(3,4-Dimeth­oxy­phen­yl)[2-(thio­phen-2-ylcarbon­yl)phen­yl]methanone

G Ganesh; R Sivasakthikumaran; E Govindan; A K Mohana Krishnan; A SubbiahPandi

doi:10.1107/S1600536812037336

. 2012 Sep 5;68(Pt 10):o2844. doi: 10.1107/S1600536812037336

(3,4-Dimethoxyphenyl)[2-(thiophen-2-ylcarbonyl)phenyl]methanone

G Ganesh ^a, R Sivasakthikumaran ^b, E Govindan ^c, A K Mohana Krishnan ^b, A SubbiahPandi ^c,^*

PMCID: PMC3470204 PMID: 23125648

Abstract

In the title compound, C₂₀H₁₆O₄S, the thiophene ring makes dihedral angles of 72.9 (2) and 60.5 (2)°, respectively, with the dimethoxy benzene and phenyl rings. In the crystal, C—H⋯O hydrogen bonds link the molecules into a C(9) chain along the b axis. The S and C atoms of the thiophene ring are disordered over two sets of sites [site occupancies = 0.675 (3) and 0.325 (3)]. A short intermolecular S⋯O contact [3.084 (2) Å] is observed in the crystal structure, which also features C—H⋯π interactions.

Related literature

For background to thiophene derivatives and their biological activity, see: Bonini et al. (2005 ▶); Khan et al. (2009 ▶); Brault et al. (2005 ▶); Isloora et al. (2010 ▶); Xia et al. (2010 ▶). For related structures, see: Asiri et al. (2010 ▶); Aslam et al. (2011 ▶).

Experimental

Crystal data

C₂₀H₁₆O₄S
M _r = 352.40
Orthorhombic,
a = 15.7324 (6) Å
b = 10.7988 (5) Å
c = 20.4877 (11) Å
V = 3480.7 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 293 K
0.25 × 0.22 × 0.19 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.950, T _max = 0.961
22015 measured reflections
4469 independent reflections
2968 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.107
S = 1.03
4469 reflections
236 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037336/bt5963sup1.cif

e-68-o2844-sup1.cif^{(27.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037336/bt5963Isup2.hkl

e-68-o2844-Isup2.hkl^{(219.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812037336/bt5963Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812037336/bt5963Isup4.cml

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

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

Cg2 is the centroid of the C17/C19/C20/S1′/C18′ ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4ⁱ	0.93	2.58	3.496 (2)	169
C1—H1A⋯Cg2ⁱⁱ	0.96	2.99	3.799 (3)	143

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

Acknowledgments

The authors thank Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Thiophene derivatives exhibit anti-HIVPR inhibition (Bonini et al., 2005) and antibreast cancer (Brault et al., 2005) activity. In addition, some of the benzo[b]thiophene derivatives show significant antimicrobial and anti-inflammatory activity (Isloora et al., 2010). Thiophene derivates have been viewed as significant compounds for applications in many fields (Xia et al., 2010). Schiff bases are well known ligands in coordination chemistry with a wide range of biological activities (Khan et al., 2009). Against this background, and in order to obtain detailed information on molecular the solid state, an X-ray study of the title compound was carried out.

X-Ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The bond lengths S1—C20 and O2—C8 are normal and comparable to the corresponding values observed in the related structure of (2E)-1-(2,5-Dimethyl-3-thienyl)-3-(2-methoxyphenyl)prop-2-en-1-one (Asiri et al., 2010). The thiophene ring system makes dihedral angles of 72.9 (2) ° and 60.5 (2) °, respectively, with the dimethoxy benzene and the phenyl ring. The atoms O1 and O2 are deviated by -0.002 (1) Å and -0.010 (1) Å from the least squares plane of the C2—C7 ring. The atoms C18 and S1 of the thiophene ring are disordered over two positions [site occupancies = 0.648 (2) and 0.352 (2)].

The atom C3 acts as a donor to the atom O4 of the neighbour molecule at (-x,-1/2 + y, -z). This hydrogen bond is involved in a motif C(9) chain along b axis. Interestingly, a short non-hydrogen intermolecular contact between S1···O2 [3.084 (2) Å] at (1/2 - x,1 - y,-1/2 + z) was observed in the crystal structure. In addition to van der Waals interactions, the crystal packing is stabilized by C—H···π interaction between one of the methyl H atom (H1A) and the centroid (Cg2) of the thiophene ring (Table 1).

Experimental

To a stirred suspension of benzoic (1 g, 3.44 mmol) in dry THF (20 ml) lead tetra acetate (1.5 g, 3.42 mmol) was added and refluxed at 50 °C for half an hour. The reaction mixture was then poured into water (200 ml) and extracted with ethyl acetate (2x20 ml), washed with brine solution and dried (Na₂SO₄). The removal of solvent in vacuo afforded the crude product upon crystallization from methanol furnished the title compound as a color less solid.