Received 4 December 2013
In the title Schiff base molecule, C13H9ClFNO, the benzene rings are twisted slightly with respect to each other, making a dihedral angle of 7.92 (2)°. An intramolecular O-HN hydrogen bond occurs. In the crystal, an infinite chain is formed along the c-axis direction by - stacking interactions between the phenyl rings and the six-membered hydrogen-bonded ring of neighboring Schiff base ligands [centroid-centroid distances of 3.698 (2) and 3.660 (3) Å]. Neighboring chains are linked into a three-dimensional supramolecular structure by C-HO and C-HF hydrogen bonds.
For the coordination modes of Schiff base ligands with transition metals, see: Ebrahimipour et al. (2012); Guo et al. (2013). For the biological activity of Schiff base ligands, see: Sawada et al. (2001); Ma et al. (2013); Siddiqui et al. (2006).
Data collection: CrysAlis PRO (Agilent, 2011); 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: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2572 ).
The author acknowledges Lanzhou Jiaotong University for supporting this work.
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