(E)-3-(Anthracen-9-yl)-1-(2-bromo­phen­yl)prop-2-en-1-one

Hoong-Kun Fun; Thawanrat Kobkeatthawin; Jaruwan Joothamongkhon; Suchada Chantrapromma

doi:10.1107/S1600536810048476

. 2010 Nov 27;66(Pt 12):o3312–o3313. doi: 10.1107/S1600536810048476

(E)-3-(Anthracen-9-yl)-1-(2-bromophenyl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*,^‡, Thawanrat Kobkeatthawin ^b, Jaruwan Joothamongkhon ^b, Suchada Chantrapromma ^b,^§

PMCID: PMC3011387 PMID: 21589590

Abstract

The molecule of the title chalcone, C₂₃H₁₅BrO, is not planar and exists in the E configuration with respect to the central C=C bond. The dihedral angle between the benzene and anthracene rings is 83.58 (6)°. The prop-2-en-1-one bridge makes dihedral angles of 63.00 (7) and 42.62 (16)° with the benzene and anthracene rings, respectively. In the crystal, molecules are linked into dimers by weak C—H⋯O interactions. These dimers are arranged parallel to the bc plane and are further stacked along the a axis by π–π interactions with a centroid–centroid distance of 3.7561 (9) Å. The crystal structure is further stabilized by C—H⋯π interactions.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2009 ▶); Joothamongkhon et al. (2010 ▶). For background to and applications of chalcones, see: Cheng et al. (2008 ▶); Gaber et al. (2008 ▶); Joothamongkhon et al. (2010 ▶); Nawakowska et al. (2008) ▶; Patil & Dharmaprakash (2008 ▶); Tewtrakul et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₃H₁₅BrO
M _r = 387.25
Orthorhombic,
a = 7.8631 (1) Å
b = 20.0583 (3) Å
c = 20.7259 (3) Å
V = 3268.90 (8) Å³
Z = 8
Mo Kα radiation
μ = 2.52 mm⁻¹
T = 100 K
0.34 × 0.28 × 0.20 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.482, T _max = 0.629
22332 measured reflections
4766 independent reflections
3717 reflections with I > 2σ(I)
R _int = 0.038

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.073
S = 1.02
4766 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536810048476/rz2527sup1.cif

e-66-o3312-sup1.cif^{(20.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048476/rz2527Isup2.hkl

e-66-o3312-Isup2.hkl^{(233.6KB, hkl)}

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5A⋯O1ⁱ	0.93	2.53	3.301 (2)	140
C15—H15A⋯Cg1ⁱⁱ	0.93	2.99	3.6989 (19)	135

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

Acknowledgments

The authors thank the Prince of Songkla University for financial support. The authors also thank Universiti Sains Malaysia for the Research University Golden Goose (grant No. 1001/PFIZIK/811160).

supplementary crystallographic information

Comment

Chalcones have been studied for their chemical and biological activities for a long time. They have a wide range of applications such as in non-linear optical devices (Patil & Dharmaprakash, 2008) and have various biological properties such as analgesic, anti-inflammatory, antibacterial, antifungal (Nawakowska et al., 2008; Cheng et al., 2008) and HIV-1 protease inhibitory (Tewtrakul et al., 2003) activities. Moreover, chalcones have also been studied for fluorescent property (Gaber et al., 2008). Our previous investigation has revealed that chalcones containing the anthracene moiety displayed fluorescent property (Joothamongkhon et al., 2010). The title compound (I) was synthesized for further investigation of its fluorescent properties. The title compound in chloroform solution exhibited fluorescence with the maximum emission at 450 nm when it was excited at 380 nm.

The molecule of (I) (Fig. 1) exists in an E configuration with respect to the C8═C9 double bond [1.343 (2)°], with the torsion angle C7–C8–C9–C10 = 174.24 (16)°. The anthracene unit is essentially planar with the r.m.s. 0.0416 (2) Å. The molecule is not planar as indicated by the dihedral angle between benzene and anthracene rings of 83.58 (6)°. The mean plane through the pro-2-en-1-one bridge (C7–C9/O1) [r.m.s. 0.0283 (2) Å] makes dihedral angles of 63.00 (7) and 42.62 (16)° with the benzene and anthracene rings, respectively. The bond distances are of normal values (Allen et al., 1987) and are comparable with those of related structures (Fun et al., 2009; Joothamongkhon et al., 2010).

In the crystal packing, the molecules are linked into dimers through the C5—H5A···O1 interactions (Fig. 2). These dimers are arranged into sheets parallel to the bc plane, and are further stacked along the a axis by π–π interaction with a Cg₂···Cg₃ distance of 3.7561 (9) Å (symmetry code: -1/2 + x, y, 1/2 - z). The crystal structure is further stabilized by C—H···π interactions (Table 1); Cg₁, Cg₂ and Cg₃ are the centroids of the C1–C6, C10–C11/C16–C18/C23 and C11–C16 rings, respectively.

Experimental

The title compound was synthesized by condensation of 2-bromoacetophenone (0.39 g, 2 mmol) with anthracene-9-carboxaldehyde (0.41 g, 2 mmol) in ethanol (40 ml) in the presence of 20% NaOH (aq) (5 ml). After stirring for 7 h at room temperature, the yellow solid obtained was collected by filtration, washed with distilled water and dried in air. Yellow block-shaped single crystals of the title compound suitable for x-ray structure determination were recrystalized from methanol by slow evaporation of the solvent at room temperature after several days. Mp. 427–428 K.