#Supplementary Material for Energy & Environmental Science #This journal is (c) The Royal Society of Chemistry 2010 data_BIRKIW _audit_creation_date 2010-06-30 _audit_creation_method 'Materials Studio' _symmetry_space_group_name_H-M 'P21/B' _symmetry_Int_Tables_number 14 _symmetry_cell_setting monoclinic loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y+1/2,z+1/2 -x,-y,-z x,y+1/2,-z+1/2 _cell_length_a 12.0930 _cell_length_b 14.5800 _cell_length_c 3.9480 _cell_angle_alpha 90.0000 _cell_angle_beta 90.0000 _cell_angle_gamma 114.2700 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 S1 S 0.03910 0.15780 0.61480 0.00000 Uiso 1.00 S2 S 0.18660 0.05890 0.31110 0.00000 Uiso 1.00 C1 C 0.23280 0.34150 0.50160 0.00000 Uiso 1.00 C2 C 0.34850 0.39810 0.37960 0.00000 Uiso 1.00 C3 C 0.41570 0.35150 0.23100 0.00000 Uiso 1.00 C4 C 0.36920 0.24830 0.20650 0.00000 Uiso 1.00 C5 C 0.25380 0.19040 0.32910 0.00000 Uiso 1.00 C6 C 0.18510 0.23790 0.47400 0.00000 Uiso 1.00 C7 C 0.04700 0.04530 0.48430 0.00000 Uiso 1.00 H1 H 0.18300 0.37900 0.61400 0.00000 Uiso 1.00 H2 H 0.37700 0.46000 0.36700 0.00000 Uiso 1.00 H3 H 0.49000 0.38200 0.15400 0.00000 Uiso 1.00 H4 H 0.41500 0.21600 0.09000 0.00000 Uiso 1.00 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C6 1.759 . S1 C7 1.759 . S2 C5 1.749 . S2 C7 1.755 . C1 C2 1.386 . C1 C6 1.382 . C1 H1 1.063 . C2 C3 1.386 . C2 H2 0.825 . C3 C4 1.376 . C3 H3 0.877 . C4 C5 1.388 . C4 H4 0.977 . C5 C6 1.404 . C7 C7 1.348 3_556 --------------------------------------------- #=================================================================== data_global #=================================================================== _publ_requested_journal ' Journal of the American Chemical Society ' _publ_contact_author ; ' Dr. Yoshiro Yamashita' Department of Electronic Chemistry Interdisciplinary Graduate School of Science and Engineering Tokyo Institute of Technology Nagatsuta, Midori-ku, Yokohama 226-8502, Japan ; _publ_contact_author_phone '+81-45-924-5571' _publ_contact_author_fax '+81-45-924-5489' _publ_contact_author_email yoshiro@echem.titech.ac.jp _publ_section_title ; High Performance Organic Film Field Effect Transistors Based on the p-extended Tetrathiafulvalene Derivatives ; loop_ _publ_author_name ' Naraso ' ' Jun-ichi Nishida ' ' Shinji Ando ' ' Jun Yamaguchi ' ' Hideomi Koinuma ' ' Hirokazu Tada ' ' Shizuo Tokito ' ' Yoshiro Yamashita ' _journal_name_full '?' _journal_volume '?' _journal_page_first '?' _journal_page_last '?' _journal_year '?' _ccdc_journal_depnumber '?' #------------------------------------------------------------------------------ data_2 #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C22 H12 S4 ' _chemical_formula_moiety '?' _chemical_formula_weight 404.58 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 5.929(9) _cell_length_b 7.85(1) _cell_length_c 18.07(3) _cell_angle_alpha 86.44(6) _cell_angle_beta 82.60(6) _cell_angle_gamma 85.47(6) _cell_volume 829(8) _cell_formula_units_Z 2 _cell_measurement_reflns_used 6458 _cell_measurement_theta_min 3.4 _cell_measurement_theta_max 27.6 _cell_measurement_temperature 93.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'block' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.100 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.619 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.575 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.568 _exptl_absorpt_correction_T_max 0.944 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 7391 _diffrn_reflns_av_R_equivalents 0.039 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.8987 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.8987 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3409 _reflns_number_gt 2492 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0794 _refine_ls_wR_factor_ref 0.2367 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3246 _refine_ls_number_parameters 235 _refine_ls_goodness_of_fit_ref 1.960 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0043 _refine_diff_density_max 0.77 _refine_diff_density_min -0.68 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'S' 'S' 0.125 0.123 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S(1) S 0.6011(2) -0.0005(2) 0.11235(9) 0.0190(4) Uani 1.00 d . . . S(2) S 0.2107(2) -0.1386(2) 0.05312(9) 0.0197(4) Uani 1.00 d . . . S(3) S 0.1321(2) -0.6594(2) 0.09060(9) 0.0198(4) Uani 1.00 d . . . S(4) S -0.3203(2) -0.4775(2) 0.07536(8) 0.0188(4) Uani 1.00 d . . . C(1) C 0.4601(9) -0.0298(7) 0.0346(3) 0.017(1) Uani 1.00 d . . . C(2) C 0.4071(10) -0.1052(7) 0.1784(3) 0.019(1) Uani 1.00 d . . . C(3) C 0.4299(10) -0.1219(6) 0.2516(3) 0.017(1) Uani 1.00 d . . . C(4) C 0.261(1) -0.2062(7) 0.3029(4) 0.020(2) Uani 1.00 d . . . C(5) C 0.277(1) -0.2282(7) 0.3799(4) 0.021(2) Uani 1.00 d . . . C(6) C 0.108(1) -0.3028(8) 0.4282(4) 0.026(2) Uani 1.00 d . . . C(7) C -0.0804(10) -0.3631(7) 0.3993(4) 0.022(2) Uani 1.00 d . . . C(8) C -0.0976(9) -0.3473(7) 0.3250(4) 0.019(2) Uani 1.00 d . . . C(9) C 0.0700(9) -0.2670(6) 0.2741(3) 0.015(1) Uani 1.00 d . . . C(10) C 0.0536(9) -0.2469(6) 0.1967(3) 0.015(1) Uani 1.00 d . . . C(11) C 0.2192(9) -0.1680(7) 0.1493(3) 0.018(1) Uani 1.00 d . . . C(12) C -0.0334(10) -0.5277(7) 0.0349(3) 0.019(1) Uani 1.00 d . . . C(13) C -0.0794(9) -0.6764(7) 0.1686(3) 0.017(1) Uani 1.00 d . . . C(14) C -0.0389(9) -0.7702(6) 0.2325(3) 0.017(1) Uani 1.00 d . . . C(15) C -0.2176(9) -0.7766(6) 0.2937(3) 0.015(1) Uani 1.00 d . . . C(16) C -0.182(1) -0.8689(7) 0.3614(3) 0.022(2) Uani 1.00 d . . . C(17) C -0.356(1) -0.8729(7) 0.4203(4) 0.023(2) Uani 1.00 d . . . C(18) C -0.570(1) -0.7842(8) 0.4137(4) 0.024(2) Uani 1.00 d . . . C(19) C -0.6054(10) -0.6921(7) 0.3480(3) 0.018(1) Uani 1.00 d . . . C(20) C -0.4326(9) -0.6880(6) 0.2874(3) 0.015(1) Uani 1.00 d . . . C(21) C -0.4669(9) -0.5920(7) 0.2186(3) 0.015(1) Uani 1.00 d . . . C(22) C -0.2960(9) -0.5862(6) 0.1610(3) 0.015(1) Uani 1.00 d . . . H(1) H 0.5559 -0.0815 0.2687 0.0177 Uiso 1.00 calc . . . H(2) H 0.4080 -0.1921 0.3985 0.0222 Uiso 1.00 calc . . . H(3) H 0.1093 -0.3098 0.4817 0.0301 Uiso 1.00 calc . . . H(4) H -0.1977 -0.4213 0.4325 0.0265 Uiso 1.00 calc . . . H(5) H -0.2281 -0.3877 0.3054 0.0240 Uiso 1.00 calc . . . H(6) H -0.0744 -0.2888 0.1756 0.0190 Uiso 1.00 calc . . . H(7) H 0.1126 -0.8278 0.2363 0.0227 Uiso 1.00 calc . . . H(8) H -0.0307 -0.9254 0.3677 0.0290 Uiso 1.00 calc . . . H(9) H -0.3257 -0.9392 0.4640 0.0317 Uiso 1.00 calc . . . H(10) H -0.6870 -0.7898 0.4547 0.0291 Uiso 1.00 calc . . . H(11) H -0.7414 -0.6295 0.3434 0.0246 Uiso 1.00 calc . . . H(12) H -0.6026 -0.5319 0.2127 0.0186 Uiso 1.00 calc . . . 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) 0.0150(7) 0.0228(7) 0.0198(8) -0.0042(6) -0.0038(6) 0.0014(6) S(2) 0.0133(7) 0.0249(8) 0.0215(9) -0.0046(6) -0.0037(6) 0.0006(6) S(3) 0.0154(8) 0.0243(8) 0.0186(8) 0.0030(6) -0.0024(6) 0.0022(6) S(4) 0.0120(7) 0.0243(8) 0.0190(8) 0.0019(6) -0.0018(6) 0.0022(6) C(1) 0.014(3) 0.013(2) 0.022(3) 0.002(2) -0.002(2) 0.002(2) C(2) 0.019(3) 0.014(3) 0.024(3) 0.001(2) -0.003(2) -0.001(2) C(3) 0.019(3) 0.011(2) 0.021(3) -0.005(2) -0.007(2) 0.000(2) C(4) 0.024(3) 0.011(2) 0.024(4) 0.002(2) -0.006(3) 0.002(2) C(5) 0.025(3) 0.020(3) 0.019(3) -0.003(2) -0.007(2) 0.004(2) C(6) 0.029(3) 0.034(3) 0.016(3) -0.001(3) -0.002(3) -0.004(3) C(7) 0.017(3) 0.024(3) 0.024(4) -0.001(2) 0.004(2) -0.001(2) C(8) 0.008(3) 0.020(3) 0.027(4) 0.001(2) 0.000(2) -0.003(2) C(9) 0.013(3) 0.006(2) 0.023(3) 0.005(2) 0.000(2) 0.003(2) C(10) 0.004(3) 0.013(3) 0.029(4) 0.005(2) -0.005(2) -0.001(2) C(11) 0.014(3) 0.022(3) 0.016(3) 0.004(2) -0.001(2) -0.002(2) C(12) 0.017(3) 0.024(3) 0.017(3) -0.005(2) 0.000(2) -0.005(2) C(13) 0.017(3) 0.018(3) 0.015(3) -0.006(2) 0.000(2) -0.001(2) C(14) 0.018(3) 0.008(2) 0.024(3) 0.004(2) -0.009(2) 0.001(2) C(15) 0.016(3) 0.008(2) 0.021(3) 0.001(2) -0.005(2) 0.003(2) C(16) 0.024(3) 0.027(3) 0.018(3) -0.008(3) -0.008(3) 0.002(2) C(17) 0.025(3) 0.030(3) 0.017(3) -0.005(3) -0.005(2) 0.000(2) C(18) 0.021(3) 0.029(3) 0.021(4) 0.004(3) -0.002(2) -0.005(3) C(19) 0.019(3) 0.011(2) 0.023(3) -0.001(2) -0.001(2) 0.004(2) C(20) 0.016(3) 0.008(2) 0.021(3) 0.003(2) -0.006(2) 0.003(2) C(21) 0.007(3) 0.016(3) 0.021(3) 0.003(2) -0.004(2) -0.002(2) C(22) 0.014(3) 0.015(3) 0.016(3) 0.000(2) -0.003(2) 0.000(2) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR97 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 S(1) C(1) 1.759(6) . . yes S(1) C(2) 1.760(6) . . yes S(2) C(1) 1.750(6) . . yes S(2) C(11) 1.746(6) . . yes S(3) C(12) 1.735(6) . . yes S(3) C(13) 1.768(6) . . yes S(4) C(12) 1.787(6) . . yes S(4) C(22) 1.736(6) . . yes C(1) C(1) 1.35(1) . 2_655 yes C(2) C(3) 1.344(8) . . yes C(2) C(11) 1.425(8) . . yes C(3) C(4) 1.446(8) . . yes C(4) C(5) 1.408(9) . . yes C(4) C(9) 1.429(8) . . yes C(5) C(6) 1.384(8) . . yes C(6) C(7) 1.417(9) . . yes C(7) C(8) 1.356(9) . . yes C(8) C(9) 1.422(7) . . yes C(9) C(10) 1.413(8) . . yes C(10) C(11) 1.376(8) . . yes C(12) C(12) 1.33(1) . 2_545 yes C(13) C(14) 1.368(8) . . yes C(13) C(22) 1.436(8) . . yes C(14) C(15) 1.430(8) . . yes C(15) C(16) 1.414(8) . . yes C(15) C(20) 1.417(8) . . yes C(16) C(17) 1.387(8) . . yes C(17) C(18) 1.412(9) . . yes C(18) C(19) 1.382(8) . . yes C(19) C(20) 1.401(8) . . yes C(20) C(21) 1.442(8) . . yes C(21) C(22) 1.358(8) . . yes #------------------------------------------------------------------------------ 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 C(1) S(1) C(2) 95.9(3) . . . yes C(1) S(2) C(11) 95.6(3) . . . yes C(12) S(3) C(13) 96.3(3) . . . yes C(12) S(4) C(22) 96.4(3) . . . yes S(1) C(1) S(2) 116.0(3) . . . yes S(1) C(1) C(1) 121.6(6) . . 2_655 yes S(2) C(1) C(1) 122.5(6) . . 2_655 yes S(1) C(2) C(3) 122.8(4) . . . yes S(1) C(2) C(11) 115.3(5) . . . yes C(3) C(2) C(11) 121.8(5) . . . yes C(2) C(3) C(4) 119.7(5) . . . yes C(3) C(4) C(5) 121.9(5) . . . yes C(3) C(4) C(9) 118.7(5) . . . yes C(5) C(4) C(9) 119.4(5) . . . yes C(4) C(5) C(6) 120.7(6) . . . yes C(5) C(6) C(7) 119.6(6) . . . yes C(6) C(7) C(8) 120.8(5) . . . yes C(7) C(8) C(9) 121.1(5) . . . yes C(4) C(9) C(8) 118.4(6) . . . yes C(4) C(9) C(10) 119.6(5) . . . yes C(8) C(9) C(10) 122.1(5) . . . yes C(9) C(10) C(11) 120.2(5) . . . yes S(2) C(11) C(2) 117.2(4) . . . yes S(2) C(11) C(10) 122.9(5) . . . yes C(2) C(11) C(10) 120.0(6) . . . yes S(3) C(12) S(4) 115.2(3) . . . yes S(3) C(12) C(12) 125.2(6) . . 2_545 yes S(4) C(12) C(12) 119.5(6) . . 2_545 yes S(3) C(13) C(14) 121.9(5) . . . yes S(3) C(13) C(22) 116.1(4) . . . yes C(14) C(13) C(22) 122.0(5) . . . yes C(13) C(14) C(15) 118.8(5) . . . yes C(14) C(15) C(16) 120.7(5) . . . yes C(14) C(15) C(20) 120.2(5) . . . yes C(16) C(15) C(20) 119.1(5) . . . yes C(15) C(16) C(17) 120.0(6) . . . yes C(16) C(17) C(18) 120.6(6) . . . yes C(17) C(18) C(19) 119.7(6) . . . yes C(18) C(19) C(20) 120.7(5) . . . yes C(15) C(20) C(19) 119.9(5) . . . yes C(15) C(20) C(21) 118.8(5) . . . yes C(19) C(20) C(21) 121.3(5) . . . yes C(20) C(21) C(22) 120.6(5) . . . yes S(4) C(22) C(13) 116.0(4) . . . yes S(4) C(22) C(21) 124.4(4) . . . yes C(13) C(22) C(21) 119.7(5) . . . yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S(1) C(1) S(2) C(11) 0.5(4) . . . . yes S(1) C(1) C(1) S(1) -180.0 . . 2_655 2_655 yes S(1) C(1) C(1) S(2) 0.6(10) . . 2_655 2_655 yes S(1) C(2) C(3) C(4) 178.6(4) . . . . yes S(1) C(2) C(11) S(2) 1.7(6) . . . . yes S(1) C(2) C(11) C(10) -177.9(4) . . . . yes S(2) C(1) S(1) C(2) 0.3(4) . . . . yes S(2) C(1) C(1) S(2) 180.0 . . 2_655 2_655 yes S(2) C(11) C(2) C(3) -179.7(4) . . . . yes S(2) C(11) C(10) C(9) 179.9(4) . . . . yes S(3) C(12) S(4) C(22) 2.5(4) . . . . yes S(3) C(12) C(12) S(3) 180.0 . . 2_545 2_545 yes S(3) C(12) C(12) S(4) -4(1) . . 2_545 2_545 yes S(3) C(13) C(14) C(15) 179.4(4) . . . . yes S(3) C(13) C(22) S(4) 1.3(6) . . . . yes S(3) C(13) C(22) C(21) -179.6(4) . . . . yes S(4) C(12) S(3) C(13) -1.9(4) . . . . yes S(4) C(12) C(12) S(4) -180.0 . . 2_545 2_545 yes S(4) C(22) C(13) C(14) -178.6(4) . . . . yes S(4) C(22) C(21) C(20) 179.0(4) . . . . yes C(1) S(1) C(2) C(3) -179.7(5) . . . . yes C(1) S(1) C(2) C(11) -1.1(5) . . . . yes C(1) S(2) C(11) C(2) -1.3(5) . . . . yes C(1) S(2) C(11) C(10) 178.3(5) . . . . yes C(1) C(1) S(2) C(11) 179.0(7) . 2_655 2_655 2_655 yes C(2) C(3) C(4) C(5) 179.5(5) . . . . yes C(2) C(3) C(4) C(9) -1.1(8) . . . . yes C(2) C(11) C(10) C(9) -0.5(8) . . . . yes C(3) C(2) C(11) C(10) 0.7(9) . . . . yes C(3) C(4) C(5) C(6) 177.3(5) . . . . yes C(3) C(4) C(9) C(8) -179.0(5) . . . . yes C(3) C(4) C(9) C(10) 1.3(7) . . . . yes C(4) C(3) C(2) C(11) 0.2(9) . . . . yes C(4) C(5) C(6) C(7) 2.2(9) . . . . yes C(4) C(9) C(8) C(7) 1.3(8) . . . . yes C(4) C(9) C(10) C(11) -0.5(8) . . . . yes C(5) C(4) C(9) C(8) 0.4(8) . . . . yes C(5) C(4) C(9) C(10) -179.4(5) . . . . yes C(5) C(6) C(7) C(8) -0.5(9) . . . . yes C(6) C(5) C(4) C(9) -2.1(9) . . . . yes C(6) C(7) C(8) C(9) -1.2(9) . . . . yes C(7) C(8) C(9) C(10) -179.0(5) . . . . yes C(8) C(9) C(10) C(11) 179.8(5) . . . . yes C(12) S(3) C(13) C(14) -179.7(5) . . . . yes C(12) S(3) C(13) C(22) 0.4(5) . . . . yes C(12) S(4) C(22) C(13) -2.3(5) . . . . yes C(12) S(4) C(22) C(21) 178.7(5) . . . . yes C(12) C(12) S(3) C(13) 177.9(7) . 2_545 2_545 2_545 yes C(12) C(12) S(4) C(22) -178.7(7) . 2_545 2_545 2_545 yes C(13) C(14) C(15) C(16) -178.6(5) . . . . yes C(13) C(14) C(15) C(20) 0.5(9) . . . . yes C(13) C(22) C(21) C(20) 0.0(9) . . . . yes C(14) C(13) C(22) C(21) 0.5(9) . . . . yes C(14) C(15) C(16) C(17) 179.6(5) . . . . yes C(14) C(15) C(20) C(19) -178.7(5) . . . . yes C(14) C(15) C(20) C(21) 0.0(8) . . . . yes C(15) C(14) C(13) C(22) -0.7(9) . . . . yes C(15) C(16) C(17) C(18) -0.5(10) . . . . yes C(15) C(20) C(19) C(18) -1.2(9) . . . . yes C(15) C(20) C(21) C(22) -0.2(8) . . . . yes C(16) C(15) C(20) C(19) 0.4(8) . . . . yes C(16) C(15) C(20) C(21) 179.1(5) . . . . yes C(16) C(17) C(18) C(19) -0.2(9) . . . . yes C(17) C(16) C(15) C(20) 0.4(9) . . . . yes C(17) C(18) C(19) C(20) 1.1(9) . . . . yes C(18) C(19) C(20) C(21) -179.8(5) . . . . yes C(19) C(20) C(21) C(22) 178.5(5) . . . . yes C(19) C(20) C(21) C(22) 178.5(5) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S(1) C(22) 3.538(5) . 1_665 ? S(1) C(13) 3.560(6) . 1_665 ? S(2) C(12) 3.446(6) . 2_545 ? S(2) C(12) 3.531(6) . . ? S(3) C(1) 3.496(6) . 1_545 ? C(3) C(8) 3.552(9) . 1_655 ? C(8) C(15) 3.591(7) . . ? #===END #------------------------------------------------------------------------------ data_3 #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C11 H4 N4 S4 ' _chemical_formula_moiety '?' _chemical_formula_weight 320.42 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 8.65(1) _cell_length_b 9.51(1) _cell_length_c 9.43(1) _cell_angle_alpha 74.06(4) _cell_angle_beta 65.35(5) _cell_angle_gamma 63.74(5) _cell_volume 627(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 5957 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.6 _cell_measurement_temperature 93.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'block' _exptl_crystal_colour 'yellow' _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.300 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.695 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.744 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.528 _exptl_absorpt_correction_T_max 0.800 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 6068 _diffrn_reflns_av_R_equivalents 0.032 _diffrn_reflns_theta_max 27.48 _diffrn_measured_fraction_theta_max 0.9920 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.9920 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2867 _reflns_number_gt 2541 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.1003 _refine_ls_wR_factor_ref 0.3655 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 2842 _refine_ls_number_parameters 163 _refine_ls_goodness_of_fit_ref 1.968 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.15000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0018 _refine_diff_density_max 1.71 _refine_diff_density_min -0.95 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'S' 'S' 0.125 0.123 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S(1) S 0.9298(2) 0.0398(2) 0.2901(2) 0.0184(4) Uani 1.00 d . . . S(2) S 1.1103(2) -0.2517(2) 0.4712(2) 0.0182(4) Uani 1.00 d . . . S(3) S 0.6088(2) -0.0300(2) 0.7500(2) 0.0198(4) Uani 1.00 d . . . S(4) S 0.4390(2) -0.2108(2) 1.0383(2) 0.0178(4) Uani 1.00 d . . . N(1) N 0.9039(9) -0.1466(8) 0.1286(8) 0.034(2) Uani 1.00 d . . . N(2) N 1.0727(9) -0.4249(8) 0.3014(8) 0.032(2) Uani 1.00 d . . . N(3) N 0.5834(9) -0.2054(8) 0.5740(8) 0.032(2) Uani 1.00 d . . . N(4) N 0.4208(9) -0.3745(8) 0.8458(8) 0.032(2) Uani 1.00 d . . . C(1) C 1.0071(8) -0.0444(7) 0.4513(7) 0.016(1) Uani 1.00 d . . . C(2) C 0.9597(8) -0.1388(7) 0.2435(7) 0.018(1) Uani 1.00 d . . . C(3) C 1.0462(8) -0.2780(7) 0.3301(7) 0.018(1) Uani 1.00 d . . . C(4) C 0.9250(10) -0.2935(9) 0.1054(8) 0.027(2) Uani 1.00 d . . . C(5) C 1.0091(10) -0.4305(8) 0.1904(8) 0.027(2) Uani 1.00 d . . . C(6) C 0.5091(8) -0.0499(7) 0.9557(6) 0.015(1) Uani 1.00 d . . . C(7) C 0.5511(8) -0.1730(7) 0.7212(7) 0.018(1) Uani 1.00 d . . . C(8) C 0.4700(8) -0.2579(7) 0.8575(7) 0.018(1) Uani 1.00 d . . . C(9) C 0.5333(9) -0.3214(9) 0.5640(9) 0.029(2) Uani 1.00 d . . . C(10) C 0.4516(10) -0.4046(8) 0.6982(9) 0.027(2) Uani 1.00 d . . . H(1) H 0.8873 -0.2994 0.0241 0.0308 Uiso 1.00 calc . . . H(2) H 1.0291 -0.5358 0.1714 0.0340 Uiso 1.00 calc . . . H(3) H 0.5565 -0.3428 0.4585 0.0379 Uiso 1.00 calc . . . H(4) H 0.4150 -0.4831 0.6893 0.0344 Uiso 1.00 calc . . . 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) 0.0235(9) 0.0145(8) 0.0176(8) -0.0035(6) -0.0109(6) -0.0023(6) S(2) 0.0239(9) 0.0130(8) 0.0194(8) -0.0040(6) -0.0120(6) -0.0023(6) S(3) 0.0246(9) 0.0257(9) 0.0135(8) -0.0155(7) -0.0033(6) -0.0036(6) S(4) 0.0230(9) 0.0161(9) 0.0174(8) -0.0106(7) -0.0063(6) -0.0018(6) N(1) 0.030(4) 0.037(4) 0.031(3) -0.008(3) -0.010(3) -0.009(3) N(2) 0.033(4) 0.030(3) 0.031(3) -0.011(3) -0.005(3) -0.011(3) N(3) 0.023(3) 0.040(4) 0.028(3) -0.001(3) -0.008(3) -0.015(3) N(4) 0.026(3) 0.025(3) 0.046(4) -0.004(3) -0.018(3) -0.007(3) C(1) 0.015(3) 0.013(3) 0.016(3) -0.002(2) -0.005(2) -0.002(2) C(2) 0.011(3) 0.019(3) 0.022(3) -0.004(2) -0.002(2) -0.007(2) C(3) 0.018(3) 0.017(3) 0.021(3) -0.006(2) -0.008(2) -0.005(2) C(4) 0.030(4) 0.032(4) 0.025(3) -0.009(3) -0.009(3) -0.015(3) C(5) 0.030(4) 0.028(4) 0.029(3) -0.012(3) -0.008(3) -0.012(3) C(6) 0.018(3) 0.018(3) 0.010(2) -0.007(2) -0.006(2) -0.002(2) C(7) 0.012(3) 0.017(3) 0.022(3) -0.001(2) -0.006(2) -0.007(2) C(8) 0.014(3) 0.018(3) 0.021(3) -0.001(2) -0.005(2) -0.009(2) C(9) 0.023(3) 0.029(4) 0.039(4) 0.002(3) -0.017(3) -0.018(3) C(10) 0.030(4) 0.019(3) 0.042(4) -0.002(3) -0.021(3) -0.015(3) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR97 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 S(1) C(1) 1.761(6) . . yes S(1) C(2) 1.752(6) . . yes S(2) C(1) 1.760(6) . . yes S(2) C(3) 1.749(6) . . yes S(3) C(6) 1.756(6) . . yes S(3) C(7) 1.757(6) . . yes S(4) C(6) 1.757(6) . . yes S(4) C(8) 1.763(6) . . yes N(1) C(2) 1.386(9) . . yes N(1) C(4) 1.394(9) . . yes N(2) C(3) 1.396(9) . . yes N(2) C(5) 1.392(9) . . yes N(3) C(7) 1.391(9) . . yes N(3) C(9) 1.388(10) . . yes N(4) C(8) 1.394(9) . . yes N(4) C(10) 1.390(10) . . yes C(1) C(1) 1.35(1) . 2_756 yes C(2) C(3) 1.420(9) . . yes C(4) C(5) 1.39(1) . . yes C(6) C(6) 1.35(1) . 2_657 yes C(7) C(8) 1.405(9) . . yes C(9) C(10) 1.39(1) . . yes #------------------------------------------------------------------------------ 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 C(1) S(1) C(2) 95.6(3) . . . yes C(1) S(2) C(3) 95.6(3) . . . yes C(6) S(3) C(7) 95.4(3) . . . yes C(6) S(4) C(8) 95.0(3) . . . yes C(2) N(1) C(4) 118.7(6) . . . yes C(3) N(2) C(5) 118.7(6) . . . yes C(7) N(3) C(9) 119.1(7) . . . yes C(8) N(4) C(10) 119.3(7) . . . yes S(1) C(1) S(2) 115.1(3) . . . yes S(1) C(1) C(1) 122.1(6) . . 2_756 yes S(2) C(1) C(1) 122.8(6) . . 2_756 yes S(1) C(2) N(1) 122.8(5) . . . yes S(1) C(2) C(3) 116.2(4) . . . yes N(1) C(2) C(3) 121.0(6) . . . yes S(2) C(3) N(2) 123.9(5) . . . yes S(2) C(3) C(2) 116.4(4) . . . yes N(2) C(3) C(2) 119.7(6) . . . yes N(1) C(4) C(5) 120.5(6) . . . yes N(2) C(5) C(4) 121.3(6) . . . yes S(3) C(6) S(4) 115.6(3) . . . yes S(3) C(6) C(6) 122.1(6) . . 2_657 yes S(4) C(6) C(6) 122.3(6) . . 2_657 yes S(3) C(7) N(3) 123.7(5) . . . yes S(3) C(7) C(8) 116.3(4) . . . yes N(3) C(7) C(8) 120.1(6) . . . yes S(4) C(8) N(4) 123.1(5) . . . yes S(4) C(8) C(7) 116.6(5) . . . yes N(4) C(8) C(7) 120.2(6) . . . yes N(3) C(9) C(10) 121.1(6) . . . yes N(4) C(10) C(9) 120.2(6) . . . yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S(1) C(1) S(2) C(3) -10.3(4) . . . . yes S(1) C(1) C(1) S(1) -180.0 . . 2_756 2_756 yes S(1) C(1) C(1) S(2) 2(1) . . 2_756 2_756 yes S(1) C(2) N(1) C(4) -176.7(5) . . . . yes S(1) C(2) C(3) S(2) 0.1(7) . . . . yes S(1) C(2) C(3) N(2) 179.1(4) . . . . yes S(2) C(1) S(1) C(2) 10.4(4) . . . . yes S(2) C(1) C(1) S(2) 180.0 . . 2_756 2_756 yes S(2) C(3) N(2) C(5) 177.4(5) . . . . yes S(2) C(3) C(2) N(1) 179.8(4) . . . . yes S(3) C(6) S(4) C(8) -10.2(4) . . . . yes S(3) C(6) C(6) S(3) 180.0 . . 2_657 2_657 yes S(3) C(6) C(6) S(4) 1(1) . . 2_657 2_657 yes S(3) C(7) N(3) C(9) 179.7(5) . . . . yes S(3) C(7) C(8) S(4) -0.5(7) . . . . yes S(3) C(7) C(8) N(4) -179.6(4) . . . . yes S(4) C(6) S(3) C(7) 10.1(4) . . . . yes S(4) C(6) C(6) S(4) 180.0 . . 2_657 2_657 yes S(4) C(8) N(4) C(10) -179.5(5) . . . . yes S(4) C(8) C(7) N(3) 178.8(4) . . . . yes N(1) C(2) S(1) C(1) 174.0(5) . . . . yes N(1) C(2) C(3) N(2) -1.2(10) . . . . yes N(1) C(4) C(5) N(2) 0(1) . . . . yes N(2) C(3) S(2) C(1) -172.9(6) . . . . yes N(3) C(7) S(3) C(6) 175.1(6) . . . . yes N(3) C(7) C(8) N(4) -0.3(10) . . . . yes N(3) C(9) C(10) N(4) 0(1) . . . . yes N(4) C(8) S(4) C(6) -174.6(5) . . . . yes C(1) S(1) C(2) C(3) -6.2(5) . . . . yes C(1) S(2) C(3) C(2) 6.1(5) . . . . yes C(1) C(1) S(1) C(2) 171.6(7) . 2_756 2_756 2_756 yes C(1) C(1) S(2) C(3) -171.6(7) . 2_756 2_756 2_756 yes C(2) N(1) C(4) C(5) -3(1) . . . . yes C(2) C(3) N(2) C(5) -1.6(10) . . . . yes C(3) N(2) C(5) C(4) 1(1) . . . . yes C(3) C(2) N(1) C(4) 3.6(10) . . . . yes C(6) S(3) C(7) C(8) -5.7(5) . . . . yes C(6) S(4) C(8) C(7) 6.4(5) . . . . yes C(6) C(6) S(3) C(7) 171.2(7) . 2_657 2_657 2_657 yes C(6) C(6) S(4) C(8) -171.0(7) . 2_657 2_657 2_657 yes C(7) N(3) C(9) C(10) 0(1) . . . . yes C(7) C(8) N(4) C(10) 0(1) . . . . yes C(8) N(4) C(10) C(9) 1(1) . . . . yes C(8) C(7) N(3) C(9) 0.4(10) . . . . yes C(8) C(7) N(3) C(9) 0.4(10) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S(1) C(10) 3.565(7) . 2_656 ? S(3) C(1) 3.350(7) . 2_756 ? S(3) C(1) 3.394(7) . . ? S(4) C(3) 3.561(7) . 1_456 ? S(4) N(4) 3.566(7) . 2_647 ? S(4) C(2) 3.595(8) . 1_456 ? N(1) C(6) 3.540(10) . 2_656 ? N(2) N(2) 3.52(1) . 2_746 ? N(3) C(3) 3.54(1) . . ? N(4) N(4) 3.55(1) . 2_647 ? #===END #------------------------------------------------------------------------------ data_4 #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C16 H8 N4 S4 ' _chemical_formula_moiety '?' _chemical_formula_weight 384.51 _chemical_melting_point ? #------------------------------------------------------------------------------ # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z _cell_length_a 4.88(1) _cell_length_b 5.75(1) _cell_length_c 29.07(5) _cell_angle_alpha 94.01(9) _cell_angle_beta 90.78(8) _cell_angle_gamma 105.03(9) _cell_volume 785(10) _cell_formula_units_Z 2 _cell_measurement_reflns_used 7263 _cell_measurement_theta_min 3.5 _cell_measurement_theta_max 27.7 _cell_measurement_temperature 93.2 #------------------------------------------------------------------------------ _exptl_crystal_description 'platelet' _exptl_crystal_colour 'palered' _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_min 0.070 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.625 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.610 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(Higashi, 1995)' _exptl_absorpt_correction_T_min 0.335 _exptl_absorpt_correction_T_max 0.958 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 7365 _diffrn_reflns_av_R_equivalents 0.085 _diffrn_reflns_theta_max 27.49 _diffrn_measured_fraction_theta_max 0.9994 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.9994 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 0.0 sigma(F^2^). The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3580 _reflns_number_gt 1234 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0949 _refine_ls_wR_factor_ref 0.2139 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 3558 _refine_ls_number_parameters 235 _refine_ls_goodness_of_fit_ref 0.810 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^) + (0.05000(Max(Fo^2^,0) + 2Fc^2^)/3)^2^]' _refine_ls_shift/su_max 0.0026 _refine_diff_density_max 1.22 _refine_diff_density_min -1.49 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details ? _refine_ls_abs_structure_Flack ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.003 0.002 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'H' 'H' 0.000 0.000 ;International Tables for Crystallography (1992, Vol. C, Table 6.1.1.2) ; 'N' 'N' 0.006 0.003 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; 'S' 'S' 0.125 0.123 ;International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1) ; #------------------------------------------------------------------------------ # ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S(1) S -0.1330(6) 0.7500(5) -0.46380(8) 0.0176(7) Uani 1.00 d . . . S(2) S -0.4592(6) 0.2423(5) -0.44998(8) 0.0160(7) Uani 1.00 d . . . S(3) S 0.3519(6) 0.7216(5) -0.03592(9) 0.0169(7) Uani 1.00 d . . . S(4) S 0.0229(5) 0.2038(5) -0.05028(8) 0.0145(7) Uani 1.00 d . . . N(1) N 0.223(2) 0.727(1) -0.3956(3) 0.014(2) Uani 1.00 d . . . N(2) N -0.082(2) 0.235(2) -0.3828(3) 0.012(2) Uani 1.00 d . . . N(3) N 0.682(2) 0.645(2) -0.1046(3) 0.012(2) Uani 1.00 d . . . N(4) N 0.374(2) 0.146(1) -0.1182(3) 0.012(2) Uani 1.00 d . . . C(1) C -0.418(2) 0.499(2) -0.4823(3) 0.017(3) Uani 1.00 d . . . C(2) C -0.001(2) 0.608(2) -0.4195(3) 0.016(3) Uani 1.00 d . . . C(3) C -0.161(2) 0.364(2) -0.4137(3) 0.014(3) Uani 1.00 d . . . C(4) C 0.308(2) 0.598(2) -0.3616(3) 0.012(3) Uani 1.00 d . . . C(5) C 0.549(2) 0.709(2) -0.3340(3) 0.017(3) Uani 1.00 d . . . C(6) C 0.639(2) 0.586(2) -0.3004(3) 0.020(3) Uani 1.00 d . . . C(7) C 0.492(2) 0.341(2) -0.2951(3) 0.022(3) Uani 1.00 d . . . C(8) C 0.254(2) 0.231(2) -0.3216(3) 0.016(3) Uani 1.00 d . . . C(9) C 0.154(2) 0.358(2) -0.3560(3) 0.014(3) Uani 1.00 d . . . C(10) C 0.080(2) 0.484(2) -0.0178(3) 0.013(3) Uani 1.00 d . . . C(11) C 0.466(2) 0.542(2) -0.0799(3) 0.015(3) Uani 1.00 d . . . C(12) C 0.310(2) 0.296(2) -0.0865(3) 0.014(3) Uani 1.00 d . . . C(13) C 0.756(2) 0.493(2) -0.1377(3) 0.012(3) Uani 1.00 d . . . C(14) C 0.992(2) 0.582(2) -0.1648(3) 0.015(3) Uani 1.00 d . . . C(15) C 1.072(2) 0.436(2) -0.1987(3) 0.017(3) Uani 1.00 d . . . C(16) C 0.923(2) 0.184(2) -0.2052(3) 0.018(3) Uani 1.00 d . . . C(17) C 0.690(2) 0.091(2) -0.1789(3) 0.013(3) Uani 1.00 d . . . C(18) C 0.604(2) 0.246(2) -0.1446(3) 0.016(3) Uani 1.00 d . . . H(1) H 0.6507 0.8691 -0.3383 0.0189 Uiso 1.00 calc . . . H(2) H 0.8032 0.6610 -0.2811 0.0197 Uiso 1.00 calc . . . H(3) H 0.5568 0.2528 -0.2732 0.0265 Uiso 1.00 calc . . . H(4) H 0.1494 0.0640 -0.3168 0.0173 Uiso 1.00 calc . . . H(5) H 1.0934 0.7500 -0.1590 0.0148 Uiso 1.00 calc . . . H(6) H 1.2259 0.5012 -0.2175 0.0211 Uiso 1.00 calc . . . H(7) H 0.9839 0.0815 -0.2274 0.0199 Uiso 1.00 calc . . . H(8) H 0.5867 -0.0781 -0.1819 0.0172 Uiso 1.00 calc . . . 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) 0.021(2) 0.015(2) 0.017(1) 0.005(1) -0.003(1) 0.004(1) S(2) 0.018(2) 0.015(2) 0.017(1) 0.008(1) -0.002(1) 0.003(1) S(3) 0.016(2) 0.012(1) 0.023(1) 0.005(1) 0.004(1) -0.003(1) S(4) 0.013(1) 0.010(1) 0.020(1) 0.004(1) 0.002(1) -0.002(1) N(1) 0.017(5) 0.005(5) 0.022(4) 0.006(4) 0.000(4) -0.002(3) N(2) 0.011(4) 0.014(5) 0.014(4) 0.009(4) -0.001(3) -0.004(3) N(3) 0.003(4) 0.011(5) 0.022(4) 0.006(4) -0.005(3) -0.001(3) N(4) 0.010(5) 0.002(4) 0.022(4) 0.001(4) -0.005(3) -0.001(3) C(1) 0.019(6) 0.018(6) 0.020(5) 0.016(5) -0.001(4) 0.002(4) C(2) 0.019(6) 0.016(6) 0.019(5) 0.015(5) 0.004(4) 0.006(4) C(3) 0.016(5) 0.024(6) 0.003(4) 0.010(5) 0.001(4) -0.004(4) C(4) 0.007(5) 0.012(6) 0.020(5) 0.009(4) 0.000(4) 0.002(4) C(5) 0.030(6) 0.014(6) 0.013(5) 0.014(5) 0.002(4) -0.001(4) C(6) 0.001(5) 0.017(6) 0.039(6) -0.001(4) -0.005(4) 0.002(5) C(7) 0.042(7) 0.024(7) 0.008(5) 0.020(6) 0.010(5) 0.005(5) C(8) 0.024(6) 0.019(6) 0.007(5) 0.012(5) -0.007(4) -0.001(4) C(9) 0.030(6) 0.004(5) 0.011(5) 0.011(5) 0.004(4) -0.002(4) C(10) 0.018(5) 0.013(6) 0.010(4) 0.007(4) -0.004(4) 0.003(4) C(11) 0.025(6) 0.011(6) 0.011(5) 0.012(5) 0.000(4) -0.002(4) C(12) 0.005(5) 0.018(6) 0.019(5) 0.003(4) -0.001(4) 0.004(4) C(13) 0.014(5) 0.012(6) 0.013(5) 0.008(4) 0.001(4) 0.001(4) C(14) 0.010(5) 0.012(6) 0.024(5) 0.007(4) -0.005(4) 0.003(4) C(15) 0.012(5) 0.024(6) 0.016(5) 0.006(5) 0.003(4) 0.001(4) C(16) 0.015(6) 0.014(6) 0.025(6) 0.008(5) -0.002(4) -0.004(5) C(17) 0.014(5) 0.005(5) 0.015(5) -0.003(4) -0.007(4) -0.001(4) C(18) 0.015(6) 0.004(5) 0.030(6) 0.005(4) -0.005(4) 0.004(4) #------------------------------------------------------------------------------ _computing_data_collection 'PROCESS-AUTO' _computing_cell_refinement 'PROCESS-AUTO' _computing_data_reduction 'teXsan Ver. 1.11' _computing_structure_solution SIR97 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.11' _computing_molecular_graphics ? #------------------------------------------------------------------------------ _geom_special_details ; ? ; 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 S(1) C(1) 1.77(1) . . yes S(1) C(2) 1.772(10) . . yes S(2) C(1) 1.775(10) . . yes S(2) C(3) 1.746(10) . . yes S(3) C(10) 1.756(9) . . yes S(3) C(11) 1.77(1) . . yes S(4) C(10) 1.76(1) . . yes S(4) C(12) 1.758(9) . . yes N(1) C(2) 1.29(1) . . yes N(1) C(4) 1.40(1) . . yes N(2) C(3) 1.32(1) . . yes N(2) C(9) 1.38(1) . . yes N(3) C(11) 1.31(1) . . yes N(3) C(13) 1.37(1) . . yes N(4) C(12) 1.31(1) . . yes N(4) C(18) 1.39(1) . . yes C(1) C(1) 1.30(2) . 2_464 yes C(2) C(3) 1.44(1) . . yes C(4) C(5) 1.40(1) . . yes C(4) C(9) 1.41(1) . . yes C(5) C(6) 1.38(1) . . yes C(6) C(7) 1.42(1) . . yes C(7) C(8) 1.36(1) . . yes C(8) C(9) 1.44(1) . . yes C(10) C(10) 1.34(2) . 2_565 yes C(11) C(12) 1.42(1) . . yes C(13) C(14) 1.41(1) . . yes C(13) C(18) 1.42(1) . . yes C(14) C(15) 1.37(1) . . yes C(15) C(16) 1.44(1) . . yes C(16) C(17) 1.39(1) . . yes C(17) C(18) 1.43(1) . . yes #------------------------------------------------------------------------------ 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 C(1) S(1) C(2) 96.1(5) . . . yes C(1) S(2) C(3) 95.6(5) . . . yes C(10) S(3) C(11) 95.0(5) . . . yes C(10) S(4) C(12) 95.6(5) . . . yes C(2) N(1) C(4) 114.2(8) . . . yes C(3) N(2) C(9) 114.2(8) . . . yes C(11) N(3) C(13) 114.7(8) . . . yes C(12) N(4) C(18) 115.0(8) . . . yes S(1) C(1) S(2) 115.5(5) . . . yes S(1) C(1) C(1) 122(1) . . 2_464 yes S(2) C(1) C(1) 122(1) . . 2_464 yes S(1) C(2) N(1) 119.0(8) . . . yes S(1) C(2) C(3) 115.0(7) . . . yes N(1) C(2) C(3) 126.0(9) . . . yes S(2) C(3) N(2) 121.0(8) . . . yes S(2) C(3) C(2) 117.6(7) . . . yes N(2) C(3) C(2) 121.4(9) . . . yes N(1) C(4) C(5) 118.9(8) . . . yes N(1) C(4) C(9) 120.1(8) . . . yes C(5) C(4) C(9) 120.9(8) . . . yes C(4) C(5) C(6) 120.3(9) . . . yes C(5) C(6) C(7) 119.7(9) . . . yes C(6) C(7) C(8) 120.7(9) . . . yes C(7) C(8) C(9) 120.2(10) . . . yes N(2) C(9) C(4) 124.1(8) . . . yes N(2) C(9) C(8) 117.8(8) . . . yes C(4) C(9) C(8) 118.1(9) . . . yes S(3) C(10) S(4) 116.4(5) . . . yes S(3) C(10) C(10) 121(1) . . 2_565 yes S(4) C(10) C(10) 121.9(10) . . 2_565 yes S(3) C(11) N(3) 118.5(8) . . . yes S(3) C(11) C(12) 116.6(7) . . . yes N(3) C(11) C(12) 124.8(9) . . . yes S(4) C(12) N(4) 121.7(8) . . . yes S(4) C(12) C(11) 116.2(8) . . . yes N(4) C(12) C(11) 122.1(8) . . . yes N(3) C(13) C(14) 119.5(9) . . . yes N(3) C(13) C(18) 121.3(8) . . . yes C(14) C(13) C(18) 119.1(9) . . . yes C(13) C(14) C(15) 121.3(9) . . . yes C(14) C(15) C(16) 119.9(9) . . . yes C(15) C(16) C(17) 120.1(9) . . . yes C(16) C(17) C(18) 119.4(9) . . . yes N(4) C(18) C(13) 122.1(9) . . . yes N(4) C(18) C(17) 117.9(9) . . . yes C(13) C(18) C(17) 120.0(9) . . . yes #------------------------------------------------------------------------------ loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag S(1) C(1) S(2) C(3) -3.0(6) . . . . yes S(1) C(1) C(1) S(1) 180.0 . . 2_464 2_464 yes S(1) C(1) C(1) S(2) -1(1) . . 2_464 2_464 yes S(1) C(2) N(1) C(4) 179.9(7) . . . . yes S(1) C(2) C(3) S(2) -0.2(10) . . . . yes S(1) C(2) C(3) N(2) 178.2(7) . . . . yes S(2) C(1) S(1) C(2) 2.9(6) . . . . yes S(2) C(1) C(1) S(2) 180.0 . . 2_464 2_464 yes S(2) C(3) N(2) C(9) -178.7(7) . . . . yes S(2) C(3) C(2) N(1) 179.4(8) . . . . yes S(3) C(10) S(4) C(12) 4.6(6) . . . . yes S(3) C(10) C(10) S(3) -180.0 . . 2_565 2_565 yes S(3) C(10) C(10) S(4) -2(1) . . 2_565 2_565 yes S(3) C(11) N(3) C(13) 179.9(7) . . . . yes S(3) C(11) C(12) S(4) 0(1) . . . . yes S(3) C(11) C(12) N(4) 179.7(8) . . . . yes S(4) C(10) S(3) C(11) -4.5(6) . . . . yes S(4) C(10) C(10) S(4) 180.0 . . 2_565 2_565 yes S(4) C(12) N(4) C(18) 179.0(7) . . . . yes S(4) C(12) C(11) N(3) -177.7(8) . . . . yes N(1) C(2) S(1) C(1) 178.7(8) . . . . yes N(1) C(2) C(3) N(2) -2(1) . . . . yes N(1) C(4) C(5) C(6) -179.5(9) . . . . yes N(1) C(4) C(9) N(2) 0(1) . . . . yes N(1) C(4) C(9) C(8) 178.2(9) . . . . yes N(2) C(3) S(2) C(1) -176.5(8) . . . . yes N(2) C(9) C(4) C(5) -178.5(9) . . . . yes N(2) C(9) C(8) C(7) 178.1(9) . . . . yes N(3) C(11) S(3) C(10) -179.4(8) . . . . yes N(3) C(11) C(12) N(4) 1(1) . . . . yes N(3) C(13) C(14) C(15) -179.4(9) . . . . yes N(3) C(13) C(18) N(4) 0(1) . . . . yes N(3) C(13) C(18) C(17) -178.8(9) . . . . yes N(4) C(12) S(4) C(10) 177.7(8) . . . . yes N(4) C(18) C(13) C(14) 178.2(8) . . . . yes N(4) C(18) C(17) C(16) -178.6(9) . . . . yes C(1) S(1) C(2) C(3) -1.6(8) . . . . yes C(1) S(2) C(3) C(2) 1.9(8) . . . . yes C(1) C(1) S(1) C(2) 175(1) . 2_464 2_464 2_464 yes C(1) C(1) S(2) C(3) -175(1) . 2_464 2_464 2_464 yes C(2) N(1) C(4) C(5) 179.5(9) . . . . yes C(2) N(1) C(4) C(9) 0(1) . . . . yes C(2) C(3) N(2) C(9) 2(1) . . . . yes C(3) N(2) C(9) C(4) -2(1) . . . . yes C(3) N(2) C(9) C(8) -179.9(9) . . . . yes C(3) C(2) N(1) C(4) 0(1) . . . . yes C(4) C(5) C(6) C(7) 2(1) . . . . yes C(4) C(9) C(8) C(7) 0(1) . . . . yes C(5) C(4) C(9) C(8) 0(1) . . . . yes C(5) C(6) C(7) C(8) -2(1) . . . . yes C(6) C(5) C(4) C(9) 0(1) . . . . yes C(6) C(7) C(8) C(9) 1(1) . . . . yes C(10) S(3) C(11) C(12) 2.5(8) . . . . yes C(10) S(4) C(12) C(11) -2.8(8) . . . . yes C(10) C(10) S(3) C(11) -177(1) . 2_565 2_565 2_565 yes C(10) C(10) S(4) C(12) 177(1) . 2_565 2_565 2_565 yes C(11) N(3) C(13) C(14) -177.1(9) . . . . yes C(11) N(3) C(13) C(18) 1(1) . . . . yes C(11) C(12) N(4) C(18) 0(1) . . . . yes C(12) N(4) C(18) C(13) 0(1) . . . . yes C(12) N(4) C(18) C(17) 178.3(9) . . . . yes C(12) C(11) N(3) C(13) -2(1) . . . . yes C(13) C(14) C(15) C(16) -3(1) . . . . yes C(13) C(18) C(17) C(16) 0(1) . . . . yes C(14) C(13) C(18) C(17) 0(1) . . . . yes C(14) C(15) C(16) C(17) 3(1) . . . . yes C(15) C(14) C(13) C(18) 2(1) . . . . yes C(15) C(16) C(17) C(18) -1(1) . . . . yes C(15) C(16) C(17) C(18) -1(1) . . . . yes #------------------------------------------------------------------------------ loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag S(1) N(2) 3.479(9) . 1_565 ? S(1) S(2) 3.593(5) . 1_565 ? S(2) C(9) 3.465(10) . 1_455 ? S(2) N(1) 3.470(8) . 1_445 ? S(2) C(4) 3.55(1) . 1_455 ? S(3) N(4) 3.517(8) . 1_565 ? S(3) S(4) 3.592(4) . 1_565 ? S(4) C(18) 3.46(1) . 1_455 ? S(4) N(3) 3.471(9) . 1_445 ? S(4) C(13) 3.544(10) . 1_455 ? N(1) C(8) 3.46(1) . 1_565 ? N(1) C(1) 3.46(1) . 1_655 ? N(2) C(7) 3.43(1) . 1_455 ? N(2) C(5) 3.50(1) . 1_445 ? N(2) C(6) 3.53(1) . 1_455 ? N(3) C(17) 3.46(1) . 1_565 ? N(3) C(10) 3.48(1) . 1_655 ? N(4) C(16) 3.39(1) . 1_455 ? N(4) C(14) 3.47(1) . 1_445 ? N(4) C(15) 3.49(1) . 1_455 ? C(1) C(2) 3.57(1) . 1_455 ? C(2) C(5) 3.46(1) . 1_455 ? C(3) C(5) 3.49(1) . 1_455 ? C(3) C(4) 3.53(1) . 1_455 ? C(6) C(9) 3.49(2) . 1_655 ? C(7) C(15) 3.59(1) . 1_455 ? C(10) C(11) 3.58(1) . 1_455 ? C(11) C(14) 3.42(1) . 1_455 ? C(12) C(14) 3.47(1) . 1_455 ? C(12) C(13) 3.54(1) . 1_455 ? C(15) C(18) 3.46(2) . 1_655 ? #===END #------------------------------------------------------------------------------ # END of CIF #------------------------------------------------------------------------------ data_CSD_CIF_BDTOLE02 _audit_creation_date 1995-09-08 _audit_creation_method CSD-ConQuest-V1 _database_code_CSD BDTOLE02 _chemical_formula_sum 'C6 H4 S4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 x,y,z 2 -x,-y,-z _cell_length_a 8.379 _cell_length_b 12.906 _cell_length_c 8.145 _cell_angle_alpha 98.91 _cell_angle_beta 96.62 _cell_angle_gamma 100.44 _cell_formula_units_Z 4 loop_ _atom_type_symbol _atom_type_radius_bond C 0.68 H 0.23 S 1.02 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z S1 S 0.5268(1) 0.8393(1) -0.1136(2) S2 S 0.7540(1) 1.0167(1) 0.1164(2) S3 S 0.6161(2) 0.5027(1) 0.7567(1) S4 S 0.3820(2) 0.3358(1) 0.5134(1) S5 S 0.8982(2) 0.5480(1) 0.2294(1) S6 S 0.9447(1) 0.3386(1) 0.0603(2) S7 S 0.0319(1) 0.8337(1) 0.4464(1) S8 S 0.2340(1) 1.0377(1) 0.4059(2) C1 C 0.7233(5) 0.8224(4) -0.0511(6) C2 C 0.8241(5) 0.9008(4) 0.0514(5) C3 C 0.5576(4) 0.9699(3) 0.0009(4) C4 C 0.5436(5) 0.3834(3) 0.8190(5) C5 C 0.4404(5) 0.3085(3) 0.7116(5) C6 C 0.4996(4) 0.4669(3) 0.5553(4) C7 C 0.8502(6) 0.4398(4) 0.3281(6) C8 C 0.8689(5) 0.3465(4) 0.2513(6) C9 C 0.9678(4) 0.4769(3) 0.0598(4) C10 C 0.2174(6) 0.8303(4) 0.3756(6) C11 C 0.3065(6) 0.9211(4) 0.3571(6) C12 C 0.0550(4) 0.9735(3) 0.4702(4) H1 H 0.75740 0.75700 -0.09040 H2 H 0.93430 0.89490 0.08960 H3 H 0.57850 0.37190 0.93000 H4 H 0.39790 0.24070 0.74110 H5 H 0.81140 0.44730 0.43490 H6 H 0.84130 0.28340 0.29940 H7 H 0.25440 0.76420 0.35070 H8 H 0.41020 0.92320 0.31710 C3A* C 0.4424(4) 1.0301(3) -0.0009(4) S1A* S 0.4732(1) 1.1607(1) 0.1136(2) S2A* S 0.2460(1) 0.9833(1) -0.1164(2) C1A* C 0.2767(5) 1.1776(4) 0.0511(6) C2A* C 0.1759(5) 1.0992(4) -0.0514(5) H1A* H 0.24260 1.24300 0.09040 H2A* H 0.06570 1.10510 -0.08960 C6A* C 0.5004(4) 0.5331(3) 0.4447(4) S3A* S 0.3839(2) 0.4973(1) 0.2433(1) S4A* S 0.6180(2) 0.6642(1) 0.4866(1) C4A* C 0.4564(5) 0.6166(3) 0.1810(5) C5A* C 0.5596(5) 0.6915(3) 0.2884(5) H3A* H 0.42150 0.62810 0.07000 H4A* H 0.60210 0.75930 0.25890 C9A* C 1.0322(4) 0.5231(3) -0.0598(4) S5A* S 1.1018(2) 0.4520(1) -0.2294(1) S6A* S 1.0553(1) 0.6614(1) -0.0603(2) C7A* C 1.1498(6) 0.5602(4) -0.3281(6) C8A* C 1.1311(5) 0.6535(4) -0.2513(6) H5A* H 1.18860 0.55270 -0.43490 H6A* H 1.15870 0.71660 -0.29940 C12A* C -0.0550(4) 1.0265(3) 0.5298(4) S7A* S -0.0319(1) 1.1663(1) 0.5536(1) S8A* S -0.2340(1) 0.9623(1) 0.5941(2) C10A* C -0.2174(6) 1.1697(4) 0.6244(6) C11A* C -0.3065(6) 1.0789(4) 0.6429(6) H7A* H -0.25440 1.23580 0.64930 H8A* H -0.41020 1.07680 0.68290