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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.

SUBMITTER: Zhou XB

PROVIDER: S-EPMC4571347 | biostudies-literature | 2015 Aug

REPOSITORIES: biostudies-literature

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Crystal structures of vortioxetine and its methanol monosolvate.

Zhou Xin-Bo XB Gu Jian-Ming JM Sun Meng-Ying MY Hu Xiu-Rong XR Wu Su-Xiang SX

Acta crystallographica. Section E, Crystallographic communications 20150704 Pt 8

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 correspondi ...[more]

PMID: 26396746

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