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Volume 68 
Part 1 
Page o152  
January 2012  

Received 13 November 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.041
wR = 0.124
Data-to-parameter ratio = 7.4
Details
Open access

1-(4-Fluorophenyl)-2-(1H-imidazol-1-yl)ethanol

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
Correspondence e-mail: taoxiao@njut.edu.cn

In the title compound, C11H11FN2O, the dihedral angle between the mean planes of the two rings is 1.30 (4)°. In the crystal, O-H...N hydrogen bonds link the molecules into chains along the b axis.

Related literature

For related compounds containing a 2-(1H-imidazol-1-yl)-1-phenylethanol fragment, see: Porretta et al. (1993[Porretta, G. C., Fioravanti, R., Biava, M., Cirilli, R., Simonetti, N., Villa, A., Bello, U., Faccendini, P. & Tita, B. (1993). Eur. J. Med. Chem. 28, 749-760.]). For related structures, see: Tao et al. (2007[Tao, X., Yuan, L., Zhang, X.-Q., Jing, C. & Wang, J.-T. (2007). Acta Cryst. E63, o1330-o1331.]); Liu et al. (2011[Liu, D., Li, C., Yu, G. & Xiao, T. (2011). Acta Cryst. E67, o2036.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C11H11FN2O

  • Mr = 206.22

  • Monoclinic, P 21

  • a = 7.1220 (14) Å

  • b = 5.4690 (11) Å

  • c = 12.981 (3) Å

  • [beta] = 98.13 (3)°

  • V = 500.53 (19) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: multi-scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.970, Tmax = 0.990

  • 1992 measured reflections

  • 1024 independent reflections

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

  • Rint = 0.029

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.124

  • S = 1.00

  • 1024 reflections

  • 139 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O-H0A...N2i 0.87 (4) 1.90 (4) 2.762 (4) 171 (5)
Symmetry code: (i) [-x, y-{\script{1\over 2}}, -z].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZQ2137 ).


Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Liu, D., Li, C., Yu, G. & Xiao, T. (2011). Acta Cryst. E67, o2036.  [CSD] [CrossRef] [details]
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Porretta, G. C., Fioravanti, R., Biava, M., Cirilli, R., Simonetti, N., Villa, A., Bello, U., Faccendini, P. & Tita, B. (1993). Eur. J. Med. Chem. 28, 749-760.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tao, X., Yuan, L., Zhang, X.-Q., Jing, C. & Wang, J.-T. (2007). Acta Cryst. E63, o1330-o1331.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o152  [ doi:10.1107/S1600536811053505 ]

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