3-(4-Methoxy­benz­yl)-1-benzothio­phene

Gunasekaran, B.; Dhayalan, V.; Mohanakrishnan, A.K.; Chakkaravarthi, G.; Manivannan, V.

doi:10.1107/S1600536810018866

Volume 66
Part 6
Page o1449
June 2010

Received 19 May 2010
Accepted 20 May 2010
Online 26 May 2010

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.005 Å
R = 0.066
wR = 0.176
Data-to-parameter ratio = 18.0
Details

3-(4-Methoxybenzyl)-1-benzothiophene

B. Gunasekaran,^a V. Dhayalan,^b A. K. Mohanakrishnan,^b G. Chakkaravarthi ^c and V. Manivannan ^d ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India,^bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India,^cDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
Correspondence e-mail: crystallography2010@gmail.com

In the title compound, C₁₆H₁₄OS, the dihedral angle between the benzothiophene ring system and the benzene ring is 72.41 (12)°. A weak intermolecular C-H [pi] interaction from the benzene ring to the benzothiophene ring system is observed in the crystal structure.

Related literature

For the biological activity of thiophene derivatives, see: Bonini et al. (2005); Brault et al. (2005); Isloora et al. (2010). For related structures, see: Gunasekaran et al. (2009); Umadevi et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₆H₁₄OS
M_r = 254.33
Monoclinic, P c
a = 8.0158 (6) Å
b = 10.8230 (9) Å
c = 8.1219 (6) Å
= 112.563 (4)°
V = 650.68 (9) Å³
Z = 2
Mo K radiation
= 0.23 mm^-1
T = 295 K
0.25 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.946, T_max = 0.954
6033 measured reflections
2946 independent reflections
2721 reflections with I > 2(I)
R_int = 0.171

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.176
S = 1.06
2946 reflections
164 parameters
2 restraints
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.48 e Å^-3
Absolute structure: Flack (1983), 1337 Friedel pairs
Flack parameter: -0.04 (11)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-HA	D-H	HA	DA	D-HA
C14-H14Cgⁱ	0.93	2.83	3.617 (2)	143
Symmetry code: (i) x-1, y, z-1.

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: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS2551 ).

Acknowledgements

BG thanks AMET University management, India, for their kind support.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bonini, C., Chiummiento, L., Bonis, M. D., Funicello, M., Lupattelli, P., Suanno, G., Berti, F. & Campaner, P. (2005). Tetrahedron, 61, 6580-6583.
Brault, L., Migianu, E., Neguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757-760.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.
Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem., 45, 825-830.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Umadevi, M., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2790.

organic compounds