(Adamantan-1-yl)(phenyl-sulfan-yl)methanone

Abstract

Two independent mol-ecules (A and B) comprises the asymmetric unit of the title ester, C(17)H(20)OS. The phenyl ring is inclined with respect to the thio-carboxyl group, forming dihedral angles of 58.95 (6) (in mol-ecule A) and 62.28 (6)° (in mol-ecule B). In each independent mol-ecule, one adamantyl methyl-ene C atom is nearly coplanar with the thio-carboxyl group. The major difference between mol-ecules A and B relates to the relationship between the S atom and the coplanar adamantyl methyl-ene C atom [C(a)-C(q)-C(c)-S torsion angles = 178.25 (8) and 6.81 (13)°, respectively; C(a) = adamantyl methyl-ene C atom, C(q) = quaternary C atom and C(c) = carbonyl C atom], whereby the S atom in mol-ecule A has an anti relationship with the methyl-ene C atom and in mol-ecule B, the S atom is syn. In the crystal, C-H⋯π inter-actions are formed leading to supra-molecular layers in the ac plane.

Fig. 1.

The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level.

Fig. 2.

Superimposition of the S1-containing molecule (red) and the inverted S2-containing molecule (blue) in (I). The COS moieties have been superimposed.

Fig. 3.

A view in projection down the a axis of the unit-cell contents for (I). The C—H···π interactions are shown as purple dashed lines.