data_13kaw17h _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _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 12.7394(10) _cell_length_b 5.3825(4) _cell_length_c 17.5551(13) _cell_angle_alpha 90.00 _cell_angle_beta 95.1140(12) _cell_angle_gamma 90.00 _cell_volume 1198.96(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4843 _cell_measurement_theta_min 2.33 _cell_measurement_theta_max 28.22 _exptl_crystal_description 'needle' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.47 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9529 _exptl_absorpt_correction_T_max 0.9918 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17791 _diffrn_reflns_av_R_equivalents 0.0358 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 28.28 _reflns_number_total 2976 _reflns_number_gt 2442 _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^)+(0.0407P)^2^+0.5019P] 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 2976 _refine_ls_number_parameters 161 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0934 _refine_ls_wR_factor_gt 0.0860 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 0.43028(6) 0.80127(15) 0.31624(5) 0.01453(18) Uani 1 1 d . . . O2 O 0.31902(6) 0.80765(15) 0.33239(5) 0.01528(18) Uani 1 1 d . . . O3 O 0.16962(7) 0.4223(2) 0.33572(5) 0.0260(2) Uani 1 1 d . . . H3O H 0.1708(14) 0.502(3) 0.2958(11) 0.039 Uiso 1 1 d . . . O4 O 0.41584(7) 0.41250(16) 0.25610(5) 0.01770(19) Uani 1 1 d . . . O5 O 0.46009(7) 0.51991(17) 0.18938(5) 0.0208(2) Uani 1 1 d . . . H5O H 0.4166(13) 0.647(3) 0.1811(9) 0.031 Uiso 1 1 d . . . C1 C 0.45743(9) 0.5449(2) 0.32201(6) 0.0138(2) Uani 1 1 d . . . C2 C 0.39490(9) 0.4423(2) 0.38603(7) 0.0156(2) Uani 1 1 d . . . H2A H 0.4420 0.4070 0.4327 0.019 Uiso 1 1 calc R . . H2B H 0.3568 0.2884 0.3696 0.019 Uiso 1 1 calc R . . C3 C 0.31737(9) 0.6531(2) 0.40004(6) 0.0138(2) Uani 1 1 d . . . C4 C 0.20299(9) 0.5709(2) 0.39969(7) 0.0177(2) Uani 1 1 d . . . H4A H 0.1943 0.4759 0.4470 0.021 Uiso 1 1 calc R . . H4B H 0.1574 0.7198 0.3999 0.021 Uiso 1 1 calc R . . C5 C 0.35036(10) 0.8051(2) 0.47113(7) 0.0190(3) Uani 1 1 d . . . H5A H 0.3487 0.7000 0.5166 0.028 Uiso 1 1 calc R . . H5B H 0.3017 0.9449 0.4745 0.028 Uiso 1 1 calc R . . H5C H 0.4220 0.8684 0.4681 0.028 Uiso 1 1 calc R . . C6 C 0.57654(9) 0.5347(2) 0.33521(6) 0.0140(2) Uani 1 1 d . . . C7 C 0.63259(10) 0.3352(2) 0.30855(7) 0.0166(2) Uani 1 1 d . . . H7 H 0.5963 0.2084 0.2792 0.020 Uiso 1 1 calc R . . C8 C 0.74118(10) 0.3204(2) 0.32466(7) 0.0183(2) Uani 1 1 d . . . H8 H 0.7783 0.1837 0.3058 0.022 Uiso 1 1 calc R . . C9 C 0.79676(9) 0.5023(2) 0.36802(7) 0.0176(2) Uani 1 1 d . . . C10 C 0.74029(9) 0.7025(2) 0.39360(7) 0.0172(2) Uani 1 1 d . . . H10 H 0.7768 0.8302 0.4224 0.021 Uiso 1 1 calc R . . C11 C 0.63159(9) 0.7195(2) 0.37781(7) 0.0162(2) Uani 1 1 d . . . H11 H 0.5947 0.8574 0.3961 0.019 Uiso 1 1 calc R . . C12 C 0.91434(10) 0.4850(3) 0.38671(8) 0.0252(3) Uani 1 1 d . . . H12A H 0.9294 0.4075 0.4370 0.038 Uiso 0.50 1 calc PR . . H12B H 0.9450 0.6521 0.3874 0.038 Uiso 0.50 1 calc PR . . H12C H 0.9451 0.3842 0.3478 0.038 Uiso 0.50 1 calc PR . . H12D H 0.9365 0.3162 0.4022 0.038 Uiso 0.50 1 d PR A 2 H12E H 0.9391 0.5776 0.4333 0.038 Uiso 0.50 1 d PR B 2 H12F H 0.9555 0.5411 0.3452 0.038 Uiso 0.50 1 d PR C 2 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 0.0128(4) 0.0118(4) 0.0191(4) 0.0012(3) 0.0019(3) 0.0010(3) O2 0.0118(4) 0.0176(4) 0.0164(4) 0.0044(3) 0.0007(3) 0.0017(3) O3 0.0251(5) 0.0356(6) 0.0164(4) -0.0014(4) -0.0032(4) -0.0146(4) O4 0.0211(4) 0.0169(4) 0.0148(4) -0.0008(3) -0.0003(3) -0.0030(3) O5 0.0268(5) 0.0215(5) 0.0141(4) 0.0017(3) 0.0023(3) 0.0040(4) C1 0.0160(5) 0.0105(5) 0.0145(5) -0.0002(4) -0.0006(4) 0.0003(4) C2 0.0160(5) 0.0130(5) 0.0178(5) 0.0028(4) 0.0008(4) -0.0001(4) C3 0.0149(5) 0.0137(5) 0.0125(5) 0.0016(4) -0.0006(4) -0.0012(4) C4 0.0149(5) 0.0221(6) 0.0159(5) -0.0003(5) -0.0005(4) -0.0022(5) C5 0.0223(6) 0.0183(6) 0.0159(6) -0.0012(5) -0.0006(5) -0.0029(5) C6 0.0153(5) 0.0137(5) 0.0132(5) 0.0019(4) 0.0014(4) 0.0000(4) C7 0.0209(6) 0.0138(5) 0.0148(5) -0.0009(4) 0.0006(4) 0.0008(4) C8 0.0217(6) 0.0160(5) 0.0175(6) 0.0012(4) 0.0042(5) 0.0055(5) C9 0.0169(6) 0.0190(6) 0.0172(6) 0.0043(5) 0.0032(4) 0.0014(4) C10 0.0167(6) 0.0164(6) 0.0184(6) -0.0003(4) 0.0002(4) -0.0021(4) C11 0.0171(6) 0.0135(5) 0.0181(6) -0.0006(4) 0.0021(4) 0.0009(4) C12 0.0168(6) 0.0296(7) 0.0292(7) 0.0009(6) 0.0019(5) 0.0038(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 1.4243(13) . ? O1 O2 1.4704(11) . ? O2 C3 1.4516(13) . ? O3 C4 1.4130(14) . ? O3 H3O 0.822(19) . ? O4 C1 1.4204(13) . ? O4 O5 1.4635(12) . ? O5 H5O 0.882(18) . ? C1 C6 1.5154(16) . ? C1 C2 1.5369(16) . ? C2 C3 1.5385(16) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C5 1.5199(16) . ? C3 C4 1.5223(16) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 C7 1.3935(16) . ? C6 C11 1.3953(16) . ? C7 C8 1.3893(17) . ? C7 H7 0.9500 . ? C8 C9 1.3940(17) . ? C8 H8 0.9500 . ? C9 C10 1.3924(17) . ? C9 C12 1.5074(17) . ? C10 C11 1.3907(16) . ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C12 H12D 0.9820 . ? C12 H12E 0.9848 . ? C12 H12F 0.9835 . ? 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 O1 O2 103.95(7) . . ? C3 O2 O1 103.23(7) . . ? C4 O3 H3O 110.9(13) . . ? C1 O4 O5 108.15(8) . . ? O4 O5 H5O 98.9(11) . . ? O4 C1 O1 110.95(9) . . ? O4 C1 C6 113.72(9) . . ? O1 C1 C6 106.23(9) . . ? O4 C1 C2 103.62(9) . . ? O1 C1 C2 105.16(9) . . ? C6 C1 C2 116.90(9) . . ? C1 C2 C3 103.53(9) . . ? C1 C2 H2A 111.1 . . ? C3 C2 H2A 111.1 . . ? C1 C2 H2B 111.1 . . ? C3 C2 H2B 111.1 . . ? H2A C2 H2B 109.0 . . ? O2 C3 C5 109.89(9) . . ? O2 C3 C4 104.30(9) . . ? C5 C3 C4 110.75(10) . . ? O2 C3 C2 103.62(9) . . ? C5 C3 C2 113.19(10) . . ? C4 C3 C2 114.39(10) . . ? O3 C4 C3 112.81(10) . . ? O3 C4 H4A 109.0 . . ? C3 C4 H4A 109.0 . . ? O3 C4 H4B 109.0 . . ? C3 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C3 C5 H5A 109.5 . . ? C3 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C3 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C7 C6 C11 118.77(11) . . ? C7 C6 C1 120.83(10) . . ? C11 C6 C1 120.32(10) . . ? C8 C7 C6 120.43(11) . . ? C8 C7 H7 119.8 . . ? C6 C7 H7 119.8 . . ? C7 C8 C9 121.27(11) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C10 C9 C8 117.90(11) . . ? C10 C9 C12 120.63(11) . . ? C8 C9 C12 121.47(11) . . ? C11 C10 C9 121.36(11) . . ? C11 C10 H10 119.3 . . ? C9 C10 H10 119.3 . . ? C10 C11 C6 120.27(11) . . ? C10 C11 H11 119.9 . . ? C6 C11 H11 119.9 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C12 H12D 111.9 . . ? C9 C12 H12E 112.8 . . ? H12D C12 H12E 100.2 . . ? C9 C12 H12F 113.9 . . ? H12D C12 H12F 109.3 . . ? H12E C12 H12F 107.9 . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.343 _refine_diff_density_min -0.220 _refine_diff_density_rms 0.045