# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Richard Oakley' _publ_contact_author_address ; Department of Chemistry University of Waterloo Waterloo Ontario N2L 3G1 CANADA ; _publ_contact_author_email OAKLEY@SCIBORG.UWATERLOO.CA _publ_section_title ; The effect of selenium incorporation on the bandwidth and conductivity of neutral radical conductors ; loop_ _publ_author_name 'Richard Oakley' 'Leanne Beer' 'Jaclyn L. Brusso' 'Robert C. Haddon' 'Mikhail E. Itkis' 'Robert W. Reed' ; J.F.Richardson ; 'Richard Secco' 'Xueyang Yu.' data_phet _database_code_depnum_ccdc_archive 'CCDC 281599' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common PhBPTSEt _chemical_melting_point ? _chemical_formula_moiety 'C13 H10 N3 S2 Se2' _chemical_formula_sum 'C13 H10 N3 S2 Se2' _chemical_formula_weight 430.28 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P3221 _symmetry_space_group_name_Hall P322 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z+2/3' '-x+y, -x, z+1/3' 'y, x, -z' 'x-y, -y, -z+1/3' '-x, -x+y, -z+2/3' _cell_length_a 15.733(6) _cell_length_b 15.733(6) _cell_length_c 4.973(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 1066.0(9) _cell_formula_units_Z 3 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 4519 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 26.9 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.311 _exptl_crystal_size_mid 0.046 _exptl_crystal_size_min 0.035 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.011 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 627 _exptl_absorpt_coefficient_mu 5.487 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.414 _exptl_absorpt_correction_T_max 0.825 _exptl_absorpt_process_details 'Sheldrick, G. M.; SADABS (1996)' _exptl_special_details ; Data were collected with a Bruker SMART APEX CCD-based diffractometer using /w-scans of width 0.3 deg. and 30s duration at a crystal-to-detector distance of 4.908 cm. Intensity decay over the course of the data collection was evaluated by recollecting the first 50 frames of data at the end of the experiment. No significant decay was noted. ; _diffrn_ambient_temperature 298(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 'Bruker SMART APEX' _diffrn_measurement_method /w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% <0.1 _diffrn_reflns_number 8442 _diffrn_reflns_av_R_equivalents 0.0542 _diffrn_reflns_av_sigmaI/netI 0.0410 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 6 _diffrn_reflns_theta_min 2.99 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1401 _reflns_number_gt 1338 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART 5.625 (Bruker, 2001)' _computing_cell_refinement 'SAINT 6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT 6.22 (Bruker, 2001)' _computing_structure_solution 'SHELXS-90 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL 6.12 (Bruker, 2001)' _computing_publication_material 'SHELXTL 6.12 (Bruker, 2001)' _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^)+(0.0493P)^2^+1.2839P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.08(3) _refine_ls_number_reflns 1401 _refine_ls_number_parameters 106 _refine_ls_number_restraints 14 _refine_ls_R_factor_all 0.0638 _refine_ls_R_factor_gt 0.0605 _refine_ls_wR_factor_ref 0.1254 _refine_ls_wR_factor_gt 0.1242 _refine_ls_goodness_of_fit_ref 1.329 _refine_ls_restrained_S_all 1.336 _refine_ls_shift/su_max 0.003 _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 Se1 Se 0.42328(7) 0.63565(7) 0.00717(17) 0.0473(3) Uani 1 1 d . . . S2 S 0.32424(16) 0.49022(17) -0.1844(5) 0.0477(6) Uani 1 1 d . . . C1 C 0.5131(6) 0.5813(6) -0.3405(19) 0.047(2) Uani 1 1 d . . . C2 C 0.4210(6) 0.4907(7) -0.3576(17) 0.0393(18) Uani 1 1 d . A . C3 C 0.4106(7) 0.4106(7) -0.5000 0.036(3) Uani 1 2 d S . . C4 C 0.6689(12) 0.6937(11) -0.584(4) 0.056(6) Uani 0.50 1 d PD A -1 C5 C 0.7538(16) 0.7140(18) -0.409(5) 0.075(8) Uani 0.50 1 d PD A -1 C6 C 0.3150(7) 0.3150(7) -0.5000 0.040(3) Uani 1 2 d S . . C7 C 0.2366(9) 0.3009(10) -0.649(3) 0.094(4) Uani 1 1 d U . . C8 C 0.1530(10) 0.2138(11) -0.655(3) 0.122(7) Uani 1 1 d . . . C9 C 0.1389(10) 0.1389(10) -0.5000 0.069(4) Uani 1 2 d S . . N1 N 0.5302(5) 0.6547(5) -0.1910(18) 0.054(2) Uani 1 1 d . A . N2 N 0.5831(11) 0.5951(11) -0.544(3) 0.035(4) Uani 0.50 1 d PDU A -1 H4A H 0.6497 0.7424 -0.5477 0.067 Uiso 0.50 1 calc PR A -1 H4B H 0.6893 0.7006 -0.7703 0.067 Uiso 0.50 1 calc PR A -1 H5A H 0.8092 0.7763 -0.4568 0.112 Uiso 0.50 1 calc PR A -1 H5B H 0.7702 0.6634 -0.4332 0.112 Uiso 0.50 1 calc PR A -1 H5C H 0.7369 0.7155 -0.2243 0.112 Uiso 0.50 1 calc PR A -1 H7 H 0.2410 0.3528 -0.7493 0.112 Uiso 1 1 calc R . . H8 H 0.1031 0.2057 -0.7708 0.146 Uiso 1 1 calc R . . H9 H 0.0772 0.0773 -0.5000 0.083 Uiso 1 2 d SR . . 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 Se1 0.0552(6) 0.0410(5) 0.0474(4) -0.0010(4) 0.0035(4) 0.0252(5) S2 0.0399(12) 0.0400(12) 0.0625(14) 0.0003(10) 0.0114(10) 0.0194(10) C3 0.029(4) 0.029(4) 0.046(7) 0.003(2) -0.003(2) 0.013(5) C2 0.036(4) 0.038(4) 0.045(5) 0.004(4) 0.002(3) 0.019(4) N1 0.040(5) 0.043(4) 0.064(5) -0.014(4) 0.007(4) 0.008(4) C1 0.038(5) 0.038(5) 0.053(5) -0.003(4) 0.008(4) 0.009(4) C6 0.028(4) 0.028(4) 0.064(8) -0.005(3) 0.005(3) 0.014(5) C7 0.077(7) 0.081(7) 0.099(7) 0.032(6) -0.025(6) 0.022(6) C8 0.060(8) 0.097(11) 0.160(15) 0.032(10) -0.063(9) 0.002(7) C9 0.054(6) 0.054(6) 0.082(11) 0.006(4) -0.006(4) 0.015(7) N2 0.038(7) 0.034(6) 0.022(9) 0.005(5) -0.007(6) 0.009(5) C4 0.050(13) 0.040(11) 0.052(14) 0.006(9) 0.026(9) 0.003(9) C5 0.063(15) 0.056(14) 0.10(2) -0.040(14) -0.009(14) 0.030(11) _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 Se1 N1 1.840(8) . ? Se1 S2 2.237(3) . ? S2 C2 1.745(9) . ? C3 C2 1.383(10) . ? C3 C2 1.383(10) 4_554 ? C3 C6 1.503(16) . ? C2 C1 1.440(12) . ? N1 C1 1.284(12) . ? C1 N2 1.40(3) 4_554 ? C1 N2 1.43(2) . ? C6 C7 1.358(13) . ? C6 C7 1.358(13) 4_554 ? C7 C8 1.344(18) . ? C7 H7 0.9300 . ? C8 C9 1.330(16) . ? C8 H8 0.9300 . ? C9 C8 1.330(16) 4_554 ? C9 H9 0.9704 . ? N2 C1 1.40(3) 4_554 ? N2 C4 1.475(9) . ? C4 C5 1.488(10) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Se1 S2 92.9(2) . . ? C2 S2 Se1 92.6(3) . . ? C2 C3 C2 118.0(11) . 4_554 ? C2 C3 C6 121.0(5) . . ? C2 C3 C6 121.0(5) 4_554 . ? C3 C2 C1 122.3(9) . . ? C3 C2 S2 122.9(7) . . ? C1 C2 S2 114.8(7) . . ? C1 N1 Se1 113.6(6) . . ? N1 C1 N2 116.4(9) . 4_554 ? N1 C1 N2 118.4(9) . . ? N1 C1 C2 125.3(8) . . ? N2 C1 C2 117.2(10) 4_554 . ? N2 C1 C2 115.2(9) . . ? C7 C6 C7 115.2(14) . 4_554 ? C7 C6 C3 122.4(7) . . ? C7 C6 C3 122.4(7) 4_554 . ? C8 C7 C6 121.7(12) . . ? C8 C7 H7 119.2 . . ? C6 C7 H7 119.2 . . ? C9 C8 C7 122.3(13) . . ? C9 C8 H8 118.8 . . ? C7 C8 H8 118.8 . . ? C8 C9 C8 116.5(16) 4_554 . ? C8 C9 H9 121.8 4_554 . ? C8 C9 H9 121.7 . . ? C1 N2 C1 119.5(10) 4_554 . ? C1 N2 C4 120.0(19) 4_554 . ? C1 N2 C4 119.0(18) . . ? N2 C4 C5 113.5(14) . . ? N2 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N2 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? 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 N1 Se1 S2 C2 6.4(4) . . . . ? C2 C3 C2 C1 -3.8(7) 4_554 . . . ? C6 C3 C2 C1 176.2(7) . . . . ? C2 C3 C2 S2 176.4(8) 4_554 . . . ? C6 C3 C2 S2 -3.6(8) . . . . ? Se1 S2 C2 C3 171.8(6) . . . . ? Se1 S2 C2 C1 -7.9(7) . . . . ? S2 Se1 N1 C1 -4.4(8) . . . . ? Se1 N1 C1 N2 -168.2(8) . . . 4_554 ? Se1 N1 C1 N2 166.9(9) . . . . ? Se1 N1 C1 C2 -0.5(14) . . . . ? C3 C2 C1 N1 -172.7(8) . . . . ? S2 C2 C1 N1 7.1(14) . . . . ? C3 C2 C1 N2 -5.1(14) . . . 4_554 ? S2 C2 C1 N2 174.7(8) . . . 4_554 ? C3 C2 C1 N2 19.5(14) . . . . ? S2 C2 C1 N2 -160.7(9) . . . . ? C2 C3 C6 C7 76.9(9) . . . . ? C2 C3 C6 C7 -103.1(9) 4_554 . . . ? C2 C3 C6 C7 -103.1(9) . . . 4_554 ? C2 C3 C6 C7 76.9(9) 4_554 . . 4_554 ? C7 C6 C7 C8 -2.6(15) 4_554 . . . ? C3 C6 C7 C8 177.4(15) . . . . ? C6 C7 C8 C9 5(3) . . . . ? C7 C8 C9 C8 -2.6(15) . . . 4_554 ? N1 C1 N2 C1 162.9(13) . . . 4_554 ? N2 C1 N2 C1 72(3) 4_554 . . 4_554 ? C2 C1 N2 C1 -28.4(13) . . . 4_554 ? N1 C1 N2 C4 -3.3(19) . . . . ? N2 C1 N2 C4 -94(2) 4_554 . . . ? C2 C1 N2 C4 165.4(12) . . . . ? C1 N2 C4 C5 -78.5(19) 4_554 . . . ? C1 N2 C4 C5 88(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.737 _refine_diff_density_min -0.825 _refine_diff_density_rms 0.125