4-Fluoro-2-[(3-methylphenyl)iminomethyl]phenol

The title compound, C14H12FNO, crystallizes as the trans phenol–imine tautomer. The two benzene rings are essentially coplanar, being inclined to one another by 9.28 (7)°. This is at least in part due to the intramolecular O—H⋯N hydrogen bond between the hydroxy O atom and the imine N atom. The crystal structure is stabilized by an array of weak C—H⋯O and C—H⋯F interactions, which link the molecules into a stable three-dimensional network.

The title compound, C 14 H 12 FNO, crystallizes as the trans phenol-imine tautomer. The two benzene rings are essentially coplanar, being inclined to one another by 9.28 (7) . This is at least in part due to the intramolecular O-HÁ Á ÁN hydrogen bond between the hydroxy O atom and the imine N atom. The crystal structure is stabilized by an array of weak C-HÁ Á ÁO and C-HÁ Á ÁF interactions, which link the molecules into a stable three-dimensional network.
The compound crystallizes as the trans phenol-imine tautomer. A strong intramolecular hydrogen bond occurs between the O-H···N atoms in each unique molecule. The crystal structure is stabilized by an array of weak C-H···O and C-H···F interactions. The bifurcated acceptor, O1, experiences weak hydrogen bond interactions with H16 and H1A. As a result, the two independent molecules pack nearly perpendicular to each other with a dihedral angle of 88.01 (5)° between planes drawn through the C1 aromatic ring systems (Figures 2 and 3). All the interactions serve to link the molecules into a stable three-dimensional supramolecular network. The molecular packing, viewed along the c-axis, illustrates the cube-like tunnel formation resulting from the various interactions ( Figure 4).

Experimental
The reaction was performed under Schlenk conditions using a nitrogen atmosphere. To a solution of 5-fluorosalicylaldehyde (0.50 g, 3.57 mmol) in methanol, a solution of m-toluidine (0.382 g, 3.57 mmol) was added. The reaction was refluxed at 80°C for 3 h. The solvent was removed under reduced pressure. The product was obtained as an orange solid which was washed with cold methanol and filtered. Crystals suitable for X-ray diffraction were grown from the filtrate.

Refinement
The aromatic H atoms and hydroxy H atom were placed in geometrically idealized positions and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C) and 1.5 eq (O).The aliphatic H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with U iso (H) = 1.2U eq (C) and 1.5 eq (C), respectively for the methylene and methyl carbon atoms. The methyl groups were generated to fit the difference electron density and the groups were then refined as rigid rotors. The absolute structure parameter is meaningless and has been removed from the CIF.
The Friedel opposites have been merged as the compound is a weak anomalous scatterer.

Figure 1
Representation of the molecular structure of the title compound, showing the numbering scheme and displacement ellipsoids drawn at the 50% probability level.

Special details
Experimental. Intensity data was collected on a Bruker X8 Apex II 4 K Kappa CCD diffractometer using an exposure time of 55 s/frame. A total of 1495 frames were collected with a frame width of 0.5° covering up to θ = 28.0° with 99.6% completeness accomplished Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq N1 0.51676 (