Charge‐Transfer‐Komplexe von Tetrathiafulvalen (TTF) mit 1,2,5‐Thiadiazolchinonen

Molecular Organization of 2,1,3-Benzothiadiazoles in the Solid State

“…Representative crystallographic studies have confirmed that the atoms of C, N, and S in the 2,1,3-benzothiadiazole core are essentially coplanar and that intramolecular bonding is well represented by quinoidal structure 1 . ,,− This preference is consistent with dipole moments measured for the increasingly polarized series of analogues naphthalene, quinoxaline ( 2 ), 2,1,3-benzothiadiazole ( 1 ), and 1,2-benzoquinone ( 3 ), which are 0, 0.51, , 1.8, and 4.2 D, − respectively. Previously published structural studies show that 2,1,3-benzothiadiazoles can engage in various intermolecular interactions, including π-stacking, dipole–dipole interactions, C–H···π interactions, C–H···N interactions, and S···N interactions. ,,− S···N interactions involving benzothiadiazoles can be considered to arise from various effects, including the electrostatic attraction of opposing partial charges and the interaction of S–N σ* orbitals with nonbonding orbitals centered on N. − The strength of S···N interactions appears to be similar to that of typical hydrogen bonds and has been calculated by dispersion-corrected DFT methods to be approximately 4 kcal/mol . However, the relative importance of various interactions characteristic of 2,1,3-benzothiadiazoles remains unclear, and there are no reports of extensive efforts to use these interactions to direct the crystallization of complex 2,1,3-benzothiadiazoles in predetermined ways.…”

Unsymmetrical porphyrazines with annulated 1,2,5-thia(seleno)diazole and 3,6-diamyloxybenzene rings: synthesis, characterization and X-ray crystal structure of H2{XN2}{3,6-(OAm)2Bz}3Pz (X = S, Se)

“…diazole rings. 6 As to species 3 (the following observations are also valid for species 4), the internal substantially planar 58). The hydrogen atoms associated to the nitrogen atoms and to the isoindole units were located from a difference Fourier map, while those associated to the aliphatic chains were put in geometrically calculated positions.…”

A long symmetric N...H...N hydrogen bond in bis(4-aminopyridinium)(1+) azide(1−): redetermination from the original data

“…For the search in the Cambridge Structural Database (Groom et al, 2016), the D-H distance was set in the interval 1.30-1.45 Å and the non-bonding distance between the donor and acceptor nitrogen atoms was set in the interval 2.6-3.0 Å . (Marsh & Clemente, 2007); (c) 2,1,3-benzoselenadiazole 2,1,3-benzoselenadiazolium pentaiodide (Gieren et al, 1985) (Heravi et al, 2005); (e) bis[(3,5-dimethylpyrazole)(3,5dimethylpyrazolyl)]platinum(II) (Umakoshi et al, 2008); (f) 4-{2-(pyridin-4-yl)oxy]-1,2bis(2,3,5,6-tetrafluoro-4-iodophenyl)ethoxy}pyridin-1-ium iodide bis(nitrobenzene) (Martí-Rujas et al, 2012); (g) 5,6:14,15-dibenzo-1,4-dioxa-8-azonia-12-azacyclopentadeca-5,14-diene 5,6:14,15-dibenzo-1,4-dioxa-8,12-diazacyclopentadeca-5,14-diene perchlorate (Tušek-Božić et al, 2005); (h) dioxidotetrakis(4-methylpyridine)rhenium(V) 4methylpyridinium 4-methylpyridine diodide (Krawczyk et al, 2014); (i) 4-methylpyridinium trans-bis(-picoline)tetrakis(thiocyanato)molybdenum 4-methylpyridine (Kitanovski et al, 2009); (j) bis(4,4 0 -bipyridinium) hexakis( 2 -sulfido)tetragermaniumtetrasulfide 4,4 0 -bipyridine heptahydrate (Wang et al, 2003); (k) 4,4 0bipyridinium 4-(pyrid-4-yl)pyridinium 4,4 0 -bipyridine hexakis(isothiocyanato-N)-iron (Wei et al, 2002); (l) tris(2-benzimidazolylmethyl)ammonium 3,5-dinitrobenzoate 3,5dinitrobenzoic acid clathrate (Ji et al, 2004); (m) (2R,4S,5R)-9-(hydroxyimino)-6 0methoxycinchonan-1-ium (2R,4S,5R)-N-hydroxy-6 0 -methoxycinchonan-9-imine chloride methanol solvate (Zohri et al, 2015); (n) catena-[bis( 2 -aqua)-(5-cyano-2H-1,2,3triazole-4-carboxamide)(4-cyano-1,2,3-triazole-5-carboxamide)sodium] (Al-Azmi et al, 2007); (o) (1,1 0 -hydrogenbis{4-[1 0 -(4-pyridyl)ferrocen-1-yl]pyridine}) 4-[1 0 -(4-pyridyl)ferrocen-1-yl]pyridinium tris(5-carboxy-2-thienylcarboxylate) bis(thiophene-2,5-dicarboxylic acid) (Braga et al, 2008); (p) cytosinium 4-amino-2-hydroxybenzoate cytosine monohydrate (Cherukuvada et al, 2013); (q) cytosinium acetylenedicarboxylate cytosine monohydrate (Perumalla et al, 2013).…”