Supplementary Material (ESI) for J. Mater. Chem. This journal is (C)The Royal Society of Chemistry 2003 paper B210427J data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H10 O4' _chemical_formula_weight 230.21 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' 'N' 'N' 0.0061 0.0033 '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 Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x+1/2, -y, z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' 'x-1/2, y, -z-1/2' _cell_length_a 15.47(2) _cell_length_b 7.797(14) _cell_length_c 18.86(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2275(6) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description parallelopiped _exptl_crystal_colour white _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.35 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _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 'Marresearch Image Plate' _diffrn_measurement_method '95 frames at 2^o intervals, counting time 2 min.' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3948 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0722 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 25.87 _reflns_number_total 1613 _reflns_number_gt 941 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'XDS (Kabsch, 1991)' _computing_cell_refinement XDS _computing_data_reduction XDS _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'PLATON(Spek,1994)' _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 w=1/[\s^2^(Fo^2^)+(0.1274P)^2^+0.0564P] 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 SHELXL _refine_ls_extinction_coef 0.005(2) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1613 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1766 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.2600 _refine_ls_wR_factor_gt 0.2277 _refine_ls_goodness_of_fit_ref 1.102 _refine_ls_restrained_S_all 1.102 _refine_ls_shift/su_max 0.006 _refine_ls_shift/su_mean 0.001 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6582(5) 1.0652(6) 0.2049(3) 0.0420(17) Uani 1 d . . . H1 H 0.6014 1.0868 0.2183 0.050 Uiso 1 calc R . . C2 C 0.6760(5) 0.9804(6) 0.1412(3) 0.0398(18) Uani 1 d . . . C21 C 0.6052(5) 0.9126(6) 0.0954(3) 0.048(2) Uani 1 d . . . O22 O 0.6220(3) 0.8283(5) 0.0431(2) 0.0550(14) Uani 1 d . . . O23 O 0.5267(4) 0.9477(6) 0.1172(2) 0.0659(16) Uani 1 d . . . H23 H 0.4916 0.9104 0.0885 0.079 Uiso 1 calc R . . C3 C 0.7602(5) 0.9520(6) 0.1214(3) 0.0444(19) Uani 1 d . . . H3 H 0.7714 0.8982 0.0784 0.053 Uiso 1 calc R . . C4 C 0.8297(5) 1.0017(6) 0.1643(3) 0.0419(17) Uani 1 d . . . C5 C 0.8116(5) 1.0875(7) 0.2278(3) 0.0445(18) Uani 1 d . . . H5 H 0.8569 1.1247 0.2563 0.053 Uiso 1 calc R . . C6 C 0.7274(5) 1.1177(6) 0.2486(3) 0.0408(17) Uani 1 d . . . C51 C 0.9176(6) 0.9636(7) 0.1442(3) 0.0480(19) Uani 1 d . . . C52 C 0.9883(6) 0.9243(7) 0.1260(3) 0.0494(18) Uani 1 d . . . C53 C 1.0744(5) 0.8749(8) 0.1037(3) 0.0511(19) Uani 1 d . . . H53A H 1.1151 0.9020 0.1412 0.061 Uiso 1 calc R . . H53B H 1.0759 0.7519 0.0962 0.061 Uiso 1 calc R . . O54 O 1.1008(3) 0.9598(5) 0.0400(2) 0.0567(15) Uani 1 d . . . H54 H 1.1016 0.8906 0.0073 0.068 Uiso 1 calc R . . C61 C 0.7100(4) 1.2016(6) 0.3157(3) 0.0427(17) Uani 1 d . . . C62 C 0.6978(4) 1.2683(7) 0.3714(3) 0.0434(17) Uani 1 d . . . C63 C 0.6810(5) 1.3479(8) 0.4398(3) 0.056(2) Uani 1 d . . . H63A H 0.7235 1.3081 0.4739 0.067 Uiso 1 calc R . . H63B H 0.6871 1.4713 0.4354 0.067 Uiso 1 calc R . . O64 O 0.5956(3) 1.3082(5) 0.4653(2) 0.0543(14) Uani 1 d . . . H64 H 0.5893 1.2039 0.4667 0.065 Uiso 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 C1 0.046(5) 0.032(3) 0.048(4) 0.001(2) 0.008(3) 0.004(3) C2 0.053(6) 0.025(3) 0.042(3) -0.001(2) 0.015(3) -0.001(3) C21 0.080(7) 0.028(3) 0.036(3) 0.000(2) 0.002(4) -0.004(3) O22 0.072(4) 0.044(2) 0.049(2) -0.0056(18) 0.006(2) -0.003(2) O23 0.059(5) 0.071(3) 0.067(3) -0.023(2) 0.014(3) -0.004(3) C3 0.064(6) 0.036(3) 0.033(3) -0.002(2) 0.009(3) 0.000(3) C4 0.053(6) 0.037(3) 0.036(3) 0.002(2) 0.013(3) 0.007(3) C5 0.053(6) 0.038(3) 0.043(3) 0.003(2) 0.006(3) -0.003(3) C6 0.053(6) 0.032(3) 0.037(3) 0.002(2) 0.009(3) -0.002(3) C51 0.058(7) 0.046(3) 0.041(3) 0.000(2) 0.006(3) 0.003(3) C52 0.053(6) 0.043(3) 0.052(4) -0.009(3) 0.008(4) 0.003(3) C53 0.057(6) 0.042(3) 0.054(4) -0.002(3) -0.001(3) 0.006(3) O54 0.063(4) 0.051(2) 0.056(3) -0.0135(19) 0.016(2) -0.005(2) C61 0.049(5) 0.035(3) 0.044(4) 0.002(3) 0.007(3) 0.002(3) C62 0.052(5) 0.040(3) 0.038(3) -0.002(2) 0.008(3) -0.001(3) C63 0.072(7) 0.049(4) 0.047(4) -0.010(3) 0.008(4) -0.001(3) O64 0.060(4) 0.051(2) 0.052(2) -0.002(2) 0.014(2) 0.006(2) _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 C1 C2 1.399(7) . ? C1 C6 1.411(9) . ? C2 C3 1.373(10) . ? C2 C21 1.492(10) . ? C21 O22 1.214(7) . ? C21 O23 1.310(9) . ? C3 C4 1.399(10) . ? C4 C5 1.400(7) . ? C4 C51 1.442(11) . ? C5 C6 1.381(9) . ? C6 C61 1.450(8) . ? C51 C52 1.186(10) . ? C52 C53 1.449(11) . ? C53 O54 1.431(7) . ? C61 C62 1.187(7) . ? C62 C63 1.455(8) . ? C63 O64 1.440(9) . ? 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 C1 C6 119.2(6) . . ? C3 C2 C1 119.8(6) . . ? C3 C2 C21 118.8(5) . . ? C1 C2 C21 121.3(7) . . ? O22 C21 O23 124.5(7) . . ? O22 C21 C2 120.4(7) . . ? O23 C21 C2 115.2(5) . . ? C2 C3 C4 121.8(5) . . ? C3 C4 C5 118.2(7) . . ? C3 C4 C51 121.0(5) . . ? C5 C4 C51 120.8(6) . . ? C6 C5 C4 120.9(6) . . ? C5 C6 C1 120.0(5) . . ? C5 C6 C61 120.0(6) . . ? C1 C6 C61 120.0(6) . . ? C52 C51 C4 176.5(7) . . ? C51 C52 C53 179.5(7) . . ? O54 C53 C52 112.5(5) . . ? C62 C61 C6 178.2(7) . . ? C61 C62 C63 178.7(7) . . ? O64 C63 C62 111.6(6) . . ? _refine_diff_density_max 0.248 _refine_diff_density_min -0.267 _refine_diff_density_rms 0.064 _publ_section_references ; Kabsch, W. (1988), J.Appl.Cryst 21 916-932. Sheldrick, G.M. (1990) SHELX86, Acta Cryst. A46 467-480. Sheldrick, G.M. (1993) SHELXL program for crystallography refinement. University of Gottingen, Germany. Spek, A.L., (1994) PLATON-94 program, Utrecht University, The Netherlands ; #===END