N-(4-Ethoxyphenyl)-3-oxobutanamide

Abstract

The title compound, C12H15NO3, crystallizes with Z′ = 2 in space group Pca21 with the two independent molecules having almost the same conformation, differing mostly at the end of the butanamide chain. A local inversion center near 1/8, 3/4, z relates the two molecules, as is common for structures in this space group with Z′ = 2. The molecule crystallizes as the keto tautomer, and the β-diketone moieties are twisted out of planarity, with O—C...C—O pseudo torsion angles of −74.4 (5) and −83.9 (5)°. The N—H group of each independent molecule donates an intermolecular hydrogen bond to an amide carbonyl oxygen atom by positive or negative translations along the b axis, thus forming antiparallel chains propagating in the [010] direction.

Keywords

• crystal structure
• metabolic intermediates
• nonopiod analgesics
• phenacetin congeners