# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 207/456 data_s92 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C21 H16 Cl2 O2 S2' _chemical_formula_weight 435.36 _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' 'S' 'S' 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 '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 6.977(10) _cell_length_b 40.172(17) _cell_length_c 7.607(14) _cell_angle_alpha 90.00 _cell_angle_beta 115.05(9) _cell_angle_gamma 90.00 _cell_volume 1931.5(46) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method ? _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.567 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius FAST TV Area detector' _diffrn_measurement_method 'Omega scans' _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5941 _diffrn_reflns_av_R_equivalents 0.1736 _diffrn_reflns_av_sigmaI/netI 0.6018 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 46 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 25.03 _reflns_number_total 2729 _reflns_number_observed 556 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-92 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 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^)+(0.0000P)^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 riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2729 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2233 _refine_ls_R_factor_obs 0.0562 _refine_ls_wR_factor_all 0.1313 _refine_ls_wR_factor_obs 0.0879 _refine_ls_goodness_of_fit_all 0.472 _refine_ls_goodness_of_fit_obs 0.875 _refine_ls_restrained_S_all 0.472 _refine_ls_restrained_S_obs 0.875 _refine_ls_shift/esd_max 0.004 _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 Cl1 Cl 0.3097(4) 0.53371(7) 0.2893(4) 0.0426(8) Uani 1 d . . Cl2 Cl -0.3270(5) 0.19146(8) -0.0718(4) 0.0643(11) Uani 1 d . . S1 S -0.4078(4) 0.43079(8) 0.1612(4) 0.0395(8) Uani 1 d . . S2 S -0.6665(5) 0.33483(8) -0.3368(4) 0.0408(9) Uani 1 d . . O1 O 0.2662(10) 0.4064(2) 0.4521(9) 0.040(2) Uani 1 d . . O2 O -0.0415(10) 0.3113(2) 0.1354(9) 0.046(2) Uani 1 d . . C1 C 0.1140(15) 0.5050(2) 0.2688(13) 0.026(3) Uani 1 d . . C2 C 0.1692(15) 0.4720(2) 0.3127(11) 0.022(3) Uani 1 d . . H2 H 0.3108(15) 0.4658(2) 0.3608(11) 0.026 Uiso 1 calc R . C3 C 0.0176(15) 0.4482(3) 0.2863(13) 0.025(3) Uani 1 d . . C4 C -0.1930(17) 0.4580(3) 0.2206(12) 0.032(3) Uani 1 d . . C5 C -0.2401(15) 0.4921(3) 0.1969(13) 0.037(3) Uani 1 d . . H5 H -0.3778(15) 0.4990(3) 0.1664(13) 0.044 Uiso 1 calc R . C6 C -0.0876(16) 0.5159(2) 0.2175(13) 0.027(3) Uani 1 d . . H6 H -0.1217(16) 0.5384(2) 0.1971(13) 0.033 Uiso 1 calc R . C7 C 0.0806(16) 0.4141(3) 0.3376(13) 0.027(3) Uani 1 d . . C8 C -0.0718(15) 0.3855(2) 0.2496(12) 0.024(3) Uani 1 d . . H8 H -0.0066(15) 0.3651(2) 0.3205(12) 0.028 Uiso 1 calc R . C9 C -0.2731(15) 0.3925(3) 0.2785(13) 0.034(3) Uani 1 d . . H9 H -0.3711(15) 0.3741(3) 0.2174(13) 0.041 Uiso 1 calc R . C10 C -0.2277(15) 0.3925(2) 0.4967(11) 0.040(3) Uani 1 d . . H10A H -0.3583(18) 0.3949(16) 0.5092(11) 0.060 Uiso 1 calc R . H10B H -0.1351(79) 0.4106(9) 0.5612(21) 0.060 Uiso 1 calc R . H10C H -0.1617(89) 0.3718(7) 0.5547(23) 0.060 Uiso 1 calc R . C11 C -0.1169(16) 0.3806(3) 0.0332(12) 0.033(3) Uani 1 d . . H11 H -0.1805(16) 0.4012(3) -0.0355(12) 0.039 Uiso 1 calc R . C12 C 0.0942(15) 0.3751(3) 0.0133(12) 0.043(3) Uani 1 d . . H12A H 0.1751(45) 0.3580(10) 0.1016(63) 0.065 Uiso 1 calc R . H12B H 0.1740(44) 0.3955(4) 0.0434(82) 0.065 Uiso 1 calc R . H12C H 0.0636(15) 0.3685(15) -0.1172(26) 0.065 Uiso 1 calc R . C13 C -0.2704(16) 0.3530(3) -0.0610(14) 0.031(3) Uani 1 d . . C14 C -0.2116(17) 0.3190(3) 0.0026(14) 0.028(3) Uani 1 d . . C15 C -0.3586(17) 0.2909(3) -0.1019(14) 0.031(3) Uani 1 d . . C16 C -0.5622(16) 0.2960(3) -0.2515(15) 0.034(3) Uani 1 d . . C17 C -0.4657(15) 0.3606(3) -0.2061(13) 0.032(3) Uani 1 d . . H17 H -0.4902(15) 0.3831(3) -0.2362(13) 0.038 Uiso 1 calc R . C18 C -0.2901(17) 0.2592(3) -0.0458(13) 0.037(3) Uani 1 d . . H18 H -0.1570(17) 0.2558(3) 0.0547(13) 0.044 Uiso 1 calc R . C19 C -0.4162(18) 0.2318(3) -0.1366(17) 0.050(4) Uani 1 d . . C20 C -0.6197(18) 0.2372(3) -0.2835(15) 0.047(4) Uani 1 d . . H20 H -0.7063(18) 0.2191(3) -0.3439(15) 0.056 Uiso 1 calc R . C21 C -0.6904(18) 0.2688(3) -0.3376(15) 0.039(3) Uani 1 d . . H21 H -0.8264(18) 0.2723(3) -0.4335(15) 0.047 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 Cl1 0.039(2) 0.041(2) 0.048(2) -0.005(2) 0.018(2) -0.004(2) Cl2 0.088(3) 0.038(2) 0.095(3) -0.001(2) 0.066(2) 0.000(2) S1 0.025(2) 0.050(2) 0.045(2) 0.004(2) 0.016(2) 0.003(2) S2 0.025(2) 0.050(2) 0.042(2) -0.007(2) 0.008(2) -0.002(2) O1 0.017(4) 0.050(5) 0.044(5) 0.001(4) 0.005(4) 0.010(4) O2 0.025(5) 0.063(6) 0.033(4) 0.011(4) -0.005(4) 0.019(4) C1 0.026(7) 0.019(7) 0.024(6) 0.002(5) 0.001(6) -0.002(6) C2 0.012(6) 0.020(7) 0.017(5) 0.003(5) -0.010(5) -0.003(5) C3 0.018(7) 0.034(7) 0.019(6) 0.000(5) 0.004(6) 0.009(6) C4 0.047(8) 0.034(8) 0.014(6) -0.013(5) 0.012(6) -0.012(7) C5 0.022(7) 0.048(8) 0.039(7) 0.007(6) 0.012(6) 0.006(7) C6 0.038(7) 0.009(6) 0.028(6) 0.006(5) 0.007(6) 0.010(6) C7 0.026(7) 0.027(7) 0.022(6) -0.000(5) 0.005(6) -0.002(6) C8 0.016(6) 0.031(7) 0.016(5) 0.010(5) -0.002(5) 0.005(6) C9 0.023(7) 0.040(8) 0.040(7) 0.001(6) 0.014(6) -0.006(6) C10 0.037(8) 0.048(8) 0.032(7) 0.011(6) 0.012(6) 0.006(7) C11 0.036(8) 0.036(8) 0.021(6) 0.010(5) 0.008(6) 0.006(6) C12 0.036(8) 0.050(9) 0.039(7) -0.001(6) 0.011(6) -0.014(7) C13 0.024(7) 0.038(8) 0.035(7) -0.002(6) 0.018(6) 0.001(6) C14 0.034(7) 0.026(7) 0.026(6) 0.003(5) 0.017(6) -0.007(6) C15 0.031(7) 0.040(8) 0.028(6) -0.002(6) 0.018(6) 0.001(6) C16 0.012(6) 0.040(8) 0.049(7) -0.013(6) 0.012(6) -0.016(6) C17 0.025(7) 0.033(7) 0.037(6) 0.002(6) 0.014(6) -0.013(6) C18 0.043(9) 0.037(8) 0.027(6) 0.011(6) 0.012(6) 0.018(7) C19 0.038(9) 0.057(10) 0.069(9) 0.000(8) 0.036(8) -0.007(8) C20 0.046(9) 0.063(10) 0.059(9) -0.033(7) 0.048(8) -0.030(8) C21 0.043(8) 0.036(8) 0.053(7) 0.012(7) 0.034(7) 0.021(7) _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 Cl1 C1 1.743(10) . ? Cl2 C19 1.732(13) . ? S1 C4 1.753(11) . ? S1 C9 1.825(10) . ? S2 C17 1.687(9) . ? S2 C16 1.727(11) . ? O1 C7 1.255(10) . ? O2 C14 1.229(10) . ? C1 C6 1.363(12) . ? C1 C2 1.381(12) . ? C2 C3 1.378(12) . ? C3 C4 1.394(13) . ? C3 C7 1.440(13) . ? C4 C5 1.403(14) . ? C5 C6 1.390(13) . ? C7 C8 1.514(12) . ? C8 C9 1.536(12) . ? C8 C11 1.552(11) . ? C9 C10 1.553(11) . ? C11 C13 1.498(13) . ? C11 C12 1.559(12) . ? C13 C17 1.377(12) . ? C13 C14 1.447(13) . ? C14 C15 1.504(13) . ? C15 C18 1.366(13) . ? C15 C16 1.409(12) . ? C16 C21 1.388(13) . ? C18 C19 1.395(14) . ? C19 C20 1.402(13) . ? C20 C21 1.364(14) . ? 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 C4 S1 C9 101.0(5) . . ? C17 S2 C16 102.7(5) . . ? C6 C1 C2 121.8(10) . . ? C6 C1 Cl1 119.1(8) . . ? C2 C1 Cl1 119.0(8) . . ? C3 C2 C1 120.9(10) . . ? C2 C3 C4 118.9(10) . . ? C2 C3 C7 119.6(9) . . ? C4 C3 C7 121.4(10) . . ? C3 C4 C5 118.5(10) . . ? C3 C4 S1 125.0(9) . . ? C5 C4 S1 116.6(9) . . ? C6 C5 C4 122.1(10) . . ? C1 C6 C5 117.3(9) . . ? O1 C7 C3 121.9(10) . . ? O1 C7 C8 116.5(9) . . ? C3 C7 C8 121.6(9) . . ? C7 C8 C9 108.2(8) . . ? C7 C8 C11 110.7(8) . . ? C9 C8 C11 112.8(8) . . ? C8 C9 C10 111.6(8) . . ? C8 C9 S1 113.4(7) . . ? C10 C9 S1 110.7(7) . . ? C13 C11 C8 112.6(9) . . ? C13 C11 C12 111.3(8) . . ? C8 C11 C12 110.2(8) . . ? C17 C13 C14 121.5(10) . . ? C17 C13 C11 118.9(10) . . ? C14 C13 C11 119.7(9) . . ? O2 C14 C13 123.4(10) . . ? O2 C14 C15 116.8(9) . . ? C13 C14 C15 119.8(9) . . ? C18 C15 C16 119.2(10) . . ? C18 C15 C14 117.7(10) . . ? C16 C15 C14 123.2(10) . . ? C21 C16 C15 119.7(10) . . ? C21 C16 S2 116.6(8) . . ? C15 C16 S2 123.7(8) . . ? C13 C17 S2 129.0(9) . . ? C15 C18 C19 121.2(10) . . ? C18 C19 C20 119.2(11) . . ? C18 C19 Cl2 121.4(9) . . ? C20 C19 Cl2 119.4(10) . . ? C21 C20 C19 119.8(11) . . ? C20 C21 C16 120.9(11) . . ? _refine_diff_density_max 0.260 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.061