# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_str681 _database_code_CSD 163544 _journal_coden_Cambridge 207 _publ_requested_journal 'Perkin Transactions 1' loop_ _publ_author_name 'Dang, Hai-Shan' 'Roberts, B. P.' _publ_contact_author_name 'Dr B P Roberts' _publ_contact_author_address ; Dr B P Roberts Department of Chemistry University College London 20 Gordon Street LONDON WC1H OAJ UK ; _publ_contact_author_email 'B.P.ROBERTS@UCL.AC.UK' _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H22 O6' _chemical_formula_weight 274.31 _chemical_melting_point ? _chemical_compound_source ? 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 orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.3710(10) _cell_length_b 10.704(2) _cell_length_c 25.652(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1474.8(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 28 _cell_measurement_theta_min 8.5 _cell_measurement_theta_max 13 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.235 _exptl_crystal_density_method ? _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type ? _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 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device Nicolet R3mV _diffrn_measurement_method 2theta _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ~1.0 _diffrn_reflns_number 1537 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 3.05 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1537 _reflns_number_observed 1154 _reflns_observed_criterion >2sigma(I) _computing_data_collection P3 _computing_cell_refinement P3 _computing_data_reduction XDISK _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics XP _computing_publication_material CIFTAB _refine_special_details ; Refinement on F^2^ for ALL reflections except for 3 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses 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 observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs 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^)+(0.0871P)^2^+0.1577P] 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 fixed positions and U(iso) _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0635(75) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 4.17(246) _refine_ls_number_reflns 1534 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0691 _refine_ls_R_factor_obs 0.0483 _refine_ls_wR_factor_all 0.1468 _refine_ls_wR_factor_obs 0.1230 _refine_ls_goodness_of_fit_all 1.045 _refine_ls_goodness_of_fit_obs 1.052 _refine_ls_restrained_S_all 1.068 _refine_ls_restrained_S_obs 1.052 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.8957(7) 1.0494(2) 0.51833(9) 0.0713(9) Uani 1 d . . O2 O 0.7675(6) 1.0800(2) 0.43193(8) 0.0581(7) Uani 1 d . . O3 O 0.6581(5) 0.8045(2) 0.43962(9) 0.0580(7) Uani 1 d . . O4 O 0.9316(5) 0.8360(2) 0.37449(8) 0.0539(7) Uani 1 d . . O5 O 0.9890(6) 1.2195(2) 0.34820(9) 0.0686(9) Uani 1 d . . O6 O 1.2549(7) 1.1548(3) 0.28549(11) 0.0831(10) Uani 1 d . . C1 C 0.8116(13) 1.1660(4) 0.5397(2) 0.101(2) Uani 1 d . . H1A H 0.9238(13) 1.1908(4) 0.5670(2) 0.080 Uiso 1 d R . H1B H 0.6477(13) 1.1550(4) 0.5539(2) 0.080 Uiso 1 d R . H1C H 0.8074(13) 1.2294(4) 0.5133(2) 0.080 Uiso 1 d R . C2 C 0.7463(9) 1.0058(3) 0.47771(12) 0.0547(9) Uani 1 d . . H2A H 0.5757(9) 0.9991(3) 0.48851(12) 0.080 Uiso 1 d R . C3 C 0.8486(7) 0.8785(3) 0.46245(13) 0.0517(9) Uani 1 d . . H3A H 0.9289(7) 0.8372(3) 0.49109(13) 0.080 Uiso 1 d R . C4 C 0.7647(7) 0.7442(3) 0.39481(12) 0.0501(8) Uani 1 d . . C5 C 0.9056(9) 0.6271(4) 0.4109(2) 0.0714(12) Uani 1 d . . H5A H 1.0305(9) 0.6490(4) 0.4360(2) 0.080 Uiso 1 d R . H5B H 0.9838(9) 0.5905(4) 0.3809(2) 0.080 Uiso 1 d R . H5C H 0.7919(9) 0.5682(4) 0.4260(2) 0.080 Uiso 1 d R . C6 C 0.5655(8) 0.7197(4) 0.3556(2) 0.0717(12) Uani 1 d . . H6A H 0.4838(8) 0.7967(4) 0.3470(2) 0.080 Uiso 1 d R . H6B H 0.4464(8) 0.6622(4) 0.3698(2) 0.080 Uiso 1 d R . H6C H 0.6383(8) 0.6845(4) 0.3248(2) 0.080 Uiso 1 d R . C7 C 1.0293(7) 0.9060(3) 0.41730(12) 0.0483(8) Uani 1 d . . H7A H 1.1972(7) 0.8821(3) 0.42539(12) 0.080 Uiso 1 d R . C8 C 1.0016(7) 1.0483(3) 0.40854(13) 0.0499(9) Uani 1 d . . H8A H 1.1335(7) 1.0910(3) 0.42643(13) 0.080 Uiso 1 d R . C9 C 1.0029(8) 1.0869(3) 0.35193(12) 0.0524(9) Uani 1 d . . H9A H 0.8663(8) 1.0483(3) 0.33392(12) 0.080 Uiso 1 d R . C10 C 1.2405(9) 1.0602(3) 0.32366(14) 0.0635(10) Uani 1 d . . H10A H 1.2405(9) 0.9783(3) 0.30840(14) 0.080 Uiso 1 d R . H10B H 1.3781(9) 1.0670(3) 0.34740(14) 0.080 Uiso 1 d R . C11 C 1.0900(10) 1.2514(4) 0.2992(2) 0.0754(14) Uani 1 d . . C12 C 0.8897(13) 1.2506(8) 0.2573(2) 0.134(3) Uani 1 d . . H12A H 0.8086(13) 1.1707(8) 0.2575(2) 0.080 Uiso 1 d R . H12B H 0.9622(13) 1.2651(8) 0.2236(2) 0.080 Uiso 1 d R . H12C H 0.7700(13) 1.3148(8) 0.2647(2) 0.080 Uiso 1 d R . C13 C 1.2188(21) 1.3709(5) 0.3020(3) 0.159(4) Uani 1 d . . H13A H 1.3414(21) 1.3623(5) 0.3289(3) 0.080 Uiso 1 d R . H13B H 1.1078(21) 1.4381(5) 0.3105(3) 0.080 Uiso 1 d R . H13C H 1.3001(21) 1.3884(5) 0.2694(3) 0.080 Uiso 1 d 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 0.101(2) 0.062(2) 0.0504(13) -0.0106(12) 0.000(2) 0.015(2) O2 0.072(2) 0.0552(14) 0.0473(12) 0.0073(10) 0.0104(14) 0.020(2) O3 0.056(2) 0.0613(15) 0.0563(13) -0.0024(12) 0.0136(13) 0.0001(14) O4 0.061(2) 0.0522(13) 0.0486(12) -0.0064(11) 0.0098(12) -0.0063(13) O5 0.092(2) 0.0563(15) 0.0570(14) 0.0104(12) 0.019(2) 0.016(2) O6 0.090(2) 0.080(2) 0.079(2) 0.0214(15) 0.033(2) 0.013(2) C1 0.153(6) 0.078(3) 0.071(2) -0.023(2) 0.019(4) 0.012(4) C2 0.067(2) 0.056(2) 0.041(2) 0.0036(14) 0.005(2) 0.010(2) C3 0.061(2) 0.050(2) 0.043(2) 0.003(2) 0.000(2) 0.006(2) C4 0.050(2) 0.050(2) 0.051(2) -0.001(2) 0.007(2) 0.002(2) C5 0.074(3) 0.059(2) 0.081(3) 0.003(2) 0.009(3) 0.009(2) C6 0.057(3) 0.082(3) 0.076(3) -0.014(2) -0.004(2) 0.002(2) C7 0.045(2) 0.050(2) 0.050(2) -0.0015(14) 0.000(2) 0.006(2) C8 0.053(2) 0.050(2) 0.047(2) -0.0034(15) 0.002(2) 0.002(2) C9 0.058(2) 0.051(2) 0.049(2) 0.0017(15) 0.001(2) 0.001(2) C10 0.072(3) 0.058(2) 0.061(2) 0.002(2) 0.009(2) 0.002(2) C11 0.096(4) 0.062(2) 0.068(2) 0.017(2) 0.028(3) 0.021(3) C12 0.121(5) 0.201(7) 0.080(3) 0.060(4) 0.024(4) 0.042(6) C13 0.274(11) 0.073(3) 0.131(5) 0.001(3) 0.094(7) -0.023(6) _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 1.395(5) . ? O1 C1 1.436(5) . ? O2 C2 1.422(4) . ? O2 C8 1.434(5) . ? O3 C3 1.420(4) . ? O3 C4 1.437(4) . ? O4 C4 1.429(4) . ? O4 C7 1.430(4) . ? O5 C11 1.411(5) . ? O5 C9 1.424(4) . ? O6 C11 1.406(5) . ? O6 C10 1.411(4) . ? C2 C3 1.521(5) . ? C3 C7 1.539(5) . ? C4 C6 1.491(5) . ? C4 C5 1.520(5) . ? C7 C8 1.546(4) . ? C8 C9 1.510(5) . ? C9 C10 1.496(6) . ? C11 C13 1.455(8) . ? C11 C12 1.521(7) . ? 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 113.3(4) . . ? C2 O2 C8 106.5(3) . . ? C3 O3 C4 107.1(3) . . ? C4 O4 C7 108.1(2) . . ? C11 O5 C9 106.3(3) . . ? C11 O6 C10 108.6(3) . . ? O1 C2 O2 112.6(3) . . ? O1 C2 C3 106.5(3) . . ? O2 C2 C3 105.0(3) . . ? O3 C3 C2 110.2(3) . . ? O3 C3 C7 104.5(2) . . ? C2 C3 C7 104.5(3) . . ? O4 C4 O3 103.5(2) . . ? O4 C4 C6 109.0(3) . . ? O3 C4 C6 109.4(3) . . ? O4 C4 C5 110.7(3) . . ? O3 C4 C5 110.6(3) . . ? C6 C4 C5 113.3(3) . . ? O4 C7 C3 104.3(3) . . ? O4 C7 C8 111.7(3) . . ? C3 C7 C8 103.7(3) . . ? O2 C8 C9 110.0(3) . . ? O2 C8 C7 104.9(3) . . ? C9 C8 C7 114.1(3) . . ? O5 C9 C10 101.7(3) . . ? O5 C9 C8 109.7(3) . . ? C10 C9 C8 114.7(3) . . ? O6 C10 C9 104.3(3) . . ? O6 C11 O5 106.7(3) . . ? O6 C11 C13 111.0(5) . . ? O5 C11 C13 110.6(4) . . ? O6 C11 C12 105.3(4) . . ? O5 C11 C12 110.9(4) . . ? C13 C11 C12 112.0(5) . . ? _refine_diff_density_max 0.209 _refine_diff_density_min -0.196 _refine_diff_density_rms 0.054