#Supplementary Material (ESI) for Journal of Materials Chemistry #This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Takehiko Mori' _publ_contact_author_email MORI.T.AE@M.TITECH.AC.JP _publ_section_title ; Stabilization of Organic Field-Effect Transistors in Hexamethylenetetrathiafulvalene Derivatives Substituted by Bulky Alkyl Groups ; loop_ _publ_author_name 'Takehiko Mori' 'Yoshimasa Bando' 'Jun-ichi Inoue' 'Masato Kanno' 'Takashi Shirahata' 'Hiroshi Wada' # Attachment '1c1d1e.cif' #------------------------------------------------------------------------------ data_1c _database_code_depnum_ccdc_archive 'CCDC 727313' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C20 H28 S4 ' _chemical_formula_moiety 'C20 H28 S4 ' _chemical_formula_weight 396.68 _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 6.513(1) _cell_length_b 13.459(2) _cell_length_c 6.114(3) _cell_angle_alpha 95.93(3) _cell_angle_beta 106.22(2) _cell_angle_gamma 85.30(1) _cell_volume 511.1(2) _cell_formula_units_Z 1 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 0.5 _cell_measurement_theta_max 15.0 _cell_measurement_temperature 293.2 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.289 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.465 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.932 _exptl_absorpt_correction_T_max 0.999 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 3237 _diffrn_reflns_av_R_equivalents 0.018 _diffrn_reflns_theta_max 29.99 _diffrn_measured_fraction_theta_max 1.0926 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 1.0926 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.17 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 4.1 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^ > 4.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2867 _reflns_number_gt 1946 _reflns_threshold_expression F^2^>4.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0347 _refine_ls_wR_factor_ref 0.1012 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1946 _refine_ls_number_parameters 109 _refine_ls_goodness_of_fit_ref 1.428 _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 0.0005 _refine_diff_density_max 0.24 _refine_diff_density_min -0.17 _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 S1 S 0.67479(8) 0.59968(4) 0.36202(10) 0.0429(2) Uani 1.00 d . . . S2 S 0.22406(8) 0.53813(4) 0.21367(9) 0.0401(2) Uani 1.00 d . . . C1 C 0.4796(3) 0.5282(1) 0.4106(3) 0.0333(5) Uani 1.00 d . . . C2 C 0.5010(3) 0.6507(2) 0.1248(4) 0.0376(5) Uani 1.00 d . . . C3 C 0.2991(3) 0.6228(1) 0.0573(4) 0.0369(5) Uani 1.00 d . . . C4 C 0.5402(3) 0.7278(2) -0.0150(4) 0.0491(7) Uani 1.00 d . . . C5 C 0.3307(3) 0.7319(2) -0.2135(4) 0.0420(6) Uani 1.00 d . . . C6 C 0.1654(4) 0.6746(2) -0.1417(4) 0.0496(6) Uani 1.00 d . . . C7 C 0.2512(4) 0.8362(2) -0.2930(4) 0.0455(6) Uani 1.00 d . . . C8 C 0.4252(5) 0.8809(2) -0.3697(6) 0.075(1) Uani 1.00 d . . . C9 C 0.1953(6) 0.9066(2) -0.1050(6) 0.081(1) Uani 1.00 d . . . C10 C 0.0518(5) 0.8269(2) -0.4959(6) 0.0729(9) Uani 1.00 d . . . H1 H 0.5617 0.7910 0.0714 0.0592 Uiso 1.00 calc . . . H2 H 0.6613 0.7085 -0.0708 0.0592 Uiso 1.00 calc . . . H3 H 0.3610 0.6928 -0.3414 0.0508 Uiso 1.00 calc . . . H4 H 0.0960 0.6283 -0.2611 0.0603 Uiso 1.00 calc . . . H5 H 0.0613 0.7203 -0.0977 0.0603 Uiso 1.00 calc . . . H6 H 0.5506 0.8869 -0.2459 0.0900 Uiso 1.00 calc . . . H7 H 0.4585 0.8377 -0.4913 0.0900 Uiso 1.00 calc . . . H8 H 0.3764 0.9446 -0.4228 0.0900 Uiso 1.00 calc . . . H9 H 0.3183 0.9137 0.0223 0.0965 Uiso 1.00 calc . . . H10 H 0.1472 0.9704 -0.1597 0.0965 Uiso 1.00 calc . . . H11 H 0.0848 0.8802 -0.0577 0.0965 Uiso 1.00 calc . . . H12 H 0.0036 0.8903 -0.5495 0.0866 Uiso 1.00 calc . . . H13 H 0.0871 0.7835 -0.6168 0.0866 Uiso 1.00 calc . . . H14 H -0.0576 0.7986 -0.4517 0.0866 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 S1 0.0280(3) 0.0575(4) 0.0420(3) -0.0103(2) 0.0012(2) 0.0157(3) S2 0.0290(3) 0.0503(3) 0.0393(3) -0.0107(2) -0.0001(2) 0.0153(3) C1 0.0282(9) 0.038(1) 0.032(1) -0.0044(8) 0.0042(8) 0.0037(8) C2 0.0331(10) 0.040(1) 0.040(1) -0.0040(8) 0.0076(9) 0.0105(9) C3 0.0326(10) 0.039(1) 0.038(1) -0.0055(8) 0.0047(9) 0.0113(9) C4 0.039(1) 0.052(1) 0.058(2) -0.0097(10) 0.007(1) 0.021(1) C5 0.047(1) 0.038(1) 0.043(1) -0.0031(9) 0.0125(10) 0.0095(10) C6 0.039(1) 0.051(1) 0.056(1) -0.0084(10) -0.003(1) 0.026(1) C7 0.060(1) 0.035(1) 0.044(1) -0.0004(10) 0.015(1) 0.0105(10) C8 0.089(2) 0.064(2) 0.080(2) -0.016(2) 0.026(2) 0.029(2) C9 0.109(3) 0.053(2) 0.083(2) 0.012(2) 0.034(2) 0.000(2) C10 0.080(2) 0.065(2) 0.068(2) -0.001(1) 0.001(2) 0.032(2) #------------------------------------------------------------------------------ _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SHELXS86 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _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 S1 C1 1.761(2) . . yes S1 C2 1.737(2) . . yes S2 C1 1.765(2) . . yes S2 C3 1.740(2) . . yes C1 C1 1.348(4) . 2_666 yes C2 C3 1.337(3) . . yes C2 C4 1.490(3) . . yes C3 C6 1.486(3) . . yes C4 C5 1.554(3) . . yes C4 H1 0.953 . . no C4 H2 0.951 . . no C5 C6 1.555(3) . . yes C5 C7 1.535(3) . . yes C5 H3 0.955 . . no C6 H4 0.945 . . no C6 H5 0.953 . . no C7 C8 1.528(4) . . yes C7 C9 1.518(4) . . yes C7 C10 1.529(4) . . yes C8 H6 0.948 . . no C8 H7 0.958 . . no C8 H8 0.947 . . no C9 H9 0.951 . . no C9 H10 0.951 . . no C9 H11 0.953 . . no C10 H12 0.944 . . no C10 H13 0.961 . . no C10 H14 0.948 . . 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 C1 S1 C2 94.16(9) . 1_555 1_555 yes C1 S2 C3 94.02(9) . 1_555 1_555 yes S1 C1 S2 115.4(1) . 1_555 1_555 yes S1 C1 C1 122.4(2) . 1_555 2_666 yes S2 C1 C1 122.2(2) . 1_555 2_666 yes S1 C2 C3 118.2(2) . 1_555 1_555 yes S1 C2 C4 129.0(2) . 1_555 1_555 yes C3 C2 C4 112.6(2) . 1_555 1_555 yes S2 C3 C2 118.2(2) . 1_555 1_555 yes S2 C3 C6 128.9(2) . 1_555 1_555 yes C2 C3 C6 112.8(2) . 1_555 1_555 yes C2 C4 C5 103.2(2) . 1_555 1_555 yes C2 C4 H1 111.1 . 1_555 1_555 no C2 C4 H2 111.2 . 1_555 1_555 no C5 C4 H1 110.9 . 1_555 1_555 no C5 C4 H2 111.3 . 1_555 1_555 no H1 C4 H2 109.2 . 1_555 1_555 no C4 C5 C6 106.3(2) . 1_555 1_555 yes C4 C5 C7 115.6(2) . 1_555 1_555 yes C4 C5 H3 106.4 . 1_555 1_555 no C6 C5 C7 115.2(2) . 1_555 1_555 yes C6 C5 H3 106.2 . 1_555 1_555 no C7 C5 H3 106.5 . 1_555 1_555 no C3 C6 C5 103.2(2) . 1_555 1_555 yes C3 C6 H4 111.2 . 1_555 1_555 no C3 C6 H5 110.8 . 1_555 1_555 no C5 C6 H4 111.4 . 1_555 1_555 no C5 C6 H5 110.6 . 1_555 1_555 no H4 C6 H5 109.6 . 1_555 1_555 no C5 C7 C8 109.3(2) . 1_555 1_555 yes C5 C7 C9 112.1(2) . 1_555 1_555 yes C5 C7 C10 109.2(2) . 1_555 1_555 yes C8 C7 C9 108.8(2) . 1_555 1_555 yes C8 C7 C10 108.7(2) . 1_555 1_555 yes C9 C7 C10 108.6(2) . 1_555 1_555 yes C7 C8 H6 109.8 . 1_555 1_555 no C7 C8 H7 109.2 . 1_555 1_555 no C7 C8 H8 110.0 . 1_555 1_555 no H6 C8 H7 108.9 . 1_555 1_555 no H6 C8 H8 109.9 . 1_555 1_555 no H7 C8 H8 109.0 . 1_555 1_555 no C7 C9 H9 109.7 . 1_555 1_555 no C7 C9 H10 109.9 . 1_555 1_555 no C7 C9 H11 109.7 . 1_555 1_555 no H9 C9 H10 109.3 . 1_555 1_555 no H9 C9 H11 109.1 . 1_555 1_555 no H10 C9 H11 109.2 . 1_555 1_555 no C7 C10 H12 110.2 . 1_555 1_555 no C7 C10 H13 109.0 . 1_555 1_555 no C7 C10 H14 109.8 . 1_555 1_555 no H12 C10 H13 109.0 . 1_555 1_555 no H12 C10 H14 110.2 . 1_555 1_555 no H13 C10 H14 108.6 . 1_555 1_555 no #------------------------------------------------------------------------------ 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 S1 C1 S2 C3 -0.7(1) 1_555 1_555 1_555 1_555 yes S1 C1 C1 S1 180.0 1_555 1_555 2_666 2_666 yes S1 C1 C1 S2 -1.9(4) 1_555 1_555 2_666 2_666 yes S1 C2 C3 S2 0.6(3) 1_555 1_555 1_555 1_555 yes S1 C2 C3 C6 177.9(2) 1_555 1_555 1_555 1_555 yes S1 C2 C4 C5 174.4(2) 1_555 1_555 1_555 1_555 yes S2 C1 S1 C2 1.0(1) 1_555 1_555 1_555 1_555 yes S2 C1 C1 S2 180.0 1_555 1_555 2_666 2_666 yes S2 C3 C2 C4 -176.5(2) 1_555 1_555 1_555 1_555 yes S2 C3 C6 C5 -175.3(2) 1_555 1_555 1_555 1_555 yes C1 S1 C2 C3 -1.0(2) 1_555 1_555 1_555 1_555 yes C1 S1 C2 C4 175.7(2) 1_555 1_555 1_555 1_555 yes C1 S2 C3 C2 0.1(2) 1_555 1_555 1_555 1_555 yes C1 S2 C3 C6 -176.6(2) 1_555 1_555 1_555 1_555 yes C1 C1 S1 C2 177.3(2) 1_555 2_666 2_666 2_666 yes C1 C1 S2 C3 -177.5(2) 1_555 2_666 2_666 2_666 yes C2 C3 C6 C5 7.8(3) 1_555 1_555 1_555 1_555 yes C2 C4 C5 C6 13.0(2) 1_555 1_555 1_555 1_555 yes C2 C4 C5 C7 142.2(2) 1_555 1_555 1_555 1_555 yes C3 C2 C4 C5 -8.8(3) 1_555 1_555 1_555 1_555 yes C3 C6 C5 C4 -12.7(2) 1_555 1_555 1_555 1_555 yes C3 C6 C5 C7 -142.1(2) 1_555 1_555 1_555 1_555 yes C4 C2 C3 C6 0.7(3) 1_555 1_555 1_555 1_555 yes C4 C5 C7 C8 58.3(3) 1_555 1_555 1_555 1_555 yes C4 C5 C7 C9 -62.5(3) 1_555 1_555 1_555 1_555 yes C4 C5 C7 C10 177.1(2) 1_555 1_555 1_555 1_555 yes C6 C5 C7 C8 -177.0(2) 1_555 1_555 1_555 1_555 yes C6 C5 C7 C9 62.2(3) 1_555 1_555 1_555 1_555 yes C6 C5 C7 C10 -58.2(3) 1_555 1_555 1_555 1_555 yes _chemical_name_common ;Di(4-t-butylcyclopenteno(1,2-d)(1',2'-d)-1,4,5,8- tetrathiafulva-lene (1c) ; #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_1d _database_code_depnum_ccdc_archive 'CCDC 727314' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C22 H32 S4 ' _chemical_formula_moiety 'C22 H32 S4 ' _chemical_formula_weight 424.73 _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 6.477(1) _cell_length_b 14.667(3) _cell_length_c 6.140(3) _cell_angle_alpha 93.38(3) _cell_angle_beta 93.66(2) _cell_angle_gamma 86.50(2) _cell_volume 580.0(3) _cell_formula_units_Z 1 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.9 _cell_measurement_theta_max 15.0 _cell_measurement_temperature 293.2 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.216 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.414 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.941 _exptl_absorpt_correction_T_max 1.000 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 3659 _diffrn_reflns_av_R_equivalents 0.016 _diffrn_reflns_theta_max 29.99 _diffrn_measured_fraction_theta_max 1.0913 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 1.0913 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 1.32 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 4.1 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^ > 4.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3251 _reflns_number_gt 1561 _reflns_threshold_expression F^2^>4.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0511 _refine_ls_wR_factor_ref 0.1382 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1561 _refine_ls_number_parameters 127 _refine_ls_goodness_of_fit_ref 1.890 _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 0.0000 _refine_diff_density_max 0.26 _refine_diff_density_min -0.21 _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 S1 S 0.3442(1) 0.40454(7) 0.2636(2) 0.0720(3) Uani 1.00 d . . . S2 S 0.7717(1) 0.47095(7) 0.3044(2) 0.0718(3) Uani 1.00 d . . . C1 C 0.5235(5) 0.4748(3) 0.4107(6) 0.064(1) Uani 1.00 d . . . C2 C 0.5192(5) 0.3614(3) 0.0746(6) 0.066(1) Uani 1.00 d . . . C3 C 0.7115(5) 0.3914(3) 0.0949(7) 0.066(1) Uani 1.00 d . . . C4 C 0.4913(6) 0.2912(3) -0.1105(7) 0.080(1) Uani 1.00 d . . . C5A C 0.717(2) 0.2594(9) -0.147(2) 0.073(4) Uani 0.50 d P . . C5B C 0.695(2) 0.2974(8) -0.235(2) 0.065(3) Uani 0.50 d P . . C6 C 0.8438(6) 0.3475(3) -0.0771(7) 0.076(1) Uani 1.00 d . . . C7 C 0.7634(7) 0.2158(3) -0.357(1) 0.108(2) Uani 1.00 d . . . C8 C 0.9611(8) 0.2028(4) -0.450(1) 0.126(2) Uani 1.00 d . . . C9 C 1.022(1) 0.1365(4) -0.609(1) 0.140(3) Uani 1.00 d . . . C10 C 1.218(1) 0.1245(6) -0.698(1) 0.176(3) Uani 1.00 d . . . C11 C 1.293(2) 0.0554(5) -0.829(2) 0.232(5) Uani 1.00 d . . . H1 H 0.4138 0.2424 -0.0719 0.0963 Uiso 1.00 calc . . . H2 H 0.4253 0.3180 -0.2365 0.0963 Uiso 1.00 calc . . . H3 H 0.7548 0.2147 -0.0454 0.0890 Uiso 0.50 calc P . . H4 H 0.8516 0.3866 -0.1949 0.0908 Uiso 1.00 calc . . . H5 H 0.9799 0.3316 -0.0195 0.0908 Uiso 1.00 calc . . . H6 H 0.7167 0.1561 -0.3545 0.1318 Uiso 1.00 calc . . . H7 H 0.6778 0.2497 -0.4600 0.1318 Uiso 1.00 calc . . . H8 H 0.9830 0.2610 -0.5118 0.1555 Uiso 1.00 calc . . . H9 H 1.0605 0.1967 -0.3283 0.1555 Uiso 1.00 calc . . . H10 H 1.0098 0.0806 -0.5419 0.1757 Uiso 1.00 calc . . . H11 H 0.9218 0.1430 -0.7254 0.1757 Uiso 1.00 calc . . . H12 H 1.2185 0.1803 -0.7897 0.2044 Uiso 1.00 calc . . . H13 H 1.3178 0.1350 -0.5832 0.2044 Uiso 1.00 calc . . . H14 H 1.3028 0.0012 -0.7532 0.2950 Uiso 1.00 calc . . . H15 H 1.2028 0.0464 -0.9596 0.2950 Uiso 1.00 calc . . . H16 H 1.4274 0.0667 -0.8765 0.2950 Uiso 1.00 calc . . . H17 H 0.6553 0.3413 -0.3437 0.0890 Uiso 0.50 calc P . . 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 S1 0.0464(5) 0.0977(8) 0.0724(7) -0.0217(5) 0.0056(4) -0.0129(6) S2 0.0480(5) 0.0982(8) 0.0700(7) -0.0232(5) 0.0084(4) -0.0131(6) C1 0.045(2) 0.085(3) 0.062(2) -0.017(2) 0.000(2) -0.001(2) C2 0.049(2) 0.080(2) 0.068(2) -0.014(2) 0.002(2) -0.007(2) C3 0.051(2) 0.078(2) 0.071(2) -0.014(2) 0.005(2) -0.006(2) C4 0.064(2) 0.096(3) 0.081(3) -0.025(2) 0.007(2) -0.015(2) C5A 0.065(5) 0.093(9) 0.064(7) -0.013(5) -0.002(5) 0.005(5) C5B 0.061(5) 0.083(8) 0.051(6) -0.011(5) 0.003(5) -0.004(5) C6 0.056(2) 0.097(3) 0.076(3) -0.015(2) 0.009(2) -0.010(2) C7 0.083(3) 0.092(3) 0.148(5) -0.016(2) 0.027(3) -0.039(3) C8 0.086(3) 0.138(4) 0.148(5) -0.011(3) 0.026(3) -0.060(4) C9 0.125(5) 0.114(4) 0.181(7) -0.016(4) 0.054(5) -0.040(4) C10 0.131(5) 0.181(6) 0.216(9) -0.016(5) 0.077(6) -0.078(6) C11 0.213(9) 0.144(6) 0.35(2) 0.016(6) 0.134(10) -0.036(8) #------------------------------------------------------------------------------ _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SHELXS86 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _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 S1 C1 1.769(3) . . yes S1 C2 1.739(4) . . yes S2 C1 1.769(3) . . yes S2 C3 1.727(4) . . yes C1 C1 1.327(7) . 2_666 yes C2 C3 1.342(5) . . yes C2 C4 1.498(5) . . yes C3 C6 1.494(6) . . yes C4 C5A 1.53(1) . . yes C4 C5B 1.58(1) . . yes C4 H1 0.948 . . no C4 H2 0.953 . . no C5A C5B 0.80(1) . . yes C5A C6 1.60(1) . . yes C5A H3 0.944 . . no C5A C7 1.45(1) . . yes C5B C6 1.52(1) . . yes C5B C7 1.44(1) . . yes C5B H17 0.965 . . no C7 C8 1.432(7) . . yes C7 H6 0.944 . . no C7 H7 0.955 . . no C8 C9 1.395(8) . . yes C8 H8 0.975 . . no C8 H9 0.959 . . no C9 C10 1.406(8) . . yes C9 H10 0.950 . . no C9 H11 0.938 . . no C10 C11 1.34(1) . . yes C10 H12 1.023 . . no C10 H13 0.938 . . no C11 H14 0.941 . . no C11 H15 0.968 . . no C11 H16 0.965 . . 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 C1 S1 C2 94.4(2) . 1_555 1_555 yes C1 S2 C3 94.4(2) . 1_555 1_555 yes S1 C1 S2 114.8(2) . 1_555 1_555 yes S1 C1 C1 122.5(3) . 1_555 2_666 yes S2 C1 C1 122.7(3) . 1_555 2_666 yes S1 C2 C3 117.8(3) . 1_555 1_555 yes S1 C2 C4 129.5(3) . 1_555 1_555 yes C3 C2 C4 112.6(3) . 1_555 1_555 yes S2 C3 C2 118.6(3) . 1_555 1_555 yes S2 C3 C6 129.8(3) . 1_555 1_555 yes C2 C3 C6 111.5(3) . 1_555 1_555 yes C2 C4 C5A 101.2(5) . 1_555 1_555 yes C2 C4 C5B 102.3(5) . 1_555 1_555 yes C2 C4 H1 111.9 . 1_555 1_555 no C2 C4 H2 111.1 . 1_555 1_555 no C5A C4 C5B 29.8(4) . 1_555 1_555 yes C5A C4 H1 111.6 . 1_555 1_555 no C5A C4 H2 111.5 . 1_555 1_555 no C5B C4 H1 134.4 . 1_555 1_555 no C5B C4 H2 83.9 . 1_555 1_555 no H1 C4 H2 109.3 . 1_555 1_555 no C4 C5A C5B 78(1) . 1_555 1_555 yes C4 C5A C6 104.1(8) . 1_555 1_555 yes C4 C5A C7 118.2(8) . 1_555 1_555 yes C4 C5A H3 106.7 . 1_555 1_555 no C4 C5A H6 108.3 . 1_555 1_555 no C4 C5A H7 94.9 . 1_555 1_555 no C4 C5A H17 75.9 . 1_555 1_555 no C5B C5A C6 69(1) . 1_555 1_555 yes C5B C5A C7 73(1) . 1_555 1_555 yes C5B C5A H3 174.8 . 1_555 1_555 no C6 C5A C7 114.7(7) . 1_555 1_555 yes C6 C5A H3 107.7 . 1_555 1_555 no C6 C5A H17 72.0 . 1_555 1_555 no C7 C5A H3 104.9 . 1_555 1_555 no C4 C5B C5A 71(1) . 1_555 1_555 yes C4 C5B C6 105.8(6) . 1_555 1_555 yes C4 C5B C7 115.9(7) . 1_555 1_555 yes C4 C5B H17 103.5 . 1_555 1_555 no C5A C5B C6 80(1) . 1_555 1_555 yes C5A C5B C7 74(1) . 1_555 1_555 yes C5A C5B H17 174.4 . 1_555 1_555 no C6 C5B C7 120.7(8) . 1_555 1_555 yes C6 C5B H17 103.6 . 1_555 1_555 no C7 C5B H17 105.2 . 1_555 1_555 no C3 C6 C5A 100.0(5) . 1_555 1_555 yes C3 C6 C5B 104.8(5) . 1_555 1_555 yes C3 C6 H4 111.2 . 1_555 1_555 no C3 C6 H5 111.7 . 1_555 1_555 no C5A C6 C5B 29.6(4) . 1_555 1_555 yes C5A C6 H4 112.4 . 1_555 1_555 no C5A C6 H5 112.2 . 1_555 1_555 no C5B C6 H4 83.8 . 1_555 1_555 no C5B C6 H5 132.4 . 1_555 1_555 no H4 C6 H5 109.1 . 1_555 1_555 no C5A C7 C5B 32.2(4) . 1_555 1_555 yes C5A C7 C8 127.8(6) . 1_555 1_555 yes C5A C7 H6 104.9 . 1_555 1_555 no C5A C7 H7 104.2 . 1_555 1_555 no C5B C7 C8 124.0(6) . 1_555 1_555 yes C5B C7 H6 128.7 . 1_555 1_555 no C5B C7 H7 75.4 . 1_555 1_555 no C8 C7 H6 104.4 . 1_555 1_555 no C8 C7 H7 105.2 . 1_555 1_555 no H6 C7 H7 109.6 . 1_555 1_555 no C7 C8 C9 127.5(5) . 1_555 1_555 yes C7 C8 H8 105.0 . 1_555 1_555 no C7 C8 H9 105.6 . 1_555 1_555 no C9 C8 H8 104.6 . 1_555 1_555 no C9 C8 H9 106.1 . 1_555 1_555 no H8 C8 H9 106.6 . 1_555 1_555 no C8 C9 C10 126.7(6) . 1_555 1_555 yes C8 C9 H8 29.9 . 1_555 1_555 no C8 C9 H9 29.0 . 1_555 1_555 no C8 C9 H10 103.4 . 1_555 1_555 no C8 C9 H11 104.7 . 1_555 1_555 no C10 C9 H10 103.0 . 1_555 1_555 no C10 C9 H11 108.0 . 1_555 1_555 no H10 C9 H11 110.5 . 1_555 1_555 no C9 C10 C11 129.0(8) . 1_555 1_555 yes C9 C10 H12 102.0 . 1_555 1_555 no C9 C10 H13 107.6 . 1_555 1_555 no C11 C10 H12 103.6 . 1_555 1_555 no C11 C10 H13 107.6 . 1_555 1_555 no H12 C10 H13 104.5 . 1_555 1_555 no C10 C11 H14 109.1 . 1_555 1_555 no C10 C11 H15 111.2 . 1_555 1_555 no C10 C11 H16 112.1 . 1_555 1_555 no H14 C11 H15 108.7 . 1_555 1_555 no H14 C11 H16 109.0 . 1_555 1_555 no H15 C11 H16 106.7 . 1_555 1_555 no #------------------------------------------------------------------------------ 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 S1 C1 S2 C3 -1.4(2) 1_555 1_555 1_555 1_555 yes S1 C1 C1 S1 -180.0 1_555 1_555 2_666 2_666 yes S1 C1 C1 S2 -1.3(7) 1_555 1_555 2_666 2_666 yes S1 C2 C3 S2 -0.5(5) 1_555 1_555 1_555 1_555 yes S1 C2 C3 C6 179.3(3) 1_555 1_555 1_555 1_555 yes S1 C2 C4 C5A -158.7(5) 1_555 1_555 1_555 1_555 yes S1 C2 C4 C5B 170.9(5) 1_555 1_555 1_555 1_555 yes S2 C1 S1 C2 1.2(2) 1_555 1_555 1_555 1_555 yes S2 C1 C1 S2 -180.0 1_555 1_555 2_666 2_666 yes S2 C3 C2 C4 -178.7(3) 1_555 1_555 1_555 1_555 yes S2 C3 C6 C5A 159.8(5) 1_555 1_555 1_555 1_555 yes S2 C3 C6 C5B -170.3(5) 1_555 1_555 1_555 1_555 yes C1 S1 C2 C3 -0.4(4) 1_555 1_555 1_555 1_555 yes C1 S1 C2 C4 177.3(4) 1_555 1_555 1_555 1_555 yes C1 S2 C3 C2 1.2(4) 1_555 1_555 1_555 1_555 yes C1 S2 C3 C6 -178.7(4) 1_555 1_555 1_555 1_555 yes C1 C1 S1 C2 177.6(5) 1_555 2_666 2_666 2_666 yes C1 C1 S2 C3 -177.4(5) 1_555 2_666 2_666 2_666 yes C2 C3 C6 C5A -20.1(6) 1_555 1_555 1_555 1_555 yes C2 C3 C6 C5B 9.9(6) 1_555 1_555 1_555 1_555 yes C2 C4 C5A C5B -95(1) 1_555 1_555 1_555 1_555 yes C2 C4 C5A C6 -30.1(7) 1_555 1_555 1_555 1_555 yes C2 C4 C5A C7 -158.7(8) 1_555 1_555 1_555 1_555 yes C2 C4 C5B C5A 91(1) 1_555 1_555 1_555 1_555 yes C2 C4 C5B C6 16.5(7) 1_555 1_555 1_555 1_555 yes C2 C4 C5B C7 153.2(7) 1_555 1_555 1_555 1_555 yes C3 C2 C4 C5A 19.2(6) 1_555 1_555 1_555 1_555 yes C3 C2 C4 C5B -11.2(6) 1_555 1_555 1_555 1_555 yes C3 C6 C5A C4 30.8(7) 1_555 1_555 1_555 1_555 yes C3 C6 C5A C5B 102(1) 1_555 1_555 1_555 1_555 yes C3 C6 C5A C7 161.4(7) 1_555 1_555 1_555 1_555 yes C3 C6 C5B C4 -16.1(7) 1_555 1_555 1_555 1_555 yes C3 C6 C5B C5A -84(1) 1_555 1_555 1_555 1_555 yes C3 C6 C5B C7 -150.3(7) 1_555 1_555 1_555 1_555 yes C4 C2 C3 C6 1.2(5) 1_555 1_555 1_555 1_555 yes C4 C5A C5B C6 110.0(4) 1_555 1_555 1_555 1_555 yes C4 C5A C5B C7 -124.5(5) 1_555 1_555 1_555 1_555 yes C4 C5A C6 C5B -71(1) 1_555 1_555 1_555 1_555 yes C4 C5A C7 C5B 66(1) 1_555 1_555 1_555 1_555 yes C4 C5A C7 C8 161.8(6) 1_555 1_555 1_555 1_555 yes C4 C5B C5A C6 -110.0(4) 1_555 1_555 1_555 1_555 yes C4 C5B C5A C7 124.5(5) 1_555 1_555 1_555 1_555 yes C4 C5B C6 C5A 68(1) 1_555 1_555 1_555 1_555 yes C4 C5B C7 C5A -60(1) 1_555 1_555 1_555 1_555 yes C4 C5B C7 C8 -169.0(6) 1_555 1_555 1_555 1_555 yes C5A C4 C5B C6 -74(1) 1_555 1_555 1_555 1_555 yes C5A C4 C5B C7 62(1) 1_555 1_555 1_555 1_555 yes C5A C5B C7 C8 -108(1) 1_555 1_555 1_555 1_555 yes C5A C6 C5B C7 -66(1) 1_555 1_555 1_555 1_555 yes C5A C7 C5B C6 69(1) 1_555 1_555 1_555 1_555 yes C5A C7 C8 C9 156.1(9) 1_555 1_555 1_555 1_555 yes C5B C4 C5A C6 65(1) 1_555 1_555 1_555 1_555 yes C5B C4 C5A C7 -63(1) 1_555 1_555 1_555 1_555 yes C5B C5A C7 C8 95(1) 1_555 1_555 1_555 1_555 yes C5B C6 C5A C7 59(1) 1_555 1_555 1_555 1_555 yes C5B C7 C5A C6 -57(1) 1_555 1_555 1_555 1_555 yes C5B C7 C8 C9 -164.1(8) 1_555 1_555 1_555 1_555 yes C6 C5A C5B C7 125.5(5) 1_555 1_555 1_555 1_555 yes C6 C5A C7 C8 38(1) 1_555 1_555 1_555 1_555 yes C6 C5B C5A C7 -125.5(5) 1_555 1_555 1_555 1_555 yes C6 C5B C7 C8 -39(1) 1_555 1_555 1_555 1_555 yes C7 C8 C9 C10 -179.6(8) 1_555 1_555 1_555 1_555 yes C8 C9 C10 C11 170(1) 1_555 1_555 1_555 1_555 yes _chemical_name_common ;Di(4-n-butylcyclopenteno(1,2-d)(1',2'-d)-1,4,5,8-tetrathia- fulvalene (1d) ; #------------------------------------------------------------------------------ #------------------------------------------------------------------------------ data_1e _database_code_depnum_ccdc_archive 'CCDC 727315' #------------------------------------------------------------------------------ # CHEMICAL DATA _chemical_formula_sum 'C22 H32 S4 ' _chemical_formula_moiety 'C22 H32 S4 ' _chemical_formula_weight 424.73 _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 6.3870(9) _cell_length_b 14.408(3) _cell_length_c 6.320(1) _cell_angle_alpha 93.17(2) _cell_angle_beta 110.22(1) _cell_angle_gamma 91.12(1) _cell_volume 544.4(2) _cell_formula_units_Z 1 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 13.0 _cell_measurement_theta_max 14.7 _cell_measurement_temperature 293.2 #------------------------------------------------------------------------------ _exptl_crystal_description prismatic _exptl_crystal_colour colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_size_rad ? _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_absorpt_coefficient_mu 0.441 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North, Phillips & Mathews, 1968)' _exptl_absorpt_correction_T_min 0.959 _exptl_absorpt_correction_T_max 0.999 #------------------------------------------------------------------------------ # EXPERIMENTAL DATA _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku AFC7R' _diffrn_measurement_method \w-2\q _diffrn_reflns_number 3425 _diffrn_reflns_av_R_equivalents 0.012 _diffrn_reflns_theta_max 29.99 _diffrn_measured_fraction_theta_max 1.0889 _diffrn_reflns_theta_full 29.99 _diffrn_measured_fraction_theta_full 1.0889 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 8 _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0.13 #------------------------------------------------------------------------------ # REFINEMENT DATA _refine_special_details ; Refinement using reflections with F^2^ > 4.0 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^ > 4.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3051 _reflns_number_gt 1922 _reflns_threshold_expression F^2^>4.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_ref 0.0860 _refine_ls_hydrogen_treatment noref _refine_ls_number_reflns 1922 _refine_ls_number_parameters 118 _refine_ls_goodness_of_fit_ref 1.144 _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 0.0003 _refine_diff_density_max 0.20 _refine_diff_density_min -0.20 _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 S1 S 0.27637(7) 0.56787(4) 0.15327(9) 0.0429(1) Uani 1.00 d . . . S2 S 0.77201(7) 0.55858(4) 0.30086(9) 0.0427(1) Uani 1.00 d . . . C C 0.8285(4) 0.8206(2) 1.0805(4) 0.0612(7) Uani 1.00 d . . . C1 C 0.5097(3) 0.5263(1) 0.0948(3) 0.0354(5) Uani 1.00 d . . . C2 C 0.4376(3) 0.6304(1) 0.4022(3) 0.0393(5) Uani 1.00 d . . . C3 C 0.6591(3) 0.6264(1) 0.4679(3) 0.0398(5) Uani 1.00 d . . . C4 C 0.3640(3) 0.6943(1) 0.5544(4) 0.0477(6) Uani 1.00 d . . . C5 C 0.5845(3) 0.7170(1) 0.7569(4) 0.0429(5) Uani 1.00 d . . . C6 C 0.7778(3) 0.6876(2) 0.6742(4) 0.0481(6) Uani 1.00 d . . . C7 C 0.6108(3) 0.8160(1) 0.8730(4) 0.0436(5) Uani 1.00 d . . . C8 C 0.4106(4) 0.8311(2) 0.9492(5) 0.0651(8) Uani 1.00 d . . . C9 C 0.6187(5) 0.8901(2) 0.7136(5) 0.0669(8) Uani 1.00 d . . . C10 C 0.8897(5) 0.9119(2) 1.2234(5) 0.0752(9) Uani 1.00 d . . . H1 H 0.8153 0.7736 1.1759 0.0738 Uiso 1.00 calc . . . H2 H 0.9478 0.8071 1.0279 0.0738 Uiso 1.00 calc . . . H3 H 0.3054 0.7493 0.4823 0.0575 Uiso 1.00 calc . . . H4 H 0.2550 0.6648 0.6014 0.0575 Uiso 1.00 calc . . . H5 H 0.5842 0.6755 0.8686 0.0515 Uiso 1.00 calc . . . H6 H 0.8860 0.6550 0.7841 0.0584 Uiso 1.00 calc . . . H7 H 0.8482 0.7405 0.6384 0.0584 Uiso 1.00 calc . . . H8 H 0.4254 0.8910 1.0253 0.0783 Uiso 1.00 calc . . . H9 H 0.2768 0.8268 0.8212 0.0783 Uiso 1.00 calc . . . H10 H 0.4046 0.7849 1.0490 0.0783 Uiso 1.00 calc . . . H11 H 0.6330 0.9499 0.7896 0.0804 Uiso 1.00 calc . . . H12 H 0.7431 0.8812 0.6661 0.0804 Uiso 1.00 calc . . . H13 H 0.4851 0.8856 0.5855 0.0804 Uiso 1.00 calc . . . H14 H 1.0262 0.9066 1.3450 0.0910 Uiso 1.00 calc . . . H15 H 0.9054 0.9601 1.1330 0.0910 Uiso 1.00 calc . . . H16 H 0.7747 0.9263 1.2824 0.0910 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 S1 0.0255(2) 0.0535(3) 0.0439(3) 0.0008(2) 0.0070(2) -0.0099(2) S2 0.0259(2) 0.0541(3) 0.0419(3) 0.0040(2) 0.0056(2) -0.0087(2) C 0.060(1) 0.058(1) 0.057(1) -0.007(1) 0.013(1) -0.015(1) C1 0.0266(8) 0.038(1) 0.038(1) 0.0020(7) 0.0071(8) 0.0004(8) C2 0.0312(9) 0.042(1) 0.041(1) -0.0004(7) 0.0092(8) -0.0063(9) C3 0.0325(9) 0.043(1) 0.039(1) 0.0013(8) 0.0079(8) -0.0055(9) C4 0.0340(10) 0.050(1) 0.055(1) -0.0009(8) 0.0140(9) -0.014(1) C5 0.042(1) 0.042(1) 0.043(1) -0.0036(8) 0.0141(9) -0.0057(9) C6 0.0340(9) 0.054(1) 0.048(1) 0.0037(8) 0.0057(9) -0.013(1) C7 0.046(1) 0.039(1) 0.047(1) -0.0034(8) 0.0194(9) -0.0063(9) C8 0.062(1) 0.062(2) 0.077(2) -0.004(1) 0.035(1) -0.020(1) C9 0.080(2) 0.051(1) 0.071(2) -0.003(1) 0.029(1) 0.004(1) C10 0.079(2) 0.075(2) 0.064(2) -0.017(1) 0.022(1) -0.022(1) #------------------------------------------------------------------------------ _computing_data_collection WinAFC _computing_cell_refinement WinAFC _computing_data_reduction 'teXsan Ver. 1.10' _computing_structure_solution SHELXS86 _computing_structure_refinement 'teXsan Ver. 1.10' _computing_publication_material 'teXsan Ver. 1.10' _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 S1 C1 1.763(2) . . yes S1 C2 1.742(2) . . yes S2 C1 1.764(2) . . yes S2 C3 1.741(2) . . yes C C7 1.544(3) . . yes C C10 1.517(3) . . yes C H1 0.952 . . no C H2 0.950 . . no C1 C1 1.349(4) . 2_665 yes C2 C3 1.333(3) . . yes C2 C4 1.492(3) . . yes C3 C6 1.488(3) . . yes C4 C5 1.555(3) . . yes C4 H3 0.953 . . no C4 H4 0.949 . . no C5 C6 1.556(3) . . yes C5 C7 1.546(3) . . yes C5 H5 0.950 . . no C6 H6 0.947 . . no C6 H7 0.954 . . no C7 C8 1.530(3) . . yes C7 C9 1.519(3) . . yes C8 H8 0.951 . . no C8 H9 0.951 . . no C8 H10 0.951 . . no C9 H11 0.951 . . no C9 H12 0.950 . . no C9 H13 0.950 . . no C10 H14 0.950 . . no C10 H15 0.949 . . no C10 H16 0.953 . . 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 C1 S1 C2 93.89(8) . 1_555 1_555 yes C1 S2 C3 93.94(9) . 1_555 1_555 yes C7 C C10 117.1(2) . 1_555 1_555 yes C7 C H1 107.5 . 1_555 1_555 no C7 C H2 107.6 . 1_555 1_555 no C10 C H1 107.6 . 1_555 1_555 no C10 C H2 107.6 . 1_555 1_555 no H1 C H2 109.2 . 1_555 1_555 no S1 C1 S2 115.5(1) . 1_555 1_555 yes S1 C1 C1 122.5(2) . 1_555 2_665 yes S2 C1 C1 121.9(2) . 1_555 2_665 yes S1 C2 C3 118.4(2) . 1_555 1_555 yes S1 C2 C4 129.0(1) . 1_555 1_555 yes C3 C2 C4 112.6(2) . 1_555 1_555 yes S2 C3 C2 118.2(2) . 1_555 1_555 yes S2 C3 C6 128.5(1) . 1_555 1_555 yes C2 C3 C6 113.1(2) . 1_555 1_555 yes C2 C4 C5 102.6(2) . 1_555 1_555 yes C2 C4 H3 111.1 . 1_555 1_555 no C2 C4 H4 111.4 . 1_555 1_555 no C5 C4 H3 111.0 . 1_555 1_555 no C5 C4 H4 111.3 . 1_555 1_555 no H3 C4 H4 109.3 . 1_555 1_555 no C4 C5 C6 106.4(2) . 1_555 1_555 yes C4 C5 C7 116.0(2) . 1_555 1_555 yes C4 C5 H5 106.1 . 1_555 1_555 no C6 C5 C7 115.6(2) . 1_555 1_555 yes C6 C5 H5 106.0 . 1_555 1_555 no C7 C5 H5 106.0 . 1_555 1_555 no C3 C6 C5 102.4(2) . 1_555 1_555 yes C3 C6 H6 111.6 . 1_555 1_555 no C3 C6 H7 111.1 . 1_555 1_555 no C5 C6 H6 111.4 . 1_555 1_555 no C5 C6 H7 110.9 . 1_555 1_555 no H6 C6 H7 109.4 . 1_555 1_555 no C C7 C5 107.5(2) . 1_555 1_555 yes C C7 C8 109.9(2) . 1_555 1_555 yes C C7 C9 110.5(2) . 1_555 1_555 yes C5 C7 C8 108.0(2) . 1_555 1_555 yes C5 C7 C9 111.7(2) . 1_555 1_555 yes C8 C7 C9 109.1(2) . 1_555 1_555 yes C7 C8 H8 109.5 . 1_555 1_555 no C7 C8 H9 109.6 . 1_555 1_555 no C7 C8 H10 109.6 . 1_555 1_555 no H8 C8 H9 109.3 . 1_555 1_555 no H8 C8 H10 109.3 . 1_555 1_555 no H9 C8 H10 109.4 . 1_555 1_555 no C7 C9 H11 109.4 . 1_555 1_555 no C7 C9 H12 109.5 . 1_555 1_555 no C7 C9 H13 109.5 . 1_555 1_555 no H11 C9 H12 109.4 . 1_555 1_555 no H11 C9 H13 109.5 . 1_555 1_555 no H12 C9 H13 109.5 . 1_555 1_555 no C C10 H14 109.7 . 1_555 1_555 no C C10 H15 109.6 . 1_555 1_555 no C C10 H16 109.4 . 1_555 1_555 no H14 C10 H15 109.6 . 1_555 1_555 no H14 C10 H16 109.3 . 1_555 1_555 no H15 C10 H16 109.3 . 1_555 1_555 no #------------------------------------------------------------------------------ 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 S1 C1 S2 C3 -3.0(1) 1_555 1_555 1_555 1_555 yes S1 C1 C1 S1 -180.0 1_555 1_555 2_665 2_665 yes S1 C1 C1 S2 -0.3(3) 1_555 1_555 2_665 2_665 yes S1 C2 C3 S2 -0.3(2) 1_555 1_555 1_555 1_555 yes S1 C2 C3 C6 176.2(2) 1_555 1_555 1_555 1_555 yes S1 C2 C4 C5 173.5(2) 1_555 1_555 1_555 1_555 yes S2 C1 S1 C2 2.9(1) 1_555 1_555 1_555 1_555 yes S2 C1 C1 S2 -180.0 1_555 1_555 2_665 2_665 yes S2 C3 C2 C4 -177.3(1) 1_555 1_555 1_555 1_555 yes S2 C3 C6 C5 -172.9(2) 1_555 1_555 1_555 1_555 yes C C7 C5 C4 174.9(2) 1_555 1_555 1_555 1_555 yes C C7 C5 C6 -59.5(2) 1_555 1_555 1_555 1_555 yes C1 S1 C2 C3 -1.6(2) 1_555 1_555 1_555 1_555 yes C1 S1 C2 C4 174.9(2) 1_555 1_555 1_555 1_555 yes C1 S2 C3 C2 2.0(2) 1_555 1_555 1_555 1_555 yes C1 S2 C3 C6 -173.9(2) 1_555 1_555 1_555 1_555 yes C1 C1 S1 C2 176.8(2) 1_555 2_665 2_665 2_665 yes C1 C1 S2 C3 -176.7(2) 1_555 2_665 2_665 2_665 yes C2 C3 C6 C5 11.1(2) 1_555 1_555 1_555 1_555 yes C2 C4 C5 C6 16.0(2) 1_555 1_555 1_555 1_555 yes C2 C4 C5 C7 146.2(2) 1_555 1_555 1_555 1_555 yes C3 C2 C4 C5 -9.9(2) 1_555 1_555 1_555 1_555 yes C3 C6 C5 C4 -16.4(2) 1_555 1_555 1_555 1_555 yes C3 C6 C5 C7 -146.8(2) 1_555 1_555 1_555 1_555 yes C4 C2 C3 C6 -0.8(3) 1_555 1_555 1_555 1_555 yes C4 C5 C7 C8 56.3(2) 1_555 1_555 1_555 1_555 yes C4 C5 C7 C9 -63.7(2) 1_555 1_555 1_555 1_555 yes C5 C7 C C10 -179.7(2) 1_555 1_555 1_555 1_555 yes C6 C5 C7 C8 -178.1(2) 1_555 1_555 1_555 1_555 yes C6 C5 C7 C9 61.9(2) 1_555 1_555 1_555 1_555 yes C8 C7 C C10 -62.4(3) 1_555 1_555 1_555 1_555 yes C9 C7 C C10 58.2(3) 1_555 1_555 1_555 1_555 yes #------------------------------------------------------------------------------ _chemical_name_common ;Di(4-(1,1-dimethylpropyl)penteno(1,2-d)(1',2'-d)-1,4,5,8- tetrathiafulvalene ;