data_307 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H23 N O10' _chemical_formula_weight 557.49 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 15.307(3) _cell_length_b 7.9472(16) _cell_length_c 24.715(5) _cell_angle_alpha 90.00 _cell_angle_beta 97.18(3) _cell_angle_gamma 90.00 _cell_volume 2983.0(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.241 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.795 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.8082 _exptl_absorpt_correction_T_max 0.9614 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11429 _diffrn_reflns_av_R_equivalents 0.0912 _diffrn_reflns_av_sigmaI/netI 0.1647 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 4.91 _diffrn_reflns_theta_max 66.98 _reflns_number_total 4797 _reflns_number_gt 2116 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^+0.0000P] 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 0.045(6) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4797 _refine_ls_number_parameters 398 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2947 _refine_ls_R_factor_gt 0.2224 _refine_ls_wR_factor_ref 0.5021 _refine_ls_wR_factor_gt 0.4653 _refine_ls_goodness_of_fit_ref 1.848 _refine_ls_restrained_S_all 1.848 _refine_ls_shift/su_max 2.950 _refine_ls_shift/su_mean 0.224 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 O7 O 0.8640(5) 0.3151(10) 0.5263(3) 0.089(2) Uani 1 1 d . . . O8 O 0.8841(5) 0.5447(10) 0.3185(3) 0.105(3) Uani 1 1 d . . . O1' O 0.6270(13) -0.277(3) 0.6261(11) 0.218(12) Uani 0.50 1 d P . . O2' O 1.2396(12) 0.356(2) 0.3719(13) 0.225(15) Uani 0.50 1 d P . . O9 O 1.0166(5) 0.3720(10) 0.3696(3) 0.105(3) Uani 1 1 d . . . H9B H 1.0546 0.3192 0.3889 0.157 Uiso 1 1 calc R . . O10 O 1.0891(5) 0.2187(10) 0.4563(3) 0.102(2) Uani 1 1 d . . . O11 O 1.1528(5) 0.0632(10) 0.5448(3) 0.099(2) Uani 1 1 d . . . H11A H 1.1528 0.0999 0.5138 0.148 Uiso 1 1 calc R . . O12 O 1.1338(5) -0.0256(10) 0.6485(3) 0.101(3) Uani 1 1 d . . . H12A H 1.1808 0.0229 0.6476 0.151 Uiso 1 1 calc R . . O5 O 0.7437(4) 0.0894(9) 0.5502(2) 0.093(2) Uani 1 1 d . . . H5A H 0.6920 0.0691 0.5391 0.140 Uiso 1 1 calc R . . O4 O 0.5804(5) 0.0613(12) 0.5529(3) 0.116(3) Uani 1 1 d . . . O3 O 0.4467(12) -0.206(3) 0.6378(13) 0.370(13) Uani 1 1 d . B . H3A H 0.4984 -0.2293 0.6359 0.555 Uiso 1 1 calc R . . O2 O 0.3172(6) 0.0273(13) 0.6725(4) 0.135(3) Uani 1 1 d . . . O1 O 0.4522(6) 0.1057(14) 0.7071(4) 0.148(4) Uani 1 1 d . . . N4 N 0.5201(7) 0.0840(13) 0.6298(3) 0.110(3) Uani 1 1 d . . . C11 C 0.9476(7) 0.3972(13) 0.3967(4) 0.079(3) Uani 1 1 d . . . C10 C 0.8780(8) 0.4932(15) 0.3704(4) 0.092(3) Uani 1 1 d . . . C9 C 0.8026(9) 0.5157(17) 0.3968(4) 0.110(4) Uani 1 1 d . . . H9A H 0.7545 0.5742 0.3793 0.132 Uiso 1 1 calc R . . C8 C 0.7993(8) 0.4525(18) 0.4479(4) 0.110(4) Uani 1 1 d . . . H8A H 0.7481 0.4632 0.4642 0.132 Uiso 1 1 calc R . . C8' C 0.8703(8) 0.3744(14) 0.4748(4) 0.091(3) Uani 1 1 d . . . C7'' C 0.9317(7) 0.2247(14) 0.5543(4) 0.080(3) Uani 1 1 d . . . C7' C 0.9198(6) 0.1616(14) 0.6073(3) 0.074(3) Uani 1 1 d . B . C14' C 0.9902(8) 0.0989(14) 0.6379(4) 0.085(3) Uani 1 1 d . . . C14 C 1.0683(7) 0.0611(14) 0.6177(4) 0.084(3) Uani 1 1 d . . . C13 C 1.0772(7) 0.1029(14) 0.5630(4) 0.085(3) Uani 1 1 d . . . C12' C 1.0108(6) 0.1862(13) 0.5321(4) 0.071(3) Uani 1 1 d . . . C12 C 1.0186(7) 0.2472(14) 0.4776(4) 0.084(3) Uani 1 1 d . . . C11' C 0.9445(7) 0.3423(16) 0.4495(4) 0.090(3) Uani 1 1 d . . . C15 C 0.9840(7) 0.0734(18) 0.6992(4) 0.104(4) Uani 1 1 d . . . H15A H 0.9557 -0.0332 0.7051 0.124 Uiso 1 1 calc R . . H15B H 1.0423 0.0729 0.7196 0.124 Uiso 1 1 calc R . . C16 C 0.9305(8) 0.2167(16) 0.7176(4) 0.099(4) Uani 1 1 d . . . H16A H 0.9591 0.3226 0.7114 0.119 Uiso 1 1 calc R . . H16B H 0.9271 0.2066 0.7564 0.119 Uiso 1 1 calc R . . C16' C 0.8419(7) 0.2157(12) 0.6880(4) 0.080(3) Uani 1 1 d . B . C17 C 0.7691(7) 0.2205(13) 0.7147(4) 0.085(3) Uani 1 1 d . . . H17A H 0.7748 0.2486 0.7515 0.102 Uiso 1 1 calc R . . C17' C 0.6838(8) 0.1825(14) 0.6864(4) 0.087(3) Uani 1 1 d . B . C18 C 0.6013(8) 0.1878(19) 0.7146(5) 0.116(4) Uani 1 1 d . . . H18A H 0.6125 0.1221 0.7479 0.139 Uiso 1 1 calc R A 1 H18B H 0.5924 0.3033 0.7254 0.139 Uiso 1 1 calc R A 1 C2 C 0.3936(11) 0.0670(19) 0.6647(6) 0.122(5) Uani 1 1 d . B . C3 C 0.4283(7) 0.0583(18) 0.6127(5) 0.089(3) Uani 1 1 d . B . C5 C 0.5955(9) 0.0984(14) 0.6019(4) 0.092(3) Uani 1 1 d . B . C5' C 0.6748(7) 0.1379(13) 0.6296(4) 0.081(3) Uani 1 1 d . . . C6 C 0.7506(8) 0.1408(14) 0.6039(4) 0.085(3) Uani 1 1 d . B . C6' C 0.8349(7) 0.1809(15) 0.6311(4) 0.085(3) Uani 1 1 d . . . C23 C 0.8124(9) 0.6338(16) 0.2902(4) 0.114(4) Uani 1 1 d . . . H23A H 0.8249 0.6592 0.2540 0.170 Uiso 1 1 calc R . . H23B H 0.8035 0.7366 0.3091 0.170 Uiso 1 1 calc R . . H23C H 0.7602 0.5661 0.2882 0.170 Uiso 1 1 calc R . . C22 C 0.3864(12) 0.193(5) 0.5768(10) 0.36(2) Uani 1 1 d . . . H22A H 0.3961 0.3000 0.5946 0.544 Uiso 1 1 calc R B . H22B H 0.3242 0.1723 0.5694 0.544 Uiso 1 1 calc R . . H22C H 0.4116 0.1941 0.5431 0.544 Uiso 1 1 calc R . . C21 C 0.4113(13) -0.107(3) 0.5895(7) 0.158(8) Uani 1 1 d . . . H21A H 0.4434 -0.1270 0.5587 0.190 Uiso 1 1 calc R B . H21B H 0.3490 -0.1271 0.5790 0.190 Uiso 1 1 calc R . . C19 C 0.5319(18) 0.137(7) 0.6894(9) 0.57(4) Uani 1 1 d . B 1 C20 C 0.5081(18) 0.401(4) 0.6644(16) 0.38(2) Uani 1 1 d . B 1 H20A H 0.5048 0.4696 0.6961 0.563 Uiso 1 1 calc R B 1 H20B H 0.4536 0.4089 0.6406 0.563 Uiso 1 1 calc R B 1 H20C H 0.5554 0.4399 0.6455 0.563 Uiso 1 1 calc R B 1 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 O7 0.087(5) 0.112(6) 0.070(4) 0.008(4) 0.022(4) 0.008(4) O8 0.122(7) 0.119(7) 0.078(4) 0.010(4) 0.031(4) 0.009(5) O1' 0.133(17) 0.14(2) 0.34(3) 0.066(17) -0.124(19) -0.021(12) O2' 0.096(14) 0.107(16) 0.50(5) 0.10(2) 0.13(2) 0.027(10) O9 0.076(5) 0.158(7) 0.088(4) -0.002(4) 0.038(4) -0.001(4) O10 0.101(5) 0.123(7) 0.090(4) 0.001(4) 0.051(4) 0.014(4) O11 0.090(5) 0.115(6) 0.098(5) 0.007(4) 0.036(4) 0.011(4) O12 0.072(5) 0.134(7) 0.094(5) 0.020(4) 0.006(4) -0.001(4) O5 0.087(5) 0.132(7) 0.063(4) -0.014(4) 0.021(3) -0.004(4) O4 0.100(6) 0.160(8) 0.089(5) -0.015(5) 0.019(4) 0.003(5) O3 0.182(17) 0.28(2) 0.68(4) -0.12(3) 0.16(2) -0.010(15) O2 0.089(6) 0.198(10) 0.119(6) -0.003(6) 0.025(5) 0.014(6) O1 0.112(7) 0.242(12) 0.099(6) -0.014(6) 0.049(5) -0.066(7) N4 0.092(7) 0.164(10) 0.080(5) 0.001(6) 0.034(5) -0.011(6) C11 0.090(8) 0.085(9) 0.066(5) 0.000(5) 0.024(5) -0.003(6) C10 0.103(9) 0.117(10) 0.060(5) -0.012(6) 0.024(6) -0.008(7) C9 0.129(11) 0.131(11) 0.072(6) -0.015(7) 0.026(7) 0.035(8) C8 0.088(9) 0.165(13) 0.083(7) 0.006(8) 0.033(6) 0.030(8) C8' 0.098(9) 0.106(10) 0.073(6) 0.002(6) 0.024(6) 0.022(7) C7'' 0.072(7) 0.096(9) 0.077(6) 0.001(6) 0.022(5) -0.012(5) C7' 0.062(6) 0.103(9) 0.060(5) -0.003(5) 0.020(4) 0.008(5) C14' 0.084(8) 0.099(9) 0.078(6) 0.007(6) 0.028(6) -0.022(6) C14 0.077(7) 0.089(8) 0.087(7) 0.001(6) 0.021(6) -0.009(6) C13 0.079(7) 0.099(9) 0.082(6) 0.002(6) 0.025(6) 0.006(6) C12' 0.073(6) 0.080(7) 0.060(5) -0.006(5) 0.017(5) 0.009(5) C12 0.065(7) 0.090(8) 0.100(7) -0.015(6) 0.031(5) -0.015(5) C11' 0.067(7) 0.129(10) 0.078(6) -0.013(6) 0.022(5) -0.002(6) C15 0.067(7) 0.173(13) 0.072(6) -0.002(7) 0.014(5) -0.016(7) C16 0.098(9) 0.137(12) 0.062(5) -0.019(6) 0.012(6) -0.026(7) C16' 0.093(8) 0.069(8) 0.084(6) -0.003(5) 0.033(6) -0.003(5) C17 0.081(8) 0.099(9) 0.079(6) -0.009(5) 0.029(6) -0.004(6) C17' 0.106(9) 0.089(8) 0.075(6) 0.005(5) 0.041(6) 0.010(6) C18 0.116(10) 0.139(11) 0.103(8) -0.014(8) 0.059(8) -0.002(8) C2 0.089(10) 0.162(14) 0.119(10) 0.004(9) 0.022(9) -0.003(9) C3 0.072(8) 0.102(10) 0.098(7) -0.024(7) 0.030(6) -0.015(6) C5 0.110(9) 0.106(10) 0.064(6) 0.002(6) 0.029(6) -0.008(7) C5' 0.075(7) 0.105(9) 0.064(5) 0.002(5) 0.019(5) -0.011(6) C6 0.092(8) 0.101(9) 0.069(6) -0.004(5) 0.032(6) 0.016(6) C6' 0.079(7) 0.118(9) 0.062(5) 0.021(6) 0.021(5) 0.007(6) C23 0.140(11) 0.115(12) 0.088(7) 0.009(7) 0.024(8) 0.004(8) C22 0.122(14) 0.69(6) 0.30(2) 0.38(3) 0.132(15) 0.18(2) C21 0.156(16) 0.19(2) 0.139(13) 0.042(14) 0.046(11) 0.057(13) C19 0.23(2) 1.33(10) 0.173(15) -0.38(4) 0.176(16) -0.50(4) C20 0.17(2) 0.28(4) 0.64(6) 0.06(3) -0.08(3) -0.03(2) _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 O7 C8' 1.372(11) . ? O7 C7'' 1.374(12) . ? O8 C10 1.362(11) . ? O8 C23 1.415(12) . ? O9 C11 1.335(11) . ? O9 H9B 0.8200 . ? O10 C12 1.280(11) . ? O11 C13 1.330(11) . ? O11 H11A 0.8200 . ? O12 C14 1.366(11) . ? O12 H12A 0.8200 . ? O5 C6 1.381(10) . ? O5 H5A 0.8200 . ? O4 C5 1.240(11) . ? O3 C21 1.47(3) . ? O3 H3A 0.8200 . ? O2 C2 1.250(15) . ? O1 C2 1.329(15) . ? O1 C19 1.369(17) . ? N4 C5 1.420(13) . ? N4 C3 1.431(13) . ? N4 C19 1.521(17) . ? C11 C11' 1.381(13) . ? C11 C10 1.402(14) . ? C10 C9 1.406(14) . ? C9 C8 1.366(15) . ? C9 H9A 0.9300 . ? C8 C8' 1.352(14) . ? C8 H8A 0.9300 . ? C8' C11' 1.388(13) . ? C7'' C12' 1.423(12) . ? C7'' C7' 1.437(12) . ? C7' C14' 1.333(13) . ? C7' C6' 1.499(12) . ? C14' C14 1.385(13) . ? C14' C15 1.543(13) . ? C14 C13 1.416(13) . ? C13 C12' 1.363(12) . ? C12' C12 1.450(13) . ? C12 C11' 1.464(14) . ? C15 C16 1.506(16) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C16' 1.458(14) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C16' C17 1.366(12) . ? C16' C6' 1.425(12) . ? C17 C17' 1.434(14) . ? C17 H17A 0.9300 . ? C17' C5' 1.437(13) . ? C17' C18 1.518(13) . ? C18 C19 1.230(18) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C2 C3 1.451(17) . ? C3 C21 1.44(2) . ? C3 C22 1.49(2) . ? C5 C5' 1.354(14) . ? C5' C6 1.391(13) . ? C6 C6' 1.415(14) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C19 C20 2.20(6) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C8' O7 C7'' 120.7(8) . . ? C10 O8 C23 118.5(9) . . ? C11 O9 H9B 109.3 . . ? C13 O11 H11A 109.3 . . ? C14 O12 H12A 109.5 . . ? C6 O5 H5A 109.3 . . ? C21 O3 H3A 109.7 . . ? C2 O1 C19 109.4(12) . . ? C5 N4 C3 134.1(9) . . ? C5 N4 C19 116.2(10) . . ? C3 N4 C19 108.6(11) . . ? O9 C11 C11' 123.3(10) . . ? O9 C11 C10 116.9(9) . . ? C11' C11 C10 119.7(10) . . ? O8 C10 C11 117.6(10) . . ? O8 C10 C9 123.7(11) . . ? C11 C10 C9 118.4(10) . . ? C10 C9 C8 120.5(11) . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.6 . . ? C8' C8 C9 120.3(11) . . ? C8' C8 H8A 119.8 . . ? C9 C8 H8A 119.9 . . ? C8 C8' O7 118.0(10) . . ? C8 C8' C11' 121.0(10) . . ? O7 C8' C11' 120.8(10) . . ? O7 C7'' C12' 122.9(8) . . ? O7 C7'' C7' 117.9(9) . . ? C12' C7'' C7' 119.1(10) . . ? C14' C7' C7'' 117.5(9) . . ? C14' C7' C6' 119.7(8) . . ? C7'' C7' C6' 122.4(9) . . ? C7' C14' C14 123.4(10) . . ? C7' C14' C15 117.4(10) . . ? C14 C14' C15 119.2(10) . . ? O12 C14 C14' 121.0(10) . . ? O12 C14 C13 119.9(10) . . ? C14' C14 C13 118.9(10) . . ? O11 C13 C12' 123.1(9) . . ? O11 C13 C14 117.3(10) . . ? C12' C13 C14 119.6(10) . . ? C13 C12' C7'' 120.0(9) . . ? C13 C12' C12 122.6(9) . . ? C7'' C12' C12 117.3(9) . . ? O10 C12 C11' 122.6(10) . . ? O10 C12 C12' 119.6(10) . . ? C11' C12 C12' 117.7(9) . . ? C11 C11' C8' 119.6(11) . . ? C11 C11' C12 119.8(10) . . ? C8' C11' C12 120.6(10) . . ? C16 C15 C14' 107.5(10) . . ? C16 C15 H15A 110.3 . . ? C14' C15 H15A 110.2 . . ? C16 C15 H15B 110.2 . . ? C14' C15 H15B 110.1 . . ? H15A C15 H15B 108.5 . . ? C15 C16 C16' 110.5(9) . . ? C15 C16 H16A 109.6 . . ? C16' C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? C16' C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C17 C16' C6' 121.2(10) . . ? C17 C16' C16 121.4(9) . . ? C6' C16' C16 116.6(9) . . ? C16' C17 C17' 120.4(9) . . ? C16' C17 H17A 119.8 . . ? C17' C17 H17A 119.7 . . ? C17 C17' C5' 120.0(9) . . ? C17 C17' C18 121.9(9) . . ? C5' C17' C18 118.1(10) . . ? C19 C18 C17' 118.3(13) . . ? C19 C18 H18A 104.6 . . ? C17' C18 H18A 107.5 . . ? C19 C18 H18B 111.5 . . ? C17' C18 H18B 107.4 . . ? H18A C18 H18B 107.0 . . ? O2 C2 O1 119.3(14) . . ? O2 C2 C3 125.4(14) . . ? O1 C2 C3 115.0(13) . . ? N4 C3 C2 100.8(10) . . ? N4 C3 C21 111.6(12) . . ? C2 C3 C21 109.1(12) . . ? N4 C3 C22 114.1(15) . . ? C2 C3 C22 108.4(14) . . ? C21 C3 C22 112.1(19) . . ? O4 C5 C5' 126.5(11) . . ? O4 C5 N4 113.1(11) . . ? C5' C5 N4 120.3(9) . . ? C5 C5' C6 121.2(9) . . ? C5 C5' C17' 121.5(10) . . ? C6 C5' C17' 117.3(9) . . ? C5' C6 C6' 123.4(9) . . ? C5' C6 O5 117.8(10) . . ? C6' C6 O5 118.6(9) . . ? C6 C6' C16' 117.6(9) . . ? C6 C6' C7' 125.1(9) . . ? C16' C6' C7' 116.4(9) . . ? O8 C23 H23A 109.2 . . ? O8 C23 H23B 109.8 . . ? H23A C23 H23B 109.5 . . ? O8 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C3 C22 H22A 109.4 . . ? C3 C22 H22B 109.7 . . ? H22A C22 H22B 109.5 . . ? C3 C22 H22C 109.3 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C3 C21 O3 97.8(17) . . ? C3 C21 H21A 112.0 . . ? O3 C21 H21A 112.0 . . ? C3 C21 H21B 112.4 . . ? O3 C21 H21B 112.4 . . ? H21A C21 H21B 109.8 . . ? C18 C19 O1 130.2(14) . . ? C18 C19 N4 124.9(13) . . ? O1 C19 N4 104.8(12) . . ? C18 C19 C20 86(3) . . ? O1 C19 C20 98(3) . . ? N4 C19 C20 90(3) . . ? C19 C20 H20A 109.9 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.0 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 C23 O8 C10 C11 176.6(9) . . . . ? C23 O8 C10 C9 3.5(16) . . . . ? O9 C11 C10 O8 3.7(15) . . . . ? C11' C11 C10 O8 179.9(9) . . . . ? O9 C11 C10 C9 177.1(10) . . . . ? C11' C11 C10 C9 -6.6(16) . . . . ? O8 C10 C9 C8 176.3(11) . . . . ? C11 C10 C9 C8 3.2(18) . . . . ? C10 C9 C8 C8' 3(2) . . . . ? C9 C8 C8' O7 179.1(11) . . . . ? C9 C8 C8' C11' -6(2) . . . . ? C7'' O7 C8' C8 175.5(10) . . . . ? C7'' O7 C8' C11' 0.9(16) . . . . ? C8' O7 C7'' C12' -0.4(15) . . . . ? C8' O7 C7'' C7' -178.0(9) . . . . ? O7 C7'' C7' C14' -169.1(9) . . . . ? C12' C7'' C7' C14' 13.3(15) . . . . ? O7 C7'' C7' C6' 4.3(15) . . . . ? C12' C7'' C7' C6' -173.4(9) . . . . ? C7'' C7' C14' C14 -13.3(16) . . . . ? C6' C7' C14' C14 173.2(10) . . . . ? C7'' C7' C14' C15 164.8(10) . . . . ? C6' C7' C14' C15 -8.7(15) . . . . ? C7' C14' C14 O12 -170.2(10) . . . . ? C15 C14' C14 O12 11.8(15) . . . . ? C7' C14' C14 C13 5.3(16) . . . . ? C15 C14' C14 C13 -172.7(9) . . . . ? O12 C14 C13 O11 -3.8(15) . . . . ? C14' C14 C13 O11 -179.4(9) . . . . ? O12 C14 C13 C12' 178.5(9) . . . . ? C14' C14 C13 C12' 3.0(15) . . . . ? O11 C13 C12' C7'' -179.9(9) . . . . ? C14 C13 C12' C7'' -2.4(15) . . . . ? O11 C13 C12' C12 -3.6(16) . . . . ? C14 C13 C12' C12 174.0(9) . . . . ? O7 C7'' C12' C13 176.8(10) . . . . ? C7' C7'' C12' C13 -5.6(15) . . . . ? O7 C7'' C12' C12 0.2(14) . . . . ? C7' C7'' C12' C12 177.8(9) . . . . ? C13 C12' C12 O10 2.2(15) . . . . ? C7'' C12' C12 O10 178.6(8) . . . . ? C13 C12' C12 C11' -177.0(10) . . . . ? C7'' C12' C12 C11' -0.5(14) . . . . ? O9 C11 C11' C8' 179.7(9) . . . . ? C10 C11 C11' C8' 3.8(17) . . . . ? O9 C11 C11' C12 -1.8(16) . . . . ? C10 C11 C11' C12 -177.8(10) . . . . ? C8 C8' C11' C11 2.8(18) . . . . ? O7 C8' C11' C11 177.2(9) . . . . ? C8 C8' C11' C12 -175.7(11) . . . . ? O7 C8' C11' C12 -1.2(17) . . . . ? O10 C12 C11' C11 3.4(16) . . . . ? C12' C12 C11' C11 -177.4(10) . . . . ? O10 C12 C11' C8' -178.1(10) . . . . ? C12' C12 C11' C8' 1.0(15) . . . . ? C7' C14' C15 C16 -36.5(13) . . . . ? C14 C14' C15 C16 141.7(10) . . . . ? C14' C15 C16 C16' 61.3(12) . . . . ? C15 C16 C16' C17 128.0(11) . . . . ? C15 C16 C16' C6' -41.7(14) . . . . ? C6' C16' C17 C17' 3.0(15) . . . . ? C16 C16' C17 C17' -166.2(11) . . . . ? C16' C17 C17' C5' 0.4(16) . . . . ? C16' C17 C17' C18 -179.5(10) . . . . ? C17 C17' C18 C19 -173(3) . . . . ? C5' C17' C18 C19 7(3) . . . . ? C19 O1 C2 O2 177(3) . . . . ? C19 O1 C2 C3 3(3) . . . . ? C5 N4 C3 C2 -177.1(12) . . . . ? C19 N4 C3 C2 -10(3) . . . . ? C5 N4 C3 C21 67.2(18) . . . . ? C19 N4 C3 C21 -126(2) . . . . ? C5 N4 C3 C22 -61(2) . . . . ? C19 N4 C3 C22 106(3) . . . . ? O2 C2 C3 N4 -168.8(14) . . . . ? O1 C2 C3 N4 4.6(16) . . . . ? O2 C2 C3 C21 -51.3(19) . . . . ? O1 C2 C3 C21 122.2(15) . . . . ? O2 C2 C3 C22 71(2) . . . . ? O1 C2 C3 C22 -115.5(19) . . . . ? C3 N4 C5 O4 -10.2(19) . . . . ? C19 N4 C5 O4 -176(3) . . . . ? C3 N4 C5 C5' 174.1(13) . . . . ? C19 N4 C5 C5' 8(3) . . . . ? O4 C5 C5' C6 0.2(18) . . . . ? N4 C5 C5' C6 175.3(10) . . . . ? O4 C5 C5' C17' 178.7(11) . . . . ? N4 C5 C5' C17' -6.2(17) . . . . ? C17 C17' C5' C5 178.8(11) . . . . ? C18 C17' C5' C5 -1.3(16) . . . . ? C17 C17' C5' C6 -2.6(15) . . . . ? C18 C17' C5' C6 177.3(10) . . . . ? C5 C5' C6 C6' -179.8(11) . . . . ? C17' C5' C6 C6' 1.6(16) . . . . ? C5 C5' C6 O5 -4.9(16) . . . . ? C17' C5' C6 O5 176.5(9) . . . . ? C5' C6 C6' C16' 1.6(16) . . . . ? O5 C6 C6' C16' -173.3(9) . . . . ? C5' C6 C6' C7' 170.7(10) . . . . ? O5 C6 C6' C7' -4.2(16) . . . . ? C17 C16' C6' C6 -4.0(15) . . . . ? C16 C16' C6' C6 165.7(10) . . . . ? C17 C16' C6' C7' -174.0(10) . . . . ? C16 C16' C6' C7' -4.3(14) . . . . ? C14' C7' C6' C6 -137.6(11) . . . . ? C7'' C7' C6' C6 49.2(16) . . . . ? C14' C7' C6' C16' 31.6(14) . . . . ? C7'' C7' C6' C16' -141.6(10) . . . . ? N4 C3 C21 O3 60.0(15) . . . . ? C2 C3 C21 O3 -50.4(17) . . . . ? C22 C3 C21 O3 -170.5(12) . . . . ? C17' C18 C19 O1 169(4) . . . . ? C17' C18 C19 N4 -6(6) . . . . ? C17' C18 C19 C20 -93(2) . . . . ? C2 O1 C19 C18 175(5) . . . . ? C2 O1 C19 N4 -9(4) . . . . ? C2 O1 C19 C20 82.6(17) . . . . ? C5 N4 C19 C18 -2(6) . . . . ? C3 N4 C19 C18 -171(4) . . . . ? C5 N4 C19 O1 -178(2) . . . . ? C3 N4 C19 O1 13(4) . . . . ? C5 N4 C19 C20 84(2) . . . . ? C3 N4 C19 C20 -85.8(12) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O9 H9B O10 0.82 1.86 2.591(10) 147.4 . O11 H11A O10 0.82 1.87 2.593(10) 145.9 . O5 H5A O4 0.82 1.78 2.518(10) 148.4 . O3 H3A O1' 0.82 2.05 2.87(3) 175.5 . _diffrn_measured_fraction_theta_max 0.902 _diffrn_reflns_theta_full 66.98 _diffrn_measured_fraction_theta_full 0.902 _refine_diff_density_max 0.844 _refine_diff_density_min -0.579 _refine_diff_density_rms 0.223