4-(3-Methyl-anilino)-N-[N-(1-methyl-ethyl)carbamo-yl]pyridinium-3-sulfon-amidate (torasemide) methanol 0.25-solvate 0.25-hydrate

Abstract

The title compound, C(16)H(20)N(4)O(3)S·0.25CH(4)O·0.25H(2)O, is a hydrate/methanol solvate of torasemide, a diuretic drug used in the treatment of hypertension. The asymmetric unit contains two torasemide mol-ecules and half-occupied methanol and water mol-ecules. It is isomorphous with the previously reported nonsolvated T-II form of torasemide. The water mol-ecules contribute to the stability of the structure by participating in an extensive system of O-H⋯O hydrogen bonds; N-H⋯N and N-H⋯O hydrogen bonds are also present. Both asymmetric mol-ecules of torasemide form inversion dimers in the crystal.

Fig. 1.

A view of the content of the asymmetric unit of (I), where the sites of the solvate water and methanol molecules have 0.50 occupancy. Displacement ellipsoids are drawn at the 50% probability level.

Fig. 2.

A view of the crystal packing in the structure of (I), in proximity of the ab face. Hydrogen bonds are denoted by dashed lines. Only hydrogen atoms involved in the formation of hydrogen bonds are shown. Chains of hydrogen–bonded molecules, parallel to the [110] direction, are formed by centrosymmetric dimers of the two types of symmetry–independent molecules (denoted by the A and B letters, respectively). The solvent molecules, not shown in this drawing, lie between this layer and the parallel one at c = 1/2, where the chains of hydrogen–bonded molecules exhibit the alternative [1–10] orientation.

Fig. 3.

The arrangement of chains, parallel to the [01–1] direction, of hydrogen–bonded molecules in proximity of the bc face. A similar arrangement, however with the alternative [011] chain orientation, exists on the parallel flanking planes at a/2 distance from the one shown.

Fig. 4.

A view of the packing in the structure of (I) showing channels hosting the solvent molecules. Dimers of A or B molecules aligned along b, according to this view, are not connected by hydrogen bonds.