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Volume 69 
Part 5 
Page o709  
May 2013  

Received 7 April 2013
Accepted 8 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.005 Å
R = 0.069
wR = 0.160
Data-to-parameter ratio = 19.3
Details
Open access

4-[2-(4-Butoxyphenyl)ethenyl]-1-methylpyridinium tosylate

aDepartment of Physics, Presidency College, Chennai 600 005, India,bDepartment of Physics, CPCL Polytechnic College, Chennai 600 068, India, and cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Maraimalai Campus, Chennai 600 025, India
Correspondence e-mail: chakkaravarthi_2005@yahoo.com, mohan66@hotmail.com

In the title molecular salt, C18H22NO+·C7H7O3S-, the dihedral angle between the aromatic rings in the cation is 10.00 (9)°; its alkyl side chain adopts an extended conformation. In the crystal, weak C-H...O and [pi]-[pi] [centroid-centroid distance = 3.7658 (17) Å] interactions link the components, generating a three-dimensional network.

Related literature

For molecular compounds with non-linear optical properties, see: 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: Krishnakumar et al. (2012[Krishnakumar, M., Sudhahar, S., Silambarasan, A., Chakkaravarthi, G. & Mohankumar, R. (2012). Acta Cryst. E68, o3268.]); 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
  • C18H22NO+·C7H7O3S-

  • Mr = 439.55

  • Monoclinic, P 21 /n

  • a = 9.0884 (6) Å

  • b = 6.4559 (5) Å

  • c = 39.827 (3) Å

  • [beta] = 95.404 (3)°

  • V = 2326.4 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 295 K

  • 0.28 × 0.24 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.954, Tmax = 0.967

  • 20608 measured reflections

  • 5629 independent reflections

  • 4258 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.069

  • wR(F2) = 0.160

  • S = 1.16

  • 5629 reflections

  • 291 parameters

  • 2 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...O4i 0.93 2.33 3.210 (3) 158
C4-H4...O3ii 0.93 2.56 3.412 (3) 153
C6-H6B...O3iii 0.96 2.57 3.470 (4) 157
C8-H8...O3ii 0.93 2.55 3.418 (3) 156
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

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: HB7067 ).


Acknowledgements

MK thanks the Council of Scientific and Industrial Research, New Delhi, India, for financial support (project No. 03 (1200)/11/EMR-II).

References

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). In Nonlinear Optics of Organic Molecules and Polymers. Boca Raton: CRC Press.
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, o709  [ doi:10.1107/S1600536813009616 ]

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