# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_samp48 _database_code_CSD 153781 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Ren-Wang Jiang' 'Shuang-Cheng Ma' 'Paul P. H. But' 'Thomas C. W. Mak' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common spirocaesalmin _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H34 O10' _chemical_formula_weight 494.52 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 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 11.8436(6) _cell_length_b 12.9482(6) _cell_length_c 16.3048(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2500.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.314 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1056 _exptl_absorpt_coefficient_mu 0.101 _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 12045 _diffrn_reflns_av_R_equivalents 0.0494 _diffrn_reflns_av_sigmaI/netI 0.0562 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 23.27 _reflns_number_total 3594 _reflns_number_gt 2598 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0472P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0040(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 -1.0(13) _refine_ls_number_reflns 3594 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0645 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0944 _refine_ls_wR_factor_gt 0.0838 _refine_ls_goodness_of_fit_ref 0.958 _refine_ls_restrained_S_all 0.958 _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 0.33395(17) 0.36894(16) -0.18939(12) 0.0458(6) Uani 1 1 d . . . O2 O 0.3804(2) 0.2568(2) -0.28780(17) 0.0816(8) Uani 1 1 d . . . O3 O 0.28769(16) 0.42668(14) -0.02985(14) 0.0432(5) Uani 1 1 d . . . H3A H 0.2695 0.4282 -0.0784 0.086(15) Uiso 1 1 calc R . . O4 O 0.41614(16) 0.28799(15) 0.17366(12) 0.0428(5) Uani 1 1 d . . . O5 O 0.2403(3) 0.3245(4) 0.20852(17) 0.1354(16) Uani 1 1 d . . . O6 O 0.5555(2) 0.05467(18) 0.12875(14) 0.0622(7) Uani 1 1 d . . . O7 O 0.3739(2) 0.03840(18) 0.16395(14) 0.0654(7) Uani 1 1 d . . . O8 O 0.4893(2) -0.10330(16) 0.00138(16) 0.0756(8) Uani 1 1 d . . . O9 O 0.3746(3) -0.0738(2) -0.11354(17) 0.0796(8) Uani 1 1 d . . . O10 O 0.2552(2) 0.0583(2) -0.09799(15) 0.0771(8) Uani 1 1 d . . . C1 C 0.4518(3) 0.3925(2) -0.17056(18) 0.0428(8) Uani 1 1 d . . . H1A H 0.5011 0.3495 -0.2046 0.051 Uiso 1 1 calc R . . C2 C 0.4708(3) 0.5057(2) -0.1916(2) 0.0536(9) Uani 1 1 d . . . H2A H 0.5507 0.5211 -0.1874 0.064 Uiso 1 1 calc R . . H2B H 0.4481 0.5176 -0.2480 0.064 Uiso 1 1 calc R . . C3 C 0.4058(3) 0.5785(2) -0.1362(2) 0.0567(10) Uani 1 1 d . . . H3B H 0.3258 0.5692 -0.1463 0.068 Uiso 1 1 calc R . . H3C H 0.4248 0.6489 -0.1511 0.068 Uiso 1 1 calc R . . C4 C 0.4279(3) 0.5644(2) -0.0440(2) 0.0508(9) Uani 1 1 d . . . C5 C 0.4077(2) 0.4471(2) -0.02246(18) 0.0373(7) Uani 1 1 d . . . C6 C 0.4292(3) 0.4211(2) 0.06779(17) 0.0394(8) Uani 1 1 d . . . H6A H 0.5092 0.4278 0.0795 0.047 Uiso 1 1 calc R . . H6B H 0.3888 0.4697 0.1023 0.047 Uiso 1 1 calc R . . C7 C 0.3910(3) 0.3120(2) 0.08777(16) 0.0360(7) Uani 1 1 d . . . H7A H 0.3095 0.3064 0.0786 0.043 Uiso 1 1 calc R . . C8 C 0.4515(2) 0.2339(2) 0.03445(16) 0.0335(7) Uani 1 1 d . . . H8A H 0.5324 0.2362 0.0469 0.040 Uiso 1 1 calc R . . C9 C 0.4345(2) 0.2593(2) -0.05622(16) 0.0322(7) Uani 1 1 d . . . H9A H 0.3531 0.2564 -0.0669 0.039 Uiso 1 1 calc R . . C10 C 0.4743(2) 0.3689(2) -0.07910(17) 0.0364(7) Uani 1 1 d . . . C11 C 0.4872(3) 0.1649(2) -0.09745(18) 0.0408(8) Uani 1 1 d . . . H11A H 0.5690 0.1695 -0.0975 0.049 Uiso 1 1 calc R . . H11B H 0.4609 0.1578 -0.1535 0.049 Uiso 1 1 calc R . . C12 C 0.3474(3) 0.0223(3) -0.0856(2) 0.0560(9) Uani 1 1 d . . . C13 C 0.4465(2) 0.0734(2) -0.04398(17) 0.0351(7) Uani 1 1 d . . . C14 C 0.4111(2) 0.1224(2) 0.04007(17) 0.0352(7) Uani 1 1 d . . . H14A H 0.3285 0.1224 0.0434 0.042 Uiso 1 1 calc R . . C15 C 0.5312(3) -0.0121(2) -0.04107(19) 0.0490(9) Uani 1 1 d . . . H15A H 0.6122 0.0025 -0.0438 0.059 Uiso 1 1 calc R . . C16 C 0.4834(4) -0.0988(3) -0.0843(3) 0.0730(12) Uani 1 1 d . . . H16A H 0.5326 -0.1433 -0.1172 0.088 Uiso 1 1 calc R . . C17 C 0.4571(3) 0.0668(2) 0.11408(19) 0.0429(8) Uani 1 1 d . . . C18 C 0.3411(3) 0.6313(3) 0.0021(2) 0.0686(11) Uani 1 1 d . . . H18A H 0.3536 0.7027 -0.0106 0.103 Uiso 1 1 calc R . . H18B H 0.3493 0.6208 0.0601 0.103 Uiso 1 1 calc R . . H18C H 0.2662 0.6119 -0.0144 0.103 Uiso 1 1 calc R . . C19 C 0.5458(3) 0.6050(3) -0.0208(2) 0.0710(11) Uani 1 1 d . . . H19A H 0.5515 0.6766 -0.0354 0.107 Uiso 1 1 calc R . . H19B H 0.6023 0.5663 -0.0497 0.107 Uiso 1 1 calc R . . H19C H 0.5571 0.5974 0.0372 0.107 Uiso 1 1 calc R . . C20 C 0.6040(2) 0.3745(2) -0.06880(19) 0.0464(8) Uani 1 1 d . . . H20A H 0.6234 0.3618 -0.0125 0.070 Uiso 1 1 calc R . . H20B H 0.6300 0.4419 -0.0845 0.070 Uiso 1 1 calc R . . H20C H 0.6390 0.3234 -0.1030 0.070 Uiso 1 1 calc R . . C21 C 0.3107(3) 0.3008(3) -0.2489(2) 0.0525(9) Uani 1 1 d . . . C22 C 0.1866(3) 0.2877(3) -0.2583(3) 0.0861(14) Uani 1 1 d . . . H22A H 0.1715 0.2391 -0.3013 0.129 Uiso 1 1 calc R . . H22B H 0.1530 0.3530 -0.2717 0.129 Uiso 1 1 calc R . . H22C H 0.1552 0.2627 -0.2078 0.129 Uiso 1 1 calc R . . C23 C 0.3318(4) 0.2964(3) 0.2273(2) 0.0618(10) Uani 1 1 d . . . C24 C 0.3670(3) 0.2681(3) 0.3128(2) 0.0730(12) Uani 1 1 d . . . H24A H 0.3038 0.2755 0.3492 0.109 Uiso 1 1 calc R . . H24B H 0.4269 0.3129 0.3302 0.109 Uiso 1 1 calc R . . H24C H 0.3928 0.1978 0.3136 0.109 Uiso 1 1 calc R . . C25 C 0.4103(4) -0.0096(3) 0.2406(2) 0.1023(16) Uani 1 1 d . . . H25A H 0.3452 -0.0280 0.2725 0.154 Uiso 1 1 calc R . . H25B H 0.4560 0.0383 0.2709 0.154 Uiso 1 1 calc R . . H25C H 0.4535 -0.0705 0.2287 0.154 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 0.0418(13) 0.0594(14) 0.0363(13) -0.0026(11) -0.0055(10) 0.0001(11) O2 0.0734(19) 0.093(2) 0.078(2) -0.0408(17) 0.0119(15) -0.0058(17) O3 0.0414(13) 0.0490(13) 0.0390(14) 0.0003(10) -0.0053(10) 0.0087(10) O4 0.0438(13) 0.0553(13) 0.0293(12) 0.0013(10) 0.0025(10) 0.0055(10) O5 0.067(2) 0.290(5) 0.0489(19) -0.013(2) 0.0052(15) 0.069(3) O6 0.0564(16) 0.0755(17) 0.0547(16) 0.0134(13) -0.0134(12) 0.0085(14) O7 0.0790(17) 0.0659(15) 0.0512(16) 0.0224(13) 0.0205(13) 0.0031(13) O8 0.118(2) 0.0388(14) 0.0698(19) 0.0103(12) 0.0191(17) 0.0049(14) O9 0.104(2) 0.0603(17) 0.0742(19) -0.0254(15) 0.0064(17) -0.0281(17) O10 0.0463(15) 0.127(2) 0.0581(17) -0.0226(16) -0.0097(13) -0.0084(17) C1 0.0424(19) 0.0485(19) 0.0375(19) 0.0015(15) 0.0002(16) -0.0007(16) C2 0.062(2) 0.054(2) 0.045(2) 0.0141(17) -0.0013(18) -0.0032(19) C3 0.071(2) 0.0409(19) 0.058(2) 0.0137(17) -0.0048(19) -0.0038(19) C4 0.066(2) 0.0368(18) 0.050(2) 0.0019(16) -0.0030(18) -0.0005(17) C5 0.0357(17) 0.0385(17) 0.0378(19) 0.0005(14) -0.0002(14) 0.0017(14) C6 0.0436(19) 0.0403(17) 0.0341(18) -0.0030(14) -0.0021(14) 0.0010(16) C7 0.0403(17) 0.0419(17) 0.0258(17) 0.0033(14) -0.0003(14) 0.0041(15) C8 0.0332(16) 0.0359(16) 0.0314(17) 0.0036(14) -0.0018(13) -0.0031(14) C9 0.0290(16) 0.0359(16) 0.0316(17) -0.0032(13) -0.0006(13) 0.0030(14) C10 0.0298(17) 0.0428(18) 0.0367(18) 0.0020(14) -0.0002(14) -0.0011(14) C11 0.0466(19) 0.0425(19) 0.0334(17) -0.0012(15) 0.0057(15) 0.0032(16) C12 0.058(2) 0.070(3) 0.040(2) -0.0106(19) 0.0081(19) -0.016(2) C13 0.0374(17) 0.0332(16) 0.0347(17) -0.0017(14) 0.0042(14) -0.0022(14) C14 0.0334(17) 0.0393(17) 0.0331(17) 0.0006(14) 0.0017(14) 0.0007(14) C15 0.058(2) 0.0385(18) 0.050(2) 0.0040(17) 0.0145(18) 0.0072(17) C16 0.101(4) 0.049(2) 0.069(3) -0.004(2) 0.019(3) 0.008(2) C17 0.055(2) 0.0351(17) 0.039(2) 0.0014(15) 0.0092(18) 0.0019(18) C18 0.102(3) 0.0354(18) 0.068(3) 0.0015(18) 0.001(2) 0.010(2) C19 0.084(3) 0.049(2) 0.080(3) 0.0025(19) -0.013(2) -0.019(2) C20 0.0372(18) 0.0475(19) 0.054(2) 0.0055(16) -0.0003(15) -0.0051(16) C21 0.064(3) 0.055(2) 0.039(2) 0.0039(19) 0.0011(19) -0.005(2) C22 0.057(3) 0.119(4) 0.083(3) -0.020(3) -0.016(2) -0.010(2) C23 0.054(2) 0.097(3) 0.035(2) -0.0083(19) 0.0062(19) 0.014(2) C24 0.078(3) 0.110(3) 0.032(2) 0.003(2) 0.0061(19) 0.012(2) C25 0.152(4) 0.095(3) 0.060(3) 0.047(3) 0.019(3) 0.014(3) _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 C21 1.341(4) . ? O1 C1 1.461(4) . ? O2 C21 1.186(4) . ? O3 C5 1.451(3) . ? O4 C23 1.333(4) . ? O4 C7 1.465(3) . ? O5 C23 1.184(4) . ? O6 C17 1.201(4) . ? O7 C17 1.329(4) . ? O7 C25 1.460(4) . ? O8 C16 1.399(5) . ? O8 C15 1.456(4) . ? O9 C12 1.364(4) . ? O9 C16 1.412(5) . ? O10 C12 1.204(4) . ? C1 C2 1.523(4) . ? C1 C10 1.545(4) . ? C2 C3 1.515(4) . ? C3 C4 1.537(4) . ? C4 C19 1.539(5) . ? C4 C18 1.541(5) . ? C4 C5 1.577(4) . ? C5 C6 1.531(4) . ? C5 C10 1.581(4) . ? C6 C7 1.518(4) . ? C7 C8 1.514(4) . ? C8 C14 1.524(4) . ? C8 C9 1.528(4) . ? C9 C11 1.529(4) . ? C9 C10 1.540(4) . ? C10 C20 1.547(4) . ? C11 C13 1.548(4) . ? C12 C13 1.509(4) . ? C13 C15 1.494(4) . ? C13 C14 1.567(4) . ? C14 C17 1.507(4) . ? C15 C16 1.440(5) . ? C21 C22 1.487(5) . ? C23 C24 1.499(5) . ? 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 C21 O1 C1 119.1(3) . . ? C23 O4 C7 117.3(2) . . ? C17 O7 C25 115.0(3) . . ? C16 O8 C15 60.6(2) . . ? C12 O9 C16 108.1(3) . . ? O1 C1 C2 107.2(2) . . ? O1 C1 C10 109.0(2) . . ? C2 C1 C10 112.5(3) . . ? C3 C2 C1 112.9(3) . . ? C2 C3 C4 115.0(3) . . ? C3 C4 C19 110.7(3) . . ? C3 C4 C18 107.2(3) . . ? C19 C4 C18 107.1(3) . . ? C3 C4 C5 107.9(2) . . ? C19 C4 C5 114.4(3) . . ? C18 C4 C5 109.3(3) . . ? O3 C5 C6 101.7(2) . . ? O3 C5 C4 107.8(2) . . ? C6 C5 C4 113.6(2) . . ? O3 C5 C10 108.9(2) . . ? C6 C5 C10 109.7(2) . . ? C4 C5 C10 114.3(2) . . ? C7 C6 C5 111.2(2) . . ? O4 C7 C8 108.1(2) . . ? O4 C7 C6 110.0(2) . . ? C8 C7 C6 110.9(2) . . ? C7 C8 C14 116.7(2) . . ? C7 C8 C9 110.5(2) . . ? C14 C8 C9 102.8(2) . . ? C8 C9 C11 101.5(2) . . ? C8 C9 C10 113.1(2) . . ? C11 C9 C10 120.3(2) . . ? C9 C10 C1 111.3(2) . . ? C9 C10 C20 108.7(2) . . ? C1 C10 C20 105.5(2) . . ? C9 C10 C5 107.2(2) . . ? C1 C10 C5 110.5(2) . . ? C20 C10 C5 113.7(2) . . ? C9 C11 C13 103.7(2) . . ? O10 C12 O9 120.7(4) . . ? O10 C12 C13 127.7(3) . . ? O9 C12 C13 111.5(3) . . ? C15 C13 C12 102.2(3) . . ? C15 C13 C11 112.1(2) . . ? C12 C13 C11 108.9(3) . . ? C15 C13 C14 116.9(2) . . ? C12 C13 C14 111.2(2) . . ? C11 C13 C14 105.4(2) . . ? C17 C14 C8 112.8(2) . . ? C17 C14 C13 114.2(2) . . ? C8 C14 C13 104.3(2) . . ? C16 C15 O8 57.8(2) . . ? C16 C15 C13 107.4(3) . . ? O8 C15 C13 112.8(3) . . ? O8 C16 O9 113.1(3) . . ? O8 C16 C15 61.7(2) . . ? O9 C16 C15 110.2(3) . . ? O6 C17 O7 124.2(3) . . ? O6 C17 C14 125.0(3) . . ? O7 C17 C14 110.8(3) . . ? O2 C21 O1 124.1(3) . . ? O2 C21 C22 125.4(4) . . ? O1 C21 C22 110.6(3) . . ? O5 C23 O4 122.8(3) . . ? O5 C23 C24 124.8(3) . . ? O4 C23 C24 112.5(3) . . ? 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 C21 O1 C1 C2 115.4(3) . . . . ? C21 O1 C1 C10 -122.6(3) . . . . ? O1 C1 C2 C3 66.9(3) . . . . ? C10 C1 C2 C3 -52.9(4) . . . . ? C1 C2 C3 C4 55.3(4) . . . . ? C2 C3 C4 C19 72.8(4) . . . . ? C2 C3 C4 C18 -170.7(3) . . . . ? C2 C3 C4 C5 -53.0(4) . . . . ? C3 C4 C5 O3 -69.3(3) . . . . ? C19 C4 C5 O3 167.0(3) . . . . ? C18 C4 C5 O3 47.0(3) . . . . ? C3 C4 C5 C6 178.8(2) . . . . ? C19 C4 C5 C6 55.1(4) . . . . ? C18 C4 C5 C6 -64.9(3) . . . . ? C3 C4 C5 C10 51.9(3) . . . . ? C19 C4 C5 C10 -71.8(3) . . . . ? C18 C4 C5 C10 168.2(3) . . . . ? O3 C5 C6 C7 55.5(3) . . . . ? C4 C5 C6 C7 171.1(2) . . . . ? C10 C5 C6 C7 -59.6(3) . . . . ? C23 O4 C7 C8 -139.7(3) . . . . ? C23 O4 C7 C6 99.1(3) . . . . ? C5 C6 C7 O4 178.1(2) . . . . ? C5 C6 C7 C8 58.5(3) . . . . ? O4 C7 C8 C14 66.8(3) . . . . ? C6 C7 C8 C14 -172.5(2) . . . . ? O4 C7 C8 C9 -176.4(2) . . . . ? C6 C7 C8 C9 -55.7(3) . . . . ? C7 C8 C9 C11 -172.6(2) . . . . ? C14 C8 C9 C11 -47.4(3) . . . . ? C7 C8 C9 C10 57.1(3) . . . . ? C14 C8 C9 C10 -177.7(2) . . . . ? C8 C9 C10 C1 -178.0(2) . . . . ? C11 C9 C10 C1 61.9(3) . . . . ? C8 C9 C10 C20 66.2(3) . . . . ? C11 C9 C10 C20 -53.9(3) . . . . ? C8 C9 C10 C5 -57.1(3) . . . . ? C11 C9 C10 C5 -177.1(2) . . . . ? O1 C1 C10 C9 51.2(3) . . . . ? C2 C1 C10 C9 169.9(3) . . . . ? O1 C1 C10 C20 168.9(2) . . . . ? C2 C1 C10 C20 -72.3(3) . . . . ? O1 C1 C10 C5 -67.8(3) . . . . ? C2 C1 C10 C5 50.9(3) . . . . ? O3 C5 C10 C9 -53.1(3) . . . . ? C6 C5 C10 C9 57.4(3) . . . . ? C4 C5 C10 C9 -173.7(2) . . . . ? O3 C5 C10 C1 68.4(3) . . . . ? C6 C5 C10 C1 178.9(2) . . . . ? C4 C5 C10 C1 -52.2(3) . . . . ? O3 C5 C10 C20 -173.3(2) . . . . ? C6 C5 C10 C20 -62.7(3) . . . . ? C4 C5 C10 C20 66.2(3) . . . . ? C8 C9 C11 C13 41.2(3) . . . . ? C10 C9 C11 C13 166.9(2) . . . . ? C16 O9 C12 O10 -175.1(3) . . . . ? C16 O9 C12 C13 7.7(4) . . . . ? O10 C12 C13 C15 175.5(3) . . . . ? O9 C12 C13 C15 -7.6(3) . . . . ? O10 C12 C13 C11 -65.7(4) . . . . ? O9 C12 C13 C11 111.2(3) . . . . ? O10 C12 C13 C14 50.0(4) . . . . ? O9 C12 C13 C14 -133.1(3) . . . . ? C9 C11 C13 C15 -148.0(2) . . . . ? C9 C11 C13 C12 99.6(3) . . . . ? C9 C11 C13 C14 -19.9(3) . . . . ? C7 C8 C14 C17 -79.9(3) . . . . ? C9 C8 C14 C17 159.1(2) . . . . ? C7 C8 C14 C13 155.6(2) . . . . ? C9 C8 C14 C13 34.6(3) . . . . ? C15 C13 C14 C17 -7.3(4) . . . . ? C12 C13 C14 C17 109.5(3) . . . . ? C11 C13 C14 C17 -132.6(3) . . . . ? C15 C13 C14 C8 116.2(3) . . . . ? C12 C13 C14 C8 -127.0(3) . . . . ? C11 C13 C14 C8 -9.0(3) . . . . ? C16 O8 C15 C13 96.8(3) . . . . ? C12 C13 C15 C16 4.5(3) . . . . ? C11 C13 C15 C16 -112.0(3) . . . . ? C14 C13 C15 C16 126.2(3) . . . . ? C12 C13 C15 O8 -57.1(3) . . . . ? C11 C13 C15 O8 -173.7(2) . . . . ? C14 C13 C15 O8 64.5(3) . . . . ? C15 O8 C16 O9 -101.3(3) . . . . ? C12 O9 C16 O8 62.3(4) . . . . ? C12 O9 C16 C15 -4.5(4) . . . . ? C13 C15 C16 O8 -106.4(3) . . . . ? O8 C15 C16 O9 106.0(3) . . . . ? C13 C15 C16 O9 -0.4(4) . . . . ? C25 O7 C17 O6 0.4(5) . . . . ? C25 O7 C17 C14 -175.8(3) . . . . ? C8 C14 C17 O6 -58.9(4) . . . . ? C13 C14 C17 O6 60.0(4) . . . . ? C8 C14 C17 O7 117.2(3) . . . . ? C13 C14 C17 O7 -123.9(3) . . . . ? C1 O1 C21 O2 0.6(5) . . . . ? C1 O1 C21 C22 179.9(3) . . . . ? C7 O4 C23 O5 -2.0(6) . . . . ? C7 O4 C23 C24 179.0(3) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 23.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.174 _refine_diff_density_min -0.154 _refine_diff_density_rms 0.033