Crystal structure of lansoprazole sulfone

The structure of 2-({[3-methyl-4-(2,2,2-trifluoroethoxy)-2-pyridinyl]methyl} sulfonyl)-1H-1,3-benzimidazole, C16H14N3O3F3S, has been solved. The compound belongs to the monoclinic space group (P21/c) with cell parameters a = 8.8693(9) Å, b = 23.369(2) Å, c = 8.6141(8) Å, β = 104.68(1)°, V = 1727.2(3) Å3, Z = 4. The final R and wR(F2) values were 0.070 and 0.147, respectively. The title molecule has a ‘Z’ shape in the crystal structure. The fused benzimidazole moiety and the pyridine ring are nearly coplanar. The molecules are linked by N-H…N and C-H…O hydrogen bonds into chains of edge-fused R22 (14), R22 R22 (8), and R22 (18) rings along the c-axis. The crystal lattice is further strengthened by π-π stacking interactions.