# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 207/348 data_CWR9711 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 H5 N O2 S4 Cl2' _chemical_formula_weight 346.27 _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' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'S' 'S' 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 '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 7.814(2) _cell_length_b 8.2112(6) _cell_length_c 10.115(2) _cell_angle_alpha 86.496(12) _cell_angle_beta 88.77(2) _cell_angle_gamma 85.463(12) _cell_volume 645.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 10.87 _cell_measurement_theta_max 31.84 _exptl_crystal_description rhombs _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.781 _exptl_crystal_density_method ? _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 10.490 _exptl_absorpt_correction_type Semi-empirical _exptl_absorpt_correction_T_min 0.0308 _exptl_absorpt_correction_T_max 0.1280 _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Siemens P4' _diffrn_measurement_method '\w scans' _diffrn_standards_number 3 _diffrn_standards_interval_count 97 _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2261 _diffrn_reflns_av_R_equivalents 0.0163 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 4.38 _diffrn_reflns_theta_max 63.00 _reflns_number_total 2088 _reflns_number_observed 1784 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'Siemens XSCANS' _computing_cell_refinement 'Siemens XSCANS' _computing_data_reduction 'Siemens SHELXTL' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics 'Siemens SHELXTL' _computing_publication_material 'Siemens SHELXTL' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 1 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^)+(0.0766P)^2^+0.1853P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0042(10) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 2087 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0543 _refine_ls_R_factor_obs 0.0469 _refine_ls_wR_factor_all 0.1410 _refine_ls_wR_factor_obs 0.1279 _refine_ls_goodness_of_fit_all 1.088 _refine_ls_goodness_of_fit_obs 1.125 _refine_ls_restrained_S_all 1.141 _refine_ls_restrained_S_obs 1.125 _refine_ls_shift/esd_max 0.001 _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 S1 S 0.2229(2) 0.52021(14) 0.89908(10) 0.0677(3) Uani 1 d . . S2 S 0.2609(2) 0.33566(13) 1.04376(11) 0.0645(3) Uani 1 d . . C3 C 0.2823(5) 0.4646(5) 1.1781(4) 0.0521(8) Uani 1 d . . O3 O 0.3121(4) 0.4060(4) 1.2885(3) 0.0644(7) Uani 1 d . . C3A C 0.2556(5) 0.6379(5) 1.1378(4) 0.0511(8) Uani 1 d . . N4 N 0.2657(4) 0.7550(4) 1.2328(3) 0.0543(8) Uani 1 d . . C4A C 0.1476(5) 0.7464(5) 1.3393(4) 0.0506(8) Uani 1 d . . C5 C -0.0348(5) 0.7724(5) 1.3056(4) 0.0537(9) Uani 1 d . . O5 O -0.0958(4) 0.7977(4) 1.1973(3) 0.0663(8) Uani 1 d . . S6 S -0.17389(14) 0.7560(2) 1.44760(11) 0.0713(4) Uani 1 d . . S7 S 0.01497(15) 0.7231(2) 1.58581(11) 0.0741(4) Uani 1 d . . C7A C 0.1801(5) 0.7209(5) 1.4695(4) 0.0536(9) Uani 1 d . . Cl7 Cl 0.37669(13) 0.6798(2) 1.53952(11) 0.0693(3) Uani 1 d . . C8A C 0.2281(5) 0.6750(5) 1.0080(4) 0.0565(9) Uani 1 d . . Cl8 Cl 0.1913(2) 0.86722(14) 0.93666(12) 0.0790(4) Uani 1 d . . C9 C 0.4298(6) 0.8308(6) 1.2374(5) 0.0729(12) Uani 1 d . . H9A H 0.4794(6) 0.8397(6) 1.1488(5) 0.088 Uiso 1 calc R . H9B H 0.5089(6) 0.7609(6) 1.2924(5) 0.088 Uiso 1 calc R . C10 C 0.4084(10) 0.9961(7) 1.2909(7) 0.097(2) Uani 1 d . . H10A H 0.5180(10) 1.0411(7) 1.2922(7) 0.145 Uiso 1 calc R . H10B H 0.3614(10) 0.9875(7) 1.3793(7) 0.145 Uiso 1 calc R . H10C H 0.3319(10) 1.0663(7) 1.2357(7) 0.145 Uiso 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 0.0837(8) 0.0685(7) 0.0497(5) -0.0045(4) -0.0047(5) 0.0029(5) S2 0.0753(7) 0.0576(6) 0.0599(6) -0.0067(4) -0.0041(5) 0.0031(5) C3 0.043(2) 0.062(2) 0.051(2) -0.003(2) 0.0019(15) -0.002(2) O3 0.069(2) 0.067(2) 0.054(2) 0.0059(13) -0.0048(13) 0.0016(14) C3A 0.042(2) 0.059(2) 0.053(2) -0.002(2) 0.0014(15) -0.006(2) N4 0.049(2) 0.061(2) 0.054(2) -0.0046(14) 0.0024(14) -0.0131(14) C4A 0.051(2) 0.047(2) 0.054(2) -0.0042(15) -0.004(2) -0.0033(15) C5 0.051(2) 0.053(2) 0.057(2) -0.004(2) -0.005(2) -0.002(2) O5 0.064(2) 0.080(2) 0.054(2) -0.0024(14) -0.0140(14) 0.0002(15) S6 0.0457(5) 0.1064(9) 0.0602(6) -0.0044(6) 0.0001(4) 0.0033(5) S7 0.0537(6) 0.1157(10) 0.0512(6) -0.0021(6) -0.0003(4) 0.0014(6) C7A 0.047(2) 0.061(2) 0.053(2) -0.002(2) -0.006(2) -0.002(2) Cl7 0.0510(6) 0.0894(8) 0.0670(6) 0.0015(5) -0.0128(4) -0.0036(5) C8A 0.056(2) 0.060(2) 0.053(2) 0.000(2) 0.001(2) -0.005(2) Cl8 0.1064(10) 0.0613(6) 0.0670(7) 0.0108(5) 0.0007(6) -0.0048(6) C9 0.064(3) 0.079(3) 0.078(3) -0.015(2) 0.011(2) -0.019(2) C10 0.118(5) 0.072(3) 0.105(4) -0.015(3) 0.026(4) -0.034(3) _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 C8A 1.735(4) . ? S1 S2 2.050(2) . ? S2 C3 1.792(4) . ? C3 O3 1.208(5) . ? C3 C3A 1.456(6) . ? C3A C8A 1.347(6) . ? C3A N4 1.408(5) . ? N4 C4A 1.405(5) . ? N4 C9 1.472(5) . ? C4A C7A 1.347(6) . ? C4A C5 1.468(5) . ? C5 O5 1.204(5) . ? C5 S6 1.787(4) . ? S6 S7 2.046(2) . ? S7 C7A 1.727(4) . ? C7A Cl7 1.706(4) . ? C8A Cl8 1.701(4) . ? C9 C10 1.488(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 C8A S1 S2 94.13(15) . . ? C3 S2 S1 96.58(14) . . ? O3 C3 C3A 126.8(4) . . ? O3 C3 S2 120.6(3) . . ? C3A C3 S2 112.6(3) . . ? C8A C3A N4 124.2(4) . . ? C8A C3A C3 116.3(4) . . ? N4 C3A C3 119.4(3) . . ? C4A N4 C3A 116.0(3) . . ? C4A N4 C9 124.1(3) . . ? C3A N4 C9 116.1(3) . . ? C7A C4A N4 128.3(4) . . ? C7A C4A C5 115.4(4) . . ? N4 C4A C5 116.3(3) . . ? O5 C5 C4A 127.8(4) . . ? O5 C5 S6 119.4(3) . . ? C4A C5 S6 112.7(3) . . ? C5 S6 S7 96.67(14) . . ? C7A S7 S6 94.12(14) . . ? C4A C7A Cl7 126.7(3) . . ? C4A C7A S7 120.9(3) . . ? Cl7 C7A S7 112.4(2) . . ? C3A C8A Cl8 125.4(3) . . ? C3A C8A S1 120.2(3) . . ? Cl8 C8A S1 114.4(2) . . ? N4 C9 C10 112.1(4) . . ? _refine_diff_density_max 0.525 _refine_diff_density_min -0.297 _refine_diff_density_rms 0.074