data_leo239 _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H22 O5' _chemical_formula_weight 330.37 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 Pbca 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' '-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 5.9275(2) _cell_length_b 22.3693(8) _cell_length_c 25.6873(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3406.0(2) _cell_formula_units_Z 8 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 9942 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.07 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1408 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9652 _exptl_absorpt_correction_T_max 0.9932 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(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 38193 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_sigmaI/netI 0.0170 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -30 _diffrn_reflns_limit_k_max 29 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.89 _reflns_number_total 4309 _reflns_number_gt 3623 _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^)+(0.0489P)^2^+1.2455P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4309 _refine_ls_number_parameters 305 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0456 _refine_ls_R_factor_gt 0.0361 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0901 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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 -0.16950(13) 0.28006(4) 0.04343(3) 0.02263(18) Uani 1 1 d . . . O2 O -0.06864(12) 0.30165(3) 0.12504(3) 0.01787(16) Uani 1 1 d . . . O3 O 0.12159(13) 0.23566(3) 0.17862(3) 0.01969(17) Uani 1 1 d . . . O4 O 0.53609(14) 0.35982(3) 0.20810(3) 0.02160(18) Uani 1 1 d . . . O5 O 0.66046(12) 0.43358(3) 0.15549(3) 0.01736(16) Uani 1 1 d . . . C1 C -0.02088(18) 0.28907(4) 0.07423(4) 0.0167(2) Uani 1 1 d . . . C2 C 0.23215(17) 0.28872(5) 0.06535(4) 0.0168(2) Uani 1 1 d . . . C3 C 0.12925(17) 0.29281(4) 0.15726(4) 0.0154(2) Uani 1 1 d . . . C4 C 0.44195(16) 0.35716(4) 0.11834(4) 0.0147(2) Uani 1 1 d . . . C5 C 0.43484(17) 0.38123(5) 0.07107(4) 0.0168(2) Uani 1 1 d . . . C6 C 0.32413(18) 0.34149(5) 0.03134(4) 0.0182(2) Uani 1 1 d . . . C7 C 0.33205(17) 0.29649(4) 0.12041(4) 0.0151(2) Uani 1 1 d . . . C8 C -0.0614(2) 0.22886(6) 0.21470(5) 0.0258(2) Uani 1 1 d . . . C9 C 0.54912(17) 0.38242(5) 0.16528(4) 0.0158(2) Uani 1 1 d . . . C10 C 0.7582(2) 0.46236(5) 0.20114(4) 0.0212(2) Uani 1 1 d . . . C11 C 0.91627(18) 0.51006(5) 0.18232(4) 0.0169(2) Uani 1 1 d . . . C12 C 1.11161(19) 0.49433(5) 0.15550(4) 0.0218(2) Uani 1 1 d . . . C13 C 1.2619(2) 0.53783(5) 0.13872(5) 0.0246(2) Uani 1 1 d . . . C14 C 1.2182(2) 0.59776(5) 0.14881(4) 0.0234(2) Uani 1 1 d . . . C15 C 1.0246(2) 0.61366(5) 0.17544(5) 0.0243(2) Uani 1 1 d . . . C16 C 0.87355(19) 0.57015(5) 0.19228(4) 0.0214(2) Uani 1 1 d . . . C17 C 0.15864(19) 0.37382(6) -0.00553(4) 0.0229(2) Uani 1 1 d . . . C18 C 0.2908(2) 0.40740(8) -0.04763(5) 0.0360(3) Uani 1 1 d . . . C19 C 0.0019(2) 0.41725(6) 0.02279(5) 0.0269(3) Uani 1 1 d . . . H2A H 0.268(2) 0.2505(6) 0.0490(5) 0.021(3) Uiso 1 1 d . . . H3A H 0.122(2) 0.3236(5) 0.1849(5) 0.011(3) Uiso 1 1 d . . . H5A H 0.501(2) 0.4198(6) 0.0630(5) 0.019(3) Uiso 1 1 d . . . H6A H 0.448(2) 0.3239(6) 0.0091(5) 0.022(3) Uiso 1 1 d . . . H7A H 0.440(2) 0.2661(6) 0.1302(5) 0.020(3) Uiso 1 1 d . . . H8A H -0.046(2) 0.1881(7) 0.2289(6) 0.032(4) Uiso 1 1 d . . . H8B H -0.205(3) 0.2340(7) 0.1966(6) 0.036(4) Uiso 1 1 d . . . H8C H -0.047(2) 0.2586(6) 0.2438(6) 0.030(4) Uiso 1 1 d . . . H10A H 0.837(2) 0.4303(7) 0.2220(6) 0.030(4) Uiso 1 1 d . . . H10B H 0.637(2) 0.4792(6) 0.2213(6) 0.027(4) Uiso 1 1 d . . . H12A H 1.139(3) 0.4517(7) 0.1477(6) 0.034(4) Uiso 1 1 d . . . H13A H 1.396(3) 0.5265(7) 0.1209(6) 0.035(4) Uiso 1 1 d . . . H14A H 1.319(3) 0.6282(7) 0.1378(6) 0.031(4) Uiso 1 1 d . . . H15A H 0.991(3) 0.6554(7) 0.1825(6) 0.036(4) Uiso 1 1 d . . . H16A H 0.738(3) 0.5802(7) 0.2107(5) 0.029(4) Uiso 1 1 d . . . H17A H 0.068(2) 0.3428(7) -0.0230(6) 0.029(4) Uiso 1 1 d . . . H18A H 0.380(3) 0.3793(8) -0.0666(7) 0.045(5) Uiso 1 1 d . . . H18B H 0.392(3) 0.4390(7) -0.0314(6) 0.037(4) Uiso 1 1 d . . . H18C H 0.190(3) 0.4289(8) -0.0715(7) 0.045(5) Uiso 1 1 d . . . H19A H 0.091(3) 0.4528(7) 0.0360(6) 0.034(4) Uiso 1 1 d . . . H19B H -0.075(3) 0.3991(7) 0.0535(6) 0.036(4) Uiso 1 1 d . . . H19C H -0.116(3) 0.4322(7) -0.0016(7) 0.042(4) Uiso 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 O1 0.0186(4) 0.0266(4) 0.0227(4) -0.0044(3) -0.0040(3) -0.0024(3) O2 0.0145(3) 0.0224(4) 0.0167(3) 0.0000(3) 0.0004(3) 0.0013(3) O3 0.0223(4) 0.0163(4) 0.0205(4) 0.0031(3) 0.0002(3) -0.0020(3) O4 0.0248(4) 0.0241(4) 0.0159(4) 0.0023(3) -0.0012(3) -0.0067(3) O5 0.0195(4) 0.0179(4) 0.0146(3) -0.0005(3) -0.0018(3) -0.0047(3) C1 0.0175(5) 0.0142(4) 0.0184(5) -0.0017(4) 0.0002(4) -0.0003(4) C2 0.0157(5) 0.0181(5) 0.0165(5) -0.0048(4) 0.0002(4) 0.0012(4) C3 0.0154(5) 0.0147(5) 0.0160(5) -0.0004(4) -0.0012(4) -0.0010(4) C4 0.0114(4) 0.0158(5) 0.0169(5) -0.0020(4) 0.0004(4) 0.0002(3) C5 0.0127(5) 0.0206(5) 0.0171(5) -0.0009(4) 0.0010(4) 0.0004(4) C6 0.0149(5) 0.0253(5) 0.0144(5) -0.0020(4) 0.0016(4) -0.0004(4) C7 0.0139(5) 0.0150(5) 0.0166(5) -0.0019(4) -0.0007(4) 0.0012(4) C8 0.0249(6) 0.0283(6) 0.0241(6) 0.0065(5) 0.0017(5) -0.0084(5) C9 0.0132(4) 0.0170(5) 0.0173(5) -0.0007(4) 0.0009(4) 0.0002(4) C10 0.0255(6) 0.0240(5) 0.0141(5) -0.0029(4) -0.0004(4) -0.0090(4) C11 0.0183(5) 0.0187(5) 0.0137(4) -0.0007(4) -0.0021(4) -0.0032(4) C12 0.0228(5) 0.0170(5) 0.0258(5) -0.0008(4) 0.0019(4) 0.0019(4) C13 0.0191(5) 0.0257(6) 0.0290(6) 0.0000(5) 0.0051(5) 0.0007(4) C14 0.0240(5) 0.0217(5) 0.0245(5) 0.0007(4) 0.0008(4) -0.0073(4) C15 0.0311(6) 0.0164(5) 0.0253(5) -0.0037(4) 0.0017(5) -0.0013(4) C16 0.0212(5) 0.0222(5) 0.0209(5) -0.0050(4) 0.0027(4) 0.0004(4) C17 0.0192(5) 0.0330(6) 0.0165(5) 0.0033(4) -0.0027(4) -0.0037(5) C18 0.0303(7) 0.0571(9) 0.0207(6) 0.0130(6) -0.0012(5) -0.0074(7) C19 0.0207(6) 0.0277(6) 0.0324(6) 0.0085(5) -0.0025(5) 0.0016(5) _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 1.2010(13) . ? O2 C1 1.3650(12) . ? O2 C3 1.4490(12) . ? O3 C3 1.3920(12) . ? O3 C8 1.4349(14) . ? O4 C9 1.2129(12) . ? O5 C9 1.3450(12) . ? O5 C10 1.4578(12) . ? C1 C2 1.5171(14) . ? C2 C7 1.5432(14) . ? C2 C6 1.5665(15) . ? C2 H2A 0.977(13) . ? C3 C7 1.5322(14) . ? C3 H3A 0.988(12) . ? C4 C5 1.3289(14) . ? C4 C9 1.4755(14) . ? C4 C7 1.5063(14) . ? C5 C6 1.5040(14) . ? C5 H5A 0.968(13) . ? C6 C17 1.5434(15) . ? C6 H6A 1.009(14) . ? C7 H7A 0.968(14) . ? C8 H8A 0.986(15) . ? C8 H8B 0.975(17) . ? C8 H8C 1.004(15) . ? C10 C11 1.5002(15) . ? C10 H10A 1.010(15) . ? C10 H10B 0.960(15) . ? C11 C16 1.3916(15) . ? C11 C12 1.3925(15) . ? C12 C13 1.3879(16) . ? C12 H12A 0.987(15) . ? C13 C14 1.3898(17) . ? C13 H13A 0.953(16) . ? C14 C15 1.3825(17) . ? C14 H14A 0.948(16) . ? C15 C16 1.3916(16) . ? C15 H15A 0.971(16) . ? C16 H16A 0.961(15) . ? C17 C19 1.5286(17) . ? C17 C18 1.5322(17) . ? C17 H17A 0.984(15) . ? C18 H18A 0.956(18) . ? C18 H18B 1.016(17) . ? C18 H18C 0.982(18) . ? C19 H19A 1.011(16) . ? C19 H19B 0.999(16) . ? C19 H19C 0.997(17) . ? 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 O2 C3 110.49(8) . . ? C3 O3 C8 112.13(8) . . ? C9 O5 C10 114.84(8) . . ? O1 C1 O2 120.82(9) . . ? O1 C1 C2 128.70(10) . . ? O2 C1 C2 110.48(8) . . ? C1 C2 C7 103.94(8) . . ? C1 C2 C6 115.09(9) . . ? C7 C2 C6 107.02(8) . . ? C1 C2 H2A 106.6(8) . . ? C7 C2 H2A 114.1(8) . . ? C6 C2 H2A 110.2(8) . . ? O3 C3 O2 108.91(8) . . ? O3 C3 C7 108.57(8) . . ? O2 C3 C7 105.96(8) . . ? O3 C3 H3A 110.8(7) . . ? O2 C3 H3A 106.3(7) . . ? C7 C3 H3A 116.0(7) . . ? C5 C4 C9 127.26(9) . . ? C5 C4 C7 112.56(9) . . ? C9 C4 C7 120.15(9) . . ? C4 C5 C6 113.23(9) . . ? C4 C5 H5A 122.9(8) . . ? C6 C5 H5A 123.8(8) . . ? C5 C6 C17 114.63(9) . . ? C5 C6 C2 102.64(8) . . ? C17 C6 C2 118.30(9) . . ? C5 C6 H6A 107.2(8) . . ? C17 C6 H6A 107.3(8) . . ? C2 C6 H6A 106.0(8) . . ? C4 C7 C3 114.18(8) . . ? C4 C7 C2 103.59(8) . . ? C3 C7 C2 105.02(8) . . ? C4 C7 H7A 110.8(8) . . ? C3 C7 H7A 108.8(8) . . ? C2 C7 H7A 114.5(8) . . ? O3 C8 H8A 105.3(9) . . ? O3 C8 H8B 109.8(9) . . ? H8A C8 H8B 111.6(13) . . ? O3 C8 H8C 110.2(9) . . ? H8A C8 H8C 109.3(12) . . ? H8B C8 H8C 110.5(12) . . ? O4 C9 O5 123.75(9) . . ? O4 C9 C4 123.65(9) . . ? O5 C9 C4 112.59(8) . . ? O5 C10 C11 107.64(8) . . ? O5 C10 H10A 107.3(8) . . ? C11 C10 H10A 112.6(8) . . ? O5 C10 H10B 108.1(9) . . ? C11 C10 H10B 111.1(9) . . ? H10A C10 H10B 109.9(12) . . ? C16 C11 C12 119.10(10) . . ? C16 C11 C10 120.94(10) . . ? C12 C11 C10 119.95(10) . . ? C13 C12 C11 120.69(10) . . ? C13 C12 H12A 120.4(9) . . ? C11 C12 H12A 118.9(9) . . ? C12 C13 C14 119.91(11) . . ? C12 C13 H13A 120.0(10) . . ? C14 C13 H13A 120.1(10) . . ? C15 C14 C13 119.69(11) . . ? C15 C14 H14A 119.0(9) . . ? C13 C14 H14A 121.3(9) . . ? C14 C15 C16 120.52(10) . . ? C14 C15 H15A 120.5(9) . . ? C16 C15 H15A 118.9(9) . . ? C15 C16 C11 120.09(10) . . ? C15 C16 H16A 121.9(9) . . ? C11 C16 H16A 118.0(9) . . ? C19 C17 C18 109.58(11) . . ? C19 C17 C6 113.09(9) . . ? C18 C17 C6 109.75(10) . . ? C19 C17 H17A 109.5(9) . . ? C18 C17 H17A 107.5(8) . . ? C6 C17 H17A 107.2(9) . . ? C17 C18 H18A 108.8(10) . . ? C17 C18 H18B 110.6(9) . . ? H18A C18 H18B 110.0(14) . . ? C17 C18 H18C 111.6(10) . . ? H18A C18 H18C 110.0(14) . . ? H18B C18 H18C 105.9(13) . . ? C17 C19 H19A 110.0(9) . . ? C17 C19 H19B 113.4(9) . . ? H19A C19 H19B 107.0(12) . . ? C17 C19 H19C 109.8(10) . . ? H19A C19 H19C 108.1(13) . . ? H19B C19 H19C 108.2(13) . . ? 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 C3 O2 C1 O1 162.59(9) . . . . ? C3 O2 C1 C2 -17.34(11) . . . . ? O1 C1 C2 C7 -174.07(11) . . . . ? O2 C1 C2 C7 5.85(11) . . . . ? O1 C1 C2 C6 69.23(14) . . . . ? O2 C1 C2 C6 -110.84(10) . . . . ? C8 O3 C3 O2 -66.41(10) . . . . ? C8 O3 C3 C7 178.65(8) . . . . ? C1 O2 C3 O3 -95.25(9) . . . . ? C1 O2 C3 C7 21.38(10) . . . . ? C9 C4 C5 C6 176.35(9) . . . . ? C7 C4 C5 C6 -1.32(12) . . . . ? C4 C5 C6 C17 136.54(10) . . . . ? C4 C5 C6 C2 6.94(11) . . . . ? C1 C2 C6 C5 105.32(10) . . . . ? C7 C2 C6 C5 -9.61(10) . . . . ? C1 C2 C6 C17 -21.97(13) . . . . ? C7 C2 C6 C17 -136.90(9) . . . . ? C5 C4 C7 C3 -118.67(10) . . . . ? C9 C4 C7 C3 63.48(12) . . . . ? C5 C4 C7 C2 -5.04(11) . . . . ? C9 C4 C7 C2 177.10(9) . . . . ? O3 C3 C7 C4 -146.98(8) . . . . ? O2 C3 C7 C4 96.17(9) . . . . ? O3 C3 C7 C2 100.24(9) . . . . ? O2 C3 C7 C2 -16.61(10) . . . . ? C1 C2 C7 C4 -113.20(9) . . . . ? C6 C2 C7 C4 9.00(10) . . . . ? C1 C2 C7 C3 6.88(10) . . . . ? C6 C2 C7 C3 129.08(8) . . . . ? C10 O5 C9 O4 -2.77(14) . . . . ? C10 O5 C9 C4 176.48(9) . . . . ? C5 C4 C9 O4 174.86(10) . . . . ? C7 C4 C9 O4 -7.63(15) . . . . ? C5 C4 C9 O5 -4.39(15) . . . . ? C7 C4 C9 O5 173.11(8) . . . . ? C9 O5 C10 C11 167.66(9) . . . . ? O5 C10 C11 C16 115.07(11) . . . . ? O5 C10 C11 C12 -66.41(13) . . . . ? C16 C11 C12 C13 -0.17(17) . . . . ? C10 C11 C12 C13 -178.72(10) . . . . ? C11 C12 C13 C14 0.19(18) . . . . ? C12 C13 C14 C15 -0.16(18) . . . . ? C13 C14 C15 C16 0.12(18) . . . . ? C14 C15 C16 C11 -0.10(18) . . . . ? C12 C11 C16 C15 0.13(17) . . . . ? C10 C11 C16 C15 178.66(10) . . . . ? C5 C6 C17 C19 -44.48(13) . . . . ? C2 C6 C17 C19 76.88(12) . . . . ? C5 C6 C17 C18 78.21(13) . . . . ? C2 C6 C17 C18 -160.44(10) . . . . ? _diffrn_measured_fraction_theta_max 0.965 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.347 _refine_diff_density_min -0.226 _refine_diff_density_rms 0.042