Structures of (pyrazinecarbonyl)hydrazones of substituted benzaldehydes: different supramolecular arrangements from C H•••X (X = O, N, ?) hydrogen bonds

Authors: Howie, R.A.; Lima, C.H.S.; Kaiser, C.R.; De Souza, M.V.N.; Wardell, J.L.; Wardell, S.M.S.V.


Abstract

The crystal structures of six (pyrazinecarbonyl)hydrazone di-substituted benzaldehyde derivatives [N2C4H3CONHN = CHC6H3XY: X,Y = 2,3-Cl2; 2,3-(MeO)2; 2,4-F2; 2,4-Me2; 3-HO—4-MeO; 3-MeO—4-HO] and one tri-substituted benzaldehyde derivative, [N2C4H3CONHN = CHC6H2X3: X3 = 3,4,5-(MeO)3] are reported. In all cases extensive intermolecular C—H···X (X = O, N or π-ring) hydrogen-bonding is present in which the the oxygen atoms of OH and OMe substituents act as hydrogen-bond acceptors and C—H bonds of methyl groups act as hydrogen-bond donors. The connectivity attained is one-dimensional in chains or ribbons in the 2,3-(OMe)2 and 2,4-Me2 derivatives, three dimensional only in the case of the 3-MeO—4-HO derivative and two dimensional in layers of molecules otherwise. It is concluded, therefore, that the bulky nature of the substituents limits the connectivity attainable in this series of compounds.
Keywords: (pyrazinecarbonyl)hydrazone; pi … pi interactions; Hydrogen bonds Document Type: Research Article DOI: http://dx.doi.org/10.1524/zkri.2010.1235 Publication date: 16 de Abril de 2010

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