data_jac04 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H16 N2 O6 S4' _chemical_formula_sum 'C18 H16 N2 O6 S4' _chemical_formula_weight 484.57 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' '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+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.6944(3) _cell_length_b 9.6777(3) _cell_length_c 26.3981(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1965.71(12) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9912 _cell_measurement_theta_min 2.61 _cell_measurement_theta_max 29.28 _exptl_crystal_description Plate _exptl_crystal_colour 'Light yellow' _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas . _exptl_crystal_density_diffrn 1.637 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 0.525 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7868 _exptl_absorpt_correction_T_max 0.9742 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker KAPPA APEX II' _diffrn_measurement_method '\w scans; 9 settings' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 42286 _diffrn_reflns_av_R_equivalents 0.0472 _diffrn_reflns_av_sigmaI/netI 0.0297 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.24 _diffrn_reflns_theta_max 29.30 _reflns_number_total 5365 _reflns_number_gt 4892 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2 v2009.7-0' _computing_cell_refinement 'Bruker SAINT-Plus v7.68A' _computing_data_reduction 'Bruker SAINT-Plus v7.68A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker XP v5.1' _computing_publication_material 'Bruker XCIF 2008' _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 matrix' _refine_ls_weighting_scheme Sigma _refine_ls_weighting_details 'w=1/s^2^(Fo^2^)' _atom_sites_solution_primary 'Direct methods' _atom_sites_solution_secondary 'Difference Fourier map' _atom_sites_solution_hydrogens 'Geometric positions' _refine_ls_hydrogen_treatment Riding _chemical_absolute_configuration ad _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 -0.02(6) _refine_ls_number_reflns 5365 _refine_ls_number_parameters 273 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.0642 _refine_ls_wR_factor_gt 0.0639 _refine_ls_goodness_of_fit_ref 2.797 _refine_ls_restrained_S_all 2.797 _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 S1 S 0.34501(8) 0.74086(7) 0.34196(3) 0.02119(15) Uani 1 1 d . . . S2 S 0.15368(9) 0.59925(7) 0.34771(3) 0.02260(16) Uani 1 1 d . . . S3 S 0.04290(9) 0.63979(7) 0.41760(3) 0.02318(16) Uani 1 1 d . . . S4 S -0.18166(9) 0.73542(7) 0.39873(3) 0.02270(16) Uani 1 1 d . . . O1 O 0.4095(2) 0.9173(2) 0.16046(7) 0.0305(5) Uani 1 1 d . . . O2 O -0.0845(2) 0.73026(19) 0.21859(7) 0.0239(4) Uani 1 1 d . . . H2 H -0.1456 0.7842 0.2361 0.036 Uiso 1 1 calc R . . O3 O 0.3157(2) 1.02330(19) 0.40855(6) 0.0226(4) Uani 1 1 d . . . O4 O -0.2156(2) 0.90296(19) 0.29048(6) 0.0198(4) Uani 1 1 d . . . O5 O 0.2022(2) 0.9505(2) 0.50615(7) 0.0379(6) Uani 1 1 d . . . H5 H 0.2549 0.9639 0.4787 0.057 Uiso 1 1 calc R . . O6 O -0.2979(2) 1.17162(19) 0.51963(7) 0.0277(5) Uani 1 1 d . . . N1 N 0.0760(3) 0.8971(2) 0.30113(7) 0.0122(4) Uani 1 1 d . . . N2 N 0.0315(2) 0.9677(2) 0.40249(7) 0.0129(4) Uani 1 1 d . . . C1 C 0.2554(3) 0.8757(3) 0.13902(10) 0.0249(7) Uani 1 1 d . . . H1 H 0.2466 0.8910 0.1036 0.030 Uiso 1 1 calc R . . C2 C 0.1178(3) 0.8178(3) 0.16004(10) 0.0217(6) Uani 1 1 d . . . H2A H 0.0267 0.7945 0.1373 0.026 Uiso 1 1 calc R . . C3 C 0.0847(3) 0.7836(3) 0.21440(9) 0.0186(6) Uani 1 1 d . . . H3 H 0.1691 0.7109 0.2253 0.022 Uiso 1 1 calc R . . C4 C 0.1153(3) 0.9144(3) 0.24642(9) 0.0135(5) Uani 1 1 d . . . H4 H 0.0451 0.9925 0.2324 0.016 Uiso 1 1 calc R . . C5 C 0.3062(3) 0.9543(3) 0.24706(10) 0.0167(6) Uani 1 1 d . . . C6 C 0.4231(4) 0.9471(3) 0.21127(10) 0.0235(7) Uani 1 1 d . . . H6 H 0.5383 0.9657 0.2223 0.028 Uiso 1 1 calc R . . C7 C 0.3548(3) 0.9946(3) 0.30034(9) 0.0169(6) Uani 1 1 d . . . H7A H 0.3378 1.0948 0.3060 0.020 Uiso 1 1 calc R . . H7B H 0.4772 0.9704 0.3078 0.020 Uiso 1 1 calc R . . C8 C 0.2289(3) 0.9089(3) 0.33257(9) 0.0144(6) Uani 1 1 d . . . C9 C 0.1969(3) 0.9709(3) 0.38454(9) 0.0152(6) Uani 1 1 d . . . C10 C -0.0888(3) 0.9024(2) 0.31885(9) 0.0136(5) Uani 1 1 d . . . C11 C -0.1150(3) 0.9105(3) 0.37528(9) 0.0138(5) Uani 1 1 d . . . C12 C -0.2663(3) 1.0049(3) 0.39004(9) 0.0146(6) Uani 1 1 d . . . H12A H -0.2790 1.0819 0.3656 0.018 Uiso 1 1 calc R . . H12B H -0.3768 0.9527 0.3915 0.018 Uiso 1 1 calc R . . C13 C -0.3277(3) 1.1166(3) 0.47253(10) 0.0207(6) Uani 1 1 d . . . H13 H -0.4441 1.1216 0.4607 0.025 Uiso 1 1 calc R . . C14 C -0.2160(3) 1.0581(3) 0.44179(9) 0.0147(6) Uani 1 1 d . . . C15 C -0.0220(3) 1.0389(3) 0.44998(9) 0.0144(6) Uani 1 1 d . . . H15 H 0.0358 1.1313 0.4519 0.017 Uiso 1 1 calc R . . C16 C 0.0198(3) 0.9562(3) 0.49759(10) 0.0199(6) Uani 1 1 d . . . H16 H -0.0269 0.8603 0.4940 0.024 Uiso 1 1 calc R . . C17 C -0.0555(3) 1.0219(3) 0.54424(10) 0.0215(6) Uani 1 1 d . . . H17 H -0.0028 0.9907 0.5747 0.026 Uiso 1 1 calc R . . C18 C -0.1787(4) 1.1133(3) 0.55174(9) 0.0239(6) Uani 1 1 d . . . H18 H -0.1869 1.1449 0.5857 0.029 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 S1 0.0186(3) 0.0209(4) 0.0241(4) 0.0012(3) -0.0016(3) 0.0049(3) S2 0.0258(4) 0.0206(4) 0.0214(4) 0.0007(3) -0.0002(3) 0.0003(3) S3 0.0254(4) 0.0226(4) 0.0216(4) 0.0020(3) 0.0003(3) 0.0041(3) S4 0.0192(3) 0.0189(4) 0.0300(4) 0.0044(3) 0.0003(3) -0.0019(3) O1 0.0225(10) 0.0517(14) 0.0174(11) -0.0012(10) 0.0067(9) -0.0018(10) O2 0.0245(10) 0.0230(11) 0.0243(11) -0.0085(9) 0.0072(8) -0.0102(9) O3 0.0089(9) 0.0382(12) 0.0205(11) -0.0071(9) -0.0004(8) -0.0028(9) O4 0.0094(9) 0.0311(11) 0.0188(10) -0.0050(9) -0.0031(8) -0.0003(9) O5 0.0197(11) 0.0697(17) 0.0243(12) 0.0143(12) -0.0046(9) 0.0085(12) O6 0.0303(11) 0.0320(12) 0.0208(11) -0.0099(9) -0.0006(9) 0.0068(10) N1 0.0120(11) 0.0120(11) 0.0126(11) 0.0009(9) -0.0011(9) 0.0005(9) N2 0.0129(11) 0.0156(11) 0.0102(11) 0.0006(9) -0.0009(9) -0.0006(9) C1 0.0319(17) 0.0277(17) 0.0150(15) -0.0033(12) 0.0020(12) 0.0036(14) C2 0.0267(16) 0.0211(15) 0.0174(15) -0.0059(11) -0.0005(12) 0.0005(12) C3 0.0187(14) 0.0161(14) 0.0210(15) -0.0041(11) 0.0019(11) -0.0009(12) C4 0.0137(13) 0.0136(13) 0.0133(13) 0.0013(10) 0.0004(10) 0.0000(11) C5 0.0164(14) 0.0157(13) 0.0181(14) 0.0020(11) 0.0009(12) -0.0022(12) C6 0.0185(15) 0.0331(17) 0.0189(16) 0.0012(12) -0.0009(12) -0.0021(13) C7 0.0091(13) 0.0232(14) 0.0183(14) 0.0003(11) 0.0001(11) 0.0010(12) C8 0.0085(12) 0.0170(13) 0.0177(14) -0.0001(11) -0.0011(10) 0.0041(11) C9 0.0113(13) 0.0179(14) 0.0165(14) 0.0030(11) -0.0005(11) 0.0034(11) C10 0.0138(13) 0.0101(12) 0.0170(14) 0.0002(11) -0.0011(11) -0.0013(11) C11 0.0080(12) 0.0172(13) 0.0162(14) 0.0026(11) 0.0001(10) -0.0031(11) C12 0.0105(12) 0.0179(13) 0.0154(14) 0.0002(11) 0.0010(10) -0.0002(11) C13 0.0185(14) 0.0244(15) 0.0193(14) -0.0012(12) -0.0006(12) 0.0036(13) C14 0.0130(13) 0.0172(14) 0.0140(14) 0.0037(11) -0.0005(11) -0.0004(11) C15 0.0166(14) 0.0146(13) 0.0120(13) -0.0007(10) 0.0003(11) -0.0009(11) C16 0.0160(14) 0.0269(16) 0.0168(14) 0.0014(12) -0.0003(12) 0.0020(12) C17 0.0199(14) 0.0298(16) 0.0149(14) 0.0025(12) -0.0013(12) -0.0064(13) C18 0.0321(16) 0.0273(16) 0.0123(13) -0.0038(12) 0.0029(13) -0.0081(15) _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 S1 C8 1.872(3) . ? S1 S2 2.0170(9) . ? S2 S3 2.0698(10) . ? S3 S4 2.0224(10) . ? S4 C11 1.875(3) . ? O1 C6 1.376(3) . ? O1 C1 1.374(3) . ? O2 C3 1.405(3) . ? O3 C9 1.223(3) . ? O4 C10 1.230(3) . ? O5 C16 1.423(3) . ? O6 C13 1.372(3) . ? O6 C18 1.370(3) . ? N1 C10 1.352(3) . ? N1 C8 1.444(3) . ? N1 C4 1.485(3) . ? N2 C9 1.358(3) . ? N2 C11 1.447(3) . ? N2 C15 1.488(3) . ? C1 C2 1.320(4) . ? C2 C3 1.495(3) . ? C3 C4 1.540(3) . ? C4 C5 1.519(3) . ? C5 C6 1.306(3) . ? C5 C7 1.507(3) . ? C7 C8 1.533(3) . ? C8 C9 1.517(3) . ? C10 C11 1.505(3) . ? C11 C12 1.531(3) . ? C12 C14 1.510(3) . ? C13 C14 1.310(3) . ? C14 C15 1.520(3) . ? C15 C16 1.524(3) . ? C16 C17 1.502(3) . ? C17 C18 1.312(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 C8 S1 S2 104.59(8) . . ? S1 S2 S3 103.82(4) . . ? S4 S3 S2 102.66(4) . . ? C11 S4 S3 105.14(8) . . ? C6 O1 C1 121.9(2) . . ? C13 O6 C18 120.8(2) . . ? C10 N1 C8 124.18(19) . . ? C10 N1 C4 121.56(19) . . ? C8 N1 C4 112.57(18) . . ? C9 N2 C11 124.4(2) . . ? C9 N2 C15 122.8(2) . . ? C11 N2 C15 112.32(18) . . ? C2 C1 O1 130.0(3) . . ? C1 C2 C3 129.4(3) . . ? O2 C3 C2 108.4(2) . . ? O2 C3 C4 113.6(2) . . ? C2 C3 C4 108.6(2) . . ? N1 C4 C5 102.42(19) . . ? N1 C4 C3 114.2(2) . . ? C5 C4 C3 111.3(2) . . ? C6 C5 C7 121.2(2) . . ? C6 C5 C4 130.1(2) . . ? C7 C5 C4 108.4(2) . . ? C5 C6 O1 131.6(3) . . ? C5 C7 C8 102.77(19) . . ? N1 C8 C9 114.8(2) . . ? N1 C8 C7 103.82(19) . . ? C9 C8 C7 113.0(2) . . ? N1 C8 S1 113.32(17) . . ? C9 C8 S1 107.53(17) . . ? C7 C8 S1 103.97(16) . . ? O3 C9 N2 122.0(2) . . ? O3 C9 C8 120.7(2) . . ? N2 C9 C8 117.3(2) . . ? O4 C10 N1 122.2(2) . . ? O4 C10 C11 119.7(2) . . ? N1 C10 C11 118.0(2) . . ? N2 C11 C10 114.00(19) . . ? N2 C11 C12 103.76(18) . . ? C10 C11 C12 112.7(2) . . ? N2 C11 S4 113.25(16) . . ? C10 C11 S4 108.43(17) . . ? C12 C11 S4 104.34(16) . . ? C14 C12 C11 103.83(19) . . ? C14 C13 O6 128.3(2) . . ? C13 C14 C12 122.6(2) . . ? C13 C14 C15 127.5(2) . . ? C12 C14 C15 109.8(2) . . ? N2 C15 C14 102.0(2) . . ? N2 C15 C16 113.2(2) . . ? C14 C15 C16 112.9(2) . . ? O5 C16 C17 105.5(2) . . ? O5 C16 C15 111.1(2) . . ? C17 C16 C15 111.9(2) . . ? C18 C17 C16 133.5(3) . . ? C17 C18 O6 131.9(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 29.30 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.078 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.084