data_ef1310m _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 O4' _chemical_formula_weight 302.36 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 7.0650(4) _cell_length_b 26.7547(14) _cell_length_c 8.9248(5) _cell_angle_alpha 90.00 _cell_angle_beta 92.108(1) _cell_angle_gamma 90.00 _cell_volume 1685.84(16) _cell_formula_units_Z 4 _cell_measurement_temperature 180(1) _cell_measurement_reflns_used 7407 _cell_measurement_theta_min 2.41 _cell_measurement_theta_max 30.01 _exptl_crystal_description 'Needle plate fragment' _exptl_crystal_colour 'Colourless' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.31 _exptl_crystal_size_min 0.11 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.191 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.083 _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 180(1) _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' _diffrn_measurement_method 'Omega' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13687 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 30.05 _reflns_number_total 4896 _reflns_number_gt 3830 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART' _computing_cell_refinement 'SAINT' _computing_data_reduction 'SAINT' _computing_structure_solution 'SHELXTL' _computing_structure_refinement 'SHELXTL' _computing_molecular_graphics 'SHELXTL' _computing_publication_material '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^)+(0.0100P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0134(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4896 _refine_ls_number_parameters 206 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.0841 _refine_ls_wR_factor_gt 0.0825 _refine_ls_goodness_of_fit_ref 1.768 _refine_ls_restrained_S_all 1.768 _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 -0.21071(10) 0.39393(3) 0.71340(9) 0.0323(2) Uani 1 1 d . . . C2 C -0.18008(14) 0.43477(4) 0.61083(13) 0.0275(2) Uani 1 1 d . . . O3 O 0.02059(10) 0.44606(3) 0.61332(9) 0.02890(19) Uani 1 1 d . . . C4 C 0.14372(15) 0.40785(4) 0.59153(12) 0.0261(2) Uani 1 1 d . . . C5 C 0.06498(14) 0.35650(4) 0.60832(12) 0.0252(2) Uani 1 1 d . . . C6 C -0.09739(15) 0.35306(4) 0.70957(13) 0.0295(3) Uani 1 1 d . . . C7 C -0.27583(16) 0.47934(4) 0.67776(15) 0.0375(3) Uani 1 1 d . . . H7X H -0.4119 0.4728 0.6831 0.056 Uiso 1 1 calc R . . H7Y H -0.2559 0.5088 0.6149 0.056 Uiso 1 1 calc R . . H7Z H -0.2220 0.4855 0.7789 0.056 Uiso 1 1 calc R . . C8 C -0.25149(15) 0.42285(5) 0.45304(13) 0.0359(3) Uani 1 1 d . . . C8X H -0.1832 0.3938 0.4156 0.054 Uiso 1 1 calc R . . H8Y H -0.2302 0.4516 0.3879 0.054 Uiso 1 1 calc R . . H8Z H -0.3873 0.4154 0.4534 0.054 Uiso 1 1 calc R . . O9 O 0.30737(10) 0.41808(3) 0.57272(9) 0.0353(2) Uani 1 1 d . . . O10 O -0.13051(12) 0.31835(3) 0.79105(10) 0.0429(2) Uani 1 1 d . . . C11 C 0.14394(15) 0.31570(4) 0.54565(12) 0.0274(2) Uani 1 1 d . . . C12 C 0.29701(15) 0.31934(4) 0.43490(13) 0.0274(2) Uani 1 1 d . . . C13 C 0.27015(15) 0.34770(4) 0.30375(12) 0.0270(2) Uani 1 1 d . . . H13 H 0.1567 0.3665 0.2898 0.032 Uiso 1 1 calc R . . C14 C 0.40445(15) 0.34931(4) 0.19303(12) 0.0266(2) Uani 1 1 d . . . C15 C 0.57002(15) 0.32109(4) 0.21822(13) 0.0310(3) Uani 1 1 d . . . H15 H 0.6646 0.3215 0.1453 0.037 Uiso 1 1 calc R . . C16 C 0.59896(16) 0.29274(4) 0.34683(14) 0.0352(3) Uani 1 1 d . . . H16 H 0.7126 0.2741 0.3610 0.042 Uiso 1 1 calc R . . C17 C 0.46278(16) 0.29142(4) 0.45547(14) 0.0337(3) Uani 1 1 d . . . H17 H 0.4825 0.2716 0.5431 0.040 Uiso 1 1 calc R . . C18 C 0.37833(16) 0.38073(4) 0.04963(13) 0.0314(3) Uani 1 1 d . . . C19 C 0.40915(17) 0.34800(5) -0.08911(14) 0.0384(3) Uani 1 1 d . . . H19X H 0.5334 0.3318 -0.0794 0.058 Uiso 1 1 calc R . . H19Y H 0.4037 0.3689 -0.1793 0.058 Uiso 1 1 calc R . . H19Z H 0.3100 0.3224 -0.0970 0.058 Uiso 1 1 calc R . . C20 C 0.18006(18) 0.40400(5) 0.03384(15) 0.0432(3) Uani 1 1 d . . . H20X H 0.0846 0.3774 0.0305 0.065 Uiso 1 1 calc R . . H20Y H 0.1698 0.4236 -0.0589 0.065 Uiso 1 1 calc R . . H20Z H 0.1592 0.4258 0.1198 0.065 Uiso 1 1 calc R . . C21 C 0.52649(19) 0.42319(5) 0.05540(15) 0.0460(3) Uani 1 1 d . . . H21X H 0.5093 0.4436 0.1450 0.069 Uiso 1 1 calc R . . H21Y H 0.5101 0.4441 -0.0343 0.069 Uiso 1 1 calc R . . H21Z H 0.6541 0.4088 0.0591 0.069 Uiso 1 1 calc R . . C22 C 0.08065(17) 0.26285(4) 0.57477(15) 0.0397(3) Uani 1 1 d . . . H22X H 0.1733 0.2463 0.6425 0.059 Uiso 1 1 calc R . . H22Y H 0.0706 0.2445 0.4798 0.059 Uiso 1 1 calc R . . H22Z H -0.0431 0.2634 0.6209 0.059 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 0.0342(4) 0.0280(4) 0.0356(5) 0.0052(4) 0.0125(4) 0.0010(3) C2 0.0260(5) 0.0263(6) 0.0306(6) 0.0038(5) 0.0062(5) -0.0022(4) O3 0.0270(4) 0.0255(4) 0.0343(5) 0.0001(3) 0.0028(3) -0.0027(3) C4 0.0295(6) 0.0287(6) 0.0202(6) 0.0018(5) 0.0012(4) -0.0009(4) C5 0.0265(5) 0.0267(6) 0.0226(6) 0.0039(5) 0.0029(4) -0.0016(4) C6 0.0318(6) 0.0269(6) 0.0301(7) 0.0014(5) 0.0049(5) -0.0020(5) C7 0.0395(7) 0.0297(6) 0.0441(8) 0.0012(6) 0.0128(6) 0.0026(5) C8 0.0286(6) 0.0438(7) 0.0351(7) -0.0003(6) -0.0008(5) 0.0008(5) O9 0.0269(4) 0.0367(5) 0.0425(5) 0.0040(4) 0.0047(4) -0.0046(3) O10 0.0475(5) 0.0352(5) 0.0471(6) 0.0149(4) 0.0188(4) 0.0010(4) C11 0.0302(6) 0.0291(6) 0.0229(6) 0.0048(5) -0.0008(4) 0.0004(5) C12 0.0317(6) 0.0249(6) 0.0257(6) -0.0001(5) 0.0039(5) 0.0013(4) C13 0.0281(5) 0.0264(6) 0.0265(6) 0.0004(5) 0.0006(5) 0.0030(4) C14 0.0309(6) 0.0254(6) 0.0235(6) -0.0030(5) 0.0015(5) -0.0019(4) C15 0.0304(6) 0.0330(6) 0.0299(7) -0.0037(5) 0.0060(5) 0.0015(5) C16 0.0323(6) 0.0356(7) 0.0376(7) 0.0000(6) 0.0021(5) 0.0102(5) C17 0.0387(6) 0.0312(6) 0.0311(7) 0.0055(5) 0.0005(5) 0.0072(5) C18 0.0369(6) 0.0333(6) 0.0242(6) 0.0023(5) 0.0034(5) -0.0002(5) C19 0.0450(7) 0.0457(7) 0.0247(7) 0.0005(6) 0.0047(5) -0.0007(6) C20 0.0525(8) 0.0482(8) 0.0290(7) 0.0084(6) 0.0005(6) 0.0125(6) C21 0.0591(8) 0.0402(8) 0.0387(8) 0.0062(6) 0.0025(6) -0.0097(6) C22 0.0488(7) 0.0279(6) 0.0428(8) 0.0030(6) 0.0098(6) -0.0005(5) _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 C6 1.3564(12) . ? O1 C2 1.4467(12) . ? C2 O3 1.4489(12) . ? C2 C7 1.5054(15) . ? C2 C8 1.5124(16) . ? O3 C4 1.3611(12) . ? C4 O9 1.2059(12) . ? C4 C5 1.4916(14) . ? C5 C11 1.3561(15) . ? C5 C6 1.4890(15) . ? C6 O10 1.2077(13) . ? C11 C12 1.4949(15) . ? C11 C22 1.5084(15) . ? C12 C17 1.3956(14) . ? C12 C13 1.4019(15) . ? C13 C14 1.3955(15) . ? C14 C15 1.4033(14) . ? C14 C18 1.5367(15) . ? C15 C16 1.3847(16) . ? C16 C17 1.3913(16) . ? C18 C20 1.5347(16) . ? C18 C19 1.5385(16) . ? C18 C21 1.5443(16) . ? 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 C6 O1 C2 119.39(8) . . ? O1 C2 O3 108.47(8) . . ? O1 C2 C7 105.50(9) . . ? O3 C2 C7 106.41(9) . . ? O1 C2 C8 112.18(9) . . ? O3 C2 C8 110.55(9) . . ? C7 C2 C8 113.40(10) . . ? C4 O3 C2 118.12(8) . . ? O9 C4 O3 118.06(10) . . ? O9 C4 C5 125.88(10) . . ? O3 C4 C5 115.77(9) . . ? C11 C5 C6 122.57(10) . . ? C11 C5 C4 122.64(10) . . ? C6 C5 C4 114.61(9) . . ? O10 C6 O1 118.50(10) . . ? O10 C6 C5 125.70(10) . . ? O1 C6 C5 115.72(9) . . ? C5 C11 C12 122.60(10) . . ? C5 C11 C22 123.68(10) . . ? C12 C11 C22 113.66(10) . . ? C17 C12 C13 119.13(10) . . ? C17 C12 C11 120.14(10) . . ? C13 C12 C11 120.55(9) . . ? C14 C13 C12 122.22(10) . . ? C13 C14 C15 117.03(10) . . ? C13 C14 C18 122.86(10) . . ? C15 C14 C18 120.10(10) . . ? C16 C15 C14 121.62(10) . . ? C15 C16 C17 120.45(11) . . ? C16 C17 C12 119.55(11) . . ? C20 C18 C14 112.31(9) . . ? C20 C18 C19 108.22(10) . . ? C14 C18 C19 110.04(9) . . ? C20 C18 C21 108.65(10) . . ? C14 C18 C21 108.31(9) . . ? C19 C18 C21 109.25(10) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.338 _refine_diff_density_min -0.232 _refine_diff_density_rms 0.042