# Supplementary Material (ESI) for PCCP # This journal is (c) the Owner Societies 2010 data_global _journal_name_full Phys.Chem.Chem.Phys.(PCCP) _journal_coden_Cambridge 1326 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Michel Geoffroy' _publ_contact_author_email MICHEL.GEOFFROY@UNIGE.CH _publ_section_title ; Bis(Tetrathiafulvalenes) with Aromatic Bridges: Electron Delocalisation in the Oxidized Species through EPR and Theoretical Studies ; loop_ _publ_author_name 'Michel Geoffroy' 'Narcis Avarvari' 'Theo Berclaz' 'Philippe Grosshans' F.Riobe ; H.Sidorenkova ; # Attachment 'Pyr_TTF-revised.cif' data_Pyr-TTF _database_code_depnum_ccdc_archive 'CCDC 758083' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common Pyr-TTF _chemical_melting_point ? _chemical_formula_moiety 'C11 H7 N1 S4' _chemical_formula_sum 'C11 H7 N S4' _chemical_formula_weight 281.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 11.767(1) _cell_length_b 8.302(1) _cell_length_c 12.991(1) _cell_angle_alpha 90.00 _cell_angle_beta 111.53(1) _cell_angle_gamma 90.00 _cell_volume 1180.6(1) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2035 _cell_measurement_theta_min 2.98 _cell_measurement_theta_max 24.00 _exptl_crystal_description plate _exptl_crystal_colour orange _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_diffrn 1.583 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.772 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.883485 _exptl_absorpt_correction_T_max 1 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type area_detector _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9999 _diffrn_reflns_av_R_equivalents 0.0440 _diffrn_reflns_av_sigmaI/netI 0.0398 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.98 _diffrn_reflns_theta_max 24.00 _reflns_number_total 1845 _reflns_number_gt 1237 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)' _computing_data_reduction 'Denzo and Scalepak' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0213P)^2^+1.3416P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1845 _refine_ls_number_parameters 173 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0842 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0778 _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_restrained_S_all 1.080 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4942(3) 0.1898(4) 0.0823(3) 0.0379(9) Uani 1 1 d . . . C2 C 0.4049(4) 0.1690(5) 0.1214(3) 0.0492(10) Uani 1 1 d . . . C3 C 0.5889(3) 0.0275(5) 0.2652(3) 0.0448(10) Uani 1 1 d . . . C4 C 0.6632(3) -0.0516(5) 0.3541(3) 0.0478(10) Uani 1 1 d . . . C5 C 0.8512(5) -0.1574(6) 0.5114(4) 0.0734(15) Uani 1 1 d . . . C6 C 0.7614(5) -0.1708(6) 0.5470(4) 0.0719(14) Uani 1 1 d . . . C7 C 0.4873(3) 0.2729(4) -0.0187(3) 0.0392(9) Uani 1 1 d . . . C8 C 0.3808(4) 0.3450(5) -0.0889(3) 0.0476(10) Uani 1 1 d . . . C9 C 0.3798(4) 0.4162(6) -0.1837(4) 0.0563(12) Uani 1 1 d . . . C10 C 0.4849(4) 0.4192(5) -0.2057(4) 0.0578(12) Uani 1 1 d . . . C11 C 0.5867(4) 0.3499(6) -0.1310(4) 0.0610(12) Uani 1 1 d . . . N1 N 0.5914(3) 0.2765(4) -0.0387(3) 0.0497(8) Uani 1 1 d . . . S1 S 0.63667(8) 0.10474(13) 0.16131(8) 0.0472(3) Uani 1 1 d . . . S2 S 0.43548(9) 0.06831(15) 0.24452(9) 0.0608(4) Uani 1 1 d . . . S3 S 0.81749(10) -0.08820(16) 0.37772(9) 0.0634(4) Uani 1 1 d . . . S4 S 0.61620(11) -0.12050(16) 0.45973(10) 0.0692(4) Uani 1 1 d . . . H3 H 0.327(3) 0.209(4) 0.087(3) 0.056(12) Uiso 1 1 d . . . H5 H 0.930(4) -0.187(6) 0.544(4) 0.084(16) Uiso 1 1 d . . . H6 H 0.771(4) -0.208(6) 0.615(4) 0.096(17) Uiso 1 1 d . . . H8 H 0.309(3) 0.342(4) -0.074(3) 0.050(11) Uiso 1 1 d . . . H9 H 0.308(4) 0.456(5) -0.228(3) 0.071(14) Uiso 1 1 d . . . H10 H 0.486(4) 0.464(5) -0.267(3) 0.068(14) Uiso 1 1 d . . . H11 H 0.662(4) 0.350(5) -0.140(3) 0.065(12) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.029(2) 0.041(2) 0.043(2) -0.0062(18) 0.0133(17) -0.0032(17) C2 0.035(2) 0.059(3) 0.053(2) -0.001(2) 0.015(2) -0.003(2) C3 0.037(2) 0.057(3) 0.044(2) -0.003(2) 0.0183(19) -0.0031(19) C4 0.042(2) 0.061(3) 0.045(2) 0.003(2) 0.021(2) -0.001(2) C5 0.068(3) 0.094(4) 0.055(3) 0.010(3) 0.019(3) 0.032(3) C6 0.087(4) 0.079(4) 0.051(3) 0.013(3) 0.027(3) 0.023(3) C7 0.034(2) 0.036(2) 0.045(2) -0.0069(18) 0.0108(19) -0.0051(17) C8 0.032(2) 0.054(3) 0.056(3) 0.002(2) 0.016(2) -0.002(2) C9 0.041(3) 0.060(3) 0.061(3) 0.007(2) 0.009(2) 0.007(2) C10 0.061(3) 0.063(3) 0.055(3) 0.016(2) 0.027(3) 0.013(2) C11 0.046(3) 0.078(3) 0.065(3) 0.016(3) 0.028(3) 0.013(2) N1 0.0349(18) 0.065(2) 0.053(2) 0.0099(18) 0.0205(16) 0.0054(16) S1 0.0319(5) 0.0682(7) 0.0451(6) 0.0066(5) 0.0182(5) 0.0020(5) S2 0.0359(6) 0.0955(9) 0.0578(7) 0.0107(6) 0.0252(5) 0.0004(6) S3 0.0457(6) 0.0940(9) 0.0539(6) 0.0075(6) 0.0223(5) 0.0136(6) S4 0.0669(8) 0.0890(10) 0.0632(7) 0.0193(7) 0.0373(6) 0.0034(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.336(5) . ? C1 C7 1.459(5) . ? C1 S1 1.761(3) . ? C2 S2 1.722(4) . ? C2 H3 0.92(4) . ? C3 C4 1.337(5) . ? C3 S2 1.758(4) . ? C3 S1 1.762(4) . ? C4 S4 1.753(4) . ? C4 S3 1.753(4) . ? C5 C6 1.304(7) . ? C5 S3 1.731(5) . ? C5 H5 0.90(4) . ? C6 S4 1.720(5) . ? C6 H6 0.91(5) . ? C7 N1 1.342(4) . ? C7 C8 1.386(5) . ? C8 C9 1.362(6) . ? C8 H8 0.93(3) . ? C9 C10 1.369(6) . ? C9 H9 0.89(4) . ? C10 C11 1.362(6) . ? C10 H10 0.88(4) . ? C11 N1 1.328(5) . ? C11 H11 0.94(4) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C7 127.7(3) . . ? C2 C1 S1 116.1(3) . . ? C7 C1 S1 116.2(2) . . ? C1 C2 S2 119.4(3) . . ? C1 C2 H3 124(2) . . ? S2 C2 H3 117(2) . . ? C4 C3 S2 122.4(3) . . ? C4 C3 S1 123.3(3) . . ? S2 C3 S1 114.3(2) . . ? C3 C4 S4 122.9(3) . . ? C3 C4 S3 122.9(3) . . ? S4 C4 S3 114.2(2) . . ? C6 C5 S3 117.8(4) . . ? C6 C5 H5 130(3) . . ? S3 C5 H5 112(3) . . ? C5 C6 S4 118.9(4) . . ? C5 C6 H6 123(3) . . ? S4 C6 H6 118(3) . . ? N1 C7 C8 122.2(3) . . ? N1 C7 C1 115.5(3) . . ? C8 C7 C1 122.3(3) . . ? C9 C8 C7 119.2(4) . . ? C9 C8 H8 119(2) . . ? C7 C8 H8 122(2) . . ? C8 C9 C10 119.2(4) . . ? C8 C9 H9 116(3) . . ? C10 C9 H9 125(3) . . ? C11 C10 C9 118.0(4) . . ? C11 C10 H10 121(3) . . ? C9 C10 H10 121(3) . . ? N1 C11 C10 124.9(4) . . ? N1 C11 H11 113(2) . . ? C10 C11 H11 123(2) . . ? C11 N1 C7 116.5(3) . . ? C1 S1 C3 95.13(17) . . ? C2 S2 C3 95.08(19) . . ? C5 S3 C4 94.3(2) . . ? C6 S4 C4 94.2(2) . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.254 _refine_diff_density_min -0.217 _refine_diff_density_rms 0.056