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 (P2(1)/c) with cell parameters a = 8.8693(9) angstrom, b = 23.369(2) angstrom, c = 8.6141(8) angstrom, beta 104.68(1)degrees, V = 1727.2(3) angstrom(3), Z = 4. The final R and wR(F-2) 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 R-2(2) (14), R-2(2) R-2(2)(8), and R-2(2) (18) rings along the c-axis. The crystal lattice is further strengthened by pi-pi stacking interactions.