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Volume 68 
Part 3 
Page o580  
March 2012  

Received 23 January 2012
Accepted 27 January 2012
Online 4 February 2012

[zq2152sup1]
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Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.147
Data-to-parameter ratio = 11.7
Details
Open access

2-(Biphenyl-4-yl)propan-2-ol

Eric Modau,a David C. Lilesa and Petrus H. van Rooyena*

aDepartment of Chemistry, University of Pretoria, Private Bag X20, Hatfield 0028, South Africa
Correspondence e-mail: phvr@up.ac.za

The title compound, C15H16O, crystallizes with two independent molecules in the asymmetric unit. Due to the space-group symmetry, this results in the formation of a tetramer where the four molecules are connected by O-H...O hydrogen bonds. The molecules pack parallel to the c axis. Both molecules in the asymmetric unit are nonplanar and the dihedral angles between connected aromatic rings in each molecule are 7.96 (12) and 9.75 (13)°. This contrasts with the gas phase density functional theory (DFT) optimized conformation, where this dihedral angle is 39.33°.

Related literature

For some previous studies of biphenyl derivitives, see: Britton & Gleason (1991[Britton, D. & Gleason, W. B. (1991). Acta Cryst. C47, 2127-2131.]); Britton & Young (2003[Britton, D. & Young, V. G. Jr (2003). Acta Cryst. E59, o1849-o1851.]); Brock (1980[Brock, C. P. (1980). Acta Cryst. B36, 968-971.]); Brock & Haller (1980[Brock, C. P. & Haller, K. L. (1980). J. Phys. Chem. 88, 3570-3574.]); Mohamed et al. (2003[Mohamed, A. K., Auner, N. & Bolte, M. (2003). Acta Cryst. E59, o476-o477.]). For details of GAUSSIAN03, see: Frisch et al. (2003[Frisch, M. J., et al. (2003). GAUSSIAN03. Gaussian Inc., Pittsburgh, Pennsylvania, USA.]).

[Scheme 1]

Experimental

Crystal data

  • C15H16O

  • Mr = 212.28

  • Monoclinic, C 2/c

  • a = 12.4406 (14) Å

  • b = 15.5754 (18) Å

  • c = 25.741 (3) Å

  • [beta] = 102.332 (2)°

  • V = 4872.7 (10) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.07 mm-1

  • T = 295 K

  • 0.46 × 0.36 × 0.08 mm
Data collection

  • Bruker P4 diffractometer with SMART 1000 CCD area detector

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.931, Tmax = 0.994

  • 12927 measured reflections

  • 4590 independent reflections

  • 2859 reflections with I > 2[sigma](I)

  • Rint = 0.029
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.147

  • S = 1.01

  • 4590 reflections

  • 391 parameters

  • 3 restraints

  • All H-atom parameters refined

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O2 0.90 (1) 1.99 (2) 2.804 (2) 150 (4)
O2-H2A...O1 0.90 (1) 2.09 (4) 2.804 (2) 136 (4)
O1-H1B...O1i 0.87 (3) 1.90 (3) 2.767 (3) 174 (4)
O2-H2B...O2i 0.89 (1) 2.03 (1) 2.926 (3) 177 (4)
Symmetry code: (i) [-x, y, -z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]), 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.]) and POV-RAY (Cason, 2004[Cason, C. J. (2004). POV-RAY for Windows. Persistence of Vision, Raytracer Pty Ltd, Victoria, Australia. http://www.povray.org.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2152 ).

Acknowledgements

The authors thank the University of Pretoria for financial support.

References

Britton, D. & Gleason, W. B. (1991). Acta Cryst. C47, 2127-2131.  [CrossRef] [details]
Britton, D. & Young, V. G. Jr (2003). Acta Cryst. E59, o1849-o1851.  [CSD] [CrossRef] [details]
Brock, C. P. (1980). Acta Cryst. B36, 968-971.  [CrossRef] [details] [ISI]
Brock, C. P. & Haller, K. L. (1980). J. Phys. Chem. 88, 3570-3574.  [CrossRef] [ISI]
Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cason, C. J. (2004). POV-RAY for Windows. Persistence of Vision, Raytracer Pty Ltd, Victoria, Australia. http://www.povray.org.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Frisch, M. J., et al. (2003). GAUSSIAN03. Gaussian Inc., Pittsburgh, Pennsylvania, USA.
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]
Mohamed, A. K., Auner, N. & Bolte, M. (2003). Acta Cryst. E59, o476-o477.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]

Acta Cryst (2012). E68, o580  [ doi:10.1107/S1600536812003716 ]

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