Crystal structures ofN-tert-butyl-3-(4-fluorophenyl)-5-oxo-4-[2-(trifluoromethoxy)phenyl]-2,5-dihydrofuran-2-carboxamide and 4-(2H-1,3-benzodioxol-5-yl)-N-cyclohexyl-5-oxo-3-[4-(trifluoromethyl)phenyl]-2,5-dihydrofuran-2-carboxamide

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

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Supramolecular synthons in the gamma-hydroxybutenolides

Rosa

Manna

Soriente

et al. 2017

CrystEngComm

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Crystal structures ofN-tert-butyl-3-(4-fluorophenyl)-5-oxo-4-[2-(trifluoromethoxy)phenyl]-2,5-dihydrofuran-2-carboxamide and 4-(2H-1,3-benzodioxol-5-yl)-N-cyclohexyl-5-oxo-3-[4-(trifluoromethyl)phenyl]-2,5-dihydrofuran-2-carboxamide

Abstract: The structures of two butenolide derivatives are reported. The conformations are differ largely in the orientation of the amide carbonyl atom.

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References 14 publications

Supramolecular synthons in the gamma-hydroxybutenolides

Supramolecular synthons in the gamma-hydroxybutenolides

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