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Volume 70 
Part 1 
Pages o11-o12  
January 2014  

Received 22 November 2013
Accepted 29 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.065
wR = 0.154
Data-to-parameter ratio = 12.7
Details
Open access

2-[(E)-2-(4-Eth­oxy­phen­yl)ethen­yl]-1-methyl­quinolinium 4-fluoro­benzene­sulfonate

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

In the structure of the title salt, C20H20NO+·C6H4FO3S-, the 4-(eth­oxy­phen­yl)ethenyl unit is disordered over two positions with a refined site-occupancy ratio of 0.610 (6):0.390 (6). The cation is nearly planar, the dihedral angle between the quinolinium and benzene rings being 6.7 (4) and 1.7 (7)° for the major and minor components, respectively. The eth­oxy group is essentially coplanar with the benzene ring [C-O-C-Cmethy = 177.1 (8) and 177.8 (12)° for the major and minor components, respectively]. In the crystal, cations and anions are linked into chains along the b-axis direction by C-H...Osulfon­yl weak inter­actions. These chains are further connected into sheets parallel to (001) by C-H...Osulfon­yl weak inter­actions. The chains are also stacked along the a axis through [pi]-[pi] inter­actions involving the quinolinium and benzene rings [centroid-centroid distances = 3.636 (5) Å for the major component and 3.800 (9) Å for the minor component]. C-H...[pi] inter­actions are also present.

Related literature

For background to the bioactivity and non-linear optical properties of quinolinium derivatives, 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.]); Hopkins et al. (2005[Hopkins, K. L., Davies, R. H. & Threfall, E. J. (2005). Int. J. Antimicrob. Agents, 25, 358-373.]); Musiol et al. (2006[Musiol, R., Jampilek, J., Buchta, V., Silva, L., Halina, H., Podeszwa, B., Palka, A., Majerz-Maniecka, K., Oleksyn, B. & Polanski, J. (2006). Bioorg. Med. Chem. 14, 3592-3598.]); O'Donnell et al. (2010[O'Donnell, F., Smyth, T. J. P., Ramachandran, V. N. & Smyth, W. F. (2010). Int. J. Antimicrob. Agents, 35, 30-38.]); Ruanwas et al. (2010[Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padakid, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.]). For related structures, see: Chantrapromma et al. (2011[Chantrapromma, S., Chanawanno, K. & Fun, H.-K. (2011). Acta Cryst. E67, o515-o516.]); Fun et al. (2010[Fun, H.-K., Chanawanno, K., Kobkeatthawin, T. & Chantrapromma, S. (2010). Acta Cryst. E66, o938-o939.]); Ruanwas et al. (2010[Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padakid, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.]). 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.]). 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
  • C20H20NO+·C6H4FO3S-

  • Mr = 465.52

  • Monoclinic, P 21 /n

  • a = 6.4366 (3) Å

  • b = 9.8909 (5) Å

  • c = 34.3628 (15) Å

  • [beta] = 95.102 (2)°

  • V = 2179.00 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 100 K

  • 0.37 × 0.12 × 0.05 mm

Data collection
  • Bruker 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 = 0.932, Tmax = 0.991

  • 19050 measured reflections

  • 4993 independent reflections

  • 3609 reflections with I > 2[sigma](I)

  • Rint = 0.060

Refinement
  • R[F2 > 2[sigma](F2)] = 0.065

  • wR(F2) = 0.154

  • S = 1.09

  • 4993 reflections

  • 392 parameters

  • 418 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.39 e Å-3

  • [Delta][rho]min = -0.49 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 and Cg5 are the centroids of the C12B-C17B and C21-C26 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C2-H2A...O2i 0.93 2.55 3.456 (4) 166
C8-H8A...O4ii 0.93 2.41 3.306 (3) 161
C10-H10A...O3 0.96 2.55 3.483 (4) 164
C11A-H11A...O4ii 0.93 2.52 3.408 (19) 159
C17A-H17A...O3 0.93 2.58 3.510 (10) 177
C20-H20B...O2i 0.96 2.53 3.441 (4) 158
C20-H20C...O3 0.96 2.44 3.085 (4) 124
C25-H25A...O4iii 0.93 2.55 3.264 (4) 134
C13A-H13A...Cg5ii 0.93 2.82 3.575 (10) 139
C16A-H16A...Cg5 0.93 2.98 3.826 (9) 151
C19A-H19B...Cg4iii 0.96 2.99 3.862 (11) 152
C13B-H13B...Cg5ii 0.93 2.95 3.765 (16) 147
C16B-H16B...Cg5 0.93 2.70 3.562 (13) 155
Symmetry codes: (i) x+1, y, z; (ii) x, y-1, z; (iii) x-1, y, 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.]), Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]) 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: RZ5097 ).


Acknowledgements

The authors thank Prince of Songkla University for a research grant. They also thank the 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. S1-19.  [CrossRef]
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.  [Web of Science] [CSD] [CrossRef] [ChemPort] [PubMed]
Chantrapromma, S., Chanawanno, K. & Fun, H.-K. (2011). Acta Cryst. E67, o515-o516.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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]
Hopkins, K. L., Davies, R. H. & Threfall, E. J. (2005). Int. J. Antimicrob. Agents, 25, 358-373.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Musiol, R., Jampilek, J., Buchta, V., Silva, L., Halina, H., Podeszwa, B., Palka, A., Majerz-Maniecka, K., Oleksyn, B. & Polanski, J. (2006). Bioorg. Med. Chem. 14, 3592-3598.  [CrossRef] [PubMed] [ChemPort]
O'Donnell, F., Smyth, T. J. P., Ramachandran, V. N. & Smyth, W. F. (2010). Int. J. Antimicrob. Agents, 35, 30-38.  [Web of Science] [PubMed] [ChemPort]
Ruanwas, P., Kobkeatthawin, T., Chantrapromma, S., Fun, H.-K., Philip, R., Smijesh, N., Padakid, M. & Isloor, A. M. (2010). Synth. Met. 160, 819-824.  [Web of Science] [CSD] [CrossRef] [ChemPort]
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 (2014). E70, o11-o12   [ doi:10.1107/S1600536813032509 ]

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