N-(2-Hydroxyethyl)-N-(tricyclo[3.3.1.13,7]dec-2-yl)benzamide

The title adamantane derivative, C19H25NO2, was synthesized as part of a study into potential antituberculosis agents. The adamantane skeleton displays shorter than normal C—C bond lengths ranging between 1.5230 (15) and 1.5329 (16) Å. The structure displays O—H⋯O hydrogen bonding and an interdigitated layered packing structure with distinct hydrophilic and hydrophobic regions.

The title adamantane derivative, C 19 H 25 NO 2 , was synthesized as part of a study into potential antituberculosis agents. The adamantane skeleton displays shorter than normal C-C bond lengths ranging between 1.5230 (15) and 1.5329 (16) Å . The structure displays O-HÁ Á ÁO hydrogen bonding and an interdigitated layered packing structure with distinct hydrophilic and hydrophobic regions.

Comment
Adamantane derivatives have been the subject of much investigation as potential anti-tubercolosis compounds (Bogatcheva et al., 2006, Lee et al., 2003. The novel compound (I) was also synthesized in order to investigate the biological activities of cage amino-alcohol compounds as potential anti-tuberculosis agents. The molecule (I) consists of a polycyclic (lipophilic) hydrocarbon skeleton with polar amine and hydroxyl units (Fig. 1).
The molecule exhibits some C-C bonds that are significantly shorter than the expected C-C bond length of 1.54 Å.
The structure exhibits intermolecular hydrogen bonding interactions between O1 and O2 of adjacent molecules (Fig. 2).
There is also a complex network of short contacts between the molecules which result in an interdigitated, layered structure showing distinct hydrophilic and hydrophobic regions (Fig. 2). The hydrophobic region consists of the adamantane skeleton while the hydrophilic layer consists of the polar amine and hydroxyl units.

Experimental
To a stirred solution of 2-(tricyclo[3.3.1.13,7]dec-2-ylamino)-ethanol (1 g, 5.1 mmol) in dichloromethane (30 ml) was added dropwise over 45 minutes a solution of benzoyl chloride (590ul, 5.1 mmol) dissolved in 50 ml of dichloromethane under a nitrogen atmosphere at zero degrees using an external ice salt bath. The reaction was allowed to stir overnight (Jacobson et al., 1987) and then filtered to remove the HCl salt and the solvent was removed in vacuo. The mixture was re-crystallized from methanol to obtain the title compound (I) (0.91 g, 60%) as a colourless microcrystalline solid.

Refinement
Hydrogen atoms were first located in the difference map then positioned geometrically, and allowed to ride on their respective parent atoms, with bond lengths of 0.99 Å (CH 2 ), 1.00 Å (Methine CH), 0.95 Å (Ar-CH) or 0.84 Å (OH). Isotropic displacement parameters for these atoms were set equal to 1.2 (CH 2 and CH), or 1.5 (OH) times U eq of the parent atom.   as those based on F, and R-factors based on ALL data will be even larger.