Acta Crystallographica Section C

Crystal Structure Communications

Volume 69, Part 8 (August 2013)


organic compounds



Acta Cryst. (2013). C69, 920-926    [ doi:10.1107/S0108270113015370 ]

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

L. R. Gomes, J. N. Low, A. S. M. C. Rodrigues, J. L. Wardell, M. V. N. de Souza, T. C. M. Noguiera and A. C. Pinheiro

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.

Formula: C15H12N4, C15H11ClN4, C15H11ClN4, C15H11ClN4, C15H11BrN4, C15H11BrN4 and C15H11BrN4

Keywords: crystal structure; quinoxalines; hydrogen bonding.


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Structure factor file (CIF format) (268.3 kbytes)
[ doi:10.1107/S0108270113015370/sk34881sup2.hkl ]
Contains datablock 1


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Structure factor file (CIF format) (140.1 kbytes)
[ doi:10.1107/S0108270113015370/sk34882asup3.hkl ]
Contains datablock 2a


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Structure factor file (CIF format) (111.3 kbytes)
[ doi:10.1107/S0108270113015370/sk34882bsup4.hkl ]
Contains datablock 2b


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Structure factor file (CIF format) (148.8 kbytes)
[ doi:10.1107/S0108270113015370/sk34882csup5.hkl ]
Contains datablock 2c


hkldisplay filedownload file

Structure factor file (CIF format) (180.8 kbytes)
[ doi:10.1107/S0108270113015370/sk34883asup6.hkl ]
Contains datablock 3a


hkldisplay filedownload file

Structure factor file (CIF format) (149.1 kbytes)
[ doi:10.1107/S0108270113015370/sk34883bsup7.hkl ]
Contains datablock 3b


hkldisplay filedownload file

Structure factor file (CIF format) (118.2 kbytes)
[ doi:10.1107/S0108270113015370/sk34883csup8.hkl ]
Contains datablock 3c


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