Received 28 November 2013
The title compound, C18H23N2O2+·Cl-, crystallizes with two independent cations and anions per cell. Each cation has twofold rotational disorder about the linking vinyl groups but with unequal occupancies [0.963 (5):0.037 (5) and 0.860 (8):0.140 (8)]. The two independent cations are close to being related by an inversion centre but the data does not support the expected centrosymmetric space-group assignment. The conclusion is that the differing rotational disorder has lead to an overall non-centrosymmetric lattice. In the crystal, the molecules pack in layers parallel to (133) and (-13-3), chain-linked with motif C12(7) by the dihydroxypropyl O-HClH-O hydrogen bonds. Other lattice binding is provided by O-HCl, C-HCl and C-HN interactions.
For applications of organic push-pull chromophores, see: Kay et al. (2004); Bass et al. (2001); Prasad et al. (1988). For a related example of rotational disorder, see: Moreno-Fuquen et al. (2009). For details of the synthesis, see: Kay et al. (2001). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2012 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009) and Mercury.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5376 ).
This work was supported by the New Zealand Foundation for Science and Innovation grant (contract C08X0704). We thank Dr C. Fitchett of the University of Canterbury, New Zealand, for the data collection.
Bass, M., Enoch, J. M., Stryland, E. W. V. & Wolfe, W. L. (2001). In Handbook of Optics IV: Fibre Optics and Nonlinear Optics. New York: Academic Press.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Kay, A. J., Woolhouse, A. D., Gainsford, G. J., Haskell, T. G., Barnes, T. H., McKinnie, I. T. & Wyss, C. P. (2001). J. Mater. Chem. 11, 996-1002.
Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 14, 1321-1330.
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.
Moreno-Fuquen, R., Dvries, R., Theodoro, J. & Ellena, J. (2009). Acta Cryst. E65, o1371.
Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.
Prasad, P. N. & Ulrich, D. R. (1988). In Nonlinear Optical and Electro active Polymers. New York: Plenum.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.