data_1100141 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 O3' _chemical_formula_weight 280.31 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 Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 7.4026(11) _cell_length_b 15.023(2) _cell_length_c 12.3080(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1368.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 369 _cell_measurement_theta_min 3.31 _cell_measurement_theta_max 17.69 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.01 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _diffrn_ambient_temperature 153(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 6715 _diffrn_reflns_av_R_equivalents 0.0855 _diffrn_reflns_av_sigmaI/netI 0.1077 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.14 _diffrn_reflns_theta_max 25.37 _reflns_number_total 2496 _reflns_number_gt 1613 _reflns_threshold_expression >2sigma(I) _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^)+(0.0331P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(2) _refine_ls_number_reflns 2496 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1067 _refine_ls_R_factor_gt 0.0545 _refine_ls_wR_factor_ref 0.1060 _refine_ls_wR_factor_gt 0.0887 _refine_ls_goodness_of_fit_ref 0.983 _refine_ls_restrained_S_all 0.983 _refine_ls_shift/su_max 0.786 _refine_ls_shift/su_mean 0.004 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 0.8283(3) 0.49282(15) 0.4305(2) 0.0253(7) Uani 1 1 d . . . O2 O 1.0978(4) 0.50481(16) 0.5044(2) 0.0305(7) Uani 1 1 d . . . O3 O 0.5090(4) 0.72697(18) 0.1313(2) 0.0409(8) Uani 1 1 d . . . C1 C 0.6411(5) 0.5250(2) 0.4281(3) 0.0208(9) Uani 1 1 d . . . H1 H 0.5818 0.5271 0.5112 0.025 Uiso 1 1 d R . . C2 C 0.5321(5) 0.4576(3) 0.3651(3) 0.0268(10) Uani 1 1 d . . . H2A H 0.4018 0.4681 0.3779 0.032 Uiso 1 1 calc R . . H2B H 0.5615 0.3970 0.3912 0.032 Uiso 1 1 calc R . . C3 C 0.5718(5) 0.4640(2) 0.2438(3) 0.0296(10) Uani 1 1 d . . . H3A H 0.5023 0.4179 0.2044 0.036 Uiso 1 1 calc R . . H3B H 0.7019 0.4532 0.2307 0.036 Uiso 1 1 calc R . . C4 C 0.5203(6) 0.5562(2) 0.2010(3) 0.0296(10) Uani 1 1 d . . . H4A H 0.5751 0.5646 0.1283 0.036 Uiso 1 1 calc R . . H4B H 0.3875 0.5591 0.1924 0.036 Uiso 1 1 calc R . . C5 C 0.5805(5) 0.6314(3) 0.2745(3) 0.0250(10) Uani 1 1 d . . . C6 C 0.6413(5) 0.6165(2) 0.3798(3) 0.0202(9) Uani 1 1 d . . . C7 C 0.7027(5) 0.6881(2) 0.4453(3) 0.0199(9) Uani 1 1 d . . . C8 C 0.6929(5) 0.7738(2) 0.4036(3) 0.0224(9) Uani 1 1 d . . . H8 H 0.7306 0.8226 0.4472 0.027 Uiso 1 1 calc R . . C9 C 0.6292(5) 0.7893(3) 0.3001(3) 0.0278(10) Uani 1 1 d . . . H9 H 0.6234 0.8483 0.2727 0.033 Uiso 1 1 calc R . . C10 C 0.5738(6) 0.7188(3) 0.2362(3) 0.0290(10) Uani 1 1 d . . . C11 C 0.4956(7) 0.8152(3) 0.0873(4) 0.0513(14) Uani 1 1 d . . . H11A H 0.4360 0.8070 -0.0001 0.062 Uiso 1 1 d R . . H11B H 0.4318 0.8577 0.1493 0.062 Uiso 1 1 d R . . H11C H 0.6288 0.8432 0.0706 0.062 Uiso 1 1 d R . . C12 C 0.7686(5) 0.6705(2) 0.5573(3) 0.0218(10) Uani 1 1 d . . . C13 C 0.7307(5) 0.7318(2) 0.6400(3) 0.0241(9) Uani 1 1 d . . . H13 H 0.6676 0.7851 0.6228 0.029 Uiso 1 1 calc R . . C14 C 0.7836(5) 0.7161(2) 0.7467(3) 0.0260(10) Uani 1 1 d . . . H14 H 0.7552 0.7581 0.8019 0.031 Uiso 1 1 calc R . . C15 C 0.8768(5) 0.6400(3) 0.7725(3) 0.0279(10) Uani 1 1 d . . . H15 H 0.9099 0.6286 0.8457 0.033 Uiso 1 1 calc R . . C16 C 0.9224(5) 0.5801(2) 0.6924(3) 0.0244(10) Uani 1 1 d . . . H16 H 0.9900 0.5284 0.7105 0.029 Uiso 1 1 calc R . . C17 C 0.8695(5) 0.5947(2) 0.5837(3) 0.0195(9) Uani 1 1 d . . . C18 C 0.9422(6) 0.5294(2) 0.5038(3) 0.0232(9) Uani 1 1 d . . . 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 0.0252(16) 0.0237(15) 0.0270(15) -0.0037(13) -0.0033(13) 0.0029(12) O2 0.0199(17) 0.0308(17) 0.0406(16) -0.0007(14) -0.0023(14) 0.0070(13) O3 0.056(2) 0.0351(18) 0.0316(18) 0.0132(15) -0.0101(17) -0.0075(14) C1 0.016(2) 0.021(2) 0.025(2) 0.000(2) 0.0005(19) -0.0023(17) C2 0.030(3) 0.026(2) 0.025(2) -0.0016(18) -0.0001(19) -0.0018(19) C3 0.025(2) 0.029(3) 0.035(3) -0.005(2) -0.003(2) -0.0028(18) C4 0.029(3) 0.034(2) 0.026(2) 0.001(2) -0.004(2) -0.003(2) C5 0.026(2) 0.028(3) 0.021(2) -0.0022(19) -0.001(2) -0.0007(17) C6 0.016(2) 0.021(2) 0.023(2) 0.0031(18) 0.0042(18) 0.0006(17) C7 0.019(2) 0.021(2) 0.020(2) 0.0020(19) 0.0009(19) -0.0010(16) C8 0.023(2) 0.018(2) 0.027(2) -0.0046(19) 0.0001(18) 0.0002(17) C9 0.032(3) 0.019(2) 0.032(3) 0.006(2) -0.001(2) -0.0005(19) C10 0.032(3) 0.033(3) 0.021(2) 0.009(2) -0.003(2) 0.0000(19) C11 0.073(4) 0.042(3) 0.040(3) 0.018(3) -0.013(3) -0.009(3) C12 0.020(2) 0.022(2) 0.022(2) -0.0007(19) -0.0022(19) -0.0036(18) C13 0.021(2) 0.023(2) 0.029(2) 0.000(2) -0.001(2) -0.0010(17) C14 0.025(2) 0.027(2) 0.026(2) -0.005(2) -0.002(2) -0.0034(19) C15 0.026(3) 0.035(3) 0.023(2) 0.004(2) -0.003(2) -0.007(2) C16 0.020(2) 0.022(2) 0.032(2) 0.003(2) -0.002(2) -0.0038(17) C17 0.017(2) 0.019(2) 0.023(2) 0.0007(18) -0.0019(18) 0.0005(17) C18 0.028(3) 0.016(2) 0.025(2) 0.006(2) -0.006(2) -0.0020(18) _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 C18 1.351(4) . ? O1 C1 1.468(4) . ? O2 C18 1.209(4) . ? O3 C10 1.383(4) . ? O3 C11 1.435(5) . ? C1 C6 1.497(4) . ? C1 C2 1.509(5) . ? C2 C3 1.526(5) . ? C3 C4 1.530(5) . ? C4 C5 1.515(5) . ? C5 C6 1.391(5) . ? C5 C10 1.395(5) . ? C6 C7 1.418(5) . ? C7 C8 1.388(5) . ? C7 C12 1.486(5) . ? C8 C9 1.379(5) . ? C9 C10 1.381(5) . ? C12 C17 1.400(5) . ? C12 C13 1.401(5) . ? C13 C14 1.391(5) . ? C14 C15 1.373(5) . ? C15 C16 1.376(5) . ? C16 C17 1.412(5) . ? C17 C18 1.490(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 C18 O1 C1 118.0(3) . . ? C10 O3 C11 117.3(3) . . ? O1 C1 C6 108.1(3) . . ? O1 C1 C2 107.1(3) . . ? C6 C1 C2 114.4(3) . . ? C1 C2 C3 110.9(3) . . ? C2 C3 C4 110.2(3) . . ? C5 C4 C3 113.4(3) . . ? C6 C5 C10 118.5(3) . . ? C6 C5 C4 122.1(3) . . ? C10 C5 C4 119.4(3) . . ? C5 C6 C7 120.7(3) . . ? C5 C6 C1 121.2(3) . . ? C7 C6 C1 118.1(3) . . ? C8 C7 C6 118.5(3) . . ? C8 C7 C12 121.6(3) . . ? C6 C7 C12 119.9(3) . . ? C9 C8 C7 121.0(3) . . ? C8 C9 C10 119.9(3) . . ? C9 C10 O3 124.5(4) . . ? C9 C10 C5 121.3(3) . . ? O3 C10 C5 114.3(4) . . ? C17 C12 C13 118.2(3) . . ? C17 C12 C7 122.3(3) . . ? C13 C12 C7 119.4(3) . . ? C14 C13 C12 121.2(4) . . ? C15 C14 C13 120.0(4) . . ? C14 C15 C16 120.2(4) . . ? C15 C16 C17 120.6(3) . . ? C12 C17 C16 119.6(3) . . ? C12 C17 C18 125.1(3) . . ? C16 C17 C18 115.0(3) . . ? O2 C18 O1 118.3(4) . . ? O2 C18 C17 122.8(4) . . ? O1 C18 C17 118.8(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.37 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.222 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.050