# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry, 1999 # CCDC Number: 182/1304 data_y6 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C41 H28 O4' _chemical_formula_weight 584.63 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? 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 15.3590(10) _cell_length_b 19.181(2) _cell_length_c 10.6160(8) _cell_angle_alpha 90.00 _cell_angle_beta 101.1200(5) _cell_angle_gamma 90.00 _cell_volume 3068.8(4) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method ? _exptl_crystal_F_000 1224 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4368 _diffrn_reflns_av_R_equivalents 0.0873 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.58 _reflns_number_total 2584 _reflns_number_observed 2304 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 20 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1775P)^2^+1.3609P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0176(50) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2564 _refine_ls_number_parameters 230 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0928 _refine_ls_R_factor_obs 0.0807 _refine_ls_wR_factor_all 0.2543 _refine_ls_wR_factor_obs 0.2289 _refine_ls_goodness_of_fit_all 0.924 _refine_ls_goodness_of_fit_obs 0.930 _refine_ls_restrained_S_all 0.984 _refine_ls_restrained_S_obs 0.930 _refine_ls_shift/esd_max -0.175 _refine_ls_shift/esd_mean 0.031 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.3091(2) 0.39017(13) 0.5530(2) 0.1038(8) Uani 1 d . . O2 O 0.3262(2) 0.18488(12) 0.2201(2) 0.1040(8) Uani 1 d . . C1 C 0.3140(2) 0.34290(14) 0.4790(3) 0.0735(7) Uani 1 d . . C2 C 0.2645(2) 0.3440(2) 0.3466(3) 0.0839(9) Uani 1 d . . C3 C 0.2677(2) 0.2930(2) 0.2651(3) 0.0836(9) Uani 1 d . . C4 C 0.3231(2) 0.2307(2) 0.2986(3) 0.0765(8) Uani 1 d . . C5 C 0.4317(2) 0.17075(12) 0.4698(2) 0.0614(6) Uani 1 d . . C6 C 0.48130(15) 0.16491(10) 0.5935(2) 0.0551(6) Uani 1 d . . C7 C 0.47352(14) 0.21807(11) 0.6838(2) 0.0542(6) Uani 1 d . . C8 C 0.4188(2) 0.27516(12) 0.6442(2) 0.0590(6) Uani 1 d . . C9 C 0.37041(15) 0.28020(12) 0.5199(2) 0.0619(6) Uani 1 d . . C10 C 0.3761(2) 0.22691(12) 0.4316(2) 0.0622(6) Uani 1 d . . C11 C 0.54520(15) 0.10615(10) 0.6228(2) 0.0565(6) Uani 1 d . . C12 C 0.53688(15) 0.05445(10) 0.7137(2) 0.0562(6) Uani 1 d . . C13 C 0.5967(2) -0.00135(12) 0.7302(3) 0.0650(7) Uani 1 d . . C14 C 0.6636(2) -0.00600(14) 0.6607(3) 0.0738(8) Uani 1 d . . C15 C 0.6717(2) 0.0447(2) 0.5715(3) 0.0743(7) Uani 1 d . . C16 C 0.6121(2) 0.10017(13) 0.5524(2) 0.0636(7) Uani 1 d . . C17 C 1.0000 0.1732(4) 0.7500 0.118(2) Uani 1 d SD . H17 H 1.0000 0.2217(4) 0.7500 0.142 Uiso 1 calc SR . C18 C 0.9533(3) 0.1390(3) 0.6445(5) 0.1241(14) Uani 1 d D . C19 C 0.9513(5) 0.0665(4) 0.6498(9) 0.199(3) Uani 1 d D . H19 H 0.9163(5) 0.0414(4) 0.5840(9) 0.239 Uiso 1 calc R . C20 C 1.0000 0.0330(5) 0.7500 0.268(9) Uani 1 d SD . C21 C 1.0000 -0.0427(13) 0.7500 0.374(13) Uiso 1 d SD . H21A H 0.9625 -0.0594(13) 0.6729 0.562 Uiso 0.50 calc PR . H21B H 0.9781 -0.0594(13) 0.8233 0.562 Uiso 0.50 calc PR . H21C H 1.0594 -0.0594(13) 0.7538 0.562 Uiso 0.50 calc PR . C22 C 0.9003(4) 0.1765(3) 0.5307(5) 0.141(2) Uiso 1 d D . H22A H 0.9085(4) 0.2259(3) 0.5420(5) 0.211 Uiso 1 calc R . H22B H 0.8386(4) 0.1653(3) 0.5232(5) 0.211 Uiso 1 calc R . H22C H 0.9200(4) 0.1622(3) 0.4542(5) 0.211 Uiso 1 calc R . H2 H 0.2298(25) 0.3795(21) 0.3207(36) 0.100(10) Uiso 1 d . . H3 H 0.2370(25) 0.2974(19) 0.1898(39) 0.099(10) Uiso 1 d . . H5 H 0.4300(17) 0.1353(16) 0.4089(28) 0.070(7) Uiso 1 d . . H8 H 0.4150(17) 0.3105(15) 0.7075(27) 0.068(7) Uiso 1 d . . H13 H 0.5886(17) -0.0350(15) 0.7891(26) 0.067(7) Uiso 1 d . . H14 H 0.7001(20) -0.0440(17) 0.6745(30) 0.080(8) Uiso 1 d . . H15 H 0.7160(19) 0.0433(15) 0.5175(30) 0.075(8) Uiso 1 d . . H16 H 0.6127(19) 0.1329(17) 0.4944(31) 0.078(8) Uiso 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 O1 0.117(2) 0.0873(15) 0.102(2) -0.0040(13) 0.0084(13) 0.0452(13) O2 0.138(2) 0.0891(15) 0.0679(13) -0.0048(11) -0.0222(12) 0.0151(14) C1 0.074(2) 0.0648(15) 0.082(2) 0.0101(14) 0.0154(13) 0.0174(12) C2 0.075(2) 0.082(2) 0.090(2) 0.027(2) 0.0048(14) 0.0213(15) C3 0.082(2) 0.089(2) 0.072(2) 0.016(2) -0.0046(14) 0.0124(15) C4 0.084(2) 0.073(2) 0.066(2) 0.0077(13) -0.0023(12) 0.0026(13) C5 0.0762(14) 0.0488(11) 0.0551(13) 0.0002(10) 0.0024(10) -0.0006(10) C6 0.0640(12) 0.0445(10) 0.0545(12) 0.0014(9) 0.0057(9) -0.0013(9) C7 0.0619(12) 0.0454(11) 0.0542(12) 0.0026(9) 0.0084(9) -0.0016(8) C8 0.0690(13) 0.0474(11) 0.0600(13) 0.0012(10) 0.0107(10) 0.0044(9) C9 0.0630(12) 0.0558(12) 0.0653(14) 0.0079(10) 0.0085(10) 0.0053(10) C10 0.0686(13) 0.0558(12) 0.0586(13) 0.0057(10) 0.0032(10) 0.0001(10) C11 0.0680(13) 0.0454(11) 0.0516(11) -0.0060(9) 0.0000(9) -0.0008(9) C12 0.0673(13) 0.0420(10) 0.0543(12) -0.0039(8) -0.0011(9) -0.0008(8) C13 0.0800(15) 0.0466(12) 0.0630(13) -0.0030(10) 0.0001(11) 0.0060(10) C14 0.079(2) 0.0603(14) 0.077(2) -0.0118(12) 0.0005(13) 0.0159(12) C15 0.074(2) 0.075(2) 0.073(2) -0.0184(13) 0.0135(13) 0.0059(12) C16 0.0713(14) 0.0606(13) 0.0576(13) -0.0039(11) 0.0093(11) -0.0006(11) C17 0.103(4) 0.124(5) 0.135(5) 0.000 0.041(4) 0.000 C18 0.113(3) 0.120(3) 0.143(4) 0.008(3) 0.036(3) -0.003(2) C19 0.217(7) 0.141(5) 0.206(7) 0.010(5) -0.040(6) 0.017(5) C20 0.337(17) 0.081(5) 0.304(16) 0.000 -0.140(14) 0.000 _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 1.212(4) . ? O2 C4 1.218(3) . ? C1 C2 1.463(4) . ? C1 C9 1.497(3) . ? C2 C3 1.312(5) . ? C3 C4 1.471(4) . ? C4 C10 1.490(4) . ? C5 C6 1.390(3) . ? C5 C10 1.386(3) . ? C6 C7 1.420(3) . ? C6 C11 1.487(3) . ? C7 C8 1.395(3) . ? C7 C7 1.482(4) 2_656 ? C8 C9 1.388(3) . ? C9 C10 1.401(4) . ? C11 C16 1.387(3) . ? C11 C12 1.407(3) . ? C12 C13 1.400(3) . ? C12 C12 1.487(5) 2_656 ? C13 C14 1.379(4) . ? C14 C15 1.379(4) . ? C15 C16 1.393(4) . ? C17 C18 1.374(6) . ? C17 C18 1.374(6) 2_756 ? C18 C19 1.393(9) . ? C18 C22 1.504(7) . ? C19 C20 1.340(8) . ? C20 C19 1.340(8) 2_756 ? C20 C21 1.45(2) . ? 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 C2 121.8(2) . . ? O1 C1 C9 121.2(3) . . ? C2 C1 C9 117.0(2) . . ? C3 C2 C1 123.0(3) . . ? C2 C3 C4 122.6(3) . . ? O2 C4 C3 121.2(3) . . ? O2 C4 C10 121.8(2) . . ? C3 C4 C10 117.0(3) . . ? C6 C5 C10 122.2(2) . . ? C5 C6 C7 118.5(2) . . ? C5 C6 C11 118.5(2) . . ? C7 C6 C11 122.8(2) . . ? C8 C7 C6 119.0(2) . . ? C8 C7 C7 118.3(2) . 2_656 ? C6 C7 C7 122.5(2) . 2_656 ? C9 C8 C7 121.5(2) . . ? C8 C9 C10 119.6(2) . . ? C8 C9 C1 120.4(2) . . ? C10 C9 C1 120.0(2) . . ? C5 C10 C9 119.1(2) . . ? C5 C10 C4 120.6(2) . . ? C9 C10 C4 120.3(2) . . ? C16 C11 C12 119.1(2) . . ? C16 C11 C6 118.5(2) . . ? C12 C11 C6 122.3(2) . . ? C13 C12 C11 118.7(2) . . ? C13 C12 C12 118.9(2) . 2_656 ? C11 C12 C12 122.3(2) . 2_656 ? C14 C13 C12 121.5(3) . . ? C13 C14 C15 119.8(2) . . ? C14 C15 C16 119.7(3) . . ? C11 C16 C15 121.2(3) . . ? C18 C17 C18 123.0(7) . 2_756 ? C19 C18 C17 117.1(6) . . ? C19 C18 C22 119.8(6) . . ? C17 C18 C22 122.9(5) . . ? C20 C19 C18 119.8(8) . . ? C19 C20 C19 122.8(9) 2_756 . ? C19 C20 C21 118.6(5) 2_756 . ? C19 C20 C21 118.6(5) . . ? _refine_diff_density_max 0.354 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.051 data_ya10 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C38 H30 O4' _chemical_formula_weight 550.62 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? 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 15.807(2) _cell_length_b 18.590(3) _cell_length_c 10.590(2) _cell_angle_alpha 90.00 _cell_angle_beta 100.550(11) _cell_angle_gamma 90.00 _cell_volume 3059.3(8) _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 ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.195 _exptl_crystal_density_method ? _exptl_crystal_F_000 1160 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4254 _diffrn_reflns_av_R_equivalents 0.0512 _diffrn_reflns_av_sigmaI/netI 0.0644 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.61 _reflns_number_total 2386 _reflns_number_observed 2109 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 5 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1994P)^2^+1.8868P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0152(31) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2381 _refine_ls_number_parameters 191 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0732 _refine_ls_R_factor_obs 0.0632 _refine_ls_wR_factor_all 0.2095 _refine_ls_wR_factor_obs 0.1906 _refine_ls_goodness_of_fit_all 0.731 _refine_ls_goodness_of_fit_obs 0.710 _refine_ls_restrained_S_all 0.736 _refine_ls_restrained_S_obs 0.710 _refine_ls_shift/esd_max 0.238 _refine_ls_shift/esd_mean 0.033 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.2992(2) 0.38682(12) 0.5585(2) 0.1057(8) Uani 1 d . . O2 O 0.3496(2) 0.19120(13) 0.2131(2) 0.1103(9) Uani 1 d . . C1 C 0.3116(2) 0.34118(14) 0.4820(3) 0.0736(7) Uani 1 d . . C2 C 0.2651(2) 0.3428(2) 0.3477(3) 0.0869(8) Uani 1 d . . H2 H 0.2272(2) 0.3810(2) 0.3240(3) 0.120 Uiso 1 d R . C3 C 0.2783(2) 0.2940(2) 0.2621(3) 0.0891(9) Uani 1 d . . H3 H 0.2417(2) 0.2953(2) 0.1834(3) 0.120 Uiso 1 d R . C4 C 0.3385(2) 0.23464(15) 0.2941(3) 0.0774(7) Uani 1 d . . C5 C 0.44330(15) 0.17365(11) 0.4664(2) 0.0615(6) Uani 1 d . . H5 H 0.45008(15) 0.13810(11) 0.4068(2) 0.120 Uiso 1 d R . C6 C 0.48721(13) 0.16715(10) 0.5921(2) 0.0529(5) Uani 1 d . . C7 C 0.47492(14) 0.21992(11) 0.6830(2) 0.0542(5) Uani 1 d . . C8 C 0.41868(14) 0.27626(11) 0.6447(2) 0.0598(6) Uani 1 d . . H8 H 0.40983(14) 0.31119(11) 0.7043(2) 0.080 Uiso 1 d R . C9 C 0.37312(14) 0.28133(12) 0.5194(2) 0.0609(6) Uani 1 d . . C10 C 0.38627(15) 0.22972(12) 0.4290(2) 0.0606(6) Uani 1 d . . C11 C 0.54898(14) 0.10622(11) 0.6255(2) 0.0540(5) Uani 1 d . . C12 C 0.53742(13) 0.05401(10) 0.7160(2) 0.0527(5) Uani 1 d . . C13 C 0.59504(15) -0.00368(11) 0.7370(2) 0.0611(6) Uani 1 d . . H13 H 0.58934(15) -0.03871(11) 0.7980(2) 0.080 Uiso 1 d R . C14 C 0.6621(2) -0.00990(13) 0.6712(2) 0.0690(7) Uani 1 d . . H14 H 0.6994(2) -0.04928(13) 0.6835(2) 0.080 Uiso 1 d R . C15 C 0.6724(2) 0.04101(14) 0.5812(2) 0.0694(7) Uani 1 d . . H15 H 0.7179(2) 0.03835(14) 0.5354(2) 0.080 Uiso 1 d R . C16 C 0.61661(14) 0.09896(12) 0.5585(2) 0.0609(6) Uani 1 d . . H16 H 0.62285(14) 0.13359(12) 0.4970(2) 0.080 Uiso 1 d R . C17 C 0.6115(7) 0.3665(7) 0.5075(11) 0.300(6) Uani 1 d D . H17A H 0.6643(7) 0.3544(7) 0.5640(11) 0.450 Uiso 1 calc R . H17B H 0.6210(7) 0.3679(7) 0.4206(11) 0.450 Uiso 1 calc R . H17C H 0.5687(7) 0.3308(7) 0.5148(11) 0.450 Uiso 1 calc R . C18 C 0.5833(9) 0.4332(8) 0.5409(26) 0.420(13) Uani 1 d D . H18A H 0.5782(9) 0.4292(8) 0.6305(26) 0.504 Uiso 1 calc R . H18B H 0.6308(9) 0.4660(8) 0.5385(26) 0.504 Uiso 1 calc R . C19 C 0.5154(8) 0.4667(5) 0.4856(16) 0.319(8) Uani 1 d D . H19A H 0.4684(8) 0.4335(5) 0.4886(16) 0.383 Uiso 1 calc R . H19B H 0.5207(8) 0.4697(5) 0.3960(16) 0.383 Uiso 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 0.127(2) 0.099(2) 0.0898(13) -0.0047(11) 0.0151(12) 0.0555(13) O2 0.158(2) 0.100(2) 0.0598(11) -0.0112(10) -0.0160(12) 0.0406(14) C1 0.0790(15) 0.0668(15) 0.076(2) 0.0083(12) 0.0168(13) 0.0172(12) C2 0.088(2) 0.086(2) 0.082(2) 0.0174(15) 0.0016(14) 0.0256(15) C3 0.101(2) 0.085(2) 0.073(2) 0.0126(14) -0.0069(15) 0.021(2) C4 0.095(2) 0.071(2) 0.0609(14) 0.0036(12) 0.0014(13) 0.0080(13) C5 0.0794(14) 0.0506(11) 0.0520(11) -0.0014(9) 0.0057(10) 0.0014(10) C6 0.0638(11) 0.0439(10) 0.0501(10) 0.0007(8) 0.0081(9) -0.0017(8) C7 0.0650(12) 0.0458(10) 0.0518(11) 0.0018(8) 0.0108(10) -0.0027(9) C8 0.0731(13) 0.0504(11) 0.0560(12) -0.0008(9) 0.0123(10) 0.0039(10) C9 0.0672(13) 0.0544(12) 0.0605(12) 0.0066(9) 0.0100(11) 0.0053(10) C10 0.0718(13) 0.0547(12) 0.0529(11) 0.0041(9) 0.0050(10) 0.0029(10) C11 0.0643(11) 0.0468(10) 0.0491(10) -0.0046(8) 0.0060(9) -0.0001(9) C12 0.0627(11) 0.0436(10) 0.0494(10) -0.0041(8) 0.0037(9) 0.0007(8) C13 0.0717(13) 0.0485(11) 0.0596(12) -0.0011(9) 0.0027(10) 0.0048(9) C14 0.0715(14) 0.0607(13) 0.0720(14) -0.0085(11) 0.0053(12) 0.0147(11) C15 0.0675(13) 0.074(2) 0.0678(14) -0.0125(12) 0.0146(12) 0.0040(11) C16 0.0689(13) 0.0601(13) 0.0531(11) -0.0043(9) 0.0097(10) -0.0020(10) C17 0.283(10) 0.281(12) 0.385(15) 0.106(12) 0.192(11) 0.023(11) C18 0.297(16) 0.247(13) 0.760(38) 0.143(19) 0.214(20) 0.114(12) C19 0.256(11) 0.222(12) 0.520(22) 0.107(15) 0.183(13) 0.059(10) _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 1.213(3) . ? O2 C4 1.214(3) . ? C1 C2 1.477(4) . ? C1 C9 1.483(3) . ? C2 C3 1.327(4) . ? C3 C4 1.456(4) . ? C4 C10 1.492(3) . ? C5 C6 1.389(3) . ? C5 C10 1.388(3) . ? C6 C7 1.413(3) . ? C6 C11 1.495(3) . ? C7 C8 1.386(3) . ? C7 C7 1.493(4) 2_656 ? C8 C9 1.393(3) . ? C9 C10 1.397(3) . ? C11 C16 1.394(3) . ? C11 C12 1.399(3) . ? C12 C13 1.398(3) . ? C12 C12 1.493(4) 2_656 ? C13 C14 1.376(4) . ? C14 C15 1.373(4) . ? C15 C16 1.386(3) . ? C17 C18 1.39(2) . ? C18 C19 1.29(2) . ? C19 C19 1.39(2) 5_666 ? 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 C2 121.1(2) . . ? O1 C1 C9 121.6(2) . . ? C2 C1 C9 117.3(2) . . ? C3 C2 C1 122.1(2) . . ? C2 C3 C4 122.5(3) . . ? O2 C4 C3 120.8(2) . . ? O2 C4 C10 121.5(2) . . ? C3 C4 C10 117.7(2) . . ? C6 C5 C10 121.6(2) . . ? C5 C6 C7 119.1(2) . . ? C5 C6 C11 118.8(2) . . ? C7 C6 C11 122.0(2) . . ? C8 C7 C6 119.1(2) . . ? C8 C7 C7 118.6(2) . 2_656 ? C6 C7 C7 122.1(2) . 2_656 ? C9 C8 C7 121.5(2) . . ? C8 C9 C10 119.4(2) . . ? C8 C9 C1 120.3(2) . . ? C10 C9 C1 120.3(2) . . ? C5 C10 C9 119.4(2) . . ? C5 C10 C4 120.5(2) . . ? C9 C10 C4 120.1(2) . . ? C16 C11 C12 119.3(2) . . ? C16 C11 C6 118.8(2) . . ? C12 C11 C6 121.7(2) . . ? C13 C12 C11 118.5(2) . . ? C13 C12 C12 118.3(2) . 2_656 ? C11 C12 C12 123.0(2) . 2_656 ? C14 C13 C12 121.6(2) . . ? C13 C14 C15 119.6(2) . . ? C16 C15 C14 120.2(2) . . ? C15 C16 C11 120.7(2) . . ? C19 C18 C17 126.7(22) . . ? C18 C19 C19 129.1(22) . 5_666 ? 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 179.2(3) . . . . ? C9 C1 C2 C3 -1.3(5) . . . . ? C1 C2 C3 C4 0.8(5) . . . . ? C2 C3 C4 O2 -179.3(3) . . . . ? C2 C3 C4 C10 0.1(5) . . . . ? C10 C5 C6 C7 -1.5(3) . . . . ? C10 C5 C6 C11 -178.9(2) . . . . ? C5 C6 C7 C8 0.7(3) . . . . ? C11 C6 C7 C8 178.0(2) . . . . ? C5 C6 C7 C7 -174.9(2) . . . 2_656 ? C11 C6 C7 C7 2.3(3) . . . 2_656 ? C6 C7 C8 C9 1.0(3) . . . . ? C7 C7 C8 C9 176.8(2) 2_656 . . . ? C7 C8 C9 C10 -2.0(4) . . . . ? C7 C8 C9 C1 178.3(2) . . . . ? O1 C1 C9 C8 0.0(4) . . . . ? C2 C1 C9 C8 -179.6(2) . . . . ? O1 C1 C9 C10 -179.7(3) . . . . ? C2 C1 C9 C10 0.8(4) . . . . ? C6 C5 C10 C9 0.6(3) . . . . ? C6 C5 C10 C4 -178.7(2) . . . . ? C8 C9 C10 C5 1.2(3) . . . . ? C1 C9 C10 C5 -179.1(2) . . . . ? C8 C9 C10 C4 -179.5(2) . . . . ? C1 C9 C10 C4 0.1(4) . . . . ? O2 C4 C10 C5 -1.9(4) . . . . ? C3 C4 C10 C5 178.7(2) . . . . ? O2 C4 C10 C9 178.9(3) . . . . ? C3 C4 C10 C9 -0.6(4) . . . . ? C5 C6 C11 C16 57.1(3) . . . . ? C7 C6 C11 C16 -120.1(2) . . . . ? C5 C6 C11 C12 -118.7(2) . . . . ? C7 C6 C11 C12 64.0(3) . . . . ? C16 C11 C12 C13 0.6(3) . . . . ? C6 C11 C12 C13 176.4(2) . . . . ? C16 C11 C12 C12 -174.6(2) . . . 2_656 ? C6 C11 C12 C12 1.2(3) . . . 2_656 ? C11 C12 C13 C14 0.1(3) . . . . ? C12 C12 C13 C14 175.5(2) 2_656 . . . ? C12 C13 C14 C15 -0.9(3) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C14 C15 C16 C11 -0.5(3) . . . . ? C12 C11 C16 C15 -0.4(3) . . . . ? C6 C11 C16 C15 -176.3(2) . . . . ? C17 C18 C19 C19 -179.5(16) . . . 5_666 ? _refine_diff_density_max 0.186 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.041 data_y13 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C34 H20 O6' _chemical_formula_weight 524.50 _chemical_melting_point ? _chemical_compound_source ? 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 9.345(2) _cell_length_b 10.121(3) _cell_length_c 14.498(3) _cell_angle_alpha 98.648(10) _cell_angle_beta 101.230(13) _cell_angle_gamma 101.230(13) _cell_volume 1293.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method ? _exptl_crystal_F_000 544 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3480 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0688 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.46 _diffrn_reflns_theta_max 25.67 _reflns_number_total 3480 _reflns_number_observed 2906 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 13 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0518(84) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3467 _refine_ls_number_parameters 430 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0829 _refine_ls_R_factor_obs 0.0687 _refine_ls_wR_factor_all 0.2020 _refine_ls_wR_factor_obs 0.1858 _refine_ls_goodness_of_fit_all 1.269 _refine_ls_goodness_of_fit_obs 1.314 _refine_ls_restrained_S_all 1.300 _refine_ls_restrained_S_obs 1.314 _refine_ls_shift/esd_max -0.241 _refine_ls_shift/esd_mean 0.015 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O -0.2802(3) 0.4813(3) 0.4228(2) 0.0909(9) Uani 1 d . . O2 O 0.1584(3) 0.8316(3) 0.6923(2) 0.0948(9) Uani 1 d . . O3 O -0.3680(3) 0.9582(3) 0.1078(2) 0.0880(8) Uani 1 d . . O4 O -0.0226(3) 0.7885(3) -0.1160(2) 0.0867(8) Uani 1 d . . O5 O 0.6791(6) 0.5220(5) 0.0820(4) 0.174(2) Uani 1 d . . O6 O 0.4872(5) 0.3509(4) 0.0273(3) 0.148(2) Uani 1 d . . C1 C -0.1796(4) 0.5636(4) 0.4834(2) 0.0652(8) Uani 1 d . . C2 C -0.1593(5) 0.5564(4) 0.5856(3) 0.0762(10) Uani 1 d . . C3 C -0.0501(4) 0.6442(4) 0.6526(3) 0.0739(10) Uani 1 d . . C4 C 0.0606(4) 0.7522(4) 0.6299(2) 0.0691(9) Uani 1 d . . C5 C 0.1516(4) 0.8551(4) 0.5002(2) 0.0600(8) Uani 1 d . . C6 C 0.1421(3) 0.8657(3) 0.4047(2) 0.0545(7) Uani 1 d . . C7 C 0.0169(3) 0.7829(3) 0.3345(2) 0.0537(7) Uani 1 d . . C8 C -0.0878(4) 0.6884(3) 0.3616(2) 0.0561(7) Uani 1 d . . C9 C -0.0733(3) 0.6729(3) 0.4564(2) 0.0550(7) Uani 1 d . . C10 C 0.0464(3) 0.7603(3) 0.5268(2) 0.0571(8) Uani 1 d . . C11 C 0.2609(3) 0.9651(3) 0.3793(2) 0.0570(8) Uani 1 d . . C12 C 0.2904(4) 1.1039(4) 0.4211(3) 0.0681(9) Uani 1 d . . H12 H 0.2285(34) 1.1328(32) 0.4676(22) 0.062(8) Uiso 1 d . . C13 C 0.4050(4) 1.1984(4) 0.4029(3) 0.0780(11) Uani 1 d . . H13 H 0.4241(42) 1.2837(45) 0.4312(27) 0.086(12) Uiso 1 d . . C14 C 0.4930(4) 1.1575(4) 0.3441(3) 0.0737(10) Uani 1 d . . H14 H 0.5723(45) 1.2200(42) 0.3337(27) 0.089(12) Uiso 1 d . . C15 C 0.4674(4) 1.0189(4) 0.3034(2) 0.0642(8) Uani 1 d . . H15 H 0.5295(34) 0.9873(32) 0.2639(22) 0.059(8) Uiso 1 d . . C16 C 0.3522(3) 0.9216(3) 0.3199(2) 0.0571(8) Uani 1 d . . C21 C -0.2849(4) 0.9222(3) 0.0590(2) 0.0637(8) Uani 1 d . . C22 C -0.3050(4) 0.9366(4) -0.0422(3) 0.0734(10) Uani 1 d . . C23 C -0.2193(4) 0.8960(4) -0.0977(3) 0.0724(10) Uani 1 d . . C24 C -0.0983(4) 0.8287(3) -0.0628(2) 0.0621(8) Uani 1 d . . C25 C 0.0484(4) 0.7606(3) 0.0770(2) 0.0574(8) Uani 1 d . . C26 C 0.0827(3) 0.7524(3) 0.1733(2) 0.0540(7) Uani 1 d . . C27 C -0.0087(3) 0.7978(3) 0.2327(2) 0.0544(7) Uani 1 d . . C28 C -0.1285(4) 0.8507(3) 0.1939(2) 0.0571(8) Uani 1 d . . C29 C -0.1588(3) 0.8619(3) 0.0985(2) 0.0554(7) Uani 1 d . . C30 C -0.0691(3) 0.8166(3) 0.0392(2) 0.0544(7) Uani 1 d . . C31 C 0.2108(3) 0.6935(3) 0.2109(2) 0.0555(7) Uani 1 d . . C32 C 0.2077(4) 0.5567(4) 0.1739(2) 0.0689(9) Uani 1 d . . H32 H 0.1166(38) 0.4994(37) 0.1277(24) 0.073(10) Uiso 1 d . . C33 C 0.3259(5) 0.4990(4) 0.2063(3) 0.0782(10) Uani 1 d . . H33 H 0.3273(39) 0.4122(43) 0.1831(25) 0.080(11) Uiso 1 d . . C34 C 0.4497(4) 0.5770(4) 0.2743(3) 0.0782(10) Uani 1 d . . H34 H 0.5235(45) 0.5353(42) 0.2995(27) 0.091(12) Uiso 1 d . . C35 C 0.4557(4) 0.7130(4) 0.3103(3) 0.0690(9) Uani 1 d . . H36 H 0.5405(42) 0.7711(39) 0.3601(25) 0.081(11) Uiso 1 d . . C36 C 0.3375(3) 0.7736(3) 0.2805(2) 0.0558(7) Uani 1 d . . C37 C 0.6938(7) 0.3240(7) 0.1408(4) 0.131(2) Uani 1 d . . H37A H 0.7908(7) 0.3804(7) 0.1736(4) 0.197 Uiso 1 calc R . H37B H 0.7056(7) 0.2420(7) 0.1032(4) 0.197 Uiso 1 calc R . H37C H 0.6374(7) 0.2998(7) 0.1870(4) 0.197 Uiso 1 calc R . C38 C 0.6140(6) 0.4000(5) 0.0778(4) 0.1008(14) Uani 1 d . . H2 H -0.2363(44) 0.4889(42) 0.6065(27) 0.095(12) Uiso 1 d . . H3 H -0.0433(40) 0.6395(38) 0.7188(28) 0.081(11) Uiso 1 d . . H5 H 0.2248(38) 0.9207(37) 0.5445(24) 0.068(9) Uiso 1 d . . H8 H -0.1667(33) 0.6306(30) 0.3154(20) 0.052(8) Uiso 1 d . . H22 H -0.3824(47) 0.9912(45) -0.0668(29) 0.102(13) Uiso 1 d . . H23 H -0.2341(40) 0.9036(39) -0.1675(29) 0.088(11) Uiso 1 d . . H25 H 0.1093(35) 0.7354(33) 0.0349(22) 0.063(9) Uiso 1 d . . H28 H -0.1878(35) 0.8789(31) 0.2321(22) 0.058(8) Uiso 1 d . . H5' H 0.6212(93) 0.5824(92) 0.0395(64) 0.234(36) Uiso 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 O1 0.088(2) 0.087(2) 0.082(2) 0.0264(14) 0.0073(13) -0.0110(15) O2 0.096(2) 0.119(2) 0.0536(14) 0.0059(14) 0.0110(12) 0.002(2) O3 0.082(2) 0.114(2) 0.077(2) 0.0150(14) 0.0148(13) 0.050(2) O4 0.099(2) 0.113(2) 0.0552(14) 0.0155(13) 0.0213(13) 0.037(2) O5 0.151(4) 0.108(3) 0.217(5) 0.069(3) -0.034(3) -0.027(3) O6 0.151(4) 0.092(3) 0.168(4) 0.041(2) -0.013(3) -0.015(2) C1 0.065(2) 0.061(2) 0.069(2) 0.016(2) 0.013(2) 0.012(2) C2 0.087(3) 0.077(3) 0.074(2) 0.027(2) 0.032(2) 0.017(2) C3 0.085(3) 0.080(3) 0.059(2) 0.020(2) 0.021(2) 0.017(2) C4 0.074(2) 0.078(2) 0.056(2) 0.010(2) 0.016(2) 0.020(2) C5 0.056(2) 0.065(2) 0.055(2) 0.006(2) 0.0090(14) 0.013(2) C6 0.056(2) 0.052(2) 0.054(2) 0.0059(13) 0.0137(12) 0.0125(13) C7 0.054(2) 0.056(2) 0.051(2) 0.0060(13) 0.0104(13) 0.0168(14) C8 0.055(2) 0.056(2) 0.053(2) 0.0069(14) 0.0075(13) 0.0096(14) C9 0.058(2) 0.053(2) 0.056(2) 0.0097(13) 0.0144(13) 0.0175(14) C10 0.064(2) 0.059(2) 0.052(2) 0.0099(13) 0.0162(13) 0.0186(15) C11 0.055(2) 0.056(2) 0.055(2) 0.0075(13) 0.0077(13) 0.0077(14) C12 0.069(2) 0.060(2) 0.071(2) 0.003(2) 0.017(2) 0.011(2) C13 0.075(2) 0.060(2) 0.089(3) 0.005(2) 0.011(2) 0.008(2) C14 0.066(2) 0.074(3) 0.076(2) 0.019(2) 0.014(2) 0.004(2) C15 0.058(2) 0.072(2) 0.060(2) 0.012(2) 0.0139(15) 0.010(2) C16 0.053(2) 0.061(2) 0.053(2) 0.0076(14) 0.0070(13) 0.0140(14) C21 0.064(2) 0.061(2) 0.063(2) 0.0107(15) 0.0057(15) 0.019(2) C22 0.075(2) 0.073(2) 0.070(2) 0.023(2) 0.004(2) 0.019(2) C23 0.076(2) 0.079(2) 0.057(2) 0.019(2) 0.004(2) 0.012(2) C24 0.069(2) 0.059(2) 0.052(2) 0.0088(14) 0.0073(14) 0.009(2) C25 0.062(2) 0.060(2) 0.050(2) 0.0066(13) 0.0141(13) 0.0165(15) C26 0.054(2) 0.051(2) 0.053(2) 0.0074(13) 0.0076(12) 0.0102(13) C27 0.056(2) 0.054(2) 0.052(2) 0.0101(13) 0.0091(12) 0.0114(13) C28 0.058(2) 0.059(2) 0.053(2) 0.0070(14) 0.0121(13) 0.0165(14) C29 0.057(2) 0.050(2) 0.054(2) 0.0091(13) 0.0043(13) 0.0099(13) C30 0.057(2) 0.049(2) 0.052(2) 0.0058(12) 0.0066(12) 0.0076(13) C31 0.060(2) 0.058(2) 0.052(2) 0.0109(14) 0.0153(13) 0.0180(14) C32 0.068(2) 0.066(2) 0.068(2) 0.006(2) 0.009(2) 0.018(2) C33 0.083(3) 0.061(2) 0.094(3) 0.009(2) 0.020(2) 0.028(2) C34 0.067(3) 0.082(3) 0.092(3) 0.021(2) 0.014(2) 0.036(2) C35 0.060(2) 0.076(2) 0.071(2) 0.012(2) 0.012(2) 0.021(2) C36 0.053(2) 0.060(2) 0.057(2) 0.0113(14) 0.0158(13) 0.0146(14) C37 0.135(5) 0.141(5) 0.136(5) 0.046(4) 0.031(3) 0.061(4) C38 0.103(4) 0.081(3) 0.110(3) 0.013(3) 0.022(3) 0.008(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 C1 1.226(4) . ? O2 C4 1.214(4) . ? O3 C21 1.218(4) . ? O4 C24 1.220(4) . ? O5 C38 1.253(6) . ? O6 C38 1.229(6) . ? C1 C2 1.470(5) . ? C1 C9 1.490(5) . ? C2 C3 1.333(5) . ? C3 C4 1.475(5) . ? C4 C10 1.491(4) . ? C5 C10 1.388(5) . ? C5 C6 1.393(4) . ? C6 C7 1.416(4) . ? C6 C11 1.488(4) . ? C7 C8 1.387(4) . ? C7 C27 1.483(4) . ? C8 C9 1.390(4) . ? C9 C10 1.404(4) . ? C11 C12 1.395(4) . ? C11 C16 1.407(4) . ? C12 C13 1.385(5) . ? C13 C14 1.369(5) . ? C14 C15 1.393(5) . ? C15 C16 1.395(4) . ? C16 C36 1.490(4) . ? C21 C22 1.475(5) . ? C21 C29 1.487(4) . ? C22 C23 1.318(5) . ? C23 C24 1.477(5) . ? C24 C30 1.478(4) . ? C25 C30 1.389(4) . ? C25 C26 1.388(4) . ? C26 C27 1.416(4) . ? C26 C31 1.485(4) . ? C27 C28 1.391(4) . ? C28 C29 1.383(4) . ? C29 C30 1.401(4) . ? C31 C32 1.400(5) . ? C31 C36 1.411(4) . ? C32 C33 1.383(5) . ? C33 C34 1.378(6) . ? C34 C35 1.383(5) . ? C35 C36 1.393(5) . ? C37 C38 1.467(8) . ? 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 C2 120.8(3) . . ? O1 C1 C9 121.4(3) . . ? C2 C1 C9 117.8(3) . . ? C3 C2 C1 121.8(4) . . ? C2 C3 C4 122.8(3) . . ? O2 C4 C3 121.6(3) . . ? O2 C4 C10 121.4(3) . . ? C3 C4 C10 117.0(3) . . ? C10 C5 C6 121.5(3) . . ? C5 C6 C7 118.5(3) . . ? C5 C6 C11 119.6(3) . . ? C7 C6 C11 121.9(3) . . ? C8 C7 C6 119.5(3) . . ? C8 C7 C27 118.8(3) . . ? C6 C7 C27 121.7(3) . . ? C7 C8 C9 121.7(3) . . ? C8 C9 C10 118.8(3) . . ? C8 C9 C1 121.1(3) . . ? C10 C9 C1 120.1(3) . . ? C5 C10 C9 119.8(3) . . ? C5 C10 C4 119.8(3) . . ? C9 C10 C4 120.3(3) . . ? C12 C11 C16 118.9(3) . . ? C12 C11 C6 119.2(3) . . ? C16 C11 C6 121.7(3) . . ? C13 C12 C11 120.9(3) . . ? C14 C13 C12 120.7(4) . . ? C13 C14 C15 119.2(4) . . ? C14 C15 C16 121.3(3) . . ? C15 C16 C11 119.0(3) . . ? C15 C16 C36 118.8(3) . . ? C11 C16 C36 122.0(3) . . ? O3 C21 C22 121.4(3) . . ? O3 C21 C29 121.6(3) . . ? C22 C21 C29 117.0(3) . . ? C23 C22 C21 123.0(4) . . ? C22 C23 C24 121.7(3) . . ? O4 C24 C23 120.8(3) . . ? O4 C24 C30 121.6(3) . . ? C23 C24 C30 117.6(3) . . ? C30 C25 C26 121.6(3) . . ? C25 C26 C27 118.6(3) . . ? C25 C26 C31 119.8(3) . . ? C27 C26 C31 121.6(3) . . ? C28 C27 C26 119.5(3) . . ? C28 C27 C7 119.6(3) . . ? C26 C27 C7 120.8(3) . . ? C29 C28 C27 121.3(3) . . ? C28 C29 C30 119.5(3) . . ? C28 C29 C21 120.5(3) . . ? C30 C29 C21 120.0(3) . . ? C25 C30 C29 119.4(3) . . ? C25 C30 C24 120.0(3) . . ? C29 C30 C24 120.6(3) . . ? C32 C31 C36 119.4(3) . . ? C32 C31 C26 119.1(3) . . ? C36 C31 C26 121.5(3) . . ? C33 C32 C31 120.7(3) . . ? C34 C33 C32 120.0(4) . . ? C33 C34 C35 120.0(4) . . ? C34 C35 C36 121.4(3) . . ? C35 C36 C31 118.5(3) . . ? C35 C36 C16 118.9(3) . . ? C31 C36 C16 122.5(3) . . ? O6 C38 O5 121.0(5) . . ? O6 C38 C37 122.8(5) . . ? O5 C38 C37 116.1(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.5(4) . . . . ? C9 C1 C2 C3 0.1(5) . . . . ? C1 C2 C3 C4 -1.7(6) . . . . ? C2 C3 C4 O2 179.4(4) . . . . ? C2 C3 C4 C10 -0.1(5) . . . . ? C10 C5 C6 C7 3.8(5) . . . . ? C10 C5 C6 C11 -177.6(3) . . . . ? C5 C6 C7 C8 -3.7(4) . . . . ? C11 C6 C7 C8 177.7(3) . . . . ? C5 C6 C7 C27 174.1(3) . . . . ? C11 C6 C7 C27 -4.5(5) . . . . ? C6 C7 C8 C9 0.2(5) . . . . ? C27 C7 C8 C9 -177.6(3) . . . . ? C7 C8 C9 C10 3.3(5) . . . . ? C7 C8 C9 C1 -175.1(3) . . . . ? O1 C1 C9 C8 2.3(5) . . . . ? C2 C1 C9 C8 -178.3(3) . . . . ? O1 C1 C9 C10 -176.0(3) . . . . ? C2 C1 C9 C10 3.4(5) . . . . ? C6 C5 C10 C9 -0.3(5) . . . . ? C6 C5 C10 C4 180.0(3) . . . . ? C8 C9 C10 C5 -3.2(5) . . . . ? C1 C9 C10 C5 175.1(3) . . . . ? C8 C9 C10 C4 176.5(3) . . . . ? C1 C9 C10 C4 -5.2(4) . . . . ? O2 C4 C10 C5 3.8(5) . . . . ? C3 C4 C10 C5 -176.7(3) . . . . ? O2 C4 C10 C9 -175.9(3) . . . . ? C3 C4 C10 C9 3.6(5) . . . . ? C5 C6 C11 C12 -57.4(4) . . . . ? C7 C6 C11 C12 121.2(3) . . . . ? C5 C6 C11 C16 117.6(3) . . . . ? C7 C6 C11 C16 -63.8(4) . . . . ? C16 C11 C12 C13 1.7(5) . . . . ? C6 C11 C12 C13 176.8(3) . . . . ? C11 C12 C13 C14 -0.7(6) . . . . ? C12 C13 C14 C15 -0.8(6) . . . . ? C13 C14 C15 C16 1.2(6) . . . . ? C14 C15 C16 C11 -0.2(5) . . . . ? C14 C15 C16 C36 -175.4(3) . . . . ? C12 C11 C16 C15 -1.2(4) . . . . ? C6 C11 C16 C15 -176.2(3) . . . . ? C12 C11 C16 C36 173.9(3) . . . . ? C6 C11 C16 C36 -1.1(5) . . . . ? O3 C21 C22 C23 -178.5(4) . . . . ? C29 C21 C22 C23 1.6(5) . . . . ? C21 C22 C23 C24 1.8(6) . . . . ? C22 C23 C24 O4 178.0(4) . . . . ? C22 C23 C24 C30 -4.1(5) . . . . ? C30 C25 C26 C27 2.4(5) . . . . ? C30 C25 C26 C31 -179.1(3) . . . . ? C25 C26 C27 C28 -0.8(4) . . . . ? C31 C26 C27 C28 -179.2(3) . . . . ? C25 C26 C27 C7 176.0(3) . . . . ? C31 C26 C27 C7 -2.5(4) . . . . ? C8 C7 C27 C28 66.8(4) . . . . ? C6 C7 C27 C28 -111.0(3) . . . . ? C8 C7 C27 C26 -110.0(3) . . . . ? C6 C7 C27 C26 72.2(4) . . . . ? C26 C27 C28 C29 -1.0(5) . . . . ? C7 C27 C28 C29 -177.8(3) . . . . ? C27 C28 C29 C30 1.3(5) . . . . ? C27 C28 C29 C21 -178.4(3) . . . . ? O3 C21 C29 C28 -2.8(5) . . . . ? C22 C21 C29 C28 177.1(3) . . . . ? O3 C21 C29 C30 177.5(3) . . . . ? C22 C21 C29 C30 -2.6(4) . . . . ? C26 C25 C30 C29 -2.2(5) . . . . ? C26 C25 C30 C24 177.5(3) . . . . ? C28 C29 C30 C25 0.3(4) . . . . ? C21 C29 C30 C25 180.0(3) . . . . ? C28 C29 C30 C24 -179.4(3) . . . . ? C21 C29 C30 C24 0.2(4) . . . . ? O4 C24 C30 C25 1.1(5) . . . . ? C23 C24 C30 C25 -176.7(3) . . . . ? O4 C24 C30 C29 -179.2(3) . . . . ? C23 C24 C30 C29 3.0(4) . . . . ? C25 C26 C31 C32 -61.6(4) . . . . ? C27 C26 C31 C32 116.8(3) . . . . ? C25 C26 C31 C36 116.1(3) . . . . ? C27 C26 C31 C36 -65.5(4) . . . . ? C36 C31 C32 C33 1.4(5) . . . . ? C26 C31 C32 C33 179.1(3) . . . . ? C31 C32 C33 C34 -1.3(6) . . . . ? C32 C33 C34 C35 0.1(6) . . . . ? C33 C34 C35 C36 1.0(6) . . . . ? C34 C35 C36 C31 -1.0(5) . . . . ? C34 C35 C36 C16 -178.4(3) . . . . ? C32 C31 C36 C35 -0.2(4) . . . . ? C26 C31 C36 C35 -177.9(3) . . . . ? C32 C31 C36 C16 177.1(3) . . . . ? C26 C31 C36 C16 -0.6(4) . . . . ? C15 C16 C36 C35 60.9(4) . . . . ? C11 C16 C36 C35 -114.3(3) . . . . ? C15 C16 C36 C31 -116.4(3) . . . . ? C11 C16 C36 C31 68.4(4) . . . . ? _refine_diff_density_max 0.189 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.048 data_y14 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C38 H28 O4' _chemical_formula_weight 548.60 _chemical_melting_point ? _chemical_compound_source ? 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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z-1/2' _cell_length_a 10.498(3) _cell_length_b 9.646(2) _cell_length_c 14.687(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.080(10) _cell_angle_gamma 90.00 _cell_volume 1459.6(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.248 _exptl_crystal_density_method ? _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4024 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_sigmaI/netI 0.0634 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 25.54 _reflns_number_total 2415 _reflns_number_observed 2113 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 17 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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 w=1/[\s^2^(Fo^2^)+(0.1388P)^2^+0.2386P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0304(145) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2398 _refine_ls_number_parameters 210 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_obs 0.0806 _refine_ls_wR_factor_all 0.2696 _refine_ls_wR_factor_obs 0.2358 _refine_ls_goodness_of_fit_all 1.112 _refine_ls_goodness_of_fit_obs 1.139 _refine_ls_restrained_S_all 1.232 _refine_ls_restrained_S_obs 1.139 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.6440(3) -0.3734(2) 0.4654(2) 0.1060(8) Uani 1 d . . O2 O 0.2851(2) 0.0245(3) 0.3960(2) 0.1160(9) Uani 1 d . . C1 C 0.5648(3) -0.2803(3) 0.4500(2) 0.0823(8) Uani 1 d . . C2 C 0.4532(4) -0.2712(4) 0.4980(2) 0.0935(10) Uani 1 d . . C3 C 0.3645(3) -0.1722(4) 0.4816(2) 0.0918(10) Uani 1 d . . C4 C 0.3686(3) -0.0639(3) 0.4109(2) 0.0830(9) Uani 1 d . . C5 C 0.4897(2) 0.0343(3) 0.2958(2) 0.0691(7) Uani 1 d . . C6 C 0.5966(2) 0.0403(3) 0.2522(2) 0.0627(7) Uani 1 d . . C7 C 0.6922(2) -0.0624(3) 0.2734(2) 0.0621(7) Uani 1 d . . C8 C 0.6799(2) -0.1669(3) 0.3357(2) 0.0670(7) Uani 1 d . . C9 C 0.5744(3) -0.1688(3) 0.3810(2) 0.0682(7) Uani 1 d . . C10 C 0.4791(2) -0.0669(3) 0.3605(2) 0.0690(7) Uani 1 d . . C11 C 0.6068(2) 0.1531(3) 0.1847(2) 0.0654(7) Uani 1 d . . C12 C 0.5172(3) 0.1618(3) 0.1019(2) 0.0819(9) Uani 1 d . . H12 H 0.4744(3) 0.0897(3) 0.0845(2) 0.086 Uiso 1 d R . C13 C 0.5228(3) 0.2690(4) 0.0397(2) 0.0964(10) Uani 1 d . . H13 H 0.4747(3) 0.3150(4) -0.0222(2) 0.128 Uiso 1 d R . C14 C 0.6175(3) 0.3703(3) 0.0602(2) 0.0921(10) Uani 1 d . . H14 H 0.5988(3) 0.4458(3) 0.0164(2) 0.087 Uiso 1 d R . C15 C 0.7056(3) 0.3655(3) 0.1426(2) 0.0764(8) Uani 1 d . . H15 H 0.7952(3) 0.4606(3) 0.1539(2) 0.114 Uiso 1 d R . C16 C 0.7023(2) 0.2562(3) 0.2052(2) 0.0648(7) Uani 1 d . . H2 H 0.4589 -0.3383 0.5434 0.067 Uiso 1 d . . H3 H 0.2330 -0.1524 0.5009 0.120 Uiso 1 d . . H5 H 0.4309 0.0888 0.2775 0.065 Uiso 1 d . . H8 H 0.7560 -0.2356 0.3468 0.092 Uiso 1 d . . C17 C 0.7500 0.6430(9) -0.2500 0.204(5) Uani 1 d SD . C18 C 0.6544(27) 0.5572(24) -0.2094(16) 0.210(12) Uani 0.50 d PD . C19 C 0.6224(12) 0.4230(20) -0.2579(20) 0.300(21) Uani 0.50 d PD . C20 C 0.7500 0.3484(10) -0.2500 0.206(6) Uani 1 d SD . C21 C 0.8546(19) 0.4404(23) -0.2879(17) 0.212(10) Uani 0.50 d PD . C22 C 0.8788(13) 0.5685(18) -0.2312(15) 0.193(9) Uani 0.50 d PD . 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 0.118(2) 0.0871(15) 0.126(2) 0.0313(13) 0.0547(15) 0.0246(14) O2 0.0893(15) 0.123(2) 0.156(2) 0.035(2) 0.074(2) 0.0280(14) C1 0.093(2) 0.070(2) 0.092(2) 0.0064(14) 0.039(2) 0.003(2) C2 0.110(2) 0.085(2) 0.099(2) 0.016(2) 0.054(2) -0.006(2) C3 0.090(2) 0.091(2) 0.107(2) 0.005(2) 0.052(2) -0.006(2) C4 0.071(2) 0.084(2) 0.105(2) 0.005(2) 0.044(2) 0.0035(15) C5 0.0533(13) 0.071(2) 0.088(2) 0.0080(13) 0.0252(12) 0.0064(11) C6 0.0530(13) 0.0649(13) 0.0740(14) -0.0006(11) 0.0220(10) -0.0025(10) C7 0.0530(13) 0.0635(13) 0.0742(14) -0.0027(11) 0.0233(10) -0.0031(10) C8 0.0602(14) 0.0658(14) 0.080(2) 0.0020(12) 0.0260(12) 0.0021(11) C9 0.0687(15) 0.0652(14) 0.077(2) 0.0024(12) 0.0294(12) -0.0024(12) C10 0.0614(14) 0.070(2) 0.082(2) 0.0005(13) 0.0306(12) -0.0037(12) C11 0.0540(13) 0.0694(15) 0.0776(15) 0.0041(12) 0.0246(11) 0.0043(11) C12 0.064(2) 0.094(2) 0.090(2) 0.010(2) 0.0201(14) -0.0001(14) C13 0.081(2) 0.116(3) 0.093(2) 0.032(2) 0.018(2) 0.017(2) C14 0.089(2) 0.090(2) 0.104(2) 0.034(2) 0.034(2) 0.018(2) C15 0.073(2) 0.067(2) 0.097(2) 0.0128(14) 0.0357(15) 0.0087(13) C16 0.0603(13) 0.0629(14) 0.0783(14) 0.0047(11) 0.0312(11) 0.0055(10) C17 0.131(7) 0.119(6) 0.367(16) 0.000 0.059(8) 0.000 C18 0.220(19) 0.191(18) 0.260(23) -0.115(17) 0.147(19) -0.087(15) C19 0.237(22) 0.159(17) 0.419(39) -0.072(20) -0.148(24) -0.005(15) C20 0.231(13) 0.115(6) 0.231(12) 0.000 -0.059(10) 0.000 C21 0.229(22) 0.193(18) 0.212(17) -0.039(15) 0.038(14) 0.124(18) C22 0.152(12) 0.173(16) 0.278(26) 0.050(16) 0.099(15) 0.005(11) _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 1.215(4) . ? O2 C4 1.213(4) . ? C1 C2 1.482(4) . ? C1 C9 1.495(4) . ? C2 C3 1.324(5) . ? C3 C4 1.478(5) . ? C4 C10 1.492(3) . ? C5 C10 1.382(4) . ? C5 C6 1.396(3) . ? C6 C7 1.402(3) . ? C6 C11 1.489(3) . ? C7 C8 1.384(3) . ? C7 C7 1.504(4) 2_655 ? C8 C9 1.398(3) . ? C9 C10 1.393(4) . ? C11 C12 1.390(4) . ? C11 C16 1.402(3) . ? C12 C13 1.390(4) . ? C13 C14 1.385(5) . ? C14 C15 1.375(5) . ? C15 C16 1.404(3) . ? C16 C16 1.494(5) 2_655 ? C17 C22 1.509(9) 2_654 ? C17 C22 1.509(9) . ? C17 C18 1.509(9) . ? C17 C18 1.509(9) 2_654 ? C18 C22 0.88(3) 2_654 ? C18 C21 1.13(3) 2_654 ? C18 C19 1.485(10) . ? C19 C21 0.69(3) 2_654 ? C19 C22 1.41(3) 2_654 ? C19 C20 1.505(10) . ? C20 C19 1.505(10) 2_654 ? C20 C21 1.59(3) . ? C20 C21 1.59(3) 2_654 ? C21 C19 0.69(3) 2_654 ? C21 C18 1.13(3) 2_654 ? C21 C22 1.484(10) . ? C22 C18 0.88(3) 2_654 ? C22 C19 1.41(3) 2_654 ? 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 C2 122.0(3) . . ? O1 C1 C9 121.7(3) . . ? C2 C1 C9 116.3(3) . . ? C3 C2 C1 123.3(3) . . ? C2 C3 C4 121.6(3) . . ? O2 C4 C3 120.4(2) . . ? O2 C4 C10 121.9(3) . . ? C3 C4 C10 117.7(3) . . ? C10 C5 C6 121.5(2) . . ? C5 C6 C7 118.3(2) . . ? C5 C6 C11 120.1(2) . . ? C7 C6 C11 121.6(2) . . ? C8 C7 C6 120.5(2) . . ? C8 C7 C7 119.2(2) . 2_655 ? C6 C7 C7 120.3(2) . 2_655 ? C7 C8 C9 120.5(2) . . ? C10 C9 C8 119.3(2) . . ? C10 C9 C1 121.0(2) . . ? C8 C9 C1 119.7(2) . . ? C5 C10 C9 119.9(2) . . ? C5 C10 C4 120.1(2) . . ? C9 C10 C4 120.0(2) . . ? C12 C11 C16 118.7(2) . . ? C12 C11 C6 120.2(2) . . ? C16 C11 C6 121.0(2) . . ? C13 C12 C11 120.9(3) . . ? C14 C13 C12 120.1(3) . . ? C15 C14 C13 120.0(3) . . ? C14 C15 C16 120.3(3) . . ? C11 C16 C15 119.9(2) . . ? C11 C16 C16 121.3(2) . 2_655 ? C15 C16 C16 118.7(2) . 2_655 ? C22 C17 C22 123.1(15) 2_654 . ? C22 C17 C18 34.0(12) 2_654 . ? C22 C17 C18 107.9(10) . . ? C22 C17 C18 107.9(10) 2_654 2_654 ? C22 C17 C18 34.0(12) . 2_654 ? C18 C17 C18 113.5(20) . 2_654 ? C22 C18 C21 94.2(19) 2_654 2_654 ? C22 C18 C19 67.8(20) 2_654 . ? C21 C18 C19 26.5(16) 2_654 . ? C22 C18 C17 73.0(11) 2_654 . ? C21 C18 C17 126.2(21) 2_654 . ? C19 C18 C17 113.3(16) . . ? C21 C19 C22 82.1(23) 2_654 2_654 ? C21 C19 C18 46.8(26) 2_654 . ? C22 C19 C18 35.3(12) 2_654 . ? C21 C19 C20 84.3(25) 2_654 . ? C22 C19 C20 118.1(15) 2_654 . ? C18 C19 C20 105.2(17) . . ? C19 C20 C19 122.9(17) 2_654 . ? C19 C20 C21 25.6(11) 2_654 . ? C19 C20 C21 111.7(12) . . ? C19 C20 C21 111.7(12) 2_654 2_654 ? C19 C20 C21 25.6(11) . 2_654 ? C21 C20 C21 112.3(12) . 2_654 ? C19 C21 C18 106.7(35) 2_654 2_654 ? C19 C21 C22 70.5(27) 2_654 . ? C18 C21 C22 36.3(15) 2_654 . ? C19 C21 C20 70.1(24) 2_654 . ? C18 C21 C20 120.6(16) 2_654 . ? C22 C21 C20 108.8(16) . . ? C18 C22 C19 76.8(23) 2_654 2_654 ? C18 C22 C21 49.4(20) 2_654 . ? C19 C22 C21 27.5(13) 2_654 . ? C18 C22 C17 73.0(11) 2_654 . ? C19 C22 C17 117.7(12) 2_654 . ? C21 C22 C17 104.1(11) . . ? 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 -178.9(4) . . . . ? C9 C1 C2 C3 0.8(5) . . . . ? C1 C2 C3 C4 1.7(6) . . . . ? C2 C3 C4 O2 178.8(3) . . . . ? C2 C3 C4 C10 -2.0(5) . . . . ? C10 C5 C6 C7 2.0(4) . . . . ? C10 C5 C6 C11 -178.3(2) . . . . ? C5 C6 C7 C8 0.3(4) . . . . ? C11 C6 C7 C8 -179.4(2) . . . . ? C5 C6 C7 C7 178.6(2) . . . 2_655 ? C11 C6 C7 C7 -1.1(4) . . . 2_655 ? C6 C7 C8 C9 -2.4(4) . . . . ? C7 C7 C8 C9 179.2(3) 2_655 . . . ? C7 C8 C9 C10 2.3(4) . . . . ? C7 C8 C9 C1 -178.3(3) . . . . ? O1 C1 C9 C10 176.5(3) . . . . ? C2 C1 C9 C10 -3.2(4) . . . . ? O1 C1 C9 C8 -2.9(5) . . . . ? C2 C1 C9 C8 177.4(3) . . . . ? C6 C5 C10 C9 -2.2(4) . . . . ? C6 C5 C10 C4 175.4(3) . . . . ? C8 C9 C10 C5 0.0(4) . . . . ? C1 C9 C10 C5 -179.4(3) . . . . ? C8 C9 C10 C4 -177.5(2) . . . . ? C1 C9 C10 C4 3.0(4) . . . . ? O2 C4 C10 C5 1.2(5) . . . . ? C3 C4 C10 C5 -178.0(3) . . . . ? O2 C4 C10 C9 178.7(3) . . . . ? C3 C4 C10 C9 -0.5(4) . . . . ? C5 C6 C11 C12 -64.9(3) . . . . ? C7 C6 C11 C12 114.8(3) . . . . ? C5 C6 C11 C16 111.9(3) . . . . ? C7 C6 C11 C16 -68.4(3) . . . . ? C16 C11 C12 C13 1.0(4) . . . . ? C6 C11 C12 C13 177.9(3) . . . . ? C11 C12 C13 C14 -0.9(5) . . . . ? C12 C13 C14 C15 -0.5(5) . . . . ? C13 C14 C15 C16 1.7(4) . . . . ? C12 C11 C16 C15 0.2(3) . . . . ? C6 C11 C16 C15 -176.7(2) . . . . ? C12 C11 C16 C16 177.3(2) . . . 2_655 ? C6 C11 C16 C16 0.4(3) . . . 2_655 ? C14 C15 C16 C11 -1.5(4) . . . . ? C14 C15 C16 C16 -178.7(3) . . . 2_655 ? C22 C17 C18 C22 0.000(4) 2_654 . . 2_654 ? C22 C17 C18 C22 -123.3(29) . . . 2_654 ? C18 C17 C18 C22 -87.3(22) 2_654 . . 2_654 ? C22 C17 C18 C21 82.6(24) 2_654 . . 2_654 ? C22 C17 C18 C21 -40.6(39) . . . 2_654 ? C18 C17 C18 C21 -4.7(30) 2_654 . . 2_654 ? C22 C17 C18 C19 55.9(16) 2_654 . . . ? C22 C17 C18 C19 -67.4(26) . . . . ? C18 C17 C18 C19 -31.5(17) 2_654 . . . ? C22 C18 C19 C21 -175.9(42) 2_654 . . 2_654 ? C21 C18 C19 C21 0.000(3) 2_654 . . 2_654 ? C17 C18 C19 C21 125.3(42) . . . 2_654 ? C22 C18 C19 C22 0.000(2) 2_654 . . 2_654 ? C21 C18 C19 C22 175.9(42) 2_654 . . 2_654 ? C17 C18 C19 C22 -58.7(12) . . . 2_654 ? C22 C18 C19 C20 117.4(31) 2_654 . . . ? C21 C18 C19 C20 -66.6(28) 2_654 . . . ? C17 C18 C19 C20 58.7(32) . . . . ? C21 C19 C20 C19 -70.6(25) 2_654 . . 2_654 ? C22 C19 C20 C19 7.3(19) 2_654 . . 2_654 ? C18 C19 C20 C19 -28.3(15) . . . 2_654 ? C21 C19 C20 C21 -96.6(33) 2_654 . . . ? C22 C19 C20 C21 -18.7(28) 2_654 . . . ? C18 C19 C20 C21 -54.3(23) . . . . ? C21 C19 C20 C21 0.000(4) 2_654 . . 2_654 ? C22 C19 C20 C21 77.8(20) 2_654 . . 2_654 ? C18 C19 C20 C21 42.2(19) . . . 2_654 ? C19 C20 C21 C19 0.000(5) 2_654 . . 2_654 ? C19 C20 C21 C19 121.6(26) . . . 2_654 ? C21 C20 C21 C19 94.0(30) 2_654 . . 2_654 ? C19 C20 C21 C18 -98.2(41) 2_654 . . 2_654 ? C19 C20 C21 C18 23.4(32) . . . 2_654 ? C21 C20 C21 C18 -4.2(26) 2_654 . . 2_654 ? C19 C20 C21 C22 -60.1(28) 2_654 . . . ? C19 C20 C21 C22 61.5(16) . . . . ? C21 C20 C21 C22 33.9(10) 2_654 . . . ? C19 C21 C22 C18 -176.2(39) 2_654 . . 2_654 ? C18 C21 C22 C18 0.0 2_654 . . 2_654 ? C20 C21 C22 C18 -116.3(33) . . . 2_654 ? C19 C21 C22 C19 0.0 2_654 . . 2_654 ? C18 C21 C22 C19 176.2(39) 2_654 . . 2_654 ? C20 C21 C22 C19 59.8(22) . . . 2_654 ? C19 C21 C22 C17 -123.8(25) 2_654 . . . ? C18 C21 C22 C17 52.3(22) 2_654 . . . ? C20 C21 C22 C17 -64.0(21) . . . . ? C22 C17 C22 C18 71.8(26) 2_654 . . 2_654 ? C18 C17 C22 C18 105.7(27) . . . 2_654 ? C18 C17 C22 C18 0.000(6) 2_654 . . 2_654 ? C22 C17 C22 C19 7.2(20) 2_654 . . 2_654 ? C18 C17 C22 C19 41.1(25) . . . 2_654 ? C18 C17 C22 C19 -64.6(28) 2_654 . . 2_654 ? C22 C17 C22 C21 32.9(15) 2_654 . . . ? C18 C17 C22 C21 66.8(18) . . . . ? C18 C17 C22 C21 -38.9(24) 2_654 . . . ? _refine_diff_density_max 0.241 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.046