(E)-3-(Anthracen-9-yl)-1-(4-bromo­phen­yl)prop-2-en-1-one

Thitipone Suwunwong; Suchada Chantrapromma; Chatchanok Karalai; Paradorn Pakdeevanich; Hoong-Kun Fun

doi:10.1107/S1600536809003122

. 2009 Jan 31;65(Pt 2):o420–o421. doi: 10.1107/S1600536809003122

(E)-3-(Anthracen-9-yl)-1-(4-bromophenyl)prop-2-en-1-one¹

Thitipone Suwunwong ^a, Suchada Chantrapromma ^b,^*, Chatchanok Karalai ^b, Paradorn Pakdeevanich ^c, Hoong-Kun Fun ^d,^‡

PMCID: PMC2968141 PMID: 21582009

Abstract

In the title molecule, C₂₃H₁₅BrO, the prop-2-en-1-one unit is planar and it makes dihedral angles of 20.9 (1) and 45.8 (1)°, respectively, with the 4-bromophenyl ring and the anthracene ring system. The interplanar angle between the 4-bromophenyl ring and the anthracene ring system is 35.52 (7)°. In the crystal structure, molecules are linked into dimers by C—H⋯Br hydrogen bonds, and the dimers are linked into a zigzag network parallel to the bc plane by weak C—H⋯O hydrogen bonds and C—H⋯π interactions involving the central benzene ring of the anthracene ring system.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Ng et al. (2006 ▶); Patil et al. (2006 ▶); Patil, Chantrapromma et al. (2007 ▶); Suwunwong et al. (2009 ▶). For background and applications of chalcones, see: Jung et al. (2008 ▶); Patil, Chantrapromma et al. (2007 ▶); Patil, Dharmaprakash et al. (2007 ▶); Patil & Dharmaprakash (2008 ▶); Prasad et al. (2008 ▶).

Experimental

Crystal data

C₂₃H₁₅BrO
M _r = 387.25
Monoclinic,
a = 5.3792 (1) Å
b = 19.1030 (4) Å
c = 16.3005 (4) Å
β = 95.944 (1)°
V = 1666.02 (6) Å³
Z = 4
Mo Kα radiation
μ = 2.47 mm⁻¹
T = 100.0 (1) K
0.57 × 0.27 × 0.15 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.331, T _max = 0.714
29994 measured reflections
4866 independent reflections
3803 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.076
S = 1.02
4866 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.54 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003122/ci2756sup1.cif

e-65-0o420-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809003122/ci2756Isup2.hkl

e-65-0o420-Isup2.hkl^{(238.4KB, hkl)}

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

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

Cg1 is the centroid of the C18–C23 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O1ⁱ	0.93	2.42	3.308 (2)	159
C13—H13A⋯O1ⁱⁱ	0.93	2.57	3.288 (2)	135
C21—H21A⋯Br1ⁱⁱⁱ	0.93	2.93	3.4722 (19)	119
C9—H9A⋯Cg1^iv	0.93	2.83	3.4479 (18)	125

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

Acknowledgments

Financial support from the Center of Excellence for Innovation in Chemistry (PERCH-CIC), Commision on Higher Education, Ministry of Education, Thailand, is gratefully acknowledged. The authors also thank the Thailand Research Fund (TRF) and the Prince of Songkla University for financial support, and the Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

supplementary crystallographic information

Comment

Chalcones are compounds which have a wide range of applications covering from non-linear optical (Patil & Dharmaprakash, 2008) and electro-active fluorescent materials (Jung et al., 2008) to materials with various biological activities (Prasad et al., 2008). Our previous work (Patil Dharmaprakash et al., 2007) has reported that 1-(4-bromophenyl)-3-(2,4,5-trimethoxyphenyl)-propenone shows efficient second-order nonlinear optical properties. The various interesting properties of chalcone derivatives lead us to synthesize the title chalcone derivative in order to study its photoluminescence and antimicrobial activities.

The molecule of the title chalcone derivative (Fig. 1) exists in an E configuration with respect to the C8═C9 double bond [1.333 (2) Å]. The anthracene ring system is planar, with atom C21 deviating a maximum of 0.147 (2) Å. The molecule is twisted as indicated by the interplanar angle between 4-bromophenyl ring and anthracene ring system of 35.52 (7)°, and torsion angles C5–C6–C7–C8 of 22.9 (1)° and C8–C9–C10–C23 of -50.2 (3)°. The pro-2-en-1-one unit (C7-C9/O1) is planar as evidenced by the torsion angle O1–C7–C8–C9 of 0.1 (3)°. The O1/C6-C9 plane makes dihedral angles of 20.9 (1)° and 45.8 (1)°, respectively, with the 4-bromophenyl ring and anthracene ring system. The bond distances show normal values (Allen et al., 1987) and are comparable with those observed in related structures (Ng et al., 2006; Patil et al., 2006; Patil, Chantrapromma et al., 2007; Suwunwong et al., 2009).

In the crystal packing (Fig. 2), the molecules are linked into dimers by weak C—H···Br interactions (Table 1) and the dimers are further linked into a zigzag network parallel to the bc plane by weak C—H···O and C—H···π interactions (Table 1).

Experimental

The title compound was synthesized by the condensation of anthracene-9-carbaldehyde (0.01 mol) with 4-bromoacetophenone (0.01 mol) in ethanol (40 ml) in the presence of NaOH (10 ml, 10%). After stirring for 2 h, a yellow solid appeared and was then collected by filtration, washed with distilled water, dried and purified by repeated recrystallization from acetone. Yellow plate-shaped single crystals of the title compound suitable for X-ray structure determination were obtained by slow evaporation of an acetone solution at room temperature after several days.