(2E)-1-(5-Chloro­thio­phen-2-yl)-3-(2,3-dimeth­oxy­phen­yl)prop-2-en-1-one

A N Prabhu; A Jayarama; Ravish Sankolli; T N Guru Row; V Upadhyaya

doi:10.1107/S1600536811037135

. 2011 Sep 17;67(Pt 10):o2665. doi: 10.1107/S1600536811037135

(2E)-1-(5-Chlorothiophen-2-yl)-3-(2,3-dimethoxyphenyl)prop-2-en-1-one

A N Prabhu ^a, A Jayarama ^b, Ravish Sankolli ^c, T N Guru Row ^c, V Upadhyaya ^a,^*

PMCID: PMC3201439 PMID: 22058781

Abstract

In the title compound, C₁₅H₁₃ClO₃S, the chlorothiophene and dimethoxyphenyl groups are linked by a prop-2-en-1-one group. The C=C double bond exhibits an E conformation. The molecule is non-planar, with a dihedral angle of 31.12 (5)° between the chlorothiophene and dimethoxyphenyl rings. The methoxy group at position 3 is coplanar with the benzene ring to which it is attached, with a C—O—C—C torsion angle of −3.8 (3)°. The methoxy group attached at position 2 of the benzene ring is in a (+)synclinal conformation, as indicated by the C—O—C—C torsion angle of −73.6 (2)°. In the crystal, two different C—H⋯O intermolecular interactions generate chains of molecules extending along the b axis.

Related literature

For general background to chalcones and their biological properties, see: Choudary et al. (1999 ▶); Tomazela et al. (2000 ▶). For a related structure, see: Benmekhbi et al. (2009 ▶).

Experimental

Crystal data

C₁₅H₁₃ClO₃S
M _r = 308.76
Monoclinic,
a = 11.6139 (8) Å
b = 8.5605 (5) Å
c = 14.4174 (9) Å
β = 99.907 (2)°
V = 1412.02 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 296 K
0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T _min = 0.920, T _max = 0.936
9286 measured reflections
3087 independent reflections
2348 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.102
S = 1.07
3087 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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., 1996 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811037135/pv2439sup1.cif

e-67-o2665-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811037135/pv2439Isup2.hkl

e-67-o2665-Isup2.hkl^{(148.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811037135/pv2439Isup3.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
C2—H2⋯O1ⁱ	0.93	2.53	3.209 (2)	130
C15—H15A⋯O2ⁱⁱ	0.96	2.55	3.423 (3)	151

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

Acknowledgments

ANP is thankful to Manipal Institute of Technology, Manipal University.

supplementary crystallographic information

Comment

Chalcones represent one of the most abundant and ubiquitous group of natural products (Tomazela, et al., 2000). In the past few years, they have been shown to possess interesting biological properties and synthetic intermediates (Choudary, et al., 1999). In the title compound (Fig. 1), the chlorothiophene and dimethoxyphenyl groups are linked by a prop-2-en-1-one group. The chlorothiophene and dimethoxyphenyl rings are non-planar with the dihedral angle 31.12 (5)°. The torsion angle C15–O3–C12–C11 is 3.7 (3)° indicating that the O3 methoxy group is coplanar with the attached benzene ring. The other methoxy group at O2 is in a + synclinal conformation as indicated by the torsion angle 73.6 (2)° for C14–O2–C13–C12. The C═C double bond exhibits an E conformation (Benmekhbi, et al., 2009). The crystal structure is stabilized by two different C—H···O intermolecular interactions generating chains of molecules along the b-axis (Fig. 2).

Experimental

To synthesizethe the title compound, 2-acetyl-5-chlorothiophene (0.01 mol) and 2,3-dimethoxybenzaldehyde (0.01 mol) were dissolved in methanol (60 ml). Sodium hydroxide (5 ml, 20%) was then added drop wise to the solution, and it was stirred for 2 h. The contents of the flask were poured into ice-cold water, and the resulting crude solid was collected by filtration. The compound was dried and re-crystallized twice from acetone.