(E)-1-(3,5-Difluoro­phen­yl)-3-(2,4-dimeth­oxy­phen­yl)prop-2-en-1-one

Tanxiao Huang; Dongdong Zhang; Quanzhi Yang; Xiaoyan Wei; Jianzhang Wu

doi:10.1107/S1600536810035257

. 2010 Sep 8;66(Pt 10):o2518. doi: 10.1107/S1600536810035257

(E)-1-(3,5-Difluorophenyl)-3-(2,4-dimethoxyphenyl)prop-2-en-1-one

Tanxiao Huang ^a, Dongdong Zhang ^b, Quanzhi Yang ^a, Xiaoyan Wei ^a, Jianzhang Wu ^a,^c,^*

PMCID: PMC2983274 PMID: 21587512

Abstract

The title compound, C₁₇H₁₄F₂O₃, is approximately planar, the dihedral angle between the rings being 5.46 (2)°. The H atoms of the central propenone group are trans. The crystal structure is stabilized by intermolecular C—H⋯F hydrogen bonds.

Related literature

For related structures, see: Peng et al. (2010 ▶); Wu, Zhang et al. (2009 ▶); Liang et al. (2007 ▶); Yathirajan et al. (2006 ▶). For background to and applications of chalcones, see: Nowakowska (2007 ▶); Nielsen et al. (2005 ▶); Wu, Qiu et al. (2009 ▶); Liang et al. (2009 ▶); Mojzisa et al. (2008 ▶); Liu et al. (2008 ▶); Wu et al. (2010 ▶); Zhao et al. (2010 ▶); Selvakumar et al. (2007 ▶).

Experimental

Crystal data

C₁₇H₁₄F₂O₃
M _r = 304.28
Triclinic,
a = 7.8047 (8) Å
b = 11.2591 (12) Å
c = 17.0080 (18) Å
α = 81.407 (2)°
β = 81.231 (2)°
γ = 76.319 (2)°
V = 1425.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.27 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.602, T _max = 1.000
7600 measured reflections
5242 independent reflections
2815 reflections with I > 2σ(I)
R _int = 0.034

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.162
S = 0.92
5242 reflections
401 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); 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 I, global. DOI: 10.1107/S1600536810035257/pb2039sup1.cif

e-66-o2518-sup1.cif^{(26.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810035257/pb2039Isup2.hkl

e-66-o2518-Isup2.hkl^{(256.7KB, 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
C25—H25⋯F4ⁱ	0.93	2.59	3.375 (3)	142
C13—H13⋯F4ⁱⁱ	0.93	2.46	3.303 (4)	151
C9—H9⋯F3ⁱⁱⁱ	0.93	2.66	3.532 (3)	156
C30—H30⋯F2ⁱⁱ	0.93	2.47	3.303 (4)	149
C8—H8⋯F2ⁱ	0.93	2.46	3.369 (3)	166
C28—H28⋯F1ⁱⁱⁱ	0.93	2.53	3.437 (3)	166

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

Chalcones, which have the common Skeleton of 1,3-diaryl-2-propen-1-ones, are open-chain flavonoids. Chalcones belong to nature products and distribute widespread in fruits, vegetables, tea and so on. Like as other flavonoids, Chalcones have wide-range biological properties, including antimicrobial, antitumor, antiangiogenic, antifungal, antioxidant activities and so on (Nowakowska, 2007; Zhao et al., 2010; Liu et al., 2008; Wu et al., 2010.). Moreover, Chalcones have low toxicity. Owing to its good effect and low toxicity, it has attract more and more scientists attention. Recent studies have demonstrated that synthesized Chalcones have the same activities as or better activities than natural chalcones (Nowakowska, 2007; Selvakumar et al., 2007).

Because Chalcones have good activity, the title chalcone derivative has been synthesized. In order to get detailed information such as the geometrical features and the underlying interaction of the crystal structure, an X-ray study of the title compound was carried out.

Two rings of molecule is approximately planar and the dihedral angle between the two rings is 5.46°. The H atoms of the central propenone group are trans. The average value of exocyclic bond angles [120.7 (4)°] and the bond distances [1.381 (5) Å] in the phenyl rings are agree quite well with the normal values reported in the literature for some analogous structures (Peng et al., 2010; Wu et al., 2009; Liang et al., 2007; Yathirajan et al., 2006). In the crystal, The crystal structure is stabilized by intermolecular C—H···F hydrogen bonds.

Experimental

The title compounds was synthesized by Claisene-Schmidt condensation. 2,4-dimethoxyBenzaldehyde (2 mmol) and 3',5'-Difluoroacetophenone (2 mmol) were dissolved in ehanol (20 ml). Temperature of reaction was controlled at 278 K and 5 drops NaOH (20%) was added. The reaction was monitored by thin-layer chromatography. 20 ml H₂O was added after 8 h and the yellow solid was Precipitated, washed with water and cold ethanol, dried and purified by column chromatography on silica gel. Single crystals of the title compound were grow in a CH₂Cl₂/CH₃CH₂OH mixture (2:1) at 277 K.