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Volume 65 
Part 2 
Pages o258-o259  
February 2009  

Received 17 December 2008
Accepted 1 January 2009
Online 8 January 2009

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Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.063
wR = 0.199
Data-to-parameter ratio = 12.1
Details
Open access

Bis{4-[(E)-2-(1H-indol-3-yl)ethenyl]-1-methylpyridinium} 4-fluorobenzenesulfonate nitrate 0.25-hydrate1

Suchada Chantraprommaa* and Hoong-Kun Funb+

aCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand, and bX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: suchada.c@psu.ac.th

In the title compound, 2C16H15N2+·C6H4FO3S-·NO3-·0.25H2O, the two cations are nearly planar, with dihedral angles of 1.34 (14) and 4.6 (2)°, respectively, between the pyridinium and indole rings. The cations each adopt E configurations with respect to the C=C bonds and are inclined to each other with a dihedral angle of 77.66 (5)°. The ethenyl group of one cation is disordered over two sites with occupancies of 0.685 (12) and 0.315 (12), and the sulfonate group of the 4-fluorobenzenesulfonate anion is also disordered with occupancies of 0.535 (10) and 0.465 (10) for the two sets of O atoms. The anion is also inclined to the two cations, with dihedral angles between the mean planes of the benzene ring and the [pi]-conjugated systems of the cations of 24.72 (11) and 79.83 (11)°. In the crystal structure, the cations are stacked in an antiparallel fashion into columns approximately along the a axis and are further linked through the anions into a three-dimensional network via N-H...O and C-H...O interactions. The water molecule forms O-H...O hydrogen bonds to the nitrate anion and C-H...[pi] interactions are also observed.

Related literature

For details of nonlinear optical materials, see, for example: Dittrich et al. (2003[Dittrich, Ph., Bartlome, R., Montemezzani, G. & Günter, P. (2003). Appl. Surf. Sci. 220, 88-95.]); Nogi et al. (2000[Nogi, K., Anwar, U., Tsuji, K., Duan, X.-M., Okada, S., Oikawa, H., Matsuda, H. & Nakanishi, H. (2000). Nonlinear Opt. 24, 35-40.]); Oudar & LePerson (1975[Oudar, J. L. & LePerson, H. (1975). Opt. Commun. 15, 258-262.]); Sato et al. (1999[Sato, N., Rikukawa, M., Sanui, K. & Ogata, N. (1999). Synth. Met. 101, 132-133.]). For related structures, see, for example: Chantrapromma et al. (2006[Chantrapromma, S., Jindawong, B., Fun, H.-K., Patil, P. S. & Karalai, C. (2006). Acta Cryst. E62, o1802-o1804.], 2007[Chantrapromma, S., Jindawong, B., Fun, H.-K., Patil, P. S. & Karalai, C. (2007). Anal. Sci. 23, x27-x28.], 2008[Chantrapromma, S., Kobkeatthawin, T., Chanawanno, K., Karalai, C. & Fun, H.-K. (2008). Acta Cryst. E64, o876-o877.]). For reference 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

  • 2C16H15N2+·C6H4FO3S-·NO3-·0.25H2O

  • Mr = 712.27

  • Triclinic, [P \overline 1]

  • a = 8.7750 (6) Å

  • b = 13.6366 (1) Å

  • c = 15.3190 (11) Å

  • [alpha] = 97.520 (1)°

  • [beta] = 91.236 (1)°

  • [gamma] = 99.861 (1)°

  • V = 1788.66 (18) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.15 mm-1

  • T = 297 (2) K

  • 0.57 × 0.39 × 0.12 mm
Data collection

  • Siemens SMART CCD area-detector diffractometer

  • Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.919, Tmax = 0.982

  • 17243 measured reflections

  • 6287 independent reflections

  • 4818 reflections with I > 2[sigma](I)

  • Rint = 0.018
Refinement

  • R[F2 > 2[sigma](F2)] = 0.063

  • wR(F2) = 0.199

  • S = 1.03

  • 6287 reflections

  • 520 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.46 e Å-3

  • [Delta][rho]min = -0.25 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the rings N4/C30-C32/C37, C32-C37 and C16-C21, respectively.
D-H...A D-H H...A D...A D-H...A
N2-H1N2...O3Ai 0.86 2.09 2.950 (10) 175
N4-H1N4...O4ii 0.86 2.36 3.106 (4) 145
N4-H1N4...O5ii 0.86 2.43 3.259 (6) 163
O1W-H1W1...O5iii 0.85 2.42 2.711 (14) 101
C6-H6A...O2A 0.93 2.44 2.866 (7) 108
C7-H7A...O4iv 0.93 2.51 3.224 (4) 134
C9-H9A...O1Av 0.93 2.47 3.169 (8) 132
C22-H22A...O1Av 0.96 2.39 3.256 (8) 149
C22-H22C...O2Avi 0.96 2.19 3.147 (8) 175
C23-H23A...O6vii 0.93 2.55 3.456 (5) 164
C15-H15A...Cg1viii 0.93 2.99 3.896 (3) 164
C15-H15A...Cg2viii 0.93 2.72 3.563 (4) 151
C34-H34A...Cg3ix 0.93 2.78 3.595 (4) 147
C38-H38C...Cg2x 0.96 2.95 3.695 (4) 135
Symmetry codes: (i) x, y-1, z; (ii) x-1, y, z; (iii) x, y, z-1; (iv) -x+2, -y+1, -z+1; (v) -x+2, -y+2, -z+1; (vi) x+1, y, z; (vii) -x+1, -y+1, -z+2; (viii) -x+1, -y+1, -z+1; (ix) -x, -y+1, -z+1; (x) -x, -y+2, -z+2.

Data collection: SMART (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Siemens, 1996[Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments 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, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2569 ).

Acknowledgements

The authors thank the Prince of Songkla University for financial support and the Universiti Sains Malaysia for 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.
Chantrapromma, S., Jindawong, B., Fun, H.-K., Patil, P. S. & Karalai, C. (2006). Acta Cryst. E62, o1802-o1804.  [CrossRef] [details]
Chantrapromma, S., Jindawong, B., Fun, H.-K., Patil, P. S. & Karalai, C. (2007). Anal. Sci. 23, x27-x28.  [CSD] [CrossRef] [ChemPort]
Chantrapromma, S., Kobkeatthawin, T., Chanawanno, K., Karalai, C. & Fun, H.-K. (2008). Acta Cryst. E64, o876-o877.  [CSD] [CrossRef] [details]
Dittrich, Ph., Bartlome, R., Montemezzani, G. & Günter, P. (2003). Appl. Surf. Sci. 220, 88-95.  [ISI] [CrossRef] [ChemPort]
Nogi, K., Anwar, U., Tsuji, K., Duan, X.-M., Okada, S., Oikawa, H., Matsuda, H. & Nakanishi, H. (2000). Nonlinear Opt. 24, 35-40.  [ChemPort]
Oudar, J. L. & LePerson, H. (1975). Opt. Commun. 15, 258-262.  [CrossRef] [ChemPort] [ISI]
Sato, N., Rikukawa, M., Sanui, K. & Ogata, N. (1999). Synth. Met. 101, 132-133.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2009). E65, o258-o259   [ doi:10.1107/S1600536809000026 ]

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