(E)-3-(3,4-Dimethoxy­phen­yl)-1-(2-thien­yl)prop-2-en-1-one

Hoong-Kun Fun; Samuel Robinson Jebas; P S Patil; S M Dharmaprakash

doi:10.1107/S1600536808020631

. 2008 Jul 9;64(Pt 8):o1440. doi: 10.1107/S1600536808020631

(E)-3-(3,4-Dimethoxyphenyl)-1-(2-thienyl)prop-2-en-1-one

Hoong-Kun Fun ^a,^*, Samuel Robinson Jebas ^a,^‡, P S Patil ^b, S M Dharmaprakash ^b

PMCID: PMC2962071 PMID: 21203155

Abstract

The title compound, C₁₅H₁₄O₃S, has two symmetry-independent molecules in the asymmetric unit with almost identical geometry. The dihedral angle between the benzene and thiophene rings is 1.61 (11)° in one molecule and 7.21 (11)° in the other. In both molecules, C—H⋯O hydrogen bonds generate rings of graph-set motif S(5). The crystal structure is stabilized by C—H⋯O hydrogen bonds, C—H⋯π interactions and π–π interactions involving the benzene and thiophene rings, with centroid–centroid distances of 3.5249 (13) and 3.6057 (13) Å.

Related literature

For related literature on the biological and non-linear optical properties of chalcone derivatives, see: Agrinskaya et al. (1999 ▶); Chopra et al. (2007 ▶); Patil et al. (2006 ▶); Patil, Ng et al. (2007 ▶); Patil, Fun et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis of hydrogen-bond patterns, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₅H₁₄O₃S
M _r = 274.32
Monoclinic,
a = 12.1509 (3) Å
b = 14.3118 (3) Å
c = 16.3692 (4) Å
β = 106.570 (2)°
V = 2728.41 (11) Å³
Z = 8
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100.0 (1) K
0.60 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.871, T _max = 0.974
31879 measured reflections
7997 independent reflections
4723 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.060
wR(F ²) = 0.158
S = 1.07
7997 reflections
347 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.44 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/S1600536808020631/ci2626sup1.cif

e-64-o1440-sup1.cif^{(25.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020631/ci2626Isup2.hkl

e-64-o1440-Isup2.hkl^{(383.4KB, hkl)}

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
C7A—H7AA⋯O1A	0.93	2.43	2.792 (3)	103
C1B—H1BA⋯O1Aⁱ	0.93	2.36	3.261 (3)	162
C7B—H7BA⋯O1B	0.93	2.47	2.816 (3)	102
C14B—H14F⋯O1Bⁱⁱ	0.96	2.53	3.401 (3)	151
C15A—H15A⋯Cg1ⁱⁱⁱ	0.96	2.92	3.616 (3)	130
C10A—H10A⋯Cg3^iv	0.93	2.84	3.636 (3)	144
C3A—H3AA⋯Cg4	0.93	2.79	3.370 (3)	122

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1, Cg3 and Cg4 are the centroids of the S1A/C1A–C4A, S1B/C1B–C4B and C8B–C13B rings, respectively.

Acknowledgments

FHK and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks the Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

The synthesis and structural studies of chalcone derivatives have been of immense interest because of their biological as well as their increasingly important nonlinear optical properties (Agrinskaya et al., 1999; Chopra et al. 2007). We have previously reported the crystal structures of D–π–A type chalcone derivatives (Patil et al.. 2006; Patil, Ng et al., 2007; Patil, Fun et al., 2007). In continuation of our interest in these compounds, we report herein the crystal structure of the title compound, (I).

There are two independent molecules (A and B) in the asymmetric unit of (I), with similar geometries (Fig. 1). The bond lengths and angles are found to have normal values (Allen et al., 1987). The thiophene rings in both the molecules are planar, with a maximum deviation of 0.002 (3) Å for atom C2A and -0.007 (3) Å for atom C3B. The dihedral angle between the benzene and thiophene rings is 1.61 (11)° in molecule A and 7.21 (11)° in molecule B. In each of the independent molecule, an intramolecular C—H···O hydrogen bond generates an S(5) ring motif (Bernstein et al., 1995).

The crystal structure is consolidated by weak C—H···O and C—H···π interactions (Table 1). The packing is further strengthened by π–π interactions between the S1A/C1A–C4A (centroid Cg1) and C8A–C13A (centroid Cg2) rings [Cg1···Cg2ⁱ = 3.5249 (13) Å] and between the S1B/C1B–C4B (centroid Cg3) and C8B–C13B (centroid Cg4) rings [Cg3···Cg4ⁱⁱ = 3.6057 (13) Å] [symmetry codes: (i) -x, 1-y, -z; (ii) -x, 1-y, -z].

Experimental

The title compound was synthesized by the condensation of 3,4-dimethoxybenzaldehyde (0.01 mol, 1.66 g) with 2-acetylthiophene (0.01 mol, 1.07 ml) in methanol (60 ml) in the presence of a catalytic amount of sodium hydroxide solution (5 ml, 30%). After stirring for 6 h, the contents of the flask were poured into ice-cold water (500 ml) and left to stand for 5 h. The resulting crude solid was filtered and dried. The compound was recrystallized from acetone.