(E)-1-(4-Amino­phen­yl)-3-(pyridin-3-yl)prop-2-en-1-one

Suchada Chantrapromma; Thawanrat Kobkeatthawin; Kullapa Chanawanno; Pitikan Wisitsak; Hoong-Kun Fun

doi:10.1107/S1600536811023634

. 2011 Jun 22;67(Pt 7):o1770–o1771. doi: 10.1107/S1600536811023634

(E)-1-(4-Aminophenyl)-3-(pyridin-3-yl)prop-2-en-1-one

Suchada Chantrapromma ^a,^*,^‡, Thawanrat Kobkeatthawin ^a, Kullapa Chanawanno ^a, Pitikan Wisitsak ^b, Hoong-Kun Fun ^c,^§

PMCID: PMC3152058 PMID: 21837148

Abstract

The title chalcone derivative, C₁₄H₁₂N₂O, consists of 4-aminophenyl and pyridine rings bridged by a prop-2-en-1-one unit and exists in a trans configuration with respect to the C=C double bond. The molecule is slightly twisted with a dihedral angle of 29.38 (7)° between the benzene and pyridine rings. The prop-2-en-1-one bridge is nearly planar with an r.m.s. deviation of 0.0384 (1) Å and makes dihedral angles of 15.40 (9) and 16.30 (9)°, respectively, with the benzene and pyridine rings. In the crystal, molecules are linked by N—H⋯N and N—H⋯O hydrogen bonds into a layer parallel to the ab plane. A π–π interaction with a centroid–centroid distance of 3.6946 (10) Å is also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Horkaew et al. (2010 ▶). For background to and applications of chalcones, see: Gaber et al. (2008 ▶); Ávila et al. (2008 ▶); Mei et al. (2001 ▶); Ohad et al. (2004 ▶); Patil et al. (2007 ▶); Svetlichny et al. (2007 ▶); Tewtrakul et al. (2003 ▶); Wu et al. (2006 ▶); Xu et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₁₄H₁₂N₂O
M _r = 224.26
Orthorhombic,
a = 12.0046 (12) Å
b = 7.9329 (9) Å
c = 22.925 (3) Å
V = 2183.2 (4) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.52 × 0.32 × 0.18 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.956, T _max = 0.985
12726 measured reflections
3177 independent reflections
2433 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.132
S = 1.03
3177 reflections
202 parameters
All H-atom parameters refined
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811023634/is2731sup1.cif

e-67-o1770-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811023634/is2731Isup2.hkl

e-67-o1770-Isup2.hkl^{(156KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811023634/is2731Isup3.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
N1—H1N1⋯O1ⁱ	0.88 (2)	2.13 (2)	2.9920 (16)	170 (2)
N1—H2N1⋯N2ⁱⁱ	0.93 (2)	2.26 (2)	3.1471 (17)	161.7 (19)

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

Acknowledgments

The authors thank the Thailand Research Fund (TRF) for a research grant (RSA 5280033) and the Prince of Songkla University for financial support. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

supplementary crystallographic information

Comment

Chalcones are 1,3-diaryl-2-propen-1-ones which can be obtained from both synthetic and natural sources. They have a wide variety of biological activities such as antimalarial (Mei et al., 2001), HIV-1 protease inhibitory (Tewtrakul et al., 2003), antityrosinase (Ohad et al., 2004), antibacterial (Ávila et al., 2008) and antiplasmodial (Wu et al., 2006) properties. Moreover, chalcones have also been studied for non-linear optical (NLO) (Patil et al., 2007) and fluorescent materials (Gaber et al., 2008). These compounds have also been used for sensor, liquid crystal display and fluorescence probe for sensing of DNA or proteins (Svetlichny et al., 2007; Xu et al., 2005). These interesting properties has lead us to synthesize the title compound (I), which contains the amino and pyridine groups in order to study its bioactivity and fluorescent properties. Our results show that (I) was inactive for antibacterial and tyrosinase inhibitory activities. However (I) exhibits weak fluorescence with the maximum emission at 437 nm when was excited at 310 nm. Herein the crystal structure of (I) is reported.

The molecule of the title chalcone derivative (Fig. 1), C₁₄H₁₂N₂O, exists in a E configuration with respect to the C8═C9 ethenyl bond [1.332 (2) Å] and the torsion angle C7–C8–C9–C10 = -176.57 (13)°. The molecule is twisted with a dihedral angle between the phenyl and pyridine rings being 29.38 (7)°. The prop-2-en-1-one unit (C7-C9/O1) is nearly planar [r.m.s. of 0.0384 (1) Å] and the torsion angle O1–C7–C8–C9 being -12.5 (2)°. This middle bridge makes the dihedral angles of 15.40 (9) and 16.30 (9)° with the phenyl and pyridine rings, respectively. The bond distances are of normal values (Allen et al., 1987) and are comparable with the related structure (Horkaew et al., 2010).

In the crystal packing, the molecules are linked by N—H···N and N—H···O hydrogen bonds (Table 1) into sheets parallel to the ab plane (Fig. 2). A π–π interaction with a Cg1···Cg1 distance of 3.6946 (10) Å is observed in the crystal; Cg1 is the centroid of the C10–C14/N1 ring. In addition C···C [3.3505 (19) Å; symmetry code 3/2-x, 1/2+y, z and 3.3776 (19) Å: symmetry code 3/2-x, -1/2+y, z], C···O [3.1312 (18) Å; symmetry code 3/2-x, -1/2+y, z] and N···O [2.9920 (16) Å; symmetry code 2-x,1/2+y,3/2-z] short contacts are also observed.

Experimental

The title compound was synthesized by condensation of 4-aminoacetophenone (0.40 g, 3 mmol) with 3-pyridinecarboxaldehyde (0.18 ml, 3 mmol) in ethanol (15 ml) in the presence of 10% NaOH (aq) (5 ml). After stirring for 2 hr at room temperature, the resulting yellow solid was collected by filtration, washed with distilled diethyl ether, dried and purified by repeated recrysallization from acetone. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from methanol by the slow evaporation of the solvent at room temperature after several days, Mp. 453-454 K.