data_sfy7_b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H28 O5' _chemical_formula_weight 384.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.4428(3) _cell_length_b 9.2903(5) _cell_length_c 19.7811(10) _cell_angle_alpha 87.538(2) _cell_angle_beta 85.332(2) _cell_angle_gamma 85.189(2) _cell_volume 992.75(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9938 _cell_measurement_theta_min 4.49 _cell_measurement_theta_max 78.75 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.286 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 412 _exptl_absorpt_coefficient_mu 0.726 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7851 _exptl_absorpt_correction_T_max 0.9928 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2009)' _exptl_special_details ; Bruker X8 Kappa DUO four-circle diffractometer, Bruker VENTURE CMOS Detector. ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker Turbo x-ray source rotating anode generator' _diffrn_radiation_monochromator 'Incoatec HELIOS MX multilayer optics' _diffrn_measurement_device_type 'Bruker D8 VENTURE' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean '10.24 pixels/mm' _diffrn_reflns_number 23571 _diffrn_reflns_av_R_equivalents 0.0375 _diffrn_reflns_av_sigmaI/netI 0.0235 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 4.49 _diffrn_reflns_theta_max 70.05 _reflns_number_total 3725 _reflns_number_gt 3362 _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^)+(0.0927P)^2^+0.4548P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3725 _refine_ls_number_parameters 260 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0565 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1550 _refine_ls_wR_factor_gt 0.1506 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 1.0219(2) 0.97535(12) 0.68790(6) 0.0256(3) Uani 1 1 d . . . O2 O 0.5858(2) 0.91701(13) 0.89383(6) 0.0286(3) Uani 1 1 d . . . O3 O 0.9792(2) 0.71660(13) 0.87726(6) 0.0283(3) Uani 1 1 d D . . H3 H 0.977(4) 0.740(2) 0.9172(8) 0.034 Uiso 1 1 d D . . O4 O 0.9836(3) 1.19865(17) 0.99084(7) 0.0533(4) Uani 1 1 d . . . O5 O 1.3981(3) 1.32130(18) 0.82936(9) 0.0578(5) Uani 1 1 d . . . C1 C 0.8463(3) 0.88210(17) 0.66198(8) 0.0247(4) Uani 1 1 d . . . C2 C 0.7347(3) 0.77639(17) 0.71745(8) 0.0238(4) Uani 1 1 d . . . H2 H 0.6021 0.7288 0.6968 0.029 Uiso 1 1 calc R . . C3 C 0.9159(3) 0.65642(17) 0.74297(8) 0.0273(4) Uani 1 1 d . . . H3A H 1.0643 0.6984 0.7570 0.033 Uiso 1 1 calc R . . H3B H 0.9691 0.5892 0.7061 0.033 Uiso 1 1 calc R . . C4 C 0.7921(3) 0.57413(18) 0.80326(9) 0.0306(4) Uani 1 1 d . . . H4A H 0.8996 0.4867 0.8147 0.037 Uiso 1 1 calc R . . H4B H 0.6333 0.5426 0.7905 0.037 Uiso 1 1 calc R . . C5 C 0.7442(3) 0.66798(18) 0.86544(8) 0.0266(4) Uani 1 1 d . . . C6 C 0.5611(3) 0.79699(18) 0.84803(8) 0.0256(4) Uani 1 1 d . . . H6 H 0.3884 0.7667 0.8540 0.031 Uiso 1 1 calc R . . C7 C 0.6084(3) 0.86557(17) 0.77643(8) 0.0230(3) Uani 1 1 d . . . H7 H 0.4495 0.9144 0.7619 0.028 Uiso 1 1 calc R . . C8 C 0.7728(3) 0.97799(17) 0.79188(8) 0.0231(3) Uani 1 1 d . . . C9 C 0.7458(3) 1.00577(17) 0.85990(8) 0.0256(4) Uani 1 1 d . . . C10 C 0.8853(3) 1.10486(18) 0.88825(9) 0.0292(4) Uani 1 1 d . . . C11 C 1.0658(3) 1.16870(18) 0.84233(9) 0.0293(4) Uani 1 1 d . . . C12 C 1.1054(3) 1.13103(17) 0.77528(9) 0.0279(4) Uani 1 1 d . . . H12 H 1.2289 1.1739 0.7462 0.033 Uiso 1 1 calc R . . C13 C 0.9621(3) 1.02892(16) 0.75018(8) 0.0239(3) Uani 1 1 d . . . C14 C 0.6415(3) 0.98284(18) 0.63283(8) 0.0280(4) Uani 1 1 d . . . H14A H 0.5256 0.9232 0.6128 0.034 Uiso 1 1 calc R . . H14B H 0.5481 1.0350 0.6706 0.034 Uiso 1 1 calc R . . C15 C 0.7287(4) 1.0940(2) 0.57894(10) 0.0392(5) Uani 1 1 d . . . H15A H 0.8558 1.1487 0.5971 0.047 Uiso 1 1 calc R . . H15B H 0.8062 1.0430 0.5387 0.047 Uiso 1 1 calc R . . C16 C 0.5213(4) 1.1973(2) 0.55786(9) 0.0367(4) Uani 1 1 d . . . H16 H 0.4337 1.1692 0.5216 0.044 Uiso 1 1 calc R . . C17 C 0.4451(4) 1.3249(2) 0.58428(9) 0.0349(4) Uani 1 1 d . . . C18 C 0.5578(5) 1.3885(3) 0.64136(12) 0.0533(6) Uani 1 1 d . . . H18A H 0.6963 1.3231 0.6556 0.080 Uiso 1 1 calc R . . H18B H 0.4331 1.4022 0.6797 0.080 Uiso 1 1 calc R . . H18C H 0.6178 1.4821 0.6263 0.080 Uiso 1 1 calc R . . C19 C 0.2300(4) 1.4160(2) 0.55800(11) 0.0460(5) Uani 1 1 d . . . H19A H 0.2860 1.5076 0.5387 0.069 Uiso 1 1 calc R . . H19B H 0.1033 1.4352 0.5953 0.069 Uiso 1 1 calc R . . H19C H 0.1602 1.3645 0.5228 0.069 Uiso 1 1 calc R . . C20 C 1.0036(3) 0.79831(19) 0.60718(9) 0.0304(4) Uani 1 1 d . . . H20A H 1.0711 0.8663 0.5727 0.046 Uiso 1 1 calc R . . H20B H 0.9012 0.7339 0.5860 0.046 Uiso 1 1 calc R . . H20C H 1.1397 0.7410 0.6276 0.046 Uiso 1 1 calc R . . C21 C 0.6391(4) 0.5841(2) 0.92726(9) 0.0361(4) Uani 1 1 d . . . H21A H 0.7594 0.5047 0.9395 0.054 Uiso 1 1 calc R . . H21B H 0.4856 0.5447 0.9168 0.054 Uiso 1 1 calc R . . H21C H 0.6047 0.6487 0.9653 0.054 Uiso 1 1 calc R . . C22 C 0.8509(4) 1.12867(19) 0.96037(9) 0.0335(4) Uani 1 1 d . . . H22 H 0.7167 1.0872 0.9856 0.040 Uiso 1 1 calc R . . C23 C 1.2265(4) 1.2791(2) 0.86370(11) 0.0406(5) Uani 1 1 d . . . H23 H 1.1894 1.3179 0.9074 0.049 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 0.0227(6) 0.0265(6) 0.0271(6) -0.0009(4) 0.0044(4) -0.0061(4) O2 0.0274(6) 0.0349(6) 0.0236(6) -0.0046(5) 0.0039(5) -0.0064(5) O3 0.0244(6) 0.0368(7) 0.0248(6) -0.0030(5) -0.0019(5) -0.0073(5) O4 0.0745(11) 0.0555(9) 0.0352(8) -0.0088(7) -0.0127(7) -0.0244(8) O5 0.0494(9) 0.0524(9) 0.0752(11) -0.0122(8) 0.0015(8) -0.0263(8) C1 0.0247(8) 0.0262(8) 0.0230(8) -0.0012(6) 0.0018(6) -0.0048(6) C2 0.0243(8) 0.0266(8) 0.0214(7) -0.0016(6) -0.0001(6) -0.0081(6) C3 0.0329(9) 0.0246(8) 0.0241(8) -0.0028(6) 0.0012(6) -0.0030(7) C4 0.0395(10) 0.0252(8) 0.0279(8) 0.0008(7) -0.0026(7) -0.0089(7) C5 0.0269(8) 0.0302(8) 0.0235(8) 0.0013(6) 0.0003(6) -0.0109(7) C6 0.0209(8) 0.0327(9) 0.0239(8) -0.0026(6) 0.0016(6) -0.0090(6) C7 0.0184(7) 0.0265(8) 0.0240(8) -0.0005(6) 0.0009(6) -0.0045(6) C8 0.0198(7) 0.0228(7) 0.0266(8) -0.0023(6) -0.0010(6) -0.0015(6) C9 0.0229(8) 0.0257(8) 0.0275(8) -0.0028(6) 0.0016(6) -0.0008(6) C10 0.0314(9) 0.0249(8) 0.0315(9) -0.0048(7) -0.0056(7) 0.0008(7) C11 0.0273(9) 0.0231(8) 0.0381(9) -0.0030(7) -0.0060(7) -0.0014(7) C12 0.0230(8) 0.0227(8) 0.0378(9) 0.0001(7) -0.0005(7) -0.0041(6) C13 0.0214(8) 0.0212(7) 0.0285(8) 0.0002(6) -0.0006(6) -0.0005(6) C14 0.0268(8) 0.0321(9) 0.0245(8) 0.0003(7) 0.0007(6) -0.0022(7) C15 0.0402(11) 0.0376(10) 0.0366(10) 0.0092(8) 0.0046(8) 0.0037(8) C16 0.0433(11) 0.0353(9) 0.0304(9) 0.0023(7) -0.0022(8) 0.0009(8) C17 0.0403(10) 0.0330(9) 0.0310(9) 0.0001(7) 0.0013(7) -0.0048(8) C18 0.0562(14) 0.0558(13) 0.0509(13) -0.0121(10) -0.0074(10) -0.0150(11) C19 0.0518(13) 0.0365(10) 0.0481(12) -0.0011(9) -0.0043(10) 0.0063(9) C20 0.0342(9) 0.0311(9) 0.0246(8) -0.0015(6) 0.0045(7) -0.0008(7) C21 0.0410(10) 0.0390(10) 0.0286(9) 0.0062(7) 0.0020(7) -0.0134(8) C22 0.0410(10) 0.0290(9) 0.0313(9) -0.0033(7) -0.0049(7) -0.0039(7) C23 0.0420(11) 0.0357(10) 0.0459(11) -0.0052(8) -0.0040(9) -0.0115(8) _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 C13 1.353(2) . ? O1 C1 1.4779(19) . ? O2 C9 1.366(2) . ? O2 C6 1.4879(19) . ? O3 C5 1.4315(19) . ? O3 H3 0.827(16) . ? O4 C22 1.221(2) . ? O5 C23 1.193(3) . ? C1 C20 1.524(2) . ? C1 C14 1.528(2) . ? C1 C2 1.561(2) . ? C2 C3 1.523(2) . ? C2 C7 1.542(2) . ? C2 H2 1.0000 . ? C3 C4 1.529(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.531(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C21 1.520(2) . ? C5 C6 1.539(2) . ? C6 C7 1.539(2) . ? C6 H6 1.0000 . ? C7 C8 1.488(2) . ? C7 H7 1.0000 . ? C8 C13 1.369(2) . ? C8 C9 1.375(2) . ? C9 C10 1.403(2) . ? C10 C11 1.431(3) . ? C10 C22 1.448(2) . ? C11 C12 1.382(2) . ? C11 C23 1.498(2) . ? C12 C13 1.408(2) . ? C12 H12 0.9500 . ? C14 C15 1.527(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.493(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.336(3) . ? C16 H16 0.9500 . ? C17 C18 1.494(3) . ? C17 C19 1.501(3) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 H22 0.9500 . ? C23 H23 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 O1 C1 116.97(11) . . ? C9 O2 C6 106.46(11) . . ? C5 O3 H3 109.1(15) . . ? O1 C1 C20 103.29(12) . . ? O1 C1 C14 106.69(12) . . ? C20 C1 C14 112.31(14) . . ? O1 C1 C2 113.29(12) . . ? C20 C1 C2 110.59(13) . . ? C14 C1 C2 110.46(13) . . ? C3 C2 C7 111.29(13) . . ? C3 C2 C1 115.27(13) . . ? C7 C2 C1 108.64(12) . . ? C3 C2 H2 107.1 . . ? C7 C2 H2 107.1 . . ? C1 C2 H2 107.1 . . ? C2 C3 C4 109.67(14) . . ? C2 C3 H3A 109.7 . . ? C4 C3 H3A 109.7 . . ? C2 C3 H3B 109.7 . . ? C4 C3 H3B 109.7 . . ? H3A C3 H3B 108.2 . . ? C3 C4 C5 111.43(13) . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4B 109.3 . . ? C5 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? O3 C5 C21 110.75(14) . . ? O3 C5 C4 105.54(13) . . ? C21 C5 C4 111.97(14) . . ? O3 C5 C6 110.53(13) . . ? C21 C5 C6 109.65(14) . . ? C4 C5 C6 108.31(14) . . ? O2 C6 C5 109.48(13) . . ? O2 C6 C7 103.81(12) . . ? C5 C6 C7 114.78(13) . . ? O2 C6 H6 109.5 . . ? C5 C6 H6 109.5 . . ? C7 C6 H6 109.5 . . ? C8 C7 C6 99.59(12) . . ? C8 C7 C2 108.80(12) . . ? C6 C7 C2 121.37(13) . . ? C8 C7 H7 108.8 . . ? C6 C7 H7 108.8 . . ? C2 C7 H7 108.8 . . ? C13 C8 C9 121.43(15) . . ? C13 C8 C7 126.95(14) . . ? C9 C8 C7 110.42(14) . . ? O2 C9 C8 110.76(14) . . ? O2 C9 C10 127.06(15) . . ? C8 C9 C10 121.98(15) . . ? C9 C10 C11 115.46(15) . . ? C9 C10 C22 119.58(16) . . ? C11 C10 C22 124.83(16) . . ? C12 C11 C10 122.02(15) . . ? C12 C11 C23 115.48(16) . . ? C10 C11 C23 122.49(16) . . ? C11 C12 C13 119.74(15) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? O1 C13 C8 120.95(14) . . ? O1 C13 C12 120.33(14) . . ? C8 C13 C12 118.56(15) . . ? C15 C14 C1 115.34(14) . . ? C15 C14 H14A 108.4 . . ? C1 C14 H14A 108.4 . . ? C15 C14 H14B 108.4 . . ? C1 C14 H14B 108.4 . . ? H14A C14 H14B 107.5 . . ? C16 C15 C14 112.13(16) . . ? C16 C15 H15A 109.2 . . ? C14 C15 H15A 109.2 . . ? C16 C15 H15B 109.2 . . ? C14 C15 H15B 109.2 . . ? H15A C15 H15B 107.9 . . ? C17 C16 C15 127.28(19) . . ? C17 C16 H16 116.4 . . ? C15 C16 H16 116.4 . . ? C16 C17 C18 124.7(2) . . ? C16 C17 C19 120.94(18) . . ? C18 C17 C19 114.36(18) . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C1 C20 H20A 109.5 . . ? C1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 C21 H21A 109.5 . . ? C5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? O4 C22 C10 124.14(18) . . ? O4 C22 H22 117.9 . . ? C10 C22 H22 117.9 . . ? O5 C23 C11 124.11(19) . . ? O5 C23 H23 117.9 . . ? C11 C23 H23 117.9 . . ? 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 O3 H3 O4 0.827(16) 1.964(16) 2.7852(18) 172(2) 2_777 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 70.05 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.448 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.064