data_tri _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H10 O4' _chemical_formula_weight 218.20 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5873(9) _cell_length_b 8.0869(12) _cell_length_c 10.0489(9) _cell_angle_alpha 102.730(10) _cell_angle_beta 96.588(9) _cell_angle_gamma 117.756(13) _cell_volume 515.07(11) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 991 _cell_measurement_theta_min 3.6120 _cell_measurement_theta_max 28.0800 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.106 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.96237 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 3336 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2015 _reflns_number_gt 1695 _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^)+(0.0737P)^2^+0.3154P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2015 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0619 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1470 _refine_ls_wR_factor_gt 0.1400 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 O2 O -0.0028(2) 0.5184(2) 0.27176(15) 0.0270(4) Uani 1 1 d . . . O4 O 0.1012(2) 1.1569(2) 0.90547(15) 0.0316(4) Uani 1 1 d . . . O3 O -0.2093(2) 1.0257(3) 0.76139(17) 0.0376(4) Uani 1 1 d . . . C4 C -0.0437(3) 0.7056(3) 0.4619(2) 0.0216(4) Uani 1 1 d . . . O1 O 0.3347(2) 0.6254(2) 0.34543(17) 0.0366(4) Uani 1 1 d . . . C7 C 0.2375(3) 0.9870(3) 0.7082(2) 0.0270(5) Uani 1 1 d . . . H7A H 0.3319 1.0841 0.7934 0.032 Uiso 1 1 calc R . . C5 C -0.1130(3) 0.7981(3) 0.5588(2) 0.0233(4) Uani 1 1 d . . . H5A H -0.2527 0.7661 0.5413 0.028 Uiso 1 1 calc R . . C2 C 0.1870(3) 0.6345(3) 0.3679(2) 0.0258(5) Uani 1 1 d . . . C11 C -0.0415(3) 1.0428(3) 0.7848(2) 0.0244(5) Uani 1 1 d . . . C8 C 0.3060(3) 0.8949(3) 0.6118(2) 0.0274(5) Uani 1 1 d . . . H8A H 0.4455 0.9267 0.6287 0.033 Uiso 1 1 calc R . . C6 C 0.0306(3) 0.9390(3) 0.6820(2) 0.0230(4) Uani 1 1 d . . . C3 C -0.1491(3) 0.5568(3) 0.3236(2) 0.0240(5) Uani 1 1 d . . . C1 C 0.1611(3) 0.7543(3) 0.4893(2) 0.0233(5) Uani 1 1 d . . . C9 C -0.3422(3) 0.4642(3) 0.2483(2) 0.0304(5) Uani 1 1 d . . . H9A H -0.4344 0.4960 0.2882 0.036 Uiso 1 1 calc R . . C10 C -0.4273(4) 0.3138(4) 0.1056(2) 0.0390(6) Uani 1 1 d . . . H10A H -0.5738 0.2680 0.0727 0.059 Uiso 1 1 calc R . . H10B H -0.4105 0.2023 0.1113 0.059 Uiso 1 1 calc R . . H10C H -0.3533 0.3726 0.0394 0.059 Uiso 1 1 calc R . . C12 C 0.0453(4) 1.2674(4) 1.0086(2) 0.0359(6) Uani 1 1 d . . . H12A H 0.1598 1.3463 1.0933 0.054 Uiso 1 1 calc R . . H12B H -0.0767 1.1763 1.0334 0.054 Uiso 1 1 calc R . . H12C H 0.0150 1.3544 0.9689 0.054 Uiso 1 1 calc R . . 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 O2 0.0236(8) 0.0284(8) 0.0244(8) -0.0012(6) 0.0059(6) 0.0137(6) O4 0.0323(8) 0.0364(9) 0.0227(8) -0.0034(6) 0.0036(6) 0.0209(7) O3 0.0324(9) 0.0513(10) 0.0304(9) 0.0005(7) 0.0063(7) 0.0278(8) C4 0.0225(10) 0.0216(10) 0.0224(10) 0.0067(8) 0.0054(8) 0.0126(8) O1 0.0274(8) 0.0400(9) 0.0393(10) -0.0004(7) 0.0107(7) 0.0197(7) C7 0.0250(11) 0.0285(11) 0.0228(11) 0.0018(9) 0.0023(8) 0.0134(9) C5 0.0233(10) 0.0260(10) 0.0236(10) 0.0069(8) 0.0065(8) 0.0150(8) C2 0.0238(10) 0.0254(10) 0.0272(11) 0.0050(9) 0.0059(8) 0.0131(9) C11 0.0270(11) 0.0259(11) 0.0224(11) 0.0074(9) 0.0060(8) 0.0150(9) C8 0.0208(10) 0.0303(11) 0.0279(11) 0.0033(9) 0.0031(8) 0.0137(9) C6 0.0274(10) 0.0236(10) 0.0214(10) 0.0069(8) 0.0070(8) 0.0155(8) C3 0.0258(11) 0.0259(10) 0.0249(11) 0.0063(8) 0.0089(8) 0.0169(9) C1 0.0229(10) 0.0241(10) 0.0243(10) 0.0053(8) 0.0070(8) 0.0138(8) C9 0.0259(11) 0.0334(12) 0.0283(12) 0.0016(9) 0.0041(9) 0.0164(9) C10 0.0291(12) 0.0431(14) 0.0316(13) -0.0042(11) 0.0004(10) 0.0164(11) C12 0.0436(14) 0.0400(13) 0.0263(12) -0.0010(10) 0.0097(10) 0.0275(11) _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 O2 C2 1.382(2) . ? O2 C3 1.408(2) . ? O4 C11 1.330(2) . ? O4 C12 1.449(2) . ? O3 C11 1.204(3) . ? C4 C1 1.389(3) . ? C4 C5 1.396(3) . ? C4 C3 1.459(3) . ? O1 C2 1.200(3) . ? C7 C8 1.386(3) . ? C7 C6 1.405(3) . ? C5 C6 1.389(3) . ? C2 C1 1.476(3) . ? C11 C6 1.499(3) . ? C8 C1 1.387(3) . ? C3 C9 1.324(3) . ? C9 C10 1.497(3) . ? 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 O2 C3 109.92(16) . . ? C11 O4 C12 115.65(17) . . ? C1 C4 C5 120.55(18) . . ? C1 C4 C3 107.70(17) . . ? C5 C4 C3 131.74(18) . . ? C8 C7 C6 121.09(19) . . ? C6 C5 C4 117.26(18) . . ? O1 C2 O2 121.29(19) . . ? O1 C2 C1 131.5(2) . . ? O2 C2 C1 107.20(16) . . ? O3 C11 O4 123.52(19) . . ? O3 C11 C6 124.07(19) . . ? O4 C11 C6 112.42(17) . . ? C7 C8 C1 116.85(19) . . ? C5 C6 C7 121.55(19) . . ? C5 C6 C11 117.55(18) . . ? C7 C6 C11 120.88(18) . . ? C9 C3 O2 120.75(19) . . ? C9 C3 C4 131.93(19) . . ? O2 C3 C4 107.32(16) . . ? C8 C1 C4 122.69(19) . . ? C8 C1 C2 129.45(18) . . ? C4 C1 C2 107.85(17) . . ? C3 C9 C10 125.5(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.508 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.052