# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/247 data_hh267 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C8 Cl6 O2 S2' _chemical_formula_weight 404.90 _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' '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 monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 7.341(4) _cell_length_b 13.560(7) _cell_length_c 7.471(4) _cell_angle_alpha 90.00 _cell_angle_beta 118.440(10) _cell_angle_gamma 90.00 _cell_volume 653.9(6) _cell_formula_units_Z 2 _cell_measurement_temperature 119(1) _cell_measurement_reflns_used 24 _cell_measurement_theta_min 20 _cell_measurement_theta_max 30 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.056 _exptl_crystal_density_method ? _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 14.897 _exptl_absorpt_correction_type 'empirical XABS2' _exptl_absorpt_correction_T_min 0.032 _exptl_absorpt_correction_T_max 0.068 _exptl_special_details ; ? ; _diffrn_ambient_temperature 119(1) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator 'Ni filter' _diffrn_measurement_device 'Siemens P4/RA' _diffrn_measurement_method theta/2theata _diffrn_standards_number 2 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 888 _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_sigmaI/netI 0.0205 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 6.53 _diffrn_reflns_theta_max 55.05 _reflns_number_total 820 _reflns_number_observed 727 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-96 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-96 (Sheldrick, 1996)' _computing_molecular_graphics 'SHELXTL' _computing_publication_material 'SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. 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^)+(0.1294P)^2^+1.3175P] 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 0.0007(11) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 820 _refine_ls_number_parameters 83 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_obs 0.0551 _refine_ls_wR_factor_all 0.1743 _refine_ls_wR_factor_obs 0.1653 _refine_ls_goodness_of_fit_all 1.061 _refine_ls_goodness_of_fit_obs 1.075 _refine_ls_restrained_S_all 1.061 _refine_ls_restrained_S_obs 1.075 _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean 0.001 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 S S 0.0605(3) 0.65897(13) 0.4596(3) 0.0445(7) Uani 1 d . . C2 C 0.1022(11) 0.5326(5) 0.5597(11) 0.0401(18) Uani 1 d . . C3 C 0.1697(10) 0.5440(5) 0.7833(11) 0.0406(18) Uani 1 d . . C4 C 0.1754(11) 0.6357(5) 0.8517(11) 0.0399(17) Uani 1 d . . C5 C 0.1187(11) 0.7134(5) 0.6968(12) 0.0446(18) Uani 1 d . . Cl1 Cl 0.2993(3) 0.47556(13) 0.5230(3) 0.0466(7) Uani 1 d . . Cl2 Cl 0.2451(3) 0.44534(13) 0.9442(3) 0.0464(7) Uani 1 d . . Cl3 Cl 0.2451(3) 0.66913(14) 1.0941(3) 0.0520(7) Uani 1 d . . O O 0.1132(9) 0.8005(4) 0.7199(9) 0.0573(15) Uani 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 S 0.0476(12) 0.0399(12) 0.0460(13) 0.0010(8) 0.0224(9) -0.0032(8) C2 0.040(4) 0.034(4) 0.054(5) -0.003(3) 0.028(4) -0.001(3) C3 0.031(4) 0.043(4) 0.047(5) 0.005(3) 0.019(4) -0.001(3) C4 0.038(4) 0.044(4) 0.038(4) -0.003(3) 0.018(3) -0.004(3) C5 0.043(5) 0.046(5) 0.044(5) -0.002(4) 0.020(4) -0.002(3) Cl1 0.0325(12) 0.0571(12) 0.0549(13) -0.0023(8) 0.0244(10) 0.0013(7) Cl2 0.0466(12) 0.0432(11) 0.0438(12) 0.0035(7) 0.0169(9) -0.0002(7) Cl3 0.0601(14) 0.0518(12) 0.0435(12) -0.0049(8) 0.0241(10) -0.0051(8) O 0.072(4) 0.042(3) 0.057(4) -0.002(3) 0.029(3) -0.001(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 S C5 1.7734(78) . ? S C2 1.8357(68) . ? C2 C3 1.5076(103) . ? C2 C2 1.5989(134) 3_566 ? C2 Cl1 1.7731(66) . ? C3 C4 1.3372(101) . ? C3 Cl2 1.7053(71) . ? C4 C5 1.4711(107) . ? C4 Cl3 1.6921(72) . ? C5 O 1.1976(88) . ? 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 C5 S C2 93.9(3) . . ? C3 C2 C2 113.6(7) . 3_566 ? C3 C2 Cl1 110.7(5) . . ? C2 C2 Cl1 106.9(6) 3_566 . ? C3 C2 S 105.0(5) . . ? C2 C2 S 111.0(6) 3_566 . ? Cl1 C2 S 109.6(4) . . ? C4 C3 C2 117.0(6) . . ? C4 C3 Cl2 121.3(6) . . ? C2 C3 Cl2 121.7(5) . . ? C3 C4 C5 114.8(7) . . ? C3 C4 Cl3 126.6(6) . . ? C5 C4 Cl3 118.6(5) . . ? O C5 C4 127.5(7) . . ? O C5 S 123.1(6) . . ? C4 C5 S 109.4(5) . . ? _refine_diff_density_max 0.498 _refine_diff_density_min -0.513 _refine_diff_density_rms 0.150