Electronic Supplementary Material for CrystEngComm This Journal is © The Royal Society of Chemistry 2004 data_jr0338 _database_code_depnum_ccdc_archive 'CCDC 229181' _audit_creation_method SHELXL-97 #============================================================================== _chemical_name_systematic ; 4-chloro-1,2,3,5-dithiadiazolyl ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C Cl N2 S2' _chemical_formula_sum 'C Cl N2 S2' _chemical_formula_weight 139.60 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' N N 0.0061 0.0033 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.3393(2) _cell_length_b 9.4759(2) _cell_length_c 11.9105(3) _cell_angle_alpha 102.7998(9) _cell_angle_beta 90.1883(10) _cell_angle_gamma 104.7607(11) _cell_volume 885.74(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 6822 _cell_measurement_theta_min 1.02 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.46 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.094 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552 _exptl_absorpt_coefficient_mu 1.619 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.582 _exptl_absorpt_correction_T_max 0.696 _exptl_absorpt_process_details ; multi-scan from symmetry-related measurements Sortav (Blessing 1995) ; _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 'Nonius Kappa CCD' _diffrn_measurement_method 'Thin slice \w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_reflns_number 9276 _diffrn_reflns_av_R_equivalents 0.0325 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.52 _diffrn_reflns_theta_max 27.48 _reflns_number_total 3994 _reflns_number_gt 3781 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius B.V. 1998)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction ; HKL Denzo and Scalepack (Otwinski & Minor 1997) ; _computing_structure_solution 'SHELXS-97 (Sheldrick 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick 1997)' _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^)+(0.0274P)^2^+0.5063P] 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 3994 _refine_ls_number_parameters 217 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0278 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0681 _refine_ls_wR_factor_gt 0.0669 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 Cl1 Cl -0.04713(6) 0.67270(6) 0.69024(6) 0.04434(14) Uani 1 1 d . . . C11 C 0.0777(2) 0.55154(19) 0.65682(15) 0.0237(3) Uani 1 1 d . . . N11 N 0.21691(19) 0.60018(17) 0.60725(13) 0.0279(3) Uani 1 1 d . . . N12 N 0.02667(17) 0.42116(16) 0.68445(13) 0.0232(3) Uani 1 1 d . . . S11 S 0.32517(6) 0.47544(5) 0.58200(4) 0.02946(11) Uani 1 1 d . . . S12 S 0.15854(5) 0.31592(5) 0.65153(4) 0.02379(10) Uani 1 1 d . . . Cl2 Cl 0.14417(6) 0.35977(5) 0.96877(4) 0.03139(11) Uani 1 1 d . . . C21 C 0.2743(2) 0.49562(18) 0.91302(14) 0.0217(3) Uani 1 1 d . . . N21 N 0.40787(18) 0.46305(17) 0.86372(13) 0.0259(3) Uani 1 1 d . . . N22 N 0.23315(18) 0.62264(16) 0.92037(12) 0.0238(3) Uani 1 1 d . . . S21 S 0.51786(5) 0.59911(5) 0.81184(4) 0.02510(10) Uani 1 1 d . . . S22 S 0.36496(5) 0.74139(5) 0.86189(4) 0.02296(10) Uani 1 1 d . . . Cl3 Cl 0.15831(6) 1.02124(5) 1.09678(4) 0.03441(12) Uani 1 1 d . . . C31 C 0.2263(2) 1.04076(18) 1.23714(15) 0.0215(3) Uani 1 1 d . . . N31 N 0.12315(17) 0.96701(17) 1.30200(13) 0.0251(3) Uani 1 1 d . . . N32 N 0.37796(18) 1.12510(16) 1.26987(12) 0.0235(3) Uani 1 1 d . . . S31 S 0.20339(5) 0.99293(5) 1.43319(4) 0.02472(10) Uani 1 1 d . . . S32 S 0.43028(5) 1.13623(5) 1.40622(4) 0.02347(10) Uani 1 1 d . . . Cl4 Cl 0.73868(5) 0.96484(5) 1.22978(4) 0.03098(11) Uani 1 1 d . . . C41 C 0.5462(2) 0.85427(18) 1.24498(14) 0.0205(3) Uani 1 1 d . . . N41 N 0.52245(17) 0.81790(16) 1.34714(12) 0.0223(3) Uani 1 1 d . . . N42 N 0.43424(17) 0.81443(16) 1.15831(12) 0.0220(3) Uani 1 1 d . . . S41 S 0.33173(5) 0.71833(5) 1.35440(3) 0.02102(10) Uani 1 1 d . . . S42 S 0.25667(5) 0.70950(5) 1.18589(3) 0.02064(10) 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 Cl1 0.0291(2) 0.0300(2) 0.0765(4) 0.0109(2) -0.0045(2) 0.01348(19) C11 0.0217(8) 0.0226(8) 0.0261(8) 0.0050(6) -0.0044(6) 0.0049(6) N11 0.0293(8) 0.0259(7) 0.0295(8) 0.0129(6) 0.0012(6) 0.0033(6) N12 0.0174(6) 0.0233(7) 0.0280(7) 0.0065(6) 0.0008(5) 0.0032(5) S11 0.0287(2) 0.0302(2) 0.0276(2) 0.00682(18) 0.01202(17) 0.00394(18) S12 0.0227(2) 0.01913(19) 0.0285(2) 0.00490(16) 0.00453(16) 0.00417(15) Cl2 0.0330(2) 0.0280(2) 0.0315(2) 0.01445(18) 0.00278(17) -0.00143(18) C21 0.0226(8) 0.0215(8) 0.0199(7) 0.0069(6) -0.0017(6) 0.0020(6) N21 0.0233(7) 0.0230(7) 0.0340(8) 0.0126(6) 0.0009(6) 0.0058(6) N22 0.0260(7) 0.0226(7) 0.0230(7) 0.0069(6) 0.0045(5) 0.0053(6) S21 0.01790(19) 0.0249(2) 0.0341(2) 0.01081(17) 0.00235(16) 0.00500(16) S22 0.0267(2) 0.01896(19) 0.0240(2) 0.00672(15) 0.00296(16) 0.00574(16) Cl3 0.0368(3) 0.0363(3) 0.0300(2) 0.01164(19) -0.01260(18) 0.00604(19) C31 0.0204(8) 0.0190(7) 0.0256(8) 0.0053(6) -0.0026(6) 0.0058(6) N31 0.0182(7) 0.0262(7) 0.0315(8) 0.0081(6) -0.0007(6) 0.0056(6) N32 0.0247(7) 0.0227(7) 0.0219(7) 0.0076(6) -0.0013(5) 0.0018(6) S31 0.0232(2) 0.0260(2) 0.0241(2) 0.00553(16) 0.00666(16) 0.00499(16) S32 0.0243(2) 0.0216(2) 0.0203(2) 0.00434(15) -0.00203(15) -0.00100(16) Cl4 0.0178(2) 0.0322(2) 0.0471(3) 0.0203(2) 0.00519(17) 0.00433(16) C41 0.0185(7) 0.0204(7) 0.0256(8) 0.0087(6) 0.0033(6) 0.0075(6) N41 0.0178(6) 0.0253(7) 0.0242(7) 0.0086(6) -0.0014(5) 0.0037(5) N42 0.0213(7) 0.0251(7) 0.0216(7) 0.0085(5) 0.0037(5) 0.0072(6) S41 0.01995(19) 0.0225(2) 0.02044(19) 0.00858(15) -0.00038(14) 0.00209(15) S42 0.01999(19) 0.0215(2) 0.01883(19) 0.00365(15) -0.00183(14) 0.00345(15) _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 C11 1.7233(18) . ? C11 N12 1.315(2) . ? C11 N11 1.327(2) . ? N11 S11 1.6403(17) . ? N12 S12 1.6570(15) . ? N12 S41 2.9328(14) 2_567 ? N12 S42 2.9802(15) 2_567 ? S11 S12 2.0960(6) . ? S11 S21 3.0065(7) . ? S11 N41 3.5897(15) 2_667 ? S12 N41 3.2270(15) 2_667 ? Cl2 C21 1.7167(17) . ? C21 N22 1.318(2) . ? C21 N21 1.334(2) . ? N21 S21 1.6247(15) . ? N22 S22 1.6376(15) . ? N22 S42 3.0785(15) . ? S21 S22 2.0794(6) . ? S22 N42 3.4608(15) . ? Cl3 C31 1.7187(17) . ? C31 N32 1.316(2) . ? C31 N31 1.328(2) . ? N31 S31 1.6398(15) . ? N32 S32 1.6539(14) . ? N32 S22 2.8599(15) 2_677 ? N32 S21 2.9166(15) 2_677 ? S31 S32 2.1012(6) . ? S31 S41 3.0234(6) . ? Cl4 C41 1.7136(17) . ? C41 N42 1.312(2) . ? C41 N41 1.338(2) . ? N41 S41 1.6430(14) . ? N41 S32 2.8832(15) 2_678 ? N41 S31 3.3287(14) 2_678 ? N42 S42 1.6392(14) . ? S41 S42 2.0778(5) . ? 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 N12 C11 N11 126.57(16) . . ? N12 C11 Cl1 116.77(13) . . ? N11 C11 Cl1 116.65(13) . . ? C11 N11 S11 111.66(12) . . ? C11 N12 S12 112.58(12) . . ? C11 N12 S41 115.18(11) . 2_567 ? S12 N12 S41 119.53(7) . 2_567 ? C11 N12 S42 133.21(12) . 2_567 ? S12 N12 S42 113.86(7) . 2_567 ? S41 N12 S42 41.14(2) 2_567 2_567 ? N11 S11 S12 95.42(6) . . ? N11 S11 S21 92.85(6) . . ? S12 S11 S21 89.95(2) . . ? N11 S11 N41 152.77(6) . 2_667 ? S12 S11 N41 62.85(3) . 2_667 ? S21 S11 N41 72.17(3) . 2_667 ? N12 S12 S11 93.77(5) . . ? N12 S12 N41 162.93(6) . 2_667 ? S11 S12 N41 81.84(3) . 2_667 ? N22 C21 N21 125.13(16) . . ? N22 C21 Cl2 117.64(13) . . ? N21 C21 Cl2 117.22(13) . . ? C21 N21 S21 112.30(12) . . ? C21 N22 S22 112.91(12) . . ? C21 N22 S42 95.04(10) . . ? S22 N22 S42 113.62(7) . . ? N21 S21 S22 95.33(6) . . ? N21 S21 S11 91.58(6) . . ? S22 S21 S11 90.25(2) . . ? N22 S22 S21 94.33(6) . . ? N22 S22 N42 67.27(6) . . ? S21 S22 N42 99.56(3) . . ? N32 C31 N31 125.85(16) . . ? N32 C31 Cl3 116.85(13) . . ? N31 C31 Cl3 117.28(13) . . ? C31 N31 S31 112.55(12) . . ? C31 N32 S32 112.75(12) . . ? C31 N32 S22 130.36(11) . 2_677 ? S32 N32 S22 116.44(7) . 2_677 ? C31 N32 S21 116.93(11) . 2_677 ? S32 N32 S21 116.61(7) . 2_677 ? S22 N32 S21 42.18(2) 2_677 2_677 ? N31 S31 S32 94.77(6) . . ? N31 S31 S41 89.26(5) . . ? S32 S31 S41 91.97(2) . . ? N32 S32 S31 94.05(5) . . ? N42 C41 N41 125.37(15) . . ? N42 C41 Cl4 118.54(13) . . ? N41 C41 Cl4 116.08(12) . . ? C41 N41 S41 112.04(11) . . ? C41 N41 S32 155.47(11) . 2_678 ? S41 N41 S32 88.69(6) . 2_678 ? C41 N41 S31 118.32(10) . 2_678 ? S41 N41 S31 127.11(7) . 2_678 ? S32 N41 S31 38.71(2) 2_678 2_678 ? C41 N42 S42 112.87(12) . . ? C41 N42 S22 145.88(11) . . ? S42 N42 S22 97.78(6) . . ? N41 S41 S42 94.84(5) . . ? N41 S41 S31 93.19(5) . . ? S42 S41 S31 88.811(19) . . ? N42 S42 S41 94.79(5) . . ? N42 S42 N22 79.24(6) . . ? S41 S42 N22 158.97(4) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.376 _refine_diff_density_min -0.421 _refine_diff_density_rms 0.079