# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2008 data_global _journal_name_full 'New J.Chem.' _journal_coden_cambridge 0440 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Mark Nieuwenhuyzen' _publ_contact_author_email woody.m@qub.ac.uk loop_ _publ_author_name P.C.Marr 'A.J. Blake' 'Steven J. Craythorne' 'Andrew C. Marr' 'M. Nieuwenhuyzen' 'Ciara L. Pollock' data_dmixetom _database_code_depnum_ccdc_archive 'CCDC 646818' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H14 O8 S2' _chemical_formula_weight 302.31 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' S S 0.1246 0.1234 '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 5.4647(8) _cell_length_b 11.1834(17) _cell_length_c 20.479(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1251.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4557 _cell_measurement_theta_min 2.70 _cell_measurement_theta_max 27.03 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas not_measured _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.455 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 10002 _diffrn_reflns_av_R_equivalents 0.0320 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2209 _reflns_number_gt 1986 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^)+(0.0376P)^2^+0.2091P] 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 calc _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.14(8) _refine_ls_number_reflns 2209 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0719 _refine_ls_wR_factor_gt 0.0693 _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_restrained_S_all 1.042 _refine_ls_shift/su_max 0.001 _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 C1 C -1.0027(5) -1.1223(3) -0.48273(15) 0.0590(8) Uani 1 1 d . . . H1A H -1.1184 -1.1377 -0.5170 0.088 Uiso 1 1 calc R . . H1B H -1.0871 -1.0917 -0.4452 0.088 Uiso 1 1 calc R . . H1C H -0.9204 -1.1953 -0.4714 0.088 Uiso 1 1 calc R . . O2 O -0.6628(5) -1.0633(3) -0.56383(10) 0.1032(9) Uani 1 1 d . . . S3 S -0.78895(14) -1.01757(6) -0.50935(3) 0.0503(2) Uani 1 1 d . . . O3 O -0.9060(5) -0.90484(17) -0.51306(11) 0.0818(8) Uani 1 1 d . . . O5 O -0.5892(3) -1.01447(15) -0.45381(8) 0.0428(4) Uani 1 1 d . . . C6 C -0.6424(4) -0.95163(18) -0.39297(10) 0.0327(5) Uani 1 1 d . . . H6A H -0.8117 -0.9637 -0.3786 0.039 Uiso 1 1 calc R . . C7 C -0.4598(4) -0.9962(2) -0.34361(11) 0.0368(5) Uani 1 1 d . . . H7A H -0.5201 -0.9838 -0.2996 0.044 Uiso 1 1 calc R . . H7B H -0.4286 -1.0808 -0.3498 0.044 Uiso 1 1 calc R . . O8 O -0.2422(3) -0.92828(14) -0.35448(8) 0.0385(4) Uani 1 1 d . . . C9 C -0.3134(4) -0.81028(19) -0.37365(11) 0.0347(5) Uani 1 1 d . . . H9A H -0.2041 -0.7798 -0.4077 0.042 Uiso 1 1 calc R . . C10 C -0.5782(4) -0.8197(2) -0.39953(11) 0.0339(5) Uani 1 1 d . . . H10A H -0.5922 -0.7917 -0.4447 0.041 Uiso 1 1 calc R . . O11 O -0.7278(3) -0.75181(13) -0.35597(8) 0.0397(4) Uani 1 1 d . . . C12 C -0.5748(4) -0.6589(2) -0.33015(12) 0.0406(6) Uani 1 1 d . . . H12A H -0.6431 -0.6266 -0.2902 0.049 Uiso 1 1 calc R . . H12B H -0.5554 -0.5946 -0.3615 0.049 Uiso 1 1 calc R . . C13 C -0.3326(4) -0.7205(2) -0.31717(10) 0.0361(5) Uani 1 1 d . . . H13A H -0.1952 -0.6642 -0.3163 0.043 Uiso 1 1 calc R . . O14 O -0.3619(3) -0.78419(14) -0.25543(7) 0.0412(4) Uani 1 1 d . . . S15 S -0.17211(12) -0.77085(6) -0.19788(3) 0.04070(17) Uani 1 1 d . . . C16 C 0.0507(5) -0.8785(2) -0.21454(12) 0.0467(7) Uani 1 1 d . . . H16A H 0.1278 -0.8606 -0.2555 0.070 Uiso 1 1 calc R . . H16B H -0.0245 -0.9560 -0.2168 0.070 Uiso 1 1 calc R . . H16C H 0.1713 -0.8780 -0.1805 0.070 Uiso 1 1 calc R . . O17 O -0.0623(4) -0.65531(15) -0.20137(10) 0.0636(6) Uani 1 1 d . . . O18 O -0.3073(4) -0.8022(2) -0.14167(9) 0.0714(6) Uani 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 C1 0.0555(17) 0.0561(17) 0.0653(19) -0.0070(15) -0.0123(16) -0.0063(14) O2 0.0988(19) 0.168(2) 0.0429(12) -0.0403(14) 0.0173(13) -0.036(2) S3 0.0611(4) 0.0570(4) 0.0328(3) -0.0029(3) -0.0058(3) -0.0076(3) O3 0.116(2) 0.0502(12) 0.0793(15) 0.0170(11) -0.0553(15) -0.0053(13) O5 0.0389(9) 0.0515(10) 0.0379(9) -0.0095(8) 0.0002(8) 0.0009(8) C6 0.0317(12) 0.0374(12) 0.0290(11) -0.0013(9) 0.0015(10) 0.0014(10) C7 0.0363(13) 0.0331(12) 0.0410(13) 0.0049(10) 0.0005(11) -0.0006(10) O8 0.0289(9) 0.0379(9) 0.0488(9) 0.0046(7) -0.0025(8) 0.0023(7) C9 0.0334(12) 0.0347(12) 0.0360(12) 0.0068(9) 0.0015(11) -0.0026(10) C10 0.0343(12) 0.0351(12) 0.0324(12) 0.0024(10) 0.0005(10) 0.0013(10) O11 0.0325(9) 0.0388(9) 0.0477(9) -0.0038(7) -0.0016(8) 0.0045(7) C12 0.0446(14) 0.0353(13) 0.0417(14) -0.0010(11) 0.0001(12) 0.0008(11) C13 0.0352(12) 0.0358(12) 0.0372(12) 0.0054(10) -0.0011(11) -0.0064(10) O14 0.0369(9) 0.0496(9) 0.0370(9) 0.0050(8) -0.0050(8) -0.0083(8) S15 0.0409(3) 0.0479(3) 0.0333(3) -0.0074(3) -0.0025(3) 0.0052(3) C16 0.0459(15) 0.0493(15) 0.0450(15) 0.0005(12) 0.0003(13) 0.0113(13) O17 0.0718(14) 0.0439(11) 0.0750(13) -0.0174(10) -0.0263(12) -0.0013(10) O18 0.0598(12) 0.1190(17) 0.0354(10) 0.0022(10) 0.0101(11) 0.0139(13) _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 S3 1.742(3) . ? O2 S3 1.408(2) . ? S3 O3 1.416(2) . ? S3 O5 1.5770(18) . ? O5 C6 1.460(3) . ? C6 C7 1.505(3) . ? C6 C10 1.522(3) . ? C7 O8 1.429(3) . ? O8 C9 1.431(3) . ? C9 C13 1.536(3) . ? C9 C10 1.544(3) . ? C10 O11 1.429(3) . ? O11 C12 1.434(3) . ? C12 C13 1.515(3) . ? C13 O14 1.460(3) . ? O14 S15 1.5769(17) . ? S15 O18 1.4120(19) . ? S15 O17 1.4264(19) . ? S15 C16 1.746(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 O2 S3 O3 120.16(17) . . ? O2 S3 O5 103.92(14) . . ? O3 S3 O5 109.38(10) . . ? O2 S3 C1 109.39(16) . . ? O3 S3 C1 108.22(16) . . ? O5 S3 C1 104.67(12) . . ? C6 O5 S3 119.22(14) . . ? O5 C6 C7 106.34(18) . . ? O5 C6 C10 110.20(17) . . ? C7 C6 C10 103.14(19) . . ? O8 C7 C6 105.73(17) . . ? C7 O8 C9 107.86(16) . . ? O8 C9 C13 114.54(18) . . ? O8 C9 C10 106.61(18) . . ? C13 C9 C10 103.84(19) . . ? O11 C10 C6 109.16(18) . . ? O11 C10 C9 106.59(18) . . ? C6 C10 C9 104.60(19) . . ? C10 O11 C12 106.36(17) . . ? O11 C12 C13 104.18(17) . . ? O14 C13 C12 106.14(19) . . ? O14 C13 C9 109.90(18) . . ? C12 C13 C9 102.98(19) . . ? C13 O14 S15 121.94(14) . . ? O18 S15 O17 119.07(14) . . ? O18 S15 O14 104.00(11) . . ? O17 S15 O14 108.96(11) . . ? O18 S15 C16 110.66(13) . . ? O17 S15 C16 108.74(14) . . ? O14 S15 C16 104.32(11) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S3 O5 C6 169.01(19) . . . . ? O3 S3 O5 C6 39.5(2) . . . . ? C1 S3 O5 C6 -76.25(19) . . . . ? S3 O5 C6 C7 162.47(15) . . . . ? S3 O5 C6 C10 -86.4(2) . . . . ? O5 C6 C7 O8 82.6(2) . . . . ? C10 C6 C7 O8 -33.4(2) . . . . ? C6 C7 O8 C9 34.7(2) . . . . ? C7 O8 C9 C13 93.1(2) . . . . ? C7 O8 C9 C10 -21.2(2) . . . . ? O5 C6 C10 O11 152.96(17) . . . . ? C7 C6 C10 O11 -93.8(2) . . . . ? O5 C6 C10 C9 -93.3(2) . . . . ? C7 C6 C10 C9 19.9(2) . . . . ? O8 C9 C10 O11 115.35(19) . . . . ? C13 C9 C10 O11 -6.0(2) . . . . ? O8 C9 C10 C6 -0.2(2) . . . . ? C13 C9 C10 C6 -121.53(18) . . . . ? C6 C10 O11 C12 141.69(19) . . . . ? C9 C10 O11 C12 29.2(2) . . . . ? C10 O11 C12 C13 -41.1(2) . . . . ? O11 C12 C13 O14 -79.7(2) . . . . ? O11 C12 C13 C9 35.8(2) . . . . ? O8 C9 C13 O14 -20.8(3) . . . . ? C10 C9 C13 O14 95.0(2) . . . . ? O8 C9 C13 C12 -133.60(19) . . . . ? C10 C9 C13 C12 -17.8(2) . . . . ? C12 C13 O14 S15 -129.23(17) . . . . ? C9 C13 O14 S15 120.07(18) . . . . ? C13 O14 S15 O18 156.74(18) . . . . ? C13 O14 S15 O17 28.8(2) . . . . ? C13 O14 S15 C16 -87.22(19) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.194 _refine_diff_density_min -0.166 _refine_diff_density_rms 0.037