# Supplementary Material (ESI) for Green Chemistry # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 1048/ data_compound3a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H14 O6' _chemical_formula_sum 'C14 H14 O6' _chemical_formula_weight 278.25 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 'triclinic' _symmetry_space_group_name_H-M 'P1(bar)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.9637(2) _cell_length_b 9.1230(6) _cell_length_c 12.0646(7) _cell_angle_alpha 99.666(3) _cell_angle_beta 96.329(3) _cell_angle_gamma 95.837(3) _cell_volume 638.28(6) _cell_formula_units_Z 2 _cell_measurement_temperature 123(2) _exptl_crystal_description 'needles' _exptl_crystal_colour 'bright yellow' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.448 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 0.114 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9557 _exptl_absorpt_correction_T_max 0.9831 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(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 'Enraf Nonius Kappa CCD' _diffrn_measurement_method '1 degree, phi and omega scans' _diffrn_reflns_number 2985 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0539 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.46 _diffrn_reflns_theta_max 28.24 _reflns_number_total 2985 _reflns_number_gt 2221 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows v 1.05' _computing_publication_material ? _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^)+(0.0396P)^2^+0.2134P] 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 2985 _refine_ls_number_parameters 188 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0947 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.038 _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 O3 O 0.05678(17) 0.27752(12) 0.24409(9) 0.0213(3) Uani 1 1 d . . . O1 O -0.20734(17) -0.15471(12) -0.04524(9) 0.0203(3) Uani 1 1 d D . . O2 O -0.50505(18) -0.38230(12) -0.15704(9) 0.0227(3) Uani 1 1 d . . . O6 O -0.29233(18) -0.13961(12) 0.35860(9) 0.0222(3) Uani 1 1 d . . . O4 O -0.07286(17) 0.29472(12) 0.40866(8) 0.0186(2) Uani 1 1 d . . . O5 O -0.24906(17) 0.08355(12) 0.46788(8) 0.0184(2) Uani 1 1 d . . . C2 C -0.3954(2) -0.19420(16) 0.00128(12) 0.0150(3) Uani 1 1 d . . . C1 C -0.4262(2) -0.11456(16) 0.10688(12) 0.0156(3) Uani 1 1 d . . . C3 C -0.5575(2) -0.31477(16) -0.05466(12) 0.0166(3) Uani 1 1 d . . . C4 C -0.7497(3) -0.35206(18) -0.00656(13) 0.0210(3) Uani 1 1 d . . . H4 H -0.8581 -0.4339 -0.0438 0.025 Uiso 1 1 calc R . . C10 C -0.0643(2) 0.21957(17) 0.30289(12) 0.0160(3) Uani 1 1 d . . . C7 C -0.2596(2) 0.01339(17) 0.15931(12) 0.0160(3) Uani 1 1 d . . . H7 H -0.1802 0.0618 0.1087 0.019 Uiso 1 1 calc R . . C14 C -0.2588(2) -0.00590(17) 0.36520(12) 0.0168(3) Uani 1 1 d . . . C6 C -0.6261(2) -0.15277(18) 0.15312(13) 0.0190(3) Uani 1 1 d . . . H6 H -0.6517 -0.0976 0.2237 0.023 Uiso 1 1 calc R . . C9 C -0.2038(2) 0.07175(16) 0.27066(12) 0.0157(3) Uani 1 1 d . . . C11 C -0.2490(2) 0.24259(17) 0.47160(12) 0.0171(3) Uani 1 1 d . . . C5 C -0.7847(3) -0.26902(18) 0.09714(13) 0.0214(3) Uani 1 1 d . . . H5 H -0.9193 -0.2931 0.1292 0.026 Uiso 1 1 calc R . . C8 C -0.6446(3) -0.51737(18) -0.21197(13) 0.0227(3) Uani 1 1 d . . . H8A H -0.6419 -0.5912 -0.1617 0.034 Uiso 1 1 calc R . . H8B H -0.5865 -0.5574 -0.2823 0.034 Uiso 1 1 calc R . . H8C H -0.8011 -0.4961 -0.2296 0.034 Uiso 1 1 calc R . . C12 C -0.1775(3) 0.31593(19) 0.59315(13) 0.0222(3) Uani 1 1 d . . . H12A H -0.2914 0.2839 0.6397 0.033 Uiso 1 1 calc R . . H12B H -0.1644 0.4250 0.5993 0.033 Uiso 1 1 calc R . . H12C H -0.0302 0.2867 0.6197 0.033 Uiso 1 1 calc R . . C13 C -0.4789(3) 0.27633(19) 0.42318(13) 0.0221(3) Uani 1 1 d . . . H13A H -0.5122 0.2282 0.3432 0.033 Uiso 1 1 calc R . . H13B H -0.4776 0.3849 0.4294 0.033 Uiso 1 1 calc R . . H13C H -0.5958 0.2378 0.4655 0.033 Uiso 1 1 calc R . . H1 H -0.201(4) -0.215(2) -0.1172(15) 0.053(6) Uiso 1 1 d 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 O3 0.0228(6) 0.0211(6) 0.0194(6) 0.0016(5) 0.0078(4) -0.0025(4) O1 0.0199(5) 0.0216(6) 0.0177(6) 0.0000(5) 0.0061(4) -0.0027(4) O2 0.0281(6) 0.0203(6) 0.0163(6) -0.0021(4) 0.0049(4) -0.0061(5) O6 0.0290(6) 0.0152(6) 0.0215(6) 0.0038(5) 0.0006(4) 0.0002(5) O4 0.0212(5) 0.0172(6) 0.0158(5) -0.0014(4) 0.0063(4) -0.0023(4) O5 0.0243(6) 0.0155(6) 0.0151(5) 0.0025(4) 0.0024(4) 0.0018(4) C2 0.0158(7) 0.0151(7) 0.0152(7) 0.0063(6) 0.0024(5) 0.0018(6) C1 0.0170(7) 0.0144(7) 0.0154(7) 0.0040(6) 0.0009(5) 0.0012(6) C3 0.0216(8) 0.0144(8) 0.0130(7) 0.0025(6) 0.0005(5) 0.0011(6) C4 0.0205(8) 0.0216(8) 0.0187(8) 0.0035(6) -0.0003(6) -0.0050(6) C10 0.0168(7) 0.0158(8) 0.0144(7) 0.0000(6) 0.0011(5) 0.0021(6) C7 0.0161(7) 0.0149(8) 0.0170(7) 0.0019(6) 0.0029(5) 0.0032(6) C14 0.0150(7) 0.0177(8) 0.0165(7) 0.0013(6) -0.0002(5) 0.0016(6) C6 0.0206(8) 0.0217(8) 0.0145(7) 0.0034(6) 0.0030(6) 0.0019(6) C9 0.0154(7) 0.0145(8) 0.0169(7) 0.0012(6) 0.0029(5) 0.0020(6) C11 0.0204(8) 0.0163(8) 0.0153(7) 0.0033(6) 0.0057(6) 0.0010(6) C5 0.0184(8) 0.0265(9) 0.0202(8) 0.0071(7) 0.0047(6) -0.0011(6) C8 0.0297(9) 0.0160(8) 0.0190(8) -0.0004(6) -0.0003(6) -0.0027(6) C12 0.0270(8) 0.0215(9) 0.0165(8) -0.0007(6) 0.0041(6) 0.0013(6) C13 0.0240(8) 0.0251(9) 0.0192(8) 0.0051(7) 0.0064(6) 0.0066(7) _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 O3 C10 1.2105(17) . ? O1 C2 1.3519(17) . ? O2 C3 1.3681(18) . ? O2 C8 1.4304(18) . ? O6 C14 1.2035(18) . ? O4 C10 1.3522(17) . ? O4 C11 1.4496(17) . ? O5 C14 1.3561(18) . ? O5 C11 1.4440(18) . ? C2 C1 1.397(2) . ? C2 C3 1.411(2) . ? C1 C6 1.408(2) . ? C1 C7 1.459(2) . ? C3 C4 1.379(2) . ? C4 C5 1.398(2) . ? C10 C9 1.479(2) . ? C7 C9 1.351(2) . ? C14 C9 1.489(2) . ? C6 C5 1.375(2) . ? C11 C12 1.501(2) . ? C11 C13 1.512(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 C3 O2 C8 117.05(12) . . ? C10 O4 C11 118.45(11) . . ? C14 O5 C11 118.12(11) . . ? O1 C2 C1 118.90(13) . . ? O1 C2 C3 120.91(13) . . ? C1 C2 C3 120.19(13) . . ? C2 C1 C6 118.65(13) . . ? C2 C1 C7 118.30(13) . . ? C6 C1 C7 122.80(13) . . ? O2 C3 C4 126.17(13) . . ? O2 C3 C2 113.75(13) . . ? C4 C3 C2 120.05(14) . . ? C3 C4 C5 119.80(14) . . ? O3 C10 O4 117.83(13) . . ? O3 C10 C9 126.09(13) . . ? O4 C10 C9 116.07(12) . . ? C9 C7 C1 128.19(14) . . ? O6 C14 O5 118.93(13) . . ? O6 C14 C9 125.09(14) . . ? O5 C14 C9 115.70(13) . . ? C5 C6 C1 120.69(14) . . ? C7 C9 C10 118.40(13) . . ? C7 C9 C14 124.96(14) . . ? C10 C9 C14 116.50(12) . . ? O5 C11 O4 108.89(11) . . ? O5 C11 C12 106.33(12) . . ? O4 C11 C12 106.17(12) . . ? O5 C11 C13 110.61(12) . . ? O4 C11 C13 110.79(12) . . ? C12 C11 C13 113.80(13) . . ? C6 C5 C4 120.55(14) . . ? _diffrn_measured_fraction_theta_max 0.950 _diffrn_reflns_theta_full 28.24 _diffrn_measured_fraction_theta_full 0.950 _refine_diff_density_max 0.219 _refine_diff_density_min -0.294 _refine_diff_density_rms 0.054 #===END data_compound4a _audit_creation_method SHELXL-97 _chemical_name_systematic ; 8-methoxy,3-carboxy-coumarin ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C11 H8 O5' _chemical_formula_sum 'C11 H8 O5' _chemical_formula_weight 220.17 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 'monclinic' _symmetry_space_group_name_H-M 'P21/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 5.1100(2) _cell_length_b 19.5292(4) _cell_length_c 9.4299(3) _cell_angle_alpha 90.00 _cell_angle_beta 99.909(2) _cell_angle_gamma 90.00 _cell_volume 927.01(5) _cell_formula_units_Z 4 _cell_measurement_temperature 123(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description block _exptl_crystal_colour 'very pale yellow ' _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.578 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.127 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9569 _exptl_absorpt_correction_T_max 0.9874 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 123(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_reflns_number 4155 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_sigmaI/netI 0.0453 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.82 _diffrn_reflns_theta_max 28.33 _reflns_number_total 2151 _reflns_number_gt 1583 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for Windows v 1.05' _computing_publication_material ? _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. The carboxylic acid group was disordered and averaged C-O bond lengths result. The two largest peaks appear in electron the final electron density difference map are 0.8-0.9 angstroms from the oxygen atoms but no carboxylic hydrogen atoms were included in the final refinement. ; _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^)+(0.0546P)^2^+0.3692P] 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 2151 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0690 _refine_ls_R_factor_gt 0.0437 _refine_ls_wR_factor_ref 0.1157 _refine_ls_wR_factor_gt 0.1040 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 0.2382(2) 0.34577(6) 0.72946(11) 0.0165(3) Uani 1 1 d . . . O4 O 0.7291(2) 0.44755(6) 0.47706(12) 0.0218(3) Uani 1 1 d . . . O5 O 0.9663(2) 0.49162(6) 0.67781(12) 0.0215(3) Uani 1 1 d . . . O2 O -0.0642(2) 0.28024(6) 0.88021(12) 0.0202(3) Uani 1 1 d . . . C9 C 0.6016(3) 0.42166(8) 0.70294(17) 0.0138(3) Uani 1 1 d . . . O3 O 0.3122(3) 0.36542(7) 0.51056(12) 0.0260(3) Uani 1 1 d . . . C1 C 0.4875(3) 0.40027(8) 0.93932(17) 0.0144(3) Uani 1 1 d . . . C4 C 0.1708(3) 0.33057(9) 1.10442(17) 0.0180(4) Uani 1 1 d . . . H4 H 0.0653 0.3067 1.1620 0.022 Uiso 1 1 calc R . . C3 C 0.1245(3) 0.32105(8) 0.95636(17) 0.0156(4) Uani 1 1 d . . . C11 C 0.7751(3) 0.45563(8) 0.61231(17) 0.0148(3) Uani 1 1 d . . . C8 C 0.6469(3) 0.43215(8) 0.84673(17) 0.0147(4) Uani 1 1 d . . . H11 H 0.7883 0.4614 0.8877 0.018 Uiso 1 1 calc R . . C6 C 0.5304(3) 0.40921(9) 1.08969(17) 0.0177(4) Uani 1 1 d . . . H6 H 0.6677 0.4386 1.1352 0.021 Uiso 1 1 calc R . . C2 C 0.2862(3) 0.35690(8) 0.87473(16) 0.0139(3) Uani 1 1 d . . . C10 C 0.3824(3) 0.37751(8) 0.63589(17) 0.0162(4) Uani 1 1 d . . . C5 C 0.3717(3) 0.37497(9) 1.17013(18) 0.0189(4) Uani 1 1 d . . . H5 H 0.3984 0.3814 1.2714 0.023 Uiso 1 1 calc R . . C7 C -0.2192(3) 0.23873(9) 0.96122(19) 0.0221(4) Uani 1 1 d . . . H7A H -0.1017 0.2073 1.0234 0.033 Uiso 1 1 calc R . . H7B H -0.3500 0.2124 0.8948 0.033 Uiso 1 1 calc R . . H7C H -0.3115 0.2683 1.0206 0.033 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 0.0169(6) 0.0209(7) 0.0124(6) 0.0001(4) 0.0045(4) -0.0046(5) O4 0.0215(7) 0.0311(7) 0.0140(6) 0.0013(5) 0.0065(5) -0.0047(5) O5 0.0188(7) 0.0258(7) 0.0197(6) 0.0017(5) 0.0027(5) -0.0072(5) O2 0.0187(6) 0.0231(7) 0.0199(6) 0.0019(5) 0.0064(5) -0.0072(5) C9 0.0132(8) 0.0143(9) 0.0147(8) 0.0019(6) 0.0044(6) 0.0011(6) O3 0.0258(7) 0.0396(8) 0.0134(6) -0.0025(5) 0.0055(5) -0.0127(6) C1 0.0141(8) 0.0150(9) 0.0147(8) 0.0011(6) 0.0043(6) 0.0028(6) C4 0.0174(9) 0.0210(9) 0.0177(8) 0.0047(6) 0.0086(6) 0.0024(7) C3 0.0136(8) 0.0169(9) 0.0168(8) 0.0017(6) 0.0043(6) 0.0007(6) C11 0.0138(8) 0.0156(9) 0.0156(8) 0.0015(6) 0.0041(6) 0.0006(6) C8 0.0137(8) 0.0131(9) 0.0177(8) 0.0012(6) 0.0040(6) 0.0007(6) C6 0.0193(9) 0.0180(9) 0.0156(8) -0.0005(6) 0.0025(6) 0.0010(6) C2 0.0151(8) 0.0158(9) 0.0116(7) 0.0012(6) 0.0041(6) 0.0022(6) C10 0.0151(8) 0.0196(9) 0.0148(8) 0.0017(6) 0.0050(6) -0.0001(6) C5 0.0227(9) 0.0217(10) 0.0128(8) 0.0007(6) 0.0043(7) 0.0039(7) C7 0.0185(9) 0.0207(9) 0.0286(9) 0.0071(7) 0.0084(7) -0.0037(7) _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 1.3670(18) . ? O1 C10 1.3891(19) . ? O4 C11 1.2664(19) . ? O5 C11 1.2741(19) . ? O2 C3 1.357(2) . ? O2 C7 1.4409(19) . ? C9 C8 1.351(2) . ? C9 C10 1.468(2) . ? C9 C11 1.489(2) . ? O3 C10 1.1980(19) . ? C1 C2 1.389(2) . ? C1 C6 1.408(2) . ? C1 C8 1.435(2) . ? C4 C3 1.388(2) . ? C4 C5 1.404(2) . ? C3 C2 1.409(2) . ? C6 C5 1.376(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 C2 O1 C10 122.83(13) . . ? C3 O2 C7 117.07(13) . . ? C8 C9 C10 120.51(14) . . ? C8 C9 C11 119.48(14) . . ? C10 C9 C11 120.00(14) . . ? C2 C1 C6 119.51(15) . . ? C2 C1 C8 116.92(14) . . ? C6 C1 C8 123.54(15) . . ? C3 C4 C5 120.80(15) . . ? O2 C3 C4 126.41(14) . . ? O2 C3 C2 115.65(14) . . ? C4 C3 C2 117.93(15) . . ? O4 C11 O5 123.43(14) . . ? O4 C11 C9 119.80(14) . . ? O5 C11 C9 116.77(14) . . ? C9 C8 C1 121.84(15) . . ? C5 C6 C1 119.37(16) . . ? O1 C2 C1 121.87(14) . . ? O1 C2 C3 116.58(14) . . ? C1 C2 C3 121.54(14) . . ? O3 C10 O1 115.93(14) . . ? O3 C10 C9 128.13(15) . . ? O1 C10 C9 115.94(13) . . ? C6 C5 C4 120.84(15) . . ? _diffrn_measured_fraction_theta_max 0.933 _diffrn_reflns_theta_full 28.33 _diffrn_measured_fraction_theta_full 0.933 _refine_diff_density_max 0.484 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.058 #===END