Lone-Pair Repulsion in Cyclic Hydroxamic Acid O-Esters: N-Cyclohexyloxy-2(1H)-pyridone

The solid-state geometry of the title compound, C₁₁H₁₅NO₂, shows a planar pyridone ring. The carbocyclic ring adopts a chair conformation with its substituent located in an axial position. The alkyl substituent of the title compound is twisted by 79.0 (2)° out of the heterocyclic plane. These findings may be interpreted as a consequence of lone-pair repulsion on the adjacent N and O heteroatoms in the hydroxamate moiety. This repulsion will be at its maximum if the C-N-O-C atoms form a plane.

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