 1.491(3) . ? C23 C24 1.494(3) . ? C23 C26 1.499(3) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 C1 114.07(16) . . ? N3 N2 N1 171.6(2) . . ? C21 N4 C24 109.23(14) . . ? C21 N4 C2 123.10(14) . . ? C24 N4 C2 127.35(14) . . ? C7 O3 C3 117.72(15) . . ? C9 O4 C4 117.76(16) . . ? C1 O5 C5 112.14(12) . . ? C11 O6 C6 117.72(17) . . ? O5 C1 N1 107.21(14) . . ? O5 C1 C2 110.04(13) . . ? N1 C1 C2 106.96(15) . . ? O5 C1 H1 110.8 . . ? N1 C1 H1 110.8 . . ? C2 C1 H1 110.8 . . ? N4 C2 C1 112.15(13) . . ? N4 C2 C3 111.98(13) . . ? C1 C2 C3 110.31(13) . . ? N4 C2 H2 107.4 . . ? C1 C2 H2 107.4 . . ? C3 C2 H2 107.4 . . ? O3 C3 C4 109.33(13) . . ? O3 C3 C2 107.98(13) . . ? C4 C3 C2 109.07(13) . . ? O3 C3 H3 110.1 . . ? C4 C3 H3 110.1 . . ? C2 C3 H3 110.1 . . ? O4 C4 C3 109.25(14) . . ? O4 C4 C5 107.32(13) . . ? C3 C4 C5 110.91(14) . . ? O4 C4 H4 109.8 . . ? C3 C4 H4 109.8 . . ? C5 C4 H4 109.8 . . ? O5 C5 C6 107.88(15) . . ? O5 C5 C4 108.06(14) . . ? C6 C5 C4 113.31(15) . . ? O5 C5 H5 109.2 . . ? C6 C5 H5 109.2 . . ? C4 C5 H5 109.2 . . ? O6 C6 C5 108.95(16) . . ? O6 C6 H6A 109.9 . . ? C5 C6 H6A 109.9 . . ? O6 C6 H6B 109.9 . . ? C5 C6 H6B 109.9 . . ? H6A C6 H6B 108.3 . . ? O7 C7 O3 123.8(8) . . ? O7' C7 O3 119.4(6) . . ? O7 C7 C8 122.8(9) . . ? O7' C7 C8 128.1(5) . . ? O3 C7 C8 111.1(2) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? O9 C9 O4 122.8(2) . . ? O9 C9 C10 127.4(3) . . ? O4 C9 C10 109.8(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O11' C11 O6 120.8(6) . . ? O11 C11 O6 118.8(9) . . ? O11' C11 C12 123.4(4) . . ? O11 C11 C12 122.1(4) . . ? O6 C11 C12 112.7(2) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? O21 C21 N4 125.17(16) . . ? O21 C21 C22 128.00(17) . . ? N4 C21 C22 106.82(15) . . ? C23 C22 C25 131.43(19) . . ? C23 C22 C21 108.55(16) . . ? C25 C22 C21 120.02(18) . . ? C22 C23 C24 108.77(15) . . ? C22 C23 C26 129.63(19) . . ? C24 C23 C26 121.60(19) . . ? O24 C24 N4 124.89(16) . . ? O24 C24 C23 128.59(17) . . ? N4 C24 C23 106.51(15) . . ? C22 C25 H25A 109.5 . . ? C22 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C22 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C5 O5 C1 N1 -179.14(15) . . . . ? C5 O5 C1 C2 -63.16(17) . . . . ? N2 N1 C1 O5 -66.47(19) . . . . ? N2 N1 C1 C2 175.53(15) . . . . ? C21 N4 C2 C1 108.32(18) . . . . ? C24 N4 C2 C1 -64.4(2) . . . . ? C21 N4 C2 C3 -127.04(17) . . . . ? C24 N4 C2 C3 60.2(2) . . . . ? O5 C1 C2 N4 -178.32(13) . . . . ? N1 C1 C2 N4 -62.19(17) . . . . ? O5 C1 C2 C3 56.12(17) . . . . ? N1 C1 C2 C3 172.25(13) . . . . ? C7 O3 C3 C4 106.83(18) . . . . ? C7 O3 C3 C2 -134.62(16) . . . . ? N4 C2 C3 O3 63.38(17) . . . . ? C1 C2 C3 O3 -170.96(12) . . . . ? N4 C2 C3 C4 -177.90(14) . . . . ? C1 C2 C3 C4 -52.24(17) . . . . ? C9 O4 C4 C3 114.86(19) . . . . ? C9 O4 C4 C5 -124.81(18) . . . . ? O3 C3 C4 O4 -69.43(17) . . . . ? C2 C3 C4 O4 172.70(13) . . . . ? O3 C3 C4 C5 172.47(13) . . . . ? C2 C3 C4 C5 54.60(18) . . . . ? C1 O5 C5 C6 -173.03(15) . . . . ? C1 O5 C5 C4 64.10(18) . . . . ? O4 C4 C5 O5 -178.78(13) . . . . ? C3 C4 C5 O5 -59.52(18) . . . . ? O4 C4 C5 C6 61.73(19) . . . . ? C3 C4 C5 C6 -179.01(15) . . . . ? C11 O6 C6 C5 -146.80(18) . . . . ? O5 C5 C6 O6 -67.52(19) . . . . ? C4 C5 C6 O6 52.1(2) . . . . ? C3 O3 C7 O7 21(2) . . . . ? C3 O3 C7 O7' -8.2(12) . . . . ? C3 O3 C7 C8 -176.19(19) . . . . ? C4 O4 C9 O9 -6.6(4) . . . . ? C4 O4 C9 C10 173.3(2) . . . . ? C6 O6 C11 O11' -20.2(11) . . . . ? C6 O6 C11 O11 26.1(19) . . . . ? C6 O6 C11 C12 178.61(19) . . . . ? C24 N4 C21 O21 178.00(18) . . . . ? C2 N4 C21 O21 4.1(3) . . . . ? C24 N4 C21 C22 -2.26(19) . . . . ? C2 N4 C21 C22 -176.14(15) . . . . ? O21 C21 C22 C23 179.87(19) . . . . ? N4 C21 C22 C23 0.1(2) . . . . ? O21 C21 C22 C25 -0.1(3) . . . . ? N4 C21 C22 C25 -179.87(19) . . . . ? C25 C22 C23 C24 -178.1(2) . . . . ? C21 C22 C23 C24 1.9(2) . . . . ? C25 C22 C23 C26 2.0(4) . . . . ? C21 C22 C23 C26 -178.1(2) . . . . ? C21 N4 C24 O24 -175.30(18) . . . . ? C2 N4 C24 O24 -1.8(3) . . . . ? C21 N4 C24 C23 3.34(19) . . . . ? C2 N4 C24 C23 176.89(15) . . . . ? C22 C23 C24 O24 175.30(19) . . . . ? C26 C23 C24 O24 -4.8(3) . . . . ? C22 C23 C24 N4 -3.3(2) . . . . ? C26 C23 C24 N4 176.67(18) . . . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 69.77 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.119 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.033 _chemical_compound_source synthesized