data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'G. Pattenden' 'Manuel Cases' 'Gonzalez-Lopez de Turiso,Felix' 'Maria S. Hadjisoteriou' _publ_contact_author_name 'Prof G Pattenden' _publ_contact_author_address ; Chemistry Department The University University Park NOTTINGHAM NG7 2RD UNITED KINGDOM ; _publ_contact_author_email GP@NOTTINGHAM.AC.UK _publ_requested_journal 'Organic & Biomolecular Chemistry' _publ_section_title ; Synthetic Studies Towards Furanocembrane Diterpenes. A Total Synthesis of bis-Deoxylophotoxin ; data_PONEST _database_code_depnum_ccdc_archive 'CCDC 270127' _refine_special_details ; Even with the high intensity available from the synchrotron, these crystals diffracted only to low resolution. ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 O6' _chemical_formula_sum 'C22 H26 O6' _chemical_formula_weight 386.43 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' O O 0.0106 0.0060 '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' 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 6.565(4) _cell_length_b 8.698(5) _cell_length_c 34.72(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1983(2) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3656 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 22.4 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.6861 _diffrn_radiation_type synchrotron _diffrn_radiation_source 'Daresbury Laboratory Station 9.8' _diffrn_radiation_monochromator 'silicon (111)' _diffrn_measurement_device_type 'Bruker SMART1k CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number . _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 5116 _diffrn_reflns_av_R_equivalents 0.062 _diffrn_reflns_av_sigmaI/netI 0.058 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -38 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 2.27 _diffrn_reflns_theta_max 22.40 _reflns_number_total 1651 _reflns_number_gt 1456 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL; PLATON (Spek, 2002)' _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^)+(0.095P)^2^+7.56P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'geometrically placed' _refine_ls_hydrogen_treatment 'riding model' _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(5) _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 -2(5) _refine_ls_number_reflns 1651 _refine_ls_number_parameters 254 _refine_ls_number_restraints 73 _refine_ls_R_factor_all 0.0982 _refine_ls_R_factor_gt 0.0878 _refine_ls_wR_factor_ref 0.222 _refine_ls_wR_factor_gt 0.216 _refine_ls_goodness_of_fit_ref 1.09 _refine_ls_restrained_S_all 1.07 _refine_ls_shift/su_max 0.002 _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 C1 C 0.0515(12) 0.5260(10) 0.8354(2) 0.0272(18) Uani 1 1 d U . . H1 H 0.1424 0.4398 0.8436 0.033 Uiso 1 1 calc R . . C2 C -0.0807(13) 0.4662(10) 0.8018(2) 0.0277(19) Uani 1 1 d U . . H2A H -0.1733 0.5493 0.7933 0.033 Uiso 1 1 calc R . . H2B H 0.0092 0.4399 0.7798 0.033 Uiso 1 1 calc R . . C3 C -0.2056(13) 0.3270(11) 0.8122(2) 0.032(2) Uani 1 1 d U . . O3 O -0.1313(9) 0.2426(7) 0.84192(17) 0.0352(15) Uani 1 1 d U . . C4 C -0.3848(13) 0.2648(12) 0.8004(2) 0.035(2) Uani 1 1 d U . . C5 C -0.4211(14) 0.1359(12) 0.8252(2) 0.040(2) Uani 1 1 d U . . H5 H -0.5350 0.0689 0.8235 0.048 Uiso 1 1 calc R . . C6 C -0.2731(14) 0.1241(10) 0.8506(3) 0.038(2) Uani 1 1 d U . . C7 C -0.2328(16) 0.0579(10) 0.8880(3) 0.039(2) Uani 1 1 d U . . H7 H -0.3484 0.0312 0.9031 0.047 Uiso 1 1 calc R . . C8 C -0.0496(15) 0.0298(10) 0.9039(3) 0.037(2) Uani 1 1 d U . . C9 C -0.0260(15) 0.0169(10) 0.9463(3) 0.040(2) Uani 1 1 d U . . H9A H 0.0784 -0.0620 0.9520 0.048 Uiso 1 1 calc R . . H9B H -0.1565 -0.0184 0.9575 0.048 Uiso 1 1 calc R . . C10 C 0.0365(13) 0.1694(9) 0.9657(3) 0.0315(19) Uani 1 1 d U . . H10 H 0.0210 0.1582 0.9942 0.038 Uiso 1 1 calc R . . O10 O 0.2508(9) 0.2061(7) 0.95698(16) 0.0362(15) Uani 1 1 d U . . C11 C -0.0749(13) 0.3152(9) 0.9528(2) 0.031(2) Uani 1 1 d U . . H11 H -0.2144 0.2911 0.9438 0.037 Uiso 1 1 calc R . . H11B H -0.0832 0.3908 0.9741 0.037 Uiso 1 1 calc R . . C12 C 0.0543(13) 0.3758(10) 0.9202(2) 0.0281(19) Uani 1 1 d U . . H12 H 0.0160 0.3157 0.8967 0.034 Uiso 1 1 calc R . . O13 O 0.2036(8) 0.6391(7) 0.91207(15) 0.0296(14) Uani 1 1 d U . . C13 C 0.0165(12) 0.5492(9) 0.9104(2) 0.0257(18) Uani 1 1 d U . . H13 H -0.0802 0.5918 0.9299 0.031 Uiso 1 1 calc R . . C14 C -0.0745(13) 0.5747(10) 0.8710(2) 0.0295(19) Uani 1 1 d U . . H14A H -0.1053 0.6857 0.8684 0.035 Uiso 1 1 calc R . . H14B H -0.2060 0.5192 0.8700 0.035 Uiso 1 1 calc R . . C15 C 0.1881(12) 0.6548(10) 0.8203(2) 0.0253(18) Uani 1 1 d U . . C16 C 0.3885(12) 0.6518(10) 0.8279(3) 0.032(2) Uani 1 1 d U . . H16A H 0.4744 0.7313 0.8185 0.038 Uiso 1 1 calc R . . H16B H 0.4445 0.5702 0.8426 0.038 Uiso 1 1 calc R . . C17 C 0.0903(14) 0.7786(10) 0.7974(3) 0.037(2) Uani 1 1 d U . . H17A H 0.1936 0.8533 0.7894 0.056 Uiso 1 1 calc R . . H17B H -0.0130 0.8302 0.8131 0.056 Uiso 1 1 calc R . . H17C H 0.0256 0.7339 0.7745 0.056 Uiso 1 1 calc R . . C18 C -0.5157(13) 0.3229(13) 0.7701(3) 0.046(2) Uani 1 1 d U . . H18 H -0.4790 0.4166 0.7579 0.055 Uiso 1 1 calc R . . O18 O -0.6714(11) 0.2576(11) 0.7594(2) 0.066(2) Uani 1 1 d U . . C19 C 0.1383(15) 0.0157(10) 0.8795(3) 0.040(2) Uani 1 1 d U . . H19A H 0.1016 0.0268 0.8523 0.061 Uiso 1 1 calc R . . H19B H 0.2007 -0.0853 0.8837 0.061 Uiso 1 1 calc R . . H19C H 0.2354 0.0964 0.8866 0.061 Uiso 1 1 calc R . . C20 C 0.2659(14) 0.3244(9) 0.9314(2) 0.0301(19) Uani 1 1 d U . . O20 O 0.4292(9) 0.3663(7) 0.91994(19) 0.0403(17) Uani 1 1 d U . . C21 C 0.2882(14) 0.6542(10) 0.9468(2) 0.0330(19) Uani 1 1 d U . . O21 O 0.2153(11) 0.6064(7) 0.97610(17) 0.0402(16) Uani 1 1 d U . . C22 C 0.4850(16) 0.7428(13) 0.9453(3) 0.054(3) Uani 1 1 d U . . H22A H 0.5421 0.7510 0.9713 0.081 Uiso 1 1 calc R . . H22B H 0.4593 0.8459 0.9351 0.081 Uiso 1 1 calc R . . H22C H 0.5818 0.6890 0.9286 0.081 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 C1 0.018(4) 0.028(4) 0.036(4) 0.001(4) -0.008(3) 0.004(4) C2 0.026(5) 0.022(4) 0.035(4) -0.004(3) -0.006(4) -0.001(4) C3 0.023(4) 0.042(5) 0.032(4) -0.004(4) -0.005(4) -0.008(4) O3 0.029(3) 0.031(3) 0.046(3) 0.001(3) -0.006(3) -0.010(3) C4 0.019(4) 0.049(5) 0.036(5) -0.015(4) 0.004(3) -0.002(4) C5 0.029(5) 0.046(5) 0.046(5) -0.015(4) 0.010(4) -0.021(5) C6 0.034(5) 0.026(5) 0.054(5) -0.003(4) 0.004(4) -0.011(4) C7 0.041(5) 0.023(5) 0.053(5) -0.001(4) 0.008(4) -0.020(5) C8 0.043(5) 0.013(4) 0.054(5) -0.002(4) 0.007(4) -0.009(4) C9 0.036(5) 0.023(4) 0.060(5) -0.001(4) 0.010(4) -0.009(4) C10 0.028(4) 0.018(4) 0.049(5) 0.012(3) 0.003(4) -0.002(4) O10 0.031(3) 0.029(3) 0.048(3) 0.011(3) -0.004(3) 0.000(3) C11 0.027(4) 0.020(4) 0.044(5) 0.002(4) 0.001(4) 0.012(4) C12 0.025(4) 0.020(4) 0.040(5) 0.003(4) -0.004(4) 0.009(4) O13 0.027(3) 0.024(3) 0.038(3) -0.004(3) -0.007(3) 0.006(3) C13 0.016(4) 0.010(4) 0.050(4) 0.000(3) 0.009(4) 0.002(3) C14 0.028(5) 0.022(4) 0.039(4) -0.001(3) -0.001(3) 0.001(4) C15 0.021(4) 0.030(4) 0.026(4) -0.003(3) -0.006(3) -0.002(4) C16 0.020(4) 0.014(4) 0.061(6) 0.000(4) -0.005(4) -0.014(4) C17 0.035(5) 0.027(5) 0.050(5) 0.011(4) -0.007(4) -0.011(4) C18 0.023(5) 0.059(7) 0.055(5) -0.018(5) -0.004(4) 0.009(5) O18 0.038(4) 0.084(6) 0.078(5) -0.020(5) -0.014(4) -0.005(4) C19 0.047(5) 0.022(5) 0.052(5) -0.002(4) 0.002(4) -0.006(5) C20 0.031(4) 0.022(4) 0.037(4) 0.003(3) -0.004(4) 0.002(4) O20 0.024(3) 0.026(3) 0.071(4) 0.002(3) 0.003(3) 0.002(3) C21 0.036(5) 0.030(5) 0.033(4) -0.006(4) 0.001(4) 0.016(4) O21 0.050(4) 0.033(3) 0.038(3) -0.002(3) -0.002(3) 0.006(3) C22 0.050(6) 0.052(7) 0.059(6) -0.005(5) -0.014(5) -0.023(6) _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 C1 C2 1.546(11) . ? C1 C14 1.544(11) . ? C1 C15 1.529(12) . ? C1 H1 1.0000 . ? C2 C3 1.507(12) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 O3 1.357(10) . ? C3 C4 1.359(12) . ? O3 C6 1.421(10) . ? C4 C5 1.433(14) . ? C4 C18 1.447(12) . ? C5 C6 1.318(13) . ? C5 H5 0.9500 . ? C6 C7 1.445(13) . ? C7 C8 1.345(14) . ? C7 H7 0.9500 . ? C8 C9 1.485(13) . ? C8 C19 1.501(13) . ? C9 C10 1.544(12) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O10 1.474(11) . ? C10 C11 1.531(11) . ? C10 H10 1.0000 . ? O10 C20 1.363(10) . ? C11 C12 1.510(12) . ? C11 H11 0.9900 . ? C11 H11B 0.9900 . ? C12 C20 1.510(12) . ? C12 C13 1.566(11) . ? C12 H12 1.0000 . ? O13 C21 1.335(10) . ? O13 C13 1.457(10) . ? C13 C14 1.510(12) . ? C13 H13 1.0000 . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.342(11) . ? C15 C17 1.484(12) . ? C16 H16A 0.9500 . ? C16 H16B 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O18 1.228(12) . ? C18 H18 0.9500 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 O20 1.200(11) . ? C21 O21 1.197(10) . ? C21 C22 1.505(14) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 C15 C1 C14 112.9(7) . . ? C15 C1 C2 108.4(6) . . ? C14 C1 C2 113.3(7) . . ? C15 C1 H1 107.3 . . ? C14 C1 H1 107.3 . . ? C2 C1 H1 107.3 . . ? C3 C2 C1 113.2(7) . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? O3 C3 C4 109.0(8) . . ? O3 C3 C2 115.0(7) . . ? C4 C3 C2 135.9(9) . . ? C3 O3 C6 108.6(6) . . ? C3 C4 C5 105.8(8) . . ? C3 C4 C18 126.5(10) . . ? C5 C4 C18 127.6(9) . . ? C6 C5 C4 110.0(8) . . ? C6 C5 H5 125.0 . . ? C4 C5 H5 125.0 . . ? C5 C6 O3 106.5(8) . . ? C5 C6 C7 140.3(9) . . ? O3 C6 C7 111.1(7) . . ? C8 C7 C6 127.1(9) . . ? C8 C7 H7 116.4 . . ? C6 C7 H7 116.4 . . ? C7 C8 C9 120.8(9) . . ? C7 C8 C19 121.3(8) . . ? C9 C8 C19 117.9(9) . . ? C8 C9 C10 113.3(7) . . ? C8 C9 H9A 108.9 . . ? C10 C9 H9A 108.9 . . ? C8 C9 H9B 108.9 . . ? C10 C9 H9B 108.9 . . ? H9A C9 H9B 107.7 . . ? O10 C10 C11 102.5(6) . . ? O10 C10 C9 110.5(7) . . ? C11 C10 C9 117.2(7) . . ? O10 C10 H10 108.8 . . ? C11 C10 H10 108.8 . . ? C9 C10 H10 108.8 . . ? C20 O10 C10 111.5(7) . . ? C12 C11 C10 103.9(7) . . ? C12 C11 H11 111.0 . . ? C10 C11 H11 111.0 . . ? C12 C11 H11B 111.0 . . ? C10 C11 H11B 111.0 . . ? H11 C11 H11B 109.0 . . ? C11 C12 C20 102.7(7) . . ? C11 C12 C13 114.2(7) . . ? C20 C12 C13 119.1(7) . . ? C11 C12 H12 106.7 . . ? C20 C12 H12 106.7 . . ? C13 C12 H12 106.7 . . ? C21 O13 C13 116.1(7) . . ? O13 C13 C14 106.9(6) . . ? O13 C13 C12 112.0(6) . . ? C14 C13 C12 113.6(7) . . ? O13 C13 H13 108.0 . . ? C14 C13 H13 108.0 . . ? C12 C13 H13 108.0 . . ? C13 C14 C1 118.1(7) . . ? C13 C14 H14A 107.8 . . ? C1 C14 H14A 107.8 . . ? C13 C14 H14B 107.8 . . ? C1 C14 H14B 107.8 . . ? H14A C14 H14B 107.1 . . ? C16 C15 C17 122.9(9) . . ? C16 C15 C1 119.5(8) . . ? C17 C15 C1 117.5(7) . . ? C15 C16 H16A 120.0 . . ? C15 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? O18 C18 C4 123.6(11) . . ? O18 C18 H18 118.2 . . ? C4 C18 H18 118.2 . . ? C8 C19 H19A 109.5 . . ? C8 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C8 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O20 C20 O10 120.7(8) . . ? O20 C20 C12 130.3(7) . . ? O10 C20 C12 108.9(7) . . ? O21 C21 O13 124.5(9) . . ? O21 C21 C22 123.4(9) . . ? O13 C21 C22 112.0(8) . . ? 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 . . ? 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 C15 C1 C2 C3 173.7(7) . . . . ? C14 C1 C2 C3 -60.2(9) . . . . ? C1 C2 C3 O3 -24.1(10) . . . . ? C1 C2 C3 C4 152.3(10) . . . . ? C4 C3 O3 C6 -2.4(9) . . . . ? C2 C3 O3 C6 174.9(7) . . . . ? O3 C3 C4 C5 1.0(9) . . . . ? C2 C3 C4 C5 -175.5(9) . . . . ? O3 C3 C4 C18 178.1(8) . . . . ? C2 C3 C4 C18 1.6(16) . . . . ? C3 C4 C5 C6 0.9(10) . . . . ? C18 C4 C5 C6 -176.2(9) . . . . ? C4 C5 C6 O3 -2.3(10) . . . . ? C4 C5 C6 C7 158.4(11) . . . . ? C3 O3 C6 C5 2.9(10) . . . . ? C3 O3 C6 C7 -164.0(8) . . . . ? C5 C6 C7 C8 161.7(12) . . . . ? O3 C6 C7 C8 -38.2(13) . . . . ? C6 C7 C8 C9 157.2(8) . . . . ? C6 C7 C8 C19 -20.8(15) . . . . ? C7 C8 C9 C10 -94.2(11) . . . . ? C19 C8 C9 C10 83.9(10) . . . . ? C8 C9 C10 O10 -72.5(10) . . . . ? C8 C9 C10 C11 44.4(12) . . . . ? C11 C10 O10 C20 -18.6(9) . . . . ? C9 C10 O10 C20 107.0(7) . . . . ? O10 C10 C11 C12 30.3(8) . . . . ? C9 C10 C11 C12 -90.8(9) . . . . ? C10 C11 C12 C20 -30.9(9) . . . . ? C10 C11 C12 C13 -161.3(7) . . . . ? C21 O13 C13 C14 168.4(7) . . . . ? C21 O13 C13 C12 -66.5(9) . . . . ? C11 C12 C13 O13 124.4(8) . . . . ? C20 C12 C13 O13 2.6(11) . . . . ? C11 C12 C13 C14 -114.3(8) . . . . ? C20 C12 C13 C14 123.9(8) . . . . ? O13 C13 C14 C1 61.0(9) . . . . ? C12 C13 C14 C1 -63.2(10) . . . . ? C15 C1 C14 C13 -90.3(9) . . . . ? C2 C1 C14 C13 146.0(7) . . . . ? C14 C1 C15 C16 103.1(9) . . . . ? C2 C1 C15 C16 -130.6(8) . . . . ? C14 C1 C15 C17 -77.0(9) . . . . ? C2 C1 C15 C17 49.3(9) . . . . ? C3 C4 C18 O18 176.4(9) . . . . ? C5 C4 C18 O18 -7.1(15) . . . . ? C10 O10 C20 O20 -177.4(8) . . . . ? C10 O10 C20 C12 -1.0(9) . . . . ? C11 C12 C20 O20 -163.6(9) . . . . ? C13 C12 C20 O20 -36.2(14) . . . . ? C11 C12 C20 O10 20.4(9) . . . . ? C13 C12 C20 O10 147.8(7) . . . . ? C13 O13 C21 O21 -4.2(12) . . . . ? C13 O13 C21 C22 177.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 22.40 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.35 _refine_diff_density_min -0.35 _refine_diff_density_rms 0.08 data_IMFUOM _database_code_depnum_ccdc_archive 'CCDC 270128' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H23 N O6' _chemical_formula_sum 'C18 H23 N O6' _chemical_formula_weight 349.37 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 10.816(2) _cell_length_b 16.904(3) _cell_length_c 19.350(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3537.8(12) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3448 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 24.2 _exptl_crystal_description lath _exptl_crystal_colour colourless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.312 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1488 _exptl_absorpt_coefficient_mu 0.099 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 21946 _diffrn_reflns_av_R_equivalents 0.057 _diffrn_reflns_av_sigmaI/netI 0.066 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 28.63 _reflns_number_total 8076 _reflns_number_gt 5911 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.054 (Bruker, 1998)' _computing_cell_refinement 'Bruker SAINT version 6.02A (Bruker, 2000)' _computing_data_reduction 'Bruker SAINT; Bruker SHELXTL (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'SHELXL-97; PLATON (Spek, 2000)' _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^)+(0.0319P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary . _atom_sites_solution_hydrogens 'Me on sp2 C from delta-F; others placed geometrically' _refine_ls_hydrogen_treatment 'rigid rotating group; riding model' _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 0.0(6) _refine_ls_number_reflns 8076 _refine_ls_number_parameters 453 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0647 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0789 _refine_ls_wR_factor_gt 0.0724 _refine_ls_goodness_of_fit_ref 0.921 _refine_ls_restrained_S_all 0.921 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.002 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 O1 O 0.52389(12) 0.13488(7) 0.07334(6) 0.0325(3) Uani 1 1 d . . . C2 C 0.44157(18) 0.18360(11) 0.10304(10) 0.0306(4) Uani 1 1 d . . . N3 N 0.49310(14) 0.21467(8) 0.16274(7) 0.0255(3) Uani 1 1 d . . . C4 C 0.61600(17) 0.18102(10) 0.17647(9) 0.0275(4) Uani 1 1 d . . . H4A H 0.6768 0.2246 0.1846 0.033 Uiso 1 1 calc R . . C5 C 0.64277(16) 0.14138(11) 0.10723(9) 0.0280(4) Uani 1 1 d . . . H5A H 0.7003 0.1739 0.0794 0.034 Uiso 1 1 calc R . . H5B H 0.6799 0.0884 0.1142 0.034 Uiso 1 1 calc R . . C6 C 0.61502(19) 0.12514(12) 0.23827(10) 0.0360(5) Uani 1 1 d . . . H6A H 0.5878 0.1564 0.2794 0.043 Uiso 1 1 calc R . . C7 C 0.7461(2) 0.09478(14) 0.25316(11) 0.0483(6) Uani 1 1 d . . . H7A H 0.8022 0.1398 0.2588 0.072 Uiso 1 1 calc R . . H7B H 0.7743 0.0619 0.2145 0.072 Uiso 1 1 calc R . . H7C H 0.7455 0.0632 0.2956 0.072 Uiso 1 1 calc R . . C8 C 0.5241(2) 0.05690(13) 0.22947(12) 0.0520(6) Uani 1 1 d . . . H8A H 0.4415 0.0780 0.2200 0.078 Uiso 1 1 calc R . . H8B H 0.5219 0.0254 0.2720 0.078 Uiso 1 1 calc R . . H8C H 0.5506 0.0235 0.1908 0.078 Uiso 1 1 calc R . . C9 C 0.44310(17) 0.27283(10) 0.20544(10) 0.0285(4) Uani 1 1 d . . . O10 O 0.50590(13) 0.29775(8) 0.25237(7) 0.0426(4) Uani 1 1 d . . . C11 C 0.31499(17) 0.30418(10) 0.19004(9) 0.0265(4) Uani 1 1 d . . . H11A H 0.2600 0.2589 0.1774 0.032 Uiso 1 1 calc R . . C13 C 0.26050(18) 0.34673(10) 0.25367(9) 0.0284(4) Uani 1 1 d . . . H13A H 0.3259 0.3804 0.2741 0.034 Uiso 1 1 calc R . . H13B H 0.1935 0.3822 0.2377 0.034 Uiso 1 1 calc R . . C14 C 0.21010(17) 0.29498(10) 0.30900(9) 0.0272(4) Uani 1 1 d . . . C15 C 0.09337(17) 0.28040(10) 0.33169(9) 0.0258(4) Uani 1 1 d . . . C16 C 0.10465(19) 0.23029(10) 0.39121(10) 0.0329(5) Uani 1 1 d . . . H16A H 0.0393 0.2103 0.4189 0.039 Uiso 1 1 calc R . . C17 C 0.22474(19) 0.21754(11) 0.39978(11) 0.0376(5) Uani 1 1 d . . . H17A H 0.2592 0.1857 0.4354 0.045 Uiso 1 1 calc R . . O18 O 0.29250(12) 0.25640(7) 0.35040(7) 0.0352(3) Uani 1 1 d . . . C19 C -0.01999(17) 0.31333(10) 0.30276(9) 0.0278(4) Uani 1 1 d . . . O20 O -0.02703(13) 0.35372(9) 0.25180(7) 0.0426(4) Uani 1 1 d . . . O21 O -0.11839(12) 0.29318(8) 0.34087(7) 0.0361(3) Uani 1 1 d . . . C22 C -0.23535(18) 0.32558(12) 0.31876(12) 0.0438(5) Uani 1 1 d . . . H22A H -0.3009 0.3074 0.3499 0.066 Uiso 1 1 calc R . . H22B H -0.2533 0.3078 0.2716 0.066 Uiso 1 1 calc R . . H22C H -0.2312 0.3835 0.3198 0.066 Uiso 1 1 calc R . . C23 C 0.31762(18) 0.36268(11) 0.13045(9) 0.0307(4) Uani 1 1 d . . . C24 C 0.4104(2) 0.41267(12) 0.12300(11) 0.0445(5) Uani 1 1 d . . . H24A H 0.4075 0.4519 0.0879 0.062 Uiso 1 1 calc R . . H24B H 0.4801 0.4094 0.1528 0.062 Uiso 1 1 calc R . . C25 C 0.2059(2) 0.36376(14) 0.08635(12) 0.0518(6) Uani 1 1 d . . . H25A H 0.2097 0.4091 0.0548 0.078 Uiso 1 1 calc R . . H25B H 0.1321 0.3682 0.1155 0.078 Uiso 1 1 calc R . . H25C H 0.2017 0.3147 0.0595 0.078 Uiso 1 1 calc R . . O26 O 0.34041(13) 0.19395(8) 0.07994(7) 0.0406(3) Uani 1 1 d . . . O1' O 0.76134(12) 0.31525(7) 0.08262(7) 0.0329(3) Uani 1 1 d . . . C2' C 0.67805(17) 0.34648(10) 0.03935(9) 0.0260(4) Uani 1 1 d . . . N3' N 0.72100(13) 0.42014(8) 0.01720(7) 0.0229(3) Uani 1 1 d . . . C4' C 0.84296(17) 0.43833(10) 0.04667(9) 0.0250(4) Uani 1 1 d . . . H4'A H 0.9029 0.4481 0.0082 0.030 Uiso 1 1 calc R . . C5' C 0.87494(18) 0.35997(10) 0.08180(10) 0.0315(4) Uani 1 1 d . . . H5'A H 0.9396 0.3315 0.0555 0.038 Uiso 1 1 calc R . . H5'B H 0.9051 0.3692 0.1294 0.038 Uiso 1 1 calc R . . C6' C 0.84093(17) 0.51065(10) 0.09479(9) 0.0280(4) Uani 1 1 d . . . H6'A H 0.8189 0.5576 0.0659 0.034 Uiso 1 1 calc R . . C7' C 0.96954(18) 0.52523(11) 0.12400(10) 0.0342(5) Uani 1 1 d . . . H7'A H 0.9676 0.5715 0.1545 0.051 Uiso 1 1 calc R . . H7'B H 1.0275 0.5348 0.0860 0.051 Uiso 1 1 calc R . . H7'C H 0.9963 0.4787 0.1503 0.051 Uiso 1 1 calc R . . C8' C 0.7444(2) 0.50395(13) 0.15110(10) 0.0402(5) Uani 1 1 d . . . H8'A H 0.6631 0.4947 0.1302 0.060 Uiso 1 1 calc R . . H8'B H 0.7423 0.5531 0.1779 0.060 Uiso 1 1 calc R . . H8'C H 0.7652 0.4597 0.1817 0.060 Uiso 1 1 calc R . . C9' C 0.67300(17) 0.46662(10) -0.03567(9) 0.0249(4) Uani 1 1 d . . . O10' O 0.73547(12) 0.52064(7) -0.05754(7) 0.0346(3) Uani 1 1 d . . . C11' C 0.54504(16) 0.44843(10) -0.06365(9) 0.0256(4) Uani 1 1 d . . . H11B H 0.4953 0.4219 -0.0268 0.031 Uiso 1 1 calc R . . C13' C 0.48130(18) 0.52707(10) -0.08408(9) 0.0289(4) Uani 1 1 d . . . H13C H 0.5418 0.5605 -0.1090 0.035 Uiso 1 1 calc R . . H13D H 0.4128 0.5152 -0.1164 0.035 Uiso 1 1 calc R . . C14' C 0.43132(17) 0.57269(10) -0.02467(9) 0.0277(4) Uani 1 1 d . . . C15' C 0.31706(18) 0.59971(10) -0.00790(9) 0.0280(4) Uani 1 1 d . . . C16' C 0.3293(2) 0.64278(12) 0.05568(10) 0.0360(5) Uani 1 1 d . . . H16B H 0.2656 0.6690 0.0805 0.043 Uiso 1 1 calc R . . C17' C 0.4484(2) 0.63842(13) 0.07272(10) 0.0428(5) Uani 1 1 d . . . H17B H 0.4835 0.6615 0.1129 0.051 Uiso 1 1 calc R . . O18' O 0.51365(12) 0.59615(8) 0.02450(7) 0.0373(3) Uani 1 1 d . . . C19' C 0.20513(17) 0.58966(11) -0.04989(10) 0.0291(4) Uani 1 1 d . . . O20' O 0.19870(13) 0.55043(7) -0.10171(7) 0.0362(3) Uani 1 1 d . . . O21' O 0.10969(12) 0.63036(8) -0.02423(7) 0.0367(3) Uani 1 1 d . . . C22' C -0.00224(18) 0.62550(13) -0.06448(11) 0.0438(5) Uani 1 1 d . . . H22D H -0.0672 0.6568 -0.0421 0.066 Uiso 1 1 calc R . . H22E H -0.0287 0.5702 -0.0677 0.066 Uiso 1 1 calc R . . H22F H 0.0131 0.6463 -0.1110 0.066 Uiso 1 1 calc R . . C23' C 0.55342(17) 0.39422(11) -0.12601(10) 0.0301(4) Uani 1 1 d . . . C25' C 0.6295(2) 0.42162(13) -0.18639(10) 0.0456(6) Uani 1 1 d . . . H25D H 0.6266 0.3817 -0.2231 0.068 Uiso 1 1 calc R . . H25E H 0.7154 0.4293 -0.1716 0.068 Uiso 1 1 calc R . . H25F H 0.5963 0.4717 -0.2038 0.068 Uiso 1 1 calc R . . C24' C 0.4914(2) 0.32673(12) -0.12739(11) 0.0414(5) Uani 1 1 d . . . H24C H 0.4943 0.2941 -0.1673 0.058 Uiso 1 1 calc R . . H24D H 0.4440 0.3109 -0.0884 0.058 Uiso 1 1 calc R . . O26' O 0.58330(12) 0.31390(7) 0.02561(7) 0.0322(3) Uani 1 1 d . . . 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 O1 0.0328(7) 0.0324(7) 0.0324(7) -0.0112(6) 0.0006(6) 0.0021(6) C2 0.0318(12) 0.0280(10) 0.0320(11) -0.0028(9) 0.0010(9) -0.0026(9) N3 0.0251(8) 0.0251(7) 0.0262(8) -0.0027(6) -0.0002(7) 0.0022(7) C4 0.0263(10) 0.0273(9) 0.0290(10) -0.0042(8) 0.0013(8) 0.0035(8) C5 0.0300(11) 0.0255(9) 0.0285(10) -0.0008(8) 0.0045(8) 0.0001(8) C6 0.0387(12) 0.0428(11) 0.0265(11) 0.0034(9) 0.0052(9) 0.0110(10) C7 0.0469(13) 0.0567(14) 0.0412(13) 0.0086(11) -0.0005(11) 0.0197(12) C8 0.0455(14) 0.0545(14) 0.0559(14) 0.0262(11) 0.0149(12) 0.0052(12) C9 0.0286(10) 0.0258(9) 0.0311(11) -0.0063(8) 0.0016(9) 0.0004(8) O10 0.0307(8) 0.0516(8) 0.0455(8) -0.0246(7) -0.0087(7) 0.0073(7) C11 0.0254(10) 0.0250(9) 0.0291(10) -0.0046(8) -0.0004(8) -0.0022(8) C13 0.0286(10) 0.0258(9) 0.0307(10) -0.0006(8) 0.0029(9) -0.0002(8) C14 0.0291(10) 0.0222(9) 0.0303(10) -0.0036(8) -0.0027(8) 0.0017(8) C15 0.0286(10) 0.0239(9) 0.0250(10) -0.0048(8) 0.0004(8) -0.0008(8) C16 0.0362(12) 0.0279(10) 0.0346(11) 0.0010(8) 0.0010(10) -0.0037(9) C17 0.0427(13) 0.0284(10) 0.0416(12) 0.0092(9) -0.0050(10) -0.0014(9) O18 0.0294(8) 0.0288(7) 0.0473(9) 0.0063(6) -0.0032(7) 0.0008(6) C19 0.0289(10) 0.0296(10) 0.0249(10) -0.0098(8) 0.0004(8) -0.0034(8) O20 0.0366(8) 0.0609(9) 0.0303(8) 0.0080(7) -0.0024(7) 0.0061(7) O21 0.0255(7) 0.0389(7) 0.0439(8) 0.0017(6) 0.0026(6) 0.0001(6) C22 0.0254(11) 0.0514(13) 0.0544(14) -0.0041(11) 0.0006(10) 0.0005(10) C23 0.0324(11) 0.0307(10) 0.0289(10) -0.0037(8) 0.0049(9) 0.0068(9) C24 0.0522(14) 0.0391(11) 0.0420(13) -0.0025(10) 0.0084(11) -0.0066(11) C25 0.0512(15) 0.0532(14) 0.0509(15) 0.0055(12) -0.0126(12) 0.0075(12) O26 0.0318(8) 0.0484(9) 0.0417(8) -0.0167(7) -0.0071(7) 0.0028(7) O1' 0.0345(8) 0.0269(7) 0.0373(8) 0.0094(6) -0.0053(6) -0.0022(6) C2' 0.0289(10) 0.0250(9) 0.0241(10) 0.0020(8) 0.0049(8) 0.0031(8) N3' 0.0258(8) 0.0208(7) 0.0221(8) 0.0004(6) 0.0011(6) 0.0001(6) C4' 0.0271(10) 0.0257(9) 0.0223(9) 0.0010(7) -0.0009(8) 0.0029(8) C5' 0.0361(11) 0.0273(9) 0.0311(11) 0.0048(8) -0.0075(9) 0.0006(9) C6' 0.0325(11) 0.0234(9) 0.0282(10) -0.0006(8) -0.0018(8) 0.0003(8) C7' 0.0351(12) 0.0326(10) 0.0349(11) -0.0033(9) -0.0038(9) -0.0046(9) C8' 0.0388(12) 0.0470(12) 0.0349(12) -0.0138(9) 0.0028(10) -0.0054(10) C9' 0.0285(10) 0.0269(9) 0.0193(9) 0.0002(8) 0.0016(8) 0.0011(8) O10' 0.0330(8) 0.0341(7) 0.0368(8) 0.0143(6) -0.0040(6) -0.0071(6) C11' 0.0261(10) 0.0269(9) 0.0238(9) 0.0049(8) 0.0001(8) -0.0017(8) C13' 0.0295(11) 0.0316(10) 0.0257(10) 0.0034(8) -0.0027(8) 0.0030(8) C14' 0.0327(10) 0.0257(9) 0.0248(10) 0.0037(8) -0.0068(9) -0.0031(8) C15' 0.0349(11) 0.0228(9) 0.0264(10) 0.0036(8) 0.0010(9) -0.0019(8) C16' 0.0385(12) 0.0388(11) 0.0306(11) -0.0039(9) 0.0019(9) -0.0002(10) C17' 0.0464(14) 0.0542(13) 0.0279(11) -0.0100(10) -0.0034(10) -0.0023(11) O18' 0.0341(8) 0.0490(8) 0.0287(7) -0.0016(6) -0.0048(6) 0.0010(7) C19' 0.0319(11) 0.0231(9) 0.0323(11) 0.0078(8) 0.0032(9) -0.0029(8) O20' 0.0392(8) 0.0303(7) 0.0391(8) -0.0060(6) -0.0071(7) -0.0002(6) O21' 0.0274(7) 0.0466(8) 0.0360(8) -0.0009(6) 0.0022(6) 0.0024(6) C22' 0.0269(11) 0.0574(14) 0.0472(13) 0.0004(11) -0.0010(10) 0.0025(10) C23' 0.0271(11) 0.0337(10) 0.0295(10) 0.0008(8) -0.0052(8) 0.0044(8) C25' 0.0541(15) 0.0516(13) 0.0310(12) -0.0028(10) 0.0056(11) -0.0014(12) C24' 0.0480(13) 0.0370(11) 0.0392(12) -0.0057(9) -0.0053(11) -0.0047(10) O26' 0.0295(7) 0.0269(7) 0.0401(8) 0.0074(6) -0.0014(6) -0.0042(6) _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 O1 C2 1.342(2) . ? O1 C5 1.448(2) . ? C2 O26 1.195(2) . ? C2 N3 1.386(2) . ? N3 C9 1.394(2) . ? N3 C4 1.470(2) . ? C4 C6 1.524(3) . ? C4 C5 1.526(2) . ? C6 C8 1.525(3) . ? C6 C7 1.535(3) . ? C9 O10 1.210(2) . ? C9 C11 1.513(3) . ? C11 C23 1.519(3) . ? C11 C13 1.543(2) . ? C13 C14 1.486(2) . ? C14 C15 1.359(3) . ? C14 O18 1.364(2) . ? C15 C16 1.435(3) . ? C15 C19 1.458(3) . ? C16 C17 1.327(3) . ? C17 O18 1.372(2) . ? C19 O20 1.202(2) . ? C19 O21 1.339(2) . ? O21 C22 1.443(2) . ? C23 C24 1.320(3) . ? C23 C25 1.480(3) . ? O1' C2' 1.338(2) . ? O1' C5' 1.443(2) . ? C2' O26' 1.193(2) . ? C2' N3' 1.396(2) . ? N3' C9' 1.391(2) . ? N3' C4' 1.470(2) . ? C4' C5' 1.529(2) . ? C4' C6' 1.537(2) . ? C6' C8' 1.513(3) . ? C6' C7' 1.522(3) . ? C9' O10' 1.212(2) . ? C9' C11' 1.518(2) . ? C11' C23' 1.518(3) . ? C11' C13' 1.549(2) . ? C13' C14' 1.486(3) . ? C14' C15' 1.357(3) . ? C14' O18' 1.362(2) . ? C15' C16' 1.436(3) . ? C15' C19' 1.468(3) . ? C16' C17' 1.331(3) . ? C17' O18' 1.371(2) . ? C19' O20' 1.204(2) . ? C19' O21' 1.336(2) . ? O21' C22' 1.442(2) . ? C23' C24' 1.324(3) . ? C23' C25' 1.502(3) . ? 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 C2 O1 C5 110.41(13) . . ? O26 C2 O1 122.49(17) . . ? O26 C2 N3 128.65(17) . . ? O1 C2 N3 108.82(16) . . ? C2 N3 C9 127.26(15) . . ? C2 N3 C4 111.57(14) . . ? C9 N3 C4 121.11(14) . . ? N3 C4 C6 112.05(15) . . ? N3 C4 C5 100.54(14) . . ? C6 C4 C5 114.72(15) . . ? O1 C5 C4 105.22(14) . . ? C4 C6 C8 112.68(17) . . ? C4 C6 C7 110.38(17) . . ? C8 C6 C7 111.31(18) . . ? O10 C9 N3 118.23(17) . . ? O10 C9 C11 122.68(16) . . ? N3 C9 C11 119.06(16) . . ? C9 C11 C23 111.12(15) . . ? C9 C11 C13 110.85(15) . . ? C23 C11 C13 108.02(14) . . ? C14 C13 C11 116.15(15) . . ? C15 C14 O18 109.30(16) . . ? C15 C14 C13 132.86(17) . . ? O18 C14 C13 117.69(16) . . ? C14 C15 C16 106.70(17) . . ? C14 C15 C19 126.00(16) . . ? C16 C15 C19 127.22(17) . . ? C17 C16 C15 106.22(18) . . ? C16 C17 O18 110.99(18) . . ? C14 O18 C17 106.79(15) . . ? O20 C19 O21 123.10(18) . . ? O20 C19 C15 125.80(18) . . ? O21 C19 C15 111.09(15) . . ? C19 O21 C22 115.90(15) . . ? C24 C23 C25 123.39(19) . . ? C24 C23 C11 120.92(18) . . ? C25 C23 C11 115.49(17) . . ? C2' O1' C5' 111.08(13) . . ? O26' C2' O1' 122.37(16) . . ? O26' C2' N3' 128.96(17) . . ? O1' C2' N3' 108.65(15) . . ? C9' N3' C2' 127.26(15) . . ? C9' N3' C4' 120.16(14) . . ? C2' N3' C4' 111.48(14) . . ? N3' C4' C5' 101.20(14) . . ? N3' C4' C6' 112.87(14) . . ? C5' C4' C6' 115.03(15) . . ? O1' C5' C4' 105.44(14) . . ? C8' C6' C7' 112.06(16) . . ? C8' C6' C4' 112.74(15) . . ? C7' C6' C4' 109.93(15) . . ? O10' C9' N3' 118.32(16) . . ? O10' C9' C11' 122.45(16) . . ? N3' C9' C11' 119.23(15) . . ? C9' C11' C23' 110.58(14) . . ? C9' C11' C13' 108.84(14) . . ? C23' C11' C13' 109.99(14) . . ? C14' C13' C11' 114.19(14) . . ? C15' C14' O18' 109.29(16) . . ? C15' C14' C13' 133.71(17) . . ? O18' C14' C13' 116.97(16) . . ? C14' C15' C16' 106.94(17) . . ? C14' C15' C19' 125.43(16) . . ? C16' C15' C19' 127.54(18) . . ? C17' C16' C15' 105.87(19) . . ? C16' C17' O18' 111.00(18) . . ? C14' O18' C17' 106.89(15) . . ? O20' C19' O21' 123.25(18) . . ? O20' C19' C15' 124.91(18) . . ? O21' C19' C15' 111.83(16) . . ? C19' O21' C22' 114.75(15) . . ? C24' C23' C25' 121.85(19) . . ? C24' C23' C11' 120.40(18) . . ? C25' C23' C11' 117.70(16) . . ? _diffrn_measured_fraction_theta_max 0.922 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.15 _refine_diff_density_min -0.18 _refine_diff_density_rms 0.04