data_ar072 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H26 O4' _chemical_formula_weight 330.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 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 P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 10.375(2) _cell_length_b 11.449(3) _cell_length_c 15.153(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1799.9(8) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.219 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8732 _diffrn_reflns_av_R_equivalents 0.0268 _diffrn_reflns_av_sigmaI/netI 0.0259 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 23.29 _reflns_number_total 2594 _reflns_number_gt 2120 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0506P)^2^+0.0000P] 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 -0.3(13) _refine_ls_number_reflns 2594 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0468 _refine_ls_R_factor_gt 0.0344 _refine_ls_wR_factor_ref 0.0849 _refine_ls_wR_factor_gt 0.0802 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _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 0.05746(17) 0.98879(16) 0.62312(11) 0.0476(5) Uani 1 1 d . . . C2 C 0.0911(2) 1.09667(17) 0.57001(13) 0.0568(5) Uani 1 1 d . . . C3 C -0.0116(2) 1.16347(19) 0.52160(14) 0.0675(6) Uani 1 1 d . . . H3A H -0.0093 1.2440 0.5435 0.081 Uiso 1 1 calc R . . C4 C -0.1471(2) 1.1162(2) 0.53897(16) 0.0824(7) Uani 1 1 d . . . H4A H -0.2105 1.1737 0.5210 0.099 Uiso 1 1 calc R . . H4B H -0.1608 1.0460 0.5044 0.099 Uiso 1 1 calc R . . C5 C -0.1642(2) 1.0888(2) 0.63530(16) 0.0790(7) Uani 1 1 d . . . H5A H -0.2541 1.0714 0.6470 0.095 Uiso 1 1 calc R . . H5B H -0.1403 1.1565 0.6702 0.095 Uiso 1 1 calc R . . C6 C -0.08146(18) 0.98505(18) 0.66224(13) 0.0566(5) Uani 1 1 d . . . H6A H -0.1235 0.9141 0.6403 0.068 Uiso 1 1 calc R . . C7 C -0.06079(19) 0.9705(2) 0.76144(13) 0.0654(6) Uani 1 1 d . . . H7A H -0.0487 1.0483 0.7871 0.078 Uiso 1 1 calc R . . C8 C 0.0666(2) 0.9057(2) 0.76734(13) 0.0640(6) Uani 1 1 d . . . H8A H 0.0553 0.8237 0.7535 0.077 Uiso 1 1 calc R . . H8B H 0.1032 0.9125 0.8260 0.077 Uiso 1 1 calc R . . C9 C 0.15248(17) 0.96491(18) 0.69936(11) 0.0485(5) Uani 1 1 d . . . H9A H 0.1866 1.0385 0.7228 0.058 Uiso 1 1 calc R . . C10 C 0.26308(17) 0.88715(18) 0.66496(12) 0.0505(5) Uani 1 1 d . . . H10A H 0.2714 0.8204 0.7051 0.061 Uiso 1 1 calc R . . C11 C 0.40001(19) 0.94226(17) 0.65293(13) 0.0557(5) Uani 1 1 d . . . C19 C 0.4279(2) 1.0477(2) 0.71120(16) 0.0777(7) Uani 1 1 d . . . H19A H 0.5134 1.0757 0.6995 0.117 Uiso 1 1 calc R . . H19B H 0.4212 1.0254 0.7721 0.117 Uiso 1 1 calc R . . H19C H 0.3667 1.1083 0.6987 0.117 Uiso 1 1 calc R . . C18 C 0.50142(19) 0.8468(2) 0.66958(16) 0.0767(7) Uani 1 1 d . . . H18A H 0.5861 0.8791 0.6624 0.115 Uiso 1 1 calc R . . H18B H 0.4893 0.7842 0.6282 0.115 Uiso 1 1 calc R . . H18C H 0.4921 0.8173 0.7286 0.115 Uiso 1 1 calc R . . C15 C 0.08426(19) 0.88858(17) 0.55904(13) 0.0566(5) Uani 1 1 d . . . C14 C 0.21905(18) 0.83978(17) 0.57352(12) 0.0513(5) Uani 1 1 d . . . C13 C 0.3091(2) 0.89598(19) 0.50640(15) 0.0633(6) Uani 1 1 d . . . C12 C 0.4106(2) 0.96809(18) 0.55644(14) 0.0629(6) Uani 1 1 d . . . C16 C 0.0191(3) 1.1675(3) 0.42335(17) 0.1050(9) Uani 1 1 d . . . H16A H 0.1046 1.1975 0.4149 0.158 Uiso 1 1 calc R . . H16B H -0.0418 1.2174 0.3940 0.158 Uiso 1 1 calc R . . H16C H 0.0137 1.0902 0.3991 0.158 Uiso 1 1 calc R . . C17 C -0.1724(2) 0.9119(3) 0.80922(18) 0.0987(9) Uani 1 1 d . . . H17A H -0.1527 0.9058 0.8709 0.148 Uiso 1 1 calc R . . H17B H -0.1858 0.8353 0.7852 0.148 Uiso 1 1 calc R . . H17C H -0.2491 0.9577 0.8016 0.148 Uiso 1 1 calc R . . C20 C 0.2175(2) 0.70689(18) 0.56152(16) 0.0732(6) Uani 1 1 d . . . H20A H 0.1888 0.6883 0.5029 0.110 Uiso 1 1 calc R . . H20B H 0.1598 0.6726 0.6038 0.110 Uiso 1 1 calc R . . H20C H 0.3027 0.6765 0.5703 0.110 Uiso 1 1 calc R . . O1 O 0.20429(15) 1.12473(15) 0.56411(11) 0.0826(5) Uani 1 1 d . . . O2 O 0.30423(18) 0.88438(19) 0.42805(11) 0.1035(6) Uani 1 1 d . . . O3 O 0.48888(16) 1.02903(17) 0.51964(11) 0.0942(6) Uani 1 1 d . . . O4 O 0.01014(15) 0.85244(15) 0.50487(12) 0.0932(6) 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 0.0503(11) 0.0460(11) 0.0463(10) -0.0027(9) -0.0022(8) 0.0003(9) C2 0.0610(14) 0.0557(12) 0.0537(12) -0.0039(10) -0.0032(10) -0.0003(11) C3 0.0805(16) 0.0528(13) 0.0694(15) 0.0047(11) -0.0122(12) 0.0102(12) C4 0.0722(16) 0.0795(18) 0.0954(19) 0.0053(14) -0.0201(13) 0.0190(14) C5 0.0597(13) 0.0798(18) 0.0974(19) 0.0016(15) 0.0005(13) 0.0166(13) C6 0.0471(11) 0.0554(13) 0.0674(13) -0.0051(11) -0.0001(10) -0.0037(10) C7 0.0555(13) 0.0762(15) 0.0646(13) -0.0047(11) 0.0108(10) -0.0008(11) C8 0.0635(13) 0.0761(15) 0.0523(12) 0.0061(11) 0.0042(10) 0.0011(12) C9 0.0494(10) 0.0521(12) 0.0441(11) -0.0010(9) -0.0016(9) -0.0007(9) C10 0.0516(11) 0.0512(12) 0.0486(11) 0.0034(9) 0.0009(9) 0.0031(10) C11 0.0464(11) 0.0619(13) 0.0588(12) -0.0039(10) -0.0049(10) 0.0015(10) C19 0.0556(13) 0.0857(17) 0.0918(17) -0.0204(14) -0.0048(13) -0.0097(13) C18 0.0554(13) 0.0964(19) 0.0784(16) -0.0105(13) -0.0097(11) 0.0129(13) C15 0.0532(12) 0.0572(12) 0.0594(13) -0.0093(11) -0.0050(11) -0.0029(11) C14 0.0507(11) 0.0492(12) 0.0542(12) -0.0065(10) 0.0043(10) -0.0003(9) C13 0.0640(13) 0.0757(16) 0.0502(13) 0.0020(12) 0.0017(10) 0.0012(12) C12 0.0496(11) 0.0666(13) 0.0725(14) 0.0088(12) 0.0098(11) -0.0027(12) C16 0.123(2) 0.126(2) 0.0657(16) 0.0233(15) -0.0164(16) 0.011(2) C17 0.0700(15) 0.136(2) 0.0904(19) 0.0165(16) 0.0244(14) -0.0024(17) C20 0.0671(14) 0.0562(14) 0.0963(17) -0.0159(12) 0.0133(13) -0.0003(11) O1 0.0668(11) 0.0848(11) 0.0961(12) 0.0355(9) -0.0015(9) -0.0100(9) O2 0.1071(14) 0.1483(18) 0.0550(11) -0.0036(10) 0.0084(9) -0.0243(13) O3 0.0723(11) 0.1085(14) 0.1018(13) 0.0126(11) 0.0181(10) -0.0229(10) O4 0.0736(10) 0.1018(13) 0.1043(13) -0.0511(11) -0.0308(10) 0.0133(9) _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 C2 1.515(3) . ? C1 C15 1.529(3) . ? C1 C9 1.543(2) . ? C1 C6 1.559(3) . ? C2 O1 1.220(2) . ? C2 C3 1.503(3) . ? C3 C16 1.523(3) . ? C3 C4 1.530(3) . ? C3 H3A 0.9800 . ? C4 C5 1.503(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.522(3) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.527(3) . ? C6 H6A 0.9800 . ? C7 C17 1.522(3) . ? C7 C8 1.518(3) . ? C7 H7A 0.9800 . ? C8 C9 1.521(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.543(3) . ? C9 H9A 0.9800 . ? C10 C14 1.557(3) . ? C10 C11 1.565(3) . ? C10 H10A 0.9800 . ? C11 C12 1.496(3) . ? C11 C19 1.523(3) . ? C11 C18 1.538(3) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C15 O4 1.198(2) . ? C15 C14 1.522(3) . ? C14 C13 1.524(3) . ? C14 C20 1.532(3) . ? C13 O2 1.196(2) . ? C13 C12 1.538(3) . ? C12 O3 1.207(2) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? 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 C2 C1 C15 103.44(14) . . ? C2 C1 C9 113.25(16) . . ? C15 C1 C9 103.08(15) . . ? C2 C1 C6 115.96(16) . . ? C15 C1 C6 112.90(15) . . ? C9 C1 C6 107.52(14) . . ? O1 C2 C3 120.82(19) . . ? O1 C2 C1 118.39(18) . . ? C3 C2 C1 120.70(18) . . ? C2 C3 C16 110.2(2) . . ? C2 C3 C4 112.82(18) . . ? C16 C3 C4 111.8(2) . . ? C2 C3 H3A 107.3 . . ? C16 C3 H3A 107.3 . . ? C4 C3 H3A 107.3 . . ? C5 C4 C3 110.4(2) . . ? C5 C4 H4A 109.6 . . ? C3 C4 H4A 109.6 . . ? C5 C4 H4B 109.6 . . ? C3 C4 H4B 109.6 . . ? H4A C4 H4B 108.1 . . ? C4 C5 C6 110.91(19) . . ? C4 C5 H5A 109.5 . . ? C6 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? C6 C5 H5B 109.5 . . ? H5A C5 H5B 108.0 . . ? C5 C6 C7 115.35(18) . . ? C5 C6 C1 113.45(17) . . ? C7 C6 C1 104.32(15) . . ? C5 C6 H6A 107.8 . . ? C7 C6 H6A 107.8 . . ? C1 C6 H6A 107.8 . . ? C17 C7 C8 114.8(2) . . ? C17 C7 C6 114.16(19) . . ? C8 C7 C6 103.50(16) . . ? C17 C7 H7A 108.0 . . ? C8 C7 H7A 108.0 . . ? C6 C7 H7A 108.0 . . ? C7 C8 C9 104.61(16) . . ? C7 C8 H8A 110.8 . . ? C9 C8 H8A 110.8 . . ? C7 C8 H8B 110.8 . . ? C9 C8 H8B 110.8 . . ? H8A C8 H8B 108.9 . . ? C8 C9 C10 114.04(16) . . ? C8 C9 C1 102.22(15) . . ? C10 C9 C1 108.94(14) . . ? C8 C9 H9A 110.4 . . ? C10 C9 H9A 110.4 . . ? C1 C9 H9A 110.4 . . ? C9 C10 C14 106.46(14) . . ? C9 C10 C11 118.81(17) . . ? C14 C10 C11 107.65(15) . . ? C9 C10 H10A 107.8 . . ? C14 C10 H10A 107.8 . . ? C11 C10 H10A 107.8 . . ? C12 C11 C19 113.33(18) . . ? C12 C11 C18 104.50(17) . . ? C19 C11 C18 109.76(17) . . ? C12 C11 C10 105.10(15) . . ? C19 C11 C10 115.11(17) . . ? C18 C11 C10 108.37(17) . . ? C11 C19 H19A 109.5 . . ? C11 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C11 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C11 C18 H18A 109.5 . . ? C11 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C11 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? O4 C15 C14 124.17(18) . . ? O4 C15 C1 125.27(18) . . ? C14 C15 C1 110.56(16) . . ? C15 C14 C13 108.21(17) . . ? C15 C14 C20 109.72(16) . . ? C13 C14 C20 110.29(17) . . ? C15 C14 C10 105.67(15) . . ? C13 C14 C10 105.48(16) . . ? C20 C14 C10 117.05(18) . . ? O2 C13 C14 126.1(2) . . ? O2 C13 C12 125.3(2) . . ? C14 C13 C12 108.52(17) . . ? O3 C12 C11 128.0(2) . . ? O3 C12 C13 122.9(2) . . ? C11 C12 C13 108.98(17) . . ? C3 C16 H16A 109.5 . . ? C3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C7 C17 H17A 109.5 . . ? C7 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C7 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C14 C20 H20A 109.5 . . ? C14 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C14 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.29 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.084 _refine_diff_density_min -0.096 _refine_diff_density_rms 0.022