5-(Adamantan-1-yl)-3-(benzylsulfanyl)-4-methyl-4H-1,2,4-triazole

In the asymmetric unit of the title adamantyl derivative, C20H25N3S, there are two crystallographic independent molecules with slightly different conformations. In one molecule, the whole benzyl group is disordered over two orientations with the refined site-occupancy ratio of 0.63 (2):0.37 (2). The dihedral angles between the 1,2,4-triazole and phenyl rings are 24.3 (8) (major component) and 25.8 (13)° (minor component) in the disordered molecule, whereas the corresponding angle is 51.53 (16)° in the other molecule. In the crystal, molecules are linked into a chain along the a axis by a weak C—H⋯N interaction. Weak C—H⋯π interactions are also observed.

In the asymmetric unit of the title adamantyl derivative, C 20 H 25 N 3 S, there are two crystallographic independent molecules with slightly different conformations. In one molecule, the whole benzyl group is disordered over two orientations with the refined site-occupancy ratio of 0.63 (2):0.37 (2). The dihedral angles between the 1,2,4-triazole and phenyl rings are 24.3 (8) (major component) and 25.8 (13) (minor component) in the disordered molecule, whereas the corresponding angle is 51.53 (16) in the other molecule. In the crystal, molecules are linked into a chain along the a axis by a weak C-HÁ Á ÁN interaction. Weak C-HÁ Á Á interactions are also observed.
There are two crystallograpic independent molecules A and B in the asymmetric unit of the title adamantyl derivative, C 20 H 25 N 3 S (Fig. 1). The whole benzyl group of molecule A is disordered over two positions with the refined siteoccupancy ratio of 0.63 (2):0.37 (2) for the major and minor components. The 1,2,4-triazole ring is planar with an r.m.s.  et al., 1987) and are comparable with the related structures (Al-Abdullah et al., 2012;El-Emam et al., 2012;Fun et al., 2011).
In the crystal packing ( Fig. 2), the molecules are linked into chains along the a axis by weak C-H···N interactions (Table 1). The crystal is further stabilized by weak C-H···π interactions (Table 1).

Experimental
Sodium methylate (120 mg) was added to a solution of 5-(adamantan-1-yl)-4-methyl-4H-1,2,4-triazole-3-thiol (499 mg, 2 mmol) in absolute ethanol (10 ml) and the mixture was heated under reflux for 10 min. Benzyl bromide (342 mg, 2 mmol) was then added and the mixture was heated under reflux for 3 h. On cooling, the mixture was poured onto water (20 ml) and the precipitated crude product was filtered, washed with water and crystallized from ethanol to yield 475 mg (70%) of the title compound as colorless fine needle crystals. Colorless needle-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from chloroform/ethanol (1:1 v/v) by the slow evaporation of the solvent at room temperature after several days (m.p. 456-458 K).

Refinement
All H atoms were placed in calculated positions with C-H = 0.93 Å for aromatic ( The whole benzyl group of molecule A is disordered over two sites with refined site occupancies of 0.63 (2) and 0.37 (2).
Similarity (SAME) restraint was used for both major and minor components of the disordered group.

Figure 1
The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atom-numbering scheme. Open bond show the minor X component.

Figure 2
The crystal packing of the title compound viewed along the b axis. Only the major component and H atoms involved with the hydrogen bond were shown. Weak C-H···N interactions are shown as dashed lines.

5-(Adamantan-1-yl)-3-(benzylsulfanyl)-4-methyl-4H-1,2,4-triazole
where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max = 0.001 Δρ max = 0.30 e Å −3 Δρ min = −0.26 e Å −3 Extinction correction: SHELXTL (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.0058 (5) Special details Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.