data_yl_9_105mch _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 O3' _chemical_formula_weight 314.41 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 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 8.8153(7) _cell_length_b 9.6717(8) _cell_length_c 10.6323(9) _cell_angle_alpha 90.00 _cell_angle_beta 99.800(5) _cell_angle_gamma 90.00 _cell_volume 893.27(13) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3639 _cell_measurement_theta_min 4.22 _cell_measurement_theta_max 68.95 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.169 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.611 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8774 _exptl_absorpt_correction_T_max 0.9303 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\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 5892 _diffrn_reflns_av_R_equivalents 0.0153 _diffrn_reflns_av_sigmaI/netI 0.0208 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.22 _diffrn_reflns_theta_max 69.14 _reflns_number_total 2778 _reflns_number_gt 2711 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0400P)^2^+0.1200P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(17) _refine_ls_number_reflns 2778 _refine_ls_number_parameters 208 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0307 _refine_ls_R_factor_gt 0.0300 _refine_ls_wR_factor_ref 0.0742 _refine_ls_wR_factor_gt 0.0735 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.038 _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 C1 C 0.7533(2) 0.41200(16) 0.95977(16) 0.0352(4) Uani 1 1 d . . . H1A H 0.6758 0.4586 0.8953 0.042 Uiso 1 1 calc R . . H1B H 0.8476 0.4695 0.9729 0.042 Uiso 1 1 calc R . . C2 C 0.69152(19) 0.40225(17) 1.08556(15) 0.0344(3) Uani 1 1 d . . . H2A H 0.7783 0.3879 1.1567 0.041 Uiso 1 1 calc R . . H2B H 0.6402 0.4902 1.1010 0.041 Uiso 1 1 calc R . . C3 C 0.57727(18) 0.28334(18) 1.08244(16) 0.0381(4) Uani 1 1 d . . . H3A H 0.4954 0.2956 1.0057 0.046 Uiso 1 1 calc R . . C4 C 0.6612(2) 0.14761(16) 1.06732(17) 0.0377(4) Uani 1 1 d . . . H4A H 0.7313 0.1261 1.1480 0.045 Uiso 1 1 calc R . . H4B H 0.5851 0.0718 1.0501 0.045 Uiso 1 1 calc R . . C5 C 0.75278(18) 0.15536(16) 0.96022(15) 0.0337(3) Uani 1 1 d . . . H5A H 0.7855 0.0712 0.9273 0.040 Uiso 1 1 calc R . . C6 C 0.79028(16) 0.27250(16) 0.90931(14) 0.0297(3) Uani 1 1 d . . . C7 C 0.86984(16) 0.27052(15) 0.79405(14) 0.0298(3) Uani 1 1 d . . . H7A H 0.8926 0.1725 0.7739 0.036 Uiso 1 1 calc R . . C8 C 0.77387(17) 0.33776(15) 0.67403(14) 0.0293(3) Uani 1 1 d . . . H8A H 0.7753 0.4401 0.6876 0.035 Uiso 1 1 calc R . . C9 C 0.85042(16) 0.30850(15) 0.56077(14) 0.0296(3) Uani 1 1 d . . . H9A H 0.8431 0.2174 0.5268 0.035 Uiso 1 1 calc R . . C10 C 0.92743(17) 0.40157(16) 0.50525(15) 0.0311(3) Uani 1 1 d . . . H10A H 0.9326 0.4930 0.5384 0.037 Uiso 1 1 calc R . . C11 C 1.00529(17) 0.37402(16) 0.39654(15) 0.0315(3) Uani 1 1 d . . . C13 C 0.60650(17) 0.29127(16) 0.65007(14) 0.0300(3) Uani 1 1 d . . . C14 C 0.56661(19) 0.15318(16) 0.62650(16) 0.0360(4) Uani 1 1 d . . . H14A H 0.6446 0.0862 0.6230 0.043 Uiso 1 1 calc R . . C15 C 0.4129(2) 0.11309(18) 0.60799(17) 0.0412(4) Uani 1 1 d . . . H15A H 0.3863 0.0190 0.5907 0.049 Uiso 1 1 calc R . . C16 C 0.2986(2) 0.2093(2) 0.61459(17) 0.0440(4) Uani 1 1 d . . . H16A H 0.1940 0.1809 0.6042 0.053 Uiso 1 1 calc R . . C17 C 0.3367(2) 0.3463(2) 0.63626(17) 0.0445(4) Uani 1 1 d . . . H17A H 0.2583 0.4129 0.6399 0.053 Uiso 1 1 calc R . . C18 C 0.48997(19) 0.38680(17) 0.65287(15) 0.0367(4) Uani 1 1 d . . . H18A H 0.5154 0.4817 0.6664 0.044 Uiso 1 1 calc R . . C19 C 1.13051(18) 0.2791(2) 0.89717(16) 0.0447(4) Uani 1 1 d . . . H19A H 1.2239 0.3359 0.9080 0.067 Uiso 1 1 calc R . . H19B H 1.1510 0.1897 0.8602 0.067 Uiso 1 1 calc R . . H19C H 1.0995 0.2644 0.9804 0.067 Uiso 1 1 calc R . . C20 C 0.5000(2) 0.2811(2) 1.2004(2) 0.0571(5) Uani 1 1 d . . . H20A H 0.4466 0.3690 1.2070 0.086 Uiso 1 1 calc R . . H20B H 0.5782 0.2678 1.2768 0.086 Uiso 1 1 calc R . . H20C H 0.4256 0.2051 1.1932 0.086 Uiso 1 1 calc R . . O2 O 0.98812(12) 0.24384(11) 0.35319(10) 0.0345(3) Uani 1 1 d . . . O1 O 1.07875(15) 0.46010(12) 0.35000(12) 0.0492(3) Uani 1 1 d . . . O3 O 1.01120(12) 0.34734(11) 0.81501(10) 0.0346(3) Uani 1 1 d . . . C12 C 1.0665(2) 0.2118(2) 0.24883(16) 0.0448(4) Uani 1 1 d . . . H12A H 1.0459 0.1154 0.2228 0.067 Uiso 1 1 calc R . . H12B H 1.1775 0.2249 0.2758 0.067 Uiso 1 1 calc R . . H12C H 1.0295 0.2731 0.1767 0.067 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 0.0415(9) 0.0293(8) 0.0358(8) -0.0022(6) 0.0092(7) -0.0022(7) C2 0.0362(8) 0.0332(8) 0.0340(8) -0.0039(6) 0.0067(7) 0.0014(7) C3 0.0333(8) 0.0426(9) 0.0393(9) -0.0024(8) 0.0092(7) -0.0024(8) C4 0.0394(9) 0.0332(8) 0.0419(9) 0.0011(7) 0.0106(8) -0.0059(7) C5 0.0349(8) 0.0302(8) 0.0356(8) -0.0032(6) 0.0050(7) -0.0001(7) C6 0.0279(7) 0.0311(7) 0.0285(7) -0.0022(6) 0.0007(6) 0.0010(6) C7 0.0304(7) 0.0268(7) 0.0328(8) -0.0018(6) 0.0068(7) 0.0003(6) C8 0.0308(7) 0.0264(7) 0.0313(8) -0.0013(6) 0.0073(6) 0.0000(6) C9 0.0277(7) 0.0294(7) 0.0308(7) -0.0007(6) 0.0026(6) 0.0019(6) C10 0.0323(8) 0.0281(7) 0.0324(8) 0.0022(6) 0.0034(7) 0.0022(6) C11 0.0302(7) 0.0302(8) 0.0335(8) 0.0064(6) 0.0036(7) 0.0003(6) C13 0.0302(7) 0.0352(8) 0.0247(7) 0.0008(6) 0.0050(6) 0.0006(7) C14 0.0331(8) 0.0346(8) 0.0399(9) -0.0023(7) 0.0052(7) -0.0002(7) C15 0.0382(9) 0.0406(9) 0.0441(10) -0.0033(7) 0.0049(8) -0.0080(8) C16 0.0302(9) 0.0570(11) 0.0436(10) -0.0036(8) 0.0031(8) -0.0064(8) C17 0.0321(8) 0.0537(10) 0.0467(10) -0.0049(9) 0.0038(8) 0.0091(8) C18 0.0370(9) 0.0355(8) 0.0374(9) -0.0029(7) 0.0053(7) 0.0016(7) C19 0.0315(8) 0.0628(11) 0.0387(9) 0.0064(9) 0.0031(7) 0.0046(8) C20 0.0584(12) 0.0532(11) 0.0682(13) -0.0048(10) 0.0355(11) -0.0060(10) O2 0.0377(6) 0.0351(6) 0.0329(6) 0.0018(4) 0.0120(5) 0.0016(5) O1 0.0589(8) 0.0411(7) 0.0532(8) 0.0071(6) 0.0253(7) -0.0077(6) O3 0.0275(5) 0.0381(6) 0.0374(6) 0.0013(5) 0.0028(5) -0.0004(5) C12 0.0509(10) 0.0482(10) 0.0393(9) 0.0038(8) 0.0196(8) 0.0120(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 C1 C6 1.508(2) . ? C1 C2 1.531(2) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.525(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C20 1.526(2) . ? C3 C4 1.529(2) . ? C3 H3A 1.0000 . ? C4 C5 1.505(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.322(2) . ? C5 H5A 0.9500 . ? C6 C7 1.5122(18) . ? C7 O3 1.4353(18) . ? C7 C8 1.549(2) . ? C7 H7A 1.0000 . ? C8 C9 1.5041(18) . ? C8 C13 1.522(2) . ? C8 H8A 1.0000 . ? C9 C10 1.325(2) . ? C9 H9A 0.9500 . ? C10 C11 1.466(2) . ? C10 H10A 0.9500 . ? C11 O1 1.2109(19) . ? C11 O2 1.3405(19) . ? C13 C18 1.386(2) . ? C13 C14 1.393(2) . ? C14 C15 1.391(2) . ? C14 H14A 0.9500 . ? C15 C16 1.382(3) . ? C15 H15A 0.9500 . ? C16 C17 1.376(3) . ? C16 H16A 0.9500 . ? C17 C18 1.389(2) . ? C17 H17A 0.9500 . ? C18 H18A 0.9500 . ? C19 O3 1.411(2) . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? O2 C12 1.4373(17) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 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 C6 C1 C2 112.73(13) . . ? C6 C1 H1A 109.0 . . ? C2 C1 H1A 109.0 . . ? C6 C1 H1B 109.0 . . ? C2 C1 H1B 109.0 . . ? H1A C1 H1B 107.8 . . ? C3 C2 C1 111.07(13) . . ? C3 C2 H2A 109.4 . . ? C1 C2 H2A 109.4 . . ? C3 C2 H2B 109.4 . . ? C1 C2 H2B 109.4 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C20 112.22(14) . . ? C2 C3 C4 108.66(12) . . ? C20 C3 C4 111.48(14) . . ? C2 C3 H3A 108.1 . . ? C20 C3 H3A 108.1 . . ? C4 C3 H3A 108.1 . . ? C5 C4 C3 111.61(12) . . ? C5 C4 H4A 109.3 . . ? C3 C4 H4A 109.3 . . ? C5 C4 H4B 109.3 . . ? C3 C4 H4B 109.3 . . ? H4A C4 H4B 108.0 . . ? C6 C5 C4 123.79(13) . . ? C6 C5 H5A 118.1 . . ? C4 C5 H5A 118.1 . . ? C5 C6 C1 122.49(12) . . ? C5 C6 C7 120.25(14) . . ? C1 C6 C7 117.24(13) . . ? O3 C7 C6 112.19(12) . . ? O3 C7 C8 104.39(11) . . ? C6 C7 C8 113.50(11) . . ? O3 C7 H7A 108.9 . . ? C6 C7 H7A 108.9 . . ? C8 C7 H7A 108.9 . . ? C9 C8 C13 111.39(12) . . ? C9 C8 C7 108.90(11) . . ? C13 C8 C7 113.07(11) . . ? C9 C8 H8A 107.8 . . ? C13 C8 H8A 107.8 . . ? C7 C8 H8A 107.8 . . ? C10 C9 C8 124.23(13) . . ? C10 C9 H9A 117.9 . . ? C8 C9 H9A 117.9 . . ? C9 C10 C11 124.89(14) . . ? C9 C10 H10A 117.6 . . ? C11 C10 H10A 117.6 . . ? O1 C11 O2 122.83(14) . . ? O1 C11 C10 123.51(15) . . ? O2 C11 C10 113.66(12) . . ? C18 C13 C14 118.54(15) . . ? C18 C13 C8 120.04(14) . . ? C14 C13 C8 121.42(14) . . ? C15 C14 C13 120.19(15) . . ? C15 C14 H14A 119.9 . . ? C13 C14 H14A 119.9 . . ? C16 C15 C14 120.41(16) . . ? C16 C15 H15A 119.8 . . ? C14 C15 H15A 119.8 . . ? C17 C16 C15 119.86(16) . . ? C17 C16 H16A 120.1 . . ? C15 C16 H16A 120.1 . . ? C16 C17 C18 119.79(17) . . ? C16 C17 H17A 120.1 . . ? C18 C17 H17A 120.1 . . ? C13 C18 C17 121.19(16) . . ? C13 C18 H18A 119.4 . . ? C17 C18 H18A 119.4 . . ? O3 C19 H19A 109.5 . . ? O3 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? O3 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C3 C20 H20A 109.5 . . ? C3 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C3 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C11 O2 C12 115.29(12) . . ? C19 O3 C7 112.95(12) . . ? O2 C12 H12A 109.5 . . ? O2 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O2 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 C6 C1 C2 C3 -42.02(19) . . . . ? C1 C2 C3 C20 -173.50(15) . . . . ? C1 C2 C3 C4 62.76(18) . . . . ? C2 C3 C4 C5 -49.18(19) . . . . ? C20 C3 C4 C5 -173.36(15) . . . . ? C3 C4 C5 C6 17.1(2) . . . . ? C4 C5 C6 C1 4.1(2) . . . . ? C4 C5 C6 C7 -174.38(15) . . . . ? C2 C1 C6 C5 8.6(2) . . . . ? C2 C1 C6 C7 -172.89(13) . . . . ? C5 C6 C7 O3 -125.19(16) . . . . ? C1 C6 C7 O3 56.28(17) . . . . ? C5 C6 C7 C8 116.77(16) . . . . ? C1 C6 C7 C8 -61.76(17) . . . . ? O3 C7 C8 C9 67.22(13) . . . . ? C6 C7 C8 C9 -170.31(12) . . . . ? O3 C7 C8 C13 -168.39(11) . . . . ? C6 C7 C8 C13 -45.92(17) . . . . ? C13 C8 C9 C10 128.25(15) . . . . ? C7 C8 C9 C10 -106.38(16) . . . . ? C8 C9 C10 C11 178.69(15) . . . . ? C9 C10 C11 O1 -177.74(16) . . . . ? C9 C10 C11 O2 2.1(2) . . . . ? C9 C8 C13 C18 -119.37(15) . . . . ? C7 C8 C13 C18 117.61(15) . . . . ? C9 C8 C13 C14 61.38(19) . . . . ? C7 C8 C13 C14 -61.65(19) . . . . ? C18 C13 C14 C15 -0.8(3) . . . . ? C8 C13 C14 C15 178.43(14) . . . . ? C13 C14 C15 C16 -0.9(3) . . . . ? C14 C15 C16 C17 1.7(3) . . . . ? C15 C16 C17 C18 -0.7(3) . . . . ? C14 C13 C18 C17 1.8(3) . . . . ? C8 C13 C18 C17 -177.46(15) . . . . ? C16 C17 C18 C13 -1.0(3) . . . . ? O1 C11 O2 C12 1.5(2) . . . . ? C10 C11 O2 C12 -178.33(13) . . . . ? C6 C7 O3 C19 73.41(15) . . . . ? C8 C7 O3 C19 -163.27(12) . . . . ? _diffrn_measured_fraction_theta_max 0.923 _diffrn_reflns_theta_full 69.14 _diffrn_measured_fraction_theta_full 0.923 _refine_diff_density_max 0.110 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.038