# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1531 data_fb02sad _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H18 O5' _chemical_formula_weight 278.29 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 9.1424(4) _cell_length_b 11.5049(5) _cell_length_c 13.4460(6) _cell_angle_alpha 90.00 _cell_angle_beta 101.2810(10) _cell_angle_gamma 90.00 _cell_volume 1386.96(11) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3562 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25 _exptl_crystal_description Equant _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.7729 _exptl_absorpt_correction_T_max 0.9623 _exptl_absorpt_process_details ? _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 7828 _diffrn_reflns_av_R_equivalents 0.0347 _diffrn_reflns_av_sigmaI/netI 0.0413 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_theta_min 2.35 _diffrn_reflns_theta_max 27.95 _reflns_number_total 3010 _reflns_number_gt 1959 _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^)+(0.0656P)^2^+0.3207P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.012(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3010 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0851 _refine_ls_R_factor_gt 0.0510 _refine_ls_wR_factor_ref 0.1444 _refine_ls_wR_factor_gt 0.1249 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 -0.37853(15) 0.88172(12) 0.03211(10) 0.0533(4) Uani 1 1 d . . . O2 O 0.04269(15) 0.71751(12) 0.26070(11) 0.0523(4) Uani 1 1 d . . . O3 O 0.17204(17) 0.88092(14) 0.25460(15) 0.0770(6) Uani 1 1 d . . . O4 O -0.15044(16) 0.79369(12) 0.02774(10) 0.0516(4) Uani 1 1 d . . . O5 O -0.0267(2) 1.09451(14) 0.31340(14) 0.0771(6) Uani 1 1 d . . . C1 C -0.4704(2) 0.87749(19) 0.10919(16) 0.0525(6) Uani 1 1 d . . . C2 C -0.2228(2) 0.87608(17) 0.07879(15) 0.0440(5) Uani 1 1 d . . . C3 C -0.1501(2) 0.99021(19) 0.06277(17) 0.0539(6) Uani 1 1 d . . . C4 C -0.0798(2) 1.05615(18) 0.13838(19) 0.0575(6) Uani 1 1 d . . . C5 C -0.0614(2) 1.02345(18) 0.24570(18) 0.0510(5) Uani 1 1 d . . . C6 C -0.0875(2) 0.89497(16) 0.26761(14) 0.0400(5) Uani 1 1 d . . . C7 C -0.1181(2) 0.87336(19) 0.37577(15) 0.0495(5) Uani 1 1 d . . . C8 C -0.2804(2) 0.87264(17) 0.38634(15) 0.0464(5) Uani 1 1 d . . . C9 C -0.3936(2) 0.88938(17) 0.30889(16) 0.0479(5) Uani 1 1 d . . . C10 C -0.3642(2) 0.91513(16) 0.20521(15) 0.0442(5) Uani 1 1 d . . . C11 C -0.22215(19) 0.85248(15) 0.19017(14) 0.0379(4) Uani 1 1 d . . . C12 C 0.0571(2) 0.83223(17) 0.25846(15) 0.0436(5) Uani 1 1 d . . . C13 C 0.1770(3) 0.6492(2) 0.26489(18) 0.0634(7) Uani 1 1 d . . . C14 C -0.3014(3) 0.8502(2) 0.49275(18) 0.0672(7) Uani 1 1 d . . . C15 C -0.2053(3) 0.6767(2) 0.02753(18) 0.0613(6) Uani 1 1 d . . . H1A H -0.5072 0.7900 0.1200 0.080 Uiso 1 1 d . . . H1B H -0.5545 0.9322 0.0800 0.080 Uiso 1 1 d . . . H3A H -0.1601 1.0198 -0.0008 0.080 Uiso 1 1 d . . . H4A H -0.0408 1.1256 0.1200 0.080 Uiso 1 1 d . . . H7A H -0.0633 0.9315 0.4197 0.080 Uiso 1 1 d . . . H7B H -0.0734 0.7939 0.3997 0.080 Uiso 1 1 d . . . H9A H -0.4966 0.8894 0.3200 0.080 Uiso 1 1 d . . . H10A H -0.3507 0.9993 0.2009 0.080 Uiso 1 1 d . . . H11A H -0.2385 0.7683 0.1983 0.080 Uiso 1 1 d . . . H13A H 0.2354 0.6805 0.2216 0.080 Uiso 1 1 d . . . H13B H 0.2524 0.6706 0.3220 0.080 Uiso 1 1 d . . . H13C H 0.1478 0.5827 0.2408 0.080 Uiso 1 1 d . . . H14A H -0.2433 0.9016 0.5380 0.080 Uiso 1 1 d . . . H14B H -0.4050 0.8440 0.5003 0.080 Uiso 1 1 d . . . H14C H -0.2753 0.7755 0.5215 0.080 Uiso 1 1 d . . . H15A H -0.1526 0.6356 0.0789 0.080 Uiso 1 1 d . . . H15B H -0.2019 0.6320 -0.0413 0.080 Uiso 1 1 d . . . H15C H -0.3106 0.6746 0.0412 0.080 Uiso 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 0.0430(8) 0.0680(10) 0.0450(8) 0.0092(7) -0.0009(6) 0.0065(7) O2 0.0409(8) 0.0484(8) 0.0662(10) 0.0009(7) 0.0065(7) 0.0087(6) O3 0.0389(9) 0.0657(11) 0.1296(16) 0.0098(10) 0.0243(9) -0.0023(7) O4 0.0530(9) 0.0552(9) 0.0482(8) -0.0016(7) 0.0136(7) 0.0039(7) O5 0.0821(12) 0.0547(10) 0.0899(13) -0.0216(9) 0.0055(10) -0.0108(8) C1 0.0367(11) 0.0643(13) 0.0532(13) 0.0137(10) 0.0006(9) 0.0068(9) C2 0.0394(10) 0.0470(11) 0.0438(11) 0.0048(9) 0.0037(8) 0.0032(8) C3 0.0491(12) 0.0534(12) 0.0602(13) 0.0179(11) 0.0132(10) 0.0032(10) C4 0.0523(13) 0.0421(11) 0.0792(17) 0.0122(11) 0.0157(12) -0.0028(10) C5 0.0372(11) 0.0452(11) 0.0688(14) -0.0060(11) 0.0057(10) -0.0005(9) C6 0.0322(9) 0.0431(10) 0.0432(11) -0.0017(8) 0.0038(8) 0.0016(7) C7 0.0399(11) 0.0640(13) 0.0429(11) -0.0041(10) 0.0040(9) -0.0004(9) C8 0.0449(11) 0.0494(12) 0.0458(11) -0.0012(9) 0.0112(9) 0.0018(9) C9 0.0387(10) 0.0511(12) 0.0554(13) 0.0021(10) 0.0130(9) 0.0047(9) C10 0.0358(10) 0.0441(11) 0.0515(12) 0.0057(9) 0.0059(8) 0.0044(8) C11 0.0324(9) 0.0379(10) 0.0423(10) 0.0025(8) 0.0048(8) 0.0009(7) C12 0.0348(10) 0.0495(12) 0.0450(11) 0.0025(9) 0.0037(8) 0.0018(8) C13 0.0550(14) 0.0674(15) 0.0668(15) -0.0061(12) 0.0096(11) 0.0220(11) C14 0.0610(15) 0.0922(18) 0.0501(14) 0.0051(12) 0.0154(11) -0.0042(13) C15 0.0625(14) 0.0539(13) 0.0653(15) -0.0126(11) 0.0073(11) -0.0003(11) _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 C2 1.441(2) . ? O1 C1 1.457(3) . ? O2 C12 1.327(2) . ? O2 C13 1.450(2) . ? O3 C12 1.201(2) . ? O4 C2 1.409(2) . ? O4 C15 1.436(3) . ? O5 C5 1.218(2) . ? C1 C10 1.518(3) . ? C2 C3 1.506(3) . ? C2 C11 1.521(3) . ? C3 C4 1.329(3) . ? C4 C5 1.469(3) . ? C5 C6 1.535(3) . ? C6 C11 1.529(2) . ? C6 C12 1.532(3) . ? C6 C7 1.554(3) . ? C7 C8 1.518(3) . ? C8 C9 1.331(3) . ? C8 C14 1.503(3) . ? C9 C10 1.500(3) . ? C10 C11 1.533(3) . ? 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 O1 C1 110.28(14) . . ? C12 O2 C13 116.92(17) . . ? C2 O4 C15 115.75(16) . . ? O1 C1 C10 103.54(16) . . ? O4 C2 O1 109.65(15) . . ? O4 C2 C3 104.76(16) . . ? O1 C2 C3 108.92(15) . . ? O4 C2 C11 116.61(15) . . ? O1 C2 C11 104.48(15) . . ? C3 C2 C11 112.32(17) . . ? C4 C3 C2 123.31(19) . . ? C3 C4 C5 123.42(19) . . ? O5 C5 C4 121.7(2) . . ? O5 C5 C6 122.0(2) . . ? C4 C5 C6 116.29(18) . . ? C11 C6 C12 112.78(15) . . ? C11 C6 C5 108.17(15) . . ? C12 C6 C5 105.64(16) . . ? C11 C6 C7 108.52(15) . . ? C12 C6 C7 108.42(15) . . ? C5 C6 C7 113.38(17) . . ? C8 C7 C6 116.54(16) . . ? C9 C8 C14 123.1(2) . . ? C9 C8 C7 123.40(19) . . ? C14 C8 C7 113.53(17) . . ? C8 C9 C10 120.20(18) . . ? C9 C10 C1 122.23(17) . . ? C9 C10 C11 109.87(15) . . ? C1 C10 C11 99.83(16) . . ? C2 C11 C6 117.44(15) . . ? C2 C11 C10 101.88(15) . . ? C6 C11 C10 110.50(15) . . ? O3 C12 O2 123.81(19) . . ? O3 C12 C6 124.03(19) . . ? O2 C12 C6 112.07(16) . . ? _diffrn_measured_fraction_theta_max 0.904 _diffrn_reflns_theta_full 27.95 _diffrn_measured_fraction_theta_full 0.904 _refine_diff_density_max 0.233 _refine_diff_density_min -0.175 _refine_diff_density_rms 0.039