Lamivudine hemihydrate.

A new lamivudine hydrate, namely, cis-4-amino-1-(2-hydroxymethyl-1,3-oxathiolan-5-yl)pyrimidin-2(1H)-one hemihydrate, C(8)H(11)N(3)O(3)S.0.5H(2)O, has been synthesized and structurally characterized by both powder and single-crystal X-ray diffraction studies. The hemihydrate crystallizes in the Sohnke space group P2(1), with the asymmetric unit comprising four lamivudine and two water molecules. An extensive network of intermolecular hydrogen bonds involving both lamivudine and solvent water molecules generates a three-dimensional supramolecular architecture. The structural data and crystal packing of the present lamivudine hemihydrate are compared with those of other hydrated and anhydrous forms of lamivudine.