Received 20 July 2013
The title compound, C21H13N3O, crystallizes with two independent molecules with similar conformations per asymmetric unit. The dihydrofuran rings are essentially planar with maximum deviations of 0.017 (1) and 0.006 (1) Å for the O atoms. The dihedral angles between the dihydrofuran ring and the attached phenyl rings are 79.90 (6) and 82.07 (6)° in one molecule and 79.36 (6) and 72.26 (6)° in the other. In the crystal, the molecules are linked by weak C-H and C-HN interactions similar to those in other closely related crystals. The replacement of appended methyl by phenyl groups has not significantly affected the dihydrofuran ring structure or the crystal packing interactions.
For general background to NLO chromophores, see: Smith et al. (2006, 2010); Carey et al. (2002); Kay et al. (2004). For details of the synthesis, see: Anderson (2009). For related structures, see: Anderson (2009); Gainsford et al. (2011); Li et al. (2005); Liao et al. (2005). For geometric analysis of structures, see: Spek (2009). For a description of the Cambridge Structural Database, see: Allen (2002).
Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5081 ).
This work was supported by a New Zealand Foundation for Research Science and Technology grant (contract No. C08X0704). We thank Dr C. Fitchett of the University of Canterbury, New Zealand, for his assistance.
Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Anderson, J. (2009). BSc (Hons.) project report. Victoria University of Wellington, New Zealand.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Carey, J. J., Bailey, R. T., Pugh, D., Sherwood, J. N., Cruikshank, F. R. & Wynne, K. (2002). Appl. Phys. Lett. 81, 4335-4337.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gainsford, G. J., Anderson, J., Bhuiyan, M. D. H. & Kay, A. J. (2011). Acta Cryst. E67, o3046-o3047.
Kay, A. J., Woolhouse, A. D., Zhao, Y. & Clays, K. (2004). J. Mater. Chem. 14, 1321-1330.
Li, S.-Y., Song, Y.-Y., You, Z.-L., Wen, Y.-W. & Qin, J.-G. (2005). Acta Cryst. E61, o2093-o2095.
Liao, Y., Eichinger, B. E., Firestone, K. A., Haller, M., Luo, J., Kaminsky, W., Benedict, J. B., Reid, P. J., Jen, A. K.-Y., Dalton, L. R. & Robinson, B. H. (2005). J. Am. Chem. Soc. 127, 2758-2766.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G. J., Dunford, C. L., Kay, A. J. & Woolhouse, A. D. (2006). J. Photochem. Photobiol. A, 179, 237-242.
Smith, G. J., Middleton, A. P., Clarke, D. J., Teshome, A., Kay, A. J., Bhuiyan, M. D. H., Asselberghs, I. & Clay, K. (2010). Opt. Mater. 32, 1237-1243.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.