1-(2-Phenyl­eth­yl)adamantane

Rouchal, M.; Nečas, M.; Vícha, R.

doi:10.1107/S1600536810023251

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 (C-C) = 0.004 Å
R = 0.042
wR = 0.127
Data-to-parameter ratio = 8.9
Details

1-(2-Phenylethyl)adamantane

Michal Rouchal,^a Marek Necas ^b and Robert Vícha ^a ^*

^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). For some important properties of compounds bearing the adamantane scaffold, see: van der Schyf et al. (2009); van Bommel et al. (2001). For a related structure, see: Raine et al. (2002).

Experimental

Crystal data

C₁₈H₂₄
M_r = 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 radiation
= 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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.924, T_max = 1.000
11994 measured reflections
1452 independent reflections
1277 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.127
S = 1.30
1452 reflections
163 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13-C18 ring.

D-HA	D-H	HA	DA	D-HA
C18-H18Cg1ⁱ	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); 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 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.
Bommel, K. J. C. van, Metselaar, M. A., Werboom, W. & Reinhoudt, D. N. (2001). J. Org. Chem. 66, 5405-5412.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
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.
Schyf, C. J. van der & Geldenhuys, W. J. (2009). Neurotherapeutics, 6, 175-186.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds