# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_name 'Hai Xia Ge' 'Jian Zhang' 'Ying Dong' 'Kai Cui' 'Bo-Yang Yu' _publ_contact_author_email wilson1978@163.com data_b _database_code_depnum_ccdc_archive 'CCDC 851213' #TrackingRef '- B.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H32 N O11' _chemical_formula_weight 522.52 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 0.0016 '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 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.1710(12) _cell_length_b 10.688(2) _cell_length_c 18.481(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.15(3) _cell_angle_gamma 90.00 _cell_volume 1218.9(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.424 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 554 _exptl_absorpt_coefficient_mu 0.112 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9671 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius cad4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 1 _diffrn_reflns_number 2605 _diffrn_reflns_av_R_equivalents 0.0697 _diffrn_reflns_av_sigmaI/netI 0.0572 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.10 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2375 _reflns_number_gt 1622 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CAD4 EXPRESS(Enraf-Nonius,1994)' _computing_cell_refinement 'CAD4 EXPRESS' _computing_data_reduction 'XCAD4(Harms & Wocadlo,1995)' _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^)+(0.1000P)^2^+0.5000P] 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_number_reflns 2375 _refine_ls_number_parameters 334 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0963 _refine_ls_R_factor_gt 0.0672 _refine_ls_wR_factor_ref 0.1835 _refine_ls_wR_factor_gt 0.1648 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _refine_ls_shift/su_max 0.000 _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 N N 0.7733(8) 0.6801(5) 0.8161(3) 0.0398(12) Uani 1 1 d . . . O1 O 1.4806(8) 0.6704(5) 1.0528(3) 0.0599(14) Uani 1 1 d . . . C1 C 1.3211(11) 0.7083(7) 1.0046(4) 0.0457(16) Uani 1 1 d . . . O2 O 1.5080(9) 0.8826(5) 1.0304(3) 0.0647(15) Uani 1 1 d . . . C2 C 1.6020(12) 0.7790(8) 1.0655(4) 0.059(2) Uani 1 1 d . . . H2A H 1.7278 0.7822 1.0933 0.071 Uiso 1 1 calc R . . O3 O 0.3247(8) 0.2141(5) 0.6995(3) 0.0653(15) Uani 1 1 d . . . C3 C 1.3387(11) 0.8331(8) 0.9908(4) 0.0507(18) Uani 1 1 d . . . O4 O 0.2876(7) 0.4579(4) 0.7119(2) 0.0420(11) Uani 1 1 d . . . C4 C 1.2031(11) 0.8948(7) 0.9458(4) 0.0493(17) Uani 1 1 d . . . H4A H 1.2147 0.9808 0.9392 0.059 Uiso 1 1 calc R . . O5 O 0.3654(6) 0.5919(4) 0.6202(2) 0.0399(10) Uani 1 1 d . . . C5 C 1.0417(10) 0.8240(7) 0.9086(3) 0.0412(15) Uani 1 1 d . . . C6 C 0.8951(12) 0.8878(7) 0.8552(4) 0.0501(17) Uani 1 1 d . . . H6A H 0.9771 0.9086 0.8121 0.060 Uiso 1 1 calc R . . H6B H 0.8423 0.9653 0.8760 0.060 Uiso 1 1 calc R . . O6 O 0.1573(13) 0.6300(6) 0.4364(3) 0.099(3) Uani 1 1 d . . . H6C H 0.0396 0.6329 0.4125 0.118 Uiso 1 1 d R . . C7 C 0.7038(11) 0.8064(6) 0.8342(4) 0.0466(17) Uani 1 1 d . . . H7A H 0.6022 0.8031 0.8741 0.056 Uiso 1 1 calc R . . H7B H 0.6300 0.8432 0.7930 0.056 Uiso 1 1 calc R . . O7 O -0.1836(10) 0.4993(8) 0.5095(4) 0.117(3) Uani 1 1 d . . . H7C H -0.1900 0.5166 0.4646 0.140 Uiso 1 1 d R . . C8 C 0.5833(11) 0.6117(6) 0.7870(4) 0.0463(16) Uani 1 1 d . . . H8A H 0.5452 0.6465 0.7402 0.056 Uiso 1 1 calc R . . H8B H 0.4612 0.6245 0.8191 0.056 Uiso 1 1 calc R . . O8 O -0.0374(9) 0.3430(6) 0.6236(3) 0.0792(19) Uani 1 1 d . . . H8C H 0.0524 0.2999 0.6449 0.119 Uiso 1 1 calc R . . C9 C 0.6224(9) 0.4728(6) 0.7787(3) 0.0367(14) Uani 1 1 d . . . O9 O 0.4035(9) 0.8343(5) 0.5717(3) 0.0743(16) Uani 1 1 d . . . H9A H 0.4775 0.9004 0.5652 0.089 Uiso 1 1 d R . . C10 C 0.4752(12) 0.4030(7) 0.7410(3) 0.0452(17) Uani 1 1 d . . . C11 C 0.4924(11) 0.2722(7) 0.7348(3) 0.0451(16) Uani 1 1 d . . . C12 C 0.6773(11) 0.2166(7) 0.7647(4) 0.0495(17) Uani 1 1 d . . . H12A H 0.7020 0.1315 0.7584 0.059 Uiso 1 1 calc R . . C13 C 0.8211(11) 0.2871(7) 0.8030(4) 0.0462(17) Uani 1 1 d . . . H13A H 0.9393 0.2476 0.8244 0.055 Uiso 1 1 calc R . . C14 C 0.7992(10) 0.4154(6) 0.8116(4) 0.0413(15) Uani 1 1 d . . . C15 C 0.9536(10) 0.4919(6) 0.8576(3) 0.0425(15) Uani 1 1 d . . . H15A H 0.9922 0.4441 0.9003 0.051 Uiso 1 1 calc R . . H15B H 1.0853 0.5069 0.8304 0.051 Uiso 1 1 calc R . . C16 C 0.8605(10) 0.6151(6) 0.8807(3) 0.0399(15) Uani 1 1 d . . . H16A H 0.7399 0.5987 0.9138 0.048 Uiso 1 1 calc R . . C17 C 1.0266(11) 0.6951(6) 0.9203(3) 0.0436(16) Uani 1 1 d . . . C18 C 1.1702(11) 0.6365(8) 0.9707(4) 0.0504(17) Uani 1 1 d . . . H18A H 1.1606 0.5512 0.9801 0.060 Uiso 1 1 calc R . . C19 C 0.3207(16) 0.0818(9) 0.6980(7) 0.106(4) Uani 1 1 d . . . H19A H 0.1958 0.0541 0.6714 0.158 Uiso 1 1 calc R . . H19B H 0.3141 0.0502 0.7465 0.158 Uiso 1 1 calc R . . H19C H 0.4496 0.0514 0.6749 0.158 Uiso 1 1 calc R . . C20 C 0.2818(10) 0.4720(6) 0.6354(3) 0.0388(14) Uani 1 1 d . . . H20A H 0.3690 0.4070 0.6119 0.047 Uiso 1 1 calc R . . C21 C 0.3713(11) 0.6151(7) 0.5430(4) 0.0516(18) Uani 1 1 d . . . H21A H 0.4488 0.5459 0.5198 0.062 Uiso 1 1 calc R . . C22 C 0.1432(14) 0.6179(8) 0.5136(4) 0.064(2) Uani 1 1 d . . . H22A H 0.0627 0.6884 0.5342 0.077 Uiso 1 1 calc R . . C23 C 0.0317(10) 0.4963(7) 0.5308(4) 0.0491(17) Uani 1 1 d . . . H23A H 0.1040 0.4298 0.5034 0.059 Uiso 1 1 calc R . . C24 C 0.0506(10) 0.4651(7) 0.6108(4) 0.0512(18) Uani 1 1 d . . . H24A H -0.0341 0.5262 0.6384 0.061 Uiso 1 1 calc R . . C25 C 0.5004(15) 0.7334(8) 0.5319(5) 0.073(2) Uani 1 1 d . . . H25A H 0.6482 0.7207 0.5483 0.088 Uiso 1 1 calc R . . H25B H 0.5041 0.7541 0.4808 0.088 Uiso 1 1 calc R . . OW1 O 0.7529(9) 0.9231(7) 0.6482(3) 0.0800(18) Uani 1 1 d . . . HW1A H 0.8124 0.8586 0.6302 0.096 Uiso 1 1 d R . . HW1B H 0.7687 0.9236 0.6939 0.096 Uiso 1 1 d R . . OW2 O 1.0645(10) 0.7666(7) 0.7011(3) 0.089(2) Uani 1 1 d . . . HW2A H 1.0817 0.7362 0.7432 0.107 Uiso 1 1 d R . . HW2B H 1.1894 0.7854 0.6852 0.107 Uiso 1 1 d 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 N 0.041(3) 0.034(3) 0.045(3) -0.005(3) -0.001(2) 0.002(2) O1 0.058(3) 0.055(3) 0.066(3) -0.011(3) -0.028(3) 0.003(3) C1 0.047(4) 0.042(4) 0.048(4) -0.002(3) -0.002(3) 0.001(3) O2 0.066(3) 0.059(3) 0.070(3) -0.012(3) -0.014(3) -0.011(3) C2 0.052(4) 0.064(5) 0.060(5) -0.016(4) -0.014(3) -0.008(4) O3 0.058(3) 0.037(3) 0.101(4) -0.011(3) -0.021(3) -0.008(2) C3 0.046(4) 0.055(5) 0.050(4) -0.018(4) 0.003(3) -0.006(4) O4 0.047(2) 0.043(3) 0.036(2) -0.002(2) -0.0007(18) -0.002(2) C4 0.056(4) 0.038(4) 0.054(4) -0.002(3) -0.001(3) -0.002(3) O5 0.035(2) 0.041(3) 0.043(2) 0.005(2) -0.0015(18) -0.004(2) C5 0.045(3) 0.036(4) 0.043(4) -0.002(3) 0.005(3) 0.000(3) C6 0.058(4) 0.044(4) 0.049(4) 0.005(3) -0.005(3) 0.000(3) O6 0.198(8) 0.050(3) 0.048(3) -0.006(3) -0.038(4) 0.028(4) C7 0.051(4) 0.038(4) 0.051(4) 0.000(3) -0.001(3) 0.003(3) O7 0.066(4) 0.129(6) 0.155(6) -0.076(6) -0.070(4) 0.054(4) C8 0.049(4) 0.037(4) 0.052(4) 0.001(3) -0.011(3) 0.000(3) O8 0.075(3) 0.088(5) 0.074(4) -0.015(3) -0.009(3) -0.047(4) C9 0.037(3) 0.031(3) 0.042(3) -0.002(3) 0.000(3) -0.001(3) O9 0.068(3) 0.036(3) 0.120(5) 0.016(3) -0.014(3) -0.002(3) C10 0.065(4) 0.039(4) 0.031(3) 0.011(3) -0.001(3) -0.004(3) C11 0.056(4) 0.041(4) 0.038(4) 0.000(3) 0.005(3) -0.002(3) C12 0.051(4) 0.032(3) 0.066(5) -0.005(3) -0.006(3) 0.006(3) C13 0.049(4) 0.036(4) 0.054(4) 0.002(3) -0.005(3) 0.000(3) C14 0.043(4) 0.036(4) 0.045(4) -0.001(3) 0.001(3) -0.004(3) C15 0.044(3) 0.038(4) 0.045(4) 0.002(3) -0.006(3) -0.007(3) C16 0.036(3) 0.041(4) 0.042(3) -0.001(3) 0.005(3) -0.006(3) C17 0.051(4) 0.036(4) 0.043(4) 0.001(3) 0.001(3) 0.000(3) C18 0.059(4) 0.048(4) 0.045(4) -0.007(3) -0.007(3) 0.001(3) C19 0.081(7) 0.043(5) 0.192(12) -0.026(7) -0.030(7) -0.010(5) C20 0.040(3) 0.032(3) 0.044(3) -0.002(3) 0.000(3) 0.000(3) C21 0.052(4) 0.042(4) 0.061(4) 0.006(3) 0.006(3) 0.009(3) C22 0.089(6) 0.046(5) 0.058(5) -0.016(4) -0.028(4) 0.019(4) C23 0.041(3) 0.047(4) 0.059(4) -0.017(3) -0.020(3) 0.012(3) C24 0.035(3) 0.050(4) 0.068(4) -0.023(4) -0.002(3) -0.007(3) C25 0.081(5) 0.049(5) 0.090(6) 0.006(5) 0.030(5) 0.005(4) OW1 0.071(3) 0.086(5) 0.083(4) 0.010(3) -0.003(3) -0.003(3) OW2 0.104(4) 0.078(4) 0.085(4) 0.014(4) 0.031(3) 0.031(4) _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 N C7 1.456(9) . ? N C16 1.482(8) . ? N C8 1.481(8) . ? O1 C1 1.387(8) . ? O1 C2 1.401(9) . ? C1 C18 1.359(10) . ? C1 C3 1.361(10) . ? O2 C3 1.379(8) . ? O2 C2 1.407(10) . ? C2 H2A 0.9300 . ? O3 C11 1.371(8) . ? O3 C19 1.414(11) . ? C3 C4 1.351(10) . ? O4 C10 1.403(8) . ? O4 C20 1.421(7) . ? C4 C5 1.426(9) . ? C4 H4A 0.9300 . ? O5 C20 1.410(8) . ? O5 C21 1.450(8) . ? C5 C17 1.397(10) . ? C5 C6 1.502(9) . ? C6 C7 1.516(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? O6 C22 1.435(10) . ? O6 H6C 0.8500 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? O7 C23 1.385(8) . ? O7 H7C 0.8500 . ? C8 C9 1.512(9) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? O8 C24 1.433(10) . ? O8 H8C 0.8200 . ? C9 C10 1.365(9) . ? C9 C14 1.390(9) . ? O9 C25 1.437(10) . ? O9 H9A 0.8500 . ? C10 C11 1.406(10) . ? C11 C12 1.399(9) . ? C12 C13 1.362(10) . ? C12 H12A 0.9300 . ? C13 C14 1.387(10) . ? C13 H13A 0.9300 . ? C14 C15 1.515(9) . ? C15 C16 1.499(9) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.521(9) . ? C16 H16A 0.9800 . ? C17 C18 1.428(10) . ? C18 H18A 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 C24 1.498(8) . ? C20 H20A 0.9800 . ? C21 C25 1.508(11) . ? C21 C22 1.507(11) . ? C21 H21A 0.9800 . ? C22 C23 1.506(12) . ? C22 H22A 0.9800 . ? C23 C24 1.521(10) . ? C23 H23A 0.9800 . ? C24 H24A 0.9800 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? OW1 HW1A 0.8498 . ? OW1 HW1B 0.8499 . ? OW2 HW2A 0.8499 . ? OW2 HW2B 0.8498 . ? 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 C7 N C16 110.8(5) . . ? C7 N C8 107.9(5) . . ? C16 N C8 110.3(5) . . ? C1 O1 C2 104.1(6) . . ? C18 C1 C3 121.5(7) . . ? C18 C1 O1 128.0(7) . . ? C3 C1 O1 110.5(6) . . ? C3 O2 C2 104.7(6) . . ? O1 C2 O2 110.8(5) . . ? O1 C2 H2A 124.6 . . ? O2 C2 H2A 124.6 . . ? C11 O3 C19 118.4(7) . . ? C4 C3 C1 122.9(7) . . ? C4 C3 O2 127.3(7) . . ? C1 C3 O2 109.7(7) . . ? C10 O4 C20 116.3(5) . . ? C3 C4 C5 117.9(7) . . ? C3 C4 H4A 121.0 . . ? C5 C4 H4A 121.0 . . ? C20 O5 C21 111.2(5) . . ? C17 C5 C4 119.7(6) . . ? C17 C5 C6 120.6(6) . . ? C4 C5 C6 119.6(6) . . ? C5 C6 C7 112.0(6) . . ? C5 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? C5 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? C22 O6 H6C 117.8 . . ? N C7 C6 111.2(5) . . ? N C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? N C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? C23 O7 H7C 108.9 . . ? N C8 C9 113.3(5) . . ? N C8 H8A 108.9 . . ? C9 C8 H8A 108.9 . . ? N C8 H8B 108.9 . . ? C9 C8 H8B 108.9 . . ? H8A C8 H8B 107.7 . . ? C24 O8 H8C 109.5 . . ? C10 C9 C14 120.2(6) . . ? C10 C9 C8 118.8(6) . . ? C14 C9 C8 120.9(6) . . ? C25 O9 H9A 109.1 . . ? C9 C10 O4 120.9(6) . . ? C9 C10 C11 122.3(7) . . ? O4 C10 C11 116.6(6) . . ? O3 C11 C12 127.5(6) . . ? O3 C11 C10 115.6(6) . . ? C12 C11 C10 116.9(7) . . ? C13 C12 C11 120.0(6) . . ? C13 C12 H12A 120.0 . . ? C11 C12 H12A 120.0 . . ? C12 C13 C14 122.9(7) . . ? C12 C13 H13A 118.6 . . ? C14 C13 H13A 118.6 . . ? C13 C14 C9 117.6(6) . . ? C13 C14 C15 122.4(6) . . ? C9 C14 C15 119.9(6) . . ? C16 C15 C14 113.1(5) . . ? C16 C15 H15A 109.0 . . ? C14 C15 H15A 109.0 . . ? C16 C15 H15B 109.0 . . ? C14 C15 H15B 109.0 . . ? H15A C15 H15B 107.8 . . ? N C16 C15 108.7(5) . . ? N C16 C17 111.6(5) . . ? C15 C16 C17 111.9(5) . . ? N C16 H16A 108.2 . . ? C15 C16 H16A 108.2 . . ? C17 C16 H16A 108.2 . . ? C5 C17 C18 119.5(7) . . ? C5 C17 C16 121.6(6) . . ? C18 C17 C16 118.9(6) . . ? C1 C18 C17 118.4(7) . . ? C1 C18 H18A 120.8 . . ? C17 C18 H18A 120.8 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O5 C20 O4 106.6(5) . . ? O5 C20 C24 109.4(5) . . ? O4 C20 C24 108.6(5) . . ? O5 C20 H20A 110.7 . . ? O4 C20 H20A 110.7 . . ? C24 C20 H20A 110.7 . . ? O5 C21 C25 107.0(7) . . ? O5 C21 C22 109.4(6) . . ? C25 C21 C22 115.3(7) . . ? O5 C21 H21A 108.3 . . ? C25 C21 H21A 108.3 . . ? C22 C21 H21A 108.3 . . ? O6 C22 C23 108.5(6) . . ? O6 C22 C21 107.5(8) . . ? C23 C22 C21 109.5(6) . . ? O6 C22 H22A 110.4 . . ? C23 C22 H22A 110.4 . . ? C21 C22 H22A 110.4 . . ? O7 C23 C22 111.0(7) . . ? O7 C23 C24 110.7(7) . . ? C22 C23 C24 111.2(6) . . ? O7 C23 H23A 107.9 . . ? C22 C23 H23A 107.9 . . ? C24 C23 H23A 107.9 . . ? O8 C24 C20 110.9(6) . . ? O8 C24 C23 109.4(6) . . ? C20 C24 C23 110.8(6) . . ? O8 C24 H24A 108.6 . . ? C20 C24 H24A 108.6 . . ? C23 C24 H24A 108.6 . . ? O9 C25 C21 109.8(6) . . ? O9 C25 H25A 109.7 . . ? C21 C25 H25A 109.7 . . ? O9 C25 H25B 109.7 . . ? C21 C25 H25B 109.7 . . ? H25A C25 H25B 108.2 . . ? HW1A OW1 HW1B 110.2 . . ? HW2A OW2 HW2B 107.3 . . ? 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 C2 O1 C1 C18 174.6(7) . . . . ? C2 O1 C1 C3 -2.2(8) . . . . ? C1 O1 C2 O2 4.7(8) . . . . ? C3 O2 C2 O1 -5.4(8) . . . . ? C18 C1 C3 C4 3.2(11) . . . . ? O1 C1 C3 C4 -179.8(6) . . . . ? C18 C1 C3 O2 -178.1(6) . . . . ? O1 C1 C3 O2 -1.1(8) . . . . ? C2 O2 C3 C4 -177.5(7) . . . . ? C2 O2 C3 C1 3.9(8) . . . . ? C1 C3 C4 C5 -3.1(10) . . . . ? O2 C3 C4 C5 178.4(6) . . . . ? C3 C4 C5 C17 0.8(9) . . . . ? C3 C4 C5 C6 -176.9(6) . . . . ? C17 C5 C6 C7 15.4(9) . . . . ? C4 C5 C6 C7 -166.9(6) . . . . ? C16 N C7 C6 66.6(7) . . . . ? C8 N C7 C6 -172.5(5) . . . . ? C5 C6 C7 N -47.7(8) . . . . ? C7 N C8 C9 -169.5(6) . . . . ? C16 N C8 C9 -48.3(7) . . . . ? N C8 C9 C10 -168.7(5) . . . . ? N C8 C9 C14 14.3(9) . . . . ? C14 C9 C10 O4 175.3(6) . . . . ? C8 C9 C10 O4 -1.7(9) . . . . ? C14 C9 C10 C11 1.2(10) . . . . ? C8 C9 C10 C11 -175.8(7) . . . . ? C20 O4 C10 C9 108.0(7) . . . . ? C20 O4 C10 C11 -77.6(7) . . . . ? C19 O3 C11 C12 6.7(12) . . . . ? C19 O3 C11 C10 -173.6(9) . . . . ? C9 C10 C11 O3 175.6(6) . . . . ? O4 C10 C11 O3 1.3(9) . . . . ? C9 C10 C11 C12 -4.6(10) . . . . ? O4 C10 C11 C12 -179.0(5) . . . . ? O3 C11 C12 C13 -174.9(7) . . . . ? C10 C11 C12 C13 5.4(10) . . . . ? C11 C12 C13 C14 -3.0(11) . . . . ? C12 C13 C14 C9 -0.6(11) . . . . ? C12 C13 C14 C15 176.7(6) . . . . ? C10 C9 C14 C13 1.5(10) . . . . ? C8 C9 C14 C13 178.4(6) . . . . ? C10 C9 C14 C15 -175.9(6) . . . . ? C8 C9 C14 C15 1.1(10) . . . . ? C13 C14 C15 C16 -159.7(7) . . . . ? C9 C14 C15 C16 17.5(8) . . . . ? C7 N C16 C15 -173.3(5) . . . . ? C8 N C16 C15 67.2(6) . . . . ? C7 N C16 C17 -49.5(7) . . . . ? C8 N C16 C17 -169.0(5) . . . . ? C14 C15 C16 N -50.7(7) . . . . ? C14 C15 C16 C17 -174.3(5) . . . . ? C4 C5 C17 C18 1.4(9) . . . . ? C6 C5 C17 C18 179.1(6) . . . . ? C4 C5 C17 C16 -178.6(5) . . . . ? C6 C5 C17 C16 -0.9(10) . . . . ? N C16 C17 C5 17.4(8) . . . . ? C15 C16 C17 C5 139.4(6) . . . . ? N C16 C17 C18 -162.6(5) . . . . ? C15 C16 C17 C18 -40.5(8) . . . . ? C3 C1 C18 C17 -0.8(10) . . . . ? O1 C1 C18 C17 -177.3(6) . . . . ? C5 C17 C18 C1 -1.4(9) . . . . ? C16 C17 C18 C1 178.5(6) . . . . ? C21 O5 C20 O4 178.7(5) . . . . ? C21 O5 C20 C24 -64.1(6) . . . . ? C10 O4 C20 O5 -91.9(6) . . . . ? C10 O4 C20 C24 150.3(6) . . . . ? C20 O5 C21 C25 -169.5(5) . . . . ? C20 O5 C21 C22 65.0(7) . . . . ? O5 C21 C22 O6 -175.0(6) . . . . ? C25 C21 C22 O6 64.4(8) . . . . ? O5 C21 C22 C23 -57.3(8) . . . . ? C25 C21 C22 C23 -177.9(7) . . . . ? O6 C22 C23 O7 -67.6(8) . . . . ? C21 C22 C23 O7 175.4(6) . . . . ? O6 C22 C23 C24 168.8(6) . . . . ? C21 C22 C23 C24 51.7(8) . . . . ? O5 C20 C24 O8 178.3(5) . . . . ? O4 C20 C24 O8 -65.7(7) . . . . ? O5 C20 C24 C23 56.7(7) . . . . ? O4 C20 C24 C23 172.6(5) . . . . ? O7 C23 C24 O8 62.1(8) . . . . ? C22 C23 C24 O8 -174.0(6) . . . . ? O7 C23 C24 C20 -175.4(6) . . . . ? C22 C23 C24 C20 -51.5(8) . . . . ? O5 C21 C25 O9 -57.3(8) . . . . ? C22 C21 C25 O9 64.6(10) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.288 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.055