3-(Adamantan-1-yl)-4-methyl-1-[(4-phenylpiperazin-1-yl)methyl]-1H-1,2,4-triazole-5(4H)-thione dichloromethane hemisolvate

The asymmetric unit of the title dichloromethane hemisolvate, C24H33N5S·0.5CH2Cl2, comprises an adamantanyl/triazole derivative and half a CH2Cl2 molecule of crystallization; the latter is disordered about a twofold axis of symmetry. The piperazine ring has a chair conformation and the two N-bound substituents occupy equatorial positions. The piperazine residue is almost normal to the triazole ring [N—N—C—N torsion angle = −79.9 (3)°] so that to a first approximation, the molecule has an L-shape. Linear supramolecular chains parallel to [001] are formed via C—H⋯S interactions. Two such chains are linked into a double chain via C—H⋯Cl interactions involving the disordered CH2Cl2 molecules of solvation.

The asymmetric unit of the title dichloromethane hemisolvate, C 24 H 33 N 5 SÁ0.5CH 2 Cl 2 , comprises an adamantanyl/triazole derivative and half a CH 2 Cl 2 molecule of crystallization; the latter is disordered about a twofold axis of symmetry. The piperazine ring has a chair conformation and the two N-bound substituents occupy equatorial positions. The piperazine residue is almost normal to the triazole ring [N-N-C-N torsion angle = À79.9 (3) ] so that to a first approximation, the molecule has an L-shape. Linear supramolecular chains parallel to [001] are formed via C-HÁ Á ÁS interactions. Two such chains are linked into a double chain via C-HÁ Á ÁCl interactions involving the disordered CH 2 Cl 2 molecules of solvation.

Related literature
For the diverse biological activities of adamantane derivatives, see: Al-Deeb et al. (2006); Al-Omar et al. (2010). For related adamantanyl structural studies, see: El-Emam et al. (2012a,b). For the preparation of one of the precursor molecules, see: El-Emam & Ibrahim (1991

T. Tiekink Comment
In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives, motivated by their putative biological activities (Al-Deeb et al., 2006;Al-Omar et al., 2010), and as part of on-going structural studies (El-Emam et al., 2012a,b), we synthesized the title compound (I) as a potential chemotherapeutic agent. Herein, we describe the crystal and molecular structure of (I).
The asymmetric unit of (I), Fig. 1, comprises an adamantanyl/triazole derivative and half a CH 2 Cl 2 molecule of crystallization. In the organic molecule, the piperazinyl ring has a chair conformation and the two N-bound substituents occupy equatorial positions. The piperazinyl residue is almost normal to the triazole ring with the N2-N3-C14-N4 torsion angle being -79.9 (3)°. To a first approximation, the molecule has an L-shape, as found recently in the 2-hydroxybenzylideneamino derivative (El-Emam et al., 2012a).
In the crystal packing, linear supramolecular chains parallel to [001] are formed via C-H···S interactions, Table 1.
These are linked into a double chain via C-H···Cl interactions involving the disordered CH 2 Cl 2 molecules of solvation,  Table 1.
at room temperature and the mixture was allowed to stand overnight. Cold water (5 ml) was slowly added and the mixture was stirred for 20 min. The precipitated crude product was filtered, washed with water, dried, and crystallized from ethanol to yield 635 mg (75%) of the title compound as colourless crystals. M.pt: 423-425 K. Single crystals suitable for X-ray analysis were obtained by slow evaporation of its CH 2 Cl 2 :EtOH solution held at room temperature (1:1;  (2 2 0), were omitted from the final cycles of refinement owing to poor agreement. The maximum and minimum residual electron density peaks of 0.41 and 1.00 e Å -3 , respectively, were located 0.62 Å and 0.63 Å from the Cl1 and Cl2 atoms, respectively.

Figure 1
The molecular structures of the molecules comprising (I) showing the atom-labelling scheme and displacement ellipsoids at the 70% probability level. The CH 2 Cl 2 molecule has 50% occupancy, being disordered over a twofold axis.  A view of the linear supramolecular double chain in (I). The C-H···S and C-H···Cl contacts are shown as orange and blue dashed lines, respectively. The CH 2 Cl 2 molecule is disordered over two position; both orientations are displayed.  (17) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. 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.