N-(4-Eth-oxy-phen-yl)-3-oxobutanamide

IUCrdata. 2023 Jul 4;8(Pt 7):x230565. doi: 10.1107/S2414314623005655. eCollection 2023 Jul.

Abstract

The title compound, C12H15NO3, crystallizes with Z' = 2 in space group Pca21 with the two independent mol-ecules 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 mol-ecules, as is common for structures in this space group with Z' = 2. The mol-ecule 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 mol-ecule donates an inter-molecular hydrogen bond to an amide carbonyl oxygen atom by positive or negative translations along the b axis, thus forming anti-parallel chains propagating in the [010] direction.

Keywords: crystal structure; metabolic inter­mediates; nonopiod analgesics; phenacetin congeners.