Received 30 April 2013
aDepartment of Pure & Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow G1 1XL, Scotland,bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey,cChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England,dChemistry Department, Faculty of Sccience, Mini University, 61519 El-Minia, Egypt, and eAnalytical Sciences, Manchester Metropolitan University, Manchester, M1 5GD, England
Correspondence e-mail: firstname.lastname@example.org
The title molecule, C17H11FN2O3, is nearly planar [maximum deviation = 0.197 (1) Å] and the molecular conformation is stabilized by an N-HO hydrogen bond forming an S(6) ring motif. The H atom of the intramolecular hydrogen bond was found to be disordered over two sites and thus both the hydroxy and keto tautomers are simultaneously present in the solid. Refinement of the occupancy of this site suggests that the hydroxy form is the major component [occupancy refined to 0.59 (3):0.41 (3)]. Bond lengths are also largely consistent with dominance of the hydroxy form. In the crystal, molecules are linked by C-HO hydrogen bonds, forming layers parallel to (101). - stacking interactions [centroid-centroid distances = 3.5649 (9) and 3.7579 (9) Å] inter-connect these layers.
For the broad range of biological applications of Schiff bases, see, for example: Cozzi (2004); Chandra & Sangeetika (2004); Sari et al. (2003); Verma et al. (2004). For the significance of fluorine atoms in drug structures, see: Blair et al. (2000); Kirk et al. (1979); LeBars et al. (1987). For a related structure, see: Akkurt et al. (2012). For hydrogen-bond motifs, see: Bernstein et al. (1995).
Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5319 ).
The University of Strathclyde, Erciyes University and Manchester Metropolitan University are gratefully acknowledged for supporting this study.
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