# Electronic Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email fjnan@mail.shcnc.ac.cn _publ_contact_author_name 'Nan, F.J.' _publ_author_name F.J.Nan data_mo_dm1083_0m _database_code_depnum_ccdc_archive 'CCDC 822516' #TrackingRef '- Compound 2 .cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 O7' _chemical_formula_weight 380.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.526(6) _cell_length_b 11.830(10) _cell_length_c 12.312(11) _cell_angle_alpha 90.00 _cell_angle_beta 104.267(13) _cell_angle_gamma 90.00 _cell_volume 921.2(14) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2045 _cell_measurement_theta_min 4.849 _cell_measurement_theta_max 55.134 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.157 _exptl_crystal_size_mid 0.127 _exptl_crystal_size_min 0.023 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.372 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5915 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 4385 _diffrn_reflns_av_R_equivalents 0.0464 _diffrn_reflns_av_sigmaI/netI 0.0905 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 25.50 _reflns_number_total 2821 _reflns_number_gt 1825 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0681P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.005(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 2(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 2821 _refine_ls_number_parameters 251 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1322 _refine_ls_R_factor_gt 0.0860 _refine_ls_wR_factor_ref 0.1641 _refine_ls_wR_factor_gt 0.1490 _refine_ls_goodness_of_fit_ref 1.164 _refine_ls_restrained_S_all 1.164 _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 0.4792(7) 0.6045(3) 0.2879(4) 0.0759(12) Uani 1 1 d . . . H1 H 0.4453 0.6191 0.3462 0.114 Uiso 1 1 calc R . . O2 O 0.9709(5) 0.3790(3) 0.2846(3) 0.0574(10) Uani 1 1 d . . . O3 O 0.7136(6) 0.1479(3) 0.3814(3) 0.0625(11) Uani 1 1 d . . . O4 O 0.7917(6) 0.1587(3) 0.5663(4) 0.0662(11) Uani 1 1 d . . . O5 O 1.1166(6) 0.2198(3) 0.3652(3) 0.0690(11) Uani 1 1 d . . . H5 H 1.1894 0.2291 0.4291 0.104 Uiso 1 1 calc R . . O6 O 1.2280(6) 0.2978(4) 0.5700(4) 0.0693(12) Uani 1 1 d . . . H6 H 1.2437 0.2681 0.6318 0.104 Uiso 1 1 calc R . . O7 O 1.1547(9) 0.2549(4) 0.7629(4) 0.1055(18) Uani 1 1 d . . . C1 C 0.4209(9) 0.4897(5) 0.2552(5) 0.0605(16) Uani 1 1 d . . . H1A H 0.3078 0.4658 0.2898 0.073 Uiso 1 1 calc R . . C2 C 0.3407(11) 0.4884(6) 0.1330(6) 0.079(2) Uani 1 1 d . . . H2A H 0.4469 0.5198 0.0987 0.095 Uiso 1 1 calc R . . H2B H 0.2157 0.5357 0.1121 0.095 Uiso 1 1 calc R . . C3 C 0.2858(10) 0.3703(6) 0.0888(5) 0.081(2) Uani 1 1 d . . . H3A H 0.2365 0.3741 0.0078 0.097 Uiso 1 1 calc R . . H3B H 0.1697 0.3427 0.1177 0.097 Uiso 1 1 calc R . . C4 C 0.4657(9) 0.2856(6) 0.1183(5) 0.0688(17) Uani 1 1 d . . . C5 C 0.5597(8) 0.2929(4) 0.2443(5) 0.0518(14) Uani 1 1 d . . . H5A H 0.4488 0.2640 0.2779 0.062 Uiso 1 1 calc R . . C6 C 0.7484(9) 0.2172(4) 0.2896(4) 0.0535(14) Uani 1 1 d . . . H6A H 0.7815 0.1707 0.2303 0.064 Uiso 1 1 calc R . . C7 C 0.9355(8) 0.2854(4) 0.3492(4) 0.0486(14) Uani 1 1 d . . . C8 C 0.8707(8) 0.3154(4) 0.4549(4) 0.0432(13) Uani 1 1 d . . . C9 C 0.6667(7) 0.3916(4) 0.4221(4) 0.0459(13) Uani 1 1 d . . . H9 H 0.5512 0.3452 0.4358 0.055 Uiso 1 1 calc R . . C10 C 0.6136(7) 0.4121(4) 0.2967(4) 0.0418(12) Uani 1 1 d . . . C11 C 0.6849(9) 0.4914(4) 0.5004(5) 0.0567(15) Uani 1 1 d . . . H11A H 0.7888 0.5443 0.4860 0.068 Uiso 1 1 calc R . . H11B H 0.5500 0.5301 0.4872 0.068 Uiso 1 1 calc R . . C12 C 0.7497(9) 0.4523(5) 0.6189(5) 0.0610(16) Uani 1 1 d . . . H12A H 0.6507 0.3952 0.6306 0.073 Uiso 1 1 calc R . . H12B H 0.7415 0.5155 0.6678 0.073 Uiso 1 1 calc R . . C13 C 0.9730(9) 0.4034(5) 0.6515(5) 0.0590(16) Uani 1 1 d . . . H13 H 1.0646 0.4672 0.6826 0.071 Uiso 1 1 calc R . . C14 C 1.0433(8) 0.3676(4) 0.5475(5) 0.0529(14) Uani 1 1 d . . . H14 H 1.0839 0.4377 0.5158 0.063 Uiso 1 1 calc R . . C15 C 1.0046(11) 0.3182(6) 0.7452(6) 0.0659(17) Uani 1 1 d . . . C16 C 0.7938(8) 0.1997(4) 0.4778(5) 0.0482(13) Uani 1 1 d . . . C17 C 0.8625(11) 0.3202(7) 0.8216(6) 0.095(2) Uani 1 1 d . . . H17A H 0.9216 0.2747 0.8863 0.143 Uiso 1 1 calc R . . H17B H 0.7268 0.2906 0.7836 0.143 Uiso 1 1 calc R . . H17C H 0.8466 0.3965 0.8445 0.143 Uiso 1 1 calc R . . C18 C 0.3743(12) 0.1656(6) 0.0919(6) 0.093(2) Uani 1 1 d . . . H18A H 0.3082 0.1596 0.0133 0.140 Uiso 1 1 calc R . . H18B H 0.2715 0.1513 0.1342 0.140 Uiso 1 1 calc R . . H18C H 0.4863 0.1111 0.1118 0.140 Uiso 1 1 calc R . . C19 C 0.6224(11) 0.3046(7) 0.0462(5) 0.083(2) Uani 1 1 d . . . H19A H 0.6705 0.3815 0.0538 0.125 Uiso 1 1 calc R . . H19B H 0.5542 0.2895 -0.0308 0.125 Uiso 1 1 calc R . . H19C H 0.7409 0.2547 0.0704 0.125 Uiso 1 1 calc R . . C20 C 0.8083(8) 0.4612(4) 0.2687(5) 0.0565(15) Uani 1 1 d . . . H20A H 0.7734 0.4866 0.1914 0.068 Uiso 1 1 calc R . . H20B H 0.8572 0.5260 0.3163 0.068 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 0.084(3) 0.051(2) 0.101(4) 0.006(2) 0.038(3) 0.012(2) O2 0.051(2) 0.056(2) 0.080(3) 0.013(2) 0.042(2) 0.0035(19) O3 0.084(3) 0.0402(18) 0.069(3) 0.001(2) 0.029(2) -0.0137(19) O4 0.078(3) 0.059(2) 0.069(3) 0.009(2) 0.032(2) -0.015(2) O5 0.062(2) 0.065(2) 0.090(3) 0.012(3) 0.038(2) 0.026(2) O6 0.046(2) 0.077(3) 0.087(3) 0.003(2) 0.019(2) 0.006(2) O7 0.121(4) 0.105(4) 0.093(4) 0.019(3) 0.032(3) 0.035(4) C1 0.053(3) 0.062(4) 0.067(5) 0.000(3) 0.018(3) -0.003(3) C2 0.070(4) 0.088(5) 0.078(5) 0.016(4) 0.016(4) 0.009(4) C3 0.065(4) 0.113(6) 0.062(4) -0.001(4) 0.011(3) -0.007(4) C4 0.065(4) 0.089(4) 0.058(4) -0.015(3) 0.027(3) -0.015(4) C5 0.055(3) 0.052(3) 0.054(3) -0.005(3) 0.025(3) -0.017(3) C6 0.069(4) 0.048(3) 0.053(3) -0.006(3) 0.033(3) 0.000(3) C7 0.054(3) 0.048(3) 0.055(4) 0.004(3) 0.036(3) 0.001(3) C8 0.044(3) 0.038(3) 0.055(3) 0.003(2) 0.027(3) -0.007(2) C9 0.043(3) 0.039(3) 0.062(4) -0.004(3) 0.026(3) -0.003(2) C10 0.038(3) 0.041(3) 0.054(3) -0.003(2) 0.026(2) -0.002(2) C11 0.066(3) 0.049(3) 0.062(4) -0.010(3) 0.028(3) 0.006(3) C12 0.071(4) 0.060(3) 0.057(4) -0.011(3) 0.026(3) 0.004(3) C13 0.061(4) 0.054(3) 0.066(4) -0.006(3) 0.022(3) -0.016(3) C14 0.050(3) 0.045(3) 0.067(4) 0.001(3) 0.020(3) -0.005(3) C15 0.070(4) 0.065(4) 0.063(4) -0.008(3) 0.016(4) -0.012(4) C16 0.045(3) 0.047(3) 0.057(4) 0.000(3) 0.022(3) -0.007(2) C17 0.095(5) 0.120(6) 0.073(5) 0.007(4) 0.024(4) -0.026(5) C18 0.104(5) 0.101(5) 0.071(5) -0.030(4) 0.015(4) -0.029(5) C19 0.093(5) 0.098(5) 0.067(4) -0.001(4) 0.035(4) 0.003(4) C20 0.052(3) 0.046(3) 0.079(4) 0.013(3) 0.030(3) -0.003(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 1.441(6) . ? O1 H1 0.8200 . ? O2 C7 1.416(6) . ? O2 C20 1.417(6) . ? O3 C16 1.324(6) . ? O3 C6 1.459(6) . ? O4 C16 1.196(6) . ? O5 C7 1.386(6) . ? O5 H5 0.8200 . ? O6 C14 1.431(6) . ? O6 H6 0.8200 . ? O7 C15 1.209(7) . ? C1 C2 1.467(9) . ? C1 C10 1.538(7) . ? C1 H1A 0.9800 . ? C2 C3 1.509(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.518(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.524(8) . ? C4 C19 1.526(9) . ? C4 C18 1.543(9) . ? C5 C6 1.514(8) . ? C5 C10 1.555(7) . ? C5 H5A 0.9800 . ? C6 C7 1.496(7) . ? C6 H6A 0.9800 . ? C7 C8 1.506(7) . ? C8 C16 1.508(7) . ? C8 C14 1.522(7) . ? C8 C9 1.576(7) . ? C9 C11 1.510(7) . ? C9 C10 1.517(7) . ? C9 H9 0.9800 . ? C10 C20 1.512(7) . ? C11 C12 1.489(8) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.527(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C15 1.508(9) . ? C13 C14 1.522(8) . ? C13 H13 0.9800 . ? C14 H14 0.9800 . ? C15 C17 1.474(9) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? C7 O2 C20 113.2(4) . . ? C16 O3 C6 109.3(4) . . ? C7 O5 H5 109.5 . . ? C14 O6 H6 109.5 . . ? O1 C1 C2 107.4(5) . . ? O1 C1 C10 109.4(4) . . ? C2 C1 C10 112.9(5) . . ? O1 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? C10 C1 H1A 109.0 . . ? C1 C2 C3 111.9(6) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C2 C3 C4 115.1(5) . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3A 108.5 . . ? C2 C3 H3B 108.5 . . ? C4 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C5 107.4(5) . . ? C3 C4 C19 110.7(6) . . ? C5 C4 C19 115.1(5) . . ? C3 C4 C18 108.8(5) . . ? C5 C4 C18 107.7(5) . . ? C19 C4 C18 107.0(6) . . ? C6 C5 C4 115.4(4) . . ? C6 C5 C10 107.6(4) . . ? C4 C5 C10 117.9(5) . . ? C6 C5 H5A 104.9 . . ? C4 C5 H5A 104.9 . . ? C10 C5 H5A 104.9 . . ? O3 C6 C7 100.8(4) . . ? O3 C6 C5 110.5(4) . . ? C7 C6 C5 110.7(4) . . ? O3 C6 H6A 111.5 . . ? C7 C6 H6A 111.5 . . ? C5 C6 H6A 111.5 . . ? O5 C7 O2 105.4(4) . . ? O5 C7 C6 109.4(5) . . ? O2 C7 C6 111.9(4) . . ? O5 C7 C8 114.9(4) . . ? O2 C7 C8 114.8(4) . . ? C6 C7 C8 100.5(4) . . ? C7 C8 C16 97.1(4) . . ? C7 C8 C14 115.4(4) . . ? C16 C8 C14 116.6(4) . . ? C7 C8 C9 108.2(4) . . ? C16 C8 C9 105.5(4) . . ? C14 C8 C9 112.5(4) . . ? C11 C9 C10 119.1(4) . . ? C11 C9 C8 110.8(4) . . ? C10 C9 C8 108.6(4) . . ? C11 C9 H9 105.8 . . ? C10 C9 H9 105.8 . . ? C8 C9 H9 105.8 . . ? C20 C10 C9 107.4(4) . . ? C20 C10 C1 111.1(4) . . ? C9 C10 C1 113.3(4) . . ? C20 C10 C5 111.8(4) . . ? C9 C10 C5 104.4(4) . . ? C1 C10 C5 108.7(4) . . ? C12 C11 C9 109.9(4) . . ? C12 C11 H11A 109.7 . . ? C9 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C9 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C11 C12 C13 113.4(5) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C15 C13 C14 116.4(5) . . ? C15 C13 C12 113.3(5) . . ? C14 C13 C12 110.5(4) . . ? C15 C13 H13 105.1 . . ? C14 C13 H13 105.1 . . ? C12 C13 H13 105.1 . . ? O6 C14 C13 114.3(4) . . ? O6 C14 C8 110.1(4) . . ? C13 C14 C8 115.0(4) . . ? O6 C14 H14 105.5 . . ? C13 C14 H14 105.5 . . ? C8 C14 H14 105.5 . . ? O7 C15 C17 120.3(7) . . ? O7 C15 C13 120.2(7) . . ? C17 C15 C13 119.2(6) . . ? O4 C16 O3 122.6(5) . . ? O4 C16 C8 128.1(5) . . ? O3 C16 C8 109.2(5) . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 C10 110.3(4) . . ? O2 C20 H20A 109.6 . . ? C10 C20 H20A 109.6 . . ? O2 C20 H20B 109.6 . . ? C10 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? 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 176.9(5) . . . . ? C10 C1 C2 C3 56.2(7) . . . . ? C1 C2 C3 C4 -57.1(8) . . . . ? C2 C3 C4 C5 50.7(7) . . . . ? C2 C3 C4 C19 -75.7(7) . . . . ? C2 C3 C4 C18 167.0(6) . . . . ? C3 C4 C5 C6 -177.7(5) . . . . ? C19 C4 C5 C6 -54.0(7) . . . . ? C18 C4 C5 C6 65.3(6) . . . . ? C3 C4 C5 C10 -48.6(6) . . . . ? C19 C4 C5 C10 75.1(7) . . . . ? C18 C4 C5 C10 -165.6(5) . . . . ? C16 O3 C6 C7 24.1(5) . . . . ? C16 O3 C6 C5 -93.0(5) . . . . ? C4 C5 C6 O3 -126.7(5) . . . . ? C10 C5 C6 O3 99.4(5) . . . . ? C4 C5 C6 C7 122.5(5) . . . . ? C10 C5 C6 C7 -11.4(6) . . . . ? C20 O2 C7 O5 -174.5(4) . . . . ? C20 O2 C7 C6 66.7(6) . . . . ? C20 O2 C7 C8 -47.1(6) . . . . ? O3 C6 C7 O5 77.8(5) . . . . ? C5 C6 C7 O5 -165.3(4) . . . . ? O3 C6 C7 O2 -165.8(4) . . . . ? C5 C6 C7 O2 -48.9(6) . . . . ? O3 C6 C7 C8 -43.5(4) . . . . ? C5 C6 C7 C8 73.5(5) . . . . ? O5 C7 C8 C16 -72.2(5) . . . . ? O2 C7 C8 C16 165.3(4) . . . . ? C6 C7 C8 C16 45.1(4) . . . . ? O5 C7 C8 C14 51.7(6) . . . . ? O2 C7 C8 C14 -70.7(5) . . . . ? C6 C7 C8 C14 169.0(4) . . . . ? O5 C7 C8 C9 178.8(4) . . . . ? O2 C7 C8 C9 56.3(5) . . . . ? C6 C7 C8 C9 -63.9(4) . . . . ? C7 C8 C9 C11 -135.2(4) . . . . ? C16 C8 C9 C11 121.7(5) . . . . ? C14 C8 C9 C11 -6.4(6) . . . . ? C7 C8 C9 C10 -2.5(5) . . . . ? C16 C8 C9 C10 -105.7(5) . . . . ? C14 C8 C9 C10 126.2(4) . . . . ? C11 C9 C10 C20 73.3(6) . . . . ? C8 C9 C10 C20 -54.8(5) . . . . ? C11 C9 C10 C1 -49.8(6) . . . . ? C8 C9 C10 C1 -177.8(4) . . . . ? C11 C9 C10 C5 -167.9(4) . . . . ? C8 C9 C10 C5 64.1(4) . . . . ? O1 C1 C10 C20 -47.3(6) . . . . ? C2 C1 C10 C20 72.2(6) . . . . ? O1 C1 C10 C9 73.7(5) . . . . ? C2 C1 C10 C9 -166.7(5) . . . . ? O1 C1 C10 C5 -170.7(4) . . . . ? C2 C1 C10 C5 -51.1(6) . . . . ? C6 C5 C10 C20 59.1(6) . . . . ? C4 C5 C10 C20 -73.5(6) . . . . ? C6 C5 C10 C9 -56.7(5) . . . . ? C4 C5 C10 C9 170.7(4) . . . . ? C6 C5 C10 C1 -178.0(4) . . . . ? C4 C5 C10 C1 49.5(6) . . . . ? C10 C9 C11 C12 -176.8(4) . . . . ? C8 C9 C11 C12 -49.8(6) . . . . ? C9 C11 C12 C13 66.5(6) . . . . ? C11 C12 C13 C15 -153.2(5) . . . . ? C11 C12 C13 C14 -20.5(7) . . . . ? C15 C13 C14 O6 -35.2(6) . . . . ? C12 C13 C14 O6 -166.3(5) . . . . ? C15 C13 C14 C8 93.6(6) . . . . ? C12 C13 C14 C8 -37.6(6) . . . . ? C7 C8 C14 O6 -52.3(5) . . . . ? C16 C8 C14 O6 60.8(6) . . . . ? C9 C8 C14 O6 -177.2(4) . . . . ? C7 C8 C14 C13 176.9(4) . . . . ? C16 C8 C14 C13 -70.0(6) . . . . ? C9 C8 C14 C13 52.0(6) . . . . ? C14 C13 C15 O7 33.8(8) . . . . ? C12 C13 C15 O7 163.6(6) . . . . ? C14 C13 C15 C17 -152.1(5) . . . . ? C12 C13 C15 C17 -22.3(8) . . . . ? C6 O3 C16 O4 -177.6(5) . . . . ? C6 O3 C16 C8 5.6(5) . . . . ? C7 C8 C16 O4 151.0(6) . . . . ? C14 C8 C16 O4 27.9(8) . . . . ? C9 C8 C16 O4 -97.7(6) . . . . ? C7 C8 C16 O3 -32.3(5) . . . . ? C14 C8 C16 O3 -155.5(4) . . . . ? C9 C8 C16 O3 78.9(5) . . . . ? C7 O2 C20 C10 -15.9(6) . . . . ? C9 C10 C20 O2 68.3(6) . . . . ? C1 C10 C20 O2 -167.2(4) . . . . ? C5 C10 C20 O2 -45.6(6) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O6 H6 O7 0.82 1.85 2.586(7) 148.1 . O5 H5 O6 0.82 1.88 2.615(6) 149.2 . O1 H1 O4 0.82 2.14 2.885(6) 150.5 2_656 _diffrn_measured_fraction_theta_max 0.954 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.954 _refine_diff_density_max 0.187 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.053 # Attachment '- Compound 3.cif' data_cd29614 _database_code_depnum_ccdc_archive 'CCDC 822517' #TrackingRef '- Compound 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H32 O8' _chemical_formula_weight 424.48 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 26.995(5) _cell_length_b 6.0828(12) _cell_length_c 14.322(3) _cell_angle_alpha 90.00 _cell_angle_beta 117.723(3) _cell_angle_gamma 90.00 _cell_volume 2081.8(7) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2195 _cell_measurement_theta_min 5.670 _cell_measurement_theta_max 55.282 _exptl_crystal_description prismatic _exptl_crystal_colour yellow _exptl_crystal_size_max 0.315 _exptl_crystal_size_mid 0.238 _exptl_crystal_size_min 0.104 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.354 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.49179 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5755 _diffrn_reflns_av_R_equivalents 0.0598 _diffrn_reflns_av_sigmaI/netI 0.0507 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.83 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2244 _reflns_number_gt 1906 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1176P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 10(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 2244 _refine_ls_number_parameters 279 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0670 _refine_ls_R_factor_gt 0.0610 _refine_ls_wR_factor_ref 0.1647 _refine_ls_wR_factor_gt 0.1594 _refine_ls_goodness_of_fit_ref 0.999 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.14197(13) -0.1190(7) 0.3356(2) 0.0560(9) Uani 1 1 d . . . H1 H 0.1245 -0.0034 0.3244 0.084 Uiso 1 1 calc R . . O2 O 0.24617(11) -0.0206(5) 0.04148(18) 0.0421(7) Uani 1 1 d . . . H2 H 0.2766 -0.0532 0.0906 0.063 Uiso 1 1 calc R . . O3 O 0.20453(10) 0.3446(4) 0.19401(18) 0.0357(6) Uani 1 1 d . . . O4 O 0.27795(11) 0.3826(5) 0.16027(18) 0.0401(7) Uani 1 1 d . . . H4 H 0.2642 0.4091 0.0970 0.060 Uiso 1 1 calc R . . O5 O 0.34534(15) 0.4171(6) 0.3647(2) 0.0617(9) Uani 1 1 d . . . H5 H 0.3305 0.4575 0.3030 0.093 Uiso 1 1 calc R . . O6 O 0.34051(11) -0.1089(6) 0.2181(2) 0.0499(8) Uani 1 1 d . . . O7 O 0.42597(13) -0.0782(11) 0.4330(2) 0.0943(17) Uani 1 1 d . . . O8 O 0.0626(2) 0.2174(12) 0.2875(4) 0.124(2) Uani 1 1 d . . . C1 C 0.14451(16) -0.1860(7) 0.2423(3) 0.0404(9) Uani 1 1 d . . . H1A H 0.1616 -0.3324 0.2568 0.048 Uiso 1 1 calc R . . C2 C 0.08652(17) -0.2126(9) 0.1524(3) 0.0499(11) Uani 1 1 d . . . H2A H 0.0665 -0.0747 0.1412 0.060 Uiso 1 1 calc R . . H2B H 0.0667 -0.3228 0.1710 0.060 Uiso 1 1 calc R . . C3 C 0.08684(18) -0.2803(8) 0.0506(4) 0.0499(11) Uani 1 1 d . . . H3A H 0.0486 -0.2971 -0.0045 0.060 Uiso 1 1 calc R . . H3B H 0.1054 -0.4215 0.0607 0.060 Uiso 1 1 calc R . . C4 C 0.11668(15) -0.1120(7) 0.0156(3) 0.0406(9) Uani 1 1 d . . . C5 C 0.17709(13) -0.0822(6) 0.1066(2) 0.0301(7) Uani 1 1 d . . . H5A H 0.1951 -0.2252 0.1128 0.036 Uiso 1 1 calc R . . C6 C 0.21237(14) 0.0796(6) 0.0815(2) 0.0309(8) Uani 1 1 d . . . H6 H 0.1861 0.1763 0.0257 0.037 Uiso 1 1 calc R . . C7 C 0.24604(14) 0.2262(6) 0.1775(2) 0.0296(7) Uani 1 1 d . . . C8 C 0.28327(14) 0.1002(6) 0.2799(2) 0.0289(7) Uani 1 1 d . . . C9 C 0.24615(14) -0.0793(7) 0.2980(2) 0.0306(7) Uani 1 1 d . . . H9 H 0.2561 -0.2226 0.2802 0.037 Uiso 1 1 calc R . . C10 C 0.18363(15) -0.0351(6) 0.2189(3) 0.0314(8) Uani 1 1 d . . . C11 C 0.25896(16) -0.0882(8) 0.4142(2) 0.0435(9) Uani 1 1 d . . . H11A H 0.2429 -0.2212 0.4262 0.052 Uiso 1 1 calc R . . H11B H 0.2414 0.0363 0.4293 0.052 Uiso 1 1 calc R . . C12 C 0.32234(17) -0.0846(9) 0.4905(3) 0.0509(11) Uani 1 1 d . . . H12A H 0.3281 -0.0611 0.5619 0.061 Uiso 1 1 calc R . . H12B H 0.3384 -0.2261 0.4885 0.061 Uiso 1 1 calc R . . C13 C 0.35244(16) 0.0967(9) 0.4619(3) 0.0477(10) Uani 1 1 d . . . H13 H 0.3795 0.1758 0.5245 0.057 Uiso 1 1 calc R . . C14 C 0.31181(17) 0.2532(7) 0.3781(3) 0.0405(9) Uani 1 1 d . . . H14 H 0.2847 0.3163 0.3982 0.049 Uiso 1 1 calc R . . C15 C 0.33409(14) -0.0137(7) 0.2856(3) 0.0370(9) Uani 1 1 d . . . C16 C 0.37975(17) -0.0066(10) 0.4030(3) 0.0542(12) Uani 1 1 d . . . C18 C 0.12136(19) -0.2059(10) -0.0798(3) 0.0595(13) Uani 1 1 d . . . H18A H 0.0846 -0.2303 -0.1369 0.089 Uiso 1 1 calc R . . H18B H 0.1414 -0.3426 -0.0604 0.089 Uiso 1 1 calc R . . H18C H 0.1410 -0.1034 -0.1016 0.089 Uiso 1 1 calc R . . C19 C 0.08209(18) 0.0983(9) -0.0207(3) 0.0543(11) Uani 1 1 d . . . H19A H 0.0466 0.0664 -0.0801 0.081 Uiso 1 1 calc R . . H19B H 0.1017 0.2049 -0.0406 0.081 Uiso 1 1 calc R . . H19C H 0.0762 0.1560 0.0358 0.081 Uiso 1 1 calc R . . C20 C 0.17280(16) 0.2086(6) 0.2286(3) 0.0351(8) Uani 1 1 d . . . H20A H 0.1332 0.2396 0.1863 0.042 Uiso 1 1 calc R . . H20B H 0.1830 0.2424 0.3015 0.042 Uiso 1 1 calc R . . C21 C 0.0255(2) 0.2331(14) 0.3117(4) 0.082(2) Uani 1 1 d . . . C22 C -0.0060(3) 0.4328(15) 0.2909(5) 0.095(2) Uani 1 1 d . . . H22A H -0.0032 0.4900 0.3556 0.142 Uiso 1 1 calc R . . H22B H -0.0446 0.4037 0.2427 0.142 Uiso 1 1 calc R . . H22C H 0.0086 0.5385 0.2603 0.142 Uiso 1 1 calc R . . C23 C 0.0134(4) 0.0550(14) 0.3624(7) 0.121(3) Uani 1 1 d . . . H23A H 0.0246 -0.0806 0.3436 0.182 Uiso 1 1 calc R . . H23B H -0.0261 0.0511 0.3404 0.182 Uiso 1 1 calc R . . H23C H 0.0335 0.0746 0.4375 0.182 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 0.061(2) 0.073(2) 0.0524(16) 0.0121(17) 0.0418(16) 0.0092(18) O2 0.0394(13) 0.0656(19) 0.0249(11) -0.0138(13) 0.0180(11) -0.0062(14) O3 0.0448(14) 0.0310(13) 0.0367(12) 0.0035(11) 0.0236(12) 0.0070(11) O4 0.0462(15) 0.0479(17) 0.0252(11) 0.0032(12) 0.0157(11) -0.0107(13) O5 0.073(2) 0.062(2) 0.0357(14) -0.0078(15) 0.0130(15) -0.0266(18) O6 0.0421(15) 0.071(2) 0.0375(13) -0.0054(15) 0.0190(12) 0.0117(15) O7 0.0394(17) 0.180(5) 0.0454(16) 0.015(3) 0.0046(14) 0.034(3) O8 0.101(4) 0.161(6) 0.116(4) -0.009(4) 0.056(3) 0.053(4) C1 0.047(2) 0.038(2) 0.047(2) 0.0061(18) 0.0314(19) 0.0075(17) C2 0.040(2) 0.057(3) 0.061(3) 0.005(2) 0.031(2) -0.0051(19) C3 0.039(2) 0.051(3) 0.058(2) -0.009(2) 0.020(2) -0.0066(19) C4 0.0323(18) 0.049(2) 0.0371(18) -0.0065(19) 0.0131(16) -0.0036(18) C5 0.0291(16) 0.0348(18) 0.0253(14) -0.0021(15) 0.0117(13) 0.0040(15) C6 0.0316(18) 0.041(2) 0.0163(13) -0.0011(14) 0.0082(13) 0.0014(15) C7 0.0341(18) 0.0320(18) 0.0227(15) 0.0020(14) 0.0133(14) 0.0023(15) C8 0.0326(17) 0.0348(18) 0.0175(13) -0.0007(14) 0.0100(13) 0.0025(14) C9 0.0381(18) 0.0316(17) 0.0253(15) 0.0023(14) 0.0175(14) 0.0049(15) C10 0.0333(18) 0.038(2) 0.0272(15) 0.0007(14) 0.0174(15) 0.0027(15) C11 0.051(2) 0.056(2) 0.0255(15) 0.0091(18) 0.0189(16) 0.002(2) C12 0.054(2) 0.067(3) 0.0264(16) 0.008(2) 0.0144(17) 0.006(2) C13 0.043(2) 0.067(3) 0.0188(15) -0.0008(18) 0.0018(16) -0.005(2) C14 0.047(2) 0.046(2) 0.0234(15) -0.0046(16) 0.0126(16) -0.0020(19) C15 0.0298(17) 0.050(2) 0.0297(17) 0.0047(17) 0.0125(15) 0.0031(17) C16 0.033(2) 0.086(3) 0.0323(19) 0.010(2) 0.0053(17) 0.002(2) C18 0.046(2) 0.083(4) 0.039(2) -0.024(2) 0.0106(19) -0.019(2) C19 0.038(2) 0.064(3) 0.048(2) 0.008(2) 0.0089(19) 0.002(2) C20 0.042(2) 0.037(2) 0.0320(17) 0.0009(15) 0.0215(16) 0.0058(16) C21 0.062(3) 0.117(6) 0.048(3) -0.025(3) 0.010(3) 0.030(4) C22 0.079(4) 0.123(6) 0.087(4) 0.009(5) 0.043(4) 0.030(4) C23 0.133(7) 0.080(5) 0.130(7) -0.012(5) 0.044(6) 0.003(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.429(4) . ? O1 H1 0.8200 . ? O2 C6 1.421(4) . ? O2 H2 0.8200 . ? O3 C20 1.435(4) . ? O3 C7 1.441(4) . ? O4 C7 1.381(4) . ? O4 H4 0.8200 . ? O5 C14 1.418(5) . ? O5 H5 0.8200 . ? O6 C15 1.205(4) . ? O7 C16 1.197(5) . ? O8 C21 1.208(7) . ? C1 C2 1.503(6) . ? C1 C10 1.549(5) . ? C1 H1A 0.9800 . ? C2 C3 1.519(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.524(6) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C19 1.525(7) . ? C4 C18 1.540(5) . ? C4 C5 1.553(5) . ? C5 C6 1.524(5) . ? C5 C10 1.561(4) . ? C5 H5A 0.9800 . ? C6 C7 1.533(5) . ? C6 H6 0.9800 . ? C7 C8 1.542(4) . ? C8 C15 1.505(5) . ? C8 C14 1.558(5) . ? C8 C9 1.583(5) . ? C9 C11 1.536(4) . ? C9 C10 1.557(5) . ? C9 H9 0.9800 . ? C10 C20 1.529(5) . ? C11 C12 1.544(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.535(6) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C16 1.492(6) . ? C13 C14 1.525(6) . ? C13 H13 0.9800 . ? C14 H14 0.9800 . ? C15 C16 1.556(5) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C23 1.424(11) . ? C21 C22 1.432(10) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? C6 O2 H2 109.5 . . ? C20 O3 C7 113.8(3) . . ? C7 O4 H4 109.5 . . ? C14 O5 H5 109.5 . . ? C21 O8 H1 132.6 . . ? O1 C1 C2 110.4(3) . . ? O1 C1 C10 111.6(3) . . ? C2 C1 C10 114.9(3) . . ? O1 C1 H1A 106.5 . . ? C2 C1 H1A 106.5 . . ? C10 C1 H1A 106.5 . . ? C1 C2 C3 112.5(3) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 111.9(4) . . ? C2 C3 H3A 109.2 . . ? C4 C3 H3A 109.2 . . ? C2 C3 H3B 109.2 . . ? C4 C3 H3B 109.2 . . ? H3A C3 H3B 107.9 . . ? C3 C4 C19 110.0(3) . . ? C3 C4 C18 108.4(4) . . ? C19 C4 C18 107.4(4) . . ? C3 C4 C5 108.2(3) . . ? C19 C4 C5 115.2(3) . . ? C18 C4 C5 107.4(3) . . ? C6 C5 C4 113.9(3) . . ? C6 C5 C10 109.9(3) . . ? C4 C5 C10 117.2(3) . . ? C6 C5 H5A 104.8 . . ? C4 C5 H5A 104.8 . . ? C10 C5 H5A 104.8 . . ? O2 C6 C5 114.0(3) . . ? O2 C6 C7 112.8(3) . . ? C5 C6 C7 109.8(2) . . ? O2 C6 H6 106.6 . . ? C5 C6 H6 106.6 . . ? C7 C6 H6 106.6 . . ? O4 C7 O3 106.4(3) . . ? O4 C7 C6 113.5(2) . . ? O3 C7 C6 104.8(3) . . ? O4 C7 C8 109.1(3) . . ? O3 C7 C8 107.8(2) . . ? C6 C7 C8 114.6(3) . . ? C15 C8 C7 117.0(2) . . ? C15 C8 C14 99.8(3) . . ? C7 C8 C14 113.0(3) . . ? C15 C8 C9 107.7(3) . . ? C7 C8 C9 108.4(3) . . ? C14 C8 C9 110.5(2) . . ? C11 C9 C10 114.6(3) . . ? C11 C9 C8 111.2(3) . . ? C10 C9 C8 108.5(3) . . ? C11 C9 H9 107.5 . . ? C10 C9 H9 107.5 . . ? C8 C9 H9 107.5 . . ? C20 C10 C1 112.1(3) . . ? C20 C10 C9 106.8(3) . . ? C1 C10 C9 111.0(3) . . ? C20 C10 C5 109.7(3) . . ? C1 C10 C5 110.6(3) . . ? C9 C10 C5 106.4(3) . . ? C9 C11 C12 112.5(3) . . ? C9 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? C9 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? C13 C12 C11 111.8(3) . . ? C13 C12 H12A 109.3 . . ? C11 C12 H12A 109.3 . . ? C13 C12 H12B 109.3 . . ? C11 C12 H12B 109.3 . . ? H12A C12 H12B 107.9 . . ? C16 C13 C14 100.5(3) . . ? C16 C13 C12 108.1(4) . . ? C14 C13 C12 112.5(3) . . ? C16 C13 H13 111.7 . . ? C14 C13 H13 111.7 . . ? C12 C13 H13 111.7 . . ? O5 C14 C13 106.0(3) . . ? O5 C14 C8 112.1(3) . . ? C13 C14 C8 102.1(3) . . ? O5 C14 H14 112.0 . . ? C13 C14 H14 112.0 . . ? C8 C14 H14 112.0 . . ? O6 C15 C8 130.2(3) . . ? O6 C15 C16 122.8(3) . . ? C8 C15 C16 106.8(3) . . ? O7 C16 C13 131.1(4) . . ? O7 C16 C15 123.2(4) . . ? C13 C16 C15 105.7(3) . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O3 C20 C10 111.0(3) . . ? O3 C20 H20A 109.4 . . ? C10 C20 H20A 109.4 . . ? O3 C20 H20B 109.4 . . ? C10 C20 H20B 109.4 . . ? H20A C20 H20B 108.0 . . ? O8 C21 C23 120.3(7) . . ? O8 C21 C22 119.9(8) . . ? C23 C21 C22 119.8(6) . . ? C21 C22 H22A 109.5 . . ? C21 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C21 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C21 C23 H23A 109.5 . . ? C21 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C21 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 179.1(4) . . . . ? C10 C1 C2 C3 51.9(5) . . . . ? C1 C2 C3 C4 -59.7(5) . . . . ? C2 C3 C4 C19 -69.6(4) . . . . ? C2 C3 C4 C18 173.2(4) . . . . ? C2 C3 C4 C5 57.0(4) . . . . ? C3 C4 C5 C6 178.9(3) . . . . ? C19 C4 C5 C6 -57.6(4) . . . . ? C18 C4 C5 C6 62.0(4) . . . . ? C3 C4 C5 C10 -50.8(4) . . . . ? C19 C4 C5 C10 72.7(4) . . . . ? C18 C4 C5 C10 -167.7(4) . . . . ? C4 C5 C6 O2 -94.6(3) . . . . ? C10 C5 C6 O2 131.6(3) . . . . ? C4 C5 C6 C7 137.7(3) . . . . ? C10 C5 C6 C7 3.9(4) . . . . ? C20 O3 C7 O4 -171.3(3) . . . . ? C20 O3 C7 C6 68.2(3) . . . . ? C20 O3 C7 C8 -54.3(4) . . . . ? O2 C6 C7 O4 53.5(4) . . . . ? C5 C6 C7 O4 -178.1(3) . . . . ? O2 C6 C7 O3 169.2(3) . . . . ? C5 C6 C7 O3 -62.4(3) . . . . ? O2 C6 C7 C8 -72.8(4) . . . . ? C5 C6 C7 C8 55.5(4) . . . . ? O4 C7 C8 C15 -57.6(4) . . . . ? O3 C7 C8 C15 -172.8(3) . . . . ? C6 C7 C8 C15 71.0(4) . . . . ? O4 C7 C8 C14 57.6(3) . . . . ? O3 C7 C8 C14 -57.6(4) . . . . ? C6 C7 C8 C14 -173.8(3) . . . . ? O4 C7 C8 C9 -179.6(3) . . . . ? O3 C7 C8 C9 65.3(3) . . . . ? C6 C7 C8 C9 -51.0(3) . . . . ? C15 C8 C9 C11 94.9(3) . . . . ? C7 C8 C9 C11 -137.6(3) . . . . ? C14 C8 C9 C11 -13.2(4) . . . . ? C15 C8 C9 C10 -138.3(3) . . . . ? C7 C8 C9 C10 -10.8(3) . . . . ? C14 C8 C9 C10 113.6(3) . . . . ? O1 C1 C10 C20 -46.4(4) . . . . ? C2 C1 C10 C20 80.2(4) . . . . ? O1 C1 C10 C9 72.9(4) . . . . ? C2 C1 C10 C9 -160.5(3) . . . . ? O1 C1 C10 C5 -169.2(3) . . . . ? C2 C1 C10 C5 -42.6(4) . . . . ? C11 C9 C10 C20 74.8(4) . . . . ? C8 C9 C10 C20 -50.0(3) . . . . ? C11 C9 C10 C1 -47.7(4) . . . . ? C8 C9 C10 C1 -172.5(3) . . . . ? C11 C9 C10 C5 -168.1(3) . . . . ? C8 C9 C10 C5 67.1(3) . . . . ? C6 C5 C10 C20 51.4(4) . . . . ? C4 C5 C10 C20 -80.7(4) . . . . ? C6 C5 C10 C1 175.6(3) . . . . ? C4 C5 C10 C1 43.5(4) . . . . ? C6 C5 C10 C9 -63.8(4) . . . . ? C4 C5 C10 C9 164.1(3) . . . . ? C10 C9 C11 C12 -168.3(4) . . . . ? C8 C9 C11 C12 -44.9(5) . . . . ? C9 C11 C12 C13 47.7(5) . . . . ? C11 C12 C13 C16 -100.1(4) . . . . ? C11 C12 C13 C14 9.9(5) . . . . ? C16 C13 C14 O5 -68.6(4) . . . . ? C12 C13 C14 O5 176.6(3) . . . . ? C16 C13 C14 C8 48.9(4) . . . . ? C12 C13 C14 C8 -65.9(4) . . . . ? C15 C8 C14 O5 67.0(4) . . . . ? C7 C8 C14 O5 -58.1(4) . . . . ? C9 C8 C14 O5 -179.8(3) . . . . ? C15 C8 C14 C13 -46.0(3) . . . . ? C7 C8 C14 C13 -171.1(3) . . . . ? C9 C8 C14 C13 67.2(4) . . . . ? C7 C8 C15 O6 -37.0(6) . . . . ? C14 C8 C15 O6 -159.3(4) . . . . ? C9 C8 C15 O6 85.4(5) . . . . ? C7 C8 C15 C16 147.7(3) . . . . ? C14 C8 C15 C16 25.4(4) . . . . ? C9 C8 C15 C16 -89.9(4) . . . . ? C14 C13 C16 O7 149.4(7) . . . . ? C12 C13 C16 O7 -92.5(7) . . . . ? C14 C13 C16 C15 -32.2(5) . . . . ? C12 C13 C16 C15 85.8(4) . . . . ? O6 C15 C16 O7 6.7(8) . . . . ? C8 C15 C16 O7 -177.6(6) . . . . ? O6 C15 C16 C13 -171.8(4) . . . . ? C8 C15 C16 C13 3.9(5) . . . . ? C7 O3 C20 C10 -10.9(4) . . . . ? C1 C10 C20 O3 -172.8(3) . . . . ? C9 C10 C20 O3 65.4(3) . . . . ? C5 C10 C20 O3 -49.5(4) . . . . ? H1 O8 C21 C23 -11.7 . . . . ? H1 O8 C21 C22 167.3 . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O5 H5 O4 0.82 1.92 2.640(4) 145.4 . O4 H4 O2 0.82 1.92 2.715(3) 163.7 4 O2 H2 O6 0.82 1.87 2.680(4) 169.6 . O1 H1 O8 0.82 2.01 2.807(6) 162.7 . _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.439 _refine_diff_density_min -0.308 _refine_diff_density_rms 0.061 # Attachment '- Compound 4.cif' data_mo_dm1024_0m _database_code_depnum_ccdc_archive 'CCDC 822518' #TrackingRef '- Compound 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19.50 H28 O8.50' _chemical_formula_weight 398.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 9.6172(17) _cell_length_b 14.543(3) _cell_length_c 27.025(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3779.9(12) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7656 _cell_measurement_theta_min 2.539 _cell_measurement_theta_max 26.490 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.307 _exptl_crystal_size_mid 0.228 _exptl_crystal_size_min 0.050 _exptl_crystal_density_meas 1.400 _exptl_crystal_density_diffrn 1.400 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1704 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6548 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_process_details 'SADABS V2008/1 (Bruker AXS)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 36736 _diffrn_reflns_av_R_equivalents 0.0733 _diffrn_reflns_av_sigmaI/netI 0.0380 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4157 _reflns_number_gt 3147 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1031P)^2^+1.3189P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0024(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(10) _chemical_absolute_configuration ad _refine_ls_number_reflns 4157 _refine_ls_number_parameters 534 _refine_ls_number_restraints 9 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0628 _refine_ls_wR_factor_ref 0.1948 _refine_ls_wR_factor_gt 0.1660 _refine_ls_goodness_of_fit_ref 1.209 _refine_ls_restrained_S_all 1.208 _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 0.8041(4) 0.4188(3) 0.96141(13) 0.0421(9) Uani 1 1 d D . . O2 O 0.6615(4) 0.2432(3) 0.84548(16) 0.0522(11) Uani 1 1 d . . . O3 O 0.4073(4) 0.4057(4) 0.80100(16) 0.0618(13) Uani 1 1 d . . . O4 O 0.2220(4) 0.3949(3) 0.85043(17) 0.0604(12) Uani 1 1 d . . . O5 O 0.4711(5) 0.2125(4) 0.80070(17) 0.0688(14) Uani 1 1 d D . . O6 O 0.2805(5) 0.1774(3) 0.86793(18) 0.0604(12) Uani 1 1 d D . . O7 O 0.0788(4) 0.3499(4) 0.96271(18) 0.0629(13) Uani 1 1 d . . . O8 O 0.0585(5) 0.2460(4) 0.9049(2) 0.0704(14) Uani 1 1 d D . . O9 O 0.2291(4) 0.9898(3) 0.95234(15) 0.0427(9) Uani 1 1 d D . . O10 O 0.3917(4) 0.8503(3) 0.82682(13) 0.0431(9) Uani 1 1 d . . . O11 O 0.6304(4) 0.7169(3) 0.90073(16) 0.0493(10) Uani 1 1 d . . . O12 O 0.8197(4) 0.8028(3) 0.91192(17) 0.0566(11) Uani 1 1 d . . . O13 O 0.5835(5) 0.7754(3) 0.80104(16) 0.0558(12) Uani 1 1 d D . . O14 O 0.7557(5) 0.9151(4) 0.80688(16) 0.0647(13) Uani 1 1 d D . . O15 O 0.9828(5) 0.9586(4) 0.85489(18) 0.0705(14) Uani 1 1 d . . . O16 O 0.9647(4) 1.0277(3) 0.92813(19) 0.0607(13) Uani 1 1 d D . . O17 O 0.6738(11) 0.1036(8) 0.7446(4) 0.158(3) Uiso 1 1 d . . . H17 H 0.6384 0.1549 0.7460 0.237 Uiso 1 1 calc RD . . C1 C 0.7590(5) 0.4606(4) 0.91561(19) 0.0394(12) Uani 1 1 d . . . H1A H 0.7001 0.5133 0.9242 0.047 Uiso 1 1 calc R . . C2 C 0.8837(6) 0.4976(5) 0.8869(2) 0.0538(16) Uani 1 1 d . . . H2A H 0.9330 0.5415 0.9075 0.065 Uiso 1 1 calc R . . H2B H 0.9468 0.4471 0.8799 0.065 Uiso 1 1 calc R . . C3 C 0.8442(7) 0.5434(5) 0.8389(2) 0.0575(17) Uani 1 1 d . . . H3A H 0.9277 0.5663 0.8230 0.069 Uiso 1 1 calc R . . H3B H 0.7850 0.5958 0.8461 0.069 Uiso 1 1 calc R . . C4 C 0.7675(6) 0.4787(4) 0.8029(2) 0.0497(15) Uani 1 1 d . . . C5 C 0.6425(6) 0.4386(4) 0.83173(19) 0.0418(13) Uani 1 1 d . . . H5 H 0.5821 0.4915 0.8384 0.050 Uiso 1 1 calc R . . C6 C 0.5522(6) 0.3719(5) 0.8021(2) 0.0493(15) Uani 1 1 d . . . H6A H 0.5889 0.3625 0.7687 0.059 Uiso 1 1 calc R . . C7 C 0.5354(6) 0.2811(4) 0.8296(2) 0.0453(14) Uani 1 1 d . . . C8 C 0.4377(5) 0.3130(4) 0.87108(18) 0.0343(11) Uani 1 1 d . . . C9 C 0.5226(5) 0.3771(4) 0.90688(18) 0.0343(11) Uani 1 1 d . . . H9 H 0.4752 0.4368 0.9066 0.041 Uiso 1 1 calc R . . C10 C 0.6700(5) 0.3941(4) 0.88414(18) 0.0327(11) Uani 1 1 d . . . C11 C 0.5160(5) 0.3423(4) 0.96031(19) 0.0412(13) Uani 1 1 d . . . H11A H 0.5629 0.2834 0.9627 0.049 Uiso 1 1 calc R . . H11B H 0.5632 0.3854 0.9820 0.049 Uiso 1 1 calc R . . C12 C 0.3650(6) 0.3320(4) 0.9764(2) 0.0439(13) Uani 1 1 d . . . H12A H 0.3197 0.3915 0.9744 0.053 Uiso 1 1 calc R . . H12B H 0.3626 0.3125 1.0108 0.053 Uiso 1 1 calc R . . C13 C 0.2827(5) 0.2623(4) 0.9449(2) 0.0410(12) Uani 1 1 d . . . H13 H 0.2767 0.2069 0.9654 0.049 Uiso 1 1 calc R . . C14 C 0.3667(6) 0.2328(4) 0.8989(2) 0.0410(12) Uani 1 1 d . . . H14A H 0.4415 0.1928 0.9108 0.049 Uiso 1 1 calc R . . C15 C 0.3385(6) 0.3737(5) 0.8419(2) 0.0488(15) Uani 1 1 d . . . C16 C 0.7399(5) 0.3013(4) 0.8789(2) 0.0404(12) Uani 1 1 d . . . H16A H 0.8335 0.3095 0.8663 0.048 Uiso 1 1 calc R . . H16B H 0.7462 0.2720 0.9111 0.048 Uiso 1 1 calc R . . C17 C 0.8676(8) 0.4066(5) 0.7808(3) 0.0633(18) Uani 1 1 d . . . H17A H 0.8158 0.3638 0.7610 0.095 Uiso 1 1 calc R . . H17B H 0.9135 0.3743 0.8071 0.095 Uiso 1 1 calc R . . H17C H 0.9356 0.4369 0.7605 0.095 Uiso 1 1 calc R . . C18 C 0.7092(9) 0.5373(6) 0.7608(3) 0.073(2) Uani 1 1 d . . . H18A H 0.6414 0.5793 0.7738 0.110 Uiso 1 1 calc R . . H18B H 0.6662 0.4981 0.7366 0.110 Uiso 1 1 calc R . . H18C H 0.7834 0.5712 0.7456 0.110 Uiso 1 1 calc R . . C19 C 0.1336(6) 0.2924(5) 0.9373(2) 0.0515(15) Uani 1 1 d . . . C20 C 0.2694(5) 0.8951(4) 0.95821(19) 0.0381(12) Uani 1 1 d . . . H20 H 0.3188 0.8889 0.9897 0.046 Uiso 1 1 calc R . . C21 C 0.1385(6) 0.8382(4) 0.9607(2) 0.0464(14) Uani 1 1 d . . . H21A H 0.0836 0.8492 0.9312 0.056 Uiso 1 1 calc R . . H21B H 0.0839 0.8577 0.9890 0.056 Uiso 1 1 calc R . . C22 C 0.1673(6) 0.7361(4) 0.9650(2) 0.0521(15) Uani 1 1 d . . . H22A H 0.0795 0.7033 0.9663 0.063 Uiso 1 1 calc R . . H22B H 0.2160 0.7245 0.9959 0.063 Uiso 1 1 calc R . . C23 C 0.2543(6) 0.6984(4) 0.9221(2) 0.0481(14) Uani 1 1 d . . . C24 C 0.3872(5) 0.7573(4) 0.9193(2) 0.0377(12) Uani 1 1 d . . . H24 H 0.4354 0.7465 0.9507 0.045 Uiso 1 1 calc R . . C25 C 0.4919(6) 0.7295(4) 0.8791(2) 0.0446(13) Uani 1 1 d . . . H25 H 0.4613 0.6741 0.8615 0.053 Uiso 1 1 calc R . . C26 C 0.5162(5) 0.8097(4) 0.84320(19) 0.0378(12) Uani 1 1 d . . . C27 C 0.6085(5) 0.8705(4) 0.87614(19) 0.0353(11) Uani 1 1 d . . . C28 C 0.5170(5) 0.9055(4) 0.92112(18) 0.0339(11) Uani 1 1 d . . . H28 H 0.5575 0.8777 0.9509 0.041 Uiso 1 1 calc R . . C29 C 0.3674(5) 0.8646(3) 0.91641(18) 0.0320(11) Uani 1 1 d . . . C30 C 0.5309(6) 1.0084(4) 0.9277(2) 0.0432(13) Uani 1 1 d . . . H30A H 0.4853 1.0270 0.9581 0.052 Uiso 1 1 calc R . . H30B H 0.4856 1.0397 0.9004 0.052 Uiso 1 1 calc R . . C31 C 0.6827(6) 1.0358(4) 0.9295(2) 0.0485(14) Uani 1 1 d . . . H31A H 0.7288 1.0012 0.9555 0.058 Uiso 1 1 calc R . . H31B H 0.6895 1.1005 0.9378 0.058 Uiso 1 1 calc R . . C32 C 0.7582(6) 1.0184(4) 0.8800(2) 0.0434(13) Uani 1 1 d . . . H32 H 0.7544 1.0769 0.8620 0.052 Uiso 1 1 calc R . . C33 C 0.6779(6) 0.9495(4) 0.8479(2) 0.0422(13) Uani 1 1 d . . . H33 H 0.6013 0.9847 0.8333 0.051 Uiso 1 1 calc R . . C34 C 0.7042(6) 0.7963(4) 0.8974(2) 0.0425(13) Uani 1 1 d . . . C35 C 0.3138(5) 0.8949(4) 0.86570(18) 0.0370(11) Uani 1 1 d . . . H35A H 0.2161 0.8792 0.8627 0.044 Uiso 1 1 calc R . . H35B H 0.3227 0.9611 0.8625 0.044 Uiso 1 1 calc R . . C36 C 0.1688(7) 0.6950(5) 0.8734(3) 0.0632(18) Uani 1 1 d . . . H36A H 0.1027 0.6456 0.8751 0.095 Uiso 1 1 calc R . . H36B H 0.2304 0.6850 0.8459 0.095 Uiso 1 1 calc R . . H36C H 0.1205 0.7521 0.8690 0.095 Uiso 1 1 calc R . . C37 C 0.2994(9) 0.5986(5) 0.9351(3) 0.074(2) Uani 1 1 d . . . H37A H 0.3486 0.5985 0.9660 0.112 Uiso 1 1 calc R . . H37B H 0.3590 0.5753 0.9095 0.112 Uiso 1 1 calc R . . H37C H 0.2185 0.5602 0.9377 0.112 Uiso 1 1 calc R . . C38 C 0.9121(6) 0.9969(4) 0.8861(2) 0.0469(14) Uani 1 1 d . . . C39 C 0.827(2) 0.1119(13) 0.7505(7) 0.186(7) Uiso 1 1 d . . . H39A H 0.8471 0.1439 0.7807 0.279 Uiso 1 1 calc R . . H39B H 0.8644 0.1454 0.7230 0.279 Uiso 1 1 calc R . . H39C H 0.8672 0.0516 0.7516 0.279 Uiso 1 1 calc R . . H1 H 0.879(4) 0.394(4) 0.958(2) 0.054(19) Uiso 1 1 d D . . H5A H 0.456(9) 0.175(7) 0.778(3) 0.14(4) Uiso 1 1 d D . . H6 H 0.313(10) 0.165(7) 0.8400(18) 0.11(4) Uiso 1 1 d D . . H8 H 0.124(7) 0.229(6) 0.888(3) 0.09(3) Uiso 1 1 d D . . H9A H 0.255(9) 1.008(6) 0.9795(16) 0.09(3) Uiso 1 1 d D . . H13A H 0.654(5) 0.805(4) 0.796(3) 0.05(2) Uiso 1 1 d D . . H14 H 0.837(4) 0.917(7) 0.817(3) 0.11(4) Uiso 1 1 d D . . H16 H 1.051(2) 1.025(5) 0.931(2) 0.051(18) Uiso 1 1 d 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 0.0253(18) 0.065(3) 0.0356(19) -0.0051(18) -0.0051(16) 0.0020(18) O2 0.041(2) 0.059(2) 0.056(2) -0.024(2) -0.0024(19) 0.004(2) O3 0.044(2) 0.094(3) 0.047(2) 0.023(2) -0.016(2) -0.012(2) O4 0.033(2) 0.077(3) 0.072(3) 0.011(2) -0.014(2) 0.009(2) O5 0.064(3) 0.090(3) 0.052(3) -0.034(3) -0.001(2) -0.026(3) O6 0.061(3) 0.058(3) 0.062(3) -0.010(2) -0.006(3) -0.018(2) O7 0.035(2) 0.087(3) 0.067(3) 0.004(3) 0.006(2) 0.014(2) O8 0.031(2) 0.093(4) 0.087(4) -0.005(3) -0.013(3) -0.012(3) O9 0.0277(18) 0.053(2) 0.048(2) -0.0126(19) -0.0046(17) 0.0076(17) O10 0.0329(19) 0.068(2) 0.0284(18) -0.0056(17) -0.0032(15) 0.0051(18) O11 0.036(2) 0.045(2) 0.067(3) 0.0017(19) -0.0012(19) 0.0096(18) O12 0.031(2) 0.070(3) 0.069(3) 0.002(2) -0.007(2) 0.011(2) O13 0.046(3) 0.078(3) 0.044(2) -0.023(2) 0.004(2) 0.001(2) O14 0.050(3) 0.104(4) 0.040(2) -0.008(2) 0.013(2) -0.013(3) O15 0.041(2) 0.106(4) 0.064(3) -0.014(3) 0.009(2) 0.006(3) O16 0.028(2) 0.070(3) 0.084(3) -0.029(3) -0.013(2) 0.005(2) C1 0.029(3) 0.052(3) 0.038(3) -0.008(2) -0.006(2) 0.003(2) C2 0.040(3) 0.073(4) 0.048(3) -0.003(3) -0.004(3) -0.019(3) C3 0.056(4) 0.066(4) 0.049(3) 0.006(3) -0.003(3) -0.024(3) C4 0.044(3) 0.068(4) 0.037(3) 0.004(3) 0.006(3) -0.009(3) C5 0.036(3) 0.058(3) 0.032(3) 0.002(3) -0.004(2) -0.002(3) C6 0.038(3) 0.074(4) 0.035(3) 0.004(3) -0.006(2) -0.006(3) C7 0.038(3) 0.057(3) 0.040(3) -0.017(3) -0.002(3) -0.010(3) C8 0.025(2) 0.046(3) 0.031(3) -0.004(2) -0.005(2) 0.002(2) C9 0.025(2) 0.043(3) 0.034(3) -0.003(2) -0.002(2) 0.003(2) C10 0.027(2) 0.042(3) 0.029(2) -0.005(2) -0.001(2) 0.003(2) C11 0.030(3) 0.061(4) 0.033(3) -0.002(3) -0.004(2) 0.002(3) C12 0.032(3) 0.062(3) 0.038(3) -0.001(3) 0.003(2) 0.002(3) C13 0.031(3) 0.050(3) 0.042(3) 0.002(3) -0.002(2) 0.001(2) C14 0.034(3) 0.046(3) 0.042(3) 0.000(2) -0.007(2) -0.001(2) C15 0.037(3) 0.064(4) 0.046(3) 0.006(3) -0.016(3) -0.012(3) C16 0.031(3) 0.049(3) 0.041(3) -0.008(2) -0.002(2) 0.005(2) C17 0.060(4) 0.074(4) 0.056(4) -0.004(3) 0.017(3) -0.007(4) C18 0.071(5) 0.092(5) 0.056(4) 0.023(4) 0.002(4) -0.009(4) C19 0.030(3) 0.072(4) 0.053(3) 0.015(3) 0.004(3) 0.003(3) C20 0.031(3) 0.048(3) 0.036(3) 0.000(2) -0.001(2) 0.006(2) C21 0.028(3) 0.063(3) 0.048(3) 0.002(3) 0.012(2) -0.005(3) C22 0.042(3) 0.057(3) 0.057(4) 0.015(3) 0.003(3) -0.010(3) C23 0.041(3) 0.042(3) 0.061(4) 0.006(3) -0.005(3) -0.006(3) C24 0.030(3) 0.042(3) 0.041(3) 0.001(2) -0.005(2) 0.000(2) C25 0.040(3) 0.040(3) 0.054(3) -0.009(3) -0.002(3) 0.003(2) C26 0.030(3) 0.048(3) 0.036(3) -0.008(2) 0.001(2) 0.002(2) C27 0.026(2) 0.044(3) 0.035(3) -0.004(2) -0.003(2) 0.005(2) C28 0.028(2) 0.040(3) 0.033(3) -0.002(2) -0.007(2) 0.004(2) C29 0.027(2) 0.036(3) 0.033(3) -0.001(2) -0.001(2) 0.001(2) C30 0.029(3) 0.042(3) 0.058(3) -0.013(3) 0.002(3) 0.002(2) C31 0.032(3) 0.056(3) 0.057(4) -0.014(3) -0.002(3) -0.005(3) C32 0.034(3) 0.049(3) 0.048(3) 0.003(3) -0.002(2) 0.000(3) C33 0.029(3) 0.061(3) 0.037(3) 0.003(3) -0.003(2) 0.002(3) C34 0.029(3) 0.059(3) 0.039(3) -0.003(3) 0.000(2) 0.008(3) C35 0.028(2) 0.049(3) 0.034(3) -0.001(2) -0.003(2) 0.002(2) C36 0.056(4) 0.067(4) 0.066(4) -0.005(4) -0.012(3) -0.018(4) C37 0.074(5) 0.044(3) 0.105(6) 0.015(4) -0.013(5) -0.013(4) C38 0.031(3) 0.054(3) 0.056(4) 0.003(3) 0.001(3) -0.004(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 1.446(7) . ? O1 H1 0.82(2) . ? O2 C7 1.399(7) . ? O2 C16 1.448(6) . ? O3 C15 1.370(7) . ? O3 C6 1.478(8) . ? O4 C15 1.184(8) . ? O5 C7 1.411(7) . ? O5 H5A 0.82(2) . ? O6 C14 1.427(7) . ? O6 H6 0.84(2) . ? O7 C19 1.204(8) . ? O8 C19 1.321(8) . ? O8 H8 0.83(2) . ? O9 C20 1.439(7) . ? O9 H9A 0.82(2) . ? O10 C26 1.407(6) . ? O10 C35 1.444(6) . ? O11 C34 1.359(7) . ? O11 C25 1.466(7) . ? O12 C34 1.182(7) . ? O13 C26 1.402(6) . ? O13 H13A 0.81(2) . ? O14 C33 1.428(7) . ? O14 H14 0.83(2) . ? O15 C38 1.218(7) . ? O16 C38 1.322(8) . ? O16 H16 0.83(2) . ? O17 C39 1.483(19) . ? O17 H17 0.8200 . ? C1 C2 1.526(8) . ? C1 C10 1.547(7) . ? C1 H1A 0.9800 . ? C2 C3 1.507(9) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.542(9) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C18 1.527(9) . ? C4 C17 1.543(9) . ? C4 C5 1.547(8) . ? C5 C6 1.528(8) . ? C5 C10 1.580(7) . ? C5 H5 0.9800 . ? C6 C7 1.524(9) . ? C6 H6A 0.9800 . ? C7 C8 1.534(7) . ? C8 C15 1.520(8) . ? C8 C14 1.545(8) . ? C8 C9 1.573(7) . ? C9 C11 1.531(7) . ? C9 C10 1.565(7) . ? C9 H9 0.9800 . ? C10 C16 1.514(7) . ? C11 C12 1.524(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.543(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C19 1.513(8) . ? C13 C14 1.544(8) . ? C13 H13 0.9800 . ? C14 H14A 0.9800 . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C20 C21 1.509(8) . ? C20 C29 1.537(7) . ? C20 H20 0.9800 . ? C21 C22 1.515(9) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.532(9) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.541(8) . ? C23 C36 1.553(9) . ? C23 C37 1.556(9) . ? C24 C25 1.534(8) . ? C24 C29 1.573(7) . ? C24 H24 0.9800 . ? C25 C26 1.536(8) . ? C25 H25 0.9800 . ? C26 C27 1.537(7) . ? C27 C34 1.530(8) . ? C27 C33 1.532(8) . ? C27 C28 1.585(7) . ? C28 C30 1.514(8) . ? C28 C29 1.561(7) . ? C28 H28 0.9800 . ? C29 C35 1.529(7) . ? C30 C31 1.515(8) . ? C30 H30A 0.9700 . ? C30 H30B 0.9700 . ? C31 C32 1.544(9) . ? C31 H31A 0.9700 . ? C31 H31B 0.9700 . ? C32 C38 1.522(8) . ? C32 C33 1.533(8) . ? C32 H32 0.9800 . ? C33 H33 0.9800 . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? C39 H39A 0.9600 . ? C39 H39B 0.9600 . ? C39 H39C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 111(5) . . ? C7 O2 C16 114.4(4) . . ? C15 O3 C6 109.0(4) . . ? C7 O5 H5A 161(6) . . ? C14 O6 H6 116(8) . . ? C19 O8 H8 96(7) . . ? C20 O9 H9A 97(6) . . ? C26 O10 C35 113.7(4) . . ? C34 O11 C25 110.0(4) . . ? C26 O13 H13A 110(5) . . ? C33 O14 H14 104(7) . . ? C38 O16 H16 117(5) . . ? C39 O17 H17 109.5 . . ? O1 C1 C2 110.3(4) . . ? O1 C1 C10 111.9(4) . . ? C2 C1 C10 112.1(4) . . ? O1 C1 H1A 107.4 . . ? C2 C1 H1A 107.4 . . ? C10 C1 H1A 107.4 . . ? C3 C2 C1 113.2(5) . . ? C3 C2 H2A 108.9 . . ? C1 C2 H2A 108.9 . . ? C3 C2 H2B 108.9 . . ? C1 C2 H2B 108.9 . . ? H2A C2 H2B 107.7 . . ? C2 C3 C4 113.2(5) . . ? C2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? C2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C18 C4 C3 107.8(6) . . ? C18 C4 C17 108.7(5) . . ? C3 C4 C17 111.2(6) . . ? C18 C4 C5 107.4(5) . . ? C3 C4 C5 106.4(5) . . ? C17 C4 C5 115.1(5) . . ? C6 C5 C4 114.6(5) . . ? C6 C5 C10 107.7(5) . . ? C4 C5 C10 118.4(5) . . ? C6 C5 H5 104.9 . . ? C4 C5 H5 104.9 . . ? C10 C5 H5 104.9 . . ? O3 C6 C7 101.5(5) . . ? O3 C6 C5 109.6(5) . . ? C7 C6 C5 110.8(5) . . ? O3 C6 H6A 111.5 . . ? C7 C6 H6A 111.5 . . ? C5 C6 H6A 111.5 . . ? O2 C7 O5 105.7(5) . . ? O2 C7 C6 113.5(5) . . ? O5 C7 C6 112.9(5) . . ? O2 C7 C8 115.3(4) . . ? O5 C7 C8 110.5(5) . . ? C6 C7 C8 99.2(5) . . ? C15 C8 C7 100.5(5) . . ? C15 C8 C14 114.4(4) . . ? C7 C8 C14 113.4(5) . . ? C15 C8 C9 107.4(4) . . ? C7 C8 C9 108.0(4) . . ? C14 C8 C9 112.2(4) . . ? C11 C9 C10 117.4(4) . . ? C11 C9 C8 111.2(4) . . ? C10 C9 C8 108.8(4) . . ? C11 C9 H9 106.2 . . ? C10 C9 H9 106.2 . . ? C8 C9 H9 106.2 . . ? C16 C10 C1 111.3(4) . . ? C16 C10 C9 107.4(4) . . ? C1 C10 C9 112.6(4) . . ? C16 C10 C5 110.9(4) . . ? C1 C10 C5 109.2(4) . . ? C9 C10 C5 105.4(4) . . ? C12 C11 C9 110.0(4) . . ? C12 C11 H11A 109.7 . . ? C9 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C9 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C11 C12 C13 113.3(5) . . ? C11 C12 H12A 108.9 . . ? C13 C12 H12A 108.9 . . ? C11 C12 H12B 108.9 . . ? C13 C12 H12B 108.9 . . ? H12A C12 H12B 107.7 . . ? C19 C13 C12 111.8(5) . . ? C19 C13 C14 117.9(5) . . ? C12 C13 C14 111.1(4) . . ? C19 C13 H13 104.9 . . ? C12 C13 H13 104.9 . . ? C14 C13 H13 104.9 . . ? O6 C14 C13 109.0(5) . . ? O6 C14 C8 113.5(4) . . ? C13 C14 C8 114.4(5) . . ? O6 C14 H14A 106.5 . . ? C13 C14 H14A 106.5 . . ? C8 C14 H14A 106.5 . . ? O4 C15 O3 121.7(6) . . ? O4 C15 C8 130.1(6) . . ? O3 C15 C8 108.2(5) . . ? O2 C16 C10 110.3(4) . . ? O2 C16 H16A 109.6 . . ? C10 C16 H16A 109.6 . . ? O2 C16 H16B 109.6 . . ? C10 C16 H16B 109.6 . . ? H16A C16 H16B 108.1 . . ? C4 C17 H17A 109.5 . . ? C4 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C4 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O7 C19 O8 119.6(6) . . ? O7 C19 C13 122.6(6) . . ? O8 C19 C13 117.4(6) . . ? O9 C20 C21 107.8(4) . . ? O9 C20 C29 111.2(4) . . ? C21 C20 C29 112.7(4) . . ? O9 C20 H20 108.3 . . ? C21 C20 H20 108.3 . . ? C29 C20 H20 108.3 . . ? C20 C21 C22 112.9(5) . . ? C20 C21 H21A 109.0 . . ? C22 C21 H21A 109.0 . . ? C20 C21 H21B 109.0 . . ? C22 C21 H21B 109.0 . . ? H21A C21 H21B 107.8 . . ? C21 C22 C23 113.1(5) . . ? C21 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? C21 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? C22 C23 C24 107.0(5) . . ? C22 C23 C36 111.4(5) . . ? C24 C23 C36 114.5(5) . . ? C22 C23 C37 108.4(6) . . ? C24 C23 C37 107.4(5) . . ? C36 C23 C37 107.9(6) . . ? C25 C24 C23 115.7(5) . . ? C25 C24 C29 107.9(4) . . ? C23 C24 C29 117.0(4) . . ? C25 C24 H24 105.0 . . ? C23 C24 H24 105.0 . . ? C29 C24 H24 105.0 . . ? O11 C25 C24 110.4(4) . . ? O11 C25 C26 102.0(4) . . ? C24 C25 C26 110.3(4) . . ? O11 C25 H25 111.3 . . ? C24 C25 H25 111.3 . . ? C26 C25 H25 111.3 . . ? O13 C26 O10 106.6(4) . . ? O13 C26 C25 108.3(5) . . ? O10 C26 C25 112.8(4) . . ? O13 C26 C27 114.1(4) . . ? O10 C26 C27 115.6(4) . . ? C25 C26 C27 99.2(4) . . ? C34 C27 C33 117.0(4) . . ? C34 C27 C26 99.1(4) . . ? C33 C27 C26 113.3(4) . . ? C34 C27 C28 105.8(4) . . ? C33 C27 C28 112.6(4) . . ? C26 C27 C28 107.9(4) . . ? C30 C28 C29 117.9(4) . . ? C30 C28 C27 111.0(4) . . ? C29 C28 C27 109.1(4) . . ? C30 C28 H28 106.0 . . ? C29 C28 H28 106.0 . . ? C27 C28 H28 106.0 . . ? C35 C29 C20 111.6(4) . . ? C35 C29 C28 105.9(4) . . ? C20 C29 C28 113.3(4) . . ? C35 C29 C24 111.7(4) . . ? C20 C29 C24 109.0(4) . . ? C28 C29 C24 105.2(4) . . ? C28 C30 C31 110.4(5) . . ? C28 C30 H30A 109.6 . . ? C31 C30 H30A 109.6 . . ? C28 C30 H30B 109.6 . . ? C31 C30 H30B 109.6 . . ? H30A C30 H30B 108.1 . . ? C30 C31 C32 112.4(5) . . ? C30 C31 H31A 109.1 . . ? C32 C31 H31A 109.1 . . ? C30 C31 H31B 109.1 . . ? C32 C31 H31B 109.1 . . ? H31A C31 H31B 107.8 . . ? C38 C32 C33 114.6(5) . . ? C38 C32 C31 113.4(5) . . ? C33 C32 C31 111.1(5) . . ? C38 C32 H32 105.6 . . ? C33 C32 H32 105.6 . . ? C31 C32 H32 105.6 . . ? O14 C33 C27 110.6(5) . . ? O14 C33 C32 113.8(5) . . ? C27 C33 C32 115.3(4) . . ? O14 C33 H33 105.3 . . ? C27 C33 H33 105.3 . . ? C32 C33 H33 105.3 . . ? O12 C34 O11 122.4(6) . . ? O12 C34 C27 129.3(6) . . ? O11 C34 C27 108.1(4) . . ? O10 C35 C29 110.3(4) . . ? O10 C35 H35A 109.6 . . ? C29 C35 H35A 109.6 . . ? O10 C35 H35B 109.6 . . ? C29 C35 H35B 109.6 . . ? H35A C35 H35B 108.1 . . ? C23 C36 H36A 109.5 . . ? C23 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C23 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? C23 C37 H37A 109.5 . . ? C23 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C23 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? O15 C38 O16 122.4(5) . . ? O15 C38 C32 124.2(6) . . ? O16 C38 C32 113.3(5) . . ? O17 C39 H39A 109.5 . . ? O17 C39 H39B 109.5 . . ? H39A C39 H39B 109.5 . . ? O17 C39 H39C 109.5 . . ? H39A C39 H39C 109.5 . . ? H39B C39 H39C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -179.2(5) . . . . ? C10 C1 C2 C3 55.4(7) . . . . ? C1 C2 C3 C4 -59.8(8) . . . . ? C2 C3 C4 C18 169.2(6) . . . . ? C2 C3 C4 C17 -71.8(7) . . . . ? C2 C3 C4 C5 54.2(7) . . . . ? C18 C4 C5 C6 64.8(7) . . . . ? C3 C4 C5 C6 -179.9(5) . . . . ? C17 C4 C5 C6 -56.3(7) . . . . ? C18 C4 C5 C10 -166.2(5) . . . . ? C3 C4 C5 C10 -51.0(7) . . . . ? C17 C4 C5 C10 72.6(7) . . . . ? C15 O3 C6 C7 29.9(6) . . . . ? C15 O3 C6 C5 -87.3(6) . . . . ? C4 C5 C6 O3 -122.3(5) . . . . ? C10 C5 C6 O3 103.6(5) . . . . ? C4 C5 C6 C7 126.6(5) . . . . ? C10 C5 C6 C7 -7.5(6) . . . . ? C16 O2 C7 O5 -176.0(5) . . . . ? C16 O2 C7 C6 59.8(6) . . . . ? C16 O2 C7 C8 -53.6(6) . . . . ? O3 C6 C7 O2 -166.9(5) . . . . ? C5 C6 C7 O2 -50.6(6) . . . . ? O3 C6 C7 O5 72.8(6) . . . . ? C5 C6 C7 O5 -170.9(5) . . . . ? O3 C6 C7 C8 -44.1(5) . . . . ? C5 C6 C7 C8 72.2(5) . . . . ? O2 C7 C8 C15 163.7(5) . . . . ? O5 C7 C8 C15 -76.5(6) . . . . ? C6 C7 C8 C15 42.2(5) . . . . ? O2 C7 C8 C14 -73.7(6) . . . . ? O5 C7 C8 C14 46.0(6) . . . . ? C6 C7 C8 C14 164.8(4) . . . . ? O2 C7 C8 C9 51.4(6) . . . . ? O5 C7 C8 C9 171.1(5) . . . . ? C6 C7 C8 C9 -70.2(5) . . . . ? C15 C8 C9 C11 127.9(5) . . . . ? C7 C8 C9 C11 -124.5(5) . . . . ? C14 C8 C9 C11 1.3(6) . . . . ? C15 C8 C9 C10 -101.3(5) . . . . ? C7 C8 C9 C10 6.3(6) . . . . ? C14 C8 C9 C10 132.1(4) . . . . ? O1 C1 C10 C16 -49.3(6) . . . . ? C2 C1 C10 C16 75.3(6) . . . . ? O1 C1 C10 C9 71.3(5) . . . . ? C2 C1 C10 C9 -164.1(5) . . . . ? O1 C1 C10 C5 -172.0(4) . . . . ? C2 C1 C10 C5 -47.5(6) . . . . ? C11 C9 C10 C16 67.4(6) . . . . ? C8 C9 C10 C16 -60.0(5) . . . . ? C11 C9 C10 C1 -55.5(6) . . . . ? C8 C9 C10 C1 177.2(4) . . . . ? C11 C9 C10 C5 -174.4(5) . . . . ? C8 C9 C10 C5 58.3(5) . . . . ? C6 C5 C10 C16 58.1(6) . . . . ? C4 C5 C10 C16 -74.0(6) . . . . ? C6 C5 C10 C1 -178.9(4) . . . . ? C4 C5 C10 C1 49.0(6) . . . . ? C6 C5 C10 C9 -57.8(5) . . . . ? C4 C5 C10 C9 170.1(5) . . . . ? C10 C9 C11 C12 178.7(5) . . . . ? C8 C9 C11 C12 -55.1(6) . . . . ? C9 C11 C12 C13 61.1(7) . . . . ? C11 C12 C13 C19 -144.0(5) . . . . ? C11 C12 C13 C14 -10.1(7) . . . . ? C19 C13 C14 O6 -42.3(7) . . . . ? C12 C13 C14 O6 -173.1(5) . . . . ? C19 C13 C14 C8 85.9(6) . . . . ? C12 C13 C14 C8 -44.9(6) . . . . ? C15 C8 C14 O6 52.9(6) . . . . ? C7 C8 C14 O6 -61.6(6) . . . . ? C9 C8 C14 O6 175.6(4) . . . . ? C15 C8 C14 C13 -73.0(6) . . . . ? C7 C8 C14 C13 172.6(4) . . . . ? C9 C8 C14 C13 49.8(6) . . . . ? C6 O3 C15 O4 176.7(6) . . . . ? C6 O3 C15 C8 -2.3(6) . . . . ? C7 C8 C15 O4 155.2(7) . . . . ? C14 C8 C15 O4 33.3(9) . . . . ? C9 C8 C15 O4 -91.9(7) . . . . ? C7 C8 C15 O3 -25.9(6) . . . . ? C14 C8 C15 O3 -147.8(5) . . . . ? C9 C8 C15 O3 86.9(5) . . . . ? C7 O2 C16 C10 -5.7(6) . . . . ? C1 C10 C16 O2 -174.5(4) . . . . ? C9 C10 C16 O2 61.9(5) . . . . ? C5 C10 C16 O2 -52.7(6) . . . . ? C12 C13 C19 O7 -17.2(8) . . . . ? C14 C13 C19 O7 -147.7(6) . . . . ? C12 C13 C19 O8 170.0(5) . . . . ? C14 C13 C19 O8 39.5(8) . . . . ? O9 C20 C21 C22 177.9(5) . . . . ? C29 C20 C21 C22 54.9(7) . . . . ? C20 C21 C22 C23 -58.3(7) . . . . ? C21 C22 C23 C24 54.5(6) . . . . ? C21 C22 C23 C36 -71.4(7) . . . . ? C21 C22 C23 C37 170.0(5) . . . . ? C22 C23 C24 C25 178.5(5) . . . . ? C36 C23 C24 C25 -57.5(7) . . . . ? C37 C23 C24 C25 62.3(7) . . . . ? C22 C23 C24 C29 -52.8(6) . . . . ? C36 C23 C24 C29 71.2(7) . . . . ? C37 C23 C24 C29 -168.9(6) . . . . ? C34 O11 C25 C24 -93.0(5) . . . . ? C34 O11 C25 C26 24.2(5) . . . . ? C23 C24 C25 O11 -127.5(5) . . . . ? C29 C24 C25 O11 99.4(5) . . . . ? C23 C24 C25 C26 120.6(5) . . . . ? C29 C24 C25 C26 -12.5(6) . . . . ? C35 O10 C26 O13 -176.0(4) . . . . ? C35 O10 C26 C25 65.2(6) . . . . ? C35 O10 C26 C27 -47.9(6) . . . . ? O11 C25 C26 O13 77.2(5) . . . . ? C24 C25 C26 O13 -165.5(4) . . . . ? O11 C25 C26 O10 -165.0(4) . . . . ? C24 C25 C26 O10 -47.7(6) . . . . ? O11 C25 C26 C27 -42.1(5) . . . . ? C24 C25 C26 C27 75.1(5) . . . . ? O13 C26 C27 C34 -71.3(5) . . . . ? O10 C26 C27 C34 164.4(4) . . . . ? C25 C26 C27 C34 43.5(5) . . . . ? O13 C26 C27 C33 53.4(6) . . . . ? O10 C26 C27 C33 -70.9(6) . . . . ? C25 C26 C27 C33 168.2(4) . . . . ? O13 C26 C27 C28 178.7(4) . . . . ? O10 C26 C27 C28 54.4(6) . . . . ? C25 C26 C27 C28 -66.5(5) . . . . ? C34 C27 C28 C30 124.1(5) . . . . ? C33 C27 C28 C30 -4.9(6) . . . . ? C26 C27 C28 C30 -130.6(5) . . . . ? C34 C27 C28 C29 -104.4(5) . . . . ? C33 C27 C28 C29 126.6(4) . . . . ? C26 C27 C28 C29 0.9(5) . . . . ? O9 C20 C29 C35 -46.4(6) . . . . ? C21 C20 C29 C35 74.8(6) . . . . ? O9 C20 C29 C28 73.0(5) . . . . ? C21 C20 C29 C28 -165.8(4) . . . . ? O9 C20 C29 C24 -170.3(4) . . . . ? C21 C20 C29 C24 -49.1(6) . . . . ? C30 C28 C29 C35 70.9(6) . . . . ? C27 C28 C29 C35 -56.8(5) . . . . ? C30 C28 C29 C20 -51.7(6) . . . . ? C27 C28 C29 C20 -179.5(4) . . . . ? C30 C28 C29 C24 -170.7(5) . . . . ? C27 C28 C29 C24 61.6(5) . . . . ? C25 C24 C29 C35 59.4(6) . . . . ? C23 C24 C29 C35 -72.9(6) . . . . ? C25 C24 C29 C20 -176.8(4) . . . . ? C23 C24 C29 C20 50.8(6) . . . . ? C25 C24 C29 C28 -55.0(5) . . . . ? C23 C24 C29 C28 172.6(4) . . . . ? C29 C28 C30 C31 -177.8(5) . . . . ? C27 C28 C30 C31 -50.9(6) . . . . ? C28 C30 C31 C32 65.8(7) . . . . ? C30 C31 C32 C38 -150.1(5) . . . . ? C30 C31 C32 C33 -19.3(7) . . . . ? C34 C27 C33 O14 58.9(6) . . . . ? C26 C27 C33 O14 -55.5(6) . . . . ? C28 C27 C33 O14 -178.2(4) . . . . ? C34 C27 C33 C32 -72.0(6) . . . . ? C26 C27 C33 C32 173.6(4) . . . . ? C28 C27 C33 C32 50.8(6) . . . . ? C38 C32 C33 O14 -36.8(7) . . . . ? C31 C32 C33 O14 -167.0(5) . . . . ? C38 C32 C33 C27 92.6(6) . . . . ? C31 C32 C33 C27 -37.6(6) . . . . ? C25 O11 C34 O12 -179.3(5) . . . . ? C25 O11 C34 C27 4.7(6) . . . . ? C33 C27 C34 O12 31.0(8) . . . . ? C26 C27 C34 O12 153.0(6) . . . . ? C28 C27 C34 O12 -95.3(7) . . . . ? C33 C27 C34 O11 -153.4(4) . . . . ? C26 C27 C34 O11 -31.3(5) . . . . ? C28 C27 C34 O11 80.3(5) . . . . ? C26 O10 C35 C29 -15.0(6) . . . . ? C20 C29 C35 O10 -168.7(4) . . . . ? C28 C29 C35 O10 67.7(5) . . . . ? C24 C29 C35 O10 -46.4(6) . . . . ? C33 C32 C38 O15 31.2(9) . . . . ? C31 C32 C38 O15 160.3(6) . . . . ? C33 C32 C38 O16 -151.7(5) . . . . ? C31 C32 C38 O16 -22.6(7) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O16 H16 O9 0.83(2) 1.88(3) 2.683(5) 161(7) 1_655 O14 H14 O15 0.83(2) 1.84(5) 2.618(7) 155(10) . O13 H13A O14 0.81(2) 1.90(4) 2.627(7) 148(7) . O9 H9A O1 0.82(2) 1.98(3) 2.778(5) 166(9) 4_467 O8 H8 O6 0.83(2) 1.76(4) 2.559(8) 163(10) . O6 H6 O5 0.84(2) 1.98(8) 2.631(7) 134(9) . O5 H5A O13 0.82(2) 2.62(12) 2.945(7) 105(10) 3_646 O5 H5A O17 0.82(2) 2.51(8) 2.933(12) 113(7) . O1 H1 O7 0.82(2) 2.02(3) 2.825(5) 167(7) 1_655 O17 H17 O5 0.82 2.34 2.933(12) 129.9 . _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.572 _refine_diff_density_min -0.427 _refine_diff_density_rms 0.073 # Attachment '- Compound 6.cif' data_cd201649 _database_code_depnum_ccdc_archive 'CCDC 822519' #TrackingRef '- Compound 6.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 O7' _chemical_formula_weight 380.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 '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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.3751(10) _cell_length_b 7.7786(7) _cell_length_c 11.4085(11) _cell_angle_alpha 90.00 _cell_angle_beta 99.955(2) _cell_angle_gamma 90.00 _cell_volume 906.85(15) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3063 _cell_measurement_theta_min 5.834 _cell_measurement_theta_max 56.054 _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.358 _exptl_crystal_size_mid 0.269 _exptl_crystal_size_min 0.078 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.393 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.105 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.4578 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4941 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0345 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.99 _reflns_number_total 3069 _reflns_number_gt 2975 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0485P)^2^+0.1634P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef ? _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.7(9) _chemical_absolute_configuration ad _refine_ls_number_reflns 3069 _refine_ls_number_parameters 251 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0375 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0918 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _refine_ls_shift/su_max 0.005 _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 -0.14721(14) 0.60547(19) 0.13034(12) 0.0376(3) Uani 1 1 d . . . H1 H -0.1392 0.5924 0.0606 0.056 Uiso 1 1 calc R . . O2 O 0.05440(11) 0.13783(18) 0.09038(10) 0.0295(3) Uani 1 1 d . . . O3 O 0.16655(13) -0.07209(19) 0.19901(12) 0.0354(3) Uani 1 1 d . . . H3 H 0.2413 -0.0401 0.2252 0.053 Uiso 1 1 calc R . . O4 O 0.00245(13) -0.03227(18) 0.37284(11) 0.0351(3) Uani 1 1 d . . . O5 O 0.16222(15) 0.0712(2) 0.51108(12) 0.0472(4) Uani 1 1 d . . . O6 O 0.35824(13) 0.1257(2) 0.31500(14) 0.0456(4) Uani 1 1 d . . . H6 H 0.3702 0.0799 0.3807 0.068 Uiso 1 1 calc R . . O7 O 0.52431(19) 0.4362(3) 0.4944(2) 0.0880(8) Uani 1 1 d . . . C1 C -0.19557(18) 0.4503(3) 0.17395(16) 0.0310(4) Uani 1 1 d . . . H1A H -0.2186 0.4766 0.2518 0.037 Uiso 1 1 calc R . . C2 C -0.32102(19) 0.3929(3) 0.09274(19) 0.0384(5) Uani 1 1 d . . . H2A H -0.3853 0.4844 0.0876 0.046 Uiso 1 1 calc R . . H2B H -0.3024 0.3730 0.0134 0.046 Uiso 1 1 calc R . . C3 C -0.37823(18) 0.2307(3) 0.1364(2) 0.0391(5) Uani 1 1 d . . . H3A H -0.4578 0.2016 0.0820 0.047 Uiso 1 1 calc R . . H3B H -0.4016 0.2531 0.2137 0.047 Uiso 1 1 calc R . . C4 C -0.28439(17) 0.0748(3) 0.14708(16) 0.0314(4) Uani 1 1 d . . . C5 C -0.15344(16) 0.1340(2) 0.22526(15) 0.0263(4) Uani 1 1 d . . . H5 H -0.1754 0.1532 0.3044 0.032 Uiso 1 1 calc R . . C6 C -0.04460(17) -0.0049(3) 0.24477(16) 0.0284(4) Uani 1 1 d . . . H6A H -0.0742 -0.1126 0.2043 0.034 Uiso 1 1 calc R . . C7 C 0.07948(17) 0.0630(2) 0.20503(15) 0.0262(4) Uani 1 1 d . . . C8 C 0.12488(17) 0.1913(2) 0.30790(14) 0.0256(4) Uani 1 1 d . . . C9 C 0.02025(17) 0.3427(2) 0.30069(15) 0.0260(4) Uani 1 1 d . . . H9 H -0.0193 0.3332 0.3725 0.031 Uiso 1 1 calc R . . C10 C -0.09129(17) 0.3066(2) 0.19353(15) 0.0252(4) Uani 1 1 d . . . C11 C 0.08650(19) 0.5205(3) 0.30634(18) 0.0351(5) Uani 1 1 d . . . H11A H 0.1216 0.5402 0.2340 0.042 Uiso 1 1 calc R . . H11B H 0.0224 0.6094 0.3125 0.042 Uiso 1 1 calc R . . C12 C 0.1969(2) 0.5297(3) 0.4140(2) 0.0464(6) Uani 1 1 d . . . H12A H 0.1595 0.5204 0.4859 0.056 Uiso 1 1 calc R . . H12B H 0.2389 0.6412 0.4148 0.056 Uiso 1 1 calc R . . C13 C 0.3026(2) 0.3874(3) 0.41545(17) 0.0377(5) Uani 1 1 d . . . H13 H 0.3075 0.3231 0.4900 0.045 Uiso 1 1 calc R . . C14 C 0.26451(17) 0.2604(3) 0.31239(15) 0.0303(4) Uani 1 1 d . . . H14 H 0.2646 0.3248 0.2386 0.036 Uiso 1 1 calc R . . C15 C 0.4362(2) 0.4640(3) 0.41338(19) 0.0449(5) Uani 1 1 d . . . C16 C 0.10479(18) 0.0740(3) 0.41068(16) 0.0313(4) Uani 1 1 d . . . C17 C 0.4561(3) 0.5780(4) 0.3129(2) 0.0640(7) Uani 1 1 d . . . H17A H 0.4431 0.6956 0.3336 0.096 Uiso 1 1 calc R . . H17B H 0.3946 0.5480 0.2430 0.096 Uiso 1 1 calc R . . H17C H 0.5436 0.5637 0.2975 0.096 Uiso 1 1 calc R . . C18 C -0.2700(2) 0.0072(3) 0.02314(18) 0.0402(5) Uani 1 1 d . . . H18A H -0.3530 -0.0350 -0.0170 0.060 Uiso 1 1 calc R . . H18B H -0.2070 -0.0843 0.0316 0.060 Uiso 1 1 calc R . . H18C H -0.2412 0.0988 -0.0225 0.060 Uiso 1 1 calc R . . C19 C -0.3438(2) -0.0698(3) 0.2130(2) 0.0444(5) Uani 1 1 d . . . H19A H -0.3541 -0.0301 0.2905 0.067 Uiso 1 1 calc R . . H19B H -0.2866 -0.1677 0.2210 0.067 Uiso 1 1 calc R . . H19C H -0.4276 -0.1016 0.1686 0.067 Uiso 1 1 calc R . . C20 C -0.02710(17) 0.2893(2) 0.08243(15) 0.0267(4) Uani 1 1 d . . . H20A H -0.0945 0.2819 0.0121 0.032 Uiso 1 1 calc R . . H20B H 0.0256 0.3904 0.0748 0.032 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 0.0511(8) 0.0243(8) 0.0388(7) 0.0044(6) 0.0120(6) 0.0045(7) O2 0.0345(6) 0.0318(7) 0.0226(6) -0.0022(5) 0.0061(5) 0.0069(6) O3 0.0317(6) 0.0316(8) 0.0411(7) -0.0054(6) 0.0014(6) 0.0086(6) O4 0.0367(7) 0.0341(9) 0.0338(7) 0.0115(6) 0.0040(5) -0.0020(6) O5 0.0516(9) 0.0594(11) 0.0280(7) 0.0117(7) -0.0008(6) -0.0032(8) O6 0.0281(6) 0.0506(10) 0.0563(9) -0.0038(8) 0.0026(6) 0.0048(7) O7 0.0568(11) 0.0964(19) 0.0948(14) 0.0080(14) -0.0323(11) -0.0275(12) C1 0.0346(9) 0.0287(11) 0.0316(9) 0.0014(8) 0.0110(7) 0.0040(8) C2 0.0325(9) 0.0408(13) 0.0410(10) 0.0051(9) 0.0037(8) 0.0126(9) C3 0.0253(9) 0.0421(13) 0.0496(11) -0.0002(10) 0.0059(8) 0.0023(9) C4 0.0238(8) 0.0335(11) 0.0365(9) 0.0009(8) 0.0040(7) -0.0011(8) C5 0.0268(8) 0.0257(10) 0.0274(8) 0.0005(7) 0.0073(6) -0.0010(8) C6 0.0300(8) 0.0240(10) 0.0300(8) 0.0025(7) 0.0022(7) 0.0008(8) C7 0.0278(8) 0.0229(9) 0.0276(8) -0.0010(7) 0.0038(7) 0.0028(7) C8 0.0266(8) 0.0288(10) 0.0212(8) 0.0002(7) 0.0036(7) 0.0014(7) C9 0.0290(9) 0.0250(9) 0.0256(8) -0.0019(7) 0.0089(7) -0.0010(7) C10 0.0273(8) 0.0232(10) 0.0260(8) 0.0007(7) 0.0068(7) 0.0009(7) C11 0.0372(10) 0.0279(11) 0.0405(10) -0.0063(8) 0.0074(8) -0.0008(8) C12 0.0411(11) 0.0515(15) 0.0476(12) -0.0246(11) 0.0107(9) -0.0091(10) C13 0.0392(11) 0.0456(14) 0.0269(9) -0.0025(8) 0.0021(8) -0.0096(10) C14 0.0269(8) 0.0360(11) 0.0275(8) 0.0000(8) 0.0029(7) -0.0021(8) C15 0.0389(11) 0.0454(14) 0.0481(11) -0.0131(10) 0.0013(9) -0.0095(10) C16 0.0326(9) 0.0330(11) 0.0287(9) 0.0039(8) 0.0067(7) 0.0049(8) C17 0.0683(16) 0.0624(19) 0.0670(16) -0.0073(14) 0.0272(13) -0.0257(15) C18 0.0344(10) 0.0450(13) 0.0388(10) -0.0058(9) -0.0005(8) -0.0025(9) C19 0.0333(10) 0.0409(13) 0.0604(13) 0.0034(11) 0.0116(9) -0.0079(10) C20 0.0293(8) 0.0248(10) 0.0262(8) 0.0021(7) 0.0051(7) 0.0017(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 O1 C1 1.429(2) . ? O1 H1 0.8200 . ? O2 C7 1.414(2) . ? O2 C20 1.444(2) . ? O3 C7 1.395(2) . ? O3 H3 0.8200 . ? O4 C16 1.356(2) . ? O4 C6 1.474(2) . ? O5 C16 1.196(2) . ? O6 C14 1.426(2) . ? O6 H6 0.8200 . ? O7 C15 1.202(3) . ? C1 C2 1.528(3) . ? C1 C10 1.545(2) . ? C1 H1A 0.9800 . ? C2 C3 1.515(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.546(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C19 1.539(3) . ? C4 C18 1.540(3) . ? C4 C5 1.560(2) . ? C5 C6 1.551(2) . ? C5 C10 1.559(3) . ? C5 H5 0.9800 . ? C6 C7 1.531(2) . ? C6 H6A 0.9800 . ? C7 C8 1.550(2) . ? C8 C16 1.528(2) . ? C8 C14 1.538(2) . ? C8 C9 1.594(2) . ? C9 C11 1.541(3) . ? C9 C10 1.557(2) . ? C9 H9 0.9800 . ? C10 C20 1.536(2) . ? C11 C12 1.529(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.555(3) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C15 1.513(3) . ? C13 C14 1.534(3) . ? C13 H13 0.9800 . ? C14 H14 0.9800 . ? C15 C17 1.492(4) . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 H1 109.5 . . ? C7 O2 C20 113.95(12) . . ? C7 O3 H3 109.5 . . ? C16 O4 C6 109.54(13) . . ? C14 O6 H6 109.5 . . ? O1 C1 C2 110.45(16) . . ? O1 C1 C10 112.47(14) . . ? C2 C1 C10 112.21(16) . . ? O1 C1 H1A 107.1 . . ? C2 C1 H1A 107.1 . . ? C10 C1 H1A 107.1 . . ? C3 C2 C1 112.66(17) . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C4 113.69(15) . . ? C2 C3 H3A 108.8 . . ? C4 C3 H3A 108.8 . . ? C2 C3 H3B 108.8 . . ? C4 C3 H3B 108.8 . . ? H3A C3 H3B 107.7 . . ? C19 C4 C18 108.03(18) . . ? C19 C4 C3 108.15(15) . . ? C18 C4 C3 110.78(17) . . ? C19 C4 C5 108.59(16) . . ? C18 C4 C5 114.38(14) . . ? C3 C4 C5 106.74(16) . . ? C6 C5 C10 108.25(13) . . ? C6 C5 C4 114.66(16) . . ? C10 C5 C4 118.39(15) . . ? C6 C5 H5 104.7 . . ? C10 C5 H5 104.7 . . ? C4 C5 H5 104.7 . . ? O4 C6 C7 101.08(13) . . ? O4 C6 C5 110.56(14) . . ? C7 C6 C5 110.23(15) . . ? O4 C6 H6A 111.5 . . ? C7 C6 H6A 111.5 . . ? C5 C6 H6A 111.5 . . ? O3 C7 O2 106.36(13) . . ? O3 C7 C6 109.83(15) . . ? O2 C7 C6 112.72(13) . . ? O3 C7 C8 114.04(14) . . ? O2 C7 C8 114.75(15) . . ? C6 C7 C8 99.15(13) . . ? C16 C8 C14 115.84(14) . . ? C16 C8 C7 97.63(15) . . ? C14 C8 C7 114.29(14) . . ? C16 C8 C9 107.37(13) . . ? C14 C8 C9 111.89(16) . . ? C7 C8 C9 108.74(13) . . ? C11 C9 C10 117.40(15) . . ? C11 C9 C8 111.48(14) . . ? C10 C9 C8 108.34(14) . . ? C11 C9 H9 106.3 . . ? C10 C9 H9 106.3 . . ? C8 C9 H9 106.3 . . ? C20 C10 C1 109.69(14) . . ? C20 C10 C9 107.12(14) . . ? C1 C10 C9 112.97(14) . . ? C20 C10 C5 111.82(15) . . ? C1 C10 C5 110.45(13) . . ? C9 C10 C5 104.71(14) . . ? C12 C11 C9 110.01(18) . . ? C12 C11 H11A 109.7 . . ? C9 C11 H11A 109.7 . . ? C12 C11 H11B 109.7 . . ? C9 C11 H11B 109.7 . . ? H11A C11 H11B 108.2 . . ? C11 C12 C13 113.85(16) . . ? C11 C12 H12A 108.8 . . ? C13 C12 H12A 108.8 . . ? C11 C12 H12B 108.8 . . ? C13 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? C15 C13 C14 110.88(16) . . ? C15 C13 C12 111.44(19) . . ? C14 C13 C12 111.25(15) . . ? C15 C13 H13 107.7 . . ? C14 C13 H13 107.7 . . ? C12 C13 H13 107.7 . . ? O6 C14 C13 111.90(15) . . ? O6 C14 C8 112.27(16) . . ? C13 C14 C8 111.51(15) . . ? O6 C14 H14 106.9 . . ? C13 C14 H14 106.9 . . ? C8 C14 H14 106.9 . . ? O7 C15 C17 120.6(2) . . ? O7 C15 C13 119.6(2) . . ? C17 C15 C13 119.69(19) . . ? O5 C16 O4 121.78(18) . . ? O5 C16 C8 129.35(19) . . ? O4 C16 C8 108.83(14) . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C4 C18 H18A 109.5 . . ? C4 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C4 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C4 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C4 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O2 C20 C10 110.64(14) . . ? O2 C20 H20A 109.5 . . ? C10 C20 H20A 109.5 . . ? O2 C20 H20B 109.5 . . ? C10 C20 H20B 109.5 . . ? H20A C20 H20B 108.1 . . ? 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 -178.76(15) . . . . ? C10 C1 C2 C3 54.9(2) . . . . ? C1 C2 C3 C4 -59.2(2) . . . . ? C2 C3 C4 C19 169.86(17) . . . . ? C2 C3 C4 C18 -71.9(2) . . . . ? C2 C3 C4 C5 53.2(2) . . . . ? C19 C4 C5 C6 64.6(2) . . . . ? C18 C4 C5 C6 -56.1(2) . . . . ? C3 C4 C5 C6 -178.97(15) . . . . ? C19 C4 C5 C10 -165.57(16) . . . . ? C18 C4 C5 C10 73.7(2) . . . . ? C3 C4 C5 C10 -49.2(2) . . . . ? C16 O4 C6 C7 25.80(18) . . . . ? C16 O4 C6 C5 -90.92(17) . . . . ? C10 C5 C6 O4 100.71(16) . . . . ? C4 C5 C6 O4 -124.68(16) . . . . ? C10 C5 C6 C7 -10.20(19) . . . . ? C4 C5 C6 C7 124.41(16) . . . . ? C20 O2 C7 O3 -175.61(14) . . . . ? C20 O2 C7 C6 63.97(19) . . . . ? C20 O2 C7 C8 -48.54(19) . . . . ? O4 C6 C7 O3 75.47(16) . . . . ? C5 C6 C7 O3 -167.56(14) . . . . ? O4 C6 C7 O2 -166.13(15) . . . . ? C5 C6 C7 O2 -49.2(2) . . . . ? O4 C6 C7 C8 -44.31(16) . . . . ? C5 C6 C7 C8 72.66(16) . . . . ? O3 C7 C8 C16 -71.27(17) . . . . ? O2 C7 C8 C16 165.69(14) . . . . ? C6 C7 C8 C16 45.35(15) . . . . ? O3 C7 C8 C14 51.6(2) . . . . ? O2 C7 C8 C14 -71.43(19) . . . . ? C6 C7 C8 C14 168.23(15) . . . . ? O3 C7 C8 C9 177.42(14) . . . . ? O2 C7 C8 C9 54.37(18) . . . . ? C6 C7 C8 C9 -65.96(16) . . . . ? C16 C8 C9 C11 125.32(16) . . . . ? C14 C8 C9 C11 -2.83(19) . . . . ? C7 C8 C9 C11 -130.02(16) . . . . ? C16 C8 C9 C10 -104.03(16) . . . . ? C14 C8 C9 C10 127.82(15) . . . . ? C7 C8 C9 C10 0.63(18) . . . . ? O1 C1 C10 C20 -49.1(2) . . . . ? C2 C1 C10 C20 76.20(19) . . . . ? O1 C1 C10 C9 70.36(18) . . . . ? C2 C1 C10 C9 -164.39(15) . . . . ? O1 C1 C10 C5 -172.74(14) . . . . ? C2 C1 C10 C5 -47.49(19) . . . . ? C11 C9 C10 C20 71.02(19) . . . . ? C8 C9 C10 C20 -56.30(17) . . . . ? C11 C9 C10 C1 -49.9(2) . . . . ? C8 C9 C10 C1 -177.18(13) . . . . ? C11 C9 C10 C5 -170.11(14) . . . . ? C8 C9 C10 C5 62.57(16) . . . . ? C6 C5 C10 C20 57.95(18) . . . . ? C4 C5 C10 C20 -74.71(19) . . . . ? C6 C5 C10 C1 -179.60(13) . . . . ? C4 C5 C10 C1 47.7(2) . . . . ? C6 C5 C10 C9 -57.70(17) . . . . ? C4 C5 C10 C9 169.64(14) . . . . ? C10 C9 C11 C12 -177.53(15) . . . . ? C8 C9 C11 C12 -51.74(19) . . . . ? C9 C11 C12 C13 57.0(2) . . . . ? C11 C12 C13 C15 119.5(2) . . . . ? C11 C12 C13 C14 -4.8(3) . . . . ? C15 C13 C14 O6 57.4(2) . . . . ? C12 C13 C14 O6 -177.96(16) . . . . ? C15 C13 C14 C8 -175.90(18) . . . . ? C12 C13 C14 C8 -51.3(2) . . . . ? C16 C8 C14 O6 58.4(2) . . . . ? C7 C8 C14 O6 -53.98(19) . . . . ? C9 C8 C14 O6 -178.12(14) . . . . ? C16 C8 C14 C13 -68.1(2) . . . . ? C7 C8 C14 C13 179.54(16) . . . . ? C9 C8 C14 C13 55.40(19) . . . . ? C14 C13 C15 O7 -116.2(3) . . . . ? C12 C13 C15 O7 119.3(3) . . . . ? C14 C13 C15 C17 65.9(3) . . . . ? C12 C13 C15 C17 -58.6(3) . . . . ? C6 O4 C16 O5 -177.57(18) . . . . ? C6 O4 C16 C8 4.43(19) . . . . ? C14 C8 C16 O5 28.4(3) . . . . ? C7 C8 C16 O5 150.1(2) . . . . ? C9 C8 C16 O5 -97.4(2) . . . . ? C14 C8 C16 O4 -153.80(16) . . . . ? C7 C8 C16 O4 -32.06(17) . . . . ? C9 C8 C16 O4 80.37(17) . . . . ? C7 O2 C20 C10 -12.9(2) . . . . ? C1 C10 C20 O2 -170.36(14) . . . . ? C9 C10 C20 O2 66.69(18) . . . . ? C5 C10 C20 O2 -47.48(19) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1 O2 0.82 2.10 2.8582(17) 154.7 2 O3 H3 O6 0.82 1.94 2.676(2) 149.4 . O6 H6 O7 0.82 1.98 2.733(3) 151.5 2_646 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.196 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.049