2-(1-Adamant­yl)-1-(3-amino­phen­yl)ethanol

Michal Rouchal; Zuzana Kozubková; Marek Nečas; Robert Vícha

doi:10.1107/S1600536811034763

. 2011 Aug 27;67(Pt 9):o2515. doi: 10.1107/S1600536811034763

2-(1-Adamantyl)-1-(3-aminophenyl)ethanol

Michal Rouchal ^a, Zuzana Kozubková ^a, Marek Nečas ^b, Robert Vícha ^a,^*

PMCID: PMC3200880 PMID: 22059055

Abstract

In the crystal structure of the title compound, C₁₈H₂₅NO, molecules are linked via O—H⋯N hydrogen bonds, forming chains parallel to the c axis. Additional weak N—H⋯O interactions stabilize the crystal packing. The adamantane cage consists of three fused cyclohexane rings in almost ideal chair conformations, with C—C—C angles in the range 107.9 (10)–111.3 (11)°.

Related literature

For the biological activity of adamantane-bearing compounds, see: van der Schyf & Geldenhuys (2009) ▶. For related structures, see: Rouchal et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C₁₈H₂₅NO
M _r = 271.39
Orthorhombic,
a = 16.4467 (7) Å
b = 22.1873 (9) Å
c = 8.1033 (4) Å
V = 2957.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 120 K
0.30 × 0.20 × 0.10 mm

Data collection

Kuma KM-4 CCD diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T _min = 0.984, T _max = 1.000
30937 measured reflections
2602 independent reflections
1716 reflections with I > 2σ(I)
R _int = 0.053

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.068
S = 0.85
2602 reflections
190 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811034763/pk2344sup1.cif

e-67-o2515-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811034763/pk2344Isup2.hkl

e-67-o2515-Isup2.hkl^{(127.9KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811034763/pk2344Isup3.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
O1—H1A⋯N1ⁱ	0.84	2.10	2.9400 (14)	176
N1—H1C⋯O1ⁱⁱ	0.930 (15)	2.295 (15)	3.2048 (16)	166.0 (13)
N1—H1B⋯O1ⁱⁱⁱ	0.930 (16)	2.357 (16)	3.2472 (16)	160.1 (14)

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

Acknowledgments

Financial support of this work by the Tomas Bata Foundation, the Czech Ministry of Education (project No. MSM 7088352101) and the Internal Funding Agency of Tomas Bata University in Zlin (project No. IGA/6/FT/11/D) is gratefully acknowledged.

supplementary crystallographic information

Comment

It is matter of common knowledge that the well advised introduction of the highly lipophilic adamantane moiety into biologically active compounds might improve some pharmacological properties of the resulting molecule (van der Schyf & Geldenhuys, 2009). The title compound belongs to the series of recently synthesized building blocks for drug modification based on adamantylated aromatic amines.

The asymmetric unit of the title compound consists of a single molecule (Fig. 1). The benzene ring is nearly planar with a maximum deviation from the best plane being 0.006 (13) Å for C13. The torsion angles describing an arrangement of adamantane cage, benzene ring and aliphatic linker C1–C11–C12–C13, C11–C12–C13–C18, and C10–C1–C11–C12 are 158.37 (11), -95.75 (14), and -178.42 (11)°, respectively. The presented structure is linked into pairs by O–H···N hydrogen bonds (Fig. 2, Table 1). The crystal packing is further stabilized via intermolecular N–H···O interactions (Table 1).

Experimental

2-(1-Adamantyl)-1-(3-nitrophenyl)ethanol (350 mg, 1.16 mmol) was dissolved in methanol (34 cm³) and 7 cm³ of hydrochloric acid/water (1/1, v/v) was added. Into the refluxed and well stirred mixture, portions of an iron powder were added successively. The reaction was stopped when TLC indicated the consumption of all starting material. The mixture was neutralized with 5% solution of NaOH (50 cm³) and extracted with diethyl ether (6 × 10 cm³). Combined organic layers were twice washed with brine, dried over sodium sulfate and evaporated in vacuum. The purification of crude material by washing with hexane provided the desired product as a colourless crystalline powder (258 mg, 82%, mp 415–418 K). The crystal used for data collection was grown by spontaneous evaporation from diethyl ether at room temperature.