Received 17 December 2008
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 -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-HO and C-HO interactions. The water molecule forms O-HO hydrogen bonds to the nitrate anion and C-H interactions are also observed.
For details of nonlinear optical materials, see, for example: Dittrich et al. (2003); Nogi et al. (2000); Oudar & LePerson (1975); Sato et al. (1999). For related structures, see, for example: Chantrapromma et al. (2006, 2007, 2008). For reference bond-length data, see: Allen et al. (1987).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); 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, 2003).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2569 ).
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.
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