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Volume 69 
Part 5 
Page o722  
May 2013  

Received 23 February 2013
Accepted 4 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.052
wR = 0.159
Data-to-parameter ratio = 18.4
Details
Open access

(E)-4-[2-(4-Ethoxyphenyl)ethenyl]-1-methylpyridinium naphthalene-2-sulfonate

aCentre for Crystal Growth, School of Advanced Sciences, VIT University, Vellore 632 014, India,bCrystal Growth and Crystallography Division, School of Advanced Sciences, VIT University, Vellore 632 014, India,cSophisticated Test and Instrumentation Centre (STIC), Cochin University PO, Cochin 682 022, Kerala, India, and dDepartment of Physics, Bangladesh University of Engineering and Technology, Dhaka 1000, Bangladesh
Correspondence e-mail: jpodder59@gmail.com

In the title salt, C16H18NO+·C10H7O3S-, the substituents attached to the central C=C bond adopt a trans conformation and the benzene and pyridinium rings are nearly coplanar, making a dihedral angle of 6.01 (9)°. The crystal structure features weak C-H...O hydrogen bonds and C-H...[pi] interactions .

Related literature

The title compound was synthesized as part of a search for materials with non-linear optical properties, see: Okada et al. (1990[Okada, S., Masaki, A., Matsuda, H., Nakanishi, H., Kato, M., Muramatsu, R. & Otsuka, M. (1990). Jpn. J. Appl. Phys. 29, 1112-1115.]); Yang et al. (2007[Yang, Z., Jazbinsek, M., Ruiz, B., Aravazhi, S., Gramlich, V. & Günter, P. (2007). Chem. Mater. 19, 3512-3518.]). For the synthesis of the pyridinium precursor, see: Okada et al. (1990[Okada, S., Masaki, A., Matsuda, H., Nakanishi, H., Kato, M., Muramatsu, R. & Otsuka, M. (1990). Jpn. J. Appl. Phys. 29, 1112-1115.]). For related compounds, see: Ruiz et al. (2006[Ruiz, B., Yang, Z., Gramlich, V., Jazbinsek, M. & Günter, P. (2006). J. Mater. Chem. 16, 2839-2842.]); Murugavel et al. (2009[Murugavel, S., SubbiahPandi, A., Srikanth, C. & Kalainathan, S. (2009). Acta Cryst. E65, o71.]).

[Scheme 1]

Experimental

Crystal data
  • C16H18NO+·C10H7O3S-

  • Mr = 447.53

  • Monoclinic, P 21 /n

  • a = 10.896 (1) Å

  • b = 17.2838 (16) Å

  • c = 11.8888 (10) Å

  • [beta] = 92.752 (4)°

  • V = 2236.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 296 K

  • 0.40 × 0.35 × 0.30 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.932, Tmax = 0.949

  • 9220 measured reflections

  • 5354 independent reflections

  • 3678 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.159

  • S = 1.03

  • 5354 reflections

  • 291 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C20-C24 ring.

D-H...A D-H H...A D...A D-H...A
C10-H10...O3i 0.93 2.52 3.433 (3) 168
C11-H11...O3ii 0.93 2.42 3.323 (3) 165
C12-H12B...O4ii 0.96 2.58 3.488 (3) 159
C15-H15...O2iii 0.93 2.31 3.189 (3) 158
C25-H25...O3iv 0.93 2.45 3.323 (3) 156
C14-H14...Cg1v 0.93 2.84 3.686 (3) 152
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x+1, y, z; (iv) -x, -y+1, -z; (v) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.])'; software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BH2474 ).


Acknowledgements

The authors acknowledge STIC, Cochin-682022, for single-crystal XRD facility. The authors also thank VIT University for providing the research facilities.

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [ISI] [details]
Bruker (1999). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2004). APEX2, SAINT and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [ISI] [CrossRef] [ChemPort] [details]
Murugavel, S., SubbiahPandi, A., Srikanth, C. & Kalainathan, S. (2009). Acta Cryst. E65, o71.  [CSD] [CrossRef] [details]
Okada, S., Masaki, A., Matsuda, H., Nakanishi, H., Kato, M., Muramatsu, R. & Otsuka, M. (1990). Jpn. J. Appl. Phys. 29, 1112-1115.  [CrossRef] [ChemPort] [ISI]
Ruiz, B., Yang, Z., Gramlich, V., Jazbinsek, M. & Günter, P. (2006). J. Mater. Chem. 16, 2839-2842.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Yang, Z., Jazbinsek, M., Ruiz, B., Aravazhi, S., Gramlich, V. & Günter, P. (2007). Chem. Mater. 19, 3512-3518.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o722  [ doi:10.1107/S1600536813009240 ]

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