Comparison of the structure of ( )-2-(2-benzylidenehydrazinylidene)quinoxaline with those of its chloro- and bromobenzylidene analogues

Authors: Gomes, L.R.; Low, J.N.; Rodrigues, A.S.M.C.; Wardell, J.L.; De Souza, M.V.N.; Nogueira, T.C.M.; Pinheiro, A.C.


Abstract

(E)-2-(2-Benzylidenehydrazinylidene)quin­oxaline, C15H12N4, crystallized with two molecules in the asymmetric unit. The structures of six halogen derivatives of this compound were also investigated: (E)-2-[2-(2-chlorobenzylidene)hydrazinyl­idene]quinoxaline, C15H11ClN4; (E)-2-[2-(3-chlorobenzylidene)hydrazinylidene]quinoxaline, C15H11ClN4; (E)-2-[2-(4-chlorobenzylidene)hydrazinylidene]quinoxaline, C15H11ClN4; (E)-2-[2-(2-bromobenzylidene)hydrazinylidene]quinoxaline, C15H11BrN4; (E)-2-[2-(3-bromobenzylidene)hydrazinylidene]quino­xaline, C15H11BrN4; (E)-2-[2-(4-bromobenzylidene)hydrazin­yl­idene]quinoxaline, C15H11BrN4. The 3-Cl and 3-Br com­pounds are isomorphous, as are the 4-Cl and 4-Br compounds. In all of these compounds, it was found that the supramolecular structures are governed by similar predominant patterns, viz. strong intermolecular N-H...N(pyrazine) hydrogen bonds supplemented by weak C-H...N(pyrazine) hydro­gen-bond interactions in the 2- and 3-halo compounds and by C-H...Cl/Br interactions in the 4-halo compounds. In all compounds, there are [pi][pi] stacking interactions.
Keywords: NoneDocument Type: Research ArticleDOI: http://dx.doi.org/10.1107/S0108270113015370Publication date: 13 de Julho de 2013

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