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

Liu, D.; Li, C.; Tian, X.; Li, S.; Xiao, T.

doi:10.1107/S1600536811053505

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 (C-C) = 0.005 Å
R = 0.041
wR = 0.124
Data-to-parameter ratio = 7.4
Details

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

Dong-liang Liu,^a Chen Li,^a Xin Tian,^a Song Li ^a and Tao Xiao ^a ^*

^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-HN 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). For related structures, see: Tao et al. (2007); Liu et al. (2011). For standard bond lengths, see: Allen et al. (1987).

Experimental

Crystal data

C₁₁H₁₁FN₂O
M_r = 206.22
Monoclinic, P 2₁
a = 7.1220 (14) Å
b = 5.4690 (11) Å
c = 12.981 (3) Å
= 98.13 (3)°
V = 500.53 (19) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.970, T_max = 0.990
1992 measured reflections
1024 independent reflections
876 reflections with I > 2(I)
R_int = 0.029
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2(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
_max = 0.13 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O-H0AN2ⁱ	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); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tao, X., Yuan, L., Zhang, X.-Q., Jing, C. & Wang, J.-T. (2007). Acta Cryst. E63, o1330-o1331.

organic compounds