# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2003 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 loop_ _publ_author_name 'Mark Wood' 'Daniel J. Cane-Honeysett' 'Michael D. Dowle' _publ_contact_author_name 'Dr Mark Wood' _publ_contact_author_address ; School of Chemistry University of Exeter Stocker Road Exeter Devon EX4 4QD UNITED KINGDOM ; _publ_contact_author_email M.E.WOOD@EXETER.AC.UK _publ_section_title ; Synthetic and structural studies on 1,2,4-dithiazolidine-3,5-dione derivatives ; data_1 _database_code_CSD 210313 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Wood _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 K4 N4 O8 S8' _chemical_formula_weight 693.08 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' K K 0.2009 0.2494 '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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.3952(4) _cell_length_b 22.4561(11) _cell_length_c 13.7894(9) _cell_angle_alpha 90.00 _cell_angle_beta 106.786(4) _cell_angle_gamma 90.00 _cell_volume 2192.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 30990 _cell_measurement_theta_min 1.0 _cell_measurement_theta_max 27.48 _exptl_crystal_description prism _exptl_crystal_colour white _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.100 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1376 _exptl_absorpt_coefficient_mu 1.621 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.5492 _exptl_absorpt_correction_T_max 0.8292 _exptl_absorpt_process_details 'SORTAV (Blessing, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Bruker-Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker-Nonius KappaCCD' _diffrn_measurement_method 'phi & omega scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_decay_% negligible _diffrn_reflns_number 3840 _diffrn_reflns_av_R_equivalents 0.0616 _diffrn_reflns_av_sigmaI/netI 0.0709 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.38 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3840 _reflns_number_gt 2675 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO & COLLECT' _computing_data_reduction 'DENZO & COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.1000P)^2^+0.0000P] 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 none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3837 _refine_ls_number_parameters 289 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0952 _refine_ls_R_factor_gt 0.0593 _refine_ls_wR_factor_ref 0.1847 _refine_ls_wR_factor_gt 0.1596 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.021 _refine_ls_shift/su_mean 0.004 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 K1 K -0.05645(16) -0.16234(6) -0.10716(10) 0.0229(3) Uani 1 1 d . . . K2 K -0.43294(16) 0.08417(6) 0.10364(10) 0.0246(4) Uani 1 1 d . . . K3 K -0.08120(17) 0.18172(6) 0.39023(10) 0.0248(4) Uani 1 1 d . . . K4 K 0.43282(16) 0.07185(6) 0.38963(10) 0.0233(4) Uani 1 1 d . . . S1 S -0.0207(2) -0.09209(6) 0.11226(12) 0.0229(4) Uani 1 1 d . . . S2 S 0.24221(19) -0.05541(6) 0.16785(12) 0.0244(4) Uani 1 1 d . . . S3 S 0.4405(2) 0.34202(6) 0.36443(12) 0.0248(4) Uani 1 1 d . . . S4 S -0.0339(2) -0.09081(6) 0.38283(12) 0.0247(4) Uani 1 1 d . . . S5 S -0.26860(19) -0.03924(6) 0.32557(12) 0.0238(4) Uani 1 1 d . . . S6 S 0.4591(2) 0.16176(6) 0.59681(12) 0.0229(4) Uani 1 1 d . . . S7 S 0.21274(19) 0.28805(6) 0.30506(13) 0.0230(4) Uani 1 1 d . . . S8 S 0.7243(2) 0.19520(6) 0.65876(12) 0.0247(4) Uani 1 1 d . . . O1 O -0.3101(5) -0.02239(17) 0.0496(3) 0.0266(10) Uani 1 1 d . . . O2 O 0.2739(5) 0.05981(17) 0.1807(3) 0.0237(10) Uani 1 1 d . . . O3 O 0.7695(5) 0.29333(18) 0.4432(3) 0.0307(11) Uani 1 1 d . . . O4 O 0.2551(5) 0.17409(16) 0.3137(3) 0.0244(10) Uani 1 1 d . . . O5 O 0.2945(5) -0.03897(18) 0.4430(3) 0.0329(11) Uani 1 1 d . . . O6 O 0.7666(5) 0.07511(16) 0.3176(3) 0.0258(10) Uani 1 1 d . . . O7 O 0.1767(5) 0.23495(18) 0.5402(3) 0.0267(10) Uani 1 1 d . . . O8 O -0.2322(5) 0.19007(17) 0.1825(3) 0.0248(10) Uani 1 1 d . . . N1 N -0.0324(6) 0.0281(2) 0.1165(3) 0.0184(11) Uani 1 1 d . . . N2 N 0.5340(6) 0.2256(2) 0.3794(4) 0.0213(11) Uani 1 1 d . . . N3 N 0.0492(6) 0.0262(2) 0.3812(4) 0.0220(11) Uani 1 1 d . . . N4 N 0.4604(6) 0.28145(19) 0.6110(4) 0.0203(11) Uani 1 1 d . . . C1 C -0.1381(8) -0.0211(2) 0.0892(4) 0.0221(14) Uani 1 1 d . . . C2 C 0.1528(7) 0.0198(2) 0.1529(4) 0.0197(13) Uani 1 1 d . . . C3 C 0.6056(7) 0.2802(3) 0.4020(4) 0.0191(13) Uani 1 1 d . . . C4 C 0.3467(8) 0.2205(2) 0.3355(4) 0.0191(13) Uani 1 1 d . . . C5 C 0.1247(7) -0.0278(3) 0.4064(5) 0.0233(14) Uani 1 1 d . . . C6 C 0.8626(7) 0.0292(2) 0.3420(4) 0.0177(13) Uani 1 1 d . . . C7 C 0.3478(7) 0.2340(2) 0.5800(4) 0.0177(13) Uani 1 1 d . . . C8 C -0.3561(8) 0.2286(2) 0.1510(4) 0.0201(13) 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 K1 0.0181(7) 0.0223(7) 0.0267(9) -0.0010(6) 0.0041(6) 0.0017(5) K2 0.0185(7) 0.0237(7) 0.0304(9) -0.0014(6) 0.0050(6) -0.0005(5) K3 0.0194(7) 0.0250(7) 0.0280(9) -0.0028(6) 0.0034(6) -0.0033(5) K4 0.0187(7) 0.0239(7) 0.0249(9) 0.0006(5) 0.0026(6) 0.0031(5) S1 0.0219(8) 0.0161(7) 0.0302(10) -0.0001(6) 0.0064(7) -0.0011(6) S2 0.0181(8) 0.0198(8) 0.0335(11) 0.0024(7) 0.0044(7) 0.0031(6) S3 0.0278(9) 0.0161(7) 0.0302(10) -0.0003(6) 0.0079(8) -0.0031(6) S4 0.0264(8) 0.0166(7) 0.0305(11) 0.0018(6) 0.0073(8) 0.0032(6) S5 0.0178(8) 0.0160(8) 0.0356(11) -0.0025(6) 0.0046(7) -0.0024(6) S6 0.0231(8) 0.0152(7) 0.0296(10) -0.0001(6) 0.0063(7) -0.0021(6) S7 0.0186(8) 0.0171(7) 0.0326(10) 0.0026(6) 0.0063(7) 0.0041(6) S8 0.0171(8) 0.0200(8) 0.0344(11) 0.0012(7) 0.0033(7) 0.0028(6) O1 0.017(2) 0.026(2) 0.034(3) -0.0001(19) 0.0015(19) -0.0008(17) O2 0.019(2) 0.025(2) 0.028(3) -0.0021(18) 0.0085(19) -0.0033(17) O3 0.021(2) 0.040(3) 0.025(3) 0.003(2) -0.003(2) -0.0098(19) O4 0.023(2) 0.014(2) 0.032(3) 0.0001(18) 0.0013(19) -0.0036(16) O5 0.022(2) 0.037(3) 0.034(3) 0.003(2) 0.000(2) 0.0053(19) O6 0.028(2) 0.015(2) 0.032(3) 0.0022(18) 0.005(2) 0.0043(17) O7 0.016(2) 0.033(2) 0.028(3) -0.0020(19) 0.0001(19) -0.0009(17) O8 0.023(2) 0.025(2) 0.025(3) 0.0044(18) 0.0044(19) 0.0114(17) N1 0.013(2) 0.017(2) 0.026(3) -0.001(2) 0.007(2) 0.0014(19) N2 0.019(3) 0.021(3) 0.023(3) 0.002(2) 0.006(2) 0.002(2) N3 0.012(2) 0.024(3) 0.029(3) 0.000(2) 0.005(2) -0.003(2) N4 0.018(2) 0.018(2) 0.023(3) -0.003(2) 0.003(2) -0.0013(19) C1 0.024(3) 0.017(3) 0.023(4) 0.000(3) 0.004(3) 0.005(2) C2 0.017(3) 0.016(3) 0.027(4) 0.001(2) 0.008(3) -0.001(2) C3 0.013(3) 0.028(3) 0.017(4) 0.002(3) 0.006(3) 0.000(2) C4 0.021(3) 0.015(3) 0.021(4) 0.003(2) 0.005(3) 0.007(2) C5 0.016(3) 0.024(3) 0.028(4) 0.000(3) 0.004(3) -0.005(2) C6 0.015(3) 0.017(3) 0.022(4) -0.005(2) 0.006(3) -0.004(2) C7 0.014(3) 0.016(3) 0.023(4) -0.001(2) 0.006(3) 0.002(2) C8 0.024(3) 0.021(3) 0.016(4) -0.001(2) 0.008(3) -0.002(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 S1 C1 1.799(5) . ? S1 S2 2.046(2) . ? S2 C2 1.803(5) . ? S3 C3 1.823(5) . ? S3 S7 2.044(2) . ? S4 C5 1.807(5) . ? S4 S5 2.0462(19) . ? S5 C6 1.796(5) 1_455 ? S6 C7 1.803(5) . ? S6 S8 2.042(2) . ? S7 C4 1.794(5) . ? S8 C8 1.805(6) 4_666 ? O1 C1 1.232(6) . ? O2 C2 1.249(6) . ? O3 C3 1.217(6) . ? O4 C4 1.232(6) . ? O5 C5 1.237(6) . ? O6 C6 1.242(6) . ? O7 C7 1.226(6) . ? O8 C8 1.243(6) . ? N1 C2 1.329(7) . ? N1 C1 1.344(7) . ? N2 C3 1.335(7) . ? N2 C4 1.347(7) . ? N3 C6 1.331(6) 1_455 ? N3 C5 1.337(7) . ? N4 C8 1.328(7) 4_666 ? N4 C7 1.344(7) . ? C6 N3 1.331(6) 1_655 ? C6 S5 1.796(5) 1_655 ? C8 N4 1.328(7) 4_465 ? C8 S8 1.805(6) 4_465 ? 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 C1 S1 S2 93.87(19) . . ? C2 S2 S1 93.26(18) . . ? C3 S3 S7 93.95(19) . . ? C5 S4 S5 93.44(19) . . ? C6 S5 S4 93.91(19) 1_455 . ? C7 S6 S8 94.04(18) . . ? C4 S7 S3 94.15(19) . . ? C8 S8 S6 93.68(19) 4_666 . ? C2 N1 C1 116.2(5) . . ? C3 N2 C4 118.1(5) . . ? C6 N3 C5 117.2(5) 1_455 . ? C8 N4 C7 117.6(5) 4_666 . ? O1 C1 N1 125.9(5) . . ? O1 C1 S1 116.2(4) . . ? N1 C1 S1 117.9(4) . . ? O2 C2 N1 125.7(5) . . ? O2 C2 S2 115.6(4) . . ? N1 C2 S2 118.7(4) . . ? O3 C3 N2 127.3(5) . . ? O3 C3 S3 116.3(4) . . ? N2 C3 S3 116.4(4) . . ? O4 C4 N2 127.2(5) . . ? O4 C4 S7 115.5(4) . . ? N2 C4 S7 117.3(4) . . ? O5 C5 N3 126.1(5) . . ? O5 C5 S4 116.3(4) . . ? N3 C5 S4 117.6(4) . . ? O6 C6 N3 126.6(5) . 1_655 ? O6 C6 S5 115.5(4) . 1_655 ? N3 C6 S5 117.8(4) 1_655 1_655 ? O7 C7 N4 126.4(5) . . ? O7 C7 S6 116.6(4) . . ? N4 C7 S6 117.0(4) . . ? O8 C8 N4 126.1(5) . 4_465 ? O8 C8 S8 116.2(4) . 4_465 ? N4 C8 S8 117.7(4) 4_465 4_465 ? _diffrn_measured_fraction_theta_max 0.766 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.766 _refine_diff_density_max 0.606 _refine_diff_density_min -0.633 _refine_diff_density_rms 0.141