# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Richard Oakley' 'Leanne Beer' 'Jaclyn L. Brusso' 'Robert C. Haddon' 'Mikhail E. Itkis' 'Alicea A. Leitch' 'Robert W. Reed' 'John F. Richardson' _publ_contact_author_name 'Prof 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_requested_journal 'Chemical Communications' _publ_section_title ; Selenium based neutral radical conductors ; data_rto07rt _database_code_depnum_ccdc_archive 'CCDC 254578' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common HBPTSH+ _chemical_melting_point ? _chemical_formula_moiety 'C5 H2 N3 S2 Se2, F6 Sb' _chemical_formula_sum 'C5 H2 F6 N3 S2 Sb Se2' _chemical_formula_weight 561.89 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' F F 0.0171 0.0103 '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' Sb Sb -0.5866 1.5461 '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 Orthorhombic _symmetry_space_group_name_H-M Pnma _symmetry_space_group_name_Hall -P2ac2n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 10.778(2) _cell_length_b 14.142(3) _cell_length_c 8.4526(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1288.4(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 3330 _cell_measurement_theta_min 2.808 _cell_measurement_theta_max 26.649 _exptl_crystal_description plate _exptl_crystal_colour gold _exptl_crystal_size_max 0.193 _exptl_crystal_size_mid 0.099 _exptl_crystal_size_min 0.028 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.897 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1032 _exptl_absorpt_coefficient_mu 8.175 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.575 _exptl_absorpt_correction_T_max 0.80 _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 295(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 11268 _diffrn_reflns_av_R_equivalents 0.0401 _diffrn_reflns_av_sigmaI/netI 0.0358 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 28.27 _reflns_number_total 1666 _reflns_number_gt 1258 _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^)+(0.0088P)^2^+3.6017P] 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 0.0 _refine_ls_number_reflns 1666 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0607 _refine_ls_R_factor_gt 0.0380 _refine_ls_wR_factor_ref 0.0777 _refine_ls_wR_factor_gt 0.0729 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.165 _refine_ls_shift/su_max 0.001 _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 0.84923(5) 0.52021(4) 0.59485(7) 0.05483(18) Uani 1 1 d . . . S1 S 0.67967(12) 0.44173(11) 0.65878(19) 0.0555(4) Uani 1 1 d . . . N1 N 0.9327(4) 0.4138(3) 0.5507(5) 0.0460(10) Uani 1 1 d . . . N2 N 0.9285(5) 0.2500 0.5484(7) 0.0425(15) Uani 1 2 d S . . C1 C 0.7435(4) 0.3337(4) 0.6272(5) 0.0401(11) Uani 1 1 d . . . C2 C 0.8721(4) 0.3353(4) 0.5734(5) 0.0376(10) Uani 1 1 d . . . C3 C 0.6818(6) 0.2500 0.6494(9) 0.0433(17) Uani 1 2 d S . . H2 H 0.999(8) 0.2500 0.522(10) 0.07(3) Uiso 1 2 d S . . H3 H 0.610(8) 0.2500 0.670(10) 0.06(3) Uiso 1 2 d S . . Sb Sb 0.86369(4) 0.2500 0.08983(6) 0.04274(15) Uani 1 2 d S . . F1 F 0.7011(4) 0.2500 0.0085(5) 0.0591(12) Uani 1 2 d S . . F2 F 0.9079(3) 0.3424(3) -0.0578(4) 0.0685(9) Uani 1 1 d . . . F3 F 1.0226(4) 0.2500 0.1771(6) 0.0691(14) Uani 1 2 d S . . F4 F 0.8164(3) 0.3443(2) 0.2321(4) 0.0644(9) Uani 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 Se1 0.0433(3) 0.0556(4) 0.0655(4) -0.0028(3) 0.0066(3) 0.0031(2) S1 0.0387(7) 0.0568(9) 0.0709(10) -0.0011(8) 0.0132(7) 0.0068(6) N1 0.038(2) 0.050(3) 0.050(3) -0.006(2) 0.0015(18) 0.0019(19) N2 0.026(3) 0.051(4) 0.051(4) 0.000 0.007(3) 0.000 C1 0.036(2) 0.052(3) 0.032(2) 0.000(2) 0.0003(19) 0.004(2) C2 0.027(2) 0.055(3) 0.031(2) -0.002(2) -0.0026(19) 0.002(2) C3 0.026(3) 0.054(5) 0.049(4) 0.000 0.002(3) 0.000 Sb 0.0355(2) 0.0534(3) 0.0393(3) 0.000 -0.0067(2) 0.000 F1 0.034(2) 0.087(3) 0.056(3) 0.000 -0.010(2) 0.000 F2 0.065(2) 0.078(2) 0.063(2) 0.0220(19) -0.0017(17) -0.0110(18) F3 0.044(2) 0.088(4) 0.075(3) 0.000 -0.024(2) 0.000 F4 0.075(2) 0.064(2) 0.0546(19) -0.0121(17) -0.0141(17) 0.0121(17) _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 1.793(4) . no Se1 S1 2.2054(15) . no S1 C1 1.697(5) . no N1 C2 1.301(6) . no N2 C2 1.368(5) 7_565 no N2 C2 1.368(5) . no N2 H2 0.79(9) . no C1 C3 1.371(6) . no C1 C2 1.459(6) . no C3 C1 1.371(6) 7_565 no C3 H3 0.80(8) . no Sb F3 1.865(4) . no Sb F4 1.867(3) 7_565 no Sb F4 1.867(3) . no Sb F2 1.869(3) 7_565 no Sb F2 1.869(3) . no Sb F1 1.883(4) . 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_3 _geom_angle_publ_flag N1 Se1 S1 92.53(14) . . no C1 S1 Se1 94.51(17) . . no C2 N1 Se1 115.7(3) . . no C2 N2 C2 123.9(6) 7_565 . no C2 N2 H2 118.0(3) 7_565 . no C2 N2 H2 118.0(3) . . no C3 C1 C2 121.2(5) . . no C3 C1 S1 124.0(4) . . no C2 C1 S1 114.8(4) . . no N1 C2 N2 120.4(4) . . no N1 C2 C1 122.4(5) . . no N2 C2 C1 117.1(5) . . no C1 C3 C1 119.4(6) . 7_565 no C1 C3 H3 120.2(4) . . no C1 C3 H3 120.2(4) 7_565 . no F3 Sb F4 89.78(15) . 7_565 no F3 Sb F4 89.78(15) . . no F4 Sb F4 91.2(2) 7_565 . no F3 Sb F2 91.71(15) . 7_565 no F4 Sb F2 90.01(16) 7_565 7_565 no F4 Sb F2 178.07(15) . 7_565 no F3 Sb F2 91.71(15) . . no F4 Sb F2 178.07(15) 7_565 . no F4 Sb F2 90.01(16) . . no F2 Sb F2 88.7(2) 7_565 . no F3 Sb F1 178.1(2) . . no F4 Sb F1 88.90(14) 7_565 . no F4 Sb F1 88.90(14) . . no F2 Sb F1 89.64(14) 7_565 . no F2 Sb F1 89.64(14) . . 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 N1 Se1 S1 C1 1.2(2) . . . . no S1 Se1 N1 C2 -1.7(4) . . . . no Se1 S1 C1 C3 179.2(5) . . . . no Se1 S1 C1 C2 -0.7(3) . . . . no Se1 N1 C2 N2 -177.8(4) . . . . no Se1 N1 C2 C1 1.6(6) . . . . no C2 N2 C2 N1 178.3(4) 7_565 . . . no C2 N2 C2 C1 -1.2(9) 7_565 . . . no C3 C1 C2 N1 179.7(5) . . . . no S1 C1 C2 N1 -0.4(6) . . . . no C3 C1 C2 N2 -0.8(8) . . . . no S1 C1 C2 N2 179.1(4) . . . . no C2 C1 C3 C1 2.7(10) . . . 7_565 no S1 C1 C3 C1 -177.2(4) . . . 7_565 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 F1 0.79(9) 2.19(9) 2.977(7) 170(9) 6_656 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.554 _refine_diff_density_min -0.475 _refine_diff_density_rms 0.110 #===================================== data_rto09brt _database_code_depnum_ccdc_archive 'CCDC 254579' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common HBPTSEt _chemical_melting_point ? _chemical_formula_moiety 'C14 H12 N6 S4 Se4' _chemical_formula_sum 'C7 H6 N3 S2 Se2' _chemical_formula_weight 354.19 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 Monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall -P2ybc 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 4.8546(8) _cell_length_b 12.692(2) _cell_length_c 16.472(3) _cell_angle_alpha 90.00 _cell_angle_beta 97.624(3) _cell_angle_gamma 90.00 _cell_volume 1005.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 4150 _cell_measurement_theta_min 2.545 _cell_measurement_theta_max 28.066 _exptl_crystal_description needle _exptl_crystal_colour black _exptl_crystal_size_max 0.213 _exptl_crystal_size_mid 0.093 _exptl_crystal_size_min 0.072 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.339 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 676 _exptl_absorpt_coefficient_mu 7.725 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.684 _exptl_absorpt_correction_T_max 1.000 _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 295(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 8674 _diffrn_reflns_av_R_equivalents 0.0273 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.03 _diffrn_reflns_theta_max 28.07 _reflns_number_total 2379 _reflns_number_gt 1854 _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^)+(0.0419P)^2^+0.0000P] 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 0.0 _refine_ls_number_reflns 2379 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0280 _refine_ls_wR_factor_ref 0.0726 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _refine_ls_shift/su_max 0.001 _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 0.36682(6) 0.98669(2) 0.37946(2) 0.03208(11) Uani 1 1 d . . . Se2 Se 1.41274(7) 0.51280(2) 0.42701(2) 0.03663(11) Uani 1 1 d . . . S1 S 0.36665(15) 0.88054(6) 0.27276(5) 0.03269(19) Uani 1 1 d . . . S2 S 1.10185(16) 0.55986(6) 0.27694(5) 0.03375(19) Uani 1 1 d . . . N1 N 0.6432(5) 0.91341(19) 0.44004(15) 0.0303(6) Uani 1 1 d . . . N2 N 0.9590(5) 0.77574(19) 0.44169(14) 0.0273(5) Uani 1 1 d . . . N3 N 1.2446(5) 0.63197(19) 0.45568(14) 0.0303(6) Uani 1 1 d . . . C1 C 0.6259(5) 0.8015(2) 0.32086(17) 0.0242(6) Uani 1 1 d . . . C2 C 0.7398(6) 0.8335(2) 0.40294(16) 0.0251(6) Uani 1 1 d . . . C3 C 1.0624(6) 0.6842(2) 0.40777(17) 0.0259(6) Uani 1 1 d . . . C4 C 0.9498(5) 0.6576(2) 0.32336(16) 0.0257(6) Uani 1 1 d . . . C5 C 0.7230(6) 0.7153(2) 0.28476(17) 0.0290(6) Uani 1 1 d . . . H5 H 0.6375 0.6941 0.2335 0.035 Uiso 1 1 calc R . . C6 C 1.0872(6) 0.8092(2) 0.52410(17) 0.0322(7) Uani 1 1 d . . . H6A H 1.0595 0.8843 0.5302 0.039 Uiso 1 1 calc R . . H6B H 1.2856 0.7961 0.5297 0.039 Uiso 1 1 calc R . . C7 C 0.9652(8) 0.7516(3) 0.59062(19) 0.0475(9) Uani 1 1 d . . . H7A H 0.7677 0.7623 0.5840 0.071 Uiso 1 1 calc R . . H7B H 1.0456 0.7781 0.6430 0.071 Uiso 1 1 calc R . . H7C H 1.0044 0.6777 0.5873 0.071 Uiso 1 1 calc R . . 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 0.03234(18) 0.02531(17) 0.0369(2) 0.00185(13) -0.00156(13) 0.00593(12) Se2 0.0418(2) 0.02698(19) 0.0398(2) -0.00235(14) 0.00052(15) 0.00973(13) S1 0.0330(4) 0.0327(4) 0.0298(4) 0.0028(3) -0.0054(3) 0.0057(3) S2 0.0366(4) 0.0313(4) 0.0324(4) -0.0084(3) 0.0010(3) 0.0047(3) N1 0.0327(14) 0.0272(13) 0.0287(13) -0.0007(11) -0.0043(10) 0.0069(11) N2 0.0321(13) 0.0243(13) 0.0233(12) 0.0001(10) -0.0050(9) 0.0056(10) N3 0.0363(14) 0.0243(13) 0.0285(13) -0.0012(11) -0.0021(11) 0.0091(11) C1 0.0222(14) 0.0258(15) 0.0236(14) 0.0034(11) -0.0010(11) -0.0009(11) C2 0.0290(15) 0.0223(15) 0.0228(15) 0.0020(12) -0.0005(11) 0.0001(12) C3 0.0294(15) 0.0233(15) 0.0247(15) 0.0002(12) 0.0022(12) 0.0012(12) C4 0.0272(15) 0.0250(15) 0.0248(15) -0.0006(12) 0.0035(11) -0.0038(12) C5 0.0319(16) 0.0330(16) 0.0211(14) -0.0019(12) -0.0001(12) -0.0025(13) C6 0.0373(17) 0.0287(17) 0.0274(16) -0.0059(13) -0.0073(13) 0.0062(13) C7 0.061(2) 0.049(2) 0.0319(18) -0.0002(17) 0.0029(15) 0.0062(17) _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 1.818(2) . no Se1 S1 2.2145(9) . no Se2 N3 1.811(2) . no Se2 Se2 2.4628(8) 3_866 no Se2 S2 2.7847(9) . no S1 C1 1.719(3) . no S2 C4 1.679(3) . no N1 C2 1.303(4) . no N2 C2 1.377(3) . no N2 C3 1.410(4) . no N2 C6 1.479(4) . no N3 C3 1.288(3) . no C1 C5 1.359(4) . no C1 C2 1.449(4) . no C3 C4 1.464(4) . no C4 C5 1.402(4) . no C5 H5 0.9300 . no C6 C7 1.502(4) . no C6 H6A 0.9700 . no C6 H6B 0.9700 . no C7 H7A 0.9600 . no C7 H7B 0.9600 . no C7 H7C 0.9600 . 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_3 _geom_angle_publ_flag N1 Se1 S1 92.69(8) . . no N3 Se2 Se2 87.94(7) . 3_866 no N3 Se2 S2 80.93(8) . . no Se2 Se2 S2 166.10(3) 3_866 . no C1 S1 Se1 93.79(10) . . no C4 S2 Se2 88.48(10) . . no C2 N1 Se1 115.21(19) . . no C2 N2 C3 123.3(2) . . no C2 N2 C6 118.5(2) . . no C3 N2 C6 118.2(2) . . no C3 N3 Se2 124.5(2) . . no C5 C1 C2 121.5(3) . . no C5 C1 S1 122.9(2) . . no C2 C1 S1 115.6(2) . . no N1 C2 N2 120.1(2) . . no N1 C2 C1 122.6(2) . . no N2 C2 C1 117.3(2) . . no N3 C3 N2 115.7(2) . . no N3 C3 C4 127.0(3) . . no N2 C3 C4 117.3(2) . . no C5 C4 C3 118.8(3) . . no C5 C4 S2 123.0(2) . . no C3 C4 S2 118.1(2) . . no C1 C5 C4 121.3(3) . . no C1 C5 H5 119.4 . . no C4 C5 H5 119.4 . . no N2 C6 C7 111.8(3) . . no N2 C6 H6A 109.3 . . no C7 C6 H6A 109.3 . . no N2 C6 H6B 109.3 . . no C7 C6 H6B 109.3 . . no H6A C6 H6B 107.9 . . no C6 C7 H7A 109.5 . . no C6 C7 H7B 109.5 . . no H7A C7 H7B 109.5 . . no C6 C7 H7C 109.5 . . no H7A C7 H7C 109.5 . . no H7B C7 H7C 109.5 . . 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 N1 Se1 S1 C1 0.41(12) . . . . no N3 Se2 S2 C4 -6.50(12) . . . . no Se2 Se2 S2 C4 30.72(16) 3_866 . . . no S1 Se1 N1 C2 1.3(2) . . . . no Se2 Se2 N3 C3 -168.1(2) 3_866 . . . no S2 Se2 N3 C3 3.5(2) . . . . no Se1 S1 C1 C5 179.0(2) . . . . no Se1 S1 C1 C2 -2.0(2) . . . . no Se1 N1 C2 N2 176.7(2) . . . . no Se1 N1 C2 C1 -3.2(4) . . . . no C3 N2 C2 N1 175.6(3) . . . . no C6 N2 C2 N1 -2.5(4) . . . . no C3 N2 C2 C1 -4.5(4) . . . . no C6 N2 C2 C1 177.5(2) . . . . no C5 C1 C2 N1 -177.3(3) . . . . no S1 C1 C2 N1 3.7(4) . . . . no C5 C1 C2 N2 2.7(4) . . . . no S1 C1 C2 N2 -176.3(2) . . . . no Se2 N3 C3 N2 -179.27(19) . . . . no Se2 N3 C3 C4 1.9(4) . . . . no C2 N2 C3 N3 -171.7(3) . . . . no C6 N2 C3 N3 6.3(4) . . . . no C2 N2 C3 C4 7.2(4) . . . . no C6 N2 C3 C4 -174.7(2) . . . . no N3 C3 C4 C5 170.6(3) . . . . no N2 C3 C4 C5 -8.2(4) . . . . no N3 C3 C4 S2 -10.1(4) . . . . no N2 C3 C4 S2 171.1(2) . . . . no Se2 S2 C4 C5 -171.8(2) . . . . no Se2 S2 C4 C3 8.9(2) . . . . no C2 C1 C5 C4 -4.2(4) . . . . no S1 C1 C5 C4 174.8(2) . . . . no C3 C4 C5 C1 6.9(4) . . . . no S2 C4 C5 C1 -172.3(2) . . . . no C2 N2 C6 C7 94.6(3) . . . . no C3 N2 C6 C7 -83.6(3) . . . . no _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 28.07 _diffrn_measured_fraction_theta_full 0.973 _refine_diff_density_max 1.057 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.099