# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email ltpan@yahoo.cn loop_ _publ_author_name 'Juan Zou' 'Lu-Tai Pan' 'Qiji Li' 'Jian-Xin Pu' 'Ping Yao' 'Min Zhu' 'Jeffrey Banas' 'Hongjie Zhang' 'Han-Dong Sun' data_p _database_code_depnum_ccdc_archive 'CCDC 672260' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 O2' _chemical_formula_weight 302.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.8579(9) _cell_length_b 10.1629(11) _cell_length_c 11.0489(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.616(4) _cell_angle_gamma 90.00 _cell_volume 882.30(17) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 332 _exptl_absorpt_coefficient_mu 0.071 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _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 9317 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0193 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.84 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1634 _reflns_number_gt 1460 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _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^)+(0.0881P)^2^+0.1321P] 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 0.029(7) _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 10(10) _refine_ls_number_reflns 1634 _refine_ls_number_parameters 200 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0540 _refine_ls_R_factor_gt 0.0486 _refine_ls_wR_factor_ref 0.1358 _refine_ls_wR_factor_gt 0.1310 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 C1 C 0.6106(3) 0.1375(3) 0.5576(3) 0.0508(7) Uani 1 1 d . . . H1A H 0.6216 0.0632 0.5031 0.061 Uiso 1 1 calc R . . H1B H 0.6691 0.2115 0.5215 0.061 Uiso 1 1 calc R . . C2 C 0.6977(4) 0.1038(4) 0.6764(3) 0.0627(9) Uani 1 1 d . . . H2A H 0.6513 0.0224 0.7077 0.075 Uiso 1 1 calc R . . H2B H 0.8184 0.0911 0.6633 0.075 Uiso 1 1 calc R . . C3 C 0.6722(5) 0.2123(4) 0.7672(3) 0.0650(9) Uani 1 1 d . . . H3A H 0.7219 0.2926 0.7359 0.078 Uiso 1 1 calc R . . H3B H 0.7329 0.1898 0.8413 0.078 Uiso 1 1 calc R . . C4 C 0.4845(4) 0.2385(3) 0.7973(3) 0.0555(8) Uani 1 1 d . . . C5 C 0.3878(4) 0.2695(3) 0.6764(3) 0.0458(7) Uani 1 1 d . . . H5 H 0.4317 0.3548 0.6496 0.055 Uiso 1 1 calc R . . C6 C 0.1942(4) 0.2899(4) 0.6930(3) 0.0579(8) Uani 1 1 d . . . H6A H 0.1474 0.2132 0.7329 0.069 Uiso 1 1 calc R . . H6B H 0.1765 0.3651 0.7454 0.069 Uiso 1 1 calc R . . C7 C 0.0972(4) 0.3123(4) 0.5736(3) 0.0575(8) Uani 1 1 d . . . H7A H -0.0237 0.3008 0.5867 0.069 Uiso 1 1 calc R . . H7B H 0.1158 0.4018 0.5462 0.069 Uiso 1 1 calc R . . C8 C 0.1555(4) 0.2170(3) 0.4770(3) 0.0501(7) Uani 1 1 d . . . C9 C 0.3452(3) 0.2336(3) 0.4534(2) 0.0433(6) Uani 1 1 d . . . H9 H 0.3747 0.3272 0.4490 0.052 Uiso 1 1 calc R . . C10 C 0.4213(3) 0.1718(3) 0.5687(3) 0.0427(7) Uani 1 1 d . . . C11 C 0.3935(4) 0.1641(4) 0.3365(3) 0.0555(8) Uani 1 1 d . . . H11A H 0.3723 0.0705 0.3446 0.067 Uiso 1 1 calc R . . H11B H 0.5140 0.1763 0.3221 0.067 Uiso 1 1 calc R . . C12 C 0.2917(5) 0.2175(4) 0.2289(3) 0.0655(9) Uani 1 1 d . . . H12A H 0.3335 0.3046 0.2089 0.079 Uiso 1 1 calc R . . H12B H 0.3098 0.1612 0.1594 0.079 Uiso 1 1 calc R . . C13 C 0.1054(5) 0.2254(4) 0.2533(3) 0.0650(9) Uani 1 1 d . . . C14 C 0.0456(4) 0.2198(4) 0.3648(3) 0.0641(9) Uani 1 1 d . . . H14 H -0.0719 0.2175 0.3743 0.077 Uiso 1 1 calc R . . C15 C -0.0103(6) 0.2403(6) 0.1419(4) 0.0944(15) Uani 1 1 d . . . H15 H 0.0387 0.1817 0.0811 0.113 Uiso 1 1 calc R . . C16 C 0.0046(7) 0.3760(7) 0.0886(5) 0.115(2) Uani 1 1 d . . . H16A H 0.1225 0.3968 0.0772 0.172 Uiso 1 1 calc R . . H16B H -0.0449 0.4389 0.1427 0.172 Uiso 1 1 calc R . . H16C H -0.0541 0.3788 0.0121 0.172 Uiso 1 1 calc R . . C17 C -0.1803(8) 0.1975(8) 0.1541(7) 0.147(3) Uani 1 1 d . . . H17A H -0.2402 0.2094 0.0786 0.221 Uiso 1 1 calc R . . H17B H -0.2349 0.2480 0.2160 0.221 Uiso 1 1 calc R . . H17C H -0.1815 0.1061 0.1758 0.221 Uiso 1 1 calc R . . C18 C 0.4109(5) 0.1215(4) 0.8671(3) 0.0703(10) Uani 1 1 d . . . H18A H 0.4141 0.0442 0.8173 0.105 Uiso 1 1 calc R . . H18B H 0.2952 0.1401 0.8884 0.105 Uiso 1 1 calc R . . H18C H 0.4771 0.1070 0.9394 0.105 Uiso 1 1 calc R . . C19 C 0.4774(5) 0.3607(4) 0.8793(3) 0.0734(10) Uani 1 1 d . . . H19A H 0.5227 0.4351 0.8369 0.110 Uiso 1 1 calc R . . H19B H 0.5436 0.3452 0.9514 0.110 Uiso 1 1 calc R . . H19C H 0.3614 0.3780 0.9007 0.110 Uiso 1 1 calc R . . C20 C 0.3034(4) 0.0525(3) 0.5789(3) 0.0483(7) Uani 1 1 d . . . O1 O 0.3342(3) -0.0551(2) 0.6182(2) 0.0648(7) Uani 1 1 d . . . O2 O 0.1487(3) 0.0826(2) 0.5307(2) 0.0553(6) 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 C1 0.0437(14) 0.0480(17) 0.0608(18) 0.0000(14) 0.0058(13) 0.0011(13) C2 0.0520(16) 0.060(2) 0.076(2) 0.0052(18) -0.0070(15) 0.0094(15) C3 0.0640(19) 0.068(2) 0.063(2) 0.0076(18) -0.0175(16) -0.0054(17) C4 0.0683(19) 0.0498(18) 0.0482(16) 0.0030(14) -0.0039(14) -0.0041(15) C5 0.0509(15) 0.0382(15) 0.0484(16) 0.0012(12) 0.0020(12) -0.0026(12) C6 0.0564(17) 0.0577(19) 0.0597(18) -0.0053(16) 0.0107(14) 0.0058(16) C7 0.0435(14) 0.059(2) 0.071(2) 0.0003(16) 0.0087(14) 0.0064(14) C8 0.0426(14) 0.0466(17) 0.0609(18) 0.0024(14) -0.0017(13) -0.0031(13) C9 0.0434(14) 0.0383(14) 0.0481(15) 0.0004(12) 0.0015(12) -0.0012(12) C10 0.0407(14) 0.0367(15) 0.0506(16) 0.0036(12) 0.0044(11) -0.0005(11) C11 0.0567(17) 0.0556(18) 0.0544(18) -0.0020(15) 0.0078(14) 0.0001(15) C12 0.079(2) 0.064(2) 0.0529(18) -0.0025(17) -0.0045(16) -0.0049(18) C13 0.068(2) 0.063(2) 0.063(2) 0.0061(18) -0.0115(16) -0.0105(18) C14 0.0468(16) 0.066(2) 0.079(2) 0.0029(19) -0.0102(16) -0.0036(16) C15 0.088(3) 0.109(4) 0.085(3) 0.010(3) -0.033(2) -0.009(3) C16 0.112(4) 0.130(5) 0.101(4) 0.044(4) -0.031(3) -0.007(3) C17 0.142(5) 0.148(6) 0.150(5) 0.035(5) -0.085(5) -0.052(5) C18 0.085(2) 0.067(2) 0.058(2) 0.0148(18) 0.0006(17) -0.0035(19) C19 0.096(3) 0.068(2) 0.057(2) -0.0103(18) -0.0058(19) -0.004(2) C20 0.0525(16) 0.0399(16) 0.0526(17) 0.0004(13) 0.0049(13) -0.0053(13) O1 0.0736(15) 0.0388(13) 0.0820(16) 0.0056(12) 0.0049(12) -0.0042(11) O2 0.0483(11) 0.0477(13) 0.0698(14) 0.0047(10) -0.0009(10) -0.0119(9) _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 1.512(5) . ? C1 C10 1.534(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.505(5) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.539(5) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C18 1.534(5) . ? C4 C19 1.539(5) . ? C4 C5 1.562(4) . ? C5 C6 1.548(4) . ? C5 C10 1.573(4) . ? C5 H5 0.9800 . ? C6 C7 1.533(5) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.515(5) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 O2 1.490(4) . ? C8 C14 1.503(4) . ? C8 C9 1.526(4) . ? C9 C11 1.524(4) . ? C9 C10 1.536(4) . ? C9 H9 0.9800 . ? C10 C20 1.531(4) . ? C11 C12 1.525(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.494(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.325(5) . ? C13 C15 1.530(5) . ? C14 H14 0.9300 . ? C15 C17 1.413(8) . ? C15 C16 1.504(8) . ? C15 H15 0.9800 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 O1 1.201(4) . ? C20 O2 1.357(4) . ? 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 C1 C10 114.3(3) . . ? C2 C1 H1A 108.7 . . ? C10 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? C10 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 110.5(3) . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 113.9(3) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C18 C4 C19 108.2(3) . . ? C18 C4 C3 110.0(3) . . ? C19 C4 C3 107.9(3) . . ? C18 C4 C5 113.8(3) . . ? C19 C4 C5 108.7(3) . . ? C3 C4 C5 108.0(3) . . ? C6 C5 C4 113.3(2) . . ? C6 C5 C10 110.3(2) . . ? C4 C5 C10 115.8(2) . . ? C6 C5 H5 105.5 . . ? C4 C5 H5 105.5 . . ? C10 C5 H5 105.5 . . ? C7 C6 C5 113.4(2) . . ? C7 C6 H6A 108.9 . . ? C5 C6 H6A 108.9 . . ? C7 C6 H6B 108.9 . . ? C5 C6 H6B 108.9 . . ? H6A C6 H6B 107.7 . . ? C8 C7 C6 111.1(3) . . ? C8 C7 H7A 109.4 . . ? C6 C7 H7A 109.4 . . ? C8 C7 H7B 109.4 . . ? C6 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? O2 C8 C14 108.8(3) . . ? O2 C8 C7 107.0(2) . . ? C14 C8 C7 113.1(3) . . ? O2 C8 C9 102.0(2) . . ? C14 C8 C9 114.3(3) . . ? C7 C8 C9 110.7(2) . . ? C11 C9 C8 110.3(2) . . ? C11 C9 C10 114.6(2) . . ? C8 C9 C10 100.7(2) . . ? C11 C9 H9 110.3 . . ? C8 C9 H9 110.3 . . ? C10 C9 H9 110.3 . . ? C20 C10 C1 114.4(2) . . ? C20 C10 C9 98.9(2) . . ? C1 C10 C9 113.3(2) . . ? C20 C10 C5 109.7(2) . . ? C1 C10 C5 112.0(2) . . ? C9 C10 C5 107.6(2) . . ? C9 C11 C12 111.2(3) . . ? C9 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C9 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C13 C12 C11 112.6(3) . . ? C13 C12 H12A 109.1 . . ? C11 C12 H12A 109.1 . . ? C13 C12 H12B 109.1 . . ? C11 C12 H12B 109.1 . . ? H12A C12 H12B 107.8 . . ? C14 C13 C12 121.6(3) . . ? C14 C13 C15 122.6(4) . . ? C12 C13 C15 115.8(3) . . ? C13 C14 C8 124.1(3) . . ? C13 C14 H14 117.9 . . ? C8 C14 H14 117.9 . . ? C17 C15 C16 113.4(5) . . ? C17 C15 C13 116.6(4) . . ? C16 C15 C13 110.9(4) . . ? C17 C15 H15 104.9 . . ? C16 C15 H15 104.9 . . ? C13 C15 H15 104.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? 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 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 C20 O2 121.6(3) . . ? O1 C20 C10 128.9(3) . . ? O2 C20 C10 109.4(2) . . ? C20 O2 C8 109.1(2) . . ? 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 C10 C1 C2 C3 -54.1(4) . . . . ? C1 C2 C3 C4 60.7(4) . . . . ? C2 C3 C4 C18 68.3(4) . . . . ? C2 C3 C4 C19 -173.8(3) . . . . ? C2 C3 C4 C5 -56.5(4) . . . . ? C18 C4 C5 C6 54.2(4) . . . . ? C19 C4 C5 C6 -66.5(3) . . . . ? C3 C4 C5 C6 176.7(3) . . . . ? C18 C4 C5 C10 -74.7(3) . . . . ? C19 C4 C5 C10 164.6(3) . . . . ? C3 C4 C5 C10 47.8(3) . . . . ? C4 C5 C6 C7 -176.6(3) . . . . ? C10 C5 C6 C7 -45.0(4) . . . . ? C5 C6 C7 C8 43.9(4) . . . . ? C6 C7 C8 O2 50.7(3) . . . . ? C6 C7 C8 C14 170.6(3) . . . . ? C6 C7 C8 C9 -59.7(3) . . . . ? O2 C8 C9 C11 80.6(3) . . . . ? C14 C8 C9 C11 -36.6(4) . . . . ? C7 C8 C9 C11 -165.8(3) . . . . ? O2 C8 C9 C10 -40.7(3) . . . . ? C14 C8 C9 C10 -158.0(3) . . . . ? C7 C8 C9 C10 72.9(3) . . . . ? C2 C1 C10 C20 -79.9(3) . . . . ? C2 C1 C10 C9 167.7(3) . . . . ? C2 C1 C10 C5 45.7(4) . . . . ? C11 C9 C10 C20 -76.3(3) . . . . ? C8 C9 C10 C20 42.0(3) . . . . ? C11 C9 C10 C1 45.2(3) . . . . ? C8 C9 C10 C1 163.5(2) . . . . ? C11 C9 C10 C5 169.6(2) . . . . ? C8 C9 C10 C5 -72.1(3) . . . . ? C6 C5 C10 C20 -45.8(3) . . . . ? C4 C5 C10 C20 84.5(3) . . . . ? C6 C5 C10 C1 -174.0(3) . . . . ? C4 C5 C10 C1 -43.7(3) . . . . ? C6 C5 C10 C9 60.9(3) . . . . ? C4 C5 C10 C9 -168.8(2) . . . . ? C8 C9 C11 C12 58.4(3) . . . . ? C10 C9 C11 C12 171.1(3) . . . . ? C9 C11 C12 C13 -48.4(4) . . . . ? C11 C12 C13 C14 16.6(6) . . . . ? C11 C12 C13 C15 -163.5(4) . . . . ? C12 C13 C14 C8 5.5(6) . . . . ? C15 C13 C14 C8 -174.5(4) . . . . ? O2 C8 C14 C13 -108.1(4) . . . . ? C7 C8 C14 C13 133.1(4) . . . . ? C9 C8 C14 C13 5.2(5) . . . . ? C14 C13 C15 C17 -24.0(8) . . . . ? C12 C13 C15 C17 156.0(6) . . . . ? C14 C13 C15 C16 107.8(6) . . . . ? C12 C13 C15 C16 -72.1(6) . . . . ? C1 C10 C20 O1 27.1(5) . . . . ? C9 C10 C20 O1 147.8(3) . . . . ? C5 C10 C20 O1 -99.8(4) . . . . ? C1 C10 C20 O2 -150.5(3) . . . . ? C9 C10 C20 O2 -29.8(3) . . . . ? C5 C10 C20 O2 82.6(3) . . . . ? O1 C20 O2 C8 -173.4(3) . . . . ? C10 C20 O2 C8 4.4(3) . . . . ? C14 C8 O2 C20 144.4(3) . . . . ? C7 C8 O2 C20 -93.0(3) . . . . ? C9 C8 O2 C20 23.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.357 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.044 data_cu_scr_8_0m _database_code_depnum_ccdc_archive 'CCDC 819348' #TrackingRef 'ltpan.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H30 O4' _chemical_formula_sum 'C20 H30 O4' _chemical_formula_weight 334.44 _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' 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 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.62460(10) _cell_length_b 16.0121(2) _cell_length_c 16.5233(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1752.69(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 9234 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 67.84 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.267 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.692 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details none _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 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10563 _diffrn_reflns_av_R_equivalents 0.0348 _diffrn_reflns_av_sigmaI/netI 0.0306 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.84 _diffrn_reflns_theta_max 68.09 _reflns_number_total 2928 _reflns_number_gt 2885 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0611P)^2^+0.1694P] 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 SHELXL _refine_ls_extinction_coef 0.0031(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 0.03(17) _refine_ls_number_reflns 2928 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0335 _refine_ls_wR_factor_ref 0.0952 _refine_ls_wR_factor_gt 0.0948 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 O2 O 0.20225(17) 0.96190(6) 0.61600(6) 0.0393(3) Uani 1 1 d . . . O4 O 0.3032(2) 1.09395(7) 0.62908(8) 0.0584(4) Uani 1 1 d . . . O1 O 0.2904(2) 0.81264(6) 0.45049(6) 0.0447(3) Uani 1 1 d . . . H1 H 0.2283 0.7690 0.4581 0.067 Uiso 1 1 calc R . . O3 O 0.62317(16) 0.84760(6) 0.52878(6) 0.0365(3) Uani 1 1 d . . . H3 H 0.5491 0.8291 0.4933 0.055 Uiso 1 1 calc R . . C16 C 0.3910(3) 0.62336(11) 0.70293(11) 0.0557(5) Uani 1 1 d . . . H16A H 0.3557 0.5751 0.7344 0.084 Uiso 1 1 calc R . . H16B H 0.5341 0.6324 0.7059 0.084 Uiso 1 1 calc R . . H16C H 0.3525 0.6146 0.6476 0.084 Uiso 1 1 calc R . . C15 C 0.2807(3) 0.69983(10) 0.73620(8) 0.0401(4) Uani 1 1 d . . . H15 H 0.3292 0.7087 0.7916 0.048 Uiso 1 1 calc R . . C13 C 0.3415(2) 0.77598(9) 0.68706(8) 0.0357(3) Uani 1 1 d . . . C12 C 0.5538(3) 0.80645(10) 0.70031(9) 0.0425(4) Uani 1 1 d . . . H12A H 0.6467 0.7666 0.6764 0.051 Uiso 1 1 calc R . . H12B H 0.5803 0.8080 0.7580 0.051 Uiso 1 1 calc R . . C11 C 0.5965(2) 0.89225(10) 0.66508(9) 0.0388(3) Uani 1 1 d . . . H11A H 0.7413 0.9012 0.6634 0.047 Uiso 1 1 calc R . . H11B H 0.5383 0.9345 0.7001 0.047 Uiso 1 1 calc R . . C9 C 0.5107(2) 0.90221(8) 0.58015(8) 0.0316(3) Uani 1 1 d . . . C10 C 0.5083(2) 0.99468(8) 0.55056(8) 0.0337(3) Uani 1 1 d . . . C1 C 0.7079(3) 1.03981(10) 0.56572(10) 0.0444(4) Uani 1 1 d . . . H1A H 0.7228 1.0489 0.6235 0.053 Uiso 1 1 calc R . . H1B H 0.8176 1.0039 0.5484 0.053 Uiso 1 1 calc R . . C2 C 0.7276(3) 1.12337(11) 0.52264(12) 0.0562(5) Uani 1 1 d . . . H2A H 0.6326 1.1628 0.5457 0.067 Uiso 1 1 calc R . . H2B H 0.8627 1.1453 0.5305 0.067 Uiso 1 1 calc R . . C3 C 0.6865(3) 1.11371(11) 0.43269(11) 0.0524(4) Uani 1 1 d . . . H3A H 0.7859 1.0760 0.4098 0.063 Uiso 1 1 calc R . . H3B H 0.7031 1.1676 0.4067 0.063 Uiso 1 1 calc R . . C17 C 0.0561(3) 0.68387(12) 0.74130(11) 0.0515(4) Uani 1 1 d . . . H17A H -0.0103 0.7327 0.7620 0.077 Uiso 1 1 calc R . . H17B H 0.0313 0.6375 0.7768 0.077 Uiso 1 1 calc R . . H17C H 0.0048 0.6712 0.6884 0.077 Uiso 1 1 calc R . . C14 C 0.2196(2) 0.81259(9) 0.63326(8) 0.0351(3) Uani 1 1 d . . . H14 H 0.0886 0.7925 0.6280 0.042 Uiso 1 1 calc R . . C8 C 0.2830(2) 0.88408(9) 0.58112(8) 0.0327(3) Uani 1 1 d . . . C20 C 0.3342(3) 1.02593(9) 0.60184(9) 0.0394(4) Uani 1 1 d . . . C5 C 0.4459(2) 0.99581(8) 0.45932(9) 0.0346(3) Uani 1 1 d . . . H5 H 0.5361 0.9560 0.4325 0.042 Uiso 1 1 calc R . . C4 C 0.4754(3) 1.08031(9) 0.41362(10) 0.0438(4) Uani 1 1 d . . . C18 C 0.4632(4) 1.06358(12) 0.32261(11) 0.0595(5) Uani 1 1 d . . . H18A H 0.5013 1.1130 0.2935 0.089 Uiso 1 1 calc R . . H18B H 0.3275 1.0484 0.3085 0.089 Uiso 1 1 calc R . . H18C H 0.5531 1.0188 0.3087 0.089 Uiso 1 1 calc R . . C19 C 0.3160(3) 1.14661(11) 0.43520(14) 0.0594(5) Uani 1 1 d . . . H19A H 0.3485 1.1982 0.4087 0.089 Uiso 1 1 calc R . . H19B H 0.3145 1.1551 0.4927 0.089 Uiso 1 1 calc R . . H19C H 0.1854 1.1279 0.4177 0.089 Uiso 1 1 calc R . . C6 C 0.2327(3) 0.96017(10) 0.44880(10) 0.0423(4) Uani 1 1 d . . . H6A H 0.1358 1.0016 0.4668 0.051 Uiso 1 1 calc R . . H6B H 0.2089 0.9503 0.3917 0.051 Uiso 1 1 calc R . . C7 C 0.1949(3) 0.87936(9) 0.49468(9) 0.0371(3) Uani 1 1 d . . . H7 H 0.0494 0.8690 0.4977 0.045 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 O2 0.0346(6) 0.0358(5) 0.0475(6) 0.0001(4) 0.0072(5) 0.0047(4) O4 0.0682(9) 0.0385(6) 0.0686(8) -0.0145(5) 0.0198(7) 0.0062(6) O1 0.0584(7) 0.0364(5) 0.0394(5) -0.0029(4) -0.0012(5) -0.0155(5) O3 0.0356(6) 0.0315(5) 0.0423(6) -0.0028(4) 0.0026(4) 0.0057(4) C16 0.0638(12) 0.0429(9) 0.0604(10) 0.0102(8) 0.0100(9) 0.0079(8) C15 0.0472(9) 0.0411(8) 0.0322(7) 0.0050(6) 0.0011(6) 0.0028(7) C13 0.0384(9) 0.0378(7) 0.0308(7) -0.0009(6) 0.0031(6) 0.0035(6) C12 0.0430(9) 0.0486(9) 0.0359(7) 0.0046(6) -0.0067(6) 0.0053(7) C11 0.0327(8) 0.0425(8) 0.0410(8) -0.0029(6) -0.0060(6) -0.0016(6) C9 0.0295(8) 0.0303(7) 0.0349(7) -0.0029(5) -0.0002(5) 0.0009(6) C10 0.0314(8) 0.0295(7) 0.0401(7) -0.0038(5) 0.0003(6) 0.0003(5) C1 0.0378(9) 0.0418(8) 0.0536(9) -0.0055(7) -0.0015(7) -0.0079(7) C2 0.0547(12) 0.0410(9) 0.0730(11) -0.0040(8) 0.0015(9) -0.0165(8) C3 0.0525(11) 0.0397(8) 0.0651(11) 0.0073(8) 0.0121(9) -0.0096(8) C17 0.0529(11) 0.0483(10) 0.0532(9) 0.0113(7) 0.0080(8) -0.0002(8) C14 0.0319(8) 0.0370(7) 0.0365(7) 0.0011(6) 0.0020(6) -0.0019(6) C8 0.0305(7) 0.0310(7) 0.0368(7) 0.0000(5) -0.0006(6) 0.0019(6) C20 0.0419(10) 0.0339(7) 0.0424(8) -0.0039(6) 0.0036(6) 0.0042(6) C5 0.0379(8) 0.0271(7) 0.0389(7) 0.0007(5) 0.0018(6) 0.0011(6) C4 0.0494(10) 0.0303(7) 0.0517(9) 0.0068(6) 0.0057(7) 0.0018(7) C18 0.0796(14) 0.0465(10) 0.0525(9) 0.0158(8) 0.0047(9) -0.0037(9) C19 0.0616(12) 0.0370(8) 0.0796(12) 0.0147(8) 0.0089(10) 0.0103(8) C6 0.0433(10) 0.0392(8) 0.0442(8) 0.0093(6) -0.0096(7) -0.0035(7) C7 0.0318(8) 0.0385(7) 0.0410(8) 0.0050(6) -0.0065(6) -0.0057(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 O2 C20 1.3674(19) . ? O2 C8 1.4734(17) . ? O4 C20 1.1963(19) . ? O1 C7 1.4402(19) . ? O1 H1 0.8200 . ? O3 C9 1.4285(16) . ? O3 H3 0.8200 . ? C16 C15 1.528(2) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C15 C17 1.512(3) . ? C15 C13 1.519(2) . ? C15 H15 0.9800 . ? C13 C14 1.336(2) . ? C13 C12 1.505(2) . ? C12 C11 1.519(2) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C11 C9 1.522(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C9 C8 1.536(2) . ? C9 C10 1.5593(19) . ? C10 C20 1.516(2) . ? C10 C1 1.528(2) . ? C10 C5 1.563(2) . ? C1 C2 1.521(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.519(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.530(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C14 C8 1.493(2) . ? C14 H14 0.9300 . ? C8 C7 1.545(2) . ? C5 C6 1.534(2) . ? C5 C4 1.5617(19) . ? C5 H5 0.9800 . ? C4 C18 1.530(2) . ? C4 C19 1.540(2) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C6 C7 1.520(2) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7 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 C20 O2 C8 109.58(11) . . ? C7 O1 H1 109.5 . . ? C9 O3 H3 109.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C17 C15 C13 115.23(14) . . ? C17 C15 C16 110.80(16) . . ? C13 C15 C16 108.91(13) . . ? C17 C15 H15 107.2 . . ? C13 C15 H15 107.2 . . ? C16 C15 H15 107.2 . . ? C14 C13 C12 121.27(14) . . ? C14 C13 C15 123.20(15) . . ? C12 C13 C15 115.48(13) . . ? C13 C12 C11 114.30(13) . . ? C13 C12 H12A 108.7 . . ? C11 C12 H12A 108.7 . . ? C13 C12 H12B 108.7 . . ? C11 C12 H12B 108.7 . . ? H12A C12 H12B 107.6 . . ? C12 C11 C9 112.25(12) . . ? C12 C11 H11A 109.2 . . ? C9 C11 H11A 109.2 . . ? C12 C11 H11B 109.2 . . ? C9 C11 H11B 109.2 . . ? H11A C11 H11B 107.9 . . ? O3 C9 C11 106.78(12) . . ? O3 C9 C8 113.75(11) . . ? C11 C9 C8 109.71(12) . . ? O3 C9 C10 113.60(11) . . ? C11 C9 C10 113.10(11) . . ? C8 C9 C10 99.94(11) . . ? C20 C10 C1 114.26(12) . . ? C20 C10 C9 98.40(11) . . ? C1 C10 C9 112.87(12) . . ? C20 C10 C5 109.53(12) . . ? C1 C10 C5 112.40(13) . . ? C9 C10 C5 108.43(11) . . ? C2 C1 C10 114.42(14) . . ? C2 C1 H1A 108.7 . . ? C10 C1 H1A 108.7 . . ? C2 C1 H1B 108.7 . . ? C10 C1 H1B 108.7 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 110.67(14) . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2B 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 108.1 . . ? C2 C3 C4 113.64(15) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? 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 . . ? C13 C14 C8 123.41(15) . . ? C13 C14 H14 118.3 . . ? C8 C14 H14 118.3 . . ? O2 C8 C14 108.70(11) . . ? O2 C8 C9 101.58(11) . . ? C14 C8 C9 115.27(12) . . ? O2 C8 C7 105.43(11) . . ? C14 C8 C7 112.95(12) . . ? C9 C8 C7 111.74(12) . . ? O4 C20 O2 120.55(15) . . ? O4 C20 C10 129.91(15) . . ? O2 C20 C10 109.54(12) . . ? C6 C5 C4 112.51(13) . . ? C6 C5 C10 110.38(12) . . ? C4 C5 C10 116.31(12) . . ? C6 C5 H5 105.6 . . ? C4 C5 H5 105.6 . . ? C10 C5 H5 105.6 . . ? C18 C4 C3 108.19(16) . . ? C18 C4 C19 108.19(16) . . ? C3 C4 C19 109.79(15) . . ? C18 C4 C5 108.48(13) . . ? C3 C4 C5 108.52(14) . . ? C19 C4 C5 113.55(14) . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C7 C6 C5 114.30(12) . . ? C7 C6 H6A 108.7 . . ? C5 C6 H6A 108.7 . . ? C7 C6 H6B 108.7 . . ? C5 C6 H6B 108.7 . . ? H6A C6 H6B 107.6 . . ? O1 C7 C6 107.84(12) . . ? O1 C7 C8 109.84(12) . . ? C6 C7 C8 110.94(12) . . ? O1 C7 H7 109.4 . . ? C6 C7 H7 109.4 . . ? C8 C7 H7 109.4 . . ? 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 C17 C15 C13 C14 -18.8(2) . . . . ? C16 C15 C13 C14 106.41(18) . . . . ? C17 C15 C13 C12 163.54(14) . . . . ? C16 C15 C13 C12 -71.27(17) . . . . ? C14 C13 C12 C11 14.8(2) . . . . ? C15 C13 C12 C11 -167.49(12) . . . . ? C13 C12 C11 C9 -44.18(17) . . . . ? C12 C11 C9 O3 -67.56(15) . . . . ? C12 C11 C9 C8 56.15(16) . . . . ? C12 C11 C9 C10 166.76(12) . . . . ? O3 C9 C10 C20 164.26(12) . . . . ? C11 C9 C10 C20 -73.80(15) . . . . ? C8 C9 C10 C20 42.75(13) . . . . ? O3 C9 C10 C1 -74.87(15) . . . . ? C11 C9 C10 C1 47.07(16) . . . . ? C8 C9 C10 C1 163.62(12) . . . . ? O3 C9 C10 C5 50.34(16) . . . . ? C11 C9 C10 C5 172.28(12) . . . . ? C8 C9 C10 C5 -71.17(13) . . . . ? C20 C10 C1 C2 -80.74(19) . . . . ? C9 C10 C1 C2 167.91(13) . . . . ? C5 C10 C1 C2 44.88(18) . . . . ? C10 C1 C2 C3 -53.3(2) . . . . ? C1 C2 C3 C4 59.8(2) . . . . ? C12 C13 C14 C8 1.5(2) . . . . ? C15 C13 C14 C8 -176.03(13) . . . . ? C20 O2 C8 C14 146.70(13) . . . . ? C20 O2 C8 C9 24.73(14) . . . . ? C20 O2 C8 C7 -91.94(14) . . . . ? C13 C14 C8 O2 -101.20(16) . . . . ? C13 C14 C8 C9 12.0(2) . . . . ? C13 C14 C8 C7 142.16(15) . . . . ? O3 C9 C8 O2 -163.26(10) . . . . ? C11 C9 C8 O2 77.21(13) . . . . ? C10 C9 C8 O2 -41.85(12) . . . . ? O3 C9 C8 C14 79.43(15) . . . . ? C11 C9 C8 C14 -40.09(16) . . . . ? C10 C9 C8 C14 -159.15(11) . . . . ? O3 C9 C8 C7 -51.30(15) . . . . ? C11 C9 C8 C7 -170.82(11) . . . . ? C10 C9 C8 C7 70.11(13) . . . . ? C8 O2 C20 O4 -175.80(15) . . . . ? C8 O2 C20 C10 3.81(16) . . . . ? C1 C10 C20 O4 29.8(2) . . . . ? C9 C10 C20 O4 149.61(18) . . . . ? C5 C10 C20 O4 -97.3(2) . . . . ? C1 C10 C20 O2 -149.79(13) . . . . ? C9 C10 C20 O2 -29.95(15) . . . . ? C5 C10 C20 O2 83.09(15) . . . . ? C20 C10 C5 C6 -44.41(15) . . . . ? C1 C10 C5 C6 -172.57(12) . . . . ? C9 C10 C5 C6 61.94(15) . . . . ? C20 C10 C5 C4 85.33(16) . . . . ? C1 C10 C5 C4 -42.83(18) . . . . ? C9 C10 C5 C4 -168.32(12) . . . . ? C2 C3 C4 C18 -173.19(15) . . . . ? C2 C3 C4 C19 68.95(19) . . . . ? C2 C3 C4 C5 -55.68(18) . . . . ? C6 C5 C4 C18 -66.69(19) . . . . ? C10 C5 C4 C18 164.59(15) . . . . ? C6 C5 C4 C3 175.99(13) . . . . ? C10 C5 C4 C3 47.27(18) . . . . ? C6 C5 C4 C19 53.62(19) . . . . ? C10 C5 C4 C19 -75.1(2) . . . . ? C4 C5 C6 C7 -178.00(13) . . . . ? C10 C5 C6 C7 -46.25(17) . . . . ? C5 C6 C7 O1 -76.87(16) . . . . ? C5 C6 C7 C8 43.45(18) . . . . ? O2 C8 C7 O1 170.65(11) . . . . ? C14 C8 C7 O1 -70.79(17) . . . . ? C9 C8 C7 O1 61.13(15) . . . . ? O2 C8 C7 C6 51.53(16) . . . . ? C14 C8 C7 C6 170.09(13) . . . . ? C9 C8 C7 C6 -57.99(17) . . . . ? 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 O3 H3 O1 0.82 1.87 2.6166(16) 150.3 . O1 H1 O3 0.82 2.01 2.8156(14) 169.7 2_466 _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 68.09 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.159 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.039