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Acta Crystallogr C. 2013 May;69(Pt 5):522-5. doi: 10.1107/S0108270113007889. Epub 2013 Apr 9.

Isomeric 3- and 4-chloro-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline.

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  • 1College of Chemistry and Chemical Engineering, Xi'an ShiYou University, Xi'an, Shaanxi 710065, People's Republic of China.


The title isomers, namely 3-chloro-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline, (I), and 4-chloro-N-[1-(1H-pyrrol-2-yl)ethylidene]aniline, (II), both C12H11ClN2, differ in the position of the chlorine substitution. Both compounds have the basic iminopyrrole structure, which shows a planar backbone with similar features. The dihedral angle formed by the planes of the pyrrole and benzene rings is 75.65 (7)° for (I) and 86.56 (8)° for (II). The H atom bound to the pyrrole N atom is positionally disordered and partial protonation occurs at the imino N atom in (I), while this phenomenon is absent from the structure of (II). Packing interactions for both compounds include intermolecular N-H···N hydrogen bonds and C-H···π interactions, forming centrosymmetric dimers for both (I) and (II).

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