5-(Adamantan-1-yl)-3-anilinomethyl-2,3-dihydro-1,3,4-oxadiazole-2-thione

In the title compound, C19H23N3OS, the oxadiazole and benzene rings are inclined at a dihedral angle of 50.30 (11)°, with the major twist between them occurring at the ring–methylene N—C bond [N—N—C—N torsion angle = −101.2 (2)°]. In the crystal, helical supramolecular chains along [010] are sustained by N—H⋯S hydrogen bonds. These are linked into layers lying parallel to (-101) by methylene–phenyl C—H⋯π interactions.

In the title compound, C 19 H 23 N 3 OS, the oxadiazole and benzene rings are inclined at a dihedral angle of 50.30 (11) , with the major twist between them occurring at the ringmethylene N-C bond [N-N-C-N torsion angle = À101.2 (2) ]. In the crystal, helical supramolecular chains along [010] are sustained by N-HÁ Á ÁS hydrogen bonds. These are linked into layers lying parallel to (101) by methylenephenyl C-HÁ Á Á interactions.

Experimental
Cg1 is the centroid of the C14-C19 ring.

Tiekink Comment
In continuation of our long-term interest in the chemical and pharmacological properties of adamantane derivatives (El-Emam & Ibrahim, 1991;El-Emam et al., 2004), including structural studies (Al-Tamimi et al., 2013), we describe herein the X-ray crystal structure determination of the title compound, (I).

Experimental
A mixture of 5-(adamantane-1-yl)-1,3,4-oxadiazole-2-thiol (2.36 g, 0.01 mol), aniline (0.93 g, 0.01 mol) and 37% formaldehyde solution (1.5 ml), in ethanol (15 ml), was stirred at room temperature for 2 h and allowed to stand overnight. The precipitated crude product was filtered, washed with water, dried, and crystallized from ethanol to yield  The molecular structure of (I) showing displacement ellipsoids at the 35% probability level.  View of the unit-cell contents in projection down the b axis of (I). The N-H···S and C-H···π interactions are shown as orange and purple dashed lines, respectively.

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.