Raltegravir monohydrate

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].