Research Article: 3-(Adamantan-1-yl)-4-[(E)-(2,6-difluoro­benzyl­idene)amino]-1-[(4-phenyl­piperazin-1-yl)meth­yl]-1H-1,2,4-triazole-5(4H)-thione

Date Published: July 01, 2012

Publisher: International Union of Crystallography

Author(s): Ali A. El-Emam, Ebtehal S. Al-Abdullah, Nasser R. El-Brollosy, Seik Weng Ng, Edward R. T. Tiekink.


The imine residue [C=N = 1.268 (3) Å; conformation = E] is twisted [N—N—C—N = 87.8 (2)°] out of the plane (r.m.s. deviation = 0.016 Å) of the central 1,2,4-triazole ring in the title compound, C30H34F2N6S. A small twist also occurs between the imine and terminal benzene rings [N—C—C—C = −169.8 (2)°]. The piperazine ring (chair conformation) occupies a position almost normal to the central plane [N—N—C—N = 87.8 (2)°]. In the crystal, the mol­ecules are consolidated into a three-dimensional architecture via C—H⋯S, C—H⋯π and π–π inter­actions, the latter between centrosymmetrically related difluoro­benzene rings [inter-centroid distance = 3.9389 (18) Å].

Partial Text

For a related structure and background to the biological activity of adamantane derivatives, see: El-Emam et al. (2012 ▶). For further synthetic details, see: Al-Omar et al. (2010 ▶).




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