(E)-1-(5-Bromo­thio­phen-2-yl)-3-(3,4,5-trimeth­oxy­phen­yl)prop-2-en-1-one

Suresh B Vepuri; H C Devarajegowda; Waleed Fadl Ali Al-eryani; K Lavanya; S Anbazhagan

doi:10.1107/S1600536811049294

. 2011 Nov 30;67(Pt 12):o3474. doi: 10.1107/S1600536811049294

(E)-1-(5-Bromothiophen-2-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one

Suresh B Vepuri ^a,^*, H C Devarajegowda ^b, Waleed Fadl Ali Al-eryani ^b, K Lavanya ^a, S Anbazhagan ^c

PMCID: PMC3239100 PMID: 22199948

Abstract

In the title compound, C₁₆H₁₅BrO₄S, the dihedral angle between the thiophene and benzene rings is 13.08 (16)°. The C atoms of the meta methoxy groups of the substituted benzene ring lie close to the plane of the ring [displacements = 0.049 (5) and −0.022 (4) Å], whereas the para-C atom is significantly displaced [−1.052 (4) Å]. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming C(11) chains propagating in [100].

Related literature

For general background to chalcones see: Chun et al. (2001 ▶); Horng et al. (2003 ▶); Mei et al. (2003 ▶).

Experimental

Crystal data

C₁₆H₁₅BrO₄S
M _r = 383.25
Orthorhombic,
a = 16.8923 (7) Å
b = 8.0793 (6) Å
c = 23.6427 (17) Å
V = 3226.7 (4) Å³
Z = 8
Mo Kα radiation
μ = 2.69 mm⁻¹
T = 293 K
0.22 × 0.15 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2010 ▶) T _min = 0.625, T _max = 1.000
17608 measured reflections
2833 independent reflections
1944 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.074
S = 0.99
2833 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2010 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and CAMERON (Watkin et al., 1993 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811049294/hb6511sup1.cif

e-67-o3474-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811049294/hb6511Isup2.hkl

e-67-o3474-Isup2.hkl^{(136.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811049294/hb6511Isup3.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
C21—H21⋯O6ⁱ	0.93	2.46	3.320 (4)	155

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Professor T. N. Guru Row, SSCU, IISc, Bangalore, for support of the data collection. SBV thanks the Acharya Nagarjuna University, Gutntur, Andhrapradesh, for support of the part-time PhD programme in Pharmacy.

supplementary crystallographic information

Comment

Chalcones are alpha beta unsaturated ketones, widely distributed in nature and are extensively studied for their biological activity (e.g. Chun et al., 2001; Horng et al., 2003; Mei et al., 2003). In this paper we report the crystal structure of the title chalcone derivative, (I) (Fig. 1).

The unit cell contains eight molecules. The five-membered thiophene ring (S2\C19\···C22) is not coplanar with the phenyl ring (C10\C11\···C15) system; the dihedral angle between the two planes is 13.08 (16)°. The crystal structure displays intermolecular C21—H21···O6 and weak intramolecular C8—H8B···O5 and C9—H9B···O4 hydrogen bonds (Table 1). The packing of molecules in the crystal structure is depicted in Fig. 2.

Experimental

A mixture of 2-acetyl-5-BromoThiophene (0.01 mole) and 3,4,5-trimethoxybenzaldehyde (0.01 mole) were stirred in ethanol (30 ml) and then an aqueous solution of potassium hydroxide (40%,15 ml)was added to it. The mixture was kept over night at room temperature and then it was poured into crushed ice and acidified with dilute hydrochloric acid. The precipiteted chalcone was filtered and crystallized from ethanol to yield colourless prisms of (I).