Supplementary Material (ESI) for Journal of Materials Chemistry This journal is © The Royal Society of Chemistry 2002 data_global _journal_coden_Cambridge 1145 loop_ _publ_author_name 'Bell, N.A.' 'Crouch, D.J.' 'Simmonds, D.J.' 'Goeta, A.E.' 'Gelbrich, T.' 'Hursthouse, M.B.' _publ_contact_author_name 'Dr N Bell' _publ_contact_author_address ; Division of Chemistry School of Science Sheffield Hallam University Sheffield S1 1WB U.K. ; _publ_contact_author_phone '+44 191 3744702' _publ_contact_author_fax '+44 191 3844737' _publ_contact_author_email N.A.BELL@SHU.AC.UK _publ_requested_journal 'Journal of Materials Chemistry' _publ_section_title ; Structural and Solvatochromic Studies of a Series of Tricyanoquinodimethane Based Zwitterions ; _publ_section_references ; Beurskens, P.T., Beurskens, G., Bosman, W.P., de Gelder, R., Garcia-Granda, S., Gould, R.O., Israel, R. & Smits J.M.M. (1996), DIRDIF-96. Crystallography Laboratory, University of Nijmegen, The Netherlands. Blessing, R.H. SORTAV. Acta Cryst. A51 (1995) 33-37 & J. Appl. Cryst. 30 (1997) 421-426. Bruker (1998). SHELXTL-NT. Version 5.1. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Otwinowski, Z. & Minor W. (1997) DENZO. Methods in Enzymology, Vol. 276: Macromolecular Crystallography, part A, pp. 307-326; C. W. Carter, Jr. & R. M. Sweet, Eds., Academic Press. Sheldrick, G.M. (1990) Acta Cryst. A46, 467-473 Sheldrick, G.M. (1996). SADABS. Empirical Absorption Correction Program. University of Gottingen, Germany. Sheldrick, G.M. (1997) SHELXL-97. Program for the Refinement of Crystal Structures. University of Gottingen, Germany. Siemens (1996a). SMART V4.05/VMS. Data Collection Software. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Siemens (1996b). SAINT V4.05/VMS. Data Reduction Software. Bruker Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. ; #=================================================== data_98aeg002 _database_code_CSD 176117 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-\b-(N-propyl-2-benzothiazolium) -\a-cyano-4-(2,3,5,6-tetrafluoro)styryldicyanomethanide ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H12 F4 N4 S' _chemical_formula_weight 440.42 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' '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 monoclinic _symmetry_space_group_name_H-M 'P2(1)/c' 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 11.243(2) _cell_length_b 8.113(1) _cell_length_c 20.822(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.537(3) _cell_angle_gamma 90.00 _cell_volume 1860.8(6) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 512 _cell_measurement_theta_min 13.64 _cell_measurement_theta_max 22.95 _exptl_crystal_description 'irregular prism' _exptl_crystal_colour 'intense green' _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.572 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 896 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 0.977 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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-1K CCD Diffractometer' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 20416 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 28.28 _reflns_number_total 4609 _reflns_number_gt 3891 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART V4.05/VMS (Siemens, 1996a)' _computing_cell_refinement 'SMART V4.05/VMS (Siemens, 1996a)' _computing_data_reduction 'SAINT V4.05/VMS (Siemens, 1996b)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL-NT V5.1 (Bruker, 1998)' _computing_publication_material 'SHELXTL-NT V5.1 (Bruker, 1998)' _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^)+(0.0328P)^2^+0.9143P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4609 _refine_ls_number_parameters 328 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0330 _refine_ls_wR_factor_ref 0.0853 _refine_ls_wR_factor_gt 0.0788 _refine_ls_goodness_of_fit_ref 1.086 _refine_ls_restrained_S_all 1.086 _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 S1 S 0.96713(3) 0.41779(4) 0.119133(17) 0.02315(9) Uani 1 1 d . . . F1 F 1.29193(8) 0.69511(11) 0.33736(4) 0.02906(19) Uani 1 1 d . . . F2 F 1.38280(7) 0.68002(11) 0.46245(4) 0.02844(19) Uani 1 1 d . . . F3 F 1.06065(7) 0.32637(11) 0.49119(4) 0.02688(19) Uani 1 1 d . . . F4 F 0.97567(7) 0.33064(10) 0.36528(4) 0.02515(18) Uani 1 1 d . . . N1 N 0.79370(10) 0.57476(14) 0.15398(5) 0.0192(2) Uani 1 1 d . . . N2 N 1.23112(13) 0.5737(2) 0.19784(7) 0.0443(4) Uani 1 1 d . . . N3 N 1.48573(13) 0.6081(2) 0.60791(7) 0.0396(4) Uani 1 1 d . . . N4 N 1.17660(12) 0.35274(17) 0.63899(6) 0.0300(3) Uani 1 1 d . . . C1 C 0.54113(15) 0.6418(2) 0.25061(8) 0.0321(3) Uani 1 1 d . . . H11 H 0.4949(19) 0.721(3) 0.2215(10) 0.052(6) Uiso 1 1 d . . . H12 H 0.5889(18) 0.699(3) 0.2870(10) 0.044(5) Uiso 1 1 d . . . H13 H 0.4879(19) 0.570(3) 0.2677(10) 0.043(5) Uiso 1 1 d . . . C2 C 0.62402(13) 0.54429(19) 0.21473(7) 0.0259(3) Uani 1 1 d . . . H21 H 0.5772(16) 0.494(2) 0.1761(9) 0.030(4) Uiso 1 1 d . . . H22 H 0.6679(17) 0.454(2) 0.2432(9) 0.035(5) Uiso 1 1 d . . . C3 C 0.71677(12) 0.65931(17) 0.19428(7) 0.0206(3) Uani 1 1 d . . . H31 H 0.6765(15) 0.750(2) 0.1682(8) 0.023(4) Uiso 1 1 d . . . H32 H 0.7707(15) 0.701(2) 0.2330(8) 0.023(4) Uiso 1 1 d . . . C4 C 0.75682(12) 0.55643(16) 0.08610(6) 0.0198(3) Uani 1 1 d . . . C5 C 0.65062(13) 0.61675(18) 0.04665(7) 0.0235(3) Uani 1 1 d . . . H51 H 0.5941(15) 0.676(2) 0.0641(8) 0.027(4) Uiso 1 1 d . . . C6 C 0.63403(13) 0.58778(19) -0.01989(7) 0.0264(3) Uani 1 1 d . . . H61 H 0.5632(16) 0.626(2) -0.0484(9) 0.031(4) Uiso 1 1 d . . . C7 C 0.71913(14) 0.49850(19) -0.04717(7) 0.0278(3) Uani 1 1 d . . . H71 H 0.7067(16) 0.481(2) -0.0935(9) 0.031(4) Uiso 1 1 d . . . C8 C 0.82424(14) 0.43919(18) -0.00834(7) 0.0258(3) Uani 1 1 d . . . H81 H 0.8825(15) 0.380(2) -0.0254(8) 0.027(4) Uiso 1 1 d . . . C9 C 0.84303(12) 0.47065(17) 0.05901(7) 0.0216(3) Uani 1 1 d . . . C10 C 0.90319(12) 0.51031(17) 0.17824(7) 0.0204(3) Uani 1 1 d . . . C11 C 0.95709(12) 0.51284(18) 0.24742(7) 0.0228(3) Uani 1 1 d . . . H111 H 0.9042(17) 0.513(2) 0.2766(9) 0.032(5) Uiso 1 1 d . . . C12 C 1.07804(12) 0.52431(17) 0.27374(7) 0.0211(3) Uani 1 1 d . . . C13 C 1.16366(13) 0.55174(19) 0.23119(7) 0.0265(3) Uani 1 1 d . . . C14 C 1.12825(12) 0.51468(17) 0.34378(6) 0.0202(3) Uani 1 1 d . . . C15 C 1.23536(12) 0.59695(17) 0.37381(7) 0.0214(3) Uani 1 1 d . . . C16 C 1.28205(12) 0.59076(17) 0.43953(7) 0.0212(3) Uani 1 1 d . . . C17 C 1.22797(12) 0.50139(16) 0.48455(6) 0.0199(3) Uani 1 1 d . . . C18 C 1.12025(12) 0.41959(16) 0.45401(7) 0.0206(3) Uani 1 1 d . . . C19 C 1.07414(12) 0.42481(16) 0.38815(7) 0.0202(3) Uani 1 1 d . . . C20 C 1.27704(12) 0.49409(17) 0.55288(7) 0.0223(3) Uani 1 1 d . . . C21 C 1.39249(13) 0.56006(19) 0.58159(7) 0.0269(3) Uani 1 1 d . . . C22 C 1.21837(12) 0.41411(18) 0.59880(7) 0.0232(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 0.01771(16) 0.02479(17) 0.02786(17) 0.00056(13) 0.00672(12) 0.00371(13) F1 0.0272(4) 0.0323(5) 0.0286(4) 0.0038(4) 0.0077(3) -0.0096(4) F2 0.0230(4) 0.0323(5) 0.0296(4) -0.0024(4) 0.0042(3) -0.0128(4) F3 0.0237(4) 0.0298(5) 0.0268(4) 0.0042(3) 0.0044(3) -0.0100(3) F4 0.0194(4) 0.0254(4) 0.0286(4) 0.0010(3) -0.0003(3) -0.0072(3) N1 0.0157(5) 0.0198(5) 0.0224(5) 0.0014(4) 0.0048(4) 0.0000(4) N2 0.0268(7) 0.0772(12) 0.0298(7) -0.0041(7) 0.0080(6) -0.0124(7) N3 0.0332(7) 0.0539(9) 0.0296(7) 0.0015(6) 0.0013(6) -0.0208(7) N4 0.0264(6) 0.0375(7) 0.0257(6) -0.0007(5) 0.0044(5) -0.0071(6) C1 0.0235(7) 0.0428(9) 0.0328(8) 0.0035(7) 0.0122(6) 0.0067(7) C2 0.0209(7) 0.0293(8) 0.0292(7) -0.0010(6) 0.0090(5) -0.0017(6) C3 0.0167(6) 0.0226(7) 0.0230(6) -0.0011(5) 0.0053(5) 0.0020(5) C4 0.0187(6) 0.0191(6) 0.0222(6) 0.0012(5) 0.0059(5) -0.0023(5) C5 0.0198(6) 0.0244(7) 0.0264(7) 0.0005(5) 0.0053(5) 0.0007(5) C6 0.0235(7) 0.0288(7) 0.0257(7) 0.0021(6) 0.0023(5) -0.0004(6) C7 0.0295(8) 0.0319(8) 0.0229(7) -0.0013(6) 0.0077(6) -0.0038(6) C8 0.0264(7) 0.0259(7) 0.0277(7) -0.0020(6) 0.0119(6) -0.0012(6) C9 0.0184(6) 0.0197(6) 0.0278(7) 0.0018(5) 0.0071(5) -0.0005(5) C10 0.0159(6) 0.0203(6) 0.0260(6) 0.0022(5) 0.0062(5) -0.0005(5) C11 0.0184(6) 0.0254(7) 0.0251(7) 0.0021(5) 0.0056(5) 0.0024(5) C12 0.0187(6) 0.0195(6) 0.0252(6) 0.0004(5) 0.0050(5) 0.0019(5) C13 0.0176(6) 0.0351(8) 0.0254(7) 0.0005(6) 0.0015(5) -0.0007(6) C14 0.0165(6) 0.0198(6) 0.0243(6) 0.0007(5) 0.0042(5) 0.0018(5) C15 0.0179(6) 0.0199(6) 0.0278(7) 0.0015(5) 0.0081(5) -0.0010(5) C16 0.0158(6) 0.0201(6) 0.0279(7) -0.0034(5) 0.0049(5) -0.0036(5) C17 0.0165(6) 0.0179(6) 0.0256(6) -0.0022(5) 0.0051(5) 0.0003(5) C18 0.0187(6) 0.0175(6) 0.0264(6) 0.0008(5) 0.0067(5) -0.0018(5) C19 0.0148(6) 0.0166(6) 0.0286(7) -0.0017(5) 0.0030(5) -0.0009(5) C20 0.0189(6) 0.0225(7) 0.0251(7) -0.0017(5) 0.0033(5) -0.0031(5) C21 0.0272(7) 0.0298(8) 0.0236(6) -0.0009(6) 0.0051(5) -0.0064(6) C22 0.0191(6) 0.0246(7) 0.0250(6) -0.0032(5) 0.0018(5) -0.0013(5) _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 C10 1.7173(14) . ? S1 C9 1.7318(14) . ? F1 C15 1.3445(15) . ? F2 C16 1.3487(15) . ? F3 C18 1.3519(15) . ? F4 C19 1.3510(15) . ? N1 C10 1.3398(17) . ? N1 C4 1.3992(17) . ? N1 C3 1.4876(17) . ? N2 C13 1.140(2) . ? N3 C21 1.1494(19) . ? N4 C22 1.1516(19) . ? C1 C2 1.527(2) . ? C1 H11 0.96(2) . ? C1 H12 0.96(2) . ? C1 H13 0.95(2) . ? C2 C3 1.522(2) . ? C2 H21 0.960(18) . ? C2 H22 1.007(19) . ? C3 H31 0.971(17) . ? C3 H32 0.968(17) . ? C4 C5 1.3955(19) . ? C4 C9 1.4002(19) . ? C5 C6 1.381(2) . ? C5 H51 0.927(17) . ? C6 C7 1.407(2) . ? C6 H61 0.945(18) . ? C7 C8 1.378(2) . ? C7 H71 0.958(18) . ? C8 C9 1.399(2) . ? C8 H81 0.939(17) . ? C10 C11 1.4468(19) . ? C11 C12 1.3638(19) . ? C11 H111 0.932(18) . ? C12 C13 1.4499(19) . ? C12 C14 1.4569(19) . ? C14 C19 1.4071(18) . ? C14 C15 1.4091(19) . ? C15 C16 1.3651(19) . ? C16 C17 1.4150(18) . ? C17 C18 1.4155(18) . ? C17 C20 1.4206(19) . ? C18 C19 1.3663(19) . ? C20 C21 1.4207(19) . ? C20 C22 1.4222(19) . ? 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 C10 S1 C9 91.01(7) . . ? C10 N1 C4 113.81(11) . . ? C10 N1 C3 124.15(11) . . ? C4 N1 C3 122.04(11) . . ? C2 C1 H11 110.1(13) . . ? C2 C1 H12 109.8(12) . . ? H11 C1 H12 108.5(18) . . ? C2 C1 H13 110.8(12) . . ? H11 C1 H13 110.2(17) . . ? H12 C1 H13 107.3(17) . . ? C3 C2 C1 109.80(13) . . ? C3 C2 H21 108.6(11) . . ? C1 C2 H21 110.2(11) . . ? C3 C2 H22 109.1(11) . . ? C1 C2 H22 111.4(10) . . ? H21 C2 H22 107.7(15) . . ? N1 C3 C2 112.53(11) . . ? N1 C3 H31 107.0(9) . . ? C2 C3 H31 110.6(10) . . ? N1 C3 H32 107.0(10) . . ? C2 C3 H32 109.5(10) . . ? H31 C3 H32 110.0(14) . . ? C5 C4 N1 127.10(12) . . ? C5 C4 C9 121.12(12) . . ? N1 C4 C9 111.75(12) . . ? C6 C5 C4 117.32(13) . . ? C6 C5 H51 121.0(10) . . ? C4 C5 H51 121.6(10) . . ? C5 C6 C7 121.76(14) . . ? C5 C6 H61 120.2(11) . . ? C7 C6 H61 118.0(11) . . ? C8 C7 C6 121.02(13) . . ? C8 C7 H71 118.3(11) . . ? C6 C7 H71 120.7(11) . . ? C7 C8 C9 117.66(13) . . ? C7 C8 H81 122.6(10) . . ? C9 C8 H81 119.8(10) . . ? C8 C9 C4 121.09(13) . . ? C8 C9 S1 128.14(11) . . ? C4 C9 S1 110.76(10) . . ? N1 C10 C11 122.69(12) . . ? N1 C10 S1 112.65(10) . . ? C11 C10 S1 124.59(10) . . ? C12 C11 C10 125.90(13) . . ? C12 C11 H111 116.9(11) . . ? C10 C11 H111 117.1(11) . . ? C11 C12 C13 119.70(12) . . ? C11 C12 C14 123.65(12) . . ? C13 C12 C14 116.63(12) . . ? N2 C13 C12 179.80(19) . . ? C19 C14 C15 113.42(12) . . ? C19 C14 C12 123.59(12) . . ? C15 C14 C12 122.99(12) . . ? F1 C15 C16 117.21(12) . . ? F1 C15 C14 119.26(12) . . ? C16 C15 C14 123.41(12) . . ? F2 C16 C15 117.53(12) . . ? F2 C16 C17 118.85(12) . . ? C15 C16 C17 123.58(12) . . ? C16 C17 C18 112.64(12) . . ? C16 C17 C20 123.55(12) . . ? C18 C17 C20 123.81(12) . . ? F3 C18 C19 117.39(12) . . ? F3 C18 C17 118.84(12) . . ? C19 C18 C17 123.73(12) . . ? F4 C19 C18 117.13(12) . . ? F4 C19 C14 119.54(12) . . ? C18 C19 C14 123.23(12) . . ? C17 C20 C21 123.02(12) . . ? C17 C20 C22 123.57(12) . . ? C21 C20 C22 113.36(12) . . ? N3 C21 C20 176.13(16) . . ? N4 C22 C20 175.77(15) . . ? 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 C10 N1 C3 C2 -95.21(15) . . . . ? C4 N1 C3 C2 85.08(15) . . . . ? C1 C2 C3 N1 -175.04(12) . . . . ? C10 N1 C4 C5 -176.90(13) . . . . ? C3 N1 C4 C5 2.8(2) . . . . ? C10 N1 C4 C9 1.27(16) . . . . ? C3 N1 C4 C9 -178.99(11) . . . . ? N1 C4 C5 C6 178.27(13) . . . . ? C9 C4 C5 C6 0.3(2) . . . . ? C4 C5 C6 C7 1.2(2) . . . . ? C5 C6 C7 C8 -1.4(2) . . . . ? C6 C7 C8 C9 0.1(2) . . . . ? C7 C8 C9 C4 1.3(2) . . . . ? C7 C8 C9 S1 -177.90(11) . . . . ? C5 C4 C9 C8 -1.5(2) . . . . ? N1 C4 C9 C8 -179.81(12) . . . . ? C5 C4 C9 S1 177.80(11) . . . . ? N1 C4 C9 S1 -0.49(14) . . . . ? C10 S1 C9 C8 179.00(14) . . . . ? C10 S1 C9 C4 -0.26(11) . . . . ? C4 N1 C10 C11 -178.62(12) . . . . ? C3 N1 C10 C11 1.6(2) . . . . ? C4 N1 C10 S1 -1.47(14) . . . . ? C3 N1 C10 S1 178.79(10) . . . . ? C9 S1 C10 N1 0.99(11) . . . . ? C9 S1 C10 C11 178.07(12) . . . . ? N1 C10 C11 C12 -147.54(14) . . . . ? S1 C10 C11 C12 35.7(2) . . . . ? C10 C11 C12 C13 6.1(2) . . . . ? C10 C11 C12 C14 -175.51(13) . . . . ? C11 C12 C13 N2 128(100) . . . . ? C14 C12 C13 N2 -51(75) . . . . ? C11 C12 C14 C19 29.2(2) . . . . ? C13 C12 C14 C19 -152.38(13) . . . . ? C11 C12 C14 C15 -149.87(14) . . . . ? C13 C12 C14 C15 28.6(2) . . . . ? C19 C14 C15 F1 -176.09(12) . . . . ? C12 C14 C15 F1 3.1(2) . . . . ? C19 C14 C15 C16 -0.2(2) . . . . ? C12 C14 C15 C16 178.94(13) . . . . ? F1 C15 C16 F2 -1.66(19) . . . . ? C14 C15 C16 F2 -177.61(12) . . . . ? F1 C15 C16 C17 175.87(12) . . . . ? C14 C15 C16 C17 -0.1(2) . . . . ? F2 C16 C17 C18 177.39(11) . . . . ? C15 C16 C17 C18 -0.11(19) . . . . ? F2 C16 C17 C20 -2.9(2) . . . . ? C15 C16 C17 C20 179.56(13) . . . . ? C16 C17 C18 F3 178.52(11) . . . . ? C20 C17 C18 F3 -1.2(2) . . . . ? C16 C17 C18 C19 0.66(19) . . . . ? C20 C17 C18 C19 -179.01(13) . . . . ? F3 C18 C19 F4 -2.76(18) . . . . ? C17 C18 C19 F4 175.12(12) . . . . ? F3 C18 C19 C14 -178.93(12) . . . . ? C17 C18 C19 C14 -1.0(2) . . . . ? C15 C14 C19 F4 -175.32(11) . . . . ? C12 C14 C19 F4 5.5(2) . . . . ? C15 C14 C19 C18 0.76(19) . . . . ? C12 C14 C19 C18 -178.39(13) . . . . ? C16 C17 C20 C21 -7.5(2) . . . . ? C18 C17 C20 C21 172.12(13) . . . . ? C16 C17 C20 C22 175.36(13) . . . . ? C18 C17 C20 C22 -5.0(2) . . . . ? C17 C20 C21 N3 -163(3) . . . . ? C22 C20 C21 N3 15(3) . . . . ? C17 C20 C22 N4 -176(2) . . . . ? C21 C20 C22 N4 6(2) . . . . ? 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 C7 H71 N2 0.958(18) 2.452(18) 3.347(2) 155.5(14) 3_765 C3 H31 N3 0.971(17) 2.535(17) 3.4167(19) 151.0(13) 4_475 C5 H51 N3 0.927(17) 2.414(18) 3.316(2) 164.1(14) 4_475 C3 H32 N4 0.968(17) 2.650(16) 3.440(2) 139.0(13) 3_766 C11 H111 N4 0.932(18) 2.394(18) 3.235(2) 150.0(15) 3_766 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.318 _refine_diff_density_min -0.300 _refine_diff_density_rms 0.046 #==END data_s92 _database_code_CSD 176118 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (Z)-\b-(N-butyl-2-benzoselenozolium) -\a-cyano-4-styryldicyanomethanide ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H18 N4 Se' _chemical_formula_weight 429.37 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' 'Se' 'Se' -0.0929 2.2259 '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 8.0663(3) _cell_length_b 9.4561(2) _cell_length_c 12.8115(5) _cell_angle_alpha 83.317(2) _cell_angle_beta 81.4890(10) _cell_angle_gamma 89.601(2) _cell_volume 959.83(6) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 12468 _cell_measurement_theta_min 2.2 _cell_measurement_theta_max 26.0 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 1.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.756 _exptl_absorpt_correction_T_max 0.827 _exptl_absorpt_process_details 'SORTAV (Blessing, 1995 & 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 'Enraf Nonius KappaCCD Diffractometer' _diffrn_measurement_method '\w and \p scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12251 _diffrn_reflns_av_R_equivalents 0.0662 _diffrn_reflns_av_sigmaI/netI 0.0793 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.00 _reflns_number_total 3746 _reflns_number_gt 2937 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DENZO (Otwinowski & Minor, 1997)' _computing_cell_refinement 'DENZO (Otwinowski, 1997)' _computing_data_reduction 'DENZO (Otwinowski, 1997)' _computing_structure_solution 'DIRDIF-96 (Beurskens et al., 1996)' _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^)+(0.0278P)^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 SHELXL _refine_ls_extinction_coef 0.0038(17) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3746 _refine_ls_number_parameters 323 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.0784 _refine_ls_wR_factor_gt 0.0732 _refine_ls_goodness_of_fit_ref 0.996 _refine_ls_restrained_S_all 0.996 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Se1 Se 0.14486(4) 0.18128(3) 0.03079(2) 0.02473(13) Uani 1 d . . . N1 N 0.2602(3) 0.2933(2) 0.18882(16) 0.0198(5) Uani 1 d . . . N2 N 0.0833(3) 0.3742(2) -0.17871(19) 0.0322(6) Uani 1 d . . . N3 N 0.5094(3) 1.2810(2) -0.16521(18) 0.0308(6) Uani 1 d . . . N4 N 0.3054(5) 1.1879(3) -0.4444(2) 0.0700(12) Uani 1 d . . . C1 C 0.1532(4) 0.0732(3) 0.1611(2) 0.0230(7) Uani 1 d . . . C2 C 0.2170(3) 0.1520(3) 0.2314(2) 0.0203(6) Uani 1 d . . . C3 C 0.2316(4) 0.0914(3) 0.3339(2) 0.0271(7) Uani 1 d . . . H3 H 0.278(3) 0.143(3) 0.3844(19) 0.019(7) Uiso 1 d . . . C4 C 0.1794(4) -0.0473(3) 0.3636(2) 0.0341(8) Uani 1 d . . . H4 H 0.185(4) -0.094(3) 0.432(2) 0.040(9) Uiso 1 d . . . C5 C 0.1158(4) -0.1268(3) 0.2931(2) 0.0324(8) Uani 1 d . . . H5 H 0.073(4) -0.222(3) 0.314(2) 0.040(9) Uiso 1 d . . . C6 C 0.1034(4) -0.0688(3) 0.1918(2) 0.0278(7) Uani 1 d . . . H6 H 0.064(4) -0.121(3) 0.141(2) 0.028(8) Uiso 1 d . . . C7 C 0.3437(4) 0.3838(3) 0.2541(2) 0.0217(6) Uani 1 d . . . H7A H 0.412(3) 0.457(2) 0.2057(18) 0.007(6) Uiso 1 d . . . H7B H 0.412(4) 0.321(3) 0.287(2) 0.022(8) Uiso 1 d . . . C8 C 0.2246(4) 0.4467(3) 0.3393(2) 0.0242(7) Uani 1 d . . . H8A H 0.156(3) 0.371(3) 0.3851(19) 0.020(7) Uiso 1 d . . . H8B H 0.155(4) 0.514(3) 0.305(2) 0.021(7) Uiso 1 d . . . C9 C 0.3239(4) 0.5200(3) 0.4110(2) 0.0295(7) Uani 1 d . . . H9A H 0.386(3) 0.594(3) 0.369(2) 0.025(7) Uiso 1 d . . . H9B H 0.408(4) 0.448(3) 0.436(2) 0.030(8) Uiso 1 d . . . C10 C 0.2160(5) 0.5706(4) 0.5064(3) 0.0351(8) Uani 1 d . . . H10A H 0.287(4) 0.626(3) 0.545(2) 0.041(9) Uiso 1 d . . . H10B H 0.162(4) 0.483(4) 0.556(3) 0.058(10) Uiso 1 d . . . H10C H 0.128(4) 0.628(3) 0.487(2) 0.042(10) Uiso 1 d . . . C11 C 0.2300(3) 0.3345(3) 0.0890(2) 0.0192(6) Uani 1 d . . . C12 C 0.2622(4) 0.4736(3) 0.0366(2) 0.0218(6) Uani 1 d . . . H12 H 0.306(3) 0.536(3) 0.079(2) 0.021(7) Uiso 1 d . . . C13 C 0.2296(3) 0.5277(3) -0.0634(2) 0.0192(6) Uani 1 d . . . C14 C 0.1506(4) 0.4395(3) -0.1269(2) 0.0218(6) Uani 1 d . . . C15 C 0.2648(3) 0.6716(3) -0.1129(2) 0.0209(6) Uani 1 d . . . C16 C 0.2231(4) 0.7191(3) -0.2141(2) 0.0255(7) Uani 1 d . . . H16 H 0.1705 0.6543 -0.2506 0.021(7) Uiso 1 calc R . . C17 C 0.2555(4) 0.8546(3) -0.2615(2) 0.0262(7) Uani 1 d . . . H17 H 0.221(4) 0.887(3) -0.330(2) 0.035(8) Uiso 1 d . . . C18 C 0.3340(4) 0.9559(3) -0.2105(2) 0.0220(6) Uani 1 d . . . C19 C 0.3770(4) 0.9072(3) -0.1096(2) 0.0225(7) Uani 1 d . . . H19 H 0.427(4) 0.971(3) -0.073(2) 0.028(8) Uiso 1 d . . . C20 C 0.3438(4) 0.7720(3) -0.0618(2) 0.0234(7) Uani 1 d . . . H20 H 0.372(4) 0.742(3) 0.006(2) 0.029(8) Uiso 1 d . . . C21 C 0.3702(4) 1.0974(3) -0.2581(2) 0.0267(7) Uani 1 d . . . C22 C 0.4485(4) 1.1975(3) -0.2066(2) 0.0251(7) Uani 1 d . . . C23 C 0.3333(5) 1.1475(3) -0.3609(3) 0.0395(9) Uani 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 0.0336(2) 0.01966(18) 0.02269(19) -0.00258(11) -0.00965(13) -0.00292(12) N1 0.0214(14) 0.0194(11) 0.0199(12) -0.0037(9) -0.0066(10) 0.0001(10) N2 0.0426(18) 0.0238(13) 0.0333(15) -0.0001(11) -0.0181(13) -0.0018(12) N3 0.0439(18) 0.0237(13) 0.0245(13) 0.0035(10) -0.0089(12) -0.0071(12) N4 0.146(4) 0.0352(17) 0.0363(18) 0.0087(14) -0.047(2) -0.0225(19) C1 0.0265(18) 0.0213(14) 0.0218(15) -0.0026(11) -0.0057(13) 0.0026(12) C2 0.0186(16) 0.0188(14) 0.0237(15) -0.0013(11) -0.0052(12) 0.0001(11) C3 0.037(2) 0.0239(16) 0.0226(16) -0.0037(12) -0.0124(14) -0.0008(13) C4 0.054(2) 0.0266(17) 0.0226(17) 0.0035(13) -0.0136(16) -0.0034(15) C5 0.045(2) 0.0206(16) 0.0321(18) 0.0028(13) -0.0110(15) -0.0064(14) C6 0.036(2) 0.0203(15) 0.0286(17) -0.0034(13) -0.0103(14) -0.0015(13) C7 0.0265(18) 0.0188(15) 0.0222(16) -0.0027(12) -0.0111(14) -0.0017(13) C8 0.0304(19) 0.0231(16) 0.0209(16) -0.0042(12) -0.0086(14) -0.0001(14) C9 0.038(2) 0.0316(17) 0.0204(16) -0.0038(13) -0.0082(15) -0.0092(16) C10 0.046(2) 0.0353(19) 0.0262(18) -0.0099(15) -0.0070(17) -0.0014(18) C11 0.0176(16) 0.0213(14) 0.0191(15) -0.0043(11) -0.0028(12) 0.0016(11) C12 0.0242(17) 0.0197(14) 0.0226(16) -0.0042(12) -0.0054(13) 0.0015(12) C13 0.0183(16) 0.0203(14) 0.0196(15) -0.0035(11) -0.0042(12) 0.0004(11) C14 0.0262(17) 0.0181(14) 0.0204(15) 0.0023(11) -0.0047(13) 0.0022(12) C15 0.0212(17) 0.0220(14) 0.0198(15) -0.0033(11) -0.0039(12) 0.0039(12) C16 0.0314(19) 0.0235(15) 0.0246(16) -0.0089(12) -0.0091(13) -0.0009(13) C17 0.034(2) 0.0257(15) 0.0203(16) -0.0007(12) -0.0106(14) -0.0004(13) C18 0.0266(18) 0.0212(14) 0.0190(15) -0.0020(11) -0.0063(13) 0.0017(12) C19 0.0247(18) 0.0213(15) 0.0242(16) -0.0067(12) -0.0094(13) 0.0009(12) C20 0.0273(18) 0.0254(15) 0.0186(16) -0.0023(12) -0.0071(13) 0.0018(12) C21 0.037(2) 0.0226(15) 0.0225(16) -0.0015(12) -0.0107(14) -0.0026(13) C22 0.0325(19) 0.0207(15) 0.0207(15) 0.0045(12) -0.0050(13) 0.0013(13) C23 0.067(3) 0.0223(16) 0.0320(19) -0.0014(13) -0.0186(17) -0.0102(16) _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 C1 1.863(3) . ? Se1 C11 1.883(2) . ? N1 C11 1.349(3) . ? N1 C2 1.409(3) . ? N1 C7 1.492(3) . ? N2 C14 1.150(3) . ? N3 C22 1.151(3) . ? N4 C23 1.147(4) . ? C1 C2 1.389(4) . ? C1 C6 1.399(4) . ? C2 C3 1.393(4) . ? C3 C4 1.374(4) . ? C3 H3 0.97(2) . ? C4 C5 1.395(4) . ? C4 H4 0.94(3) . ? C5 C6 1.366(4) . ? C5 H5 0.96(3) . ? C6 H6 0.95(3) . ? C7 C8 1.518(4) . ? C7 H7A 0.99(2) . ? C7 H7B 0.91(3) . ? C8 C9 1.529(4) . ? C8 H8A 0.99(2) . ? C8 H8B 0.95(3) . ? C9 C10 1.514(4) . ? C9 H9A 0.93(3) . ? C9 H9B 1.02(3) . ? C10 H10A 1.00(3) . ? C10 H10B 1.04(3) . ? C10 H10C 0.94(4) . ? C11 C12 1.412(4) . ? C12 C13 1.385(4) . ? C12 H12 0.95(3) . ? C13 C14 1.443(4) . ? C13 C15 1.444(3) . ? C15 C16 1.410(4) . ? C15 C20 1.419(4) . ? C16 C17 1.363(4) . ? C16 H16 0.9500 . ? C17 C18 1.422(4) . ? C17 H17 0.97(3) . ? C18 C19 1.413(4) . ? C18 C21 1.417(4) . ? C19 C20 1.362(4) . ? C19 H19 0.93(3) . ? C20 H20 0.95(3) . ? C21 C22 1.416(4) . ? C21 C23 1.421(4) . ? 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 C1 Se1 C11 87.10(11) . . ? C11 N1 C2 116.9(2) . . ? C11 N1 C7 124.7(2) . . ? C2 N1 C7 118.3(2) . . ? C2 C1 C6 120.7(3) . . ? C2 C1 Se1 111.44(18) . . ? C6 C1 Se1 127.9(2) . . ? C1 C2 C3 120.6(2) . . ? C1 C2 N1 113.8(2) . . ? C3 C2 N1 125.6(2) . . ? C4 C3 C2 118.1(3) . . ? C4 C3 H3 119.2(15) . . ? C2 C3 H3 122.7(15) . . ? C3 C4 C5 121.4(3) . . ? C3 C4 H4 122.2(18) . . ? C5 C4 H4 116.4(18) . . ? C6 C5 C4 120.8(3) . . ? C6 C5 H5 117.2(18) . . ? C4 C5 H5 121.9(18) . . ? C5 C6 C1 118.4(3) . . ? C5 C6 H6 123.3(17) . . ? C1 C6 H6 118.3(17) . . ? N1 C7 C8 114.2(2) . . ? N1 C7 H7A 108.4(13) . . ? C8 C7 H7A 112.6(13) . . ? N1 C7 H7B 103.0(16) . . ? C8 C7 H7B 108.3(16) . . ? H7A C7 H7B 110(2) . . ? C7 C8 C9 110.0(3) . . ? C7 C8 H8A 110.3(14) . . ? C9 C8 H8A 107.2(15) . . ? C7 C8 H8B 108.4(15) . . ? C9 C8 H8B 110.3(15) . . ? H8A C8 H8B 111(2) . . ? C10 C9 C8 113.7(3) . . ? C10 C9 H9A 111.8(15) . . ? C8 C9 H9A 107.9(16) . . ? C10 C9 H9B 109.7(15) . . ? C8 C9 H9B 106.5(15) . . ? H9A C9 H9B 107(2) . . ? C9 C10 H10A 109.4(17) . . ? C9 C10 H10B 109.4(17) . . ? H10A C10 H10B 110(3) . . ? C9 C10 H10C 112.4(19) . . ? H10A C10 H10C 109(3) . . ? H10B C10 H10C 106(3) . . ? N1 C11 C12 123.7(2) . . ? N1 C11 Se1 110.64(17) . . ? C12 C11 Se1 125.7(2) . . ? C13 C12 C11 128.0(2) . . ? C13 C12 H12 118.3(16) . . ? C11 C12 H12 113.6(16) . . ? C12 C13 C14 120.4(2) . . ? C12 C13 C15 125.5(2) . . ? C14 C13 C15 114.1(2) . . ? N2 C14 C13 177.0(3) . . ? C16 C15 C20 116.8(2) . . ? C16 C15 C13 121.8(2) . . ? C20 C15 C13 121.4(3) . . ? C17 C16 C15 122.4(2) . . ? C17 C16 H16 118.8 . . ? C15 C16 H16 118.8 . . ? C16 C17 C18 121.1(3) . . ? C16 C17 H17 121.3(16) . . ? C18 C17 H17 117.5(16) . . ? C19 C18 C21 121.3(2) . . ? C19 C18 C17 116.2(2) . . ? C21 C18 C17 122.4(3) . . ? C20 C19 C18 122.8(2) . . ? C20 C19 H19 118.4(17) . . ? C18 C19 H19 118.8(17) . . ? C19 C20 C15 120.8(3) . . ? C19 C20 H20 121.3(16) . . ? C15 C20 H20 117.9(16) . . ? C22 C21 C18 122.0(3) . . ? C22 C21 C23 115.6(2) . . ? C18 C21 C23 122.4(2) . . ? N3 C22 C21 178.5(3) . . ? N4 C23 C21 179.2(4) . . ? 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 C11 Se1 C1 C2 -1.3(2) . . . . ? C11 Se1 C1 C6 178.3(3) . . . . ? C6 C1 C2 C3 -0.4(4) . . . . ? Se1 C1 C2 C3 179.2(2) . . . . ? C6 C1 C2 N1 -179.6(3) . . . . ? Se1 C1 C2 N1 0.0(3) . . . . ? C11 N1 C2 C1 2.0(4) . . . . ? C7 N1 C2 C1 -174.8(2) . . . . ? C11 N1 C2 C3 -177.1(3) . . . . ? C7 N1 C2 C3 6.1(4) . . . . ? C1 C2 C3 C4 -0.8(5) . . . . ? N1 C2 C3 C4 178.3(3) . . . . ? C2 C3 C4 C5 1.0(5) . . . . ? C3 C4 C5 C6 0.0(5) . . . . ? C4 C5 C6 C1 -1.1(5) . . . . ? C2 C1 C6 C5 1.3(5) . . . . ? Se1 C1 C6 C5 -178.1(2) . . . . ? C11 N1 C7 C8 103.3(3) . . . . ? C2 N1 C7 C8 -80.2(3) . . . . ? N1 C7 C8 C9 172.2(2) . . . . ? C7 C8 C9 C10 -173.1(3) . . . . ? C2 N1 C11 C12 178.2(2) . . . . ? C7 N1 C11 C12 -5.2(4) . . . . ? C2 N1 C11 Se1 -2.9(3) . . . . ? C7 N1 C11 Se1 173.6(2) . . . . ? C1 Se1 C11 N1 2.3(2) . . . . ? C1 Se1 C11 C12 -178.9(3) . . . . ? N1 C11 C12 C13 -177.2(3) . . . . ? Se1 C11 C12 C13 4.2(4) . . . . ? C11 C12 C13 C14 1.2(5) . . . . ? C11 C12 C13 C15 179.7(3) . . . . ? C12 C13 C14 N2 137(5) . . . . ? C15 C13 C14 N2 -41(5) . . . . ? C12 C13 C15 C16 -178.1(3) . . . . ? C14 C13 C15 C16 0.4(4) . . . . ? C12 C13 C15 C20 2.0(4) . . . . ? C14 C13 C15 C20 -179.4(3) . . . . ? C20 C15 C16 C17 -0.2(4) . . . . ? C13 C15 C16 C17 179.9(3) . . . . ? C15 C16 C17 C18 0.0(5) . . . . ? C16 C17 C18 C19 0.6(4) . . . . ? C16 C17 C18 C21 179.6(3) . . . . ? C21 C18 C19 C20 180.0(3) . . . . ? C17 C18 C19 C20 -1.1(4) . . . . ? C18 C19 C20 C15 0.8(4) . . . . ? C16 C15 C20 C19 -0.2(4) . . . . ? C13 C15 C20 C19 179.7(3) . . . . ? C19 C18 C21 C22 -1.0(4) . . . . ? C17 C18 C21 C22 -180.0(3) . . . . ? C19 C18 C21 C23 177.8(3) . . . . ? C17 C18 C21 C23 -1.1(5) . . . . ? C18 C21 C22 N3 -129(10) . . . . ? C23 C21 C22 N3 53(10) . . . . ? C22 C21 C23 N4 76(21) . . . . ? C18 C21 C23 N4 -103(21) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.562 _refine_diff_density_min -0.560 _refine_diff_density_rms 0.083 #==END