data_yds10 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H28 O3' _chemical_formula_weight 316.42 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)/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 10.9460(16) _cell_length_b 15.700(2) _cell_length_c 10.6744(16) _cell_angle_alpha 90.00 _cell_angle_beta 112.131(2) _cell_angle_gamma 90.00 _cell_volume 1699.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 125(2) _cell_measurement_reflns_used 7112 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 30.54 _exptl_crystal_description BLOCK _exptl_crystal_colour COLORLESS _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.081 _exptl_absorpt_correction_type EMPIRICAL _exptl_absorpt_correction_T_min 0.9863 _exptl_absorpt_correction_T_max 0.9960 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 125(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 27367 _diffrn_reflns_av_R_equivalents 0.0682 _diffrn_reflns_av_sigmaI/netI 0.0555 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 30.69 _reflns_number_total 5272 _reflns_number_gt 3588 _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^)+(0.0624P)^2^+0.2236P] 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_number_reflns 5272 _refine_ls_number_parameters 211 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1323 _refine_ls_wR_factor_gt 0.1161 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 -0.05593(10) -0.23130(6) -0.47030(10) 0.0231(2) Uani 1 1 d . . . O2 O -0.20177(11) -0.18659(7) -0.66871(10) 0.0274(2) Uani 1 1 d . . . O3 O -0.07372(10) 0.07964(6) -0.38042(10) 0.0239(2) Uani 1 1 d . . . C1 C -0.14831(14) -0.17632(9) -0.54818(14) 0.0209(3) Uani 1 1 d . . . C2 C -0.17160(14) -0.10702(9) -0.46250(14) 0.0212(3) Uani 1 1 d . . . H2A H -0.2576 -0.1150 -0.4534 0.025 Uiso 1 1 calc R . . H2B H -0.1706 -0.0504 -0.5028 0.025 Uiso 1 1 calc R . . C3 C -0.05817(13) -0.11506(8) -0.32502(13) 0.0173(3) Uani 1 1 d . . . H3A H -0.0928 -0.1091 -0.2512 0.021 Uiso 1 1 calc R . . C4 C -0.00978(14) -0.20726(8) -0.32777(13) 0.0193(3) Uani 1 1 d . . . H4A H -0.0511 -0.2456 -0.2800 0.023 Uiso 1 1 calc R . . C5 C 0.13831(15) -0.21635(9) -0.26440(14) 0.0229(3) Uani 1 1 d . . . H5A H 0.1785 -0.1968 -0.3284 0.027 Uiso 1 1 calc R . . H5B H 0.1624 -0.2768 -0.2422 0.027 Uiso 1 1 calc R . . C6 C 0.18907(15) -0.16228(8) -0.13555(14) 0.0204(3) Uani 1 1 d . . . H6A H 0.2833 -0.1753 -0.0844 0.024 Uiso 1 1 calc R . . H6B H 0.1396 -0.1772 -0.0777 0.024 Uiso 1 1 calc R . . C7 C 0.17336(13) -0.06594(8) -0.16822(13) 0.0160(3) Uani 1 1 d . . . C8 C 0.05391(13) -0.05039(8) -0.30325(13) 0.0154(3) Uani 1 1 d . . . H8A H 0.0835 -0.0523 -0.3812 0.019 Uiso 1 1 calc R . . C9 C 0.00555(13) 0.03865(8) -0.28919(13) 0.0168(3) Uani 1 1 d . . . C10 C 0.07068(14) 0.06791(8) -0.14492(13) 0.0177(3) Uani 1 1 d . . . H10A H 0.0048 0.0921 -0.1119 0.021 Uiso 1 1 calc R . . H10B H 0.1384 0.1117 -0.1366 0.021 Uiso 1 1 calc R . . C11 C 0.13421(13) -0.01241(8) -0.06468(12) 0.0149(3) Uani 1 1 d . . . H11A H 0.0619 -0.0445 -0.0499 0.018 Uiso 1 1 calc R . . C12 C 0.23910(13) 0.00411(8) 0.07469(13) 0.0174(3) Uani 1 1 d . . . C13 C 0.31074(14) -0.07326(9) 0.15228(14) 0.0207(3) Uani 1 1 d . . . H13A H 0.3670 -0.0960 0.1060 0.025 Uiso 1 1 calc R . . H13B H 0.2441 -0.1174 0.1462 0.025 Uiso 1 1 calc R . . C14 C 0.39718(15) -0.06091(10) 0.30150(14) 0.0257(3) Uani 1 1 d . . . H14A H 0.4592 -0.0132 0.3107 0.031 Uiso 1 1 calc R . . H14B H 0.3409 -0.0458 0.3522 0.031 Uiso 1 1 calc R . . C15 C 0.47393(14) -0.14027(10) 0.36111(14) 0.0234(3) Uani 1 1 d . . . H15A H 0.5264 -0.1625 0.3153 0.028 Uiso 1 1 calc R . . C16 C 0.47784(14) -0.18358(9) 0.47020(14) 0.0213(3) Uani 1 1 d . . . C17 C 0.56518(15) -0.26083(10) 0.51755(16) 0.0281(3) Uani 1 1 d . . . H17A H 0.6084 -0.2729 0.4541 0.042 Uiso 1 1 calc R . . H17B H 0.5116 -0.3100 0.5217 0.042 Uiso 1 1 calc R . . H17C H 0.6322 -0.2499 0.6076 0.042 Uiso 1 1 calc R . . C18 C 0.40113(16) -0.16031(10) 0.55589(16) 0.0278(3) Uani 1 1 d . . . H18A H 0.3449 -0.1110 0.5162 0.042 Uiso 1 1 calc R . . H18B H 0.4624 -0.1461 0.6474 0.042 Uiso 1 1 calc R . . H18C H 0.3460 -0.2086 0.5600 0.042 Uiso 1 1 calc R . . C19 C 0.29878(14) -0.03026(9) -0.18116(14) 0.0217(3) Uani 1 1 d . . . H19A H 0.3207 -0.0643 -0.2468 0.033 Uiso 1 1 calc R . . H19B H 0.3719 -0.0327 -0.0930 0.033 Uiso 1 1 calc R . . H19C H 0.2837 0.0290 -0.2120 0.033 Uiso 1 1 calc R . . C20 C 0.26110(15) 0.08193(9) 0.12784(14) 0.0229(3) Uani 1 1 d . . . H20A H 0.3235 0.0902 0.2172 0.028 Uiso 1 1 calc R . . H20B H 0.2144 0.1292 0.0764 0.028 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 0.0303(6) 0.0175(5) 0.0187(5) -0.0030(4) 0.0060(4) -0.0014(4) O2 0.0289(6) 0.0313(6) 0.0186(5) -0.0025(4) 0.0051(4) -0.0069(5) O3 0.0265(5) 0.0189(5) 0.0213(5) 0.0039(4) 0.0035(4) 0.0041(4) C1 0.0212(7) 0.0197(7) 0.0214(7) 0.0006(5) 0.0077(6) -0.0060(5) C2 0.0200(7) 0.0206(7) 0.0207(7) -0.0016(5) 0.0048(5) -0.0021(5) C3 0.0188(6) 0.0159(6) 0.0176(6) -0.0004(5) 0.0072(5) -0.0016(5) C4 0.0271(7) 0.0135(6) 0.0171(6) -0.0014(5) 0.0079(6) -0.0030(5) C5 0.0284(8) 0.0153(6) 0.0231(7) -0.0018(5) 0.0076(6) 0.0042(6) C6 0.0236(7) 0.0148(6) 0.0197(7) -0.0001(5) 0.0048(5) 0.0039(5) C7 0.0175(6) 0.0142(6) 0.0152(6) 0.0002(5) 0.0049(5) 0.0014(5) C8 0.0174(6) 0.0138(6) 0.0147(6) 0.0009(5) 0.0056(5) 0.0006(5) C9 0.0177(6) 0.0150(6) 0.0181(6) 0.0015(5) 0.0071(5) -0.0010(5) C10 0.0220(7) 0.0143(6) 0.0167(6) 0.0012(5) 0.0071(5) 0.0025(5) C11 0.0174(6) 0.0132(6) 0.0142(6) 0.0004(5) 0.0059(5) 0.0005(5) C12 0.0177(6) 0.0180(6) 0.0165(6) 0.0016(5) 0.0065(5) 0.0009(5) C13 0.0229(7) 0.0183(6) 0.0177(6) 0.0018(5) 0.0042(5) 0.0013(5) C14 0.0255(7) 0.0266(7) 0.0198(7) 0.0009(6) 0.0026(6) 0.0046(6) C15 0.0196(7) 0.0276(7) 0.0197(7) 0.0002(6) 0.0036(5) 0.0039(6) C16 0.0169(6) 0.0224(7) 0.0198(7) -0.0020(5) 0.0014(5) -0.0009(5) C17 0.0235(8) 0.0268(8) 0.0308(8) 0.0059(6) 0.0068(6) 0.0021(6) C18 0.0277(8) 0.0304(8) 0.0256(8) -0.0021(6) 0.0103(6) -0.0023(6) C19 0.0194(7) 0.0252(7) 0.0217(7) -0.0026(6) 0.0090(6) -0.0008(6) C20 0.0260(7) 0.0199(7) 0.0198(7) -0.0009(5) 0.0050(6) -0.0001(6) _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 1.3510(17) . ? O1 C4 1.4606(16) . ? O2 C1 1.2068(17) . ? O3 C9 1.2160(16) . ? C1 C2 1.504(2) . ? C2 C3 1.5291(19) . ? C3 C8 1.5412(18) . ? C3 C4 1.5454(19) . ? C4 C5 1.510(2) . ? C5 C6 1.5314(19) . ? C6 C7 1.5471(18) . ? C7 C19 1.5365(19) . ? C7 C8 1.5578(18) . ? C7 C11 1.5711(18) . ? C8 C9 1.5221(18) . ? C9 C10 1.5046(18) . ? C10 C11 1.5358(17) . ? C11 C12 1.5205(18) . ? C12 C20 1.3302(19) . ? C12 C13 1.5123(18) . ? C13 C14 1.5279(19) . ? C14 C15 1.503(2) . ? C15 C16 1.335(2) . ? C16 C18 1.501(2) . ? C16 C17 1.509(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C4 111.15(11) . . ? O2 C1 O1 121.38(13) . . ? O2 C1 C2 128.30(14) . . ? O1 C1 C2 110.31(12) . . ? C1 C2 C3 105.16(11) . . ? C2 C3 C8 113.75(11) . . ? C2 C3 C4 102.67(10) . . ? C8 C3 C4 111.15(11) . . ? O1 C4 C5 109.51(11) . . ? O1 C4 C3 105.98(10) . . ? C5 C4 C3 113.44(11) . . ? C4 C5 C6 108.36(12) . . ? C5 C6 C7 111.56(11) . . ? C19 C7 C6 110.46(11) . . ? C19 C7 C8 109.06(11) . . ? C6 C7 C8 110.19(10) . . ? C19 C7 C11 110.97(10) . . ? C6 C7 C11 113.64(11) . . ? C8 C7 C11 102.17(10) . . ? C9 C8 C3 109.47(11) . . ? C9 C8 C7 104.75(10) . . ? C3 C8 C7 112.28(10) . . ? O3 C9 C10 125.32(12) . . ? O3 C9 C8 125.22(12) . . ? C10 C9 C8 109.46(11) . . ? C9 C10 C11 105.10(10) . . ? C12 C11 C10 114.95(11) . . ? C12 C11 C7 118.29(11) . . ? C10 C11 C7 103.48(10) . . ? C20 C12 C13 122.07(12) . . ? C20 C12 C11 121.51(12) . . ? C13 C12 C11 116.32(11) . . ? C12 C13 C14 117.30(12) . . ? C15 C14 C13 111.34(12) . . ? C16 C15 C14 128.34(14) . . ? C15 C16 C18 124.47(14) . . ? C15 C16 C17 120.64(14) . . ? C18 C16 C17 114.89(13) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.69 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.465 _refine_diff_density_min -0.261 _refine_diff_density_rms 0.054