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Volume 69 
Part 5 
Page o694  
May 2013  

Received 1 April 2013
Accepted 4 April 2013
Online 10 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.049
wR = 0.130
Data-to-parameter ratio = 21.9
Details
Open access

4-(4-Bromostyryl)-1-methylpyridinium tosylate

aDepartment of Physics, Presidency College, Chennai 600 005, India, and bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India
Correspondence e-mail: chakkaravarthi_2005@yahoo.com, mohan66@hotmail.com

In the cation of the title compound, C14H13BrN+·C7H7O3S-, the dihedral angle between the benzene and pyridine rings is 8.34 (11)°. The Br atom is disordered over two positions with site occupancies of 0.74 (2) and 0.26 (2). The molecular structure is stabilized by a weak intramolecular C-H...O interactions. The crystal structure exhibits weak C-H...O and [pi]-[pi] [centroid-centroid distance = 3.7466 (17) Å] interactions, forming a three dimensional network.

Related literature

For molecular compounds with non-linear optical properties, see: Bosshard et al. (1995[Bosshard, Ch., Sutter, K., Prêtre, Ph., Hulliger, J., Flörsheimer, M., Kaatz, P. & Günter, P. (1995). Editors. Organic Nonlinear Optical Materials. Advances in Nonlinear Optics, Vol. 1. Amsterdam: Gordon & Breach.]); Nalwa & Miyata (1997[Nalwa, H. S. & Miyata, S. (1997). Nonlinear Optics of Organic Molecules and Polymers. Boca Raton: CRC Press.]). For similar structures, see: Krishnakumar et al. (2012[Krishnakumar, M., Sudhahar, S., Silambarasan, A., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3268.]); Okada et al. (1990[Okada, S., Masaki, A., Matsuda, H., Nakanishi, H., Kato, M. & Muramatsu, R. (1990). Jpn. J. Appl. Phys. 29, 1112-1115.]); Sivakumar et al. (2012[Sivakumar, P. K., Krishnakumar, M., Kanagadurai, R., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3059.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13BrN+·C7H7O3S-

  • Mr = 446.35

  • Monoclinic, P 21 /c

  • a = 9.0502 (2) Å

  • b = 6.4201 (1) Å

  • c = 33.9280 (7) Å

  • [beta] = 94.469 (1)°

  • V = 1965.33 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.22 mm-1

  • T = 295 K

  • 0.28 × 0.22 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.]) Tmin = 0.575, Tmax = 0.665

  • 22764 measured reflections

  • 5596 independent reflections

  • 3012 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.049

  • wR(F2) = 0.130

  • S = 1.01

  • 5596 reflections

  • 256 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C10-H10...O1 0.93 2.57 3.415 (3) 151
C12-H12...O2i 0.93 2.39 3.247 (3) 153
C14-H14B...O1ii 0.96 2.53 3.438 (4) 157
Symmetry codes: (i) x-1, y-1, z; (ii) x, y-1, z.

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: BT6900 ).


Acknowledgements

MK would like to thank the Council of Scientific and Industrial Research, New Delhi, India, for providing financial support [project No. 03 (1200)/11/EMR-II)].

References

Bosshard, Ch., Sutter, K., Prêtre, Ph., Hulliger, J., Flörsheimer, M., Kaatz, P. & Günter, P. (1995). Editors. Organic Nonlinear Optical Materials. Advances in Nonlinear Optics, Vol. 1. Amsterdam: Gordon & Breach.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Krishnakumar, M., Sudhahar, S., Silambarasan, A., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3268.  [CSD] [CrossRef] [details]
Nalwa, H. S. & Miyata, S. (1997). Nonlinear Optics of Organic Molecules and Polymers. Boca Raton: CRC Press.
Okada, S., Masaki, A., Matsuda, H., Nakanishi, H., Kato, M. & Muramatsu, R. (1990). Jpn. J. Appl. Phys. 29, 1112-1115.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Sivakumar, P. K., Krishnakumar, M., Kanagadurai, R., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3059.  [CSD] [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o694  [ doi:10.1107/S1600536813009227 ]

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