(E)-4-[(4-Bromophenyl)iminomethyl]-2-methoxyphenol

In the crystal structure of the title compound, C14H12BrNO2, the dihedral angle between the rings is 37.87 (10)° and the molecule has an E conformation about the central C=N bond. In the crystal, molecules are connected by intermolecular O—H⋯N hydrogen bonds into zigzag chains running parallel to the b axis. The packing also features C—H⋯O interactions.

In the crystal structure of the title compound, C 14 H 12 BrNO 2 , the dihedral angle between the rings is 37.87 (10) and the molecule has an E conformation about the central C N bond. In the crystal, molecules are connected by intermolecular O-HÁ Á ÁN hydrogen bonds into zigzag chains running parallel to the b axis. The packing also features C-HÁ Á ÁO interactions.
The molecules are connected by intermolecular O-H···N hydrogen bonds, forming zigzag chains parallel to the b axis ( Fig. 2). The crystal structure is further stabilized by intermolecular C-H···O hydrogen bonds.

Experimental
To a stirring solution of the 4-hydroxy-3-methoxybenzaldehyde (0.2 mmol, in 5 ml of methanol) was added 4-bromoaniline (0.2 mmol) in 10 ml of methanol, and the mixture was stirred for 1 h in air at 323 K and was then left at room temperature for several days without disturbance yielding suitable crystals of (1) that subsequently were filtered off and washed with Et 2 O. Yield: 91%.

Refinement
All H atoms bonded to carbon atoms were positioned geometrically and treated as riding on their parent atoms. The methyl H atoms were allowed to rotate freely about the adjacent C-O bonds. The hydroxyl H atoms were found in difference Fourier maps and their coordinates were refined with a restraint on the O-H bond length 0.85 Å with σ of 0.01. All hydrogen atoms were refined with thermal displacement coefficients U iso (H) set to 1.5U eq (C, O) for methyl and hydroxyl groups and to 1.2Ueq(C) for the CH and CH 2 groups.

Figure 2
Packing of molecules in direction of a axis. Hydrogen bonds are drawn as dashed lines.  (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F 2 for refinement carried out on F and F 2 , respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement. The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.