# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_hbpme _database_code_CSD 191497 _journal_coden_Cambridge 182 loop_ _publ_author_name _publ_author_address 'Beer, L.' ; Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; 'Brusso, J.L.' ; Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; 'Cordes, A.W.' ; Department of Chemistry and Biochemistry University of Arkansas Fayetteville, Arkansas 72701 USA ; 'Godde, Erika' ; Department of Chemistry University of California Riverside, California 92521 0403 USA ; 'Haddon, R.C.' ; Department of Chemistry University of California Riverside, California 92521 0403 USA ; 'Itkis, M.E.' ; Department of Chemistry University of California Riverside, California 92521 0403 USA ; 'Oakley, R.T.' ; Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; 'Reed, R.W.' ; Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; _publ_contact_author_name 'Prof Richard Oakley' _publ_contact_author_address ; Department of Chemistry University of Waterloo Waterloo Ontario N2L 3G1 CANADA ; _publ_contact_author_email 'oakley@sciborg.uwaterloo.ca' _publ_contact_author_fax '519-746-0435' _publ_contact_author_phone '519-888-4567 (ext. 4582)' _publ_requested_journal 'Chemical Communications' _publ_requested_coeditor_name ? _publ_section_title ; Structure - Property trends in pi-stacked dithiazolo-dithiazolyl conductors ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 N3 S4' _chemical_formula_weight 246.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'S' 'S' 0.1246 0.1234 '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' '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 3.9626(10) _cell_length_b 11.962(3) _cell_length_c 18.262(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 865.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4295 _cell_measurement_theta_min 4 _cell_measurement_theta_max 26 _exptl_crystal_description block _exptl_crystal_colour black _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.890 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 500 _exptl_absorpt_coefficient_mu 1.044 _exptl_absorpt_correction_type 'empirical, R.A.Jacobson, MS Corp, 1998' _exptl_absorpt_correction_T_min 0.82 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Mercury CCD - AFC8S' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 978 _diffrn_reflns_av_R_equivalents 0.036 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 26.00 _reflns_number_total 977 _reflns_number_gt 870 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'CrystalClear (Rigaku Corp, 1999)' _computing_cell_refinement 'CrystalClear (Rigaku Corp, 1999)' _computing_data_reduction 'Texsan (Molecular Structure Corp, 1998)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep3,v1.05, L.J.Farrugia,UnivGlasgow' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. wR and GOF are based on F^2^, conventional R's are based on F. The expression F^2^>2sigma(F^2^) is used only for the R-factor(gt). R's based on F^2^ are about twice as large as those based on F and R's 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^)+(0.0229P)^2^] 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 977 _refine_ls_number_parameters 134 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0338 _refine_ls_R_factor_gt 0.0271 _refine_ls_wR_factor_ref 0.0597 _refine_ls_wR_factor_gt 0.0579 _refine_ls_goodness_of_fit_ref 1.050 _refine_ls_restrained_S_all 1.050 _refine_ls_shift/su_max 0.038 _refine_ls_shift/su_mean 0.002 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_symetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.0198(3) 0.13661(8) 0.68501(5) 0.0402(3) Uani 1 1 d . . . S2 S -0.1469(3) -0.02936(8) 0.68581(5) 0.0381(2) Uani 1 1 d . . . S3 S -0.8345(3) -0.05170(9) 1.02279(5) 0.0442(3) Uani 1 1 d . . . S4 S -0.7625(3) -0.17382(8) 0.94149(5) 0.0386(3) Uani 1 1 d . . . N1 N -0.1013(8) 0.1726(2) 0.76870(15) 0.0370(8) Uani 1 1 d . . . N2 N -0.3775(8) 0.1134(2) 0.87474(15) 0.0326(7) Uani 1 1 d . . . N3 N -0.6568(9) 0.0555(2) 0.97993(15) 0.0391(8) Uani 1 1 d . . . C1 C -0.2576(9) 0.0926(3) 0.80450(16) 0.0280(7) Uani 1 1 d . . . C2 C -0.3033(9) -0.0158(3) 0.77421(17) 0.0264(8) Uani 1 1 d . . . C3 C -0.4626(10) -0.1001(3) 0.81298(19) 0.0317(8) Uani 1 1 d . . . C4 C -0.5730(9) -0.0776(3) 0.88348(18) 0.0294(8) Uani 1 1 d . . . C5 C -0.5384(9) 0.0312(3) 0.91501(17) 0.0293(8) Uani 1 1 d . . . C6 C -0.3340(16) 0.2253(4) 0.9063(3) 0.0485(12) Uani 1 1 d . . . H3 H -0.466(9) -0.170(3) 0.7921(16) 0.029(10) Uiso 1 1 d . . . H6A H -0.359(18) 0.220(5) 0.951(3) 0.11(2) Uiso 1 1 d . . . H6B H -0.091(18) 0.251(5) 0.909(3) 0.10(2) Uiso 1 1 d . . . H6C H -0.458(17) 0.278(5) 0.874(3) 0.12(2) 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 0.0456(6) 0.0381(5) 0.0369(5) 0.0044(4) 0.0079(5) -0.0003(5) S2 0.0464(6) 0.0384(5) 0.0295(4) -0.0027(4) 0.0055(5) -0.0021(5) S3 0.0475(6) 0.0561(6) 0.0291(4) 0.0052(5) 0.0049(5) 0.0051(6) S4 0.0417(6) 0.0414(6) 0.0328(4) 0.0076(4) 0.0010(5) -0.0014(5) N1 0.044(2) 0.0317(17) 0.0349(15) -0.0011(13) 0.0055(15) -0.0014(16) N2 0.0416(18) 0.0283(16) 0.0279(13) -0.0043(12) -0.0035(14) 0.0004(15) N3 0.047(2) 0.0429(18) 0.0273(14) 0.0004(14) 0.0042(16) 0.0030(18) C1 0.0263(18) 0.0310(17) 0.0269(15) 0.0012(14) -0.0001(17) 0.0027(16) C2 0.025(2) 0.0290(18) 0.0256(15) 0.0009(13) -0.0027(16) 0.0017(17) C3 0.036(2) 0.0283(18) 0.0308(17) -0.0018(15) -0.0028(19) 0.0026(17) C4 0.029(2) 0.032(2) 0.0273(16) 0.0032(15) -0.0040(16) -0.0002(16) C5 0.023(2) 0.036(2) 0.0284(16) 0.0030(15) -0.0072(16) 0.0062(18) C6 0.068(4) 0.031(2) 0.047(3) -0.013(2) 0.008(3) -0.008(3) _geom_special_details ; ; 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 N1 1.659(3) . ? S1 S2 2.0924(14) . ? S2 C2 1.737(3) . ? S3 N3 1.660(3) . ? S3 S4 2.1024(14) . ? S4 C4 1.735(4) . ? N1 C1 1.314(4) . ? N2 C5 1.383(4) . ? N2 C1 1.390(4) . ? N2 C6 1.468(5) . ? N3 C5 1.308(4) . ? C1 C2 1.421(4) . ? C2 C3 1.385(5) . ? C3 C4 1.386(5) . ? C3 H3 0.92(3) . ? C4 C5 1.430(5) . ? C6 H6A 0.83(5) . ? C6 H6B 1.01(7) . ? C6 H6C 0.99(6) . ? 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 N1 S1 S2 98.55(11) . . ? C2 S2 S1 91.74(12) . . ? N3 S3 S4 98.42(11) . . ? C4 S4 S3 91.66(13) . . ? C1 N1 S1 113.9(2) . . ? C5 N2 C1 121.4(3) . . ? C5 N2 C6 119.6(3) . . ? C1 N2 C6 119.0(3) . . ? C5 N3 S3 114.0(3) . . ? N1 C1 N2 119.4(3) . . ? N1 C1 C2 122.1(3) . . ? N2 C1 C2 118.6(3) . . ? C3 C2 C1 121.6(3) . . ? C3 C2 S2 124.7(3) . . ? C1 C2 S2 113.7(2) . . ? C2 C3 C4 118.5(3) . . ? C2 C3 H3 117(2) . . ? C4 C3 H3 124(2) . . ? C3 C4 C5 121.4(3) . . ? C3 C4 S4 125.1(3) . . ? C5 C4 S4 113.5(3) . . ? N3 C5 N2 119.3(3) . . ? N3 C5 C4 122.2(3) . . ? N2 C5 C4 118.5(3) . . ? N2 C6 H6A 107(4) . . ? N2 C6 H6B 114(4) . . ? H6A C6 H6B 96(5) . . ? N2 C6 H6C 107(3) . . ? H6A C6 H6C 125(6) . . ? H6B C6 H6C 108(5) . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.204 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.050