data_04sjc0831 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 O5' _chemical_formula_weight 268.30 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 16.4963(18) _cell_length_b 8.325(3) _cell_length_c 20.061(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2755.0(14) _cell_formula_units_Z 8 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3533 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9760 _exptl_absorpt_correction_T_max 0.9981 _exptl_absorpt_process_details 'SADABS V2.10 (Sheldrick, G.M., 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator '10cm confocal mirrors' _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD Area Detector' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number none _diffrn_standards_decay_% negligible _diffrn_reflns_number 20102 _diffrn_reflns_av_R_equivalents 0.0905 _diffrn_reflns_av_sigmaI/netI 0.0670 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.92 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3155 _reflns_number_gt 1990 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement 'DENZO, COLLECT' _computing_data_reduction 'DENZO, COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'PLATON (Spek, 1990)' _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^)+(0.0458P)^2^+0.9768P] 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 SHELXL _refine_ls_extinction_coef 0.0049(8) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3155 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0977 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 0.974 _refine_ls_restrained_S_all 0.974 _refine_ls_shift/su_max 0.024 _refine_ls_shift/su_mean 0.003 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 0.10650(11) 0.6028(2) 0.15602(9) 0.0265(4) Uani 1 1 d . . . C2 C 0.07667(12) 0.6156(2) 0.09181(10) 0.0346(5) Uani 1 1 d . . . H2 H 0.0274 0.6713 0.0837 0.042 Uiso 1 1 calc R . . C3 C 0.11916(13) 0.5466(3) 0.03925(10) 0.0414(5) Uani 1 1 d . . . H3 H 0.0986 0.5546 -0.0049 0.050 Uiso 1 1 calc R . . C4 C 0.19043(12) 0.4672(3) 0.05067(10) 0.0390(5) Uani 1 1 d . . . H4 H 0.2188 0.4203 0.0144 0.047 Uiso 1 1 calc R . . C5 C 0.22184(11) 0.4543(2) 0.11478(10) 0.0326(5) Uani 1 1 d . . . H5 H 0.2715 0.3992 0.1223 0.039 Uiso 1 1 calc R . . C6 C 0.18018(10) 0.5223(2) 0.16750(9) 0.0253(4) Uani 1 1 d . . . C7 C -0.01388(11) 0.7071(2) 0.20599(9) 0.0300(4) Uani 1 1 d . . . H7A H -0.0461 0.6209 0.1847 0.036 Uiso 1 1 calc R . . H7B H -0.0184 0.8053 0.1784 0.036 Uiso 1 1 calc R . . C8 C -0.04430(11) 0.7387(2) 0.27450(9) 0.0320(5) Uani 1 1 d . . . H8A H -0.0061 0.8102 0.2984 0.038 Uiso 1 1 calc R . . H8B H -0.0977 0.7928 0.2723 0.038 Uiso 1 1 calc R . . C9 C -0.06303(11) 0.6089(3) 0.37886(9) 0.0335(5) Uani 1 1 d . . . H9A H -0.0920 0.5139 0.3965 0.040 Uiso 1 1 calc R . . H9B H -0.0973 0.7045 0.3870 0.040 Uiso 1 1 calc R . . C10 C 0.01605(11) 0.6282(2) 0.41580(9) 0.0317(5) Uani 1 1 d . . . H10A H 0.0478 0.7175 0.3963 0.038 Uiso 1 1 calc R . . H10B H 0.0055 0.6532 0.4633 0.038 Uiso 1 1 calc R . . C11 C 0.14053(11) 0.4944(2) 0.43276(10) 0.0330(5) Uani 1 1 d . . . H11A H 0.1414 0.5122 0.4815 0.040 Uiso 1 1 calc R . . H11B H 0.1675 0.5867 0.4109 0.040 Uiso 1 1 calc R . . C12 C 0.18465(12) 0.3416(2) 0.41604(10) 0.0345(5) Uani 1 1 d . . . H12A H 0.2370 0.3404 0.4402 0.041 Uiso 1 1 calc R . . H12B H 0.1522 0.2494 0.4321 0.041 Uiso 1 1 calc R . . C13 C 0.27036(11) 0.4037(2) 0.32405(10) 0.0335(5) Uani 1 1 d . . . H13A H 0.3198 0.3469 0.3392 0.040 Uiso 1 1 calc R . . H13B H 0.2715 0.5141 0.3423 0.040 Uiso 1 1 calc R . . C14 C 0.26840(10) 0.4094(2) 0.24999(10) 0.0311(5) Uani 1 1 d . . . H14A H 0.3207 0.4495 0.2323 0.037 Uiso 1 1 calc R . . H14B H 0.2582 0.3011 0.2315 0.037 Uiso 1 1 calc R . . O1 O 0.06936(7) 0.65908(15) 0.21157(6) 0.0291(3) Uani 1 1 d . . . O2 O -0.05174(7) 0.59002(15) 0.30918(6) 0.0299(3) Uani 1 1 d . . . O3 O 0.05977(7) 0.48216(16) 0.41035(6) 0.0315(3) Uani 1 1 d . . . O4 O 0.19986(7) 0.32128(15) 0.34725(6) 0.0316(3) Uani 1 1 d . . . O5 O 0.20375(7) 0.51684(14) 0.23245(6) 0.0270(3) 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 0.0288(10) 0.0232(10) 0.0275(11) -0.0001(8) 0.0039(8) -0.0015(8) C2 0.0376(11) 0.0346(12) 0.0317(12) 0.0051(9) -0.0015(9) -0.0014(9) C3 0.0477(14) 0.0484(14) 0.0282(12) 0.0008(10) 0.0034(9) -0.0084(11) C4 0.0414(12) 0.0410(13) 0.0346(12) -0.0074(9) 0.0140(9) -0.0087(10) C5 0.0278(10) 0.0270(11) 0.0431(13) -0.0037(9) 0.0093(8) -0.0049(9) C6 0.0272(10) 0.0182(9) 0.0306(11) 0.0008(8) 0.0021(7) -0.0052(8) C7 0.0281(10) 0.0266(10) 0.0351(11) 0.0019(8) -0.0044(8) 0.0070(8) C8 0.0301(10) 0.0271(10) 0.0388(12) 0.0002(9) -0.0006(8) 0.0064(9) C9 0.0290(10) 0.0396(12) 0.0318(11) -0.0034(9) 0.0043(8) 0.0040(9) C10 0.0336(11) 0.0310(11) 0.0306(11) -0.0054(8) 0.0016(8) 0.0028(9) C11 0.0305(10) 0.0358(12) 0.0326(11) -0.0045(9) -0.0047(8) -0.0025(9) C12 0.0362(11) 0.0332(12) 0.0340(12) 0.0037(9) -0.0059(8) -0.0012(9) C13 0.0239(10) 0.0260(11) 0.0506(13) 0.0072(9) -0.0042(8) -0.0001(8) C14 0.0222(9) 0.0243(10) 0.0467(12) 0.0043(9) 0.0026(8) 0.0038(8) O1 0.0267(7) 0.0302(7) 0.0303(7) -0.0022(6) -0.0017(5) 0.0067(6) O2 0.0316(7) 0.0286(8) 0.0295(7) -0.0014(6) -0.0007(5) 0.0001(6) O3 0.0276(7) 0.0310(8) 0.0360(8) -0.0040(6) -0.0058(5) 0.0003(6) O4 0.0322(7) 0.0249(7) 0.0377(8) 0.0006(6) 0.0013(6) -0.0028(6) O5 0.0254(7) 0.0210(7) 0.0346(8) -0.0020(5) -0.0022(5) 0.0037(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 C1 O1 1.355(2) . ? C1 C2 1.383(3) . ? C1 C6 1.407(3) . ? C2 C3 1.391(3) . ? C2 H2 0.9500 . ? C3 C4 1.368(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(3) . ? C4 H4 0.9500 . ? C5 C6 1.383(3) . ? C5 H5 0.9500 . ? C6 O5 1.361(2) . ? C7 O1 1.435(2) . ? C7 C8 1.487(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O2 1.425(2) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 O2 1.419(2) . ? C9 C10 1.509(3) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 O3 1.418(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 O3 1.410(2) . ? C11 C12 1.503(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 O4 1.413(2) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 O4 1.428(2) . ? C13 C14 1.487(3) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 O5 1.436(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? 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 C1 C2 125.33(17) . . ? O1 C1 C6 114.87(16) . . ? C2 C1 C6 119.78(17) . . ? C1 C2 C3 119.67(19) . . ? C1 C2 H2 120.2 . . ? C3 C2 H2 120.2 . . ? C4 C3 C2 120.4(2) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C3 C4 C5 120.83(19) . . ? C3 C4 H4 119.6 . . ? C5 C4 H4 119.6 . . ? C6 C5 C4 119.37(19) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? O5 C6 C5 125.22(17) . . ? O5 C6 C1 114.81(15) . . ? C5 C6 C1 119.95(17) . . ? O1 C7 C8 107.48(14) . . ? O1 C7 H7A 110.2 . . ? C8 C7 H7A 110.2 . . ? O1 C7 H7B 110.2 . . ? C8 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? O2 C8 C7 109.07(15) . . ? O2 C8 H8A 109.9 . . ? C7 C8 H8A 109.9 . . ? O2 C8 H8B 109.9 . . ? C7 C8 H8B 109.9 . . ? H8A C8 H8B 108.3 . . ? O2 C9 C10 112.47(15) . . ? O2 C9 H9A 109.1 . . ? C10 C9 H9A 109.1 . . ? O2 C9 H9B 109.1 . . ? C10 C9 H9B 109.1 . . ? H9A C9 H9B 107.8 . . ? O3 C10 C9 108.09(15) . . ? O3 C10 H10A 110.1 . . ? C9 C10 H10A 110.1 . . ? O3 C10 H10B 110.1 . . ? C9 C10 H10B 110.1 . . ? H10A C10 H10B 108.4 . . ? O3 C11 C12 108.99(15) . . ? O3 C11 H11A 109.9 . . ? C12 C11 H11A 109.9 . . ? O3 C11 H11B 109.9 . . ? C12 C11 H11B 109.9 . . ? H11A C11 H11B 108.3 . . ? O4 C12 C11 113.91(16) . . ? O4 C12 H12A 108.8 . . ? C11 C12 H12A 108.8 . . ? O4 C12 H12B 108.8 . . ? C11 C12 H12B 108.8 . . ? H12A C12 H12B 107.7 . . ? O4 C13 C14 108.87(15) . . ? O4 C13 H13A 109.9 . . ? C14 C13 H13A 109.9 . . ? O4 C13 H13B 109.9 . . ? C14 C13 H13B 109.9 . . ? H13A C13 H13B 108.3 . . ? O5 C14 C13 106.33(15) . . ? O5 C14 H14A 110.5 . . ? C13 C14 H14A 110.5 . . ? O5 C14 H14B 110.5 . . ? C13 C14 H14B 110.5 . . ? H14A C14 H14B 108.7 . . ? C1 O1 C7 117.71(14) . . ? C9 O2 C8 113.31(14) . . ? C11 O3 C10 113.21(14) . . ? C12 O4 C13 113.92(14) . . ? C6 O5 C14 117.90(14) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.212 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.048