Crystal structure and biological evaluation of 4-methylmorpholin-4-ium 1,3-dimethyl-2,6-dioxo-5-(2,4,6-trinitrophenyl)-1,2,3,6-tetrahydropyrimidin-4-olate

Abstract

The title molecular salt, C5H12NO+·C12H8N5O9− [common name: 4-methylmorpholin-4-ium 1,3-dimethyl-5-(2,4,6-trinitrophenyl)barbiturate], possesses noticeable anticonvulsant and hypnotic activity. In the anion, the 1,3-dimethylbarbituric acid ring and the symmetrically substituted trinitrophenyl ring, linked via a C—C bond, are not coplanar but subtend an angle of 44.88 (7)°. The six-membered ring of the 4-methylmorpholin-4-ium cation has a chair conformation. In the crystal, the cation and anion are linked via an N—H...O hydrogen bond. The cation–anion units are linked by a number of C—H...O hydrogen bonds, forming a three-dimensional network.

Keywords

• crystal structure
• anticonvulsant activity
• hypnotic activity
• barbiturate
• molecular salt
• hydrogen bonding