1-Methyl-4-[(1E,3E)-4-phenyl­buta-1,3-dien­yl]pyridinium iodide monohydrateThis paper is dedicated to His Majesty King Bhumibol Adulyadej of Thailand (King Rama IX) for his sustainable development of the country.

Fun, H.-K.; Chanawanno, K.; Surasit, C.; Chantrapromma, S.

doi:10.1107/S1600536810006045

Volume 66
Part 3
Pages o651-o652
March 2010

Received 14 February 2010
Accepted 15 February 2010
Online 20 February 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.007 Å
Disorder in solvent or counterion
R = 0.046
wR = 0.117
Data-to-parameter ratio = 26.0
Details

1-Methyl-4-[(1E,3E)-4-phenylbuta-1,3-dienyl]pyridinium iodide monohydrate¹

Hoong-Kun Fun,^a ^*⁺ Kullapa Chanawanno,^b Chanasuk Surasit ^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

The asymmetric unit of the title compound, C₁₆H₁₆N⁺·I^-·H₂O, contains two 1-methyl-4-{[(1E,3E)-4-phenylbuta-1,3-dienyl]}pyridinium cations, two iodide ions and two solvent water molecules. The cation is twisted slightly, the dihedral angle between the pyridinium and the phenyl rings being 10.68 (18)° in one molecule and 18.9 (3)° in the other. The two water molecules are disordered over three positions with site-occupancy ratio of 0.9/0.7/0.4. In the crystal packing, the cations are arranged into ribbons along the b axis with the iodide ions and water molecules located between adjacent cations. The cations are linked to the iodide ions and water molecules by weak C-HI and C-HO interactions, respectively. These interactions together with O-HI hydrogen bonds link the molecules into a two-dimensional network parallel to the bc plane. [pi] [pi] interactions with a centroid-centroid distance of 3.669 (2) Å are also observed.

Related literature

For bond-length data, see: Allen et al. (1987). For background to non-linear optical materials research, see: Raimundo et al. (2002). For related structures, see: Chantrapromma et al. (2009a,b), Fun et al. (2009). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986).

Experimental

Crystal data

C₁₆H₁₆N⁺·I^-·H₂O
M_r = 367.21
Monoclinic, C 2/c
a = 32.5600 (6) Å
b = 12.6414 (2) Å
c = 16.5602 (3) Å
= 111.180 (1)°
V = 6355.81 (19) Å³
Z = 16
Mo K radiation
= 2.01 mm^-1
T = 100 K
0.55 × 0.20 × 0.20 mm

Data collection

Bruker APEXII CCD area detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.407, T_max = 0.694
36570 measured reflections
9279 independent reflections
6818 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.117
S = 1.02
9279 reflections
357 parameters
H-atom parameters constrained
_max = 2.40 e Å^-3
_min = -1.87 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2W-H2W2I1Aⁱ	0.79	2.88	3.655 (8)	166
C3B-H3BO1Wⁱⁱ	0.93	2.51	3.399 (8)	161
C16A-H16AI1Aⁱⁱⁱ	0.96	3.05	3.992 (4)	167
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) x, y, z-1; (iii) -x+1, -y+1, -z+1.

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: SJ2731 ).

Acknowledgements

KC thanks the Development and Promotion of Science and Technology Talents Project (DPST) for a study grant. The authors thank Prince of Songkla University for financial support and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012.

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.
Chantrapromma, S., Chanawanno, K. & Fun, H.-K. (2009a). Acta Cryst. E65, o1144-o1145.
Chantrapromma, S., Chanawanno, K. & Fun, H.-K. (2009b). Acta Cryst. E65, o3115-o3116.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Fun, H.-K., Surasit, C., Chanawanno, K. & Chantrapromma, S. (2009). Acta Cryst. E65, o2633-o2634.
Raimundo, J.-M., Blanchard, P., Planas, N. G., Mercier, N., Rak, I. L., Hierle, R. & Roncali, J. (2002). J. Org. Chem. 67, 205-218.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.