(4-Methyl­phen­yl)[2-(thio­phen-2-ylcarbon­yl)phen­yl]methanone

V Silambarasan; S Sundaramoorthy; R Sivasakthikumaran; A K MohanaKrishnan; D Velmurugan

doi:10.1107/S1600536811032478

. 2011 Aug 17;67(Pt 9):o2349. doi: 10.1107/S1600536811032478

(4-Methylphenyl)[2-(thiophen-2-ylcarbonyl)phenyl]methanone

V Silambarasan ^a, S Sundaramoorthy ^a, R Sivasakthikumaran ^b, A K MohanaKrishnan ^b, D Velmurugan ^a,^*

PMCID: PMC3200848 PMID: 22058965

Abstract

The crystal studied of the title compound, C₁₉H₁₄O₂S, was an inversion twin with a 0.7 (1):0.3 (1) domain ratio. The central benzene ring makes dihedral angles of 63.31 (9) and 60.86 (9)°, respectively, with the 4-methylphenyl and thiophene rings. In the crystal, molecules are linked by weak intermolecular C—H⋯O hydrogen bonds and S⋯π [3.609 (3) Å] interactions.

Related literature

For the biological activity of thiophene derivatives, see: Bonini et al. (2005 ▶); Brault et al. (2005 ▶); Isloora et al. (2010 ▶); Xia et al. (2010 ▶). For related structures, see: Ranjith et al. (2011 ▶); Dufresne & Skene (2010 ▶).

Experimental

Crystal data

C₁₉H₁₄O₂S
M _r = 306.36
Orthorhombic,
a = 6.8748 (2) Å
b = 13.3291 (4) Å
c = 16.8667 (5) Å
V = 1545.58 (8) Å³
Z = 4
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 = 0.948, T _max = 0.960
14787 measured reflections
3757 independent reflections
3073 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.154
S = 1.04
3757 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.38 e Å⁻³
Absolute structure: Flack (1983 ▶), 1564 Friedel pairs
Flack parameter: 0.31 (11)

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); 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/S1600536811032478/lx2197sup1.cif

e-67-o2349-sup1.cif^{(24.4KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032478/lx2197Isup2.hkl

e-67-o2349-Isup2.hkl^{(180.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811032478/lx2197Isup3.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
C9—H9⋯O2ⁱ	0.93	2.51	3.386 (3)	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

VS and DV thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection.

supplementary crystallographic information

Comment

Thiophene derivatives exhibit anti–HIVPR inhibitors (Bonini et al., 2005) and anti–breast cancer(Brault et al., 2005) activities. In addition, some of the benzo[b]thiophene derivatives show significant antimicrobial and anti–inflammatory activities (Isloora et al., 2010). The thiophene derivates have been viewed as significant compounds for application in many fields (Xia et al., 2010). Against this background, we report herein the crystal structure of the title compound.

The title compound crystallizes as the non–centrosymmetric space group P2₁2₁2₁ in spite of having no asymmetric C atoms. The crystal studied was an inversion twin with a 0.7 (1):0.3 (1) domain ratio.

In the title compound (Fig. 1), The bond lengths and angles agree with those observed in other thiophene derivative (Ranjith et al., 2011). The benzene ring makes the dihedral angles of 63.31 (9)° and 60.86 (9)°, respectively with the 4–methylphenyl and thiophene rings. The thiophene ring makes the dihedral angle of 75.04 (9)° with respect to 4–methylphenyl ring, it shows that both rings are almost perpendicular to each other. The molecular packing (Fig. 2) is stabilized by weak intermolecular C—H···O hydrogen bonds; the first one between a benzene H atom and the O atom of the C═O unit (Table 1, C8—H8···O1ⁱ), and the second one between a benzene H atom and the O atom of the C═O unit (Table 1, C9—H9···O2ⁱⁱ). The molecular packing (Fig. 2) is further stabilized by a weak intermolecular S···π interaction the thiophene S atom and the 4–methylphenyl ring, with a S1···Cg^iv [3.609 (3) Å] (Cg is the centroid of the C13–C18 phenyl ring).

Experimental

The furan 1 g was dissolved in THF. The weighted lead tetracetone (1.52 g, 1520 m mol) was added to the furan. Then it was refluxed at 343 K for 0.5 h. The reaction mixture was checked for TLC. Then the usual workup was done with brine solution and CHCl₃ follwed by column chromatography (10% AcOEt/hexane) lead to the solution of the pure compound. Single crystals suitable for X–ray diffraction were obtained by slow evaporation of a solution of the title compound in ethyl acetate at room temperature.