2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study

Caracelli, Ignez and Zukerman-Schpector, Julio and Schwab, Ricardo S and Silva, Everton M and Jotani, Mukesh M. and Tiekink, Edward R. T. * (2019) 2-Methyl-4-(4-nitrophenyl)but-3-yn-2-ol: crystal structure, Hirshfeld surface analysis and computational chemistry study. Acta Crystallographica Section E Crystallographic Communications, 75 (8). pp. 1232-1238. ISSN 2056-9890 (In Press)

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Abstract

The di-substituted acetylene residue in the title compound, C11H11NO3, is capped at either end by di-methylhydroxy and 4-nitrobenzene groups; the nitro substituent is close to co-planar with the ring to which it is attached [dihedral angle = 9.4 (3)]. The most prominent feature of the molecular packing is the formation, via hydroxy-O—HO(hydroxy) hydrogen bonds, of hexameric clusters about a site of symmetry 3. The aggregates are sustained by 12- membered {OH}6 synthons and have the shape of a flattened chair. The clusters are connected into a three-dimensional architecture by benzene-C—HO(nitro) interactions, involving both nitro-O atoms. The aforementioned interactions are readily identified in the calculated Hirshfeld surface. Computational chemistry indicates there is a significant energy, primarily electrostatic in nature, associated with the hydroxy-O—HO(hydroxy) hydrogen bonds. Dispersion forces are more important in the other identified but, weaker intermolecular contacts.

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