rac-N-(4-Eth­oxy­phen­yl)-3-hy­droxy­butanamide

In the title compound, racemic bucetin [systematic name: N-(4-eth­oxy­phen­yl)-3-hydroxy­butanamide], C(12)H(17)NO(3), 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. [Image: see text]