Raltegravir monohydrate

Abstract

The hydrated title compound [systematic name:N-(4-fluorobenzyl)-5-hydroxy-1-methyl-2-{1-methyl-1-[(5-methyl-1,3,4-oxadiazol-2-ylcarbonyl)amino]ethyl}-6-oxo-1,6-dihydropyrimidine-4-carboxamide monohydrate], C20H21FN6O5·H2O, is recognised as the first HIV integrase inhibitor. In the molecule, the dihedral angles between the mean planes of the pyrimidine ring and the phenyl and oxadiazole rings are 72.0 (1) and 61.8 (3)°, respectively. The mean plane of the oxadiazole ring is twisted by 15.6 (3)° from that of the benzene ring, while the mean plane of amide group bound to the oxadiaole ring is twisted by 18.8 (3)° from its mean plane. Intramolecular O—H...O and C—H...N hydrogen bonds are observed in the molecule. The crystal packing features O—H...O hydrogen bonds, which include bifurcated O—H...(O,O) hydrogen bonds from one H atom of the water molecule. In addition, N—H...O hydrogen bonds are observed involving the two amide groups. These interactions link the molecules into chains along [010].