# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 # Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_publication_text _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _publ_contact_author_name 'Richard T. Oakley' _publ_contact_author_address ;Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada ; _publ_contact_author_email oakley@uwaterloo.ca _publ_contact_author_phone 1-519-888-4582 _publ_contact_author_fax 1-519-746-0435 _publ_section_title ;Hybrid dithiazolothiadiazinyl radicals; versatile building blocks for magnetic and conductive materials ; loop_ _publ_author_name _publ_author_address 'Stephen M. Winter' ;Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada ; 'Aidin R. Balo' ;Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada ; 'Ryan J. Roberts' ;Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada ; 'Kristina Lekin' ;Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada ; 'Abdeljalil Assoud' ;Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada ; 'Paul A. Dube' ;Brockhouse Institute for Materials Research, McMaster University, Hamilton, Ontario L8S 4M1, Canada ; 'Richard T. Oakley' ;Department of Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada ; data_twin5 _database_code_depnum_ccdc_archive 'CCDC 912363' #TrackingRef '3b.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 N4 S3' _chemical_formula_sum 'C13 H9 N4 S3' _chemical_formula_weight 317.42 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 'Triclinic' _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.9154(15) _cell_length_b 9.5271(19) _cell_length_c 10.1385(17) _cell_angle_alpha 86.286(13) _cell_angle_beta 89.883(14) _cell_angle_gamma 78.867(14) _cell_volume 654.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 427 _cell_measurement_theta_min 3 _cell_measurement_theta_max 60 _exptl_crystal_description 'plate' _exptl_crystal_colour 'black-red' _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 326 _exptl_absorpt_coefficient_mu 0.560 _exptl_absorpt_correction_type 'empirical' _exptl_absorpt_correction_T_min 0.8963 _exptl_absorpt_correction_T_max 0.9972 _exptl_absorpt_process_details 'twinabs' _exptl_special_details ; ‘details of twinning from .abs file’ ‘BASF w/esd from .lst file’ ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6122 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 26.40 _reflns_number_total 2664 _reflns_number_gt 2833 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'ApexII' _computing_cell_refinement 'ApexII' _computing_data_reduction 'ApexII' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0110P)^2^+0.0897P] 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 SHELXL _refine_ls_extinction_coef 0.0022(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4697 _refine_ls_number_parameters 183 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1243 _refine_ls_R_factor_gt 0.0712 _refine_ls_wR_factor_ref 0.1422 _refine_ls_wR_factor_gt 0.1325 _refine_ls_goodness_of_fit_ref 1.619 _refine_ls_restrained_S_all 1.619 _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 0.18652(19) 0.77225(12) 1.03038(10) 0.0668(4) Uani 1 1 d . . . S2 S 0.14342(17) 0.93225(11) 0.87480(10) 0.0570(3) Uani 1 1 d . . . S3 S 0.1669(2) 0.74750(12) 0.37292(10) 0.0685(4) Uani 1 1 d . . . N1 N 0.2265(5) 0.6296(3) 0.9426(3) 0.0604(10) Uani 1 1 d . . . N2 N 0.2448(5) 0.5486(3) 0.7316(3) 0.0514(9) Uani 1 1 d . . . N3 N 0.2607(5) 0.4583(3) 0.5265(3) 0.0487(8) Uani 1 1 d . . . N4 N 0.2120(5) 0.5872(3) 0.3126(3) 0.0577(9) Uani 1 1 d . . . C1 C 0.2152(6) 0.6613(4) 0.8152(4) 0.0468(10) Uani 1 1 d . . . C2 C 0.1730(6) 0.8049(4) 0.7585(4) 0.0467(10) Uani 1 1 d . . . C3 C 0.1621(6) 0.8319(4) 0.6247(4) 0.0522(10) Uani 1 1 d . . . H3 H 0.1386 0.9258 0.5882 0.063 Uiso 1 1 calc R . . C4 C 0.1863(6) 0.7190(4) 0.5439(4) 0.0456(10) Uani 1 1 d . . . C5 C 0.2310(5) 0.5731(4) 0.5965(3) 0.0435(10) Uani 1 1 d . . . C6 C 0.2887(7) 0.4007(4) 0.7922(4) 0.0709(14) Uani 1 1 d . . . H6C H 0.3058 0.3341 0.7239 0.106 Uiso 1 1 calc R . . H6B H 0.1815 0.3845 0.8477 0.106 Uiso 1 1 calc R . . H6A H 0.4074 0.3871 0.8443 0.106 Uiso 1 1 calc R . . C7 C 0.2491(6) 0.4715(4) 0.3909(4) 0.0473(10) Uani 1 1 d . . . C8 C 0.2884(6) 0.3326(4) 0.3249(4) 0.0466(10) Uani 1 1 d . . . C9 C 0.2849(6) 0.3294(4) 0.1886(4) 0.0528(11) Uani 1 1 d . . . H9 H 0.2581 0.4146 0.1358 0.063 Uiso 1 1 calc R . . C10 C 0.3213(6) 0.1995(4) 0.1311(4) 0.0597(12) Uani 1 1 d . . . H10 H 0.3188 0.1978 0.0395 0.072 Uiso 1 1 calc R . . C11 C 0.3612(6) 0.0726(4) 0.2077(4) 0.0577(11) Uani 1 1 d . . . H11 H 0.3854 -0.0145 0.1684 0.069 Uiso 1 1 calc R . . C12 C 0.3650(6) 0.0760(4) 0.3427(4) 0.0562(11) Uani 1 1 d . . . H12 H 0.3934 -0.0096 0.3947 0.067 Uiso 1 1 calc R . . C13 C 0.3271(6) 0.2051(4) 0.4030(4) 0.0538(11) Uani 1 1 d . . . H13 H 0.3276 0.2060 0.4946 0.065 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 S1 0.0882(9) 0.0601(7) 0.0489(6) -0.0129(5) -0.0022(6) -0.0037(6) S2 0.0666(8) 0.0524(7) 0.0521(6) -0.0178(5) 0.0027(5) -0.0070(5) S3 0.1154(10) 0.0429(6) 0.0447(6) -0.0026(5) -0.0023(6) -0.0093(6) N1 0.078(3) 0.054(2) 0.048(2) -0.0118(16) 0.0030(19) -0.0049(19) N2 0.063(2) 0.043(2) 0.046(2) -0.0046(15) -0.0054(17) -0.0041(17) N3 0.061(2) 0.0365(18) 0.0478(19) -0.0068(14) 0.0014(17) -0.0069(16) N4 0.084(3) 0.0319(19) 0.058(2) -0.0075(15) 0.0036(19) -0.0099(18) C1 0.052(3) 0.045(2) 0.043(2) -0.0118(19) 0.005(2) -0.007(2) C2 0.046(2) 0.047(2) 0.048(2) -0.0093(18) 0.0003(19) -0.0066(19) C3 0.056(3) 0.047(2) 0.052(2) -0.0004(18) 0.004(2) -0.008(2) C4 0.050(3) 0.034(2) 0.051(2) -0.0095(18) 0.002(2) -0.0041(19) C5 0.042(2) 0.047(2) 0.043(2) -0.0075(18) 0.0035(18) -0.0095(19) C6 0.108(4) 0.049(3) 0.052(3) 0.005(2) -0.001(3) -0.008(3) C7 0.053(3) 0.041(2) 0.049(2) -0.0038(18) 0.002(2) -0.0130(19) C8 0.048(2) 0.036(2) 0.057(2) -0.0071(19) 0.003(2) -0.0105(19) C9 0.064(3) 0.042(2) 0.053(2) -0.0001(19) 0.001(2) -0.012(2) C10 0.074(3) 0.060(3) 0.047(2) -0.012(2) -0.001(2) -0.014(2) C11 0.058(3) 0.045(2) 0.073(3) -0.017(2) 0.001(2) -0.012(2) C12 0.059(3) 0.041(2) 0.068(3) -0.006(2) -0.001(2) -0.007(2) C13 0.058(3) 0.050(3) 0.053(2) -0.008(2) -0.003(2) -0.010(2) _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 N1 1.652(3) . ? S1 S2 2.1013(16) . ? S2 C2 1.729(4) . ? S3 N4 1.656(3) . ? S3 C4 1.739(4) . ? N1 C1 1.306(5) . ? N2 C5 1.375(4) . ? N2 C1 1.395(4) . ? N2 C6 1.477(4) . ? N3 C5 1.325(4) . ? N3 C7 1.374(4) . ? N4 C7 1.299(4) . ? C1 C2 1.425(5) . ? C2 C3 1.364(5) . ? C3 C4 1.379(5) . ? C4 C5 1.431(5) . ? C7 C8 1.499(5) . ? C8 C9 1.386(5) . ? C8 C13 1.387(5) . ? C9 C10 1.381(5) . ? C10 C11 1.375(5) . ? C11 C12 1.372(5) . ? C12 C13 1.388(5) . ? 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 S1 S2 98.96(13) . . ? C2 S2 S1 91.37(14) . . ? N4 S3 C4 106.53(17) . . ? C1 N1 S1 113.2(3) . . ? C5 N2 C1 121.5(3) . . ? C5 N2 C6 120.4(3) . . ? C1 N2 C6 118.1(3) . . ? C5 N3 C7 120.9(3) . . ? C7 N4 S3 120.8(3) . . ? N1 C1 N2 118.0(3) . . ? N1 C1 C2 123.1(3) . . ? N2 C1 C2 118.9(4) . . ? C3 C2 C1 120.6(4) . . ? C3 C2 S2 126.0(3) . . ? C1 C2 S2 113.4(3) . . ? C2 C3 C4 119.6(4) . . ? C3 C4 C5 121.7(4) . . ? C3 C4 S3 121.4(3) . . ? C5 C4 S3 116.9(3) . . ? N3 C5 N2 116.5(3) . . ? N3 C5 C4 125.9(4) . . ? N2 C5 C4 117.7(3) . . ? N4 C7 N3 129.0(4) . . ? N4 C7 C8 116.0(4) . . ? N3 C7 C8 115.0(3) . . ? C9 C8 C13 119.7(4) . . ? C9 C8 C7 121.4(3) . . ? C13 C8 C7 118.9(4) . . ? C10 C9 C8 119.9(4) . . ? C11 C10 C9 120.8(4) . . ? C12 C11 C10 119.2(4) . . ? C11 C12 C13 121.1(4) . . ? C8 C13 C12 119.3(4) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.40 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.542 _refine_diff_density_min -0.382 _refine_diff_density_rms 0.084