# Supplementary Material (ESI) for Dalton Transactions # This journal is (c) The Royal Society of Chemistry 2008 data_global _journal_name_full 'Dalton Trans.' _journal_coden_Cambridge 0222 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Konstantin Shuvaev' _publ_contact_author_email KSHUVAEV@MUN.CA _publ_section_title ; NC-(CF2)4-CNSSN* Containing 1,2,3,5-Dithiadiazolyl Radical Dimer Exhibiting Triplet Excited States at Low Temperature and Thermal Hysteresis on Melting - Solidification: Structural, Spectroscopic, and Magnetic Characterization ; loop_ _publ_author_name 'Konstantin Shuvaev' 'Tareque S M Abedin' 'Andreas Decken' 'Friedrich Grein' 'Jack Passmore' ; L.K.Thompson ; # Attachment 'NCC4F8CNSSN1.cif' data_jp050496 _database_code_depnum_ccdc_archive 'CCDC 682306' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 F8 N3 S2' _chemical_formula_weight 330.21 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' 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8686(11) _cell_length_b 8.2860(17) _cell_length_c 11.513(2) _cell_angle_alpha 110.834(3) _cell_angle_beta 99.201(4) _cell_angle_gamma 91.178(4) _cell_volume 514.69(18) _cell_formula_units_Z 2 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 1914 _cell_measurement_theta_min 2.6395 _cell_measurement_theta_max 27.8835 _exptl_crystal_description Irregular _exptl_crystal_colour Red _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.131 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 322 _exptl_absorpt_coefficient_mu 0.623 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7668 _exptl_absorpt_correction_T_max 0.9695 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997b)' _exptl_special_details ; Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_source_type K760 _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 3509 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_sigmaI/netI 0.0238 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 27.47 _reflns_number_total 2228 _reflns_number_gt 1851 _reflns_threshold_expression 'I > 2\s(I)' _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0831P)^2^+0.0700P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2228 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0505 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1206 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.079 _refine_ls_restrained_S_all 1.079 _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 S1 S 0.52726(9) 0.77206(7) 0.52338(5) 0.03294(19) Uani 1 1 d . . . S2 S 0.22097(9) 0.65743(7) 0.54339(5) 0.03111(18) Uani 1 1 d . . . N3 N 0.3459(3) 0.5961(2) 0.65660(15) 0.0283(4) Uani 1 1 d . . . C4 C 0.5726(3) 0.6490(3) 0.69208(18) 0.0239(4) Uani 1 1 d . . . N5 N 0.6895(3) 0.7310(2) 0.63719(16) 0.0295(4) Uani 1 1 d . . . C6 C 0.7044(3) 0.6124(3) 0.80429(18) 0.0254(4) Uani 1 1 d . . . C7 C 0.6751(3) 0.7541(3) 0.93115(18) 0.0218(4) Uani 1 1 d . . . C8 C 0.8240(3) 0.7428(3) 1.05195(18) 0.0229(4) Uani 1 1 d . . . C9 C 0.7823(4) 0.8794(3) 1.17823(19) 0.0273(4) Uani 1 1 d . . . C10 C 0.9481(4) 0.8615(3) 1.2855(2) 0.0340(5) Uani 1 1 d . . . N11 N 1.0756(4) 0.8440(3) 1.3641(2) 0.0487(6) Uani 1 1 d . . . F1 F 0.6246(3) 0.45796(16) 0.80307(12) 0.0369(3) Uani 1 1 d . . . F2 F 0.9307(2) 0.60702(19) 0.79855(12) 0.0362(3) Uani 1 1 d . . . F3 F 0.4511(2) 0.74566(17) 0.94199(11) 0.0322(3) Uani 1 1 d . . . F4 F 0.7312(2) 0.90891(15) 0.92531(11) 0.0329(3) Uani 1 1 d . . . F5 F 0.7785(2) 0.58564(15) 1.05658(12) 0.0322(3) Uani 1 1 d . . . F6 F 1.0492(2) 0.76391(17) 1.04826(11) 0.0322(3) Uani 1 1 d . . . F7 F 0.5660(2) 0.8582(2) 1.19549(12) 0.0406(4) Uani 1 1 d . . . F8 F 0.8174(3) 1.03913(16) 1.17741(12) 0.0388(3) 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 S1 0.0387(3) 0.0361(3) 0.0217(3) 0.0107(2) -0.0011(2) -0.0020(2) S2 0.0286(3) 0.0387(3) 0.0205(3) 0.0057(2) 0.0004(2) 0.0026(2) N3 0.0300(9) 0.0360(10) 0.0161(8) 0.0061(7) 0.0038(7) 0.0046(7) C4 0.0288(10) 0.0224(9) 0.0148(9) 0.0006(7) 0.0021(7) 0.0026(7) N5 0.0320(9) 0.0335(10) 0.0193(9) 0.0078(7) -0.0008(7) -0.0025(7) C6 0.0319(10) 0.0241(10) 0.0169(9) 0.0036(8) 0.0032(7) 0.0054(8) C7 0.0248(9) 0.0213(10) 0.0167(9) 0.0043(7) 0.0024(7) 0.0035(7) C8 0.0260(9) 0.0219(10) 0.0176(9) 0.0043(8) 0.0016(7) 0.0033(7) C9 0.0335(10) 0.0256(10) 0.0176(10) 0.0031(8) 0.0011(8) 0.0056(8) C10 0.0444(12) 0.0342(12) 0.0171(10) 0.0032(9) 0.0013(9) 0.0070(9) N11 0.0640(14) 0.0492(13) 0.0254(11) 0.0105(9) -0.0065(9) 0.0101(11) F1 0.0612(9) 0.0192(6) 0.0239(7) 0.0033(5) 0.0010(6) 0.0004(6) F2 0.0308(7) 0.0532(8) 0.0222(6) 0.0093(6) 0.0069(5) 0.0163(6) F3 0.0244(6) 0.0464(8) 0.0219(6) 0.0076(6) 0.0041(5) 0.0071(5) F4 0.0522(8) 0.0213(6) 0.0223(6) 0.0066(5) 0.0020(5) 0.0008(5) F5 0.0479(7) 0.0217(6) 0.0252(6) 0.0079(5) 0.0030(5) 0.0028(5) F6 0.0238(6) 0.0414(8) 0.0254(6) 0.0060(5) 0.0018(5) 0.0030(5) F7 0.0364(7) 0.0551(9) 0.0245(7) 0.0054(6) 0.0097(5) 0.0079(6) F8 0.0624(9) 0.0230(7) 0.0223(7) 0.0010(5) -0.0005(6) 0.0052(6) _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 S1 N5 1.6343(18) . ? S1 S2 2.0986(8) . ? S2 N3 1.6358(18) . ? N3 C4 1.343(3) . ? C4 N5 1.325(3) . ? C4 C6 1.526(3) . ? C6 F2 1.341(2) . ? C6 F1 1.348(2) . ? C6 C7 1.552(3) . ? C7 F3 1.343(2) . ? C7 F4 1.345(2) . ? C7 C8 1.554(3) . ? C8 F6 1.339(2) . ? C8 F5 1.345(2) . ? C8 C9 1.552(3) . ? C9 F7 1.334(3) . ? C9 F8 1.339(2) . ? C9 C10 1.498(3) . ? C10 N11 1.132(3) . ? 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 N5 S1 S2 94.49(7) . . ? N3 S2 S1 94.85(7) . . ? C4 N3 S2 112.42(15) . . ? N5 C4 N3 124.85(18) . . ? N5 C4 C6 117.78(17) . . ? N3 C4 C6 117.37(18) . . ? C4 N5 S1 113.25(14) . . ? F2 C6 F1 108.08(16) . . ? F2 C6 C4 110.35(16) . . ? F1 C6 C4 110.20(16) . . ? F2 C6 C7 108.78(15) . . ? F1 C6 C7 108.27(16) . . ? C4 C6 C7 111.08(16) . . ? F3 C7 F4 108.54(15) . . ? F3 C7 C6 108.23(15) . . ? F4 C7 C6 107.58(16) . . ? F3 C7 C8 108.34(16) . . ? F4 C7 C8 108.08(15) . . ? C6 C7 C8 115.88(16) . . ? F6 C8 F5 108.88(15) . . ? F6 C8 C9 106.76(15) . . ? F5 C8 C9 107.13(16) . . ? F6 C8 C7 109.74(16) . . ? F5 C8 C7 109.08(15) . . ? C9 C8 C7 115.07(16) . . ? F7 C9 F8 108.37(17) . . ? F7 C9 C10 109.19(18) . . ? F8 C9 C10 109.03(17) . . ? F7 C9 C8 111.04(17) . . ? F8 C9 C8 109.89(17) . . ? C10 C9 C8 109.29(17) . . ? N11 C10 C9 178.0(2) . . ? _diffrn_measured_fraction_theta_max 0.943 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.503 _refine_diff_density_min -0.383 _refine_diff_density_rms 0.113