Crystal structure of N-(3-oxo­butano­yl)-l-homoserine lactone

The structure and absolute configuration of the title compound, C(8)H(11)NO(4), which is a known quorum-sensing modulator, have been determined. The mol­ecule exhibits signs of an intra­molecular attractive carbon­yl–carbonyl n→π* inter­action between the amide and lactone ester groups, specifically – a short contact of 2.709 (2) Å between the amide oxygen atom and ester carbon atom, approach of the amide oxygen atom to the ester carbonyl group along the Bürgi–Dunitz trajectory, at 99.1 (1)°, and pyramidalization of the ester carbonyl group by 1.1 (1)°. Moreover, a similar n→π* inter­action is observed for the amide carbonyl group approached by the ketone oxygen donor. These inter­actions apparently affect the conformation of the uncomplexed mol­ecule, which adopts a different shape when bound to protein receptors. In the crystal, the mol­ecules form translational chains along the a axis via N—H⋯O hydrogen bonds.