(1-Adamantyl)(4-aminophenyl)methanol

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.

In the racemic crystal of the title compound, C 17 H 23 NO, enantiomers of the two crystallographically independent molecules are linked into face-to-face RSdimers via intermolecular O-HÁ Á ÁN hydrogen bonds andinteractions 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 hydrogenbonded 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-HÁ Á ÁO hydrogen bonds.

Comment
The title molecule belongs in the family of promising compounds destined for drugs improvement. Two contrary properties playing significant role in drug design may be modulated by introduction of suitable adamantane-bearing building block into the molecule. The lipophilic adamantane cage itself may increase solubility in non-polar systems (e.g. cell membranes), whereas the solubility in polar medium may be enhanced by the formation of non-covalent inclusion complex of adamantane cage with cyclodextrins (Cromwell et al. (1985), van Bommel et al. (2001)).

Experimental
The title compound was prepared according to a modified literature procedure (Adkins & Billica, 1948). 1-Adamantyl-(4nitrophenyl)methanol (0.35 mmol, 100 mg) was dissolved in 2 cm 3 of dioxane and large excess of Raney nickel was added in one portion to this solution. The reaction mixture was vigorously stirred under H 2 atmosphere at room temperature. After the consumption of all starting material (according to TLC), the mixture was diluted with 5 cm 3 of water. The water layer was sequentially washed five times with 10 cm 3 of diethyl ether. The combined organic layers were dried over sodium sulfate and evaporated in vacuum. After the purification of crude product by column chromatography (silica gel; petroleum ether/ethyl acetate, v/v, 1/1), the desired product was obtained as a pale yellow crystalline powder (88.3 mg, 98%, mp 143-146°C).
The single crystals suitable for X-ray analysis were grown by spontaneous evaporation from deuterochloroform at room temperature.

Refinement
Although several methods, solvents and conditions for crystal growth were tested, the best obtained sample consisted of poor quality crystals affording only a low quality data set. Thus the precision of refined parameters is lowered accordingly.
The analysis of the most disagreeable reflections suggested no significant systematic trends which could be attributed to twinning (application of a twin law provided merely negligible improvement in precision) or experimental failures. The H supplementary materials sup-2 atoms were constrained using standard SHELXL facilities with the exceptions of NH 2 H atoms which were positioned from the diference Fourier map and refined fully. Fig. 1. ORTEP of the asymmetric unit with atoms represented as 50% probability ellipsoids and H atoms are shown as small spheres at arbitrary radii. (1-Adamantyl)(4-aminophenyl)methanol