# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/472 data_1 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C12 H16 O7 ' _chemical_formula_weight 272.24 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 triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.405(9) _cell_length_b 9.044(9) _cell_length_c 10.192(12) _cell_angle_alpha 69.549(10) _cell_angle_beta 76.797(10) _cell_angle_gamma 71.600(10) _cell_volume 682.7(13) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used all _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.324 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 288 _exptl_absorpt_coefficient_mu 0.110 _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_detector_area_resol_mean ? _diffrn_standards_number all _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1863 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0257 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.76 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1863 _reflns_number_gt 1595 _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^)+(0.5242P)^2^+2.9340P] 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 0.82(9) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1863 _refine_ls_number_parameters 177 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0645 _refine_ls_wR_factor_ref 0.2011 _refine_ls_wR_factor_gt 0.1822 _refine_ls_goodness_of_fit_ref 0.291 _refine_ls_restrained_S_all 0.291 _refine_ls_shift/su_max 0.028 _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 -0.1501(3) 0.2766(3) 0.2493(2) 0.0353(6) Uani 1 d . . . C2 C -0.3095(3) 0.3338(3) 0.1729(3) 0.0443(7) Uani 1 d . . . C3 C -0.2810(4) 0.3012(4) 0.0322(3) 0.0616(8) Uani 1 d . . . H3A H -0.3563 0.3895 -0.0291 0.074 Uiso 1 calc R . . H3B H -0.3125 0.2015 0.0476 0.074 Uiso 1 calc R . . C4 C -0.0986(4) 0.2843(4) -0.0454(3) 0.0577(8) Uani 1 d . . . H4A H -0.0745 0.2078 -0.0989 0.069 Uiso 1 calc R . . H4B H -0.0886 0.3894 -0.1115 0.069 Uiso 1 calc R . . C5 C 0.0298(3) 0.2249(3) 0.0577(3) 0.0464(7) Uani 1 d . . . O6 O -0.0170(2) 0.33253(19) 0.14575(16) 0.0427(5) Uani 1 d . . . O7 O 0.0146(2) 0.0661(2) 0.15753(17) 0.0469(6) Uani 1 d . . . C8 C -0.0708(2) 0.0889(3) 0.2911(2) 0.0352(6) Uani 1 d . . . H8 H 0.0126 0.0594 0.3553 0.042 Uiso 1 calc R . . O11 O -0.1489(3) 0.4739(2) 0.3592(2) 0.0660(7) Uani 1 d . . . C81 C -0.1952(3) -0.0174(3) 0.3563(2) 0.0395(6) Uani 1 d . . . C84 C -0.2701(4) -0.2283(4) 0.5562(4) 0.0670(9) Uani 1 d . . . H84A H -0.2250 -0.3049 0.6400 0.080 Uiso 1 calc R . . H84B H -0.2787 -0.2863 0.4963 0.080 Uiso 1 calc R . . H84C H -0.3803 -0.1637 0.5819 0.080 Uiso 1 calc R . . O20 O -0.4453(2) 0.4039(3) 0.2235(2) 0.0648(7) Uani 1 d . . . C11 C -0.1844(3) 0.3520(3) 0.3694(2) 0.0408(6) Uani 1 d . . . O12 O -0.2595(2) 0.2598(2) 0.48532(17) 0.0460(6) Uani 1 d . . . C14 C -0.3064(4) 0.3185(4) 0.6100(3) 0.0553(8) Uani 1 d . . . H14A H -0.3760 0.4302 0.5863 0.066 Uiso 1 calc R . . H14B H -0.2057 0.3157 0.6430 0.066 Uiso 1 calc R . . C15 C -0.4025(4) 0.2089(4) 0.7219(3) 0.0632(8) Uani 1 d . . . H15A H -0.5046 0.2168 0.6898 0.076 Uiso 1 calc R . . H15B H -0.4304 0.2414 0.8063 0.076 Uiso 1 calc R . . H15C H -0.3343 0.0982 0.7416 0.076 Uiso 1 calc R . . C51 C 0.2110(4) 0.2151(4) -0.0108(3) 0.0686(9) Uani 1 d . . . H51A H 0.2467 0.1346 -0.0601 0.082 Uiso 1 calc R . . H51B H 0.2824 0.1850 0.0606 0.082 Uiso 1 calc R . . H51C H 0.2189 0.3196 -0.0764 0.082 Uiso 1 calc R . . O82 O -0.3121(3) -0.0067(3) 0.3008(3) 0.0765(8) Uani 1 d . . . O83 O -0.1580(2) -0.1213(2) 0.48072(19) 0.0506(6) Uani 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 C1 0.0428(11) 0.0318(11) 0.0292(10) -0.0102(9) -0.0013(8) -0.0083(8) C2 0.0535(13) 0.0341(12) 0.0407(13) -0.0089(10) -0.0109(10) -0.0042(9) C3 0.0772(18) 0.0606(17) 0.0482(15) -0.0196(14) -0.0268(13) -0.0027(14) C4 0.092(2) 0.0445(14) 0.0328(12) -0.0125(11) -0.0093(12) -0.0110(13) C5 0.0641(15) 0.0320(11) 0.0361(12) -0.0122(10) 0.0066(10) -0.0102(10) O6 0.0559(10) 0.0359(9) 0.0373(9) -0.0133(8) 0.0052(7) -0.0184(7) O7 0.0611(10) 0.0338(9) 0.0381(9) -0.0144(7) 0.0062(7) -0.0067(7) C8 0.0408(10) 0.0318(11) 0.0302(11) -0.0089(9) -0.0022(8) -0.0079(8) O11 0.1088(17) 0.0494(12) 0.0506(11) -0.0239(10) 0.0071(11) -0.0376(11) C81 0.0449(11) 0.0344(11) 0.0389(12) -0.0099(10) -0.0071(9) -0.0101(9) C84 0.0752(17) 0.0582(18) 0.0637(18) 0.0047(15) -0.0069(15) -0.0394(14) O20 0.0507(11) 0.0686(14) 0.0643(13) -0.0246(12) -0.0102(9) 0.0058(9) C11 0.0516(12) 0.0361(12) 0.0361(12) -0.0153(10) -0.0021(9) -0.0106(9) O12 0.0623(10) 0.0444(10) 0.0346(9) -0.0190(8) 0.0050(7) -0.0185(8) C14 0.0692(15) 0.0649(17) 0.0395(13) -0.0296(13) 0.0029(11) -0.0190(13) C15 0.0687(16) 0.079(2) 0.0425(14) -0.0242(14) 0.0071(12) -0.0234(14) C51 0.0732(18) 0.0581(17) 0.0577(17) -0.0159(15) 0.0239(15) -0.0187(14) O82 0.0820(14) 0.0781(16) 0.0760(14) 0.0080(13) -0.0379(12) -0.0450(12) O83 0.0574(10) 0.0467(11) 0.0456(10) 0.0022(9) -0.0116(8) -0.0255(8) _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 O6 1.438(3) . ? C1 C11 1.531(3) . ? C1 C8 1.555(3) . ? C1 C2 1.557(3) . ? C2 O20 1.215(3) . ? C2 C3 1.515(4) . ? C3 C4 1.543(5) . ? C4 C5 1.522(4) . ? C5 O6 1.455(3) . ? C5 O7 1.466(3) . ? C5 C51 1.512(4) . ? O7 C8 1.438(3) . ? C8 C81 1.526(3) . ? O11 C11 1.196(3) . ? C81 O82 1.204(4) . ? C81 O83 1.323(3) . ? C84 O83 1.463(3) . ? C11 O12 1.339(3) . ? O12 C14 1.470(3) . ? C14 C15 1.494(4) . ? 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 O6 C1 C11 109.30(18) . . ? O6 C1 C8 100.46(15) . . ? C11 C1 C8 114.74(18) . . ? O6 C1 C2 106.88(19) . . ? C11 C1 C2 110.59(17) . . ? C8 C1 C2 114.02(17) . . ? O20 C2 C3 123.5(2) . . ? O20 C2 C1 120.7(2) . . ? C3 C2 C1 115.8(2) . . ? C2 C3 C4 115.4(2) . . ? C5 C4 C3 111.5(2) . . ? O6 C5 O7 104.03(18) . . ? O6 C5 C51 109.2(2) . . ? O7 C5 C51 110.4(2) . . ? O6 C5 C4 108.7(2) . . ? O7 C5 C4 109.3(2) . . ? C51 C5 C4 114.7(2) . . ? C1 O6 C5 103.56(17) . . ? C8 O7 C5 108.88(16) . . ? O7 C8 C81 110.39(17) . . ? O7 C8 C1 101.89(16) . . ? C81 C8 C1 115.95(18) . . ? O82 C81 O83 124.9(2) . . ? O82 C81 C8 123.8(2) . . ? O83 C81 C8 111.4(2) . . ? O11 C11 O12 126.3(2) . . ? O11 C11 C1 124.6(2) . . ? O12 C11 C1 109.09(19) . . ? C11 O12 C14 116.04(19) . . ? O12 C14 C15 107.6(2) . . ? C81 O83 C84 116.9(2) . . ? _refine_diff_density_max 0.214 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.068 _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 ;