N-(2-Hydroxybenzyl)adamantan-1-aminium 4-methylbenzenesulfonate

In the crystal structure of the title salt, C17H24NO+·C7H7O3S−, the N-(2-hydroxybenzyl)adamantan-1-aminium cations and 4-methylbenzenesulfonate anions are linked by O—H⋯O and N—H⋯O hydrogen bonds. C—H⋯π interactions are also observed between the cation and the anion.

Cg is the centroid of the C18-C23 benzene ring.  S.-G. Hou

Comment
Organic salts are becoming increasingly important as new molecule-based crystalline materials with the potential to provide optimal physical properties whilst retaining the chemical properties of the organic components (Blagden et al., 2008;Vishweshwar et al., 2006). Physicochemical properties such as the melting point, stability and solubility can be tuned through crystallization (Kapildev et al., 2011;Schultheiss & Newman, 2009). The synthesis of organic salts often relies on the acidamide H-bonds interactions. Herein, we report the crystal structure of the title compound, N-(2-hydroxybenzyl)adamantan-1-aminium 4-methylbenzenesulfonate.
The asymmetric unit is composed of one N-(2-Hydroxybenzyl)adamantan-1-aminium cation and one 4-methylbenzenesulfonate anion. The amine N1 atom was protonated. And the sulfonic group was deprotonated to keep the charge balance.
The two benzene rings are nearly perpendicular and twisted from each other by a dihedral of 83.11 (1)°. The geometric parameters of the title compound are in the normal range.
In the crystal structure, all the hydroxy and amino H atoms are involved in intermolecular O-H···O and N-H···O hydrogen bonds interactions with the sulfonic O atoms. These hydrogen bonds link the molecules into an one-dimentional chain parallel to the a-axis (Table 1 and Fig.2).

Experimental
A mixture of N-(2-hydroxybenzyl)adamantan-1-amine (2.0 mmol), 4-methylbenzenesulfonic acid (2.0 mL) and 20 mL distilled water were added into a 50 ml flask and refluxed for 5 h, then cooled and filtrated. The solution was evaporated slowly in the air. Colorless block crystals suitable for X-ray analysis were obtained after one week.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2sigma(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.