In the title compound, racemic bucetin [systematic name: N-(4-ethoxyphenyl)-3-hydroxybutanamide], C12H17NO3, the molecule is in an extended conformation as illustrated by the C—O—C—C torsion angle [170.14 (15)°] in the ethoxy group and the subsequent C—N—C—C [−177.24 (16)°], N—C—C—C [170.08 (15)°] and C—C—C—C [171.41 (15)°] torsion angles in the butanamide chain. In the crystal, the O—H group donates an intermolecular O—H...O hydrogen bond to the amide carbonyl oxygen atom and also accepts an intermolecular N—H...O hydrogen bond from an adjacent N—H group. The former forms 12-membered dimeric rings about inversion centers, and the latter form chains in the [001] direction. The overall hydrogen-bonded network is two-dimensional, with no propagation in the [100] direction.
In the title compound, C9H10N2O4, the three substituents vary in the degree of lack of planarity with the central phenyl ring. The methoxy group is nearest to being coplanar, with a C—C—O—C torsion angle of 6.1 (5)°. The nitro group is less coplanar, with a 12.8 (5)° twist about the C—N bond and the acetamido group is considerably less coplanar with the central ring, having a 25.4 (5)° twist about the C—N bond to the ring. The NH group forms an intramolecular N—H...O hydrogen bond to a nitro-group O atom.
The title compound, C8H8N2O4, differs in its degree of planarity from the 3-nitro isomer and also in its hydrogen-bonding pattern. Its NH group forms an intramolecular hydrogen bond to a nitro oxygen atom, and its OH group forms an intermolecular hydrogen bond to an amide oxygen atom, generating [10\overline{1}] chains in the crystal.
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