data_m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 O5' _chemical_formula_weight 240.25 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 P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.4888(5) _cell_length_b 15.2345(11) _cell_length_c 10.0221(5) _cell_angle_alpha 90.000 _cell_angle_beta 98.888(5) _cell_angle_gamma 90.000 _cell_volume 1129.67(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9.1900 _cell_measurement_theta_max 12.430 _exptl_crystal_description cube _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35mm _exptl_crystal_size_mid 0.30mm _exptl_crystal_size_min 0.20mm _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.413 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type 'psi-scan' _exptl_absorpt_correction_T_min 0.851 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ; psi-scan (North, Philips & Mathews, 1968) ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type ' MoK\a' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type Enraf-Nonius_CAD-4 _diffrn_measurement_method \w/q-scan _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 3600 _diffrn_standards_decay_% '<3%' _diffrn_reflns_number 1875 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0112 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.45 _diffrn_reflns_theta_max 25.01 _reflns_number_total 1875 _reflns_number_gt 1727 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Enraf Nonius CAD4, 1989' _computing_cell_refinement 'Enraf Nonius CAD4, 1989' _computing_data_reduction 'maXus (Mackay et al., 1999)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ZORTEP (Zsolnai, L and Pritzkow, H, 1994)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.1047P)^2^+0.2439P] 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 1875 _refine_ls_number_parameters 220 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0571 _refine_ls_R_factor_gt 0.0539 _refine_ls_wR_factor_ref 0.1524 _refine_ls_wR_factor_gt 0.1481 _refine_ls_goodness_of_fit_ref 1.134 _refine_ls_restrained_S_all 1.134 _refine_ls_shift/su_max 0.001 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.2672(4) 0.03624(19) 0.6138(3) 0.0626(7) Uani 1 d . . . C2 C -0.0766(3) 0.05690(15) 0.6738(3) 0.0502(6) Uani 1 d . . . C3 C 0.1485(3) 0.16717(13) 0.6692(2) 0.0384(5) Uani 1 d . . . C4 C 0.3538(2) 0.29450(13) 0.6620(2) 0.0378(5) Uani 1 d . . . C5 C 0.1490(3) 0.27550(13) 0.83734(19) 0.0375(5) Uani 1 d . . . C6 C 0.0271(2) 0.31860(13) 0.60821(19) 0.0369(5) Uani 1 d . . . C7 C 0.1116(3) 0.41099(13) 0.6234(2) 0.0410(5) Uani 1 d . . . C8 C 0.2970(2) 0.33361(12) 0.79096(19) 0.0367(5) Uani 1 d . . . C9 C 0.1795(2) 0.25047(13) 0.59296(19) 0.0362(5) Uani 1 d . . . C10 C 0.4078(3) 0.36785(15) 0.5730(2) 0.0479(6) Uani 1 d . . . C11 C 0.2435(3) 0.42602(16) 0.5256(2) 0.0517(6) Uani 1 d . . . C16 C -0.0234(2) 0.30203(12) 0.7450(2) 0.0376(5) Uani 1 d . . . O1 O -0.02994(18) 0.14077(9) 0.62432(13) 0.0412(4) Uani 1 d . . . O2 O 0.17681(18) 0.18423(9) 0.81174(13) 0.0419(4) Uani 1 d . . . O4 O 0.21310(18) 0.41736(8) 0.75866(13) 0.0407(4) Uani 1 d . . . O3 O -0.17016(19) 0.31014(11) 0.78000(17) 0.0542(5) Uani 1 d . . . O5 O 0.4910(2) 0.23036(11) 0.69095(19) 0.0555(5) Uani 1 d . . . H1 H -0.344(6) 0.081(3) 0.645(4) 0.123(15) Uiso 1 d . . . H1A H -0.296(5) -0.021(3) 0.644(3) 0.096(10) Uiso 1 d . . . H1B H -0.275(5) 0.034(2) 0.512(4) 0.097(11) Uiso 1 d . . . H2A H -0.058(4) 0.0571(19) 0.776(3) 0.073(8) Uiso 1 d . . . H2B H 0.012(4) 0.013(2) 0.648(3) 0.077(9) Uiso 1 d . . . H3 H 0.229(3) 0.1226(14) 0.6625(19) 0.035(5) Uiso 1 d . . . H4 H 0.588(6) 0.259(2) 0.711(4) 0.096(12) Uiso 1 d . . . H5 H 0.143(3) 0.2827(14) 0.930(2) 0.038(5) Uiso 1 d . . . H6 H -0.079(4) 0.3191(15) 0.537(3) 0.052(6) Uiso 1 d . . . H7 H 0.019(3) 0.4564(14) 0.618(2) 0.039(5) Uiso 1 d . . . H8 H 0.400(3) 0.3433(15) 0.865(2) 0.042(5) Uiso 1 d . . . H9 H 0.179(3) 0.2367(14) 0.497(2) 0.043(6) Uiso 1 d . . . H10 H 0.502(4) 0.4019(18) 0.626(2) 0.059(7) Uiso 1 d . . . H10A H 0.460(4) 0.3420(16) 0.500(3) 0.054(7) Uiso 1 d . . . H11A H 0.279(3) 0.4885(19) 0.526(2) 0.055(7) Uiso 1 d . . . H11 H 0.182(4) 0.4096(18) 0.439(3) 0.069(8) Uiso 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 0.0555(15) 0.0525(14) 0.0778(18) 0.0074(13) 0.0042(12) -0.0182(12) C2 0.0483(13) 0.0396(11) 0.0610(14) 0.0064(9) 0.0026(10) -0.0053(9) C3 0.0312(10) 0.0389(10) 0.0427(11) -0.0029(8) -0.0018(7) 0.0012(8) C4 0.0238(9) 0.0427(10) 0.0461(11) -0.0015(8) 0.0026(7) 0.0027(7) C5 0.0350(10) 0.0429(11) 0.0329(10) 0.0000(7) -0.0002(7) -0.0012(8) C6 0.0239(9) 0.0456(11) 0.0376(10) 0.0038(8) -0.0064(7) 0.0007(7) C7 0.0316(10) 0.0428(11) 0.0465(11) 0.0063(8) -0.0009(8) 0.0048(8) C8 0.0273(9) 0.0411(10) 0.0383(10) -0.0005(7) -0.0055(7) -0.0019(7) C9 0.0304(9) 0.0432(10) 0.0337(10) -0.0038(8) 0.0005(7) -0.0007(8) C10 0.0376(11) 0.0535(13) 0.0554(13) 0.0003(10) 0.0157(9) -0.0043(9) C11 0.0495(13) 0.0525(13) 0.0529(13) 0.0124(10) 0.0068(10) -0.0044(10) C16 0.0271(10) 0.0378(10) 0.0471(11) -0.0020(8) 0.0032(8) -0.0014(7) O1 0.0354(8) 0.0362(7) 0.0483(8) 0.0010(6) -0.0049(6) -0.0055(5) O2 0.0412(8) 0.0407(8) 0.0402(8) 0.0053(5) -0.0054(6) -0.0002(6) O4 0.0360(7) 0.0401(8) 0.0441(8) -0.0031(6) -0.0001(6) 0.0014(6) O3 0.0305(8) 0.0630(10) 0.0715(11) -0.0036(7) 0.0159(7) -0.0002(6) O5 0.0265(8) 0.0499(9) 0.0884(13) -0.0008(8) 0.0038(7) 0.0071(7) _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 1.494(3) . ? C2 O1 1.433(2) . ? C3 O1 1.401(2) . ? C3 O2 1.435(2) . ? C3 C9 1.518(3) . ? C4 O5 1.415(2) . ? C4 C10 1.523(3) . ? C4 C9 1.534(3) . ? C4 C8 1.541(3) . ? C5 O2 1.435(2) . ? C5 C16 1.522(3) . ? C5 C8 1.545(3) . ? C6 C16 1.499(3) . ? C6 C7 1.541(3) . ? C6 C9 1.567(3) . ? C7 O4 1.451(2) . ? C7 C11 1.513(3) . ? C8 O4 1.437(2) . ? C10 C11 1.531(3) . ? C16 O3 1.210(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 O1 C2 C1 108.51(19) . . ? O1 C3 O2 111.02(16) . . ? O1 C3 C9 106.89(15) . . ? O2 C3 C9 109.84(15) . . ? O5 C4 C10 112.13(16) . . ? O5 C4 C9 109.32(16) . . ? C10 C4 C9 109.92(17) . . ? O5 C4 C8 112.38(15) . . ? C10 C4 C8 109.88(17) . . ? C9 C4 C8 102.80(14) . . ? O2 C5 C16 106.35(15) . . ? O2 C5 C8 111.76(16) . . ? C16 C5 C8 104.21(15) . . ? C16 C6 C7 102.76(15) . . ? C16 C6 C9 105.56(15) . . ? C7 C6 C9 108.71(15) . . ? O4 C7 C11 107.15(17) . . ? O4 C7 C6 107.54(14) . . ? C11 C7 C6 111.90(18) . . ? O4 C8 C4 108.79(15) . . ? O4 C8 C5 105.50(15) . . ? C4 C8 C5 109.53(15) . . ? C3 C9 C4 108.90(16) . . ? C3 C9 C6 109.54(15) . . ? C4 C9 C6 104.35(14) . . ? C4 C10 C11 109.47(16) . . ? C7 C11 C10 106.55(17) . . ? O3 C16 C6 128.06(18) . . ? O3 C16 C5 125.03(18) . . ? C6 C16 C5 106.88(15) . . ? C3 O1 C2 114.59(15) . . ? C3 O2 C5 110.51(14) . . ? C8 O4 C7 107.39(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 C16 C6 C7 O4 37.31(18) . . . . ? C9 C6 C7 O4 -74.22(19) . . . . ? C16 C6 C7 C11 154.73(16) . . . . ? C9 C6 C7 C11 43.2(2) . . . . ? O5 C4 C8 O4 158.62(15) . . . . ? C10 C4 C8 O4 33.01(19) . . . . ? C9 C4 C8 O4 -83.97(17) . . . . ? O5 C4 C8 C5 -86.53(19) . . . . ? C10 C4 C8 C5 147.86(16) . . . . ? C9 C4 C8 C5 30.88(19) . . . . ? O2 C5 C8 O4 152.17(14) . . . . ? C16 C5 C8 O4 37.73(18) . . . . ? O2 C5 C8 C4 35.2(2) . . . . ? C16 C5 C8 C4 -79.21(18) . . . . ? O1 C3 C9 C4 166.12(15) . . . . ? O2 C3 C9 C4 45.6(2) . . . . ? O1 C3 C9 C6 52.58(19) . . . . ? O2 C3 C9 C6 -67.96(19) . . . . ? O5 C4 C9 C3 45.6(2) . . . . ? C10 C4 C9 C3 169.04(16) . . . . ? C8 C4 C9 C3 -74.00(18) . . . . ? O5 C4 C9 C6 162.47(15) . . . . ? C10 C4 C9 C6 -74.06(18) . . . . ? C8 C4 C9 C6 42.90(18) . . . . ? C16 C6 C9 C3 31.88(19) . . . . ? C7 C6 C9 C3 141.53(16) . . . . ? C16 C6 C9 C4 -84.58(17) . . . . ? C7 C6 C9 C4 25.07(19) . . . . ? O5 C4 C10 C11 170.31(18) . . . . ? C9 C4 C10 C11 48.5(2) . . . . ? C8 C4 C10 C11 -63.9(2) . . . . ? O4 C7 C11 C10 47.8(2) . . . . ? C6 C7 C11 C10 -69.8(2) . . . . ? C4 C10 C11 C7 20.8(3) . . . . ? C7 C6 C16 O3 98.9(2) . . . . ? C9 C6 C16 O3 -147.2(2) . . . . ? C7 C6 C16 C5 -78.98(17) . . . . ? C9 C6 C16 C5 34.88(18) . . . . ? O2 C5 C16 O3 101.2(2) . . . . ? C8 C5 C16 O3 -140.6(2) . . . . ? O2 C5 C16 C6 -80.83(17) . . . . ? C8 C5 C16 C6 37.38(19) . . . . ? O2 C3 O1 C2 -67.4(2) . . . . ? C9 C3 O1 C2 172.80(16) . . . . ? C1 C2 O1 C3 -177.9(2) . . . . ? O1 C3 O2 C5 -93.44(17) . . . . ? C9 C3 O2 C5 24.6(2) . . . . ? C16 C5 O2 C3 44.91(19) . . . . ? C8 C5 O2 C3 -68.21(19) . . . . ? C4 C8 O4 C7 35.82(18) . . . . ? C5 C8 O4 C7 -81.62(17) . . . . ? C11 C7 O4 C8 -82.79(18) . . . . ? C6 C7 O4 C8 37.67(19) . . . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.904 _refine_diff_density_max 0.249 _refine_diff_density_min -0.394 _refine_diff_density_rms 0.070