N-(2-Hydroxybenzyl)adamantan-1-aminium bromide

There are two independent ion pairs in the asymmetric unit of the title compound, C17H24NO+·Br−. In the crystal, the ions are linked by intermolecular N—H⋯Br and O—H⋯Br hydrogen bonds.


Experimental
Crystal data

Comment
The study of ferroelectric materials has received much attention and some materials have predominantly dielectric-ferroelectric performance (Fu et al., 2009;Ye et al., 2006;Zhang et al., 2008Zhang et al., , 2010, As a part of our work to obtain potential ferroelectric phase-change materials, we report herein on the crystal structure of title compound. Unluckily, the title compound has no dielectric anomalies in the temperature range 93-53 K, suggesting that it might be only a paraelectric. The asymmetric unit of the title compoundis is shown in Fig. 1 NaBH 4 (3.78 g, 10 mmol) was added into a solution of amantadine shrink Yang Schiff (6.38 g, 25 mmol) in anhydrous methanol (120 ml). After 5 h reaction, then the white solid, N-(2-hydroxybenzyl)-1-adamantylamine was obtained by reduced pressure distillation, extraction and drying. A solution of hydrobromide (0.8 g, 10 mmol) was added to a solution of N-(2-hydroxybenzyl)-1-adamantylamine (2.56 g, 10 mmol) in ethanol (20 ml). Single crystals suitable for X-ray diffraction were prepared by slow evaporation of the mixture at room temperature.

Refinement
The H atoms of OH group were located in a difference density Fourier map and these H atoms were refined freely with an isotropic displacement parameters U iso = 1.5U eq (O). All other H atoms were positioned geometrically and refined using a riding model, with N-H = 0.95Å, C-H = 0.93Å for aryl, 0.98Å for methine and 0.97Å for methylene H atoms, respectively.
U iso (H) = 1.2U eq (N), and 1.2U eq (C) for aryl, methine and methylene H atoms. Fig. 1. The molecular structure of the title compound, with the atomic numbering scheme. Thermal ellipsoids are shown at the 30% probability level.

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 > σ(F 2 ) is used only for calculating Rfactors(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.