(E)-3-(4-Fluoro­phen­yl)-1-phenyl-2-propen-1-one

Jing, L.-H.

doi:10.1107/S1600536809037635

Volume 65
Part 10
Page o2515
October 2009

Received 16 September 2009
Accepted 17 September 2009
Online 26 September 2009

Key indicators
Single-crystal X-ray study
T = 93 K
Mean (C-C) = 0.003 Å
R = 0.032
wR = 0.066
Data-to-parameter ratio = 8.2
Details

(E)-3-(4-Fluorophenyl)-1-phenyl-2-propen-1-one

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
Correspondence e-mail: jlhjhr@yahoo.com.cn

In the title compound, C₁₅H₁₁FO, the configuration of the keto group with respect to the olefinic double bond is s-cis. The dihedral angle between the planes of the two benzene rings is 10.61 (10)°. The crystal packing is stabilized by C-H [pi] interactions involving both benzene rings.

Related literature

For the synthesis, see: Chimenti et al. (2008). For the biological activity of chalcone derivatives, see: Dimmock et al. (1999).

Experimental

Crystal data

C₁₅H₁₁FO
M_r = 226.24
Monoclinic, C c
a = 24.926 (9) Å
b = 5.6940 (19) Å
c = 7.749 (3) Å
= 94.747 (5)°
V = 1096.0 (6) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 93 K
0.40 × 0.33 × 0.30 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
4214 measured reflections
1256 independent reflections
1174 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.066
S = 1.05
1256 reflections
154 parameters
2 restraints
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C1-H1Cg1ⁱ	0.95	2.89	3.592 (3)	132
C4-H4Cg1ⁱⁱ	0.95	2.93	3.646 (6)	133
C12-H12Cg2ⁱⁱⁱ	0.95	2.85	3.505 (8)	127
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{5\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{3\over 2}}, z-1]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-1]$ . Cg1 and Cg2 are the centroids of the C1-C6 and C10-C15 rings, respectively.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2914 ).

Acknowledgements

The author thanks the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Chimenti, F., Fioravanti, R., Bolasco, A., Manna, F., Chimenti, P., Secci, D., Rossi, F., Turini, P., Ortuso, F., Alcaro, S. & Cardia, M. C. (2008). Eur. J. Med. Chem. 43, 2262-2267.
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1149.
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds