[Journal logo]

Volume 68 
Part 12 
Page o3268  
December 2012  

Received 23 October 2012
Accepted 26 October 2012
Online 3 November 2012

[rk2384sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.005 Å
R = 0.075
wR = 0.184
Data-to-parameter ratio = 19.8
Details
Open access

1-Methyl-4-(4-methylstyryl)pyridinium 4-methylbenzenesulfonate

M. Krishnakumar,a S. Sudhahar,a A. Silambarasan,a G. Chakkaravarthib* and R. Mohankumarc*

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

In the title salt, C15H16N+·C7H7O3S-, the dihedral angle between the pyridine and benzene rings of the cation is 5.98 (18)°. In the crystal, adjacent anions and cations are linked by weak non-classical C-H...O hydrogen bonds and [pi]-[pi] interactions, with a centroid-centroid distance of 3.749 (2) Å.

Related literature

For molecular compounds with non-linear optical properties, see: Bosshard et al. (1995[Bosshard, Ch., Sutter, K., Pretre, Ph., Hulliger, J., Florsheimer, M., Kaatz, P. & Gunter, P. (1995). Organic Nonlinear Optical Materials. Advances in Nonlinear Optics, Vol. 1. Amsterdam: Gordon & Breach.]); Nalwa & Miyata (1997[Nalwa, H. S. & Miyata, S. (1997). In Nonlinear Optics of Organic Molecules and Polymers. Boca Raton: CRC Press.]). For related structures, see: Murugavel et al. (2009[Murugavel, S., SubbiahPandi, A., Srikanth, C. & Kalainathan, S. (2009). Acta Cryst. E65, o71.]); Sivakumar et al. (2012[Sivakumar, P. K., Krishnakumar, M., Kanagadurai, R., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3059.]); Okada et al. (1990[Okada, S., Masaki, A., Matsuda, H., Nakanishi, H., Kato, M. & Muramatsu, R. (1990). Jpn J. Appl. Phys. 29, 1112-1115.]).

[Scheme 1]

Experimental

Crystal data

  • C15H16N+·C7H7O3S-

  • Mr = 381.48

  • Monoclinic, P 21 /c

  • a = 9.1380 (6) Å

  • b = 6.4257 (5) Å

  • c = 33.884 (2) Å

  • [beta] = 95.004 (4)°

  • V = 1982.0 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 295 K

  • 0.28 × 0.22 × 0.20 mm
Data collection

  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.950, Tmax = 0.964

  • 18512 measured reflections

  • 4902 independent reflections

  • 3850 reflections with I > 2[sigma](I)

  • Rint = 0.031
Refinement

  • R[F2 > 2[sigma](F2)] = 0.075

  • wR(F2) = 0.184

  • S = 1.13

  • 4902 reflections

  • 247 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.57 e Å-3

  • [Delta][rho]min = -0.37 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O2i 0.93 2.42 3.273 (4) 152
C14-H14B...O1ii 0.96 2.59 3.482 (4) 155
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: RK2384 ).

Acknowledgements

The authors wish to acknowledge the SAIF, IIT Madras for the data collection. MK would also like to thank the Council of Scientific and Industrial Research (CSIR), New Delhi, for providing financial support (project No. 03 (1200)/EMR-II).

References

Bosshard, Ch., Sutter, K., Pretre, Ph., Hulliger, J., Florsheimer, M., Kaatz, P. & Gunter, P. (1995). Organic Nonlinear Optical Materials. Advances in Nonlinear Optics, Vol. 1. Amsterdam: Gordon & Breach.
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Murugavel, S., SubbiahPandi, A., Srikanth, C. & Kalainathan, S. (2009). Acta Cryst. E65, o71.  [CSD] [CrossRef] [details]
Nalwa, H. S. & Miyata, S. (1997). In 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]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [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] [details]

Acta Cryst (2012). E68, o3268  [ doi:10.1107/S1600536812044509 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.