data_shelxl _audit_creation_method SHELXL-97 _publ_section_references ; CrystalClear, Rigaku Corp., (1999) Altomare, A., M. Burla, M. Camalli, G. Cascarano, C. Giacovazzo A. Guagliardi, A. Moliterni, G. Polidori & R. Spagna. (1999) J. Appl. Cryst. 32, 115-119. Sheldrick, G.M. SHELXL97. Program for crystal structure refinement. University of Gottingen, Germany, 1997. ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H26 O5' _chemical_formula_weight 406.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_Int_Tables_number 19 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 6.4191(8) _cell_length_b 12.2108(16) _cell_length_c 27.390(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2146.9(5) _cell_formula_units_Z 4 _cell_measurement_temperature 143(1) _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.258 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.8174 _diffrn_ambient_temperature 143(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'CCD Area Detector' _diffrn_measurement_device_type 'Rigaku Mercury' _diffrn_measurement_method 'phi and omega rotations' _diffrn_reflns_number 6608 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0491 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 2.79 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3646 _reflns_number_gt 2887 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku, 1999)' _computing_data_reduction 'CrystalClear (Rigaku, 1999)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0479P)^2^+0.6641P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _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 -0.1(15) _refine_ls_number_reflns 3646 _refine_ls_number_parameters 275 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0693 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_ref 0.1225 _refine_ls_wR_factor_gt 0.1049 _refine_ls_goodness_of_fit_ref 1.119 _refine_ls_restrained_S_all 1.119 _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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.3548(5) 0.8847(2) 0.43251(10) 0.0274(6) Uani 1 1 d . . . C2 C 0.1365(4) 0.9165(2) 0.41782(10) 0.0276(6) Uani 1 1 d . . . C3 C 0.0035(5) 0.8728(2) 0.46131(11) 0.0334(7) Uani 1 1 d . . . H3A H 0.0597 0.8973 0.4923 0.044 Uiso 1 1 calc R . . H3B H -0.1401 0.8969 0.4586 0.044 Uiso 1 1 calc R . . C4 C 0.0197(5) 0.7473(2) 0.45631(10) 0.0331(7) Uani 1 1 d . . . H4A H 0.0808 0.7144 0.4852 0.044 Uiso 1 1 calc R . . H4B H -0.1155 0.7144 0.4503 0.044 Uiso 1 1 calc R . . C5 C 0.1635(4) 0.7359(2) 0.41193(10) 0.0274(6) Uani 1 1 d . . . C6 C 0.0959(4) 0.8302(2) 0.37751(10) 0.0283(6) Uani 1 1 d . . . C7 C 0.1101(5) 1.0370(2) 0.40613(13) 0.0434(8) Uani 1 1 d . . . H7A H 0.1519 1.0800 0.4338 0.065 Uiso 1 1 calc R . . H7B H -0.0333 1.0516 0.3987 0.065 Uiso 1 1 calc R . . H7C H 0.1951 1.0556 0.3785 0.065 Uiso 1 1 calc R . . C8 C 0.2388(5) 0.8412(3) 0.33285(11) 0.0391(8) Uani 1 1 d . . . H8A H 0.3809 0.8468 0.3434 0.059 Uiso 1 1 calc R . . H8B H 0.2016 0.9057 0.3148 0.059 Uiso 1 1 calc R . . H8C H 0.2231 0.7780 0.3123 0.059 Uiso 1 1 calc R . . C9 C -0.1310(5) 0.8245(3) 0.36008(11) 0.0397(8) Uani 1 1 d . . . H9A H -0.1471 0.7640 0.3380 0.060 Uiso 1 1 calc R . . H9B H -0.1666 0.8914 0.3436 0.060 Uiso 1 1 calc R . . H9C H -0.2212 0.8145 0.3877 0.060 Uiso 1 1 calc R . . C10 C 0.1753(5) 0.6242(2) 0.39000(12) 0.0319(7) Uani 1 1 d . . . C11 C 0.3854(5) 0.4676(2) 0.37307(10) 0.0307(7) Uani 1 1 d . . . H11 H 0.2483 0.4332 0.3695 0.041 Uiso 1 1 calc R . . C12 C 0.5210(5) 0.3985(2) 0.40487(10) 0.0301(7) Uani 1 1 d . . . C13 C 0.6914(5) 0.4403(3) 0.42960(12) 0.0369(8) Uani 1 1 d . . . H13 H 0.7192 0.5150 0.4281 0.049 Uiso 1 1 calc R . . C14 C 0.8207(5) 0.3733(3) 0.45647(13) 0.0443(8) Uani 1 1 d . . . H14 H 0.9335 0.4029 0.4732 0.059 Uiso 1 1 calc R . . C15 C 0.7819(5) 0.2611(3) 0.45852(12) 0.0440(8) Uani 1 1 d . . . H15 H 0.8684 0.2155 0.4766 0.059 Uiso 1 1 calc R . . C16 C 0.6140(5) 0.2181(3) 0.43344(12) 0.0404(8) Uani 1 1 d . . . H16 H 0.5885 0.1431 0.4344 0.054 Uiso 1 1 calc R . . C17 C 0.4839(5) 0.2858(2) 0.40699(11) 0.0357(7) Uani 1 1 d . . . H17 H 0.3707 0.2562 0.3904 0.047 Uiso 1 1 calc R . . C18 C 0.4836(5) 0.4840(2) 0.32354(11) 0.0342(7) Uani 1 1 d . . . H18 H 0.6292 0.5081 0.3239 0.046 Uiso 1 1 calc R . . C19 C 0.4218(5) 0.4180(2) 0.28055(11) 0.0366(7) Uani 1 1 d . . . H19 H 0.5334 0.4063 0.2567 0.049 Uiso 1 1 calc R . . C20 C 0.2601(5) 0.3317(3) 0.28094(10) 0.0336(7) Uani 1 1 d . . . C21 C 0.0598(5) 0.3504(3) 0.29777(12) 0.0417(8) Uani 1 1 d . . . H21 H 0.0211 0.4205 0.3075 0.056 Uiso 1 1 calc R . . C22 C -0.0831(5) 0.2659(3) 0.30019(12) 0.0446(8) Uani 1 1 d . . . H22 H -0.2160 0.2786 0.3124 0.059 Uiso 1 1 calc R . . C23 C -0.0279(6) 0.1623(3) 0.28436(12) 0.0477(9) Uani 1 1 d . . . H23 H -0.1238 0.1052 0.2857 0.064 Uiso 1 1 calc R . . C24 C 0.1698(6) 0.1439(3) 0.26652(12) 0.0466(9) Uani 1 1 d . . . H24 H 0.2061 0.0746 0.2554 0.062 Uiso 1 1 calc R . . C25 C 0.3142(6) 0.2274(3) 0.26508(11) 0.0413(8) Uani 1 1 d . . . H25 H 0.4479 0.2139 0.2535 0.055 Uiso 1 1 calc R . . O1 O 0.3685(3) 0.77324(15) 0.42886(7) 0.0277(5) Uani 1 1 d . . . O2 O 0.4988(3) 0.93923(16) 0.44650(8) 0.0361(5) Uani 1 1 d . . . O3 O 0.3627(3) 0.57619(15) 0.39478(7) 0.0319(5) Uani 1 1 d . . . O4 O 0.0264(3) 0.58200(18) 0.37091(8) 0.0426(6) Uani 1 1 d . . . O5 O 0.3566(3) 0.53127(17) 0.28565(8) 0.0399(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0283(16) 0.0251(14) 0.0289(14) -0.0019(13) 0.0031(13) 0.0027(14) C2 0.0235(14) 0.0285(15) 0.0309(14) -0.0017(13) -0.0026(12) 0.0032(13) C3 0.0257(15) 0.0394(17) 0.0351(15) -0.0091(14) 0.0040(14) -0.0011(14) C4 0.0299(16) 0.0362(17) 0.0333(16) -0.0013(14) 0.0046(13) -0.0025(14) C5 0.0184(14) 0.0300(15) 0.0339(15) -0.0027(13) 0.0043(12) -0.0004(13) C6 0.0289(16) 0.0286(15) 0.0274(14) 0.0009(13) 0.0000(12) 0.0004(13) C7 0.047(2) 0.0295(16) 0.054(2) -0.0065(16) -0.0093(17) 0.0101(15) C8 0.0457(19) 0.0416(19) 0.0301(15) 0.0022(15) 0.0025(14) 0.0013(16) C9 0.0358(18) 0.0456(18) 0.0378(17) -0.0043(16) -0.0093(14) 0.0056(16) C10 0.0242(16) 0.0299(15) 0.0415(17) -0.0007(14) 0.0049(14) 0.0011(14) C11 0.0348(17) 0.0221(14) 0.0351(15) -0.0060(13) 0.0014(14) 0.0029(13) C12 0.0344(16) 0.0266(14) 0.0293(14) 0.0009(13) 0.0046(13) 0.0040(13) C13 0.0355(18) 0.0312(16) 0.0440(18) -0.0039(15) -0.0005(15) 0.0013(14) C14 0.0418(19) 0.0403(19) 0.051(2) -0.0056(17) -0.0054(16) 0.0018(16) C15 0.048(2) 0.0416(19) 0.0426(18) 0.0023(16) -0.0064(16) 0.0155(17) C16 0.053(2) 0.0262(15) 0.0416(17) 0.0044(15) 0.0009(16) 0.0057(15) C17 0.0434(19) 0.0284(15) 0.0353(16) -0.0007(13) -0.0003(15) -0.0024(15) C18 0.0356(17) 0.0309(15) 0.0363(16) 0.0054(14) 0.0026(14) 0.0044(14) C19 0.0426(19) 0.0352(17) 0.0320(15) -0.0009(15) 0.0021(14) 0.0089(15) C20 0.0398(18) 0.0334(16) 0.0275(14) -0.0003(14) -0.0039(14) 0.0050(15) C21 0.039(2) 0.0402(19) 0.0457(18) -0.0091(16) -0.0110(15) 0.0088(15) C22 0.042(2) 0.048(2) 0.0435(18) -0.0059(17) -0.0124(15) 0.0006(16) C23 0.060(2) 0.0401(19) 0.0433(18) -0.0001(17) -0.0126(18) -0.0073(18) C24 0.065(2) 0.0387(19) 0.0363(17) -0.0053(16) -0.0046(17) 0.0030(19) C25 0.050(2) 0.0414(18) 0.0326(16) -0.0021(16) -0.0001(15) 0.0061(18) O1 0.0236(10) 0.0251(10) 0.0346(10) -0.0018(9) -0.0022(9) 0.0027(9) O2 0.0252(11) 0.0315(11) 0.0515(13) -0.0055(10) -0.0041(10) -0.0031(9) O3 0.0313(11) 0.0245(10) 0.0399(11) -0.0056(9) -0.0001(9) 0.0037(9) O4 0.0272(12) 0.0392(12) 0.0615(14) -0.0131(11) -0.0002(11) -0.0023(10) O5 0.0465(13) 0.0349(11) 0.0384(12) 0.0075(10) -0.0021(11) 0.0052(11) 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 O2 1.202(3) . ? C1 O1 1.368(3) . ? C1 C2 1.508(4) . ? C2 C7 1.514(4) . ? C2 C6 1.549(4) . ? C2 C3 1.560(4) . ? C3 C4 1.543(4) . ? C4 C5 1.532(4) . ? C5 O1 1.468(3) . ? C5 C10 1.492(4) . ? C5 C6 1.550(4) . ? C6 C9 1.534(4) . ? C6 C8 1.535(4) . ? C10 O4 1.205(4) . ? C10 O3 1.345(4) . ? C11 O3 1.460(3) . ? C11 C12 1.493(4) . ? C11 C18 1.509(4) . ? C12 C13 1.384(4) . ? C12 C17 1.398(4) . ? C13 C14 1.379(4) . ? C14 C15 1.393(5) . ? C15 C16 1.382(5) . ? C16 C17 1.381(4) . ? C18 O5 1.440(4) . ? C18 C19 1.481(4) . ? C19 O5 1.452(4) . ? C19 C20 1.479(4) . ? C20 C21 1.385(4) . ? C20 C25 1.390(4) . ? C21 C22 1.383(5) . ? C22 C23 1.384(5) . ? C23 C24 1.378(5) . ? C24 C25 1.378(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 C1 O1 121.7(3) . . ? O2 C1 C2 131.1(3) . . ? O1 C1 C2 107.2(2) . . ? C1 C2 C7 114.2(2) . . ? C1 C2 C6 99.9(2) . . ? C7 C2 C6 119.4(3) . . ? C1 C2 C3 102.5(2) . . ? C7 C2 C3 115.6(3) . . ? C6 C2 C3 102.7(2) . . ? C4 C3 C2 103.6(2) . . ? C5 C4 C3 101.6(2) . . ? O1 C5 C10 111.4(2) . . ? O1 C5 C4 105.1(2) . . ? C10 C5 C4 115.6(2) . . ? O1 C5 C6 102.2(2) . . ? C10 C5 C6 116.6(2) . . ? C4 C5 C6 104.3(2) . . ? C9 C6 C8 108.9(2) . . ? C9 C6 C2 114.3(2) . . ? C8 C6 C2 114.1(2) . . ? C9 C6 C5 114.9(2) . . ? C8 C6 C5 112.5(2) . . ? C2 C6 C5 91.4(2) . . ? O4 C10 O3 124.5(3) . . ? O4 C10 C5 121.7(3) . . ? O3 C10 C5 113.9(3) . . ? O3 C11 C12 109.5(2) . . ? O3 C11 C18 106.7(2) . . ? C12 C11 C18 110.9(2) . . ? C13 C12 C17 118.5(3) . . ? C13 C12 C11 122.6(3) . . ? C17 C12 C11 118.8(3) . . ? C14 C13 C12 121.2(3) . . ? C13 C14 C15 119.8(3) . . ? C16 C15 C14 119.5(3) . . ? C17 C16 C15 120.3(3) . . ? C16 C17 C12 120.6(3) . . ? O5 C18 C19 59.58(19) . . ? O5 C18 C11 117.7(2) . . ? C19 C18 C11 122.0(3) . . ? O5 C19 C20 118.4(3) . . ? O5 C19 C18 58.80(18) . . ? C20 C19 C18 124.7(3) . . ? C21 C20 C25 119.2(3) . . ? C21 C20 C19 122.4(3) . . ? C25 C20 C19 118.4(3) . . ? C22 C21 C20 120.6(3) . . ? C21 C22 C23 119.9(3) . . ? C24 C23 C22 119.7(3) . . ? C25 C24 C23 120.7(3) . . ? C24 C25 C20 120.0(3) . . ? C1 O1 C5 105.9(2) . . ? C10 O3 C11 116.4(2) . . ? C18 O5 C19 61.61(19) . . ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.191 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.053