[Journal logo]

Volume 66 
Part 7 
Page o1736  
July 2010  

Received 24 May 2010
Accepted 16 June 2010
Online 23 June 2010

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.004 Å
R = 0.042
wR = 0.127
Data-to-parameter ratio = 8.9
Details
Open access

1-(2-Phenylethyl)adamantane

aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and bDepartment of Chemistry, Faculty of Science, Masaryk University in Brno, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
Correspondence e-mail: rvicha@ft.utb.cz

In the title compound, C18H24, the adamantane cage consists of three fused cyclohexane rings in almost ideal chair conformations, with C-C-C angles in the range 108.0 (14)-111.1 (15)°. The phenyl and 1-adamantyl substituents adopt anti orientations with a C-C-C-C torsion angle of 177.10 (16)°. In the crystal packing, the molecules are linked by weak C-H...[pi] interactions into chains along the a axis.

Related literature

The title compound was prepared according to a modified procedure of Adkins & Billica (1948[Adkins, H. & Billica, H. R. (1948). J. Am. Chem. Soc. 70, 695-698.]). For some important properties of compounds bearing the adamantane scaffold, see: van der Schyf et al. (2009[Schyf, C. J. van der & Geldenhuys, W. J. (2009). Neurotherapeutics, 6, 175-186.]); van Bommel et al. (2001[Bommel, K. J. C. van, Metselaar, M. A., Werboom, W. & Reinhoudt, D. N. (2001). J. Org. Chem. 66, 5405-5412.]). For a related structure, see: Raine et al. (2002[Raine, A. L., Williams, C. M. & Bernhardt, P. V. (2002). Acta Cryst. E58, o1439-o1440.]).

[Scheme 1]

Experimental

Crystal data
  • C18H24

  • Mr = 240.37

  • Orthorhombic, P 21 21 21

  • a = 6.4844 (5) Å

  • b = 7.5109 (5) Å

  • c = 28.5305 (19) Å

  • V = 1389.55 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.06 mm-1

  • T = 120 K

  • 0.40 × 0.20 × 0.20 mm

Data collection
  • Kuma KM-4-CCD diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.924, Tmax = 1.000

  • 11994 measured reflections

  • 1452 independent reflections

  • 1277 reflections with I > 2[sigma](I)

  • Rint = 0.043

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.127

  • S = 1.30

  • 1452 reflections

  • 163 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13-C18 ring.

D-H...A D-H H...A D...A D-H...A
C18-H18...Cg1i 0.95 2.64 3.529 (3) 156
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z].

Data collection: CrysAlis CCD (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis RED (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2215 ).


Acknowledgements

Financial support of this work by the Czech Ministry of Education, project No. MSM 7088352101, and by the Tomas Bata Foundation is gratefully acknowledged.

References

Adkins, H. & Billica, H. R. (1948). J. Am. Chem. Soc. 70, 695-698.  [CrossRef] [ChemPort] [ISI]
Bommel, K. J. C. van, Metselaar, M. A., Werboom, W. & Reinhoudt, D. N. (2001). J. Org. Chem. 66, 5405-5412.  [PubMed]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.
Raine, A. L., Williams, C. M. & Bernhardt, P. V. (2002). Acta Cryst. E58, o1439-o1440.  [CSD] [CrossRef] [details]
Schyf, C. J. van der & Geldenhuys, W. J. (2009). Neurotherapeutics, 6, 175-186.  [CrossRef] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2010). E66, o1736  [ doi:10.1107/S1600536810023251 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.