1-Methyl-2-[(E)-2,4,5-trimeth­oxy­styr­yl]pyridinium 4-meth­oxy­benzene­sulfonate monohydrate

Fun, H.-K.; Mueangkeaw, C.; Ruanwas, P.; Chantrapromma, S.

doi:10.1107/S1600536811008610

Volume 67
Part 4
Pages o867-o868
April 2011

Received 22 February 2011
Accepted 7 March 2011
Online 12 March 2011

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.045
wR = 0.124
Data-to-parameter ratio = 16.3
Details

1-Methyl-2-[(E)-2,4,5-trimethoxystyryl]pyridinium 4-methoxybenzenesulfonate monohydrate

Hoong-Kun Fun,^a ^*⁺ Charoensak Mueangkeaw,^b Pumsak Ruanwas ^b and Suchada Chantrapromma ^b ⁺⁺

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

In the title compound, C₁₇H₂₀NO₃⁺·C₇H₇O₄S^-·H₂O, the cation exists in an E configuration with respect to the C=C bond and is twisted with a dihedral angle of 17.81 (8)° between the pyridinium and benzene rings. The benzene ring of the anion is almost parallel to the pyridinium ring [dihedral angle = 3.45 (9)°], whereas it is inclined to the benzene ring of the cation [dihedral angle = 17.62 (8)°]. The crystal structure is stabilized by O-HO hydrogen bonds and weak C-HO interactions which link the cations, anions and water molecules into chains along the a axis. [pi] - [pi] interactions with centroid-centroid distances of 3.7751 (9) and 3.7920 (11) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987). For background to the non-linear optical properties and applications of pyridinium and quinolinium derivatives, see: Chanawanno et al. (2010), Chantrapromma et al. (2010); Fun et al. (2009); Ruanwas et al. (2010); Williams (1984). For related structures, see, Chantrapromma et al. (2007); Mueangkeaw et al. (2010). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental

Crystal data

C₁₇H₂₀NO₃⁺·C₇H₇O₄S^-·H₂O
M_r = 491.55
Triclinic, $[P \overline 1]$
a = 6.8463 (4) Å
b = 10.8855 (5) Å
c = 15.8137 (8) Å
= 83.950 (2)°
= 81.355 (2)°
= 81.140 (2)°
V = 1147.14 (10) Å³
Z = 2
Mo K radiation
= 0.19 mm^-1
T = 100 K
0.40 × 0.08 × 0.06 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.927, T_max = 0.989
20386 measured reflections
5219 independent reflections
4534 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.124
S = 1.05
5219 reflections
320 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.54 e Å^-3
_min = -0.56 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1W-H2W1O6	0.80 (3)	2.08 (3)	2.8703 (19)	175 (3)
O1W-H1W1O5ⁱ	0.85 (3)	1.98 (3)	2.8233 (19)	173 (2)
C9-H9AO4	0.93	2.53	3.445 (2)	167
C14-H14AO1Wⁱⁱ	0.96	2.32	3.262 (2)	168
C14-H14CO1ⁱⁱⁱ	0.96	2.54	3.487 (2)	168
C16-H16AO7^iv	0.96	2.53	3.388 (2)	149
C16-H16BO5ⁱⁱⁱ	0.96	2.54	3.408 (2)	150
C16-H16CO6^v	0.96	2.44	3.371 (2)	163
C17-H17CO4ⁱⁱⁱ	0.96	2.47	3.419 (2)	168
C18-H18AO1W^vi	0.93	2.43	3.354 (2)	171
C22-H22AO2^iv	0.93	2.36	3.281 (2)	170
Symmetry codes: (i) x-1, y, z; (ii) x+1, y-1, z; (iii) -x+2, -y, -z+1; (iv) -x+1, -y+1, -z+1; (v) -x+1, -y, -z+1; (vi) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2563 ).

Acknowledgements

CM thanks the Development and Promotion of Science and Technology Talents Project (DPST) for a study grant. Financial support from the Prince of Songkla University is acknowledged. The authors also thank Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199-4208.
Chantrapromma, S., Chanawanno, K. & Fun, H.-K. (2010). Acta Cryst. E66, o1975-o1976.
Chantrapromma, S., Jindawong, B., Fun, H.-K. & Patil, P. S. (2007). Anal. Sci. 23, x81-x82.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Fun, H.-K., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o1934-o1935.
Mueangkeaw, C., Chantrapromma, S., Ruanwas, P. & Fun, H.-K. (2010). Acta Cryst. E66, o3098-o3099.
Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padaki, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Williams, D. J. (1984). Angew. Chem. Int. Ed. Engl. 23, 690-703.

organic compounds