Date Published: May 01, 2009
Publisher: International Union of Crystallography
Author(s): Michal Rouchal, Marek Nečas, Robert Vícha.
In the racemic crystal of the title compound, C17H23NO, enantiomers of the two crystallographically independent molecules are linked into face-to-face RSdimers via intermolecular O—H⋯N hydrogen bonds and π–π interactions with centroid–centroid distances of 3.7610 (2) Å. The molecules adopt slightly different conformations and contain an adamantane cage consisting of three fused cyclohexane rings in almost ideal chair conformations, with C—C—C angles varying within the range 107.2 (4)–111.4 (4)°. In the hydrogen-bonded pair, the benzene rings are almost coplanar, the dihedral angle between them being 1.29 (13)°. The molecular packing in the crystal is stabilized by additional intermolecular N—H⋯O hydrogen bonds.
The title compound was prepared according to a modification of the procedure of Adkins & Billica (1948 ▶). For some important properties of adamantane-bearing compounds, see: Cromwell et al. (1985 ▶), van Bommel et al. (2001 ▶).