Crystal structure of N-[(naphthalen-1-yl)carbamo-thio-yl]cyclo-hexa-necarboxamide.

ABSTRACT

The title compound, C18H20N2OS, displays whole-mol-ecule disorder over two adjacent sets of sites with an occupancy ratio of 0.630 (11)0.370 (11). In each disorder component, the cyclo-hexyl ring shows a chair conformation with the exocyclic C-C bond in an equatorial orientation. The dihedral angles between the cyclo-hexyl ring (all atoms) and the naphthyl ring system are 36.9 (6) for the major component and 20.7 (12)° for the minor component. Each component features an intra-molecular N-H⋯O hydrogen bond, which closes an S(5) ring. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R (2) 2(8) loops for both components. Aromatic π-π stacking inter-actions [shortest centroid-centroid separation = 3.593 (9) Å] and a C-H⋯π inter-action are also observed.