4-{2-[4-(Dimethyl­amino)­phen­yl]ethen­yl}-1-methyl­pyridinium 2,4,6-trimethyl­benzene­sulfonate monohydrate

Li, Y.; Zhang, J.-X.; Fu, P.-Z.; Wu, Y.-C.

doi:10.1107/S1600536811007690

Volume 67
Part 4
Page o823
April 2011

Received 25 January 2011
Accepted 1 March 2011
Online 9 March 2011

Key indicators
Single-crystal X-ray study
T = 103 K
Mean (C-C) = 0.002 Å
R = 0.042
wR = 0.108
Data-to-parameter ratio = 17.3
Details

4-{2-[4-(Dimethylamino)phenyl]ethenyl}-1-methylpyridinium 2,4,6-trimethylbenzenesulfonate monohydrate

Yin Li,^a ⁺ Jian-Xiu Zhang,^a ^* Pei-Zhen Fu ^a and Yi-Cheng Wu ^a

^aKey Laboratory of Functional Crystal and Laser Technology, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, People's Republic of China
Correspondence e-mail: zjx@mail.ipc.ac.cn

In the crystal structure of the title organic salt, C₁₆H₁₉N₂⁺·C₉H₁₁O₃S^-·H₂O, the cations pack head-to-tail within a sheet and are aligned in opposite directions in neighboring sheets. The benzene ring of the anion makes an angle of 76.99 (6)° with the plane of the cationic chromophore. The cations are situated in the ab plane, whereas the benzene rings of the anions lie in the ac plane.

Related literature

For the crystal structure of solvent-free 2,4,6- trimethylbenzenesulfonate (DSTMS), see: Yang et al. (2007); Mutter et al. (2007). For the crystal structure of 4-N,N-dimethylamino-4'-N'-methylstilbazolium tosylate (DAST) and DAST·H₂O, see: Marder et al. (1989); Pan et al. (1996); Bryant et al. (1993). For the synthesis, see: Marder et al. (1994).

Experimental

Crystal data

C₁₆H₁₉N₂⁺·C₉H₁₁O₃S^-·H₂O
M_r = 456.59
Triclinic, $[P \overline 1]$
a = 8.1993 (17) Å
b = 9.669 (2) Å
c = 15.247 (3) Å
= 87.806 (7)°
= 75.805 (6)°
= 83.239 (5)°
V = 1163.7 (4) Å³
Z = 2
Mo K radiation
= 0.17 mm^-1
T = 103 K
0.50 × 0.40 × 0.20 mm

Data collection

Rigaku AFC10/Saturn724+ diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) T_min = 0.918, T_max = 0.966
11232 measured reflections
5240 independent reflections
4259 reflections with I > 2(I)
R_int = 0.022

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.108
S = 1.00
5240 reflections
303 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.70 e Å^-3
_min = -0.35 e Å^-3

Data collection: CrystalClear (Rigaku, 2008); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ATOMS (Dowty, 1998); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IM2263 ).

Acknowledgements

The authors thank Professor Kaibei Yu, State Key Laboratory of Explosion Science and Technology of Beijing Institute of Technology, for the data collection. This work was supported by the National Basic Research Project of China (No. 2010CB630701).

References

Bryant, G. L., Yakymyshyn, C. P. & Stewart, K. R. (1993). Acta Cryst. C49, 350-351.
Dowty, E. (1998). ATOMS. Shape Software, Kingsport, Tennessee, USA.
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Marder, S. R., Perry, J. W. & Schaefer, W. P. (1989). Science, 245, 626-628.
Marder, S. R., Perry, J. W. & Yakymyshyn, C. P. (1994). Chem. Mater. 6, 1137-1147.
Mutter, L., Brunner, F. D., Yang, Z., Jazbinsek, M. & Günter, P. (2007). J. Opt. Soc. 24, 2556-2561.
Pan, F., Wong, M. S., Bosshard, C. & Günter, P. (1996). Adv. Mater. 8, 592-595.
Rigaku (2008). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Yang, Z., Mutter, L., Ruiz, B., Aravazhi, S., Stillhart, M., Jazbinsek, M., Gramlich, V. & Günter, P. (2007). Adv. Funct. Mater. 17, 2018-2023.

organic compounds