Abstract
In 2,2'-bipyridin-1-ium 1,1,3,3-tetra-cyano-2-eth-oxy-prop-2-en-1-ide, C10H9N2 (+)·C9H5N4O(-), (I), the ethyl group in the anion is disordered over two sets of atomic sites with occupancies 0.634 (9) and 0.366 (9), and the dihedral angle between the ring planes in the cation is 2.11 (7)°. The two independent C(CN)2 groups in the anion make dihedral angles of 10.60 (6) and 12.44 (4)° with the central propenide unit, and the bond distances in the anion provide evidence for extensive electronic delocalization. In bis-(2,2'-bipyridin-1-ium) 1,1,3,3-tetra-cyano-2-(di-cyano-methyl-ene)propane-1,3-diide [alternative name bis-(2,2'-bipyridin-1-ium) tris-(di-cyano-methyl-ene)methane-diide], 2C10H9N2 (+)·C10N6 (2-) (II), the dihedral angles between the ring planes in the two independent cations are 7.7 (2) and 10.92 (17)°. The anion exhibits approximate C 3 symmetry, consistent with extensive electronic delocalization, and the three independent C(CN)2 groups make dihedral angles of 23.8 (2), 27.0 (3) and 27.4 (2)° with the central plane. The ions in (I) are linked by an N-H⋯N hydrogen bond and the resulting ion pairs are linked by two independent C-H⋯N hydrogen bonds, forming a ribbon containing alternating R 4 (4)(18) and R 4 (4)(26) rings, where both ring types are centrosymmetric. The ions in (II) are linked by two independent N-H⋯N hydrogen bonds and the resulting ion triplets are linked by a C-H⋯N hydrogen bond, forming a C 2 (1)(7) chain containing anions and only one type of cation, with the other cation linked to the chain by a further C-H⋯N hydrogen bond.
Highlights
Laboratoire de Chimie, Ingénierie Moléculaire et Nanostructures (LCIMN), Université Ferhat Abbas Sétif 1, Sétif 19000, Algeria, bUnité de Recherche de Chimie de l’Environnement et, Moléculaire Structurale (CHEMS), Université Constantine
Polynitrile anions have received considerable attention recently because of their importance in both coordination chemistry and in molecular materials chemistry (Miyazaki et al, 2003; Batten & Murray, 2003; Benmansour et al, 2007; Setifi, Domasevitch et al, 2013; Setifi, Setifi et al, 2013; Setifi, Lehchili et al, 2014). These organic anions are interesting for their extensive electronic delocalization, and for their structural versatility, in particular the potential to utilize a variety of coordination modes, including their action as bridging ligands between metal centres in 2, 3- or 4- modes, so forming polymeric assemblies which can be one, two- or three-dimensional
We have recently reported the structures of several salts containing the 2-ethoxy-1,1,3,3-tetracyanopropenide anion, including salts with the bis(2,20 -bi-1H-imidazole)copper(II)
Summary
Polynitrile anions have received considerable attention recently because of their importance in both coordination chemistry and in molecular materials chemistry (Miyazaki et al, 2003; Batten & Murray, 2003; Benmansour et al, 2007; Setifi, Domasevitch et al, 2013; Setifi, Setifi et al, 2013; Setifi, Lehchili et al, 2014) These organic anions are interesting for their extensive electronic delocalization, and for their structural versatility, in particular the potential to utilize a variety of coordination modes, including their action as bridging ligands between metal centres in 2-, 3- or 4- modes, so forming polymeric assemblies which can be one-, two- or three-dimensional. During the course of attempts to prepare such complexes, using the anions 1,1,3,3-tetracyano-2-ethoxypropenide (tcnoet) and tris(dicyanomethylene)methanediide (tcpd), we isolated the two title compounds whose structures are described here
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