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The title compound, C12H12N203, is composed of a nitroanilino moiety and a cyclic c~,/3-unsaturated ketone moiety. The nitro group is oriented anti to the carbonyl group and the cyclic ketone ring is in a puckered conformation with C9 as the out-of-plane atom. The shortened C ll~N2 and C7---C12 bond lengths suggest that the amino group is conjugated with the c~,/3-unsaturated ketone group. Intermolecular hydrogen bonds between the carbonyl O atom and the amino group link the molecules into infinite chains [N--H 0.88 (3) CommentHydrogen-bond directed co-crystallization has been demonstrated as a useful way to study the molecular recognition and hydrogen-bond properties of a class of related host molecules (Etter & Baures, 1988; Etter, Urbanczyk-Lipkowska, Zia-Ebrahimi & Panunto, 1990;Etter & Reutzel, 1991). As part of a comprehensive study of the hydrogen-bond properties of nitroanilines (Panunto, Urbanczyk-Lipkowska, Johnson & Etter, 1987;Etter & Huang, 1992), the title compound, (I), was obtained unexpectedly during an attempt to prepare an m-nitroaniline/1,3-cyclohexanedione co-crystal. The reaction is believed to proceed by a standard enamine formation in which nucleophilic addition to the carbonyl group of 1,3-cyclohexanedione by the amino group of m-nitroaniline is followed by dehydration, as shown in the scheme below.o o•

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