data_a _audit_creation_method SHELXL-97 _chemical_name_systematic ; 'C12 H16 O3' ; _chemical_name_common 'C12 H16 O3' _chemical_melting_point ? _chemical_formula_moiety 'C12 H16 O3' _chemical_formula_sum 'C12 H16 O3' _chemical_formula_weight 208.25 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 'P2(1)/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 12.170(6) _cell_length_b 11.066(6) _cell_length_c 8.455(4) _cell_angle_alpha 90.00 _cell_angle_beta 109.476(10) _cell_angle_gamma 90.00 _cell_volume 1073.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 566(2) _cell_measurement_reflns_used 1188 _cell_measurement_theta_min 22.8 _cell_measurement_theta_max 67.5 _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type 'Multi-scan' _exptl_absorpt_correction_T_min 0.758 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 566(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 'Rigaku Saturn944+ (2x2 bin mode)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_detector_area_resol_mean 22.2222 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6354 _diffrn_reflns_av_R_equivalents 0.0659 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 25.28 _reflns_number_total 1904 _reflns_number_gt 1395 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) _computing_cell_refinement CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) _computing_data_reduction CrystalClear-SM Expert 2.0 r4 (Rigaku, 2009) _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.2500P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.28(5) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1904 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0973 _refine_ls_R_factor_gt 0.0866 _refine_ls_wR_factor_ref 0.3137 _refine_ls_wR_factor_gt 0.2872 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 0.2149(2) 0.5756(2) 0.1387(2) 0.0759(8) Uani 1 1 d . . . O2 O 0.0350(2) 0.6313(2) 0.1142(3) 0.0911(10) Uani 1 1 d . . . O3 O 0.42195(19) 0.7230(2) -0.1998(3) 0.0800(9) Uani 1 1 d . . . C4 C 0.2599(2) 0.4545(2) -0.3144(3) 0.0559(8) Uani 1 1 d . . . C5 C 0.2228(2) 0.6295(2) -0.1265(3) 0.0570(8) Uani 1 1 d . . . H5A H 0.2511 0.7125 -0.1001 0.068 Uiso 1 1 calc R . . C6 C 0.3317(3) 0.3936(3) -0.1503(4) 0.0679(9) Uani 1 1 d . . . H6A H 0.4113 0.4229 -0.1169 0.081 Uiso 1 1 calc R . . H6B H 0.3331 0.3070 -0.1680 0.081 Uiso 1 1 calc R . . C7 C 0.0974(2) 0.6277(3) -0.1326(4) 0.0634(9) Uani 1 1 d . . . H7A H 0.0579 0.7025 -0.1783 0.076 Uiso 1 1 calc R . . H7B H 0.0553 0.5604 -0.1992 0.076 Uiso 1 1 calc R . . C8 C 0.2818(3) 0.4185(3) -0.0096(4) 0.0706(10) Uani 1 1 d . . . H8A H 0.2024 0.3886 -0.0424 0.085 Uiso 1 1 calc R . . H8B H 0.3275 0.3756 0.0908 0.085 Uiso 1 1 calc R . . C9 C 0.3722(3) 0.6371(3) -0.2786(4) 0.0640(9) Uani 1 1 d . . . C10 C 0.3288(3) 0.4527(3) -0.4377(4) 0.0716(9) Uani 1 1 d . . . H10A H 0.3704 0.3769 -0.4291 0.086 Uiso 1 1 calc R . . H10B H 0.2764 0.4620 -0.5521 0.086 Uiso 1 1 calc R . . C11 C 0.1089(3) 0.6132(3) 0.0490(4) 0.0719(10) Uani 1 1 d . . . C12 C 0.2830(2) 0.5524(3) 0.0281(4) 0.0648(9) Uani 1 1 d . . . H12A H 0.3634 0.5801 0.0816 0.078 Uiso 1 1 calc R . . C13 C 0.2520(2) 0.5906(2) -0.2801(3) 0.0548(8) Uani 1 1 d . . . H13A H 0.1929 0.6255 -0.3786 0.066 Uiso 1 1 calc R . . C14 C 0.4146(3) 0.5586(3) -0.3891(4) 0.0700(9) Uani 1 1 d . . . H14A H 0.4929 0.5299 -0.3299 0.084 Uiso 1 1 calc R . . H14B H 0.4152 0.6025 -0.4881 0.084 Uiso 1 1 calc R . . C15 C 0.1428(3) 0.3915(3) -0.3906(4) 0.0834(11) Uani 1 1 d . . . H15A H 0.1554 0.3078 -0.4094 0.125 Uiso 1 1 calc R . . H15B H 0.1001 0.4292 -0.4953 0.125 Uiso 1 1 calc R . . H15C H 0.0991 0.3977 -0.3150 0.125 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 0.0922(17) 0.0860(17) 0.0601(13) -0.0037(10) 0.0394(11) -0.0092(11) O2 0.1084(19) 0.0833(17) 0.115(2) -0.0227(13) 0.0812(16) -0.0194(13) O3 0.0858(16) 0.0704(14) 0.0993(16) -0.0119(11) 0.0514(13) -0.0202(11) C4 0.0612(16) 0.0522(15) 0.0591(15) -0.0050(10) 0.0265(12) 0.0053(10) C5 0.0691(17) 0.0455(14) 0.0624(16) 0.0004(10) 0.0298(12) -0.0058(11) C6 0.0762(18) 0.0512(15) 0.0808(19) 0.0114(13) 0.0321(15) 0.0139(13) C7 0.0710(18) 0.0567(16) 0.0738(18) 0.0006(12) 0.0392(13) 0.0055(12) C8 0.078(2) 0.0624(18) 0.0731(18) 0.0199(13) 0.0270(15) 0.0046(13) C9 0.0725(18) 0.0594(17) 0.0713(17) 0.0096(12) 0.0390(14) 0.0035(12) C10 0.085(2) 0.0704(19) 0.0711(18) -0.0059(13) 0.0411(15) 0.0140(15) C11 0.082(2) 0.0628(17) 0.089(2) -0.0189(14) 0.0530(18) -0.0148(14) C12 0.0634(17) 0.0712(19) 0.0626(16) -0.0034(12) 0.0248(13) -0.0016(12) C13 0.0603(16) 0.0506(15) 0.0566(14) 0.0049(10) 0.0238(11) 0.0070(11) C14 0.0723(19) 0.0740(19) 0.0775(18) 0.0094(13) 0.0433(14) 0.0111(13) C15 0.083(2) 0.076(2) 0.094(2) -0.0222(17) 0.0326(17) -0.0066(17) _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 C11 1.326(4) . ? O1 C12 1.465(4) . ? O2 C11 1.217(4) . ? O3 C9 1.202(4) . ? C4 C15 1.523(4) . ? C4 C6 1.528(4) . ? C4 C10 1.540(4) . ? C4 C13 1.543(4) . ? C5 C7 1.510(4) . ? C5 C13 1.519(4) . ? C5 C12 1.528(4) . ? C6 C8 1.530(5) . ? C7 C11 1.503(4) . ? C8 C12 1.515(4) . ? C9 C14 1.488(4) . ? C9 C13 1.547(4) . ? C10 C14 1.531(5) . ? 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 C11 O1 C12 109.9(2) . . ? C15 C4 C6 110.7(3) . . ? C15 C4 C10 110.6(2) . . ? C6 C4 C10 109.5(2) . . ? C15 C4 C13 114.7(2) . . ? C6 C4 C13 108.2(2) . . ? C10 C4 C13 102.8(2) . . ? C7 C5 C13 119.3(2) . . ? C7 C5 C12 102.3(2) . . ? C13 C5 C12 113.0(2) . . ? C4 C6 C8 111.8(2) . . ? C11 C7 C5 102.6(2) . . ? C12 C8 C6 111.2(2) . . ? O3 C9 C14 126.4(3) . . ? O3 C9 C13 124.6(3) . . ? C14 C9 C13 109.0(3) . . ? C14 C10 C4 106.6(2) . . ? O2 C11 O1 121.1(3) . . ? O2 C11 C7 127.9(3) . . ? O1 C11 C7 111.0(2) . . ? O1 C12 C8 109.7(2) . . ? O1 C12 C5 103.6(2) . . ? C8 C12 C5 113.4(2) . . ? C5 C13 C4 119.0(2) . . ? C5 C13 C9 112.9(2) . . ? C4 C13 C9 102.0(2) . . ? C9 C14 C10 105.5(2) . . ? _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 25.28 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 0.490 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.074