data_H3 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C34 H28 O8' _chemical_formula_sum 'C34 H28 O8' _chemical_formula_weight 564.56 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)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.7172(6) _cell_length_b 14.805(2) _cell_length_c 19.787(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.810(4) _cell_angle_gamma 90.00 _cell_volume 1378.8(3) _cell_formula_units_Z 2 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 4611 _cell_measurement_theta_min 1.7192 _cell_measurement_theta_max 28.5427 _exptl_crystal_description Prism _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.2000 _exptl_crystal_size_mid 0.0300 _exptl_crystal_size_min 0.0300 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9330 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'Jacobson, R. (1998) Private communication' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type CCD _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8788 _diffrn_reflns_av_R_equivalents 0.0307 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.72 _diffrn_reflns_theta_max 25.35 _reflns_number_total 2459 _reflns_number_gt 2121 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp., 2004)' _computing_cell_refinement 'CrystalClear (Rigaku Corp., 2004)' _computing_data_reduction 'CrystalClear (Rigaku Corp., 2004)' _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^)+(0.0710P)^2^+0.1665P] 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 0.010(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2459 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0499 _refine_ls_R_factor_gt 0.0432 _refine_ls_wR_factor_ref 0.1201 _refine_ls_wR_factor_gt 0.1124 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _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 C1 C 1.4371(3) 0.51345(9) 0.02738(7) 0.0196(3) Uani 1 1 d . . . H1A H 1.4855 0.5717 0.0447 0.024 Uiso 1 1 calc R . . C2 C 1.2309(3) 0.46129(9) 0.06337(7) 0.0196(3) Uani 1 1 d . . . C3 C 1.1315(3) 0.37637(9) 0.04157(7) 0.0205(3) Uani 1 1 d . . . H3A H 1.1927 0.3518 0.0007 0.025 Uiso 1 1 calc R . . C4 C 0.9457(3) 0.32778(9) 0.07874(7) 0.0204(3) Uani 1 1 d . . . H4A H 0.8831 0.2701 0.0630 0.025 Uiso 1 1 calc R . . C5 C 0.8477(3) 0.36145(9) 0.13886(7) 0.0189(3) Uani 1 1 d . . . C6 C 0.9364(3) 0.44797(9) 0.15891(7) 0.0212(3) Uani 1 1 d . . . H6A H 0.8664 0.4740 0.1984 0.025 Uiso 1 1 calc R . . C7 C 1.1244(3) 0.49627(9) 0.12220(7) 0.0211(4) Uani 1 1 d . . . H7A H 1.1827 0.5547 0.1373 0.025 Uiso 1 1 calc R . . C8 C 0.6636(3) 0.30629(9) 0.18084(7) 0.0196(3) Uani 1 1 d . . . C9 C 0.4914(3) 0.23724(9) 0.15264(7) 0.0198(3) Uani 1 1 d . . . H9A H 0.4900 0.2257 0.1054 0.024 Uiso 1 1 calc R . . C10 C 0.3218(3) 0.18497(9) 0.19250(7) 0.0204(3) Uani 1 1 d . . . C11 C 0.3221(3) 0.20010(9) 0.26161(7) 0.0224(4) Uani 1 1 d . . . H11A H 0.2070 0.1643 0.2888 0.027 Uiso 1 1 calc R . . C12 C 0.4930(3) 0.26836(9) 0.29089(7) 0.0228(4) Uani 1 1 d . . . C13 C 0.6611(3) 0.32036(9) 0.25057(7) 0.0206(3) Uani 1 1 d . . . H13A H 0.7771 0.3666 0.2711 0.025 Uiso 1 1 calc R . . C14 C 0.1380(3) 0.11550(9) 0.15687(8) 0.0222(4) Uani 1 1 d . . . O14 O 0.1297(2) 0.10065(7) 0.09676(5) 0.0294(3) Uani 1 1 d . . . O15 O -0.0205(2) 0.07037(7) 0.19973(5) 0.0270(3) Uani 1 1 d . . . C15 C -0.2090(3) 0.00315(10) 0.16836(9) 0.0298(4) Uani 1 1 d . . . H15A H -0.3337 0.0316 0.1329 0.045 Uiso 1 1 calc R . . H15B H -0.3244 -0.0234 0.2026 0.045 Uiso 1 1 calc R . . H15C H -0.0966 -0.0443 0.1483 0.045 Uiso 1 1 calc R . . C16 C 0.4907(4) 0.28435(10) 0.36512(8) 0.0292(4) Uani 1 1 d . . . O16 O 0.3663(3) 0.23790(8) 0.40330(6) 0.0551(4) Uani 1 1 d . . . O17 O 0.6419(2) 0.35742(7) 0.38517(5) 0.0288(3) Uani 1 1 d . . . C17 C 0.6588(5) 0.37715(12) 0.45692(8) 0.0460(5) Uani 1 1 d . . . H17A H 0.4677 0.3757 0.4736 0.069 Uiso 1 1 calc R . . H17B H 0.7418 0.4372 0.4647 0.069 Uiso 1 1 calc R . . H17C H 0.7783 0.3319 0.4811 0.069 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0205(8) 0.0182(7) 0.0202(7) 0.0020(5) 0.0017(6) -0.0004(5) C2 0.0178(8) 0.0212(7) 0.0198(7) 0.0033(5) 0.0022(6) 0.0008(6) C3 0.0220(8) 0.0221(7) 0.0178(7) -0.0005(5) 0.0043(6) 0.0011(6) C4 0.0229(8) 0.0173(7) 0.0211(8) -0.0014(5) 0.0017(6) -0.0012(5) C5 0.0182(8) 0.0204(7) 0.0179(7) 0.0021(5) 0.0011(6) 0.0005(5) C6 0.0229(8) 0.0234(8) 0.0179(7) -0.0017(5) 0.0051(6) 0.0002(6) C7 0.0228(8) 0.0191(7) 0.0214(8) -0.0007(5) 0.0024(7) -0.0011(5) C8 0.0198(8) 0.0178(7) 0.0214(7) 0.0026(5) 0.0039(6) 0.0031(5) C9 0.0203(8) 0.0200(7) 0.0193(7) 0.0019(5) 0.0026(6) 0.0027(6) C10 0.0197(8) 0.0168(7) 0.0248(8) 0.0026(5) 0.0024(6) 0.0016(5) C11 0.0224(8) 0.0196(7) 0.0256(8) 0.0059(6) 0.0060(7) 0.0013(6) C12 0.0269(8) 0.0197(7) 0.0222(8) 0.0035(6) 0.0056(7) 0.0039(6) C13 0.0214(8) 0.0184(7) 0.0221(8) 0.0011(5) 0.0021(6) 0.0011(6) C14 0.0210(8) 0.0190(7) 0.0265(8) 0.0055(6) 0.0015(7) 0.0016(6) O14 0.0340(7) 0.0275(6) 0.0267(6) -0.0005(4) 0.0023(5) -0.0065(5) O15 0.0256(6) 0.0243(6) 0.0309(6) 0.0060(4) 0.0010(5) -0.0088(4) C15 0.0259(9) 0.0250(8) 0.0381(10) 0.0013(6) -0.0007(8) -0.0072(6) C16 0.0410(10) 0.0236(8) 0.0236(8) 0.0043(6) 0.0067(8) -0.0002(7) O16 0.0994(12) 0.0408(8) 0.0278(7) 0.0008(5) 0.0238(7) -0.0276(7) O17 0.0410(7) 0.0282(6) 0.0171(6) 0.0009(4) 0.0014(5) -0.0028(5) C17 0.0813(15) 0.0392(10) 0.0170(8) -0.0011(7) -0.0003(9) -0.0055(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 C1 C1 1.330(3) 3_865 ? C1 C2 1.4637(19) . ? C1 H1A 0.9500 . ? C2 C7 1.3974(19) . ? C2 C3 1.400(2) . ? C3 C4 1.383(2) . ? C3 H3A 0.9500 . ? C4 C5 1.3967(19) . ? C4 H4A 0.9500 . ? C5 C6 1.397(2) . ? C5 C8 1.4853(19) . ? C6 C7 1.3828(19) . ? C6 H6A 0.9500 . ? C7 H7A 0.9500 . ? C8 C13 1.396(2) . ? C8 C9 1.399(2) . ? C9 C10 1.3948(19) . ? C9 H9A 0.9500 . ? C10 C11 1.386(2) . ? C10 C14 1.492(2) . ? C11 C12 1.395(2) . ? C11 H11A 0.9500 . ? C12 C13 1.3936(19) . ? C12 C16 1.489(2) . ? C13 H13A 0.9500 . ? C14 O14 1.2077(17) . ? C14 O15 1.3450(17) . ? O15 C15 1.4467(18) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 O16 1.2030(18) . ? C16 O17 1.3412(19) . ? O17 C17 1.4466(18) . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 C1 C2 125.81(16) 3_865 . ? C1 C1 H1A 117.1 3_865 . ? C2 C1 H1A 117.1 . . ? C7 C2 C3 117.26(12) . . ? C7 C2 C1 119.80(13) . . ? C3 C2 C1 122.93(12) . . ? C4 C3 C2 120.95(12) . . ? C4 C3 H3A 119.5 . . ? C2 C3 H3A 119.5 . . ? C3 C4 C5 121.66(13) . . ? C3 C4 H4A 119.2 . . ? C5 C4 H4A 119.2 . . ? C4 C5 C6 117.34(12) . . ? C4 C5 C8 121.27(12) . . ? C6 C5 C8 121.36(12) . . ? C7 C6 C5 121.03(12) . . ? C7 C6 H6A 119.5 . . ? C5 C6 H6A 119.5 . . ? C6 C7 C2 121.64(13) . . ? C6 C7 H7A 119.2 . . ? C2 C7 H7A 119.2 . . ? C13 C8 C9 117.42(12) . . ? C13 C8 C5 120.95(13) . . ? C9 C8 C5 121.62(12) . . ? C10 C9 C8 121.32(13) . . ? C10 C9 H9A 119.3 . . ? C8 C9 H9A 119.3 . . ? C11 C10 C9 120.35(13) . . ? C11 C10 C14 122.71(12) . . ? C9 C10 C14 116.91(13) . . ? C10 C11 C12 119.33(12) . . ? C10 C11 H11A 120.3 . . ? C12 C11 H11A 120.3 . . ? C13 C12 C11 119.86(13) . . ? C13 C12 C16 121.24(14) . . ? C11 C12 C16 118.90(12) . . ? C12 C13 C8 121.72(14) . . ? C12 C13 H13A 119.1 . . ? C8 C13 H13A 119.1 . . ? O14 C14 O15 123.20(14) . . ? O14 C14 C10 124.81(13) . . ? O15 C14 C10 111.99(12) . . ? C14 O15 C15 115.02(12) . . ? O15 C15 H15A 109.5 . . ? O15 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O15 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? O16 C16 O17 123.19(14) . . ? O16 C16 C12 124.37(15) . . ? O17 C16 C12 112.43(12) . . ? C16 O17 C17 116.53(12) . . ? O17 C17 H17A 109.5 . . ? O17 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? O17 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 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 C1 C1 C2 C7 177.18(18) 3_865 . . . ? C1 C1 C2 C3 -2.9(3) 3_865 . . . ? C7 C2 C3 C4 -2.9(2) . . . . ? C1 C2 C3 C4 177.24(13) . . . . ? C2 C3 C4 C5 0.6(2) . . . . ? C3 C4 C5 C6 2.3(2) . . . . ? C3 C4 C5 C8 -175.83(13) . . . . ? C4 C5 C6 C7 -3.0(2) . . . . ? C8 C5 C6 C7 175.18(13) . . . . ? C5 C6 C7 C2 0.7(2) . . . . ? C3 C2 C7 C6 2.2(2) . . . . ? C1 C2 C7 C6 -177.89(13) . . . . ? C4 C5 C8 C13 152.98(14) . . . . ? C6 C5 C8 C13 -25.1(2) . . . . ? C4 C5 C8 C9 -25.6(2) . . . . ? C6 C5 C8 C9 156.30(14) . . . . ? C13 C8 C9 C10 0.6(2) . . . . ? C5 C8 C9 C10 179.20(12) . . . . ? C8 C9 C10 C11 -0.5(2) . . . . ? C8 C9 C10 C14 177.71(12) . . . . ? C9 C10 C11 C12 0.2(2) . . . . ? C14 C10 C11 C12 -177.87(13) . . . . ? C10 C11 C12 C13 -0.1(2) . . . . ? C10 C11 C12 C16 179.72(13) . . . . ? C11 C12 C13 C8 0.1(2) . . . . ? C16 C12 C13 C8 -179.62(13) . . . . ? C9 C8 C13 C12 -0.4(2) . . . . ? C5 C8 C13 C12 -179.03(13) . . . . ? C11 C10 C14 O14 179.42(14) . . . . ? C9 C10 C14 O14 1.3(2) . . . . ? C11 C10 C14 O15 -0.56(19) . . . . ? C9 C10 C14 O15 -178.72(11) . . . . ? O14 C14 O15 C15 -1.3(2) . . . . ? C10 C14 O15 C15 178.69(12) . . . . ? C13 C12 C16 O16 -174.52(16) . . . . ? C11 C12 C16 O16 5.7(3) . . . . ? C13 C12 C16 O17 6.0(2) . . . . ? C11 C12 C16 O17 -173.72(13) . . . . ? O16 C16 O17 C17 2.2(2) . . . . ? C12 C16 O17 C17 -178.38(13) . . . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.203 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.048