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

Babjaková, E.; Bartoš, P.; Vícha, R.

doi:10.1107/S1600536812050647

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 (C-C) = 0.002 Å
R = 0.035
wR = 0.094
Data-to-parameter ratio = 14.2
Details

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

Eva Babjaková,^a Peter Bartos ^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, 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). For other examples of sterically shielded carbinols, see: Babjaková et al. (2010); Vícha & Necas (2010). For the structure of a related molecule which does form a hydrogen-bonded dimer in the solid state, see: Vaissermann & Lomas (1997).

Experimental

Crystal data

C₂₇H₃₄O
M_r = 374.54
Triclinic, $[P \overline 1]$
a = 6.4065 (2) Å
b = 13.1474 (4) Å
c = 13.3466 (4) Å
= 70.718 (3)°
= 81.700 (3)°
= 80.134 (3)°
V = 1040.75 (6) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.996, T_max = 1.000
6750 measured reflections
3675 independent reflections
2925 reflections with I > 2(I)
R_int = 0.010

Refinement

R[F² > 2(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
_max = 0.18 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C31-C36 ring.

D-HA	D-H	HA	DA	D-HA
C12-H12Cg1	0.94	2.61	3.3577 (12)	136

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) 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: 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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vaissermann, J. & Lomas, J. S. (1997). Acta Cryst. C53, 1341-1343.
Vícha, R. & Necas, M. (2010). Acta Cryst. E66, o1626.
Vícha, R., Necas, M. & Potácek, M. (2006). Collect. Czech. Chem. Commun. 71, 709-722.

organic compounds