Research Article: (1-Adamant­yl)(4-amino­phen­yl)methanol

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.

Partial Text

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 ▶).




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