title: Crystal structures of vortioxetine and its methanol monosolvate.
abstract: Vortioxetine, C18H22N2S, (1), systematic name 1-{2-[(2,4-di-methyl-phen-yl)sulfan-yl]phen-yl}piperazine, a new drug used to treat patients with major depressive disorder, has been crystallized as the free base and its methanol monosolvate, C18H22N2S·CH3OH, (2). In both structures, the vortioxetine mol-ecules have similar conformations: in (1), the dihedral angle between the aromatic rings is 80.04 (16)° and in (2) it is 84.94 (13)°. The C-S-C bond angle in (1) is 102.76 (14)° and the corresponding angle in (2) is 103.41 (11)°. The piperazine ring adopts a chair conformation with the exocyclic N-C bond in a pseudo-equatorial orientation in both structures. No directional inter-actions beyond normal van der Waals contacts could be identified in the crystal of (1), whereas in (2), the vortioxetine and methanol mol-ecules are linked by N-H⋯O and O-H⋯N hydrogen bonds, generating [001] chains.
authors.affiliation: College of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, Zhejiang 310053, People's Republic of China.
authors.forename: Xin-Bo
authors.initials: XB
authors.lastname: Zhou
authors.affiliation: Center of Analysis and Measurement, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China.
authors.forename: Jian-Ming
authors.initials: JM
authors.lastname: Gu
authors.affiliation: College of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, Zhejiang 310053, People's Republic of China.
authors.forename: Meng-Ying
authors.initials: MY
authors.lastname: Sun
authors.affiliation: Chemistry Department, Zhejiang University, Hangzhou, Zhejiang 310028, People's Republic of China.
authors.forename: Xiu-Rong
authors.initials: XR
authors.lastname: Hu
authors.affiliation: College of Pharmaceutical Science, Zhejiang Chinese Medical University, Hangzhou, Zhejiang 310053, People's Republic of China.
authors.forename: Su-Xiang
authors.initials: SX
authors.lastname: Wu
keywords: crystal structure; hydrogen bonding; major depressive disorder; vortioxetine