# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Yuanchao Li' _publ_contact_author_email ycli@mail.shcnc.ac.cn loop_ _publ_author_name 'Bing Zhou' 'Xiaomei Li' 'Huanyu Tang' 'Huijin Feng' 'Yuanchao Li' data_cd201557 _database_code_depnum_ccdc_archive 'CCDC 800757' #TrackingRef '3131_web_deposit_cif_file_0_BingZhou_1289543588.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H26 O3' _chemical_formula_weight 326.42 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 Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.5128(8) _cell_length_b 7.9036(7) _cell_length_c 12.3434(10) _cell_angle_alpha 90.00 _cell_angle_beta 109.5520(10) _cell_angle_gamma 90.00 _cell_volume 874.53(13) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3350 _cell_measurement_theta_min 4.718 _cell_measurement_theta_max 56.153 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.395 _exptl_crystal_size_mid 0.321 _exptl_crystal_size_min 0.269 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4131 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5161 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2038 _reflns_number_gt 1903 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1029P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 2038 _refine_ls_number_parameters 221 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0472 _refine_ls_wR_factor_ref 0.1314 _refine_ls_wR_factor_gt 0.1288 _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 0.3863(3) -0.1653(3) 0.5562(2) 0.0729(6) Uani 1 1 d . . . O2 O 0.3339(2) -0.0268(3) 0.39075(16) 0.0693(6) Uani 1 1 d . . . O3 O 0.29616(17) 0.2219(2) 1.05855(13) 0.0484(4) Uani 1 1 d . . . C1 C 0.2618(2) 0.4669(3) 0.58151(18) 0.0454(5) Uani 1 1 d . . . H1A H 0.3675 0.4844 0.6214 0.054 Uiso 1 1 calc R . . H1B H 0.2110 0.5733 0.5815 0.054 Uiso 1 1 calc R . . C2 C 0.2375(3) 0.4135(4) 0.4563(2) 0.0568(6) Uani 1 1 d . . . H2A H 0.1347 0.4345 0.4093 0.068 Uiso 1 1 calc R . . H2B H 0.3011 0.4806 0.4259 0.068 Uiso 1 1 calc R . . C3 C 0.2723(3) 0.2317(4) 0.45080(19) 0.0501(5) Uani 1 1 d . . . C4 C 0.2996(2) 0.1248(3) 0.53813(18) 0.0434(5) Uani 1 1 d . . . C5 C 0.2975(2) 0.1721(3) 0.65522(17) 0.0374(4) Uani 1 1 d . . . H5 H 0.4001 0.2027 0.7008 0.045 Uiso 1 1 calc R . . C6 C 0.2504(3) 0.0346(3) 0.72228(19) 0.0446(5) Uani 1 1 d . . . H6A H 0.3013 -0.0705 0.7187 0.053 Uiso 1 1 calc R . . H6B H 0.1437 0.0155 0.6899 0.053 Uiso 1 1 calc R . . C7 C 0.2918(3) 0.0942(3) 0.84673(18) 0.0440(5) Uani 1 1 d . . . H7A H 0.2385 0.0254 0.8853 0.053 Uiso 1 1 calc R . . H7B H 0.3976 0.0753 0.8850 0.053 Uiso 1 1 calc R . . C8 C 0.2580(2) 0.2778(2) 0.86026(17) 0.0366(4) Uani 1 1 d . . . C9 C 0.2173(2) 0.3912(2) 0.76761(16) 0.0356(4) Uani 1 1 d . . . C10 C 0.2031(2) 0.3331(3) 0.64629(15) 0.0360(4) Uani 1 1 d . . . C11 C 0.1800(2) 0.5556(3) 0.78675(19) 0.0440(5) Uani 1 1 d . . . H11 H 0.1513 0.6313 0.7256 0.053 Uiso 1 1 calc R . . C12 C 0.1845(3) 0.6098(3) 0.89451(19) 0.0483(5) Uani 1 1 d . . . H12 H 0.1581 0.7207 0.9043 0.058 Uiso 1 1 calc R . . C13 C 0.2278(2) 0.5013(3) 0.98806(19) 0.0433(5) Uani 1 1 d . . . C14 C 0.2628(2) 0.3362(3) 0.96863(17) 0.0392(4) Uani 1 1 d . . . C15 C 0.2309(3) 0.5595(4) 1.1064(2) 0.0544(6) Uani 1 1 d . . . H15 H 0.3084 0.4933 1.1630 0.065 Uiso 1 1 calc R . . C16 C 0.2725(5) 0.7438(5) 1.1299(3) 0.0827(10) Uani 1 1 d . . . H16A H 0.3584 0.7683 1.1084 0.124 Uiso 1 1 calc R . . H16B H 0.2949 0.7667 1.2103 0.124 Uiso 1 1 calc R . . H16C H 0.1906 0.8135 1.0860 0.124 Uiso 1 1 calc R . . C17 C 0.0846(4) 0.5164(7) 1.1226(3) 0.0885(12) Uani 1 1 d . . . H17A H 0.0877 0.5507 1.1980 0.133 Uiso 1 1 calc R . . H17B H 0.0681 0.3965 1.1144 0.133 Uiso 1 1 calc R . . H17C H 0.0048 0.5744 1.0658 0.133 Uiso 1 1 calc R . . C18 C 0.2890(4) 0.1423(5) 0.3496(2) 0.0674(7) Uani 1 1 d . . . H18A H 0.1954 0.1409 0.2861 0.081 Uiso 1 1 calc R . . H18B H 0.3645 0.1963 0.3246 0.081 Uiso 1 1 calc R . . C19 C 0.3439(3) -0.0389(4) 0.5032(2) 0.0536(6) Uani 1 1 d . . . C20 C 0.0357(2) 0.3026(3) 0.58140(19) 0.0485(5) Uani 1 1 d . . . H20A H -0.0056 0.2352 0.6281 0.073 Uiso 1 1 calc R . . H20B H 0.0239 0.2444 0.5106 0.073 Uiso 1 1 calc R . . H20C H -0.0153 0.4093 0.5651 0.073 Uiso 1 1 calc R . . C21 C 0.4513(3) 0.1885(4) 1.1121(2) 0.0567(6) Uani 1 1 d . . . H21A H 0.4999 0.1923 1.0554 0.085 Uiso 1 1 calc R . . H21B H 0.4642 0.0784 1.1468 0.085 Uiso 1 1 calc R . . H21C H 0.4941 0.2723 1.1700 0.085 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 O1 0.0986(14) 0.0460(11) 0.0865(14) -0.0048(10) 0.0477(12) 0.0127(11) O2 0.0876(13) 0.0692(13) 0.0617(10) -0.0210(11) 0.0393(10) -0.0022(11) O3 0.0531(8) 0.0523(9) 0.0436(8) 0.0116(7) 0.0211(6) 0.0051(7) C1 0.0579(12) 0.0372(10) 0.0418(10) 0.0076(9) 0.0178(9) 0.0018(10) C2 0.0755(15) 0.0552(14) 0.0434(11) 0.0092(11) 0.0247(11) 0.0068(12) C3 0.0552(11) 0.0562(14) 0.0410(10) -0.0019(11) 0.0187(9) 0.0010(11) C4 0.0448(9) 0.0431(11) 0.0443(11) -0.0068(10) 0.0174(8) -0.0009(9) C5 0.0424(8) 0.0328(9) 0.0366(9) -0.0010(8) 0.0127(7) 0.0015(8) C6 0.0578(11) 0.0287(9) 0.0487(11) 0.0013(9) 0.0198(9) 0.0020(9) C7 0.0630(12) 0.0318(10) 0.0421(10) 0.0069(8) 0.0241(9) 0.0064(9) C8 0.0399(8) 0.0319(9) 0.0397(9) 0.0009(8) 0.0154(7) 0.0015(7) C9 0.0385(9) 0.0314(9) 0.0368(9) 0.0016(8) 0.0124(7) 0.0016(8) C10 0.0413(9) 0.0307(9) 0.0352(9) 0.0008(7) 0.0121(7) 0.0020(8) C11 0.0567(11) 0.0314(10) 0.0429(11) 0.0060(9) 0.0155(9) 0.0076(9) C12 0.0578(11) 0.0361(11) 0.0514(12) -0.0043(10) 0.0190(9) 0.0058(9) C13 0.0431(9) 0.0443(12) 0.0432(10) -0.0093(9) 0.0153(8) -0.0013(9) C14 0.0380(8) 0.0420(11) 0.0394(9) 0.0020(8) 0.0153(7) -0.0002(8) C15 0.0599(12) 0.0621(15) 0.0412(11) -0.0105(11) 0.0167(9) 0.0068(12) C16 0.110(2) 0.0699(19) 0.0644(17) -0.0279(16) 0.0241(17) -0.001(2) C17 0.0805(18) 0.134(4) 0.0661(16) -0.017(2) 0.0443(15) -0.008(2) C18 0.0845(17) 0.0754(19) 0.0479(12) -0.0082(14) 0.0298(12) 0.0005(17) C19 0.0563(13) 0.0514(14) 0.0601(13) -0.0140(13) 0.0287(11) -0.0038(11) C20 0.0433(10) 0.0518(12) 0.0466(10) -0.0035(10) 0.0098(8) 0.0018(9) C21 0.0570(11) 0.0638(16) 0.0430(10) 0.0092(11) 0.0083(9) 0.0089(12) _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 C19 1.189(4) . ? O2 C19 1.363(3) . ? O2 C18 1.443(5) . ? O3 C14 1.383(3) . ? O3 C21 1.425(3) . ? C1 C10 1.539(3) . ? C1 C2 1.543(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.481(4) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.325(3) . ? C3 C18 1.489(3) . ? C4 C19 1.469(3) . ? C4 C5 1.499(3) . ? C5 C6 1.522(3) . ? C5 C10 1.539(3) . ? C5 H5 0.9800 . ? C6 C7 1.527(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.508(3) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C14 1.401(3) . ? C8 C9 1.402(3) . ? C9 C11 1.388(3) . ? C9 C10 1.529(3) . ? C10 C20 1.543(3) . ? C11 C12 1.384(3) . ? C11 H11 0.9300 . ? C12 C13 1.386(3) . ? C12 H12 0.9300 . ? C13 C14 1.387(3) . ? C13 C15 1.523(3) . ? C15 C17 1.510(4) . ? C15 C16 1.512(5) . ? 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 0.9700 . ? C18 H18B 0.9700 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 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 C19 O2 C18 109.5(2) . . ? C14 O3 C21 114.63(17) . . ? C10 C1 C2 111.9(2) . . ? C10 C1 H1A 109.2 . . ? C2 C1 H1A 109.2 . . ? C10 C1 H1B 109.2 . . ? C2 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C3 C2 C1 110.5(2) . . ? 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 . . ? C4 C3 C2 124.6(2) . . ? C4 C3 C18 109.4(2) . . ? C2 C3 C18 125.9(2) . . ? C3 C4 C19 108.7(2) . . ? C3 C4 C5 124.3(2) . . ? C19 C4 C5 126.9(2) . . ? C4 C5 C6 116.59(18) . . ? C4 C5 C10 109.42(16) . . ? C6 C5 C10 111.01(16) . . ? C4 C5 H5 106.4 . . ? C6 C5 H5 106.4 . . ? C10 C5 H5 106.4 . . ? C5 C6 C7 107.64(17) . . ? C5 C6 H6A 110.2 . . ? C7 C6 H6A 110.2 . . ? C5 C6 H6B 110.2 . . ? C7 C6 H6B 110.2 . . ? H6A C6 H6B 108.5 . . ? C8 C7 C6 114.55(17) . . ? C8 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? C8 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.6 . . ? C14 C8 C9 118.70(18) . . ? C14 C8 C7 118.85(18) . . ? C9 C8 C7 122.41(17) . . ? C11 C9 C8 118.45(18) . . ? C11 C9 C10 120.30(17) . . ? C8 C9 C10 121.11(17) . . ? C9 C10 C1 111.96(17) . . ? C9 C10 C5 108.68(15) . . ? C1 C10 C5 107.54(15) . . ? C9 C10 C20 106.99(15) . . ? C1 C10 C20 109.16(17) . . ? C5 C10 C20 112.57(17) . . ? C12 C11 C9 121.74(19) . . ? C12 C11 H11 119.1 . . ? C9 C11 H11 119.1 . . ? C11 C12 C13 120.9(2) . . ? C11 C12 H12 119.5 . . ? C13 C12 H12 119.5 . . ? C12 C13 C14 117.38(19) . . ? C12 C13 C15 121.2(2) . . ? C14 C13 C15 121.4(2) . . ? O3 C14 C13 118.65(18) . . ? O3 C14 C8 118.5(2) . . ? C13 C14 C8 122.79(19) . . ? C17 C15 C16 112.7(3) . . ? C17 C15 C13 109.7(2) . . ? C16 C15 C13 113.3(3) . . ? C17 C15 H15 106.9 . . ? C16 C15 H15 106.9 . . ? C13 C15 H15 106.9 . . ? 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 . . ? O2 C18 C3 104.3(2) . . ? O2 C18 H18A 110.9 . . ? C3 C18 H18A 110.9 . . ? O2 C18 H18B 110.9 . . ? C3 C18 H18B 110.9 . . ? H18A C18 H18B 108.9 . . ? O1 C19 O2 120.9(2) . . ? O1 C19 C4 131.1(2) . . ? O2 C19 C4 108.0(2) . . ? C10 C20 H20A 109.5 . . ? C10 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C10 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 H21A 109.5 . . ? O3 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? O3 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 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 C10 C1 C2 C3 -41.7(3) . . . . ? C1 C2 C3 C4 8.9(4) . . . . ? C1 C2 C3 C18 -168.1(2) . . . . ? C2 C3 C4 C19 -174.4(2) . . . . ? C18 C3 C4 C19 3.0(3) . . . . ? C2 C3 C4 C5 0.7(4) . . . . ? C18 C3 C4 C5 178.1(2) . . . . ? C3 C4 C5 C6 148.9(2) . . . . ? C19 C4 C5 C6 -36.9(3) . . . . ? C3 C4 C5 C10 21.9(3) . . . . ? C19 C4 C5 C10 -163.89(19) . . . . ? C4 C5 C6 C7 166.52(17) . . . . ? C10 C5 C6 C7 -67.3(2) . . . . ? C5 C6 C7 C8 42.4(2) . . . . ? C6 C7 C8 C14 167.07(17) . . . . ? C6 C7 C8 C9 -10.9(3) . . . . ? C14 C8 C9 C11 -1.5(3) . . . . ? C7 C8 C9 C11 176.44(19) . . . . ? C14 C8 C9 C10 -177.22(16) . . . . ? C7 C8 C9 C10 0.8(3) . . . . ? C11 C9 C10 C1 42.9(2) . . . . ? C8 C9 C10 C1 -141.46(19) . . . . ? C11 C9 C10 C5 161.58(17) . . . . ? C8 C9 C10 C5 -22.8(2) . . . . ? C11 C9 C10 C20 -76.6(2) . . . . ? C8 C9 C10 C20 99.0(2) . . . . ? C2 C1 C10 C9 -176.03(18) . . . . ? C2 C1 C10 C5 64.7(2) . . . . ? C2 C1 C10 C20 -57.8(2) . . . . ? C4 C5 C10 C9 -173.39(16) . . . . ? C6 C5 C10 C9 56.5(2) . . . . ? C4 C5 C10 C1 -52.0(2) . . . . ? C6 C5 C10 C1 177.93(17) . . . . ? C4 C5 C10 C20 68.3(2) . . . . ? C6 C5 C10 C20 -61.8(2) . . . . ? C8 C9 C11 C12 1.1(3) . . . . ? C10 C9 C11 C12 176.77(19) . . . . ? C9 C11 C12 C13 0.5(3) . . . . ? C11 C12 C13 C14 -1.5(3) . . . . ? C11 C12 C13 C15 -179.1(2) . . . . ? C21 O3 C14 C13 -102.0(2) . . . . ? C21 O3 C14 C8 81.4(2) . . . . ? C12 C13 C14 O3 -175.49(18) . . . . ? C15 C13 C14 O3 2.2(3) . . . . ? C12 C13 C14 C8 0.9(3) . . . . ? C15 C13 C14 C8 178.61(19) . . . . ? C9 C8 C14 O3 176.99(17) . . . . ? C7 C8 C14 O3 -1.1(3) . . . . ? C9 C8 C14 C13 0.6(3) . . . . ? C7 C8 C14 C13 -177.49(19) . . . . ? C12 C13 C15 C17 93.3(3) . . . . ? C14 C13 C15 C17 -84.3(3) . . . . ? C12 C13 C15 C16 -33.6(3) . . . . ? C14 C13 C15 C16 148.9(2) . . . . ? C19 O2 C18 C3 -0.2(3) . . . . ? C4 C3 C18 O2 -1.8(3) . . . . ? C2 C3 C18 O2 175.6(2) . . . . ? C18 O2 C19 O1 -176.3(3) . . . . ? C18 O2 C19 C4 2.0(3) . . . . ? C3 C4 C19 O1 174.9(3) . . . . ? C5 C4 C19 O1 -0.1(4) . . . . ? C3 C4 C19 O2 -3.2(3) . . . . ? C5 C4 C19 O2 -178.15(19) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.189 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.048 # Attachment '3132_web_deposit_cif_file_1_BingZhou_1289543588.cif' data_cd201565 _database_code_depnum_ccdc_archive 'CCDC 800758' #TrackingRef '3132_web_deposit_cif_file_1_BingZhou_1289543588.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 O6' _chemical_formula_weight 358.38 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 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 9.3443(7) _cell_length_b 11.4954(8) _cell_length_c 16.1665(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1736.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5647 _cell_measurement_theta_min 4.348 _cell_measurement_theta_max 56.124 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.405 _exptl_crystal_size_mid 0.357 _exptl_crystal_size_min 0.303 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.371 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.80397 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10199 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 27.00 _reflns_number_total 2155 _reflns_number_gt 2015 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0866P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.008(2) _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) _chemical_absolute_configuration ad _refine_ls_number_reflns 2155 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0410 _refine_ls_R_factor_gt 0.0390 _refine_ls_wR_factor_ref 0.1055 _refine_ls_wR_factor_gt 0.1035 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 O1 O 0.12936(17) 0.81214(12) 0.03760(8) 0.0484(4) Uani 1 1 d . . . O2 O 0.08148(15) 0.66397(11) 0.20861(9) 0.0465(4) Uani 1 1 d . . . O3 O 0.42265(14) 0.56941(12) 0.13996(9) 0.0457(3) Uani 1 1 d . . . O4 O 0.1734(3) 0.59842(15) -0.01705(11) 0.0751(6) Uani 1 1 d . . . O5 O 0.48597(18) 1.16517(13) 0.14130(10) 0.0564(4) Uani 1 1 d . . . O6 O 0.38576(17) 1.23795(11) 0.25582(9) 0.0484(4) Uani 1 1 d . . . C1 C 0.2044(2) 0.86326(16) 0.31285(11) 0.0377(4) Uani 1 1 d . . . H1A H 0.1313 0.8133 0.3364 0.045 Uiso 1 1 calc R . . H1B H 0.2970 0.8304 0.3265 0.045 Uiso 1 1 calc R . . C2 C 0.1922(2) 0.98514(17) 0.35139(11) 0.0426(4) Uani 1 1 d . . . H2A H 0.0923 1.0076 0.3546 0.051 Uiso 1 1 calc R . . H2B H 0.2307 0.9839 0.4071 0.051 Uiso 1 1 calc R . . C3 C 0.27194(19) 1.07134(16) 0.30082(11) 0.0362(4) Uani 1 1 d . . . C4 C 0.33015(18) 1.04736(15) 0.22704(10) 0.0330(4) Uani 1 1 d . . . C5 C 0.31880(18) 0.93269(14) 0.18302(10) 0.0311(3) Uani 1 1 d . . . H5 H 0.4040 0.8874 0.1977 0.037 Uiso 1 1 calc R . . C6 C 0.3187(3) 0.94592(16) 0.08846(11) 0.0436(4) Uani 1 1 d . . . H6A H 0.2510 1.0061 0.0731 0.052 Uiso 1 1 calc R . . H6B H 0.4129 0.9707 0.0705 0.052 Uiso 1 1 calc R . . C7 C 0.2799(2) 0.83508(16) 0.04430(12) 0.0423(4) Uani 1 1 d . . . H7 H 0.3381 0.8154 -0.0041 0.051 Uiso 1 1 calc R . . C8 C 0.21393(19) 0.73650(15) 0.08839(11) 0.0356(4) Uani 1 1 d . . . C9 C 0.19071(17) 0.74455(14) 0.18044(11) 0.0325(4) Uani 1 1 d . . . C10 C 0.18701(17) 0.86617(15) 0.21789(10) 0.0316(3) Uani 1 1 d . . . C11 C 0.2293(2) 0.64118(15) 0.22861(12) 0.0398(4) Uani 1 1 d . . . H11 H 0.2565 0.6557 0.2862 0.048 Uiso 1 1 calc R . . C12 C 0.2994(2) 0.54021(16) 0.18900(12) 0.0410(4) Uani 1 1 d . . . H12 H 0.3071 0.4696 0.2227 0.049 Uiso 1 1 calc R . . C13 C 0.29759(19) 0.52309(15) 0.09854(12) 0.0367(4) Uani 1 1 d . . . C14 C 0.2238(2) 0.61582(16) 0.05010(12) 0.0407(4) Uani 1 1 d . . . C15 C 0.3158(2) 0.40225(16) 0.06345(13) 0.0435(4) Uani 1 1 d . . . H15 H 0.3735 0.3587 0.1035 0.052 Uiso 1 1 calc R . . C16 C 0.1751(3) 0.3381(2) 0.0558(2) 0.0675(7) Uani 1 1 d . . . H16A H 0.1301 0.3335 0.1091 0.101 Uiso 1 1 calc R . . H16B H 0.1922 0.2610 0.0352 0.101 Uiso 1 1 calc R . . H16C H 0.1136 0.3790 0.0181 0.101 Uiso 1 1 calc R . . C17 C 0.3997(3) 0.4025(3) -0.01701(19) 0.0744(8) Uani 1 1 d . . . H17A H 0.3411 0.4338 -0.0605 0.112 Uiso 1 1 calc R . . H17B H 0.4271 0.3244 -0.0307 0.112 Uiso 1 1 calc R . . H17C H 0.4839 0.4496 -0.0107 0.112 Uiso 1 1 calc R . . C18 C 0.3011(2) 1.19401(16) 0.32325(13) 0.0430(4) Uani 1 1 d . . . H18A H 0.2126 1.2375 0.3286 0.052 Uiso 1 1 calc R . . H18B H 0.3534 1.1987 0.3750 0.052 Uiso 1 1 calc R . . C19 C 0.4085(2) 1.15051(15) 0.20004(12) 0.0407(4) Uani 1 1 d . . . C20 C 0.04270(19) 0.92424(18) 0.19683(13) 0.0426(4) Uani 1 1 d . . . H20A H 0.0241 0.9164 0.1387 0.064 Uiso 1 1 calc R . . H20B H 0.0466 1.0052 0.2111 0.064 Uiso 1 1 calc R . . H20C H -0.0324 0.8873 0.2276 0.064 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 O1 0.0623(8) 0.0379(7) 0.0451(7) 0.0012(6) -0.0194(7) 0.0071(6) O2 0.0424(7) 0.0374(7) 0.0598(8) 0.0028(6) 0.0065(6) -0.0105(6) O3 0.0385(7) 0.0446(7) 0.0540(8) -0.0031(6) -0.0086(6) -0.0047(6) O4 0.1212(16) 0.0464(8) 0.0578(9) -0.0139(7) -0.0418(11) 0.0113(10) O5 0.0668(9) 0.0428(8) 0.0598(8) 0.0036(7) 0.0140(8) -0.0148(7) O6 0.0634(9) 0.0301(6) 0.0516(8) -0.0030(6) -0.0056(6) -0.0043(6) C1 0.0450(9) 0.0338(8) 0.0343(8) 0.0022(7) 0.0048(7) 0.0007(7) C2 0.0521(11) 0.0396(9) 0.0360(9) -0.0023(7) 0.0052(8) 0.0026(8) C3 0.0387(8) 0.0333(8) 0.0366(9) -0.0026(7) -0.0061(7) 0.0052(7) C4 0.0333(8) 0.0302(8) 0.0356(8) 0.0004(6) -0.0052(7) 0.0014(7) C5 0.0336(8) 0.0268(7) 0.0328(8) 0.0006(6) 0.0009(6) -0.0007(6) C6 0.0634(12) 0.0337(9) 0.0337(9) 0.0013(7) 0.0068(9) -0.0059(9) C7 0.0628(11) 0.0322(9) 0.0319(8) 0.0010(7) 0.0008(8) 0.0002(8) C8 0.0413(9) 0.0295(8) 0.0360(8) 0.0003(7) -0.0087(7) 0.0013(7) C9 0.0328(7) 0.0277(8) 0.0369(8) 0.0013(6) -0.0020(6) -0.0035(6) C10 0.0330(8) 0.0283(7) 0.0333(8) 0.0020(6) 0.0003(6) 0.0009(7) C11 0.0513(10) 0.0308(8) 0.0374(9) 0.0046(7) -0.0013(8) -0.0046(8) C12 0.0503(10) 0.0298(8) 0.0428(9) 0.0061(7) -0.0058(8) -0.0007(7) C13 0.0361(9) 0.0293(8) 0.0448(9) -0.0008(7) -0.0035(7) -0.0025(7) C14 0.0514(10) 0.0308(8) 0.0398(9) -0.0033(7) -0.0083(8) -0.0027(8) C15 0.0492(10) 0.0300(8) 0.0512(10) -0.0025(7) 0.0003(9) 0.0026(8) C16 0.0674(15) 0.0444(12) 0.0909(18) -0.0175(12) 0.0030(14) -0.0146(11) C17 0.0854(17) 0.0615(15) 0.0764(16) -0.0158(13) 0.0256(15) 0.0034(14) C18 0.0501(10) 0.0347(9) 0.0441(9) -0.0058(7) -0.0054(8) 0.0045(8) C19 0.0449(9) 0.0313(8) 0.0459(10) 0.0013(7) -0.0053(8) -0.0022(8) C20 0.0347(8) 0.0405(9) 0.0527(11) -0.0027(8) -0.0051(8) 0.0047(8) _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 C8 1.433(2) . ? O1 C7 1.436(3) . ? O2 C11 1.443(3) . ? O2 C9 1.452(2) . ? O3 C12 1.438(2) . ? O3 C13 1.448(2) . ? O4 C14 1.200(3) . ? O5 C19 1.206(2) . ? O6 C19 1.367(2) . ? O6 C18 1.439(3) . ? C1 C2 1.538(2) . ? C1 C10 1.544(2) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.485(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.340(3) . ? C3 C18 1.481(2) . ? C4 C19 1.460(2) . ? C4 C5 1.502(2) . ? C5 C6 1.536(2) . ? C5 C10 1.555(2) . ? C5 H5 0.9800 . ? C6 C7 1.505(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.474(3) . ? C7 H7 0.9800 . ? C8 C9 1.507(2) . ? C8 C14 1.522(2) . ? C9 C11 1.466(2) . ? C9 C10 1.524(2) . ? C10 C20 1.543(2) . ? C11 C12 1.479(3) . ? C11 H11 0.9800 . ? C12 C13 1.476(3) . ? C12 H12 0.9800 . ? C13 C14 1.491(3) . ? C13 C15 1.510(2) . ? C15 C16 1.513(3) . ? C15 C17 1.519(3) . ? 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 0.9700 . ? C18 H18B 0.9700 . ? 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 O1 C7 61.83(12) . . ? C11 O2 C9 60.85(11) . . ? C12 O3 C13 61.50(12) . . ? C19 O6 C18 109.10(14) . . ? C2 C1 C10 112.05(14) . . ? C2 C1 H1A 109.2 . . ? C10 C1 H1A 109.2 . . ? C2 C1 H1B 109.2 . . ? C10 C1 H1B 109.2 . . ? H1A C1 H1B 107.9 . . ? C3 C2 C1 110.36(15) . . ? C3 C2 H2A 109.6 . . ? C1 C2 H2A 109.6 . . ? C3 C2 H2B 109.6 . . ? C1 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C4 C3 C18 109.84(17) . . ? C4 C3 C2 123.81(16) . . ? C18 C3 C2 126.35(17) . . ? C3 C4 C19 107.61(15) . . ? C3 C4 C5 125.03(15) . . ? C19 C4 C5 127.33(15) . . ? C4 C5 C6 112.63(14) . . ? C4 C5 C10 108.40(13) . . ? C6 C5 C10 114.13(15) . . ? C4 C5 H5 107.1 . . ? C6 C5 H5 107.1 . . ? C10 C5 H5 107.1 . . ? C7 C6 C5 112.86(15) . . ? C7 C6 H6A 109.0 . . ? C5 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? O1 C7 C8 59.01(12) . . ? O1 C7 C6 115.30(18) . . ? C8 C7 C6 121.49(16) . . ? O1 C7 H7 116.2 . . ? C8 C7 H7 116.2 . . ? C6 C7 H7 116.2 . . ? O1 C8 C7 59.16(13) . . ? O1 C8 C9 116.68(15) . . ? C7 C8 C9 119.38(14) . . ? O1 C8 C14 110.70(14) . . ? C7 C8 C14 118.60(16) . . ? C9 C8 C14 117.81(15) . . ? O2 C9 C11 59.27(12) . . ? O2 C9 C8 111.84(14) . . ? C11 C9 C8 116.07(15) . . ? O2 C9 C10 116.41(14) . . ? C11 C9 C10 122.56(15) . . ? C8 C9 C10 116.88(14) . . ? C9 C10 C20 109.22(14) . . ? C9 C10 C1 111.89(14) . . ? C20 C10 C1 108.70(15) . . ? C9 C10 C5 106.80(13) . . ? C20 C10 C5 113.54(14) . . ? C1 C10 C5 106.73(14) . . ? O2 C11 C9 59.87(11) . . ? O2 C11 C12 118.01(16) . . ? C9 C11 C12 121.01(16) . . ? O2 C11 H11 115.5 . . ? C9 C11 H11 115.5 . . ? C12 C11 H11 115.5 . . ? O3 C12 C13 59.60(12) . . ? O3 C12 C11 114.23(15) . . ? C13 C12 C11 121.92(16) . . ? O3 C12 H12 116.2 . . ? C13 C12 H12 116.2 . . ? C11 C12 H12 116.2 . . ? O3 C13 C12 58.90(12) . . ? O3 C13 C14 110.67(15) . . ? C12 C13 C14 115.49(16) . . ? O3 C13 C15 114.88(16) . . ? C12 C13 C15 119.58(16) . . ? C14 C13 C15 120.82(16) . . ? O4 C14 C13 122.49(18) . . ? O4 C14 C8 119.74(18) . . ? C13 C14 C8 117.77(15) . . ? C13 C15 C16 112.40(18) . . ? C13 C15 C17 112.21(17) . . ? C16 C15 C17 112.3(2) . . ? C13 C15 H15 106.5 . . ? C16 C15 H15 106.5 . . ? C17 C15 H15 106.5 . . ? 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 . . ? 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 . . ? O6 C18 C3 104.47(16) . . ? O6 C18 H18A 110.9 . . ? C3 C18 H18A 110.9 . . ? O6 C18 H18B 110.9 . . ? C3 C18 H18B 110.9 . . ? H18A C18 H18B 108.9 . . ? O5 C19 O6 120.66(16) . . ? O5 C19 C4 130.53(17) . . ? O6 C19 C4 108.78(15) . . ? C10 C20 H20A 109.5 . . ? C10 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C10 C20 H20C 109.5 . . ? 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 C10 C1 C2 C3 -42.6(2) . . . . ? C1 C2 C3 C4 7.7(3) . . . . ? C1 C2 C3 C18 -171.55(17) . . . . ? C18 C3 C4 C19 3.79(19) . . . . ? C2 C3 C4 C19 -175.55(17) . . . . ? C18 C3 C4 C5 -178.02(16) . . . . ? C2 C3 C4 C5 2.6(3) . . . . ? C3 C4 C5 C6 148.51(18) . . . . ? C19 C4 C5 C6 -33.7(2) . . . . ? C3 C4 C5 C10 21.3(2) . . . . ? C19 C4 C5 C10 -160.92(16) . . . . ? C4 C5 C6 C7 -169.24(16) . . . . ? C10 C5 C6 C7 -45.1(2) . . . . ? C8 O1 C7 C6 -112.96(17) . . . . ? C5 C6 C7 O1 82.5(2) . . . . ? C5 C6 C7 C8 14.7(3) . . . . ? C7 O1 C8 C9 109.84(17) . . . . ? C7 O1 C8 C14 -111.74(17) . . . . ? C6 C7 C8 O1 102.5(2) . . . . ? O1 C7 C8 C9 -105.31(18) . . . . ? C6 C7 C8 C9 -2.8(3) . . . . ? O1 C7 C8 C14 98.24(17) . . . . ? C6 C7 C8 C14 -159.25(18) . . . . ? C11 O2 C9 C8 108.22(16) . . . . ? C11 O2 C9 C10 -113.82(17) . . . . ? O1 C8 C9 O2 90.84(18) . . . . ? C7 C8 C9 O2 158.78(16) . . . . ? C14 C8 C9 O2 -44.6(2) . . . . ? O1 C8 C9 C11 156.21(16) . . . . ? C7 C8 C9 C11 -135.85(18) . . . . ? C14 C8 C9 C11 20.8(2) . . . . ? O1 C8 C9 C10 -46.9(2) . . . . ? C7 C8 C9 C10 21.0(2) . . . . ? C14 C8 C9 C10 177.67(15) . . . . ? O2 C9 C10 C20 -60.57(19) . . . . ? C11 C9 C10 C20 -129.48(18) . . . . ? C8 C9 C10 C20 75.26(18) . . . . ? O2 C9 C10 C1 59.83(19) . . . . ? C11 C9 C10 C1 -9.1(2) . . . . ? C8 C9 C10 C1 -164.34(14) . . . . ? O2 C9 C10 C5 176.27(13) . . . . ? C11 C9 C10 C5 107.36(17) . . . . ? C8 C9 C10 C5 -47.90(18) . . . . ? C2 C1 C10 C9 -176.79(14) . . . . ? C2 C1 C10 C20 -56.1(2) . . . . ? C2 C1 C10 C5 66.73(18) . . . . ? C4 C5 C10 C9 -172.54(13) . . . . ? C6 C5 C10 C9 61.06(18) . . . . ? C4 C5 C10 C20 67.02(18) . . . . ? C6 C5 C10 C20 -59.4(2) . . . . ? C4 C5 C10 C1 -52.72(17) . . . . ? C6 C5 C10 C1 -179.11(14) . . . . ? C9 O2 C11 C12 -111.47(18) . . . . ? C8 C9 C11 O2 -101.01(16) . . . . ? C10 C9 C11 O2 103.55(17) . . . . ? O2 C9 C11 C12 106.5(2) . . . . ? C8 C9 C11 C12 5.5(2) . . . . ? C10 C9 C11 C12 -149.90(17) . . . . ? C13 O3 C12 C11 -114.09(18) . . . . ? O2 C11 C12 O3 120.46(17) . . . . ? C9 C11 C12 O3 50.6(2) . . . . ? O2 C11 C12 C13 52.4(2) . . . . ? C9 C11 C12 C13 -17.5(3) . . . . ? C12 O3 C13 C14 108.03(17) . . . . ? C12 O3 C13 C15 -110.84(18) . . . . ? C11 C12 C13 O3 101.25(19) . . . . ? O3 C12 C13 C14 -99.73(17) . . . . ? C11 C12 C13 C14 1.5(3) . . . . ? O3 C12 C13 C15 102.86(19) . . . . ? C11 C12 C13 C15 -155.89(18) . . . . ? O3 C13 C14 O4 140.2(2) . . . . ? C12 C13 C14 O4 -155.4(2) . . . . ? C15 C13 C14 O4 1.8(3) . . . . ? O3 C13 C14 C8 -39.5(2) . . . . ? C12 C13 C14 C8 24.9(3) . . . . ? C15 C13 C14 C8 -177.99(16) . . . . ? O1 C8 C14 O4 5.4(3) . . . . ? C7 C8 C14 O4 -59.9(3) . . . . ? C9 C8 C14 O4 143.3(2) . . . . ? O1 C8 C14 C13 -174.85(16) . . . . ? C7 C8 C14 C13 119.87(18) . . . . ? C9 C8 C14 C13 -37.0(3) . . . . ? O3 C13 C15 C16 154.7(2) . . . . ? C12 C13 C15 C16 87.7(3) . . . . ? C14 C13 C15 C16 -68.4(3) . . . . ? O3 C13 C15 C17 -77.6(2) . . . . ? C12 C13 C15 C17 -144.6(2) . . . . ? C14 C13 C15 C17 59.2(3) . . . . ? C19 O6 C18 C3 -1.5(2) . . . . ? C4 C3 C18 O6 -1.6(2) . . . . ? C2 C3 C18 O6 177.76(17) . . . . ? C18 O6 C19 O5 -174.50(19) . . . . ? C18 O6 C19 C4 3.8(2) . . . . ? C3 C4 C19 O5 173.3(2) . . . . ? C5 C4 C19 O5 -4.9(3) . . . . ? C3 C4 C19 O6 -4.8(2) . . . . ? C5 C4 C19 O6 177.08(15) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.264 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.048