data_sjb05b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H20 O3' _chemical_formula_weight 236.30 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 12.7483(14) _cell_length_b 8.5538(9) _cell_length_c 11.2196(12) _cell_angle_alpha 90.00 _cell_angle_beta 96.766(2) _cell_angle_gamma 90.00 _cell_volume 1214.9(2) _cell_formula_units_Z 4 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2125 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 27.68 _exptl_crystal_description ? _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 8807 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 28.32 _reflns_number_total 3026 _reflns_number_gt 2111 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0757P)^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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3026 _refine_ls_number_parameters 154 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0721 _refine_ls_R_factor_gt 0.0516 _refine_ls_wR_factor_ref 0.1410 _refine_ls_wR_factor_gt 0.1329 _refine_ls_goodness_of_fit_ref 1.007 _refine_ls_restrained_S_all 1.007 _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 0.60079(10) 0.18500(14) 0.76742(11) 0.0294(3) Uani 1 1 d . . . H1A H 0.5768 0.2731 0.7740 0.044 Uiso 1 1 calc R . . O3 O 0.55207(10) 0.48101(14) 0.70039(12) 0.0307(3) Uani 1 1 d . . . H3A H 0.5720 0.3924 0.7194 0.046 Uiso 1 1 calc R . . O2 O 0.73517(10) 0.79393(14) 0.50112(12) 0.0312(3) Uani 1 1 d . . . C14 C 0.80452(13) 0.36962(18) 0.72191(15) 0.0187(4) Uani 1 1 d . . . H14A H 0.8579 0.3585 0.7917 0.022 Uiso 1 1 calc R . . C7 C 0.85230(13) 0.40086(18) 0.60200(14) 0.0180(3) Uani 1 1 d . . . H7A H 0.9289 0.4166 0.6091 0.022 Uiso 1 1 calc R . . C12 C 0.63664(13) 0.5661(2) 0.66069(16) 0.0228(4) Uani 1 1 d . . . H12A H 0.6229 0.6775 0.6722 0.027 Uiso 1 1 calc R . . C2 C 0.76089(13) 0.20954(18) 0.66904(14) 0.0181(4) Uani 1 1 d . . . C13 C 0.75050(14) 0.53369(19) 0.71258(15) 0.0211(4) Uani 1 1 d . . . H13A H 0.7816 0.6113 0.7706 0.025 Uiso 1 1 calc R . . C9 C 0.82533(14) 0.69717(19) 0.53318(16) 0.0259(4) Uani 1 1 d . . . H9A H 0.8750 0.7488 0.5925 0.031 Uiso 1 1 calc R . . H9B H 0.8606 0.6742 0.4632 0.031 Uiso 1 1 calc R . . C8 C 0.78434(13) 0.54891(19) 0.58412(14) 0.0183(4) Uani 1 1 d . . . C1 C 0.64440(13) 0.1726(2) 0.65564(16) 0.0240(4) Uani 1 1 d . . . H1B H 0.6075 0.2440 0.5980 0.029 Uiso 1 1 calc R . . H1C H 0.6334 0.0673 0.6246 0.029 Uiso 1 1 calc R . . C5 C 0.89879(13) 0.12202(19) 0.54588(15) 0.0220(4) Uani 1 1 d . . . H5A H 0.9574 0.1650 0.5087 0.026 Uiso 1 1 calc R . . H5B H 0.8724 0.0301 0.5015 0.026 Uiso 1 1 calc R . . C6 C 0.81175(12) 0.24299(18) 0.54993(14) 0.0174(3) Uani 1 1 d . . . H6A H 0.7614 0.2498 0.4770 0.021 Uiso 1 1 calc R . . C11 C 0.66546(13) 0.54492(19) 0.53127(15) 0.0212(4) Uani 1 1 d . . . H11A H 0.6415 0.4469 0.4918 0.025 Uiso 1 1 calc R . . C4 C 0.93261(14) 0.0821(2) 0.67730(16) 0.0265(4) Uani 1 1 d . . . H4A H 0.9785 0.1622 0.7160 0.032 Uiso 1 1 calc R . . H4B H 0.9687 -0.0178 0.6851 0.032 Uiso 1 1 calc R . . C3 C 0.82744(15) 0.0759(2) 0.73016(16) 0.0244(4) Uani 1 1 d . . . H3B H 0.8383 0.0909 0.8164 0.029 Uiso 1 1 calc R . . H3C H 0.7929 -0.0240 0.7131 0.029 Uiso 1 1 calc R . . C10 C 0.65317(15) 0.6893(2) 0.45249(17) 0.0290(4) Uani 1 1 d . . . H10A H 0.6613 0.6630 0.3700 0.035 Uiso 1 1 calc R . . H10B H 0.5842 0.7363 0.4550 0.035 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 0.0273(7) 0.0268(7) 0.0377(8) 0.0038(5) 0.0190(6) -0.0018(5) O3 0.0263(7) 0.0215(6) 0.0473(9) 0.0042(6) 0.0167(6) 0.0019(5) O2 0.0316(7) 0.0195(7) 0.0421(8) 0.0062(5) 0.0024(6) -0.0006(5) C14 0.0161(8) 0.0231(8) 0.0171(8) -0.0020(6) 0.0026(6) -0.0006(7) C7 0.0151(8) 0.0205(8) 0.0185(8) -0.0003(6) 0.0031(6) -0.0017(6) C12 0.0210(9) 0.0193(8) 0.0294(10) -0.0012(7) 0.0084(7) 0.0012(7) C2 0.0184(8) 0.0186(8) 0.0180(8) -0.0006(6) 0.0056(6) 0.0004(6) C13 0.0216(9) 0.0208(8) 0.0212(9) -0.0044(7) 0.0040(7) -0.0008(7) C9 0.0273(10) 0.0197(9) 0.0313(10) 0.0004(7) 0.0060(8) -0.0025(7) C8 0.0179(8) 0.0170(8) 0.0203(8) -0.0017(6) 0.0040(6) -0.0016(6) C1 0.0219(9) 0.0216(9) 0.0298(10) -0.0013(7) 0.0084(8) -0.0031(7) C5 0.0202(9) 0.0225(9) 0.0246(9) -0.0018(7) 0.0078(7) 0.0025(7) C6 0.0177(8) 0.0186(8) 0.0162(8) 0.0000(6) 0.0034(6) 0.0006(7) C11 0.0206(9) 0.0193(8) 0.0235(9) -0.0005(7) 0.0017(7) 0.0001(7) C4 0.0246(10) 0.0266(9) 0.0278(10) 0.0006(7) 0.0004(7) 0.0073(7) C3 0.0302(10) 0.0231(9) 0.0205(9) 0.0036(7) 0.0054(7) 0.0030(7) C10 0.0295(10) 0.0251(10) 0.0316(11) 0.0036(7) -0.0002(8) 0.0003(8) _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 1.4345(19) . ? O3 C12 1.4156(19) . ? O2 C9 1.428(2) . ? O2 C10 1.434(2) . ? C14 C13 1.561(2) . ? C14 C7 1.564(2) . ? C14 C2 1.568(2) . ? C7 C8 1.534(2) . ? C7 C6 1.537(2) . ? C12 C13 1.524(2) . ? C12 C11 1.550(2) . ? C2 C1 1.508(2) . ? C2 C3 1.536(2) . ? C2 C6 1.579(2) . ? C13 C8 1.558(2) . ? C9 C8 1.509(2) . ? C8 C11 1.561(2) . ? C5 C6 1.522(2) . ? C5 C4 1.525(2) . ? C11 C10 1.516(2) . ? C4 C3 1.530(2) . ? 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 C9 O2 C10 105.26(13) . . ? C13 C14 C7 90.12(12) . . ? C13 C14 C2 128.73(14) . . ? C7 C14 C2 88.89(11) . . ? C8 C7 C6 121.08(14) . . ? C8 C7 C14 88.99(11) . . ? C6 C7 C14 91.67(11) . . ? O3 C12 C13 120.83(14) . . ? O3 C12 C11 120.53(15) . . ? C13 C12 C11 90.94(12) . . ? C1 C2 C3 111.96(14) . . ? C1 C2 C14 121.46(13) . . ? C3 C2 C14 109.18(14) . . ? C1 C2 C6 116.82(14) . . ? C3 C2 C6 104.62(12) . . ? C14 C2 C6 89.96(11) . . ? C12 C13 C8 89.22(13) . . ? C12 C13 C14 125.58(14) . . ? C8 C13 C14 88.23(12) . . ? O2 C9 C8 106.15(13) . . ? C9 C8 C7 121.85(13) . . ? C9 C8 C13 124.50(14) . . ? C7 C8 C13 91.36(12) . . ? C9 C8 C11 103.79(14) . . ? C7 C8 C11 122.65(14) . . ? C13 C8 C11 89.27(12) . . ? O1 C1 C2 112.07(14) . . ? C6 C5 C4 104.32(13) . . ? C5 C6 C7 113.27(13) . . ? C5 C6 C2 106.00(13) . . ? C7 C6 C2 89.47(11) . . ? C10 C11 C12 115.56(14) . . ? C10 C11 C8 103.45(14) . . ? C12 C11 C8 88.18(12) . . ? C5 C4 C3 102.81(15) . . ? C4 C3 C2 105.31(13) . . ? O2 C10 C11 105.42(15) . . ? 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 C13 C14 C7 C8 -8.63(12) . . . . ? C2 C14 C7 C8 120.10(12) . . . . ? C13 C14 C7 C6 -129.69(13) . . . . ? C2 C14 C7 C6 -0.96(12) . . . . ? C13 C14 C2 C1 -31.7(2) . . . . ? C7 C14 C2 C1 -120.97(16) . . . . ? C13 C14 C2 C3 -164.31(14) . . . . ? C7 C14 C2 C3 106.42(13) . . . . ? C13 C14 C2 C6 90.20(17) . . . . ? C7 C14 C2 C6 0.94(12) . . . . ? O3 C12 C13 C8 138.72(15) . . . . ? C11 C12 C13 C8 11.74(12) . . . . ? O3 C12 C13 C14 51.5(2) . . . . ? C11 C12 C13 C14 -75.53(17) . . . . ? C7 C14 C13 C12 96.28(16) . . . . ? C2 C14 C13 C12 7.6(2) . . . . ? C7 C14 C13 C8 8.50(12) . . . . ? C2 C14 C13 C8 -80.17(17) . . . . ? C10 O2 C9 C8 -38.74(17) . . . . ? O2 C9 C8 C7 165.58(14) . . . . ? O2 C9 C8 C13 -77.0(2) . . . . ? O2 C9 C8 C11 21.82(17) . . . . ? C6 C7 C8 C9 -127.02(16) . . . . ? C14 C7 C8 C9 141.64(16) . . . . ? C6 C7 C8 C13 99.99(15) . . . . ? C14 C7 C8 C13 8.65(12) . . . . ? C6 C7 C8 C11 10.0(2) . . . . ? C14 C7 C8 C11 -81.36(16) . . . . ? C12 C13 C8 C9 94.64(17) . . . . ? C14 C13 C8 C9 -139.73(16) . . . . ? C12 C13 C8 C7 -134.30(13) . . . . ? C14 C13 C8 C7 -8.67(12) . . . . ? C12 C13 C8 C11 -11.65(12) . . . . ? C14 C13 C8 C11 113.98(12) . . . . ? C3 C2 C1 O1 74.81(16) . . . . ? C14 C2 C1 O1 -56.6(2) . . . . ? C6 C2 C1 O1 -164.60(13) . . . . ? C4 C5 C6 C7 69.43(16) . . . . ? C4 C5 C6 C2 -27.05(17) . . . . ? C8 C7 C6 C5 163.90(13) . . . . ? C14 C7 C6 C5 -106.27(14) . . . . ? C8 C7 C6 C2 -88.87(15) . . . . ? C14 C7 C6 C2 0.96(12) . . . . ? C1 C2 C6 C5 -121.09(15) . . . . ? C3 C2 C6 C5 3.32(17) . . . . ? C14 C2 C6 C5 113.15(13) . . . . ? C1 C2 C6 C7 124.81(14) . . . . ? C3 C2 C6 C7 -110.79(14) . . . . ? C14 C2 C6 C7 -0.95(12) . . . . ? O3 C12 C11 C10 117.02(17) . . . . ? C13 C12 C11 C10 -115.77(16) . . . . ? O3 C12 C11 C8 -138.93(15) . . . . ? C13 C12 C11 C8 -11.72(12) . . . . ? C9 C8 C11 C10 1.86(16) . . . . ? C7 C8 C11 C10 -141.53(15) . . . . ? C13 C8 C11 C10 127.32(13) . . . . ? C9 C8 C11 C12 -114.00(13) . . . . ? C7 C8 C11 C12 102.61(15) . . . . ? C13 C8 C11 C12 11.46(12) . . . . ? C6 C5 C4 C3 40.53(17) . . . . ? C5 C4 C3 C2 -38.62(17) . . . . ? C1 C2 C3 C4 149.10(14) . . . . ? C14 C2 C3 C4 -73.50(16) . . . . ? C6 C2 C3 C4 21.66(17) . . . . ? C9 O2 C10 C11 39.85(17) . . . . ? C12 C11 C10 O2 69.71(18) . . . . ? C8 C11 C10 O2 -24.77(17) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.678 _refine_diff_density_min -0.511 _refine_diff_density_rms 0.063