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

Zhe Li; Yanan Wang; Kesong Peng; Lingzi Chen; Shenghui Chu

doi:10.1107/S1600536812006046

. 2012 Feb 17;68(Pt 3):o776. doi: 10.1107/S1600536812006046

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

Zhe Li ^a, Yanan Wang ^a, Kesong Peng ^b, Lingzi Chen ^b, Shenghui Chu ^b,^*

PMCID: PMC3297847 PMID: 22412650

Abstract

The crystal structure of the title compound, C₁₇H₁₅BrO₃, a chalcone derivative, exhibits two crystallographically independent molecules per asymmetric unit showing an E conformation about the ethylene double bond. In each molecule, the two phenyl rings are almost coplanar: the mean planes make dihedral angles of 9.3 (2) and 19.4 (2)°. In the crystal, molecules are linked through weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For related structures, see: Wu et al. (2009 ▶, 2010 ▶, 2011a ▶,b ▶); Huang et al. (2010 ▶); Peng et al. (2010 ▶). For background to and applications of chalcones, see: Nielsen et al. (2005 ▶); Wu et al. (2010 ▶, 2011a ▶,b ▶).

Experimental

Crystal data

C₁₇H₁₅BrO₃
M _r = 347.20
Triclinic,
a = 11.574 (6) Å
b = 11.781 (6) Å
c = 11.877 (6) Å
α = 91.857 (9)°
β = 107.021 (9)°
γ = 91.917 (9)°
V = 1546.2 (13) Å³
Z = 4
Mo Kα radiation
μ = 2.67 mm⁻¹
T = 298 K
0.49 × 0.34 × 0.24 mm

Data collection

Bruker APEX diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T _min = 0.355, T _max = 0.567
7968 measured reflections
5326 independent reflections
3031 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.135
S = 1.00
5326 reflections
383 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.75 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812006046/zq2148sup1.cif

e-68-0o776-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006046/zq2148Isup2.hkl

e-68-0o776-Isup2.hkl^{(260.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812006046/zq2148Isup3.cml

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
C29—H29⋯O2ⁱ	0.93	2.59	3.256 (5)	129
C33—H33A⋯O1ⁱⁱ	0.96	2.46	3.323 (5)	149

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

Acknowledgments

This study was partially supported by a University Students in Zhejiang Science and Technology Innovation Project (grant No. 2010R413019) and by the State Administration of Traditional Chinese Medicine of Zhejiang Province (project No. 2011ZB085).

supplementary crystallographic information

Comment

Natural chalcones exist widely in vegetables, fruits, medicinal plants, and so on. Natural and synthetical chalcones have extensive biological properties such as anti-inflammatory, antitumor, antioxidant (Nielsen et al., 2005; Wu et al., 2010, 2011a,b). We synthesized a series of chalcones in order to study antitumor activity. We obtain monocrystals of the title compound, and its crystal structure was characterized by a X-ray diffraction study.

The crystal structure of the title compound, C₁₇H₁₅BrO₃, a chalcone derivative, exhibits two crystallographically independent molecules per asymmetric unit showing an E configuration about the ethylene double bond (see for instance: Wu et al., 2009; Peng et al., 2010; Huang et al., 2010). In each molecule, the two phenyl rings are almost coplanar: the mean planes make dihedral angles of 9.3 (2) and 19.4 (2)°. In the crystal, molecules are linked through weak intermolecular C—H···O hydrogen bonds.

Experimental

The title compound was synthesized by Claisene–Schmidt condensation between 3,4-dimethoxybenzaldehyde and 2'-bromoacetophenone. 3,4-Dimethoxybenzaldehyde (1 mmol) and 2'-bromoacetophenone (1 mmol) were dissolved in ethanol (10 ml). NaOH (40%, 5 drops) was added at 283 K. The temperature during the whole reaction was controlled to remain below 288 K. The reaction was monitored by thin-layer chromatography. After reaction was over, 10 ml H₂O was added and the white solid was precipitated, washed with a mixture of water and cold ethanol (10:1), and dried (yield: 75.3%, m.p. 372–376 K). The title compound was dissolved in a mixture solution of ethanol and dichloromethane. Single crystals were obtained by solvent evaporation.