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

Thawanrat Kobkeatthawin; Suchada Chantrapromma; Nisakorn Saewan; Hoong-Kun Fun

doi:10.1107/S1600536811014024

. 2011 Apr 22;67(Pt 5):o1204–o1205. doi: 10.1107/S1600536811014024

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

Thawanrat Kobkeatthawin ^a, Suchada Chantrapromma ^a,^*,^‡, Nisakorn Saewan ^b, Hoong-Kun Fun ^c,^§

PMCID: PMC3089117 PMID: 21754504

Abstract

The molecule of the title chalcone derivative, C₁₉H₁₅NO, exists in a trans configuration with respect to the C=C double bond. The molecule is slightly twisted with a dihedral angle of 6.12 (12)° between the benzene ring and the naphthalene ring system. The prop-2-en-1-one bridge is nearly planar, with an r.m.s. deviation of 0.0194 (2), and makes dihedral angles of 8.05 (19) and 11.47 (18)° with the benzene ring and the naphthalene ring system, respectively. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains along the b axis. Weak N—H⋯π and C—H⋯π interactions and a short N⋯O contact [2.974 (4) Å] are also observed.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2008 ▶); Horkaew et al. (2010 ▶). For background to and applications of chalcones, see: Bandgar & Gawande (2010 ▶); Cheng et al. (2008) ▶; Gaber et al. (2008 ▶); Nerya et al. (2004 ▶); Nowakowska et al. (2008 ▶); Patil et al. (2007 ▶); Svetlichny et al. (2007 ▶); Tewtrakul et al. (2003 ▶); Xu et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C₁₉H₁₅NO
M _r = 273.32
Orthorhombic,
a = 5.7422 (6) Å
b = 9.8022 (10) Å
c = 25.504 (3) Å
V = 1435.5 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 100 K
0.32 × 0.28 × 0.07 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.976, T _max = 0.994
8109 measured reflections
1940 independent reflections
1633 reflections with I > 2σ(I)
R _int = 0.042

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.119
S = 1.14
1940 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.24 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 datablocks global, I. DOI: 10.1107/S1600536811014024/rz2579sup1.cif

e-67-o1204-sup1.cif^{(19KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811014024/rz2579Isup2.hkl

e-67-o1204-Isup2.hkl^{(95.5KB, hkl)}

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

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

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C12/C17–C19 and C12–C17 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1ⁱ	0.90 (4)	2.12 (4)	2.974 (4)	159 (4)
N1—H2N1⋯Cg1ⁱⁱ	0.86 (4)	2.99 (4)	3.475 (3)	118 (3)
C5—H5A⋯Cg3ⁱⁱⁱ	0.93	2.82	3.513 (3)	132
C11—H11A⋯Cg3^iv	0.93	2.92	3.631 (3)	135
C13—H13A⋯Cg2^iv	0.93	2.86	3.551 (3)	132
C16—H16A⋯Cg1ⁱⁱⁱ	0.93	2.87	3.603 (4)	136

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

Acknowledgments

The authors thank the Thailand Research Fund (TRF) for the 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 the precursors of flavonoids and antiflavonoids which are available in plenty in ferns and higher plants. Their derivatives are known to display a variety of biological properties such as analgesic, anti-inflammatory, antibacterial and antifungal activities (Bandgar & Gawande, 2010; Cheng et al., 2008; Nowakowska et al., 2008), HIV-1 protease inhibitory (Tewtrakul et al., 2003) and tyrosinase inhibitory (Nerya et al., 2004) activities. Moreover, some of them have also been studied for fluorescent property (Gaber et al., 2008) and used for sensor, liquid crystal display and fluorescence probe for sensing of DNA or proteins (Svetlichny et al., 2007; Xu et al., 2005). In addition, some of them exhibit second harmonic generation (SHG), and hence are used in non-linear optical (NLO) applications (Patil et al., 2007). These interesting properties of chalcones have lead us to synthesize the title compound, (I), which contains the amino and fluorophore (naphthalene) groups in order to study its NLO and fluorescent properties. Compound (I) crystallizes in the chiral orthorhombic P2₁2₁2₁ space group and should therefore exhibit second-order nonlinear optical properties. (I) also shows fluorescent emission at 440 nm when excited at 380 nm. Our results also showed that (I) was inactive for tyrosinase inhibitory. Herein the crystal structure of (I) is reported.

The molecule of the title chalcone derivative (Fig. 1), C₁₉H₁₅NO, exists in an E configuration with respect to the C8═C9 ethenyl bond [1.330 (4) Å], as indicated by the torsion angle C7–C8–C9–C10 = 179.1 (3)°. The molecule is slightly twisted with the dihedral angle between the benzene and naphthalene rings of 6.12 (12)°. The prop-2-en-1-one unit (C7—C9/O1) is nearly planar [r.m.s. of 0.0194 (2) Å] and the torsion angle O1–C7–C8–C9 is 6.4 (5)°. This middle bridge makes dihedral angles of 8.05 (19) and 11.47 (18) ° with the benzene and naphthalene rings, respectively. The bond distances are of normal values (Allen et al., 1987) and are comparable with those found in related structures (Fun et al., 2008; Horkaew et al., 2010).

In the crystal packing, the molecules are linked by N—H···O hydrogen bonds (Table 1) into chains along the b axis (Fig. 2). N—H···π and C—H···π weak interactions (Table 1) are present in the crystal. In addition, a N···O short contact [2.974 (4) Å; symmetry code 2 - x, 1/2 + y, 3/2 - z] is also observed.

Experimental

The title compound was synthesized by condensation of 4-aminoacetophenone (0.40 g, 3 mmol) with 2-naphthaldehyde (0.46 g, 3 mmol) in ethanol (25 ml) in the presence of 20% NaOH(aq) (5 ml). After stirring for 6 h at room temperature, the resulting yellow solid was collected by filtration, washed with distilled diethylether, dried and purified by repeated recrysallization from acetone. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were recrystalized from acetone by slow evaporation of the solvent at room temperature after several days. M.p. 416–417 K.