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Volume 69 
Part 10 
Pages o1510-o1511  
October 2013  

Received 7 August 2013
Accepted 21 August 2013
Online 7 September 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.058
wR = 0.172
Data-to-parameter ratio = 10.3
Details
Open access

(E)-2-[4-(Diethylamino)styryl]-1-methylquinolinium 4-fluorobenzenesulfonate monohydrate

aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia,bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, PO Box 2457, Riyadh 11451, Saudi Arabia,cDepartment of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and dFaculty of Traditional Thai Medicine, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
Correspondence e-mail: hkfun@usm.my

In the title hydrated molecular salt, C22H25N2+·C6H4FO3S-·H2O, the cation displays whole molecule disorder over two sets of sites in a 0.780 (5):0.220 (5) ratio. The quinolinium ring system is essentially planar, with r.m.s. deviations of 0.0162 and 0.0381 Å for the major and minor disorder components, respectively. The dihedral angles between the mean plane of the quinolinium ring system and the benzene ring are 5.1 (3) and 7.7 (11)°, respectively, for the major and minor components in the cation. In the crystal, cations, anions and water molecules are linked into chains along [010] by O-H...O hydrogen bonds and are further connected into a three-dimensional network by weak C-H...O and C-H...F interactions. In addition, [pi]-[pi] interactions with centroid-centroid distances of 3.634 (3), 3.702 (5) and 3.838 (5) Å are observed.

Related literature

For background to and applications of quarternary ammonium compounds, see: Babalola (1998[Babalola, G. O. (1998). Lett. Appl. Microbiol. 26, 43-46.]); Collier et al. (1953[Collier, H. O. J., Potter, M. D. & Taylor, E. P. (1953). Br. J. Pharmacol. 8, 34-37.]); Gutsulyak (1972[Gutsulyak, B. M. (1972). Russ. Chem. Rev. 41, 187-202.]); Chanawanno et al. (2010a[Chanawanno, K., Chantrapromma, S., Anantapong, T. & Kanjana-Opas, A. (2010a). Lat. Am. J. Pharm. 29, 1166-1170.],b[Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010b). Eur. J. Med. Chem. 45, 4199-4208.]). For related structures, see: Fun et al. (2010[Fun, H.-K., Chanawanno, K., Kobkeatthawin, T. & Chantrapromma, S. (2010). Acta Cryst. E66, o938-o939.], 2011[Fun, H.-K., Kaewmanee, N., Chanawanno, K. & Chantrapromma, S. (2011). Acta Cryst. E67, o593-o594.]); Kaewmanee et al. (2010[Kaewmanee, N., Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o2639-o2640.]). For standard bond lengths, 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. 1-S19.]). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C22H25N2+·C6H4FO3S-·H2O

  • Mr = 510.62

  • Monoclinic, P 21 /c

  • a = 13.366 (2) Å

  • b = 10.2326 (17) Å

  • c = 19.891 (3) Å

  • [beta] = 113.004 (8)°

  • V = 2504.1 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 100 K

  • 0.29 × 0.18 × 0.10 mm

Data collection
  • Bruker SMART APEXII DUO CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.951, Tmax = 0.982

  • 13569 measured reflections

  • 4396 independent reflections

  • 3379 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.058

  • wR(F2) = 0.172

  • S = 1.04

  • 4396 reflections

  • 427 parameters

  • 761 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.74 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1W-H1W1...O1 0.94 1.95 2.872 (4) 168
O1W-H2W1...O2i 0.90 2.09 2.909 (4) 151
C20A-H20B...F1ii 0.97 2.50 3.471 (6) 179
C25-H25A...O1Wiii 0.93 2.43 3.341 (4) 167
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x, y+{\script{3\over 2}}, -z+{\script{3\over 2}}]; (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, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5643 ).


Acknowledgements

The authors thank Prince of Songkla University for a research grant and extend their appreciation to the Deanship of Scientific Research at King Saud University and Universiti Sains Malaysia for the 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. 1-S19.
Babalola, G. O. (1998). Lett. Appl. Microbiol. 26, 43-46.  [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Wisconsin, USA.
Chanawanno, K., Chantrapromma, S., Anantapong, T. & Kanjana-Opas, A. (2010a). Lat. Am. J. Pharm. 29, 1166-1170.  [ChemPort]
Chanawanno, K., Chantrapromma, S., Anantapong, T., Kanjana-Opas, A. & Fun, H.-K. (2010b). Eur. J. Med. Chem. 45, 4199-4208.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Collier, H. O. J., Potter, M. D. & Taylor, E. P. (1953). Br. J. Pharmacol. 8, 34-37.  [ChemPort]
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [Web of Science] [IUCr Journals]
Fun, H.-K., Chanawanno, K., Kobkeatthawin, T. & Chantrapromma, S. (2010). Acta Cryst. E66, o938-o939.  [CrossRef] [ChemPort] [IUCr Journals]
Fun, H.-K., Kaewmanee, N., Chanawanno, K. & Chantrapromma, S. (2011). Acta Cryst. E67, o593-o594.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Gutsulyak, B. M. (1972). Russ. Chem. Rev. 41, 187-202.  [CrossRef]
Kaewmanee, N., Chanawanno, K., Chantrapromma, S. & Fun, H.-K. (2010). Acta Cryst. E66, o2639-o2640.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1510-o1511   [ doi:10.1107/S1600536813023532 ]

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