3-Fluoro-4-(4-hy­droxy­phen­oxy)benzonitrile

Zheng, M.; Wang, J.; Zhang, J.; Luo, S.

doi:10.1107/S1600536810024360

Volume 66
Part 7
Page o1856
July 2010

Received 12 May 2010
Accepted 23 June 2010
Online 30 June 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.037
wR = 0.117
Data-to-parameter ratio = 9.6
Details

3-Fluoro-4-(4-hydroxyphenoxy)benzonitrile

Mei Zheng,^a Jianfeng Wang,^b Jixu Zhang ^b and Shuping Luo ^b ^*

^aHangzhou Huadong Medicine Group Biotechnology Institute Co. Ltd, Hangzhou 310015, People's Republic of China, and ^bState Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: zhangjixu123@163.com

The title compound, C₁₃H₈FNO₂, was synthesized from 3,4-difluorobenzonitrile and hydroquinone. The dihedral angle between the two aromatic rings is 70.9 (2)°. In the crystal structure, molecules are linked by O-HN hydrogen bonds, forming zigzag chains.

Related literature

For the herbicidal actvity of hydroquinone derivatives, see: Bao et al. (2007); Liu (2002). For related structures, see: Sørensen et al. (2009); Luo et al. (2009); Zhang et al. (2009).

Experimental

Crystal data

C₁₃H₈FNO₂
M_r = 229.20
Orthorhombic, P 2₁ 2₁ 2₁
a = 6.1932 (4) Å
b = 8.8109 (5) Å
c = 20.5269 (12) Å
V = 1120.11 (12) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 295 K
0.39 × 0.31 × 0.22 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.959, T_max = 0.976
10999 measured reflections
1498 independent reflections
928 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.117
S = 1.01
1498 reflections
156 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H201N1ⁱ	0.82	2.03	2.839 (4)	168
Symmetry code: (i) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ .

Data collection: PROCESS-AUTO (Rigaku, 2006); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2202 ).

Acknowledgements

The authors are grateful to Mr Jianming Gu for the crystal structure analysis.

References

Bao, W. J., Wu, Y. G., Mao, C. H., Chen, M. & Huang, M. Z. (2007). Fine Chem. Intermed. 37, 9-13.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Liu (2002). Please supply full reference.
Luo, S., Zhang, J., Wang, J. & Li, B. (2009). Acta Cryst. E65, o2011.
Rigaku (2006). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan
Rigaku/MSC (2007). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sørensen, H. O. & Stuhr-Hansen, N. (2009). Acta Cryst. E65, o13.
Zhang, J., Wu, J., Wang, J., Li, Y. & Luo, S. (2009). Acta Cryst. E65, o2340.

organic compounds