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Volume 69 
Part 1 
Page o108  
January 2013  

Received 23 November 2012
Accepted 12 December 2012
Online 19 December 2012

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.094
Data-to-parameter ratio = 14.2
Details
Open access

2-(Adamantan-1-yl)-1,3-bis(4-methylphenyl)propan-2-ol

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, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic
Correspondence e-mail: rvicha@ft.utb.cz

The conformation of the title compound, C27H34O, is stabilized by a weak intramolecular C-H...[pi] interaction. The dihedral angle between the benzene rings is 54.79 (4)°. The adamantane cage consists of three fused cyclohexane rings in classical chair conformations, with C-C-C angles in the range 107.75 (10)-111.35 (9)°. Although the molecule contains a hydroxy group as a conceivable hydrogen-bond donor, this group is sterically hindered by bulky substituents and no hydrogen bonds are observed in the crystal structure.

Related literature

For the preparation of the title compound, see: Vícha et al. (2006[Vícha, R., Necas, M. & Potácek, M. (2006). Collect. Czech. Chem. Commun. 71, 709-722.]). For other examples of sterically shielded carbinols, see: Babjaková et al. (2010[Babjaková, E., Necas, M. & Vícha, R. (2010). Acta Cryst. E66, o2175.]); Vícha & Necas (2010[Vícha, R. & Necas, M. (2010). Acta Cryst. E66, o1626.]). For the structure of a related molecule which does form a hydrogen-bonded dimer in the solid state, see: Vaissermann & Lomas (1997[Vaissermann, J. & Lomas, J. S. (1997). Acta Cryst. C53, 1341-1343.]).

[Scheme 1]

Experimental

Crystal data
  • C27H34O

  • Mr = 374.54

  • Triclinic, [P \overline 1]

  • a = 6.4065 (2) Å

  • b = 13.1474 (4) Å

  • c = 13.3466 (4) Å

  • [alpha] = 70.718 (3)°

  • [beta] = 81.700 (3)°

  • [gamma] = 80.134 (3)°

  • V = 1040.75 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 120 K

  • 0.50 × 0.50 × 0.40 mm

Data collection
  • Agilent Xcalibur (Sapphire2) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]) Tmin = 0.996, Tmax = 1.000

  • 6750 measured reflections

  • 3675 independent reflections

  • 2925 reflections with I > 2[sigma](I)

  • Rint = 0.010

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.094

  • S = 1.07

  • 3675 reflections

  • 258 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31-C36 ring.

D-H...A D-H H...A D...A D-H...A
C12-H12...Cg1 0.94 2.61 3.3577 (12) 136

Data collection: CrysAlis PRO (Agilent, 2011[Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: NK2194 ).


Acknowledgements

The financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin (project No. IGA/FT/2012/016) is gratefully acknowledged.

References

Agilent (2011). CrysAlis PRO. Agilent Technologies UK Ltd, Yarnton, England.
Babjaková, E., Necas, M. & Vícha, R. (2010). Acta Cryst. E66, o2175.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [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]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Vaissermann, J. & Lomas, J. S. (1997). Acta Cryst. C53, 1341-1343.  [CSD] [CrossRef] [details]
Vícha, R. & Necas, M. (2010). Acta Cryst. E66, o1626.  [CSD] [CrossRef] [details]
Vícha, R., Necas, M. & Potácek, M. (2006). Collect. Czech. Chem. Commun. 71, 709-722.


Acta Cryst (2013). E69, o108  [ doi:10.1107/S1600536812050647 ]

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