# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_ps-338m _database_code_depnum_ccdc_archive 'CCDC 819363' #TrackingRef 'PS-338M.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 O5' _chemical_formula_weight 346.41 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 n a 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 19.8370(10) _cell_length_b 15.2026(8) _cell_length_c 6.3744(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1922.35(18) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 4652 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 21.73 _exptl_crystal_description rod _exptl_crystal_colour orange _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.197 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9585 _exptl_absorpt_correction_T_max 0.9789 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 16994 _diffrn_reflns_av_R_equivalents 0.1138 _diffrn_reflns_av_sigmaI/netI 0.0692 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 24.74 _reflns_number_total 1810 _reflns_number_gt 1567 _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' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.3000P] 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 none _refine_ls_extinction_method ? _refine_ls_extinction_coef 0.013(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 0.0(18) _refine_ls_number_reflns 3185 _refine_ls_number_parameters 231 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0856 _refine_ls_R_factor_gt 0.0677 _refine_ls_wR_factor_ref 0.1735 _refine_ls_wR_factor_gt 0.1644 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.943 _refine_ls_shift/su_max 0.012 _refine_ls_shift/su_mean 0.005 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 0.29841(17) 0.5838(2) 0.1998(6) 0.0537(8) Uani 1 1 d . . . C5 C 0.18181(18) 0.6063(2) 0.2815(5) 0.0577(9) Uani 1 1 d . . . H5 H 0.1473 0.6079 0.3803 0.069 Uiso 1 1 calc R . . C6 C 0.24660(17) 0.5856(2) 0.3456(6) 0.0572(9) Uani 1 1 d . . . H6 H 0.2553 0.5731 0.4858 0.069 Uiso 1 1 calc R . . C2 C 0.2840(2) 0.6003(3) -0.0061(6) 0.0728(11) Uani 1 1 d . . . H2 H 0.3183 0.5979 -0.1054 0.087 Uiso 1 1 calc R . . C3 C 0.21918(19) 0.6206(3) -0.0686(6) 0.0699(11) Uani 1 1 d . . . H3 H 0.2104 0.6318 -0.2093 0.084 Uiso 1 1 calc R . . C4 C 0.1803(3) 0.8527(3) 0.1210(10) 0.1085(16) Uani 1 1 d . . . H4A H 0.2080 0.8936 0.0454 0.163 Uiso 1 1 calc R . . H4B H 0.2082 0.8080 0.1824 0.163 Uiso 1 1 calc R . . H4C H 0.1563 0.8832 0.2298 0.163 Uiso 1 1 calc R . . C7 C 0.36942(19) 0.5651(2) 0.2647(7) 0.0626(10) Uani 1 1 d . . . O1 O 0.41427(13) 0.5529(2) 0.1404(5) 0.0868(10) Uani 1 1 d . . . O2 O 0.37729(11) 0.56386(18) 0.4701(5) 0.0732(8) Uani 1 1 d . . . C8 C 0.44459(19) 0.5446(3) 0.5469(8) 0.0886(14) Uani 1 1 d . . . H8A H 0.4595 0.4894 0.4904 0.133 Uiso 1 1 calc R . . H8B H 0.4438 0.5413 0.6973 0.133 Uiso 1 1 calc R . . H8C H 0.4749 0.5904 0.5039 0.133 Uiso 1 1 calc R . . C12 C -0.04141(17) 0.7013(2) 0.0900(6) 0.0595(9) Uani 1 1 d . . . H12 H -0.0837 0.7120 0.0150 0.071 Uiso 1 1 calc R . . C10 C 0.08214(16) 0.7479(2) 0.0722(6) 0.0576(9) Uani 1 1 d . . . H10 H 0.0857 0.7514 0.2253 0.069 Uiso 1 1 calc R . . C9 C 0.09765(15) 0.6528(2) 0.0062(5) 0.0528(8) Uani 1 1 d . . . H9 H 0.0944 0.6480 -0.1468 0.063 Uiso 1 1 calc R . . C13 C -0.01696(16) 0.6089(2) 0.0277(6) 0.0598(9) Uani 1 1 d . . . H13 H -0.0169 0.6051 -0.1258 0.072 Uiso 1 1 calc R . . C11 C 0.00962(18) 0.7691(2) 0.0115(6) 0.0639(10) Uani 1 1 d . . . H11A H 0.0066 0.7728 -0.1401 0.077 Uiso 1 1 calc R . . H11B H -0.0022 0.8263 0.0681 0.077 Uiso 1 1 calc R . . O3 O 0.05062(11) 0.59326(13) 0.1007(4) 0.0575(6) Uani 1 1 d . . . C14 C -0.05966(18) 0.5343(3) 0.1122(8) 0.0755(11) Uani 1 1 d . . . H14A H -0.0449 0.4798 0.0517 0.113 Uiso 1 1 calc R . . H14B H -0.1060 0.5443 0.0764 0.113 Uiso 1 1 calc R . . H14C H -0.0551 0.5316 0.2620 0.113 Uiso 1 1 calc R . . C15 C 0.16734(16) 0.62448(19) 0.0756(5) 0.0517(8) Uani 1 1 d . . . C16 C 0.1324(2) 0.8123(2) -0.0220(7) 0.0709(11) Uani 1 1 d . . . C17 C 0.1329(3) 0.8300(3) -0.2289(9) 0.0980(15) Uani 1 1 d . . . H17A H 0.1645 0.8689 -0.2837 0.118 Uiso 1 1 calc R . . H17B H 0.1017 0.8032 -0.3172 0.118 Uiso 1 1 calc R . . C18 C -0.0560(2) 0.7090(2) 0.3169(7) 0.0640(9) Uani 1 1 d . . . O4 O -0.01737(16) 0.7146(2) 0.4583(5) 0.0970(10) Uani 1 1 d . . . O5 O -0.12323(15) 0.7077(2) 0.3493(5) 0.0896(9) Uani 1 1 d . . . C19 C -0.1485(3) 0.7116(4) 0.5642(9) 0.1170(18) Uani 1 1 d . . . H19A H -0.1126 0.7308 0.6569 0.140 Uiso 1 1 calc R . . H19B H -0.1847 0.7542 0.5724 0.140 Uiso 1 1 calc R . . C20 C -0.1714(4) 0.6316(5) 0.6282(11) 0.159(3) Uani 1 1 d . . . H20A H -0.2092 0.6146 0.5433 0.238 Uiso 1 1 calc R . . H20B H -0.1852 0.6351 0.7724 0.238 Uiso 1 1 calc R . . H20C H -0.1362 0.5888 0.6141 0.238 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 0.046(2) 0.0467(19) 0.068(2) 0.0008(15) 0.0042(17) -0.0007(16) C5 0.047(2) 0.066(2) 0.060(2) 0.0044(18) 0.0103(16) 0.0059(17) C6 0.050(2) 0.067(2) 0.0555(19) 0.0051(17) 0.0045(18) 0.0094(16) C2 0.058(2) 0.092(3) 0.069(3) 0.009(2) 0.022(2) 0.013(2) C3 0.066(3) 0.088(3) 0.056(2) 0.0075(19) 0.0053(19) 0.019(2) C4 0.100(3) 0.081(3) 0.145(5) 0.009(3) -0.003(4) -0.014(3) C7 0.050(2) 0.050(2) 0.088(3) 0.0056(19) 0.005(2) 0.0015(17) O1 0.0460(15) 0.101(2) 0.114(2) 0.0123(18) 0.0152(17) 0.0034(14) O2 0.0490(15) 0.0770(18) 0.094(2) 0.0000(14) -0.0074(14) 0.0113(12) C8 0.052(2) 0.090(3) 0.124(4) 0.003(3) -0.026(2) 0.011(2) C12 0.050(2) 0.072(2) 0.0561(19) 0.001(2) -0.0049(16) 0.0156(17) C10 0.058(2) 0.0496(18) 0.065(2) 0.0004(17) 0.0029(18) 0.0082(15) C9 0.0518(19) 0.0512(18) 0.0555(19) -0.0010(15) 0.0009(15) 0.0089(16) C13 0.052(2) 0.063(2) 0.065(2) -0.0018(16) -0.0094(17) 0.0014(17) C11 0.063(2) 0.059(2) 0.070(2) 0.0031(17) 0.0049(18) 0.0170(18) O3 0.0488(13) 0.0529(12) 0.0708(14) 0.0052(12) -0.0064(12) 0.0044(10) C14 0.062(2) 0.071(2) 0.093(3) -0.004(2) -0.007(2) -0.0017(19) C15 0.0508(19) 0.0469(17) 0.058(2) -0.0026(15) 0.0029(17) 0.0020(14) C16 0.073(3) 0.053(2) 0.087(3) 0.005(2) 0.004(2) 0.0047(18) C17 0.101(4) 0.088(3) 0.105(4) 0.031(3) 0.019(3) 0.006(3) C18 0.061(2) 0.067(2) 0.064(2) 0.0026(19) 0.000(2) 0.0072(18) O4 0.087(2) 0.136(3) 0.0680(18) -0.0136(18) -0.0091(17) 0.0021(19) O5 0.080(2) 0.114(2) 0.0746(19) -0.0045(18) 0.0132(16) -0.0051(16) C19 0.154(5) 0.109(4) 0.088(4) 0.000(3) 0.029(4) -0.021(4) C20 0.196(7) 0.167(7) 0.113(5) 0.005(5) 0.024(5) -0.069(5) _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 1.366(5) . ? C1 C6 1.386(5) . ? C1 C7 1.495(5) . ? C5 C15 1.371(5) . ? C5 C6 1.385(5) . ? C2 C3 1.381(5) . ? C3 C15 1.380(5) . ? C4 C16 1.453(6) . ? C7 O1 1.206(4) . ? C7 O2 1.319(5) . ? O2 C8 1.452(4) . ? C12 C18 1.480(6) . ? C12 C11 1.530(5) . ? C12 C13 1.538(5) . ? C10 C16 1.521(5) . ? C10 C11 1.524(5) . ? C10 C9 1.537(5) . ? C9 O3 1.433(4) . ? C9 C15 1.514(4) . ? C13 O3 1.439(4) . ? C13 C14 1.514(5) . ? C16 C17 1.346(7) . ? C18 O4 1.186(5) . ? C18 O5 1.350(5) . ? O5 C19 1.459(6) . ? C19 C20 1.360(7) . ? 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 C6 119.0(3) . . ? C2 C1 C7 119.8(3) . . ? C6 C1 C7 121.1(4) . . ? C15 C5 C6 121.5(3) . . ? C5 C6 C1 119.7(3) . . ? C1 C2 C3 120.8(3) . . ? C15 C3 C2 120.7(3) . . ? O1 C7 O2 124.3(4) . . ? O1 C7 C1 122.8(4) . . ? O2 C7 C1 112.9(3) . . ? C7 O2 C8 116.5(3) . . ? C18 C12 C11 113.3(3) . . ? C18 C12 C13 112.8(3) . . ? C11 C12 C13 108.8(3) . . ? C16 C10 C11 112.4(3) . . ? C16 C10 C9 111.5(3) . . ? C11 C10 C9 108.6(3) . . ? O3 C9 C15 107.0(3) . . ? O3 C9 C10 110.4(3) . . ? C15 C9 C10 111.7(3) . . ? O3 C13 C14 106.4(3) . . ? O3 C13 C12 111.2(3) . . ? C14 C13 C12 114.5(3) . . ? C10 C11 C12 113.5(3) . . ? C9 O3 C13 111.5(2) . . ? C5 C15 C3 118.2(3) . . ? C5 C15 C9 121.9(3) . . ? C3 C15 C9 119.9(3) . . ? C17 C16 C4 121.7(5) . . ? C17 C16 C10 121.4(4) . . ? C4 C16 C10 116.9(4) . . ? O4 C18 O5 121.6(4) . . ? O4 C18 C12 128.5(4) . . ? O5 C18 C12 110.0(4) . . ? C18 O5 C19 118.8(4) . . ? C20 C19 O5 111.2(5) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.74 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.241 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.048 data_ps-451l _database_code_depnum_ccdc_archive 'CCDC 819364' #TrackingRef '- AKS-13.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 O4' _chemical_formula_weight 366.44 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 0.0016 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.9913(7) _cell_length_b 19.6654(14) _cell_length_c 11.4452(9) _cell_angle_alpha 90.00 _cell_angle_beta 103.239(4) _cell_angle_gamma 90.00 _cell_volume 1969.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.37 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.236 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.963 _exptl_absorpt_correction_T_max 0.979 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 8217 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0313 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.07 _diffrn_reflns_theta_max 24.42 _reflns_number_total 3250 _reflns_number_gt 2852 _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' _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^)+(0.0991P)^2^+1.0222P] 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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2628 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0923 _refine_ls_R_factor_gt 0.0667 _refine_ls_wR_factor_ref 0.1973 _refine_ls_wR_factor_gt 0.1815 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.004 _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 0.3490(2) 0.10030(10) 0.40729(18) 0.0515(6) Uani 1 1 d . . . O4 O 0.6144(3) 0.01901(14) 0.1892(2) 0.0802(8) Uani 1 1 d . . . O2 O 0.5696(3) 0.31481(13) 0.4880(2) 0.0806(9) Uani 1 1 d . . . O3 O 0.6109(4) 0.24767(14) 0.6436(3) 0.1079(12) Uani 1 1 d . . . C8 C 0.5716(4) 0.10900(17) 0.3225(3) 0.0579(9) Uani 1 1 d . . . H8 H 0.5055 0.1300 0.2518 0.069 Uiso 1 1 calc R . . C7 C 0.4741(4) 0.06384(17) 0.3758(3) 0.0609(10) Uani 1 1 d . . . H7 H 0.5370 0.0441 0.4492 0.073 Uiso 1 1 calc R . . C10 C 0.4981(4) 0.20200(17) 0.4473(3) 0.0601(10) Uani 1 1 d . . . H10 H 0.4344 0.2243 0.3767 0.072 Uiso 1 1 calc R . . C9 C 0.6340(4) 0.16653(16) 0.4098(3) 0.0558(9) Uani 1 1 d . . . H9A H 0.6887 0.1991 0.3716 0.067 Uiso 1 1 calc R . . H9B H 0.7044 0.1484 0.4800 0.067 Uiso 1 1 calc R . . C11 C 0.4023(4) 0.15132(17) 0.4949(3) 0.0592(9) Uani 1 1 d . . . H11 H 0.4664 0.1295 0.5658 0.071 Uiso 1 1 calc R . . C6 C 0.4098(4) 0.00693(16) 0.2926(3) 0.0563(9) Uani 1 1 d . . . C12 C 0.2644(4) 0.18038(16) 0.5293(3) 0.0531(9) Uani 1 1 d . . . C5 C 0.2792(5) -0.02899(19) 0.3015(3) 0.0681(10) Uani 1 1 d . . . H5 H 0.2264 -0.0161 0.3589 0.082 Uiso 1 1 calc R . . C21 C 0.6931(4) 0.06801(18) 0.2778(3) 0.0605(10) Uani 1 1 d . . . C1 C 0.4872(4) -0.01391(17) 0.2092(3) 0.0567(9) Uani 1 1 d . . . C2 C 0.4339(5) -0.06756(19) 0.1328(4) 0.0735(11) Uani 1 1 d . . . H2 H 0.4850 -0.0803 0.0742 0.088 Uiso 1 1 calc R . . C18 C 0.5653(4) 0.25641(19) 0.5397(4) 0.0612(10) Uani 1 1 d . . . C3 C 0.3046(5) -0.10199(19) 0.1442(4) 0.0758(12) Uani 1 1 d . . . H3 H 0.2701 -0.1387 0.0942 0.091 Uiso 1 1 calc R . . C13 C 0.2450(5) 0.17085(17) 0.6438(3) 0.0657(10) Uani 1 1 d . . . H13 H 0.3199 0.1480 0.6993 0.079 Uiso 1 1 calc R . . C4 C 0.2270(5) -0.08282(19) 0.2276(3) 0.0704(11) Uani 1 1 d . . . H4 H 0.1394 -0.1060 0.2345 0.085 Uiso 1 1 calc R . . C16 C 0.0249(5) 0.2392(2) 0.4833(4) 0.0786(12) Uani 1 1 d . . . H16 H -0.0497 0.2631 0.4290 0.094 Uiso 1 1 calc R . . C17 C 0.1521(4) 0.21484(18) 0.4484(3) 0.0632(10) Uani 1 1 d . . . H17 H 0.1622 0.2216 0.3701 0.076 Uiso 1 1 calc R . . C19 C 0.6352(6) 0.3718(2) 0.5617(4) 0.0960(15) Uani 1 1 d . . . H19A H 0.5625 0.3884 0.6059 0.115 Uiso 1 1 calc R . . H19B H 0.7260 0.3569 0.6195 0.115 Uiso 1 1 calc R . . C15 C 0.0089(5) 0.2282(2) 0.5984(5) 0.0802(12) Uani 1 1 d . . . H15 H -0.0773 0.2441 0.6217 0.096 Uiso 1 1 calc R . . C14 C 0.1183(6) 0.1942(2) 0.6779(4) 0.0786(12) Uani 1 1 d . . . H14 H 0.1072 0.1867 0.7557 0.094 Uiso 1 1 calc R . . C23 C 0.7767(5) 0.1133(2) 0.2064(4) 0.0899(14) Uani 1 1 d . . . H23A H 0.8401 0.0858 0.1683 0.135 Uiso 1 1 calc R . . H23B H 0.8391 0.1452 0.2595 0.135 Uiso 1 1 calc R . . H23C H 0.7037 0.1374 0.1464 0.135 Uiso 1 1 calc R . . C22 C 0.8050(5) 0.0291(2) 0.3725(4) 0.0868(13) Uani 1 1 d . . . H22A H 0.7509 -0.0035 0.4094 0.130 Uiso 1 1 calc R . . H22B H 0.8586 0.0602 0.4322 0.130 Uiso 1 1 calc R . . H22C H 0.8769 0.0060 0.3361 0.130 Uiso 1 1 calc R . . C20 C 0.6727(9) 0.4231(3) 0.4939(6) 0.165(3) Uani 1 1 d . . . H20A H 0.7471 0.4072 0.4521 0.247 Uiso 1 1 calc R . . H20B H 0.7144 0.4605 0.5450 0.247 Uiso 1 1 calc R . . H20C H 0.5829 0.4379 0.4368 0.247 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 0.0542(14) 0.0522(13) 0.0500(13) -0.0104(10) 0.0161(11) -0.0070(11) O4 0.0780(18) 0.0857(18) 0.0806(18) -0.0392(15) 0.0258(15) -0.0090(15) O2 0.117(2) 0.0566(16) 0.0656(16) -0.0130(13) 0.0142(16) -0.0214(15) O3 0.179(3) 0.0741(19) 0.0625(19) -0.0071(16) 0.012(2) -0.017(2) C8 0.056(2) 0.060(2) 0.061(2) -0.0120(17) 0.0194(18) -0.0058(18) C7 0.069(2) 0.057(2) 0.059(2) -0.0096(17) 0.0185(19) -0.0035(19) C10 0.068(2) 0.052(2) 0.062(2) -0.0115(17) 0.0181(19) -0.0054(18) C9 0.055(2) 0.057(2) 0.060(2) -0.0126(17) 0.0228(18) -0.0084(17) C11 0.067(2) 0.059(2) 0.055(2) -0.0141(18) 0.0196(19) -0.0071(19) C6 0.068(2) 0.052(2) 0.047(2) -0.0057(16) 0.0102(18) -0.0081(18) C12 0.057(2) 0.0518(19) 0.052(2) -0.0092(16) 0.0163(19) -0.0051(17) C5 0.080(3) 0.068(2) 0.057(2) -0.0067(19) 0.016(2) -0.013(2) C21 0.056(2) 0.066(2) 0.062(2) -0.0166(19) 0.0173(19) -0.0015(19) C1 0.060(2) 0.050(2) 0.057(2) -0.0073(17) 0.0076(19) 0.0030(18) C2 0.077(3) 0.062(2) 0.076(3) -0.025(2) 0.008(2) 0.010(2) C18 0.068(2) 0.060(2) 0.061(3) -0.015(2) 0.027(2) -0.0082(19) C3 0.091(3) 0.049(2) 0.075(3) -0.0094(19) -0.006(3) -0.001(2) C13 0.084(3) 0.061(2) 0.055(2) -0.0034(18) 0.021(2) 0.008(2) C4 0.077(3) 0.063(2) 0.064(2) -0.003(2) 0.003(2) -0.020(2) C16 0.064(3) 0.067(3) 0.097(3) 0.002(2) 0.002(2) 0.000(2) C17 0.063(2) 0.071(2) 0.058(2) 0.0017(19) 0.018(2) -0.009(2) C19 0.130(4) 0.061(3) 0.099(3) -0.028(2) 0.030(3) -0.030(3) C15 0.069(3) 0.075(3) 0.106(4) -0.027(3) 0.039(3) -0.007(2) C14 0.103(3) 0.075(3) 0.068(3) -0.011(2) 0.043(3) -0.009(3) C23 0.098(3) 0.099(3) 0.084(3) -0.019(2) 0.043(3) -0.007(3) C22 0.077(3) 0.093(3) 0.087(3) -0.015(2) 0.010(2) 0.022(2) C20 0.217(7) 0.125(5) 0.129(5) -0.006(4) -0.007(5) -0.105(5) _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 C11 1.422(4) . ? O1 C7 1.447(4) . ? O4 C1 1.378(4) . ? O4 C21 1.459(4) . ? O2 C18 1.297(4) . ? O2 C19 1.445(4) . ? O3 C18 1.178(4) . ? C8 C7 1.475(5) . ? C8 C9 1.528(4) . ? C8 C21 1.536(5) . ? C7 C6 1.497(4) . ? C10 C11 1.499(5) . ? C10 C18 1.528(5) . ? C10 C9 1.551(5) . ? C11 C12 1.498(5) . ? C6 C1 1.366(5) . ? C6 C5 1.394(5) . ? C12 C13 1.374(5) . ? C12 C17 1.381(5) . ? C5 C4 1.369(5) . ? C21 C22 1.507(5) . ? C21 C23 1.518(5) . ? C1 C2 1.384(5) . ? C2 C3 1.376(5) . ? C3 C4 1.359(6) . ? C13 C14 1.365(5) . ? C16 C15 1.375(6) . ? C16 C17 1.381(5) . ? C19 C20 1.362(6) . ? C15 C14 1.354(6) . ? 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 C11 O1 C7 111.7(2) . . ? C1 O4 C21 118.9(3) . . ? C18 O2 C19 118.1(3) . . ? C7 C8 C9 109.9(3) . . ? C7 C8 C21 110.9(3) . . ? C9 C8 C21 115.1(3) . . ? O1 C7 C8 112.0(3) . . ? O1 C7 C6 108.7(3) . . ? C8 C7 C6 111.5(3) . . ? C11 C10 C18 112.5(3) . . ? C11 C10 C9 110.9(3) . . ? C18 C10 C9 107.1(3) . . ? C8 C9 C10 108.6(3) . . ? O1 C11 C10 110.0(3) . . ? O1 C11 C12 106.8(3) . . ? C10 C11 C12 114.9(3) . . ? C1 C6 C5 118.1(3) . . ? C1 C6 C7 119.0(3) . . ? C5 C6 C7 122.7(3) . . ? C13 C12 C17 118.3(3) . . ? C13 C12 C11 119.5(3) . . ? C17 C12 C11 122.2(3) . . ? C4 C5 C6 121.4(4) . . ? O4 C21 C22 107.6(3) . . ? O4 C21 C23 103.6(3) . . ? C22 C21 C23 110.7(3) . . ? O4 C21 C8 108.0(3) . . ? C22 C21 C8 115.8(3) . . ? C23 C21 C8 110.4(3) . . ? C6 C1 O4 123.4(3) . . ? C6 C1 C2 120.8(4) . . ? O4 C1 C2 115.7(3) . . ? C3 C2 C1 119.5(4) . . ? O3 C18 O2 123.4(3) . . ? O3 C18 C10 126.0(4) . . ? O2 C18 C10 110.7(3) . . ? C4 C3 C2 120.7(4) . . ? C14 C13 C12 121.6(4) . . ? C3 C4 C5 119.4(4) . . ? C15 C16 C17 119.9(4) . . ? C12 C17 C16 120.2(3) . . ? C20 C19 O2 111.3(4) . . ? C14 C15 C16 120.1(4) . . ? C15 C14 C13 120.0(4) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 24.42 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.411 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.042 data_ps_418u _database_code_depnum_ccdc_archive 'CCDC 819365' #TrackingRef 'PS_418U.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H28 O5' _chemical_formula_weight 408.47 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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.0752(3) _cell_length_b 15.3970(4) _cell_length_c 12.4647(3) _cell_angle_alpha 90.00 _cell_angle_beta 104.3910(10) _cell_angle_gamma 90.00 _cell_volume 2244.74(10) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.965 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 27562 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0244 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.74 _diffrn_reflns_theta_max 28.33 _reflns_number_total 5489 _reflns_number_gt 4317 _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' _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^)+(0.1200P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5489 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0759 _refine_ls_R_factor_gt 0.0615 _refine_ls_wR_factor_ref 0.2203 _refine_ls_wR_factor_gt 0.1806 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 O1 O 0.34026(11) 0.13837(8) 0.81164(11) 0.0291(3) Uani 1 1 d . . . O3 O -0.11661(12) 0.36080(9) 0.96449(12) 0.0383(4) Uani 1 1 d . . . O2 O 0.04187(12) 0.40768(9) 1.08542(11) 0.0388(4) Uani 1 1 d . . . O5 O 0.60162(13) -0.08163(10) 0.79967(12) 0.0421(4) Uani 1 1 d . . . O4 O 0.45471(14) -0.07529(11) 0.65045(13) 0.0477(4) Uani 1 1 d . . . C3 C 0.34196(17) -0.04536(12) 0.84305(16) 0.0347(4) Uani 1 1 d . . . H3A H 0.3713 -0.0936 0.8920 0.042 Uiso 1 1 calc R . . H3B H 0.2925 -0.0688 0.7758 0.042 Uiso 1 1 calc R . . C2 C 0.44210(17) 0.00271(12) 0.81426(16) 0.0320(4) Uani 1 1 d . . . H2 H 0.4982 0.0186 0.8828 0.038 Uiso 1 1 calc R . . C1 C 0.39826(16) 0.08564(12) 0.74806(15) 0.0305(4) Uani 1 1 d . . . H1 H 0.3446 0.0695 0.6781 0.037 Uiso 1 1 calc R . . C5 C 0.23926(16) 0.09640(12) 0.82786(15) 0.0308(4) Uani 1 1 d . . . H5 H 0.1911 0.0792 0.7556 0.037 Uiso 1 1 calc R . . C4 C 0.27218(16) 0.01492(12) 0.89951(16) 0.0323(4) Uani 1 1 d . . . H4 H 0.3210 0.0327 0.9712 0.039 Uiso 1 1 calc R . . C6 C 0.49444(16) 0.13807(11) 0.72375(16) 0.0311(4) Uani 1 1 d . . . C11 C 0.50818(19) 0.14132(13) 0.61657(16) 0.0377(5) Uani 1 1 d . . . H11 H 0.4556 0.1136 0.5596 0.045 Uiso 1 1 calc R . . C8 C 0.66415(18) 0.22593(14) 0.7848(2) 0.0442(5) Uani 1 1 d . . . H8 H 0.7162 0.2546 0.8412 0.053 Uiso 1 1 calc R . . C9 C 0.6773(2) 0.22739(14) 0.6776(2) 0.0445(5) Uani 1 1 d . . . H9 H 0.7388 0.2568 0.6622 0.053 Uiso 1 1 calc R . . C7 C 0.57244(17) 0.18121(13) 0.80747(17) 0.0375(5) Uani 1 1 d . . . H7 H 0.5633 0.1802 0.8794 0.045 Uiso 1 1 calc R . . C10 C 0.6000(2) 0.18573(14) 0.59364(19) 0.0442(5) Uani 1 1 d . . . H10 H 0.6090 0.1873 0.5217 0.053 Uiso 1 1 calc R . . C15 C 0.05607(15) 0.28914(12) 0.96626(14) 0.0296(4) Uani 1 1 d . . . C18 C -0.00380(16) 0.35837(12) 1.01258(14) 0.0293(4) Uani 1 1 d . . . C12 C 0.17614(15) 0.16351(12) 0.87825(15) 0.0308(4) Uani 1 1 d . . . C16 C 0.17130(16) 0.27408(13) 1.01454(16) 0.0344(4) Uani 1 1 d . . . H16 H 0.2086 0.3059 1.0764 0.041 Uiso 1 1 calc R . . C14 C 0.00051(17) 0.23993(14) 0.87483(16) 0.0370(5) Uani 1 1 d . . . H14 H -0.0768 0.2487 0.8427 0.044 Uiso 1 1 calc R . . C13 C 0.06096(17) 0.17786(14) 0.83196(16) 0.0375(5) Uani 1 1 d . . . H13 H 0.0234 0.1453 0.7709 0.045 Uiso 1 1 calc R . . C19 C -0.17954(18) 0.42758(15) 1.0060(2) 0.0430(5) Uani 1 1 d . . . H19A H -0.1742 0.4175 1.0831 0.064 Uiso 1 1 calc R . . H19B H -0.2583 0.4260 0.9655 0.064 Uiso 1 1 calc R . . H19C H -0.1478 0.4834 0.9969 0.064 Uiso 1 1 calc R . . C17 C 0.23107(17) 0.21166(13) 0.97079(17) 0.0362(5) Uani 1 1 d . . . H17 H 0.3081 0.2021 1.0035 0.043 Uiso 1 1 calc R . . C20 C 0.49852(16) -0.05551(12) 0.74517(16) 0.0336(4) Uani 1 1 d . . . C21 C 0.6648(2) -0.13311(17) 0.7366(2) 0.0527(6) Uani 1 1 d . . . H21A H 0.6123 -0.1692 0.6835 0.063 Uiso 1 1 calc R . . H21B H 0.7187 -0.1707 0.7861 0.063 Uiso 1 1 calc R . . C22 C 0.7273(3) -0.0740(2) 0.6775(3) 0.0669(8) Uani 1 1 d . . . H22A H 0.6736 -0.0369 0.6285 0.100 Uiso 1 1 calc R . . H22B H 0.7684 -0.1077 0.6353 0.100 Uiso 1 1 calc R . . H22C H 0.7801 -0.0391 0.7304 0.100 Uiso 1 1 calc R . . C24 C 0.16856(18) -0.03211(13) 0.92015(18) 0.0384(5) Uani 1 1 d . . . C25 C 0.0809(2) -0.06473(19) 0.8273(2) 0.0602(7) Uani 1 1 d . . . H25A H 0.0303 -0.1023 0.8540 0.090 Uiso 1 1 calc R . . H25B H 0.1162 -0.0966 0.7784 0.090 Uiso 1 1 calc R . . H25C H 0.0384 -0.0169 0.7880 0.090 Uiso 1 1 calc R . . C23 C 0.1613(3) -0.0424(2) 1.0260(2) 0.0653(8) Uani 1 1 d . . . H23A H 0.0988 -0.0711 1.0407 0.078 Uiso 1 1 calc R . . H23B H 0.2187 -0.0209 1.0841 0.078 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 0.0252(7) 0.0256(6) 0.0370(7) -0.0012(5) 0.0088(5) 0.0004(4) O3 0.0263(7) 0.0417(8) 0.0467(8) -0.0081(6) 0.0089(6) 0.0023(5) O2 0.0372(8) 0.0404(8) 0.0353(7) -0.0041(5) 0.0022(6) 0.0046(6) O5 0.0373(8) 0.0470(9) 0.0425(8) 0.0018(6) 0.0105(6) 0.0136(6) O4 0.0412(9) 0.0535(10) 0.0464(9) -0.0170(7) 0.0070(7) 0.0017(7) C3 0.0365(10) 0.0280(9) 0.0400(10) 0.0004(7) 0.0103(8) -0.0008(7) C2 0.0311(9) 0.0293(9) 0.0346(9) -0.0021(7) 0.0066(7) 0.0009(7) C1 0.0271(9) 0.0299(9) 0.0339(9) -0.0023(7) 0.0066(7) 0.0010(7) C5 0.0257(9) 0.0324(9) 0.0334(9) -0.0001(7) 0.0055(7) -0.0014(7) C4 0.0320(10) 0.0302(9) 0.0342(9) -0.0001(7) 0.0073(7) -0.0023(7) C6 0.0262(9) 0.0244(8) 0.0436(10) -0.0015(7) 0.0103(8) 0.0023(6) C11 0.0398(11) 0.0353(10) 0.0370(10) 0.0010(7) 0.0074(8) 0.0019(8) C8 0.0326(11) 0.0374(11) 0.0632(14) -0.0127(9) 0.0134(10) -0.0080(8) C9 0.0418(12) 0.0303(10) 0.0690(14) 0.0028(9) 0.0284(11) 0.0015(8) C7 0.0345(10) 0.0385(11) 0.0415(10) -0.0090(8) 0.0134(8) -0.0032(8) C10 0.0509(13) 0.0391(11) 0.0482(12) 0.0087(9) 0.0227(10) 0.0055(9) C15 0.0267(9) 0.0332(9) 0.0293(8) 0.0034(7) 0.0073(7) -0.0003(7) C18 0.0277(9) 0.0316(9) 0.0286(8) 0.0040(6) 0.0073(7) -0.0004(6) C12 0.0284(9) 0.0289(9) 0.0366(9) 0.0046(7) 0.0110(7) 0.0001(7) C16 0.0283(10) 0.0355(10) 0.0354(9) -0.0030(7) 0.0004(7) -0.0007(7) C14 0.0241(9) 0.0487(12) 0.0367(10) -0.0060(8) 0.0045(8) 0.0024(8) C13 0.0301(10) 0.0453(11) 0.0359(10) -0.0090(8) 0.0058(8) 0.0007(8) C19 0.0298(10) 0.0445(12) 0.0570(13) -0.0043(9) 0.0152(9) 0.0043(8) C17 0.0259(9) 0.0356(10) 0.0435(11) -0.0002(8) 0.0018(8) 0.0051(7) C20 0.0301(9) 0.0256(9) 0.0446(10) -0.0018(7) 0.0082(8) -0.0012(7) C21 0.0520(15) 0.0533(14) 0.0572(14) 0.0033(10) 0.0222(12) 0.0235(11) C22 0.0615(18) 0.081(2) 0.0662(17) -0.0213(14) 0.0309(14) -0.0095(14) C24 0.0384(11) 0.0301(10) 0.0501(11) -0.0010(8) 0.0174(9) -0.0031(8) C25 0.0498(15) 0.0623(16) 0.0712(16) -0.0136(13) 0.0197(13) -0.0266(12) C23 0.0609(17) 0.080(2) 0.0565(15) 0.0139(13) 0.0171(13) -0.0234(14) _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 C1 1.433(2) . ? O1 C5 1.438(2) . ? O3 C18 1.345(2) . ? O3 C19 1.448(2) . ? O2 C18 1.207(2) . ? O5 C20 1.324(2) . ? O5 C21 1.459(2) . ? O4 C20 1.207(2) . ? C3 C2 1.534(3) . ? C3 C4 1.537(3) . ? C2 C20 1.517(3) . ? C2 C1 1.541(3) . ? C1 C6 1.506(3) . ? C5 C12 1.510(3) . ? C5 C4 1.534(3) . ? C4 C24 1.522(3) . ? C6 C11 1.387(3) . ? C6 C7 1.389(3) . ? C11 C10 1.391(3) . ? C8 C9 1.384(3) . ? C8 C7 1.392(3) . ? C9 C10 1.376(3) . ? C15 C16 1.391(3) . ? C15 C14 1.394(3) . ? C15 C18 1.483(2) . ? C12 C13 1.385(3) . ? C12 C17 1.393(3) . ? C16 C17 1.392(3) . ? C14 C13 1.388(3) . ? C21 C22 1.489(4) . ? C24 C23 1.354(3) . ? C24 C25 1.450(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 C1 O1 C5 111.80(13) . . ? C18 O3 C19 115.06(15) . . ? C20 O5 C21 116.09(17) . . ? C2 C3 C4 111.69(15) . . ? C20 C2 C3 109.81(15) . . ? C20 C2 C1 109.19(15) . . ? C3 C2 C1 109.82(16) . . ? O1 C1 C6 108.36(14) . . ? O1 C1 C2 108.87(14) . . ? C6 C1 C2 111.87(15) . . ? O1 C5 C12 106.52(14) . . ? O1 C5 C4 110.07(15) . . ? C12 C5 C4 113.70(15) . . ? C24 C4 C5 112.49(16) . . ? C24 C4 C3 110.95(15) . . ? C5 C4 C3 108.64(15) . . ? C11 C6 C7 119.03(18) . . ? C11 C6 C1 119.73(18) . . ? C7 C6 C1 121.21(17) . . ? C6 C11 C10 120.5(2) . . ? C9 C8 C7 119.5(2) . . ? C10 C9 C8 120.5(2) . . ? C6 C7 C8 120.62(19) . . ? C9 C10 C11 119.8(2) . . ? C16 C15 C14 119.31(17) . . ? C16 C15 C18 118.90(16) . . ? C14 C15 C18 121.78(17) . . ? O2 C18 O3 122.72(17) . . ? O2 C18 C15 124.69(17) . . ? O3 C18 C15 112.58(15) . . ? C13 C12 C17 118.85(17) . . ? C13 C12 C5 119.63(17) . . ? C17 C12 C5 121.52(16) . . ? C15 C16 C17 120.38(17) . . ? C13 C14 C15 119.79(18) . . ? C12 C13 C14 121.30(18) . . ? C16 C17 C12 120.36(17) . . ? O4 C20 O5 123.57(18) . . ? O4 C20 C2 123.72(17) . . ? O5 C20 C2 112.71(16) . . ? O5 C21 C22 109.4(2) . . ? C23 C24 C25 121.7(2) . . ? C23 C24 C4 118.4(2) . . ? C25 C24 C4 119.81(19) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.757 _refine_diff_density_min -0.415 _refine_diff_density_rms 0.053 data_ps_433l _database_code_depnum_ccdc_archive 'CCDC 819366' #TrackingRef '- AKS-14.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H26 O4' _chemical_formula_weight 366.44 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 0.0016 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.5282(8) _cell_length_b 8.7884(6) _cell_length_c 18.2013(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.582(2) _cell_angle_gamma 90.00 _cell_volume 1997.6(2) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.32 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.961 _exptl_absorpt_correction_T_max 0.974 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 22711 _diffrn_reflns_av_R_equivalents 0.0271 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.63 _diffrn_reflns_theta_max 28.24 _reflns_number_total 4878 _reflns_number_gt 3094 _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' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4878 _refine_ls_number_parameters 247 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0613 _refine_ls_wR_factor_ref 0.2108 _refine_ls_wR_factor_gt 0.1695 _refine_ls_goodness_of_fit_ref 1.373 _refine_ls_restrained_S_all 1.373 _refine_ls_shift/su_max 0.004 _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 0.87074(9) 0.59392(12) 0.10233(6) 0.0470(3) Uani 1 1 d . . . C24 C 0.77125(14) 0.87218(19) 0.05006(9) 0.0494(4) Uani 1 1 d . . . H24A H 0.7508 0.9740 0.0641 0.059 Uiso 1 1 calc R . . H24B H 0.7489 0.8587 -0.0018 0.059 Uiso 1 1 calc R . . O4 O 1.02513(12) 1.00688(17) 0.12502(7) 0.0745(5) Uani 1 1 d . . . O3 O 0.90287(13) 0.90753(19) 0.19199(7) 0.0820(5) Uani 1 1 d . . . C17 C 0.71321(13) 0.75587(17) 0.09520(8) 0.0443(4) Uani 1 1 d . . . H17 H 0.7295 0.7808 0.1474 0.053 Uiso 1 1 calc R . . O2 O 0.54749(10) 0.64644(14) 0.13133(7) 0.0605(4) Uani 1 1 d . . . C8 C 0.75868(13) 0.59859(17) 0.08249(9) 0.0436(4) Uani 1 1 d . . . H8 H 0.7461 0.5734 0.0301 0.052 Uiso 1 1 calc R . . C7 C 0.92767(13) 0.68768(18) 0.05513(8) 0.0458(4) Uani 1 1 d . . . H7 H 0.9087 0.6549 0.0043 0.055 Uiso 1 1 calc R . . C6 C 1.04578(14) 0.66173(19) 0.07163(9) 0.0481(4) Uani 1 1 d . . . C18 C 0.89357(14) 0.85656(18) 0.06151(9) 0.0456(4) Uani 1 1 d . . . H18 H 0.9242 0.9128 0.0217 0.055 Uiso 1 1 calc R . . C9 C 0.70350(14) 0.48259(18) 0.12636(9) 0.0464(4) Uani 1 1 d . . . C16 C 0.59166(14) 0.75473(18) 0.08043(10) 0.0507(4) Uani 1 1 d . . . C14 C 0.60116(15) 0.51324(19) 0.14714(9) 0.0507(4) Uani 1 1 d . . . C19 C 0.93843(15) 0.92538(19) 0.13377(9) 0.0503(4) Uani 1 1 d . . . C10 C 0.75108(17) 0.3444(2) 0.14761(10) 0.0575(5) Uani 1 1 d . . . H10 H 0.8193 0.3222 0.1339 0.069 Uiso 1 1 calc R . . C13 C 0.54844(18) 0.4075(2) 0.18840(11) 0.0631(5) Uani 1 1 d . . . H13 H 0.4800 0.4282 0.2021 0.076 Uiso 1 1 calc R . . C1 C 1.11826(16) 0.7293(2) 0.02762(11) 0.0593(5) Uani 1 1 d . . . H1 H 1.0928 0.7874 -0.0128 0.071 Uiso 1 1 calc R . . C2 C 1.22618(17) 0.7118(3) 0.04270(12) 0.0678(6) Uani 1 1 d . . . H2 H 1.2732 0.7596 0.0131 0.081 Uiso 1 1 calc R . . C5 C 1.08608(16) 0.5725(2) 0.13001(9) 0.0581(5) Uani 1 1 d . . . H5 H 1.0393 0.5250 0.1599 0.070 Uiso 1 1 calc R . . C4 C 1.19516(18) 0.5534(3) 0.14446(11) 0.0697(6) Uani 1 1 d . . . H4 H 1.2211 0.4923 0.1836 0.084 Uiso 1 1 calc R . . C11 C 0.6990(2) 0.2402(2) 0.18839(12) 0.0724(6) Uani 1 1 d . . . H11 H 0.7318 0.1484 0.2021 0.087 Uiso 1 1 calc R . . C3 C 1.26589(18) 0.6243(3) 0.10128(12) 0.0687(6) Uani 1 1 d . . . H3 H 1.3394 0.6130 0.1116 0.082 Uiso 1 1 calc R . . C23 C 0.54125(18) 0.9041(2) 0.10096(13) 0.0673(6) Uani 1 1 d . . . H23A H 0.4649 0.8927 0.0988 0.101 Uiso 1 1 calc R . . H23B H 0.5593 0.9818 0.0670 0.101 Uiso 1 1 calc R . . H23C H 0.5677 0.9323 0.1500 0.101 Uiso 1 1 calc R . . C22 C 0.55202(16) 0.7073(2) 0.00246(11) 0.0650(5) Uani 1 1 d . . . H22A H 0.5761 0.6059 -0.0068 0.097 Uiso 1 1 calc R . . H22B H 0.5798 0.7761 -0.0323 0.097 Uiso 1 1 calc R . . H22C H 0.4752 0.7101 -0.0027 0.097 Uiso 1 1 calc R . . C12 C 0.59763(19) 0.2731(2) 0.20881(11) 0.0718(6) Uani 1 1 d . . . H12 H 0.5624 0.2033 0.2367 0.086 Uiso 1 1 calc R . . C20 C 1.0844(2) 1.0663(4) 0.19215(13) 0.1043(10) Uani 1 1 d . . . H20A H 1.0493 1.1567 0.2089 0.125 Uiso 1 1 calc R . . H20B H 1.0857 0.9906 0.2310 0.125 Uiso 1 1 calc R . . C21 C 1.1918(3) 1.1025(4) 0.17603(16) 0.1183(12) Uani 1 1 d . . . H21A H 1.2264 1.0124 0.1598 0.177 Uiso 1 1 calc R . . H21B H 1.2308 1.1412 0.2196 0.177 Uiso 1 1 calc R . . H21C H 1.1900 1.1781 0.1379 0.177 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 0.0469(8) 0.0419(6) 0.0529(7) 0.0059(5) 0.0082(5) 0.0006(5) C24 0.0557(11) 0.0402(8) 0.0527(9) 0.0077(7) 0.0063(8) 0.0005(7) O4 0.0836(11) 0.0830(10) 0.0586(8) -0.0165(7) 0.0164(7) -0.0392(8) O3 0.0893(12) 0.1071(13) 0.0523(8) -0.0179(7) 0.0219(8) -0.0330(9) C17 0.0521(11) 0.0371(8) 0.0438(8) 0.0022(6) 0.0049(7) 0.0000(7) O2 0.0537(8) 0.0514(7) 0.0787(9) 0.0130(6) 0.0185(6) 0.0012(6) C8 0.0467(10) 0.0390(8) 0.0451(8) 0.0006(6) 0.0041(7) -0.0009(7) C7 0.0538(11) 0.0426(9) 0.0421(8) -0.0036(7) 0.0106(7) -0.0026(7) C6 0.0529(11) 0.0457(9) 0.0469(9) -0.0098(7) 0.0106(7) -0.0005(8) C18 0.0528(11) 0.0415(8) 0.0436(8) 0.0030(6) 0.0108(7) -0.0041(7) C9 0.0551(11) 0.0379(8) 0.0464(8) 0.0001(6) 0.0061(7) -0.0030(7) C16 0.0518(11) 0.0414(9) 0.0592(10) 0.0055(7) 0.0070(8) -0.0001(8) C14 0.0589(12) 0.0426(9) 0.0509(9) 0.0021(7) 0.0077(8) -0.0049(8) C19 0.0560(11) 0.0443(9) 0.0519(9) -0.0049(7) 0.0115(8) -0.0022(8) C10 0.0710(13) 0.0434(10) 0.0586(10) 0.0045(8) 0.0091(9) 0.0018(9) C13 0.0727(14) 0.0552(11) 0.0640(11) 0.0025(8) 0.0212(10) -0.0117(9) C1 0.0575(12) 0.0582(11) 0.0645(11) 0.0027(9) 0.0195(9) 0.0024(9) C2 0.0579(13) 0.0690(13) 0.0798(14) -0.0066(10) 0.0255(10) -0.0041(10) C5 0.0570(12) 0.0682(12) 0.0495(10) -0.0005(8) 0.0070(8) 0.0012(9) C4 0.0642(14) 0.0862(15) 0.0575(11) 0.0004(10) -0.0021(10) 0.0072(11) C11 0.0986(18) 0.0449(10) 0.0752(13) 0.0149(9) 0.0157(12) 0.0036(10) C3 0.0544(13) 0.0788(14) 0.0729(13) -0.0163(11) 0.0043(10) 0.0032(10) C23 0.0623(13) 0.0508(11) 0.0900(14) 0.0012(9) 0.0133(11) 0.0074(9) C22 0.0597(13) 0.0629(12) 0.0708(12) 0.0016(10) -0.0050(10) -0.0020(10) C12 0.0949(18) 0.0541(11) 0.0692(12) 0.0156(9) 0.0229(11) -0.0134(11) C20 0.114(2) 0.132(2) 0.0676(14) -0.0338(15) 0.0132(14) -0.0608(19) C21 0.112(3) 0.152(3) 0.0879(19) -0.0125(17) -0.0076(17) -0.053(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C8 1.4220(19) . ? O1 C7 1.4226(18) . ? C24 C17 1.531(2) . ? C24 C18 1.536(2) . ? O4 C19 1.321(2) . ? O4 C20 1.474(3) . ? O3 C19 1.192(2) . ? C17 C8 1.520(2) . ? C17 C16 1.525(2) . ? O2 C14 1.369(2) . ? O2 C16 1.4671(19) . ? C8 C9 1.498(2) . ? C7 C6 1.503(2) . ? C7 C18 1.551(2) . ? C6 C5 1.383(3) . ? C6 C1 1.391(2) . ? C18 C19 1.515(2) . ? C9 C14 1.392(2) . ? C9 C10 1.394(3) . ? C16 C23 1.516(2) . ? C16 C22 1.524(3) . ? C14 C13 1.394(2) . ? C10 C11 1.375(3) . ? C13 C12 1.370(3) . ? C1 C2 1.367(3) . ? C2 C3 1.375(3) . ? C5 C4 1.381(3) . ? C4 C3 1.379(3) . ? C11 C12 1.382(3) . ? C20 C21 1.435(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 C8 O1 C7 111.24(12) . . ? C17 C24 C18 112.27(13) . . ? C19 O4 C20 117.19(15) . . ? C8 C17 C16 110.39(13) . . ? C8 C17 C24 109.00(13) . . ? C16 C17 C24 114.84(13) . . ? C14 O2 C16 118.93(13) . . ? O1 C8 C9 109.47(13) . . ? O1 C8 C17 111.22(13) . . ? C9 C8 C17 110.07(13) . . ? O1 C7 C6 108.93(13) . . ? O1 C7 C18 110.77(12) . . ? C6 C7 C18 113.75(14) . . ? C5 C6 C1 117.99(17) . . ? C5 C6 C7 122.18(15) . . ? C1 C6 C7 119.84(16) . . ? C19 C18 C24 112.28(14) . . ? C19 C18 C7 111.20(14) . . ? C24 C18 C7 110.68(13) . . ? C14 C9 C10 118.42(15) . . ? C14 C9 C8 119.19(15) . . ? C10 C9 C8 122.39(16) . . ? O2 C16 C23 102.73(14) . . ? O2 C16 C22 107.43(14) . . ? C23 C16 C22 110.80(16) . . ? O2 C16 C17 108.33(13) . . ? C23 C16 C17 112.37(15) . . ? C22 C16 C17 114.37(14) . . ? O2 C14 C9 123.78(15) . . ? O2 C14 C13 115.93(17) . . ? C9 C14 C13 120.26(17) . . ? O3 C19 O4 123.21(17) . . ? O3 C19 C18 125.47(17) . . ? O4 C19 C18 111.31(14) . . ? C11 C10 C9 121.27(19) . . ? C12 C13 C14 119.9(2) . . ? C2 C1 C6 121.15(19) . . ? C1 C2 C3 120.62(19) . . ? C4 C5 C6 120.67(18) . . ? C3 C4 C5 120.5(2) . . ? C10 C11 C12 119.43(19) . . ? C2 C3 C4 119.0(2) . . ? C13 C12 C11 120.71(18) . . ? C21 C20 O4 109.1(2) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.199 _refine_diff_density_min -0.454 _refine_diff_density_rms 0.088