# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Prof Richard Taylor' _publ_contact_author_address ; Department of Chemistry University of York Heslington York North Yorkshire YO10 5DD UNITED KINGDOM ; _publ_contact_author_email RJKT1@YORK.AC.UK _publ_section_title ; Unexpected Z-selectivity in the Ramberg-Backlund reaction of diarylsulfones leading to cis-stilbenes: the effect of aryl substituents and application in the synthesis of the integrastatin nucleus ; loop_ _publ_author_name R.Taylor 'Jonathan Foot' 'Gerard M.P.Giblin' 'Adrian C.Whitwood' data_rjt0303m _database_code_depnum_ccdc_archive 'CCDC 219622' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H16 O2' _chemical_formula_sum 'C17 H16 O2' _chemical_formula_weight 252.30 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 C2/c 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' '-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 19.3595(13) _cell_length_b 8.8441(6) _cell_length_c 16.7833(11) _cell_angle_alpha 90.00 _cell_angle_beta 115.7010(10) _cell_angle_gamma 90.00 _cell_volume 2589.3(3) _cell_formula_units_Z 8 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 5322 _cell_measurement_theta_min 2.58 _cell_measurement_theta_max 28.31 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.34 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1072 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.898 _exptl_absorpt_correction_T_max 0.980 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 9228 _diffrn_reflns_av_R_equivalents 0.0151 _diffrn_reflns_av_sigmaI/netI 0.0175 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 28.31 _reflns_number_total 3209 _reflns_number_gt 2861 _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^)+(0.0608P)^2^+1.2020P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3209 _refine_ls_number_parameters 174 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0421 _refine_ls_R_factor_gt 0.0383 _refine_ls_wR_factor_ref 0.1087 _refine_ls_wR_factor_gt 0.1048 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.09599(4) 0.05535(8) 0.10370(4) 0.02317(17) Uani 1 1 d . . . O2 O 0.09918(4) 0.09585(7) 0.24224(4) 0.02250(16) Uani 1 1 d . . . C10 C 0.19767(5) 0.20793(10) 0.21104(6) 0.0233(2) Uani 1 1 d . . . C7 C 0.04729(6) 0.38075(11) 0.17430(7) 0.0242(2) Uani 1 1 d . . . C15 C 0.16541(5) 0.12702(11) 0.13197(6) 0.0224(2) Uani 1 1 d . . . C3 C -0.04699(6) 0.27247(12) 0.03854(7) 0.0262(2) Uani 1 1 d . . . H3 H -0.0674 0.1874 0.0011 0.031 Uiso 1 1 calc R . . C14 C 0.20376(6) 0.11114(12) 0.07871(7) 0.0269(2) Uani 1 1 d . . . H14 H 0.1816 0.0536 0.0257 0.032 Uiso 1 1 calc R . . C1 C 0.05135(5) 0.09879(10) 0.15089(6) 0.02096(19) Uani 1 1 d . . . C9 C 0.15652(6) 0.21459(11) 0.27018(6) 0.0239(2) Uani 1 1 d . . . C2 C 0.01657(5) 0.25477(10) 0.12029(6) 0.0220(2) Uani 1 1 d . . . C16 C -0.00672(6) -0.02632(11) 0.13233(6) 0.0248(2) Uani 1 1 d . . . H16A H 0.0198 -0.1204 0.1594 0.037 Uiso 1 1 calc R . . H16B H -0.0352 -0.0404 0.0683 0.037 Uiso 1 1 calc R . . H16C H -0.0424 0.0007 0.1572 0.037 Uiso 1 1 calc R . . C5 C -0.05053(6) 0.53867(12) 0.06612(8) 0.0318(2) Uani 1 1 d . . . H5 H -0.0736 0.6352 0.0481 0.038 Uiso 1 1 calc R . . C8 C 0.11575(6) 0.36495(11) 0.26267(7) 0.0268(2) Uani 1 1 d . . . H8A H 0.0988 0.3722 0.3103 0.032 Uiso 1 1 calc R . . H8B H 0.1520 0.4488 0.2705 0.032 Uiso 1 1 calc R . . C4 C -0.08045(6) 0.41362(13) 0.01188(7) 0.0310(2) Uani 1 1 d . . . H4 H -0.1239 0.4247 -0.0435 0.037 Uiso 1 1 calc R . . C11 C 0.26835(6) 0.27871(12) 0.23365(7) 0.0295(2) Uani 1 1 d . . . H11 H 0.2907 0.3369 0.2864 0.035 Uiso 1 1 calc R . . C6 C 0.01304(6) 0.52208(11) 0.14642(7) 0.0291(2) Uani 1 1 d . . . H6 H 0.0337 0.6080 0.1831 0.035 Uiso 1 1 calc R . . C12 C 0.30635(6) 0.26537(12) 0.18054(8) 0.0322(2) Uani 1 1 d . . . H12 H 0.3542 0.3146 0.1967 0.039 Uiso 1 1 calc R . . C17 C 0.20927(6) 0.17804(13) 0.36620(7) 0.0314(2) Uani 1 1 d . . . H17A H 0.1793 0.1740 0.4005 0.047 Uiso 1 1 calc R . . H17B H 0.2486 0.2566 0.3905 0.047 Uiso 1 1 calc R . . H17C H 0.2339 0.0799 0.3694 0.047 Uiso 1 1 calc R . . C13 C 0.27449(6) 0.18002(13) 0.10371(7) 0.0308(2) Uani 1 1 d . . . H13 H 0.3012 0.1687 0.0681 0.037 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 0.0210(3) 0.0256(3) 0.0225(3) -0.0049(2) 0.0091(3) -0.0024(3) O2 0.0245(3) 0.0212(3) 0.0188(3) -0.0014(2) 0.0065(3) -0.0030(2) C10 0.0220(4) 0.0185(4) 0.0260(5) 0.0008(3) 0.0073(4) 0.0002(3) C7 0.0241(4) 0.0220(5) 0.0282(5) 0.0002(4) 0.0130(4) 0.0001(3) C15 0.0202(4) 0.0200(4) 0.0242(4) 0.0026(3) 0.0069(4) 0.0012(3) C3 0.0218(4) 0.0303(5) 0.0262(5) 0.0029(4) 0.0103(4) -0.0016(4) C14 0.0250(5) 0.0291(5) 0.0258(5) 0.0041(4) 0.0101(4) 0.0038(4) C1 0.0210(4) 0.0219(4) 0.0191(4) -0.0021(3) 0.0079(3) -0.0011(3) C9 0.0235(4) 0.0213(4) 0.0222(4) -0.0039(3) 0.0056(4) -0.0027(3) C2 0.0218(4) 0.0218(4) 0.0241(4) 0.0015(3) 0.0114(4) -0.0001(3) C16 0.0253(4) 0.0227(4) 0.0249(4) -0.0027(3) 0.0094(4) -0.0048(4) C5 0.0289(5) 0.0280(5) 0.0443(6) 0.0124(4) 0.0212(5) 0.0068(4) C8 0.0282(5) 0.0213(4) 0.0278(5) -0.0059(4) 0.0092(4) -0.0006(4) C4 0.0214(5) 0.0383(6) 0.0330(5) 0.0119(4) 0.0115(4) 0.0032(4) C11 0.0252(5) 0.0216(5) 0.0355(5) -0.0003(4) 0.0073(4) -0.0027(4) C6 0.0303(5) 0.0216(5) 0.0396(6) 0.0020(4) 0.0192(4) 0.0011(4) C12 0.0229(5) 0.0263(5) 0.0438(6) 0.0083(4) 0.0110(4) -0.0012(4) C17 0.0307(5) 0.0309(5) 0.0230(5) -0.0031(4) 0.0028(4) -0.0015(4) C13 0.0257(5) 0.0327(5) 0.0357(5) 0.0116(4) 0.0149(4) 0.0054(4) _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 C15 1.3712(11) . ? O1 C1 1.4544(11) . ? O2 C1 1.4061(11) . ? O2 C9 1.4503(11) . ? C10 C15 1.3945(13) . ? C10 C11 1.3992(14) . ? C10 C9 1.5195(14) . ? C7 C2 1.3962(13) . ? C7 C6 1.3970(14) . ? C7 C8 1.5068(14) . ? C15 C14 1.3947(14) . ? C3 C4 1.3881(14) . ? C3 C2 1.3988(13) . ? C3 H3 0.9500 . ? C14 C13 1.3871(15) . ? C14 H14 0.9500 . ? C1 C16 1.5105(13) . ? C1 C2 1.5232(13) . ? C9 C17 1.5222(13) . ? C9 C8 1.5235(14) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C5 C6 1.3836(16) . ? C5 C4 1.3892(16) . ? C5 H5 0.9500 . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C4 H4 0.9500 . ? C11 C12 1.3852(16) . ? C11 H11 0.9500 . ? C6 H6 0.9500 . ? C12 C13 1.3867(17) . ? C12 H12 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C13 H13 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C15 O1 C1 114.47(7) . . ? C1 O2 C9 112.89(7) . . ? C15 C10 C11 117.99(9) . . ? C15 C10 C9 119.76(8) . . ? C11 C10 C9 122.24(9) . . ? C2 C7 C6 119.33(9) . . ? C2 C7 C8 120.68(9) . . ? C6 C7 C8 119.98(9) . . ? O1 C15 C10 122.25(8) . . ? O1 C15 C14 116.49(8) . . ? C10 C15 C14 121.23(9) . . ? C4 C3 C2 120.39(10) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C13 C14 C15 119.47(10) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? O2 C1 O1 108.84(7) . . ? O2 C1 C16 106.90(7) . . ? O1 C1 C16 105.01(7) . . ? O2 C1 C2 111.73(7) . . ? O1 C1 C2 109.62(7) . . ? C16 C1 C2 114.41(8) . . ? O2 C9 C10 107.77(7) . . ? O2 C9 C17 104.86(8) . . ? C10 C9 C17 112.48(8) . . ? O2 C9 C8 107.99(8) . . ? C10 C9 C8 112.30(8) . . ? C17 C9 C8 111.01(8) . . ? C7 C2 C3 119.56(9) . . ? C7 C2 C1 120.15(8) . . ? C3 C2 C1 120.28(8) . . ? C1 C16 H16A 109.5 . . ? C1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C6 C5 C4 119.72(10) . . ? C6 C5 H5 120.1 . . ? C4 C5 H5 120.1 . . ? C7 C8 C9 111.43(8) . . ? C7 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? C7 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C3 C4 C5 120.07(10) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C12 C11 C10 121.15(10) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C5 C6 C7 120.91(10) . . ? C5 C6 H6 119.5 . . ? C7 C6 H6 119.5 . . ? C11 C12 C13 119.90(9) . . ? C11 C12 H12 120.0 . . ? C13 C12 H12 120.0 . . ? C9 C17 H17A 109.5 . . ? C9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C12 C13 C14 120.20(10) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? 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 C1 O1 C15 C10 13.55(12) . . . . ? C1 O1 C15 C14 -168.37(8) . . . . ? C11 C10 C15 O1 -179.23(8) . . . . ? C9 C10 C15 O1 1.80(14) . . . . ? C11 C10 C15 C14 2.79(14) . . . . ? C9 C10 C15 C14 -176.18(9) . . . . ? O1 C15 C14 C13 -179.63(9) . . . . ? C10 C15 C14 C13 -1.54(15) . . . . ? C9 O2 C1 O1 69.14(9) . . . . ? C9 O2 C1 C16 -177.93(7) . . . . ? C9 O2 C1 C2 -52.04(10) . . . . ? C15 O1 C1 O2 -47.16(10) . . . . ? C15 O1 C1 C16 -161.33(7) . . . . ? C15 O1 C1 C2 75.31(9) . . . . ? C1 O2 C9 C10 -51.49(10) . . . . ? C1 O2 C9 C17 -171.52(7) . . . . ? C1 O2 C9 C8 70.04(9) . . . . ? C15 C10 C9 O2 15.95(12) . . . . ? C11 C10 C9 O2 -162.97(8) . . . . ? C15 C10 C9 C17 131.05(9) . . . . ? C11 C10 C9 C17 -47.87(12) . . . . ? C15 C10 C9 C8 -102.86(10) . . . . ? C11 C10 C9 C8 78.22(11) . . . . ? C6 C7 C2 C3 1.20(14) . . . . ? C8 C7 C2 C3 -179.99(9) . . . . ? C6 C7 C2 C1 -177.86(8) . . . . ? C8 C7 C2 C1 0.95(14) . . . . ? C4 C3 C2 C7 -1.34(14) . . . . ? C4 C3 C2 C1 177.72(8) . . . . ? O2 C1 C2 C7 15.84(12) . . . . ? O1 C1 C2 C7 -104.90(9) . . . . ? C16 C1 C2 C7 137.48(9) . . . . ? O2 C1 C2 C3 -163.21(8) . . . . ? O1 C1 C2 C3 76.05(10) . . . . ? C16 C1 C2 C3 -41.58(12) . . . . ? C2 C7 C8 C9 15.97(13) . . . . ? C6 C7 C8 C9 -165.24(9) . . . . ? O2 C9 C8 C7 -48.47(11) . . . . ? C10 C9 C8 C7 70.21(10) . . . . ? C17 C9 C8 C7 -162.90(8) . . . . ? C2 C3 C4 C5 0.49(15) . . . . ? C6 C5 C4 C3 0.50(15) . . . . ? C15 C10 C11 C12 -1.85(15) . . . . ? C9 C10 C11 C12 177.09(9) . . . . ? C4 C5 C6 C7 -0.63(15) . . . . ? C2 C7 C6 C5 -0.23(15) . . . . ? C8 C7 C6 C5 -179.04(9) . . . . ? C10 C11 C12 C13 -0.34(16) . . . . ? C11 C12 C13 C14 1.66(16) . . . . ? C15 C14 C13 C12 -0.73(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.31 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.389 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.041 data_rjt0413m _database_code_depnum_ccdc_archive 'CCDC 257403' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H14 O3' _chemical_formula_sum 'C17 H14 O3' _chemical_formula_weight 266.28 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.2508(9) _cell_length_b 9.3130(9) _cell_length_c 15.5363(15) _cell_angle_alpha 100.325(2) _cell_angle_beta 90.360(2) _cell_angle_gamma 99.592(2) _cell_volume 1297.5(2) _cell_formula_units_Z 4 _cell_measurement_temperature 115(2) _cell_measurement_reflns_used 1679 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 23.23 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 560 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.916 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 115(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 10629 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0604 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.33 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4551 _reflns_number_gt 3241 _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^)+(0.0368P)^2^+0.3314P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4551 _refine_ls_number_parameters 365 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0713 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_ref 0.1019 _refine_ls_wR_factor_gt 0.0917 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4213(2) 0.7519(2) 0.34423(13) 0.0210(5) Uani 1 1 d . . . C2 C 0.4733(2) 0.7408(2) 0.43529(13) 0.0195(5) Uani 1 1 d . . . C3 C 0.5924(2) 0.6721(2) 0.44741(14) 0.0236(5) Uani 1 1 d . . . H3 H 0.6409 0.6299 0.3979 0.028 Uiso 1 1 calc R . . C4 C 0.6410(2) 0.6645(2) 0.53031(14) 0.0277(5) Uani 1 1 d . . . H4 H 0.7224 0.6171 0.5376 0.033 Uiso 1 1 calc R . . C5 C 0.5711(2) 0.7259(2) 0.60311(14) 0.0279(5) Uani 1 1 d . . . H5 H 0.6052 0.7213 0.6602 0.033 Uiso 1 1 calc R . . C6 C 0.4521(2) 0.7935(2) 0.59261(13) 0.0255(5) Uani 1 1 d . . . H6 H 0.4045 0.8356 0.6425 0.031 Uiso 1 1 calc R . . C7 C 0.4014(2) 0.8005(2) 0.50891(13) 0.0221(5) Uani 1 1 d . . . C8 C 0.2677(2) 0.8653(2) 0.49765(13) 0.0230(5) Uani 1 1 d . . . C9 C 0.2062(2) 0.8376(2) 0.40367(13) 0.0218(5) Uani 1 1 d . . . C10 C 0.1315(2) 0.6771(2) 0.38176(12) 0.0206(5) Uani 1 1 d . . . C11 C -0.0076(2) 0.6291(2) 0.41042(13) 0.0264(5) Uani 1 1 d . . . H11 H -0.0577 0.6985 0.4451 0.032 Uiso 1 1 calc R . . C12 C -0.0739(2) 0.4823(3) 0.38924(14) 0.0296(5) Uani 1 1 d . . . H12 H -0.1682 0.4509 0.4100 0.035 Uiso 1 1 calc R . . C13 C -0.0022(2) 0.3813(2) 0.33758(14) 0.0286(5) Uani 1 1 d . . . H13 H -0.0481 0.2806 0.3223 0.034 Uiso 1 1 calc R . . C14 C 0.1355(2) 0.4257(2) 0.30801(13) 0.0247(5) Uani 1 1 d . . . H14 H 0.1837 0.3564 0.2717 0.030 Uiso 1 1 calc R . . C15 C 0.2030(2) 0.5722(2) 0.33182(12) 0.0201(5) Uani 1 1 d . . . C16 C 0.5428(2) 0.7929(2) 0.28438(13) 0.0262(5) Uani 1 1 d . . . H16A H 0.5003 0.8042 0.2285 0.039 Uiso 1 1 calc R . . H16B H 0.6030 0.7148 0.2740 0.039 Uiso 1 1 calc R . . H16C H 0.6039 0.8866 0.3117 0.039 Uiso 1 1 calc R . . C17 C 0.1093(2) 0.9470(2) 0.38875(15) 0.0283(5) Uani 1 1 d . . . H17A H 0.1655 1.0478 0.4027 0.043 Uiso 1 1 calc R . . H17B H 0.0251 0.9385 0.4266 0.043 Uiso 1 1 calc R . . H17C H 0.0745 0.9258 0.3273 0.043 Uiso 1 1 calc R . . O1 O 0.32940(15) 0.85918(15) 0.34759(9) 0.0221(3) Uani 1 1 d . . . O2 O 0.34180(15) 0.60947(15) 0.30163(8) 0.0219(3) Uani 1 1 d . . . O3 O 0.20678(17) 0.92602(19) 0.55927(10) 0.0375(4) Uani 1 1 d . . . C18 C 0.2640(2) 0.9137(2) 1.07535(12) 0.0177(4) Uani 1 1 d . . . C19 C 0.1279(2) 0.7962(2) 1.07540(13) 0.0178(4) Uani 1 1 d . . . C20 C 0.0989(2) 0.7263(2) 1.14682(13) 0.0216(5) Uani 1 1 d . . . H20 H 0.1674 0.7479 1.1951 0.026 Uiso 1 1 calc R . . C21 C -0.0289(2) 0.6256(2) 1.14820(14) 0.0244(5) Uani 1 1 d . . . H21 H -0.0476 0.5788 1.1975 0.029 Uiso 1 1 calc R . . C22 C -0.1299(2) 0.5924(2) 1.07805(14) 0.0249(5) Uani 1 1 d . . . H22 H -0.2186 0.5251 1.0800 0.030 Uiso 1 1 calc R . . C23 C -0.1012(2) 0.6574(2) 1.00569(14) 0.0224(5) Uani 1 1 d . . . H23 H -0.1692 0.6333 0.9571 0.027 Uiso 1 1 calc R . . C24 C 0.0277(2) 0.7588(2) 1.00354(13) 0.0183(4) Uani 1 1 d . . . C25 C 0.0629(2) 0.8203(2) 0.92311(13) 0.0180(4) Uani 1 1 d . . . C26 C 0.2178(2) 0.9063(2) 0.92313(12) 0.0183(5) Uani 1 1 d . . . C27 C 0.3218(2) 0.7951(2) 0.90666(13) 0.0182(5) Uani 1 1 d . . . C28 C 0.3364(2) 0.7135(2) 0.82359(13) 0.0199(5) Uani 1 1 d . . . H28 H 0.2789 0.7265 0.7756 0.024 Uiso 1 1 calc R . . C29 C 0.4329(2) 0.6142(2) 0.80989(14) 0.0241(5) Uani 1 1 d . . . H29 H 0.4414 0.5591 0.7530 0.029 Uiso 1 1 calc R . . C30 C 0.5177(2) 0.5955(2) 0.87988(14) 0.0242(5) Uani 1 1 d . . . H30 H 0.5860 0.5291 0.8704 0.029 Uiso 1 1 calc R . . C31 C 0.5034(2) 0.6723(2) 0.96283(14) 0.0216(5) Uani 1 1 d . . . H31 H 0.5612 0.6587 1.0105 0.026 Uiso 1 1 calc R . . C32 C 0.4039(2) 0.7700(2) 0.97641(13) 0.0185(5) Uani 1 1 d . . . C33 C 0.2950(2) 1.0231(2) 1.15980(13) 0.0215(5) Uani 1 1 d . . . H33A H 0.3806 1.0978 1.1537 0.032 Uiso 1 1 calc R . . H33B H 0.3150 0.9711 1.2070 0.032 Uiso 1 1 calc R . . H33C H 0.2097 1.0716 1.1738 0.032 Uiso 1 1 calc R . . C34 C 0.2320(2) 1.0125(2) 0.85926(13) 0.0244(5) Uani 1 1 d . . . H34A H 0.1638 1.0825 0.8740 0.037 Uiso 1 1 calc R . . H34B H 0.2087 0.9568 0.7997 0.037 Uiso 1 1 calc R . . H34C H 0.3327 1.0671 0.8627 0.037 Uiso 1 1 calc R . . O4 O 0.25147(14) 0.99668(14) 1.00897(8) 0.0188(3) Uani 1 1 d . . . O5 O 0.39148(14) 0.84110(15) 1.06108(8) 0.0205(3) Uani 1 1 d . . . O6 O -0.02032(16) 0.79594(17) 0.85959(9) 0.0290(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0207(11) 0.0183(11) 0.0239(12) 0.0027(9) 0.0017(9) 0.0040(9) C2 0.0186(11) 0.0160(10) 0.0225(11) 0.0041(9) 0.0007(9) -0.0021(9) C3 0.0226(12) 0.0230(12) 0.0250(12) 0.0052(9) 0.0014(9) 0.0023(9) C4 0.0240(12) 0.0271(12) 0.0326(13) 0.0092(10) -0.0033(10) 0.0019(10) C5 0.0254(13) 0.0314(13) 0.0256(12) 0.0094(10) -0.0065(10) -0.0028(10) C6 0.0250(12) 0.0276(12) 0.0210(12) 0.0029(9) 0.0016(9) -0.0020(10) C7 0.0207(11) 0.0207(11) 0.0226(11) 0.0036(9) 0.0003(9) -0.0028(9) C8 0.0206(12) 0.0231(12) 0.0224(12) -0.0005(9) 0.0046(9) 0.0007(9) C9 0.0193(11) 0.0233(11) 0.0228(11) 0.0041(9) 0.0057(9) 0.0042(9) C10 0.0208(11) 0.0247(12) 0.0171(11) 0.0051(9) -0.0022(9) 0.0049(9) C11 0.0238(12) 0.0328(13) 0.0222(12) 0.0048(10) 0.0009(9) 0.0043(10) C12 0.0201(12) 0.0385(14) 0.0293(13) 0.0107(11) -0.0007(10) -0.0020(11) C13 0.0272(13) 0.0249(12) 0.0309(13) 0.0063(10) -0.0121(10) -0.0041(10) C14 0.0246(12) 0.0246(12) 0.0243(12) 0.0016(9) -0.0070(9) 0.0058(10) C15 0.0183(11) 0.0255(12) 0.0178(11) 0.0067(9) -0.0037(8) 0.0040(9) C16 0.0270(12) 0.0286(12) 0.0254(12) 0.0084(10) 0.0061(9) 0.0079(10) C17 0.0259(13) 0.0274(12) 0.0326(13) 0.0048(10) 0.0037(10) 0.0078(10) O1 0.0213(8) 0.0226(8) 0.0240(8) 0.0067(6) 0.0051(6) 0.0061(6) O2 0.0199(8) 0.0242(8) 0.0206(8) 0.0011(6) 0.0005(6) 0.0038(6) O3 0.0321(9) 0.0506(11) 0.0274(9) -0.0057(8) 0.0026(7) 0.0139(8) C18 0.0163(11) 0.0184(11) 0.0192(11) 0.0053(8) 0.0007(8) 0.0037(9) C19 0.0164(11) 0.0169(10) 0.0201(11) 0.0013(8) 0.0027(8) 0.0051(9) C20 0.0202(12) 0.0233(12) 0.0217(11) 0.0053(9) -0.0014(9) 0.0033(9) C21 0.0243(12) 0.0229(12) 0.0274(12) 0.0092(10) 0.0043(9) 0.0032(10) C22 0.0186(11) 0.0202(11) 0.0351(13) 0.0048(10) 0.0054(10) 0.0009(9) C23 0.0169(11) 0.0229(11) 0.0257(12) -0.0003(9) 0.0000(9) 0.0033(9) C24 0.0162(11) 0.0182(11) 0.0199(11) 0.0007(9) 0.0016(8) 0.0043(9) C25 0.0152(11) 0.0197(11) 0.0196(11) 0.0001(9) -0.0013(9) 0.0077(9) C26 0.0186(11) 0.0200(11) 0.0160(10) 0.0022(8) -0.0009(8) 0.0038(9) C27 0.0132(11) 0.0174(11) 0.0231(11) 0.0054(9) 0.0040(8) -0.0017(9) C28 0.0198(11) 0.0186(11) 0.0207(11) 0.0052(9) 0.0021(9) -0.0005(9) C29 0.0252(12) 0.0184(11) 0.0251(12) -0.0006(9) 0.0056(9) -0.0012(9) C30 0.0163(11) 0.0199(11) 0.0361(13) 0.0036(10) 0.0039(10) 0.0034(9) C31 0.0149(11) 0.0196(11) 0.0310(12) 0.0079(9) 0.0001(9) 0.0018(9) C32 0.0158(11) 0.0176(11) 0.0208(11) 0.0042(9) 0.0031(8) -0.0016(9) C33 0.0209(11) 0.0222(11) 0.0197(11) 0.0025(9) -0.0014(9) 0.0005(9) C34 0.0285(13) 0.0251(12) 0.0208(11) 0.0053(9) 0.0021(9) 0.0065(10) O4 0.0214(8) 0.0179(7) 0.0170(7) 0.0040(6) 0.0003(6) 0.0020(6) O5 0.0170(7) 0.0249(8) 0.0198(8) 0.0031(6) 0.0004(6) 0.0047(6) O6 0.0240(8) 0.0372(9) 0.0253(9) 0.0026(7) -0.0030(7) 0.0072(7) _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 O1 1.410(2) . ? C1 O2 1.446(2) . ? C1 C16 1.507(3) . ? C1 C2 1.518(3) . ? C2 C3 1.390(3) . ? C2 C7 1.401(3) . ? C3 C4 1.379(3) . ? C3 H3 0.9500 . ? C4 C5 1.387(3) . ? C4 H4 0.9500 . ? C5 C6 1.379(3) . ? C5 H5 0.9500 . ? C6 C7 1.395(3) . ? C6 H6 0.9500 . ? C7 C8 1.487(3) . ? C8 O3 1.213(2) . ? C8 C9 1.526(3) . ? C9 O1 1.448(2) . ? C9 C17 1.510(3) . ? C9 C10 1.516(3) . ? C10 C11 1.393(3) . ? C10 C15 1.394(3) . ? C11 C12 1.382(3) . ? C11 H11 0.9500 . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 C14 1.380(3) . ? C13 H13 0.9500 . ? C14 C15 1.386(3) . ? C14 H14 0.9500 . ? C15 O2 1.381(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 O4 1.410(2) . ? C18 O5 1.453(2) . ? C18 C33 1.503(3) . ? C18 C19 1.525(3) . ? C19 C20 1.389(3) . ? C19 C24 1.402(3) . ? C20 C21 1.384(3) . ? C20 H20 0.9500 . ? C21 C22 1.388(3) . ? C21 H21 0.9500 . ? C22 C23 1.377(3) . ? C22 H22 0.9500 . ? C23 C24 1.397(3) . ? C23 H23 0.9500 . ? C24 C25 1.481(3) . ? C25 O6 1.213(2) . ? C25 C26 1.521(3) . ? C26 O4 1.445(2) . ? C26 C34 1.514(3) . ? C26 C27 1.518(3) . ? C27 C32 1.395(3) . ? C27 C28 1.395(3) . ? C28 C29 1.380(3) . ? C28 H28 0.9500 . ? C29 C30 1.390(3) . ? C29 H29 0.9500 . ? C30 C31 1.376(3) . ? C30 H30 0.9500 . ? C31 C32 1.390(3) . ? C31 H31 0.9500 . ? C32 O5 1.377(2) . ? C33 H33A 0.9800 . ? C33 H33B 0.9800 . ? C33 H33C 0.9800 . ? C34 H34A 0.9800 . ? C34 H34B 0.9800 . ? C34 H34C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 O2 109.26(15) . . ? O1 C1 C16 106.32(16) . . ? O2 C1 C16 105.93(16) . . ? O1 C1 C2 111.32(16) . . ? O2 C1 C2 109.33(15) . . ? C16 C1 C2 114.44(17) . . ? C3 C2 C7 118.85(19) . . ? C3 C2 C1 121.03(18) . . ? C7 C2 C1 120.11(19) . . ? C4 C3 C2 120.9(2) . . ? C4 C3 H3 119.6 . . ? C2 C3 H3 119.6 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C6 C5 C4 120.0(2) . . ? C6 C5 H5 120.0 . . ? C4 C5 H5 120.0 . . ? C5 C6 C7 120.2(2) . . ? C5 C6 H6 119.9 . . ? C7 C6 H6 119.9 . . ? C6 C7 C2 119.9(2) . . ? C6 C7 C8 120.06(19) . . ? C2 C7 C8 120.00(18) . . ? O3 C8 C7 122.35(19) . . ? O3 C8 C9 122.8(2) . . ? C7 C8 C9 114.62(17) . . ? O1 C9 C17 106.32(16) . . ? O1 C9 C10 108.78(16) . . ? C17 C9 C10 114.04(17) . . ? O1 C9 C8 107.39(16) . . ? C17 C9 C8 112.73(17) . . ? C10 C9 C8 107.34(16) . . ? C11 C10 C15 118.01(19) . . ? C11 C10 C9 122.20(19) . . ? C15 C10 C9 119.78(18) . . ? C12 C11 C10 121.2(2) . . ? C12 C11 H11 119.4 . . ? C10 C11 H11 119.4 . . ? C11 C12 C13 119.6(2) . . ? C11 C12 H12 120.2 . . ? C13 C12 H12 120.2 . . ? C14 C13 C12 120.5(2) . . ? C14 C13 H13 119.7 . . ? C12 C13 H13 119.7 . . ? C13 C14 C15 119.4(2) . . ? C13 C14 H14 120.3 . . ? C15 C14 H14 120.3 . . ? O2 C15 C14 116.81(18) . . ? O2 C15 C10 121.98(18) . . ? C14 C15 C10 121.18(19) . . ? C1 C16 H16A 109.5 . . ? C1 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C1 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C9 C17 H17A 109.5 . . ? C9 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C9 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C1 O1 C9 113.86(15) . . ? C15 O2 C1 114.70(15) . . ? O4 C18 O5 109.47(15) . . ? O4 C18 C33 106.66(16) . . ? O5 C18 C33 106.46(15) . . ? O4 C18 C19 110.98(15) . . ? O5 C18 C19 108.87(15) . . ? C33 C18 C19 114.25(16) . . ? C20 C19 C24 118.74(18) . . ? C20 C19 C18 121.00(17) . . ? C24 C19 C18 120.24(17) . . ? C21 C20 C19 120.56(19) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C20 C21 C22 120.5(2) . . ? C20 C21 H21 119.8 . . ? C22 C21 H21 119.8 . . ? C23 C22 C21 119.8(2) . . ? C23 C22 H22 120.1 . . ? C21 C22 H22 120.1 . . ? C22 C23 C24 120.16(19) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C23 C24 C19 120.23(18) . . ? C23 C24 C25 119.84(18) . . ? C19 C24 C25 119.83(18) . . ? O6 C25 C24 123.25(19) . . ? O6 C25 C26 122.02(18) . . ? C24 C25 C26 114.53(17) . . ? O4 C26 C34 106.08(16) . . ? O4 C26 C27 109.05(15) . . ? C34 C26 C27 113.42(16) . . ? O4 C26 C25 107.88(15) . . ? C34 C26 C25 112.42(17) . . ? C27 C26 C25 107.81(16) . . ? C32 C27 C28 118.15(18) . . ? C32 C27 C26 119.71(17) . . ? C28 C27 C26 122.13(18) . . ? C29 C28 C27 121.16(19) . . ? C29 C28 H28 119.4 . . ? C27 C28 H28 119.4 . . ? C28 C29 C30 119.55(19) . . ? C28 C29 H29 120.2 . . ? C30 C29 H29 120.2 . . ? C31 C30 C29 120.5(2) . . ? C31 C30 H30 119.8 . . ? C29 C30 H30 119.8 . . ? C30 C31 C32 119.60(19) . . ? C30 C31 H31 120.2 . . ? C32 C31 H31 120.2 . . ? O5 C32 C31 117.12(17) . . ? O5 C32 C27 121.93(18) . . ? C31 C32 C27 120.95(19) . . ? C18 C33 H33A 109.5 . . ? C18 C33 H33B 109.5 . . ? H33A C33 H33B 109.5 . . ? C18 C33 H33C 109.5 . . ? H33A C33 H33C 109.5 . . ? H33B C33 H33C 109.5 . . ? C26 C34 H34A 109.5 . . ? C26 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C26 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? C18 O4 C26 113.46(14) . . ? C32 O5 C18 114.87(14) . . ? 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 O1 C1 C2 C3 -163.31(18) . . . . ? O2 C1 C2 C3 75.9(2) . . . . ? C16 C1 C2 C3 -42.7(3) . . . . ? O1 C1 C2 C7 16.6(3) . . . . ? O2 C1 C2 C7 -104.2(2) . . . . ? C16 C1 C2 C7 137.2(2) . . . . ? C7 C2 C3 C4 -1.0(3) . . . . ? C1 C2 C3 C4 178.87(18) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 0.5(3) . . . . ? C4 C5 C6 C7 0.1(3) . . . . ? C5 C6 C7 C2 -1.2(3) . . . . ? C5 C6 C7 C8 176.27(19) . . . . ? C3 C2 C7 C6 1.6(3) . . . . ? C1 C2 C7 C6 -178.26(18) . . . . ? C3 C2 C7 C8 -175.82(18) . . . . ? C1 C2 C7 C8 4.3(3) . . . . ? C6 C7 C8 O3 7.0(3) . . . . ? C2 C7 C8 O3 -175.5(2) . . . . ? C6 C7 C8 C9 -167.95(18) . . . . ? C2 C7 C8 C9 9.5(3) . . . . ? O3 C8 C9 O1 142.8(2) . . . . ? C7 C8 C9 O1 -42.2(2) . . . . ? O3 C8 C9 C17 26.0(3) . . . . ? C7 C8 C9 C17 -159.02(17) . . . . ? O3 C8 C9 C10 -100.4(2) . . . . ? C7 C8 C9 C10 74.6(2) . . . . ? O1 C9 C10 C11 -165.70(18) . . . . ? C17 C9 C10 C11 -47.2(3) . . . . ? C8 C9 C10 C11 78.4(2) . . . . ? O1 C9 C10 C15 14.7(2) . . . . ? C17 C9 C10 C15 133.2(2) . . . . ? C8 C9 C10 C15 -101.2(2) . . . . ? C15 C10 C11 C12 -0.8(3) . . . . ? C9 C10 C11 C12 179.66(19) . . . . ? C10 C11 C12 C13 -1.0(3) . . . . ? C11 C12 C13 C14 0.8(3) . . . . ? C12 C13 C14 C15 1.2(3) . . . . ? C13 C14 C15 O2 178.80(18) . . . . ? C13 C14 C15 C10 -3.0(3) . . . . ? C11 C10 C15 O2 -179.11(17) . . . . ? C9 C10 C15 O2 0.5(3) . . . . ? C11 C10 C15 C14 2.8(3) . . . . ? C9 C10 C15 C14 -177.64(18) . . . . ? O2 C1 O1 C9 66.78(19) . . . . ? C16 C1 O1 C9 -179.31(16) . . . . ? C2 C1 O1 C9 -54.1(2) . . . . ? C17 C9 O1 C1 -171.77(16) . . . . ? C10 C9 O1 C1 -48.6(2) . . . . ? C8 C9 O1 C1 67.3(2) . . . . ? C14 C15 O2 C1 -165.91(17) . . . . ? C10 C15 O2 C1 15.9(2) . . . . ? O1 C1 O2 C15 -47.7(2) . . . . ? C16 C1 O2 C15 -161.81(16) . . . . ? C2 C1 O2 C15 74.4(2) . . . . ? O4 C18 C19 C20 -164.04(17) . . . . ? O5 C18 C19 C20 75.4(2) . . . . ? C33 C18 C19 C20 -43.4(2) . . . . ? O4 C18 C19 C24 14.7(2) . . . . ? O5 C18 C19 C24 -105.89(19) . . . . ? C33 C18 C19 C24 135.28(19) . . . . ? C24 C19 C20 C21 -2.2(3) . . . . ? C18 C19 C20 C21 176.51(18) . . . . ? C19 C20 C21 C22 0.2(3) . . . . ? C20 C21 C22 C23 1.6(3) . . . . ? C21 C22 C23 C24 -1.3(3) . . . . ? C22 C23 C24 C19 -0.7(3) . . . . ? C22 C23 C24 C25 175.69(18) . . . . ? C20 C19 C24 C23 2.4(3) . . . . ? C18 C19 C24 C23 -176.30(17) . . . . ? C20 C19 C24 C25 -173.94(17) . . . . ? C18 C19 C24 C25 7.3(3) . . . . ? C23 C24 C25 O6 5.8(3) . . . . ? C19 C24 C25 O6 -177.85(19) . . . . ? C23 C24 C25 C26 -169.25(18) . . . . ? C19 C24 C25 C26 7.1(3) . . . . ? O6 C25 C26 O4 143.04(18) . . . . ? C24 C25 C26 O4 -41.9(2) . . . . ? O6 C25 C26 C34 26.4(3) . . . . ? C24 C25 C26 C34 -158.48(17) . . . . ? O6 C25 C26 C27 -99.3(2) . . . . ? C24 C25 C26 C27 75.8(2) . . . . ? O4 C26 C27 C32 14.7(2) . . . . ? C34 C26 C27 C32 132.70(19) . . . . ? C25 C26 C27 C32 -102.2(2) . . . . ? O4 C26 C27 C28 -166.65(17) . . . . ? C34 C26 C27 C28 -48.7(3) . . . . ? C25 C26 C27 C28 76.5(2) . . . . ? C32 C27 C28 C29 -2.2(3) . . . . ? C26 C27 C28 C29 179.19(19) . . . . ? C27 C28 C29 C30 -0.3(3) . . . . ? C28 C29 C30 C31 1.6(3) . . . . ? C29 C30 C31 C32 -0.4(3) . . . . ? C30 C31 C32 O5 178.40(17) . . . . ? C30 C31 C32 C27 -2.2(3) . . . . ? C28 C27 C32 O5 -177.21(17) . . . . ? C26 C27 C32 O5 1.5(3) . . . . ? C28 C27 C32 C31 3.4(3) . . . . ? C26 C27 C32 C31 -177.92(18) . . . . ? O5 C18 O4 C26 66.62(19) . . . . ? C33 C18 O4 C26 -178.58(15) . . . . ? C19 C18 O4 C26 -53.6(2) . . . . ? C34 C26 O4 C18 -171.37(16) . . . . ? C27 C26 O4 C18 -48.9(2) . . . . ? C25 C26 O4 C18 67.95(19) . . . . ? C31 C32 O5 C18 -166.13(16) . . . . ? C27 C32 O5 C18 14.5(3) . . . . ? O4 C18 O5 C32 -46.9(2) . . . . ? C33 C18 O5 C32 -161.78(15) . . . . ? C19 C18 O5 C32 74.61(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.302 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.043