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

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].

The financial support of the Research Center for Female Scientific and Medical Colleges, King Saud University, is greatly appreciated. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/ 12).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6828).

Tiekink Comment
In continuation to our interest in the chemical and pharmacological properties of adamantane derivatives, and as part of on-going structural studies (El-Emam et al., 2012), the title compound (I) was synthesized as potential chemotherapeutic agent (Al-Omar et al., 2010).
The precipitated crude product was filtered, washed with water, dried, and crystallized from ethanol to yield 434 mg

Figure 1
The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.