Received 18 March 2013
In the molecule of the title compound, C25H24FN, the dihedral angle between the best planes of the quinoline fragment (rings A and B) and the benzene ring (C) is 9.51 (4)°. In the crystal, molecules are linked into centrosymmetric dimers via pairs of weak C-HF interactions. The molecules are stacked into chains along the a axis by weak off-set - interactions between the A and C rings of translation-related molecules with a centroid-centroid distance of 3.6440 (2) Å.
For the preparation and spectroscopic properties of the title compound, see: Kozubková et al. (2012). For related structures, see: Kozubková et al. (2012); Prabhuswamy et al. (2012). For the biological activity of related compounds, see: Nayyar et al. (2009).
Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED; 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., 2008); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FY2093 ).
The financial support of this work by the Internal Founding Agency of Tomas Bata University in Zlin (project No. IGA/FT/2013/008) is gratefully acknowledged.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Kozubková, Z., Rouchal, M., Necas, M. & Vícha, R. (2012). Helv. Chim. Acta, 95, 1003-1017.
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.
Nayyar, A., Patel, S. R., Shaikh, M., Coutinho, E. & Jain, R. (2009). Eur. J. Med. Chem. 44, 2017-2029.
Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.
Prabhuswamy, M., Swaroop, T. R., Madan Kumar, S., Rangappa, K. S. & Lokanath, N. K. (2012). Acta Cryst. E68, o3250.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.