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

Tao Rong

doi:10.1107/S1600536811026742

. 2011 Jul 9;67(Pt 8):o1979. doi: 10.1107/S1600536811026742

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

Tao Rong ^a,^*

PMCID: PMC3213437 PMID: 22091016

Abstract

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.

Related literature

The title compound was studied as part of our work to obtain potential ferroelectric phase-change materials. For general background to ferroelectric organic frameworks, see: Fu et al. (2009 ▶); Ye et al. (2006 ▶); Zhang et al. (2008 ▶, 2010 ▶). For a related structure of the adamantyl ring, see: Cheng et al. (2008 ▶).

Experimental

Crystal data

C₁₇H₂₄NO⁺·Br⁻
M _r = 338.28
Triclinic,
a = 10.616 (2) Å
b = 12.627 (3) Å
c = 12.896 (3) Å
α = 108.46 (3)°
β = 104.69 (3)°
γ = 93.88 (3)°
V = 1565.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 2.62 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.596, T _max = 0.598
16356 measured reflections
7165 independent reflections
5368 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.108
S = 1.05
7165 reflections
369 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026742/lx2188sup1.cif

e-67-o1979-sup1.cif^{(28.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026742/lx2188Isup2.hkl

e-67-o1979-Isup2.hkl^{(350.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026742/lx2188Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯Br1ⁱ	0.82 (4)	2.45 (4)	3.255 (2)	168 (4)
N1—H1A⋯Br2ⁱⁱ	0.90	2.69	3.527 (3)	155
N1—H1B⋯Br2ⁱⁱⁱ	0.90	2.45	3.337 (2)	167
N2—H2A⋯Br1^iv	0.90	2.40	3.297 (2)	176
N2—H2B⋯Br2^iv	0.90	2.50	3.377 (2)	165

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

The authors are grateful to the starter fund of Southeast University for financial support to buy the X-ray diffractometer.

supplementary crystallographic information

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., 2008, 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. There are two independent molecules [labelled A & B]. The crystal packing (Fig. 2) is stabilized by weak intermolecular N—H···Br and O—H···Br hydrogen bonds between the N-(2-hydroxybenzyl)-1-adamantylammonium cations (Cheng et al. 2008) and bromide anions (see; Table 1).

Experimental

Salicylaldehyde (2.44 g, 20 mmol) and KOH (1.12 g, 20 mmol) were added into a solution of amantadine hydrochloride (3.76 g, 20 mmol) in ethanol. Then a little of anhydrous magnesium sulfate was added into it, after 6 h return the yellow precipitate came out. The yellow solid of amantadine shrink Yang Schiff was obtained by filtration, collection and drying. NaBH₄ (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.