2-Bromo-4-chloro-6-(4-fluorophenyliminomethyl)phenol

The two molecules of the title compound, C13H8BrClFNO, in the asymmetric unit are interconnected by π–π interactions between the salicylaldehyde and aniline units, the shortest interplanar distance being 3.317 (3) Å. These pairs and their translation equivalents are further linked by C—H⋯F hydrogen bonds, forming a one-dimensional infinite chain. In addition, there is an intramolecular O—H⋯N hydrogen bond connecting the OH group and the imine N atom.

The two molecules of the title compound, C 13 H 8 BrClFNO, in the asymmetric unit are interconnected byinteractions between the salicylaldehyde and aniline units, the shortest interplanar distance being 3.317 (3) Å . These pairs and their translation equivalents are further linked by C-HÁ Á ÁF hydrogen bonds, forming a one-dimensional infinite chain. In addition, there is an intramolecular O-HÁ Á ÁN hydrogen bond connecting the OH group and the imine N atom.   Table 1 Hydrogen-bond geometry (Å , ).   et al., 2007;Prabhakaran et al., 2004). Among the prodigious number and variety of Schiff bases, salicylaldimines have been studied widely because of their synthetic proclivity and structural diversity (Collinson et al., 1996;Garnovski et al., 2002). In recent years, there has been considerable interest in the chemistry of transition metal complexes of Schiff bases. This is due to the fact that Schiff bases offer opportunities for inducing substrate chirality, tuning metal centered electronic properties, enhancing solubility and stability of either homogeneous or heterogeneous catalysts and producing antibacterial agents (Karvembu et al., 2003;Nakajima et al., 1998;Kumar et al., 2004;Ramesh et al., 2003;Kannan et al., 2006).

Related literature
With the above view, in our ongoing research, we have chosen the title compound as a specific and representative ligand to synthesize ruthenium complexes. The title compound and its complexes will be screened against the bacterei E. coli, S.aureous, P.mirabilis and P.vulgaris.
The title compound, C 9 H 8 BrClFNO, crystallizes in the triclinic space group P1 with one molecule in the asymmetric unit. Figure 1 shows the ORTEP representation of the molecule with thermal ellipsoids at the 50% probability level. The packing of the molecules in the unit cell showing the inter molecular interactions is depicted in Figure 2. The molecule and its inversion analogue are linked to each other by Π-Π interactions between the salicylaldehyde moiety and the aniline moiety with the shortest interplanar distance of 3.317 (3) Å (1 -x, 1 -y, 1 -z). The molecules are further connected by C11-H11···F1 hydrogen bonds (2.452 Å, 161.89°, 1 + x, -1 + y, 1 + z) forming an one-dimensional infinite chain. The packing is further stabilized by Van der Waals interactions. In addition, an intramolecular hydrogen bonding O1-H1···N1 (2.577 (3) Å, 145.9°) linking the OH group of the former salicyleldehyde and the imine N atom. The dihedral angle between the salicylaldehyde and aniline moieties is 8.8 (2)°.
The product was recrystallized from EtOH. The purity of the compound was checked by TLC.

Refinement
All the H atoms were located from the difference Fourier map. However, the aromatic H atoms were geometrically constrained at idealized positions (C-H = 0.93 Å) and were refined using a riding model with U iso equal to 1.2 times U eq of the parent carbon atom. The hydroxyl hydrogen was refined isotropically with restraint: O-H = 0.820 (1) Å. Fig. 1. The ORTEP representation of the molecule with thermal ellipsoids at the 50% probability level.