1-(4-Fluoro­phen­yl)-3-hydr­oxy-3-phenyl­prop-2-en-1-one

Zheng, C.-Y.; Wang, D.-J.; Fan, L.

doi:10.1107/S1600536809004747

Volume 65
Part 3
Page o519
March 2009

Received 10 December 2008
Accepted 10 February 2009
Online 13 February 2009

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.051
wR = 0.140
Data-to-parameter ratio = 12.7
Details

1-(4-Fluorophenyl)-3-hydroxy-3-phenylprop-2-en-1-one

Chun-Yang Zheng,^a ^* Dun-Jia Wang ^b and Ling Fan ^b

^aHubei Key Laboratory of Pollutant Analysis & Reuse Technology, Hubei Normal University, Huangshi 435002,People's Republic of China, and ^bCollege of Chemistry and Environmental Engineering, Hubei Normal University, Huangshi 435002, People's Republic of China
Correspondence e-mail: zcy800204@163.com

In the crystal structure the title compound, C₁₅H₁₁FO₂, the molecule exists in the enol form. It is stabilized by an intramolecular O-HO hydrogen bond, in which the donor O-H and acceptor HO distances are almost equal. The dihedral angle between the two benzene rings is 22.30 (4)°.

Related literature

For background to the uses and characteristics of 1,3-diketones, see: Gilli et al. (2004); Hasegawa et al. (1997); Jang et al. (2006); Ma et al. (1999); Yoshida et al. (2005). For geometric data, see: Bertolasi et al. (1991); Wang et al. (2006).

Experimental

Crystal data

C₁₅H₁₁FO₂
M_r = 242.24
Monoclinic, P 2₁ /c
a = 11.8526 (5) Å
b = 11.7192 (5) Å
c = 9.4164 (4) Å
= 113.405 (1)°
V = 1200.35 (9) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 298 K
0.30 × 0.10 × 0.04 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.991, T_max = 0.996
11206 measured reflections
2109 independent reflections
1295 reflections with I > 2(I)
R_int = 0.106

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.140
S = 0.93
2109 reflections
166 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.25 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2AO1	1.23 (3)	1.30 (3)	2.4827 (19)	157 (2)

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KJ2112 ).

Acknowledgements

The authors are grateful to Hubei Normal University for financial support.

References

Bertolasi, V., Gilli, P., Ferretti, V. & Gilli, G. (1991). J. Am. Chem. Soc. 113, 4917-4925.
Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Gilli, P., Bertolasi, V., Pretto, L., Ferretti, V. & Gilli, G. (2004). J. Am. Chem. Soc. 126, 3845-3855.
Hasegawa, E., Ishiyama, K., Fujita, T., Kato, T. & Abe, T. (1997). J. Org. Chem. 62, 2396-2400.
Jang, H., Shin, C. H., Jung, B. J., Kim, D. H., Shim, H. K. & Do, Y. (2006). Eur. J. Inorg. Chem. 4, 718-725.
Ma, Y. L., Reardon, D., Gambarotta, S. & Yap, G. (1999). Organometallics, 18, 2773-2781.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, D.-J., Zheng, C.-Y. & Fan, L. (2006). Acta Cryst. E62, o3681-o3682.
Yoshida, J., Sato, H., Yamagishi, A. & Hoshino, N. (2005). J. Am. Chem. Soc. 127, 8453-8456.

organic compounds