1-(4-Amino­phen­yl)-3-[2-(trifluoro­meth­yl)phen­yl]prop-2-en-1-one

Jing Peng; Huifen Xu; Zhe Li; Yuyan Zhang; Jianzhang Wu

doi:10.1107/S1600536810014169

. 2010 Apr 24;66(Pt 5):o1156–o1157. doi: 10.1107/S1600536810014169

1-(4-Aminophenyl)-3-[2-(trifluoromethyl)phenyl]prop-2-en-1-one

Jing Peng ^a, Huifen Xu ^a, Zhe Li ^b, Yuyan Zhang ^a, Jianzhang Wu ^a,^c,^*

PMCID: PMC2979023 PMID: 21579201

Abstract

The title compound, C₁₆H₁₂F₃NO, a derivative of biologically active chalcones, comprises two benzene rings and a central –CH=CH—C(=O)– unit. The dihedral angle between the two rings is 10.9 (1)° and the molecule adopts an E configuration about the central olefinic bond. The crystal structure is stabilized by intermolecular N—H⋯O and N—H⋯N hydrogen bonds.

Related literature

For related structures, see: Narender et al. (2007 ▶); Kamal et al. (2008 ▶); Wu et al. (2009 ▶); Low et al. (2002 ▶); Yathirajan et al. (2006 ▶); Suwunwong et al. (2009 ▶). For background to and applications of chalcones, see: Heidari et al. (2009 ▶); Nielsen et al. (2005 ▶); Mojzis et al. (2008 ▶); Achanta et al. (2006 ▶); Dimmock et al. (1999 ▶); Liang et al. (2007a ▶,b ▶, 2009 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C₁₆H₁₂F₃NO
M _r = 291.27
Monoclinic,
a = 18.835 (3) Å
b = 4.7866 (8) Å
c = 15.177 (3) Å
β = 101.108 (3)°
V = 1342.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 273 K
0.43 × 0.28 × 0.22 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.951, T _max = 0.974
6607 measured reflections
2360 independent reflections
1700 reflections with I > 2σ(I)
R _int = 0.130

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.185
S = 1.00
2360 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2001 ▶); data reduction: SAINT-Plus; 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/S1600536810014169/zq2037sup1.cif

e-66-o1156-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014169/zq2037Isup2.hkl

e-66-o1156-Isup2.hkl^{(116KB, 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
N1—H1A⋯N1ⁱ	0.86	2.42	3.235 (3)	158
N1—H1B⋯O1ⁱⁱ	0.86	2.45	3.162 (3)	140

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

Acknowledgments

This work was supported by the Zhejiang Province Extremely Key Subject Building Funding (Pharmacology and Biochemical Pharmaceutics 2008), the Department of Education of Zhejiang Province (No. 20070907) and the Wenzhou Administration of Science and Technology project (No. Y20080016).

supplementary crystallographic information

Comment

Chalcones, which are open-chain flavonoids, distribute widespread in fruits, vegetables and so on. Chalcone and their derivatives are obtained from the aldol condensation of aromatic aldehydes and aromatic ketones. They are important intermediate of organic synthesis. Due to their significant biological activities such as anti-inflammatory, antibacterial, antiangiogenic, antitumor and analgesic, they have attracted more and more attention (Heidari et al., 2009; Nielsen et al., 2005; Mojzis et al., 2008; Achanta et al., 2006; Dimmock et al., 1999). The molecule of chalcone possess two phenyl rings and one –CH=CH–C(=O)– central part. The carbonyl functional group which is responsible for the antibacterial activity of these compounds is the main feature of chalcone derivatives (Suwunwong et al., 2009).

Due to the broad spectrum of biological activities of this type of compounds, various chalcone analogues have been synthesized in order to filter the better ones or the unique ones (Narender et al., 2007; Kamal et al., 2008). As a continuation of our broad program of work on the synthesis and structural study of chalcones, the title chalcone derivative has been obtained and an X-ray diffraction study was carried out.

The molecule is approximately planar and the dihedral angle between the two phenyl rings is 10.9 (1)°. The H atoms of the central propenone group are trans to each other. The average value of the phenyl bond distances [1.385 (5) Å] and bond angles [120.7 (4)°] have normal values which agree quite well with the values reported in the literature for some analogous structures (Wu et al., 2009; Low et al., 2002; Yathirajan et al., 2006). The crystal structure is stabilized by intermolecular N(1)–H1A···O(1) and N(1)–H1B···N(1) hydrogen bonds.

Experimental

1-(4-aminophenyl)ethanone (5 mmol) was dissolved in ethanol (10 ml) and a solution of KOH (40%, 5 drops) was added. The flask was immersed in bath of crushed ice and a solution of 2-(trifluoromethyl)benzaldehyde (5 mmol) in ethanol (10 ml) was added. The reaction mixture was stirred at 300 K and completion of the reaction was monitored by thin-layer chromatography. Ice-cold water was added to the reaction mixture after 24 h and the yellow solid that separated was filtered off, washed with water and cold ethanol, dried and purified by column chromatography on silica gel (yield: 68%). Single crystals of the title compound were grown in a CH₂Cl₂/CH₃OH mixture (7:3 v/v) by slow evaporation at 277 K.