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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 [sigma](C-C) = 0.005 Å
R = 0.066
wR = 0.176
Data-to-parameter ratio = 18.0
Details
Open access

3-(4-Methoxybenzyl)-1-benzothiophene

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[Bonini, C., Chiummiento, L., Bonis, M. D., Funicello, M., Lupattelli, P., Suanno, G., Berti, F. & Campaner, P. (2005). Tetrahedron, 61, 6580-6583.]); Brault et al. (2005[Brault, L., Migianu, E., Neguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757-760.]); Isloora et al. (2010[Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem., 45, 825-830.]). For related structures, see: Gunasekaran et al. (2009[Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.]); Umadevi et al. (2009[Umadevi, M., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2790.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C16H14OS

  • Mr = 254.33

  • Monoclinic, P c

  • a = 8.0158 (6) Å

  • b = 10.8230 (9) Å

  • c = 8.1219 (6) Å

  • [beta] = 112.563 (4)°

  • V = 650.68 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.946, Tmax = 0.954

  • 6033 measured reflections

  • 2946 independent reflections

  • 2721 reflections with I > 2[sigma](I)

  • Rint = 0.171

Refinement
  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.176

  • S = 1.06

  • 2946 reflections

  • 164 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1337 Friedel pairs

  • Flack parameter: -0.04 (11)

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
C14-H14...Cgi 0.93 2.83 3.617 (2) 143
Symmetry code: (i) x-1, y, z-1.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); 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.  [ISI] [CrossRef] [ChemPort]
Brault, L., Migianu, E., Neguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757-760.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Gunasekaran, B., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2455.  [CSD] [CrossRef] [details]
Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem., 45, 825-830.  [ISI] [PubMed]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Umadevi, M., Sureshbabu, R., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2009). Acta Cryst. E65, o2790.  [CrossRef] [details]


Acta Cryst (2010). E66, o1449  [ doi:10.1107/S1600536810018866 ]

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