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Supramolecular synthons in the gamma-hydroxybutenolides

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Abstract

The supramolecular organization in the solid state of five novel gamma-hydroxybutenolides is described. The functionalities on their framework drive the construction of the crystalline packing through weak non-covalent forces such as H-bonds, CH–π, π–π and CH⋯O interactions. Gamma-butenolides bearing an unsubstituted aromatic or heteroaromatic ring as the side arm exhibit a helical assembly, in which the helical sense is determined by the chirality of the molecule, promoted by a three-center, bifurcated intra-intermolecular H-bond. In this assembly, the aromatic residues form an “aromatic zipper” between adjacent homochiral helices. Crystal structures of gamma-butenolide with p-substituted aromatic rings exhibit dimers, promoted by mutual O–H⋯O[double bond, length as m-dash]C intermolecular hydrogen-bond interactions. Finally, when the p-position of the aromatic ring is occupied by a potential H-bond acceptor substituent, such as CN group, the aromatic substituent is involved in an exclusive intermolecular H-bond in the observed crystal packing. The ability of gamma-butenolides to control the type of packing induced by the substitution pattern of their side arm makes them interesting for the engineering of novel crystalline assemblies.

Graphical abstract: Supramolecular synthons in the gamma-hydroxybutenolides

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Publication details

The article was received on 18 May 2017, accepted on 24 Jul 2017 and first published on 24 Jul 2017


Article type: Paper
DOI: 10.1039/C7CE00953D
Citation: CrystEngComm, 2017, Advance Article
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    Supramolecular synthons in the gamma-hydroxybutenolides

    M. De Rosa, P. La Manna, A. Soriente, C. Gaeta, C. Talotta, N. Hickey, S. Geremia and P. Neri, CrystEngComm, 2017, Advance Article , DOI: 10.1039/C7CE00953D

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