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Issue 20, 2012
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The differing influence of halides upon supramolecular aggregation through C–X⋯π interactions in the crystal structures of (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H, F and Cl

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Abstract

The presence of localised C–X⋯π [or C–X⋯π(C[double bond, length as m-dash]C)] interactions are shown to be pivotal in the crystal structures of (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H (1), F (2) and Cl (3). In the absence of halide (1), molecules aggregate into supramolecular chains via alternating ten-membered {⋯HOC2N}2 and 14-membered {⋯HN2C3O}2 synthons. Molecules assemble into a three-dimensional architecture via edge-to-face C–H⋯π(arene) interactions occurring between the phenyl rings. In the presence of halide (i.e. F (2) and Cl (3) in the 4-position of the phenyl ring), two-dimensional arrays are formed by interconnected ten-membered {⋯HOC2N}2 (as seen in 1) and 24-membered {⋯HO⋯NC2OH⋯N4H}2 hydrogen bonded synthons. The latter arrangement allows for the close approach of halide to the 1,2,3-triazole ring and the formation of C–X⋯π interactions which appear to be particularly significant in the case of Cl (3), as evidenced by systematic changes (i.e. elongation) in the geometric parameters within the five-membered ring. In this series of structures, the presence of C–X⋯π interactions is shown to moderate the supramolecular aggregation based on conventional hydrogen bonding.

Graphical abstract: The differing influence of halides upon supramolecular aggregation through C–X⋯π interactions in the crystal structures of (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H, F and Cl

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Publication details

The article was received on 28 May 2012, accepted on 27 Jun 2012 and first published on 03 Jul 2012


Article type: Paper
DOI: 10.1039/C2CE25841B
Citation: CrystEngComm, 2012,14, 6534-6539

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    The differing influence of halides upon supramolecular aggregation through C–X⋯π interactions in the crystal structures of (5-methyl-1-(4-X-arylamino)-1H-1,2,3-triazol-4-yl)methanol derivatives, X = H, F and Cl

    A. K. Jordão, V. F. Ferreira, A. C. Cunha, J. L. Wardell, S. M. S. V. Wardell and E. R. T. Tiekink, CrystEngComm, 2012, 14, 6534
    DOI: 10.1039/C2CE25841B

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