3-(4-Fluoro­phen­yl)-1-(4-methoxy­phen­yl)prop-2-en-1-one

Pu-Su Zhao; Xian Wang; Huan-Mei Guo; Fang-Fang Jian

doi:10.1107/S1600536809018121

. 2009 May 29;65(Pt 6):o1402. doi: 10.1107/S1600536809018121

3-(4-Fluorophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one

Pu-Su Zhao ^a, Xian Wang ^a, Huan-Mei Guo ^b, Fang-Fang Jian ^b,^*

PMCID: PMC2969700 PMID: 21583247

Abstract

The title compound, C₁₆H₁₃FO₂, was prepared from 4-methoxyhypnone and 4-fluorobenzophenone by Claisen–Schmidt condensation. All the bond lengths and bond angles are in normal ranges. The dihedral angle formed by the two benzene rings is 33.49 (2)°. The crystal packing is stabilized by intermolecular C—H⋯O hydrogen-bonding interactions.

Related literature

For the biological activity of chalcones, see: Hsieh et al. (1998 ▶); Anto et al. (1994 ▶). For the effectiveness of chalcones against cancer, see: De Vincenzo et al. (2000 ▶); Dimmock et al. (1998 ▶). For a related structure, see: Guo et al. (2008 ▶).

Experimental

Crystal data

C₁₆H₁₃FO₂
M _r = 256.26
Orthorhombic,
a = 7.457 (4) Å
b = 11.072 (6) Å
c = 31.063 (18) Å
V = 2565 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 273 K
0.13 × 0.12 × 0.09 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: none
14904 measured reflections
3050 independent reflections
2203 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.116
S = 1.01
3050 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.12 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809018121/at2773sup1.cif

e-65-o1402-sup1.cif^{(16.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018121/at2773Isup2.hkl

e-65-o1402-Isup2.hkl^{(149.8KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2ⁱ	0.93	2.50	3.376 (2)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the National Natural Science Foundation of Shandong (Y2007B14; Y2008B29) and Weifang University for research grants.

supplementary crystallographic information

Comment

Among flavonoids, chalcones have been identified as interesting compounds having multiple biological actions which include antiinflammatory (Hsieh et al., 1998) and antioxidant (Anto et al., 1994). Of particular interest, the effectiveness of chalcones againist cancer has been investigated (De Vincenzo et al., 2000; Dimmock et al., 1998). As part of our search for new biologically active compounds we synthesized the title compound (I) and report its crystal structure here.

In the crystal structure of compound (I) (Fig. 1), the dihedral angle formed by the benzene rings (C1–C6) and (C7–C12) is 33.49 (2)°. All the bond lengths and bond angles are in normal ranges. (Guo et al., 2008). There are intra- and intermolecular C—H···O hydrogen-bond interactions to stabilize the crystal structure (Table 1, Fig. 2).

Experimental

A mixture of the 4-methoxyhypnone (0.02 mol), 4-fluorobenzophenone (0.02 mol) and 10% NaOH (10 ml) was stirred in ethanol (30 ml) for 3 h to afford the title compound (yield 83%). Single crystals suitable for X-ray measurements were obtailed by recrystallization from ethanol at room temperature.