Research Article: 2-{[3-Methyl-4-(2,2,2-trifluoro­eth­oxy)pyridin-2-yl]methyl­sulfan­yl}-1H-benzimidazole monohydrate: a monoclinic polymorph

Date Published: July 01, 2012

Publisher: International Union of Crystallography

Author(s): Yu-Feng Chen, Jin-Yao Chen, Ming-Huang Hong, Jie Lu, Guo-Bin Ren.


The title compound, C16H14F3N3OS·H2O, which had been previously characterized in the space group P-1 [Ren et al. (2011 ▶). Acta Cryst. E67, o270], has now been crystallized from 1-propanol in the monoclinic form in the space group P21/c. While the triclinic form is a Z′ = 2 crystal, the new monoclinic polymorph includes one main mol­ecule and one water lattice mol­ecule in the asymmetric unit. In the crystal, the water mol­ecule is sandwiched between neighboring main mol­ecules and behaves as both donor and acceptor in O—H⋯N and N—H⋯O hydrogen bonds with the imidazole N atoms. This pattern of chains parallel to [100] further inter­acts via O—H⋯N(pyridine) contacts.

Partial Text

For the role of the title compound in the synthesis of the anti-ulcer drug lansoprazole {systematic name: (RS)-2-([3-methyl-4-(2,2,2-trifluoro­eth­oxy)pyridin-2-yl]methyl­sulfin­yl)-1H-benzo[d]imidazole}, see: Del Rio et al. (2007 ▶); Reddy et al. (2008 ▶); Iwahi et al. (1991 ▶). For related structures, see: Swamy & Ravikumar (2007 ▶); Hakim Al-arique et al. (2010 ▶). For the triclinic polymorph of the title hydrate, see: Ren et al. (2011 ▶) and for the structure of the propan-2-ol solvo-polymorph, see: Ma et al. (2012 ▶)




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