5-(Adamantan-1-yl)-3-[(2-methoxyethyl)sulfanyl]-4-phenyl-4H-1,2,4-triazole

In the title adamantyl derivative, C21H27N3OS, the terminal methoxyethyl unit is disordered over two orientations with a refined site-occupancy ratio of 0.846 (6):0.154 (6). The 1,2,4-triazole ring is statistically planar [r.m.s. deviation = 0.002 (2) Å] and the phenyl substituent is almost perpendicular to its mean plane [dihedral angle = 83.57 (11)°]. No directional intermolecular interactions were observed in the crystal structure.


Kun Fun Comment
In continuation of our interest in the chemical and pharmacological properties of adamantane derivatives (Kadi et al., 2010), we synthesized the title compound (I) as a potential chemotherapeutic agent and herein its crystal structure is reported.
Even though no intermolecular hydrogen bond was observed in the crystal packing of (I), however the crystal packing was shown in Fig. 2 to illustrate the arrangement of the molecules.

Refinement
All H atoms were placed in calculated positions with d(C-H) = 0.93 Å for aromatic (phenyl), 0.98 Å for aromatic (adamantyl), 0.97 Å for CH 2 and 0.96 Å for CH 3 atoms. The U iso values were constrained to be 1.5U eq of the carrier atom for methyl H atoms and 1.2U eq for the remaining H atoms. The terminal methoxyethyl unit is disordered over two sites with refined site occupancies of 0.846 (6) and 0.154 (6).

Figure 1
The molecular structure of the title compound, showing 30% probability displacement ellipsoids. Open bonds show the minor disorder component.

Figure 2
The crystal packing of the title compound viewed along the b axis. Only the major component was shown. 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.