Bis[N-(2-hydroxybenzyl)adamantan-1-aminium] fluoride tetrafluoroborate monohydrate

In the title compound, 2C17H24NO+·BF4 −·F−·H2O, the asymmetric unit contains two N-(2-hydroxybenzyl)adamantan-1-aminium cations, one BF4 − anion, one F− anion and one water molecule. Both amine N atoms are protonated. The hydroxy O atoms, amino N atoms and water O atom are involved in intermolecular O—H⋯O, O—H⋯F, N—H⋯O and N—H⋯F hydrogen bonding.


Comment
Organic amino compounds attracted more attention as phase transition dielectric materials for its application in memory storage (Fu et al. 2007;Fu & Xiong 2008;Fu et al. 2008;Fu et al. 2009). With the purpose of obtaining phase transition crystals of amino compounds, various amines have been studied and we have elaborated a series of new materials with this organic molecules (Fu et al. 2011a;Fu et al. 2011b;Fu et al. 2011c). In this study, we describe the crystal structure of the title compound, bis-N-(2-Hydroxybenzyl)adamantan-1-aminium tetrafluoroborate monofluoride monohydrate.
The asymmetric unit is composed of two N-(2-Hydroxybenzyl)adamantan-1-aminium cations, one BF 4 anion, one Fanion and one water molecule. The two benzene rings are nearly coplanar and only twisted from each other by a dihedral angle
Colorless block crystals suitable for X-ray analysis were obtained after one week.

Refinement
All H atoms attached to C atoms were fixed geometrically and treated as riding with C-H = 0.93 Å (aromatic), C-H = 0.97 Å (methylene) and C-H = 0.98 Å (methine) with U iso (H) = 1.2U eq (C). H atoms bonded to N and O atoms were located in difference Fourier maps and restrained with the H-N = 0.90 (2)Å and H-O = 0.82 (2)Å. In the last stage of refinement they were treated as riding on the N and O atoms with U iso (H) = 1.2U eq (N) and U iso (H) = 1.5U eq (O).

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.