data_f70514a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H14 O3' _chemical_formula_weight 218.24 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 P2(1)/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 6.215(6) _cell_length_b 7.015(6) _cell_length_c 26.60(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.404(12) _cell_angle_gamma 90.00 _cell_volume 1159.5(18) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 799 _cell_measurement_theta_min 3.063 _cell_measurement_theta_max 23.689 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.250 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 464 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9826 _exptl_absorpt_correction_T_max 0.9912 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4475 _diffrn_reflns_av_R_equivalents 0.0288 _diffrn_reflns_av_sigmaI/netI 0.0424 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 3.00 _diffrn_reflns_theta_max 25.01 _reflns_number_total 2019 _reflns_number_gt 1581 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1182P)^2^+2.8188P] 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 2019 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1186 _refine_ls_R_factor_gt 0.1028 _refine_ls_wR_factor_ref 0.3140 _refine_ls_wR_factor_gt 0.3046 _refine_ls_goodness_of_fit_ref 1.171 _refine_ls_restrained_S_all 1.171 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.6220(6) 0.2984(7) 0.14571(15) 0.0655(12) Uani 1 1 d . . . O2 O 0.7834(9) 0.2898(9) 0.02456(18) 0.0976(18) Uani 1 1 d . . . O3 O 0.9648(9) -0.0083(6) 0.10941(19) 0.0870(16) Uani 1 1 d . . . C1 C 0.7870(8) 0.3602(7) 0.24174(19) 0.0473(12) Uani 1 1 d . . . H1A H 0.6487 0.4054 0.2355 0.057 Uiso 1 1 calc R . . C2 C 0.8637(10) 0.3550(8) 0.2903(2) 0.0568(15) Uani 1 1 d . . . H2A H 0.7781 0.3981 0.3164 0.068 Uiso 1 1 calc R . . C3 C 1.0696(10) 0.2851(8) 0.3003(2) 0.0584(15) Uani 1 1 d . . . H3A H 1.1220 0.2804 0.3332 0.070 Uiso 1 1 calc R . . C4 C 1.1949(9) 0.2229(8) 0.2607(2) 0.0528(13) Uani 1 1 d . . . H4A H 1.3321 0.1751 0.2670 0.063 Uiso 1 1 calc R . . C5 C 1.1189(8) 0.2311(7) 0.2126(2) 0.0475(12) Uani 1 1 d . . . H5A H 1.2058 0.1907 0.1864 0.057 Uiso 1 1 calc R . . C6 C 0.9116(8) 0.2996(6) 0.20221(17) 0.0408(11) Uani 1 1 d . . . C7 C 0.8145(8) 0.3063(7) 0.15099(19) 0.0444(12) Uani 1 1 d . . . C8 C 0.9561(8) 0.3282(7) 0.10412(18) 0.0436(12) Uani 1 1 d . . . C9 C 1.1315(9) 0.4819(8) 0.1113(2) 0.0537(13) Uani 1 1 d . . . H9A H 1.0649 0.6022 0.1184 0.081 Uiso 1 1 calc R . . H9B H 1.2144 0.4924 0.0811 0.081 Uiso 1 1 calc R . . H9C H 1.2243 0.4466 0.1387 0.081 Uiso 1 1 calc R . . C10 C 0.8085(9) 0.3922(10) 0.0603(2) 0.0607(15) Uani 1 1 d . . . C11 C 0.7116(11) 0.5835(11) 0.0626(3) 0.0764(19) Uani 1 1 d . . . H11A H 0.6237 0.6041 0.0333 0.115 Uiso 1 1 calc R . . H11B H 0.8235 0.6778 0.0639 0.115 Uiso 1 1 calc R . . H11C H 0.6245 0.5933 0.0922 0.115 Uiso 1 1 calc R . . C12 C 1.0484(9) 0.1290(8) 0.0921(2) 0.0554(14) Uani 1 1 d . . . C13 C 1.2370(11) 0.1143(11) 0.0582(3) 0.078(2) Uani 1 1 d . . . H13A H 1.2764 -0.0172 0.0544 0.118 Uiso 1 1 calc R . . H13B H 1.3559 0.1838 0.0724 0.118 Uiso 1 1 calc R . . H13C H 1.2004 0.1669 0.0259 0.118 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 0.042(2) 0.095(3) 0.059(2) 0.007(2) -0.0046(17) -0.004(2) O2 0.107(4) 0.121(5) 0.064(3) -0.028(3) -0.032(3) -0.002(3) O3 0.122(4) 0.050(2) 0.090(3) -0.009(2) 0.038(3) -0.019(3) C1 0.054(3) 0.037(3) 0.051(3) 0.001(2) 0.004(2) 0.007(2) C2 0.081(4) 0.047(3) 0.043(3) 0.000(2) 0.011(3) 0.014(3) C3 0.081(4) 0.050(3) 0.043(3) 0.001(2) -0.007(3) 0.000(3) C4 0.055(3) 0.045(3) 0.059(3) 0.008(2) -0.008(2) 0.003(2) C5 0.046(3) 0.046(3) 0.051(3) 0.004(2) 0.005(2) 0.004(2) C6 0.046(3) 0.035(2) 0.041(2) -0.001(2) 0.002(2) -0.002(2) C7 0.043(3) 0.040(3) 0.050(3) 0.001(2) 0.000(2) -0.001(2) C8 0.048(3) 0.045(3) 0.038(2) -0.005(2) 0.002(2) -0.008(2) C9 0.054(3) 0.049(3) 0.058(3) 0.004(3) -0.003(2) -0.012(2) C10 0.057(3) 0.074(4) 0.051(3) 0.001(3) -0.002(2) -0.017(3) C11 0.078(4) 0.079(4) 0.072(4) 0.022(4) -0.022(3) -0.008(4) C12 0.064(3) 0.050(3) 0.052(3) -0.006(3) 0.003(3) -0.010(3) C13 0.082(4) 0.079(5) 0.074(4) -0.021(4) 0.024(3) 0.002(4) _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 C7 1.204(6) . ? O2 C10 1.200(7) . ? O3 C12 1.188(7) . ? C1 C2 1.373(8) . ? C1 C6 1.378(7) . ? C1 H1A 0.9300 . ? C2 C3 1.395(8) . ? C2 H2A 0.9300 . ? C3 C4 1.385(8) . ? C3 H3A 0.9300 . ? C4 C5 1.362(8) . ? C4 H4A 0.9300 . ? C5 C6 1.401(7) . ? C5 H5A 0.9300 . ? C6 C7 1.487(7) . ? C7 C8 1.539(7) . ? C8 C9 1.544(7) . ? C8 C12 1.544(8) . ? C8 C10 1.546(8) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C11 1.472(10) . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 C13 1.488(8) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 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 C2 C1 C6 121.0(5) . . ? C2 C1 H1A 119.5 . . ? C6 C1 H1A 119.5 . . ? C1 C2 C3 120.2(5) . . ? C1 C2 H2A 119.9 . . ? C3 C2 H2A 119.9 . . ? C4 C3 C2 119.0(5) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C5 C4 C3 120.5(5) . . ? C5 C4 H4A 119.7 . . ? C3 C4 H4A 119.7 . . ? C4 C5 C6 120.9(5) . . ? C4 C5 H5A 119.6 . . ? C6 C5 H5A 119.6 . . ? C1 C6 C5 118.4(5) . . ? C1 C6 C7 117.6(4) . . ? C5 C6 C7 124.0(4) . . ? O1 C7 C6 120.1(4) . . ? O1 C7 C8 118.9(4) . . ? C6 C7 C8 121.0(4) . . ? C7 C8 C9 112.2(4) . . ? C7 C8 C12 107.0(4) . . ? C9 C8 C12 113.2(4) . . ? C7 C8 C10 107.5(4) . . ? C9 C8 C10 107.7(4) . . ? C12 C8 C10 109.1(4) . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 C11 121.9(6) . . ? O2 C10 C8 119.8(6) . . ? C11 C10 C8 118.3(5) . . ? 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 . . ? O3 C12 C13 121.8(6) . . ? O3 C12 C8 119.3(5) . . ? C13 C12 C8 118.9(5) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.387 _refine_diff_density_min -0.338 _refine_diff_density_rms 0.079