# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Yamada, Jun-ichi' 'Akutsu, Hiroki' 'Ikemoto, Isao' 'Kikuchi, Koichi' 'Nakatsuji, S.' 'Nishikawa, Hiroyuki' 'Toita, Takashi' 'Watanabe, Maki' _publ_contact_author_name 'Jun-ichi Yamada' _publ_contact_author_address ; Department of Material Science Faculty of Science Himeji Institute Institute of Technology Kouto 3-2-1, Kamigori-cho, Ako-gun, Hyogo 678-1297 Japan ; _publ_contact_author_phone '(81) 791 58 0162' _publ_contact_author_fax '(81) 791 58 0164' _publ_contact_author_email 'yamada@sci.himeji-tech.ac.jp' _publ_section_title ; 2-(1,3-Dithiolan-2-ylidene)-5-(1,3-dithian-2-ylidene)-1,3,4,6- tetrathiapentalene (DHDA-TTP), a hybrid of BDH-TTP and BDA-TTP, and its metallic cation-radical salts ; _publ_requested_journal 'Chemical Communications' _publ_section_comment ; The study of the titled structure was undertaken to establish its three dimensional structure. Geometries are tabulated below. All Diagrams and calculations were performed using teXsan for Windows. ; _publ_section_references ; Molecular Structure Corporation. (1997-1999). teXsan for Windows. Single Crystal Structure Analysis Software. Version 1.06. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA. North, A.C.T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359. Altomare, A., Cascarano, M., Giacovazzo, C., Guagliardi, A. (1994). J. Appl. Cryst., 26, 343. ; data_(DHDA-TTP)2PF6 _database_code_CSD 178065 _computing_data_collection 'CAD4 Diffractometer Control' _computing_cell_refinement 'CAD4 Diffractometer Control' _computing_data_reduction 'teXsan for Windows' _computing_structure_solution ; SIR92 (Altomare, et. al. 1994) ; _computing_structure_refinement 'teXsan for Windows' _computing_publication_material 'teXsan for Windows' _cell_length_a 7.930(6) _cell_length_b 17.548(5) _cell_length_c 6.456(2) _cell_angle_alpha 96.29(3) _cell_angle_beta 108.71(5) _cell_angle_gamma 91.28(4) _cell_volume 844.1(8) _cell_formula_units_Z 1 _cell_measurement_temperature 295 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.0 _cell_measurement_theta_max 15.8 _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -z' _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _exptl_crystal_description 'plate' _exptl_crystal_colour 'black' _exptl_crystal_size_max 0.5 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_diffrn 1.854 _exptl_crystal_density_meas 'not measured' _chemical_formula_weight 942.32 _chemical_formula_sum 'C22 H20 F6 P S16 ' _exptl_crystal_F_000 477.00 _exptl_absorpt_coefficient_mu 1.125 _exptl_absorpt_correction_type none _diffrn_ambient_temperature 295 _diffrn_radiation_wavelength 0.7107 _diffrn_radiation_type 'Mo K?a' _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_monochromator graphite _diffrn_radiation_detector 'scintillation counter' _diffrn_measurement_device 'CAD4' _diffrn_measurement_method ?w-2?q _diffrn_standards_number 3 _diffrn_standards_interval_time 120 _diffrn_standards_decay_% -0.26 _diffrn_reflns_number 5304 _reflns_number_total 4896 _reflns_number_gt 3313 _reflns_threshold_expression I>3.00?s(I) _diffrn_reflns_av_R_equivalents 0.01244 _diffrn_reflns_av_sigmaI/netI 0.043 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.17 _diffrn_reflns_theta_max 29.96 _diffrn_reflns_reduction_process 'Lp corrections applied' _diffrn_orient_matrix_UB_11 0.03096 _diffrn_orient_matrix_UB_12 0.01227 _diffrn_orient_matrix_UB_13 0.16331 _diffrn_orient_matrix_UB_21 0.01402 _diffrn_orient_matrix_UB_22 0.05585 _diffrn_orient_matrix_UB_23 -0.01329 _diffrn_orient_matrix_UB_31 -0.12899 _diffrn_orient_matrix_UB_32 0.00539 _diffrn_orient_matrix_UB_33 -0.01769 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_refinement_flags _atom_site_adp_type _atom_site_calc_flag _atom_site_calc_attached_atom S(1) 0.07528(7) -0.18159(3) -0.75318(7) 0.0508(1) 1.000 . Uani d ? S(2) -0.00966(8) -0.21340(3) -0.35827(8) 0.0626(2) 1.000 . Uani d ? S(3) 0.26626(6) -0.01779(2) -0.50153(7) 0.04280(13) 1.000 . Uani d ? S(4) 0.15385(7) -0.04632(3) -0.11817(7) 0.04651(13) 1.000 . Uani d ? S(5) 0.44996(7) 0.13600(2) -0.25568(7) 0.04557(13) 1.000 . Uani d ? S(6) 0.33944(6) 0.10707(2) 0.13040(6) 0.04075(12) 1.000 . Uani d ? S(7) 0.60698(7) 0.30220(3) -0.02441(7) 0.0466(1) 1.000 . Uani d ? S(8) 0.49946(7) 0.26896(3) 0.37209(7) 0.04699(13) 1.000 . Uani d ? P(1) 1.0000 0.5000 1.0000 0.0573(2) 0.500 S Uani d ? F(1) 0.8296(2) 0.45908(8) 0.8155(2) 0.0955(5) 1.000 . Uani d ? F(2) 1.1229(2) 0.46041(7) 0.8741(2) 0.0926(5) 1.000 . Uani d ? F(3) 0.9892(2) 0.57183(7) 0.8679(2) 0.0937(5) 1.000 . Uani d ? C(1) -0.0891(4) -0.28699(12) -0.5929(4) 0.0772(9) 1.000 . Uani d ? C(2) 0.0057(4) -0.27886(12) -0.7522(4) 0.0703(8) 1.000 . Uani d ? C(3) 0.0851(2) -0.15046(9) -0.4836(3) 0.0365(5) 1.000 . Uani d ? C(4) 0.1606(2) -0.08067(9) -0.3810(3) 0.0370(5) 1.000 . Uani d ? C(5) 0.3251(2) 0.05187(9) -0.2744(3) 0.0367(5) 1.000 . Uani d ? C(6) 0.2766(2) 0.03826(8) -0.0994(2) 0.0347(4) 1.000 . Uani d ? C(7) 0.4354(2) 0.17213(8) 0.0039(2) 0.0336(4) 1.000 . Uani d ? C(8) 0.4980(2) 0.24356(9) 0.1016(2) 0.0356(4) 1.000 . Uani d ? C(9) 0.4516(3) 0.36878(12) 0.3725(3) 0.0614(7) 1.000 . Uani d ? C(10) 0.5635(3) 0.41644(11) 0.2850(3) 0.0617(7) 1.000 . Uani d ? C(11) 0.5340(3) 0.39526(10) 0.0436(3) 0.0514(6) 1.000 . Uani d ? H(1) 0.025(2) -0.3071(10) -0.519(3) 0.051 1.000 . Uiso d ? H(2) -0.106(2) -0.3359(10) -0.536(3) 0.051 1.000 . Uiso d ? H(3) -0.043(2) -0.3024(10) -0.885(3) 0.051 1.000 . Uiso d ? H(4) 0.125(2) -0.3094(10) -0.695(3) 0.051 1.000 . Uiso d ? H(5) 0.317(2) 0.3777(9) 0.295(3) 0.051 1.000 . Uiso d ? H(6) 0.464(2) 0.3856(9) 0.516(3) 0.051 1.000 . Uiso d ? H(7) 0.521(2) 0.4712(10) 0.296(3) 0.051 1.000 . Uiso d ? H(8) 0.688(2) 0.4060(10) 0.361(3) 0.051 1.000 . Uiso d ? H(9) 0.398(2) 0.3950(9) -0.042(3) 0.051 1.000 . Uiso d ? H(10) 0.599(2) 0.4258(10) -0.012(3) 0.051 1.000 . Uiso 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0706(4) 0.0406(3) 0.0374(3) -0.0066(2) 0.0169(2) -0.0075(2) S(2) 0.0778(4) 0.0574(3) 0.0548(3) -0.0248(3) 0.0320(3) -0.0112(2) S(3) 0.0611(3) 0.0325(2) 0.0336(2) -0.0031(2) 0.0173(2) -0.0057(2) S(4) 0.0638(3) 0.0366(2) 0.0393(3) -0.0119(2) 0.0218(2) -0.0072(2) S(5) 0.0688(3) 0.0319(2) 0.0400(3) -0.0073(2) 0.0272(2) -0.0057(2) S(6) 0.0590(3) 0.0315(2) 0.0296(2) -0.0062(2) 0.0143(2) -0.0034(2) S(7) 0.0596(3) 0.0377(2) 0.0475(3) -0.0053(2) 0.0272(2) -0.0012(2) S(8) 0.0676(3) 0.0386(2) 0.0323(2) -0.0095(2) 0.0165(2) -0.0044(2) P(1) 0.0457(5) 0.0427(4) 0.0757(5) -0.0033(3) 0.0164(4) -0.0147(4) F(1) 0.0686(9) 0.0992(10) 0.0949(10) -0.0275(8) 0.0087(8) -0.0282(8) F(2) 0.0821(10) 0.0772(9) 0.1239(12) 0.0018(7) 0.0540(9) -0.0264(8) F(3) 0.1136(12) 0.0622(9) 0.1049(11) 0.0029(8) 0.0349(9) 0.0114(8) C(1) 0.110(2) 0.0363(12) 0.087(2) -0.0220(12) 0.041(2) -0.0079(11) C(2) 0.093(2) 0.0437(12) 0.073(2) -0.0181(11) 0.038(2) -0.0274(11) C(3) 0.0379(10) 0.0320(8) 0.0354(9) 0.0019(7) 0.0085(7) -0.0037(7) C(4) 0.0415(10) 0.0331(9) 0.0337(9) 0.0012(7) 0.0113(7) -0.0036(7) C(5) 0.0452(10) 0.0284(8) 0.0349(9) 0.0006(7) 0.0130(8) -0.0032(6) C(6) 0.0435(10) 0.0256(8) 0.0308(8) 0.0004(7) 0.0088(7) -0.0045(6) C(7) 0.0409(10) 0.0288(8) 0.0299(8) 0.0023(7) 0.0109(7) 0.0011(6) C(8) 0.0412(10) 0.0322(8) 0.0313(8) -0.0003(7) 0.0104(7) -0.0001(6) C(9) 0.091(2) 0.0481(12) 0.0454(12) 0.0085(11) 0.0267(12) -0.0075(9) C(10) 0.094(2) 0.0342(10) 0.0538(13) 0.0004(11) 0.0227(12) -0.0041(9) C(11) 0.067(1) 0.0366(10) 0.0540(12) -0.0014(9) 0.0242(10) 0.0064(8) # REFINEMENT DATA _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w = 1/[?s^2^(Fo) + 0.00001|Fo|^2^]' _refine_ls_hydrogen_treatment refxyz _refine_ls_extinction_method none _refine_ls_extinction_coef no _refine_ls_number_reflns 3313 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_number_constraints 0 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_ref 0.0430 _refine_ls_goodness_of_fit_ref 3.700 _refine_ls_shift/su_max 0.0300 _refine_ls_shift/su_mean 0.0022 _refine_diff_density_min -0.36 _refine_diff_density_max 0.75 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C2 1.783(4) . . ? S1 C3 1.742(3) . . ? S2 C1 1.812(4) . . ? S2 C3 1.729(3) . . ? S3 C4 1.758(3) . . ? S3 C5 1.733(3) . . ? S4 C4 1.755(3) . . ? S4 C6 1.728(3) . . ? S5 C5 1.730(3) . . ? S5 C7 1.765(3) . . ? S6 C6 1.736(3) . . ? S6 C7 1.765(3) . . ? S7 C8 1.750(3) . . ? S7 C11 1.801(4) . . ? S8 C8 1.751(3) . . ? S8 C9 1.800(4) . . ? P1 F1 1.580(3) . . ? P1 F2 1.584(2) . . ? P1 F3 1.586(3) . . ? C1 C2 1.472(6) . . ? C1 H1 0.97(3) . . no C1 H2 1.00(3) . . no C2 H3 0.87(3) . . no C2 H4 1.07(3) . . no C3 C4 1.354(4) . . ? C5 C6 1.348(4) . . ? C7 C8 1.347(4) . . ? C9 C10 1.482(6) . . ? C9 H5 1.05(3) . . no C9 H6 0.91(3) . . no C10 C11 1.502(5) . . ? C10 H7 1.03(3) . . no C10 H8 0.98(3) . . no C11 H9 1.04(3) . . no C11 H10 0.91(3) . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 S1 C3 95.9(2) . . . ? C1 S2 C3 96.7(2) . . . ? C4 S3 C5 94.0(1) . . . ? C4 S4 C6 94.3(2) . . . ? C5 S5 C7 93.9(2) . . . ? C6 S6 C7 93.8(1) . . . ? C8 S7 C11 101.5(2) . . . ? C8 S8 C9 102.1(2) . . . ? F1 P1 F1 180.00 . . 2_767. ? F1 P1 F2 89.8(1) . . . ? F1 P1 F2 90.2(1) . . 2_767 ? F1 P1 F3 91.0(1) . . . ? F1 P1 F3 89.0(1) . . 2_767 ? F1 P1 F2 90.2(1) 2_767 . . ? F1 P1 F2 89.8(1) 2_767 . 2_767 ? F1 P1 F3 89.0(1) 2_767 . . ? F1 P1 F3 91.0(1) 2_767 . 2_767 ? F2 P1 F2 180.00 . . 2_767 ? F2 P1 F3 90.1(1) . . . ? F2 P1 F3 89.9(1) . . 2_767 ? F2 P1 F3 89.9(1) 2_767 . . ? F2 P1 F3 90.1(1) 2_767 . 2_767 ? F3 P1 F3 180.00 . . 2_767 ? S2 C1 C2 111.1(3) . . . ? S1 C2 C1 112.6(3) . . . ? S1 C3 S2 116.0(2) . . . ? S1 C3 C4 121.6(3) . . . ? S2 C3 C4 122.4(2) . . . ? S3 C4 S4 115.6(2) . . . ? S3 C4 C3 123.0(2) . . . ? S4 C4 C3 121.4(3) . . . ? S3 C5 S5 123.7(2) . . . ? S3 C5 C6 118.0(2) . . . ? S5 C5 C6 118.2(2) . . . ? S4 C6 S6 123.9(2) . . . ? S4 C6 C5 118.0(2) . . . ? S6 C6 C5 118.1(2) . . . ? S5 C7 S6 115.3(2) . . . ? S5 C7 C8 122.4(2) . . . ? S6 C7 C8 122.3(2) . . . ? S7 C8 S8 121.5(2) . . . ? S7 C8 C7 119.6(2) . . . ? S8 C8 C7 118.1(2) . . . ? S8 C9 C10 115.3(3) . . . ? C9 C10 C11 113.7(3) . . . ? S7 C11 C10 114.3(3) . . . ?