# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2001 data_dop195mer _database_code_CSD 172092 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 3a,5,5,6,7a-pentachloro-tetrahydro(1,3)dithiolo(4,5-b)(1,4)dithiin-2-one ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C5 H Cl5 O S4' _chemical_formula_weight 382.55 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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.5432(13) _cell_length_b 16.283(3) _cell_length_c 11.420(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.81(3) _cell_angle_gamma 90.00 _cell_volume 1212.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5929 _cell_measurement_theta_min 2.5 _cell_measurement_theta_max 25.6 _exptl_crystal_description 'plate' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 1.850 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.6714 _exptl_absorpt_correction_T_max 0.9228 _exptl_absorpt_process_details 'FACEIT, Stoe-IPDS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Stoe-IPDS' _diffrn_measurement_method 'oscillation, phi incr. 1.4 deg.' _diffrn_detector_area_resol_mean 6.66 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9445 _diffrn_reflns_av_R_equivalents 0.0484 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.82 _reflns_number_total 2315 _reflns_number_gt 1493 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'EXPOSE, Stoe-IPDS' _computing_cell_refinement 'SELECT, CELL, Stoe-IPDS' _computing_data_reduction 'INTEGRATE, Stoe-IPDS' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0519P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2315 _refine_ls_number_parameters 140 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0655 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_ref 0.0983 _refine_ls_wR_factor_gt 0.0926 _refine_ls_goodness_of_fit_ref 0.892 _refine_ls_restrained_S_all 0.892 _refine_ls_shift/su_max 0.001 _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 0.18034(15) 0.70916(6) 0.61865(8) 0.0279(2) Uani 1 1 d . . . S2 S -0.14641(16) 0.70680(6) 0.83557(8) 0.0291(2) Uani 1 1 d . . . Cl4 Cl -0.11284(17) 0.87723(6) 0.85752(8) 0.0360(3) Uani 1 1 d . . . S3 S 0.16961(17) 0.88547(6) 0.62186(9) 0.0309(3) Uani 1 1 d . . . Cl7 Cl 0.1868(2) 0.53514(7) 0.62600(11) 0.0499(3) Uani 1 1 d . . . Cl5 Cl -0.1240(2) 0.53581(7) 0.84069(10) 0.0484(3) Uani 1 1 d . . . S4 S -0.25447(16) 0.81594(6) 0.62197(9) 0.0300(3) Uani 1 1 d . . . Cl6 Cl -0.2706(2) 0.60745(8) 0.61964(11) 0.0543(4) Uani 1 1 d . . . Cl2 Cl 0.32440(16) 0.79993(7) 0.83629(9) 0.0365(3) Uani 1 1 d . . . C1 C 0.1377(6) 0.7958(2) 0.7127(3) 0.0240(8) Uani 1 1 d . . . C3 C -0.0925(6) 0.6197(2) 0.7431(3) 0.0292(9) Uani 1 1 d . . . C2 C -0.0822(6) 0.7969(2) 0.7525(3) 0.0231(8) Uani 1 1 d . . . C4 C 0.1299(6) 0.6223(2) 0.7111(3) 0.0279(9) Uani 1 1 d . . . O1 O -0.1359(5) 0.92017(19) 0.4659(3) 0.0504(9) Uani 1 1 d . . . C5 C -0.0834(7) 0.8817(2) 0.5525(3) 0.0316(10) Uani 1 1 d . . . H1 H 0.258(8) 0.615(3) 0.814(4) 0.069(16) Uiso 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 S1 0.0341(6) 0.0263(5) 0.0248(5) 0.0007(4) 0.0107(4) 0.0049(5) S2 0.0357(6) 0.0260(5) 0.0273(5) 0.0032(4) 0.0124(4) -0.0008(5) Cl4 0.0511(7) 0.0289(6) 0.0292(5) -0.0078(4) 0.0109(5) 0.0046(5) S3 0.0371(6) 0.0275(6) 0.0282(5) 0.0082(4) 0.0034(5) -0.0058(5) Cl7 0.0663(9) 0.0292(6) 0.0563(7) -0.0078(5) 0.0182(6) 0.0099(6) Cl5 0.0615(8) 0.0282(6) 0.0569(8) 0.0116(5) 0.0132(6) -0.0083(5) S4 0.0273(6) 0.0305(6) 0.0312(5) 0.0021(4) -0.0030(4) 0.0040(4) Cl6 0.0516(8) 0.0514(8) 0.0568(8) -0.0037(6) -0.0141(6) -0.0073(6) Cl2 0.0326(6) 0.0429(7) 0.0320(6) 0.0038(5) -0.0095(4) -0.0032(5) C1 0.027(2) 0.0220(19) 0.0228(19) 0.0020(17) 0.0006(16) -0.0023(17) C3 0.036(2) 0.026(2) 0.025(2) 0.0030(17) -0.0011(17) -0.0040(18) C2 0.027(2) 0.022(2) 0.0198(18) -0.0019(16) 0.0022(15) 0.0001(17) C4 0.034(2) 0.020(2) 0.030(2) -0.0018(17) 0.0057(18) 0.0029(18) O1 0.073(2) 0.0402(19) 0.0350(17) 0.0143(15) -0.0130(16) -0.0037(17) C5 0.045(3) 0.023(2) 0.026(2) -0.0013(18) -0.0010(19) 0.0049(19) _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 1.810(4) . ? S1 C4 1.812(4) . ? S2 C2 1.815(4) . ? S2 C3 1.820(4) . ? Cl4 C2 1.797(4) . ? S3 C5 1.775(4) . ? S3 C1 1.813(4) . ? Cl7 C4 1.777(4) . ? Cl5 C3 1.785(4) . ? S4 C5 1.783(4) . ? S4 C2 1.819(4) . ? Cl6 C3 1.764(4) . ? Cl2 C1 1.788(4) . ? C1 C2 1.545(5) . ? C3 C4 1.530(6) . ? O1 C5 1.196(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 C1 S1 C4 102.59(17) . . ? C2 S2 C3 105.21(17) . . ? C5 S3 C1 94.58(18) . . ? C5 S4 C2 95.64(18) . . ? C2 C1 Cl2 111.1(2) . . ? C2 C1 S1 112.1(2) . . ? Cl2 C1 S1 111.6(2) . . ? C2 C1 S3 108.3(2) . . ? Cl2 C1 S3 108.53(19) . . ? S1 C1 S3 104.89(19) . . ? C4 C3 Cl6 112.9(3) . . ? C4 C3 Cl5 109.4(3) . . ? Cl6 C3 Cl5 108.0(2) . . ? C4 C3 S2 110.5(3) . . ? Cl6 C3 S2 113.8(2) . . ? Cl5 C3 S2 101.32(19) . . ? C1 C2 Cl4 111.3(3) . . ? C1 C2 S2 114.0(3) . . ? Cl4 C2 S2 101.31(18) . . ? C1 C2 S4 106.8(2) . . ? Cl4 C2 S4 109.1(2) . . ? S2 C2 S4 114.3(2) . . ? C3 C4 Cl7 110.8(3) . . ? C3 C4 S1 112.6(3) . . ? Cl7 C4 S1 104.4(2) . . ? O1 C5 S3 122.9(3) . . ? O1 C5 S4 122.3(3) . . ? S3 C5 S4 114.8(2) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.82 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.498 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.093 #===END