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Volume 69 
Part 3 
Pages o458-o459  
March 2013  

Received 14 January 2013
Accepted 24 February 2013
Online 28 February 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
Disorder in main residue
R = 0.025
wR = 0.055
Data-to-parameter ratio = 34.1
Details
Open access

(E)-2-[4-(Diethylamino)styryl]-1-ethylpyridinium iodide monohydrate

aDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,bFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand,cX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and dDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia
Correspondence e-mail: suchada.c@psu.ac.th

In the title hydrated salt, C19H25N2+·I-·H2O, the 4-(diethylamino)phenyl unit of the cation is disordered over two positions in a 0.847 (3):0.153 (3) ratio. The cation is twisted, with dihedral angles between the pyridinium and benzene rings of 11.25 (13) and 10.7 (8)° for the major and minor components, respectively. In the crystal, the three components are linked into a centrosymmetric 2:2:2 unit by O-H...I and C-H...O hydrogen bonds. [pi]-[pi] interactions with centroid-centroid distances of 3.5065 (7)-3.790 (9) Å are also present.

Related literature

For background to and applications of aminostyrylpyridinium compounds, see: Chanawanno et al. (2010[Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010). Eur. J. Med. Chem. 45, 4199-4208.]); Larnbert et al. (1996[Larnbert, C., Mease, R. C., Amen, L., Le, T., Sabet, H. & McAfee, J. G. (1996). Nucl. Med. Biol., 23, 417-427.]). For related structures, see: Fun et al. (2011a[Fun, H.-K., Kaewmanee, N., Chanawanno, K. & Chantrapromma, S. (2011a). Acta Cryst. E67, o593-o594.],b[Fun, H.-K., Kaewmanee, N., Chanawanno, K., Karalai, C. & Chantrapromma, S. (2011b). Acta Cryst. E67, o2488-o2489.]); Kaewmanee et al. (2010[Kaewmanee, N., Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o2639-o2640.]). For bond-length data, see: Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C19H25N2+·I-·H2O

  • Mr = 426.33

  • Triclinic, [P \overline 1]

  • a = 7.9969 (1) Å

  • b = 9.1336 (1) Å

  • c = 14.7740 (2) Å

  • [alpha] = 96.220 (1)°

  • [beta] = 105.430 (1)°

  • [gamma] = 105.060 (1)°

  • V = 986.05 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.63 mm-1

  • T = 100 K

  • 0.26 × 0.23 × 0.13 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.677, Tmax = 0.816

  • 32289 measured reflections

  • 8664 independent reflections

  • 7821 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.055

  • S = 1.08

  • 8664 reflections

  • 254 parameters

  • 20 restraints

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

  • [Delta][rho]max = 0.78 e Å-3

  • [Delta][rho]min = -0.99 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1W...I1i 0.85 (3) 2.71 (2) 3.5498 (12) 176 (2)
O1W-H2W...I1ii 0.86 (3) 2.75 (3) 3.6055 (13) 171 (2)
C3-H3A...O1Wiii 0.95 2.35 3.2072 (19) 150
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5238 ).


Acknowledgements

SC, NB and NK thank Prince of Songkla University for a research grant. The authors also thank the Malaysian Government and Universiti Sains Malaysia for APEX DE2012 grant No. 1002/PFIZIK/910323.

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 (2009). 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.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Fun, H.-K., Kaewmanee, N., Chanawanno, K. & Chantrapromma, S. (2011a). Acta Cryst. E67, o593-o594.  [CSD] [CrossRef] [details]
Fun, H.-K., Kaewmanee, N., Chanawanno, K., Karalai, C. & Chantrapromma, S. (2011b). Acta Cryst. E67, o2488-o2489.  [CSD] [CrossRef] [details]
Kaewmanee, N., Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o2639-o2640.  [CSD] [CrossRef] [details]
Larnbert, C., Mease, R. C., Amen, L., Le, T., Sabet, H. & McAfee, J. G. (1996). Nucl. Med. Biol., 23, 417-427.  [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o458-o459   [ doi:10.1107/S160053681300528X ]

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