data_int_3_0m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H12 O3' _chemical_formula_sum 'C11 H12 O3' _chemical_formula_weight 192.21 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 7.2646(7) _cell_length_b 8.0955(8) _cell_length_c 8.1840(9) _cell_angle_alpha 90.831(6) _cell_angle_beta 97.639(6) _cell_angle_gamma 93.425(6) _cell_volume 476.06(8) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5309 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 31.78 _exptl_crystal_description 'BLOCK' _exptl_crystal_colour 'YELLOW' _exptl_crystal_size_max 0.56 _exptl_crystal_size_mid 0.43 _exptl_crystal_size_min 0.39 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.341 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 204 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type 'MULTI-SCAN' _exptl_absorpt_correction_T_min 0.9476 _exptl_absorpt_correction_T_max 0.9631 _exptl_absorpt_process_details 'SADABS,(BRUKER,2006)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 8060 _diffrn_reflns_av_R_equivalents 0.0149 _diffrn_reflns_av_sigmaI/netI 0.0111 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1681 _reflns_number_gt 1515 _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^)+(0.0550P)^2^+0.1017P] 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 1681 _refine_ls_number_parameters 131 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0409 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.1078 _refine_ls_wR_factor_gt 0.1039 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 -0.33320(13) 0.47785(12) 0.11351(13) 0.0499(3) Uani 1 1 d . . . O2 O -0.18364(14) 0.18065(13) 0.02642(14) 0.0558(3) Uani 1 1 d . . . H2 H -0.1192 0.1055 0.0049 0.084 Uiso 1 1 calc R . . O3 O 0.18051(13) 0.13700(12) 0.14432(14) 0.0531(3) Uani 1 1 d . . . C1 C -0.3504(2) 0.63296(18) 0.18028(19) 0.0522(4) Uani 1 1 d . . . H1 H -0.4604 0.6875 0.1664 0.063 Uiso 1 1 calc R . . C2 C -0.1920(2) 0.69660(17) 0.26717(17) 0.0449(3) Uani 1 1 d . . . C3 C -0.1664(2) 0.86288(19) 0.3527(2) 0.0599(4) Uani 1 1 d . . . H3A H -0.2810 0.9173 0.3352 0.090 Uiso 1 1 calc R . . H3B H -0.0707 0.9286 0.3091 0.090 Uiso 1 1 calc R . . H3C H -0.1312 0.8492 0.4688 0.090 Uiso 1 1 calc R . . C4 C -0.05660(18) 0.57297(16) 0.25884(15) 0.0396(3) Uani 1 1 d . . . C5 C -0.15226(18) 0.44364(17) 0.16236(16) 0.0400(3) Uani 1 1 d . . . C6 C -0.07592(18) 0.29902(16) 0.12195(16) 0.0414(3) Uani 1 1 d . . . C7 C 0.10903(19) 0.28454(16) 0.18466(17) 0.0420(3) Uani 1 1 d . . . C8 C 0.3747(2) 0.1205(2) 0.1934(2) 0.0613(4) Uani 1 1 d . . . H8A H 0.4448 0.2106 0.1510 0.092 Uiso 1 1 calc R . . H8B H 0.4097 0.0176 0.1504 0.092 Uiso 1 1 calc R . . H8C H 0.4001 0.1221 0.3116 0.092 Uiso 1 1 calc R . . C9 C 0.20942(19) 0.41173(18) 0.28189(18) 0.0461(4) Uani 1 1 d . . . H9 H 0.3335 0.3985 0.3217 0.055 Uiso 1 1 calc R . . C10 C 0.13088(19) 0.55698(17) 0.32132(16) 0.0425(3) Uani 1 1 d . . . C11 C 0.2452(2) 0.6892(2) 0.4286(2) 0.0577(4) Uani 1 1 d . . . H11A H 0.3673 0.6524 0.4623 0.086 Uiso 1 1 calc R . . H11B H 0.1860 0.7105 0.5242 0.086 Uiso 1 1 calc R . . H11C H 0.2549 0.7890 0.3674 0.086 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 O1 0.0390(5) 0.0476(6) 0.0598(6) -0.0111(5) -0.0045(4) 0.0028(4) O2 0.0446(6) 0.0454(6) 0.0726(7) -0.0208(5) -0.0060(5) -0.0012(4) O3 0.0405(6) 0.0428(6) 0.0738(7) -0.0114(5) 0.0009(5) 0.0017(4) C1 0.0490(8) 0.0466(8) 0.0600(9) -0.0066(7) 0.0024(7) 0.0085(6) C2 0.0500(8) 0.0406(7) 0.0433(7) -0.0018(6) 0.0050(6) 0.0008(6) C3 0.0695(11) 0.0449(8) 0.0637(10) -0.0098(7) 0.0040(8) 0.0044(7) C4 0.0439(7) 0.0385(7) 0.0355(7) 0.0001(5) 0.0049(5) -0.0039(5) C5 0.0362(7) 0.0421(7) 0.0399(7) -0.0012(5) 0.0012(5) -0.0017(5) C6 0.0403(7) 0.0396(7) 0.0422(7) -0.0044(6) 0.0019(6) -0.0055(5) C7 0.0400(7) 0.0388(7) 0.0462(7) -0.0011(6) 0.0042(6) -0.0010(6) C8 0.0412(8) 0.0531(9) 0.0871(12) -0.0120(8) 0.0003(8) 0.0050(7) C9 0.0370(7) 0.0477(8) 0.0507(8) -0.0014(6) -0.0020(6) -0.0029(6) C10 0.0436(7) 0.0422(7) 0.0392(7) -0.0016(5) 0.0010(6) -0.0065(6) C11 0.0532(9) 0.0537(9) 0.0608(9) -0.0121(7) -0.0050(7) -0.0088(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 O1 C5 1.3680(16) . ? O1 C1 1.3814(18) . ? O2 C6 1.3667(16) . ? O2 H2 0.8200 . ? O3 C7 1.3833(17) . ? O3 C8 1.4293(17) . ? C1 C2 1.341(2) . ? C1 H1 0.9300 . ? C2 C4 1.4515(19) . ? C2 C3 1.498(2) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.3949(18) . ? C4 C10 1.4039(19) . ? C5 C6 1.379(2) . ? C6 C7 1.386(2) . ? C7 C9 1.399(2) . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C9 C10 1.389(2) . ? C9 H9 0.9300 . ? C10 C11 1.5097(19) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? 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 C5 O1 C1 104.99(11) . . ? C6 O2 H2 109.5 . . ? C7 O3 C8 117.25(11) . . ? C2 C1 O1 112.87(13) . . ? C2 C1 H1 123.6 . . ? O1 C1 H1 123.6 . . ? C1 C2 C4 105.96(12) . . ? C1 C2 C3 125.38(14) . . ? C4 C2 C3 128.67(13) . . ? C2 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C2 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C5 C4 C10 118.63(12) . . ? C5 C4 C2 104.96(12) . . ? C10 C4 C2 136.41(13) . . ? O1 C5 C6 124.02(12) . . ? O1 C5 C4 111.22(12) . . ? C6 C5 C4 124.75(12) . . ? O2 C6 C5 119.52(12) . . ? O2 C6 C7 124.41(13) . . ? C5 C6 C7 116.07(12) . . ? O3 C7 C6 114.66(12) . . ? O3 C7 C9 124.57(12) . . ? C6 C7 C9 120.77(13) . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C10 C9 C7 122.56(13) . . ? C10 C9 H9 118.7 . . ? C7 C9 H9 118.7 . . ? C9 C10 C4 117.22(12) . . ? C9 C10 C11 120.28(13) . . ? C4 C10 C11 122.50(13) . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? 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 C5 O1 C1 C2 -0.02(17) . . . . ? O1 C1 C2 C4 -0.35(17) . . . . ? O1 C1 C2 C3 179.39(13) . . . . ? C1 C2 C4 C5 0.57(15) . . . . ? C3 C2 C4 C5 -179.15(14) . . . . ? C1 C2 C4 C10 -179.14(15) . . . . ? C3 C2 C4 C10 1.1(3) . . . . ? C1 O1 C5 C6 179.92(13) . . . . ? C1 O1 C5 C4 0.41(15) . . . . ? C10 C4 C5 O1 179.16(11) . . . . ? C2 C4 C5 O1 -0.62(15) . . . . ? C10 C4 C5 C6 -0.3(2) . . . . ? C2 C4 C5 C6 179.88(12) . . . . ? O1 C5 C6 O2 0.5(2) . . . . ? C4 C5 C6 O2 179.93(12) . . . . ? O1 C5 C6 C7 -178.95(12) . . . . ? C4 C5 C6 C7 0.5(2) . . . . ? C8 O3 C7 C6 174.75(13) . . . . ? C8 O3 C7 C9 -5.9(2) . . . . ? O2 C6 C7 O3 -0.5(2) . . . . ? C5 C6 C7 O3 178.93(11) . . . . ? O2 C6 C7 C9 -179.88(13) . . . . ? C5 C6 C7 C9 -0.5(2) . . . . ? O3 C7 C9 C10 -179.00(13) . . . . ? C6 C7 C9 C10 0.3(2) . . . . ? C7 C9 C10 C4 -0.2(2) . . . . ? C7 C9 C10 C11 179.22(13) . . . . ? C5 C4 C10 C9 0.17(19) . . . . ? C2 C4 C10 C9 179.85(14) . . . . ? C5 C4 C10 C11 -179.22(13) . . . . ? C2 C4 C10 C11 0.5(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.150 _refine_diff_density_min -0.165 _refine_diff_density_rms 0.031