# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1434 data_global # 1. SUBMISSION DETAILS _publ_contact_author #Name and address of author for correspondence ; Wally Cordes, Dept of Chem, Univ of Arkansas, Fayetteville, AR 72701 ; _publ_contact_author_phone 501-575-5270 _publ_contact_author_fax 501-575-4049 _publ_contact_author_email wcordes@comp.uark.edu _publ_requested_journal 'Chemical Communications' # 3. TITLE AND AUTHOR LIST _publ_section_title ; A bimodal dithiadiazolyl diradical: Crystal structure and magnetic properties of the 2,2'-dimethylbiphenylene bridged derivative ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Barclay, T.M.' ;Department of Chemistry and Biochemistry University of Arkansas Fayetteville, Arkansas 72701 USA ; 'Cordes, A.W.' ;Department of Chemistry and Biochemistry University of Arkansas Fayetteville, Arkansas 72701 USA ; 'George, N.A.' ;Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; 'Haddon, R.C.' ;Departments of Chemistry and Physics and Advanced Carbon Materials Center University of Kentucky Lexington, Kentucky 40506 USA ; 'Itkis, M.E.' ;Departments of Chemistry and Physics and Advanced Carbon Materials Center University of Kentucky Lexington, Kentucky 40506 USA ; 'Oakley, R.T.' ;Department of Chemistry University of Waterloo Waterloo, Ontario N2L 3G1 Canada ; # 4. TEXT _publ_section_experimental ; The CN2S2 rings were refined as rigid groups, with the origin at C fixed. Both were 50-50 disordered as was the C7 (C77) methyl group. Isotropic displacement parameters for N11, N22, etc. were kept equal to N1, N2 etc, respectively. ; # 5. CHEMICAL DATA _chemical_name_systematic ; 2,2'-dimethylbiphenylene-4,4'-bis(1,2,3,5-dithiadiazolyl) ; _chemical_formula_moiety 'S4 N4 C16 H12' _chemical_formula_weight 388.5 # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _cell_length_a 11.0371(11) _cell_length_b 8.489(2) _cell_length_c 18.854(2) _cell_angle_beta 103.299(9) _cell_volume 1719.1(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _exptl_crystal_colour black _exptl_crystal_density_diffrn 1.505 _exptl_crystal_F_000 805.96 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8212 _exptl_absorpt_correction_T_max 0.8855 # 7. EXPERIMENTAL DATA _diffrn_ambient_temperature 293 _diffrn_radiation_type 'Molybdenum K\a' _diffrn_measurement_device 'Nonius CAD-4 ' _diffrn_measurement_method 'Theta/2theta scan b/P/b ' _diffrn_reflns_number 3470 _diffrn_reflns_av_R_equivalents 0.031 _diffrn_reflns_theta_max 25.91 _reflns_number_total 3368 _reflns_number_observed 1375 _reflns_observed_criterion 'Inet 1.0\s(Inet)' _computing_structure_refinement 'NRCVAX' # 8. REFINEMENT DATA _refine_ls_weighting_scheme 1/(\s^2^(F)+0.0025F^2^) _refine_ls_number_reflns 1349 _refine_ls_number_parameters 202 _refine_ls_R_factor_obs 0.117 # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol C1 0.3978(12) 0.7557(18) 0.4013(7) 0.080(9) Uij ? . C C2 0.3410(14) 0.6528(16) 0.4394(6) 0.091(10) Uij ? . C C3 0.2482(13) 0.6974(19) 0.4713(6) 0.084(10) Uij ? . C C5 0.2065(14) 0.8500(18) 0.4632(7) 0.096(11) Uij ? . C C6 0.2612(13) 0.9512(15) 0.4224(7) 0.082(10) Uij ? . C C7 0.219(3) 1.091(4) 0.4133(17) 0.13(3) Uij ? . C C77 0.507(3) 0.711(4) 0.3756(18) 0.13(3) Uij ? . C C8 0.3585(11) 0.9089(18) 0.3923(5) 0.072(9) Uij ? . C C9 0.4117(11) 1.0292(16) 0.3504(6) 0.075(8) Uij ? . C C10 0.4892(16) 1.1432(21) 0.3891(7) 0.120(12) Uij ? . C C11 0.5389(13) 1.2611(20) 0.3542(7) 0.116(11) Uij ? . C C12 0.5147(10) 1.2631(14) 0.2793(6) 0.065(8) Uij ? . C C14 0.4404(10) 1.1510(14) 0.2416(5) 0.061(7) Uij ? . C C15 0.3902(9) 1.0297(14) 0.2753(5) 0.060(7) Uij ? . C C16 0.3063(15) 0.9127(19) 0.2318(6) 0.115(11) Uij ? . C H1 0.467 0.726 0.384 0.0919 Uiso ? . H H2 0.366 0.546 0.444 0.0959 Uiso ? . H H5 0.143 0.888 0.485 0.1125 Uiso ? . H H6 0.211 1.044 0.425 0.0915 Uiso ? . H H7a 0.196 1.120 0.360 0.1529 Uiso ? . H H7b 0.288 1.170 0.432 0.1529 Uiso ? . H H7c 0.150 1.117 0.435 0.1654 Uiso ? . H H77a 0.555 0.802 0.382 0.1129 Uiso ? . H H77b 0.474 0.697 0.324 0.1129 Uiso ? . H H77c 0.545 0.620 0.399 0.1129 Uiso ? . H H10 0.503 1.143 0.441 0.1290 Uiso ? . H H11 0.583 1.348 0.379 0.1230 Uiso ? . H H14 0.420 1.153 0.190 0.0734 Uiso ? . H H16a 0.352 0.839 0.210 0.1203 Uiso ? . H H16b 0.252 0.960 0.191 0.1203 Uiso ? . H H16c 0.260 0.856 0.260 0.1203 Uiso ? . H C4 0.18886 0.58775 0.51466 0.087(8) Uiso ? . C N1 0.1474(11) 0.6458(10) 0.5707(4) 0.084(7) Uiso ? . N N2 0.1804(11) 0.4344(3) 0.4977(6) 0.099(7) Uiso ? . N S1 0.0863(17) 0.5137(19) 0.6160(8) 0.100(9) Uij ? . S S2 0.1156(18) 0.3259(9) 0.5512(11) 0.119(10) Uij ? . S C44 0.18886 0.58775 0.51466 0.089(14) Uiso ? . C N11 0.1132(11) 0.6299(11) 0.5576(6) 0.088(11) Uiso ? . N N22 0.2226(12) 0.4377(4) 0.5088(6) 0.099(11) Uiso ? . N S11 0.0663(18) 0.4832(19) 0.6016(10) 0.145(14) Uij ? . S S22 0.1636(20) 0.3124(7) 0.5583(10) 0.126(12) Uij ? . S C13 0.56495 1.39029 0.24070 0.077(7) Uiso ? . C N3 0.5968(9) 1.3642(7) 0.1774(3) 0.051(4) Uiso ? . N N4 0.5761(8) 1.5325(3) 0.2722(3) 0.077(6) Uiso ? . N S3 0.6499(11) 1.5201(11) 0.1424(5) 0.114(8) Uij ? . S S4 0.6315(10) 1.6697(4) 0.2267(6) 0.105(7) Uij ? . S C133 0.56495 1.39029 0.24070 0.070(11) Uiso ? . C N33 0.5289(8) 1.3987(8) 0.16800(4) 0.049(14) Uiso ? . N N44 0.6441(7) 1.4947(7) 0.2796(3) 0.078(14) Uiso ? . N S33 0.5896(12) 1.5464(12) 0.1315(4) 0.114(9) Uij ? . S S44 0.6921(9) 1.6317(9) 0.2307(6) 0.132(9) Uij ? . S loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol C1 0.085(10) 0.090(10) 0.068(8) 0.009(8) 0.023(7) 0.017(8) C C2 0.129(12) 0.090(10) 0.048(7) -0.014(9) 0.010(8) 0.017(7) C C3 0.103(11) 0.110(12) 0.043(7) -0.023(9) 0.024(7) 0.012(7) C C5 0.143(13) 0.090(11) 0.071(9) -0.013(10) 0.055(9) 0.012(8) C C6 0.120(11) 0.051(9) 0.078(9) 0.010(8) 0.030(8) 0.017(7) C C7 0.20(3) 0.096(22) 0.15(3) -0.033(24) 0.15(3) -0.015(21) C C77 0.123(25) 0.12(3) 0.17(3) 0.068(21) 0.100(24) 0.062(22) C C8 0.070(9) 0.106(11) 0.045(6) -0.007(8) 0.027(6) -0.002(7) C C9 0.063(8) 0.115(10) 0.054(7) -0.002(8) 0.031(6) 0.002(8) C C10 0.157(14) 0.158(15) 0.040(7) -0.077(13) 0.011(8) 0.005(9) C C11 0.120(12) 0.165(15) 0.053(9) -0.077(11) 0.000(8) -0.003(9) C C12 0.048(7) 0.095(9) 0.058(7) -0.013(7) 0.022(6) 0.019(7) C C14 0.066(8) 0.083(8) 0.037(6) -0.011(7) 0.019(6) -0.006(6) C C15 0.050(7) 0.086(8) 0.041(6) 0.008(7) 0.003(5) 0.009(6) C C16 0.154(13) 0.140(12) 0.046(7) -0.052(12) 0.013(8) 0.002(8) C # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(19) ? ? ? C1 C77 1.45(3) ? ? ? C1 C8 1.369(22) ? ? ? C2 C3 1.356(21) ? ? ? C3 C5 1.372(23) ? ? ? C3 C4 1.486(12) ? ? ? C3 C44 1.486(12) ? ? ? C5 C6 1.382(18) ? ? ? C6 C7 1.27(4) ? ? ? C6 C8 1.372(18) ? ? ? C8 C9 1.493(17) ? ? ? C9 C10 1.383(21) ? ? ? C9 C15 1.380(15) ? ? ? C10 C11 1.378(20) ? ? ? C11 C12 1.377(17) ? ? ? C12 C14 1.348(18) ? ? ? C12 C13 1.479(10) ? ? ? C12 C133 1.479(10) ? ? ? C14 C15 1.391(16) ? ? ? C15 C16 1.472(19) ? ? ? C4 N1 1.338 ? ? ? C4 N2 1.338 ? ? ? N1 S1 1.645 ? ? ? N2 S2 1.645 ? ? ? S1 S2 2.080 ? ? ? N1 N11 0.423(15) ? ? ? N2 N22 0.465(17) ? ? ? S1 S11 0.402(22) ? ? ? S2 S22 0.53(3) ? ? ? N3 N33 0.786(12) ? ? ? N4 N44 0.799(11) ? ? ? S3 S33 0.687(17) ? ? ? S4 S44 0.731(14) ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C77 121.6(16) ? ? ? ? C2 C1 C8 120.0(12) ? ? ? ? C77 C1 C8 118.1(15) ? ? ? ? C1 C2 C3 122.5(13) ? ? ? ? C2 C3 C5 118.9(11) ? ? ? ? C2 C3 C4 122.9(13) ? ? ? ? C5 C3 C4 118.3(11) ? ? ? ? C3 C5 C6 118.1(12) ? ? ? ? C5 C6 C7 117.7(15) ? ? ? ? C5 C6 C8 123.4(13) ? ? ? ? C7 C6 C8 118.9(15) ? ? ? ? C1 C8 C6 117.0(11) ? ? ? ? C1 C8 C9 124.3(11) ? ? ? ? C6 C8 C9 118.7(13) ? ? ? ? C8 C9 C10 118.0(10) ? ? ? ? C8 C9 C15 123.4(12) ? ? ? ? C10 C9 C15 118.6(11) ? ? ? ? C9 C10 C11 121.5(11) ? ? ? ? C10 C11 C12 119.6(12) ? ? ? ? C11 C12 C14 118.9(10) ? ? ? ? C11 C12 C13 120.5(11) ? ? ? ? C11 C12 C133 120.5(11) ? ? ? ? C14 C12 C13 120.5(9) ? ? ? ? C14 C12 C133 120.5(9) ? ? ? ? C12 C14 C15 122.7(9) ? ? ? ? C9 C15 C14 118.6(11) ? ? ? ? C9 C15 C16 120.5(10) ? ? ? ? C14 C15 C16 120.7(9) ? ? ? ? C3 C4 N1 118.5(7) ? ? ? ? C3 C4 N2 119.6(8) ? ? ? ? C3 C4 N11 125.5(8) ? ? ? ? C3 C4 N22 112.6(9) ? ? ? ? N1 C4 N2 121.9 ? ? ? ? C4 N1 S1 114.5 ? ? ? ? C4 N2 S2 114.5 ? ? ? ? N1 S1 S2 94.5 ? ? ? ? N2 S2 S1 94.5 ? ? ? ?