2-[(3-Bromophenyl)iminomethyl]phenol

The title compound, C13H10BrNO, was prepared by reaction of 3-bromoaniline with 2-hydroxybenzaldehyde at 377 K. The molecular structure and packing are stabilized by an intramolecular O—H⋯N hydrogen-bond interaction.


2-[(3-Bromophenyl)iminomethyl]phenol
Xiao-Yan Ren and Fang-Fang Jian S1. Comment The recent growing interest in Schiff bases is also due to their ability to form intramolecular hydrogen bonds by electron coupling between acid-base centers (Rozwadowski et al., 1999). The part of our research is to find Schiff base with higher biological activity, we synthesized the title compound (I) and report its crystal structure here.

S2. Experimental
A mixture of 2-nitrobenzaldehyde (0.02 mol) and 4-methoxyaniline (0.02 mol) was stirred with ethanol (50 mL) at 377 K for 5 h, affording the title compound (4.33 g, yield 84.5%). Single crystals suitable for X-ray measurements were obtained by recrystallization from acetone at room temperature.

S3. Refinement
H atoms were positioned geometrically and allowed to ride on their parent atoms, with O-H and C-H distances of 0.82 and 0.93 Å, respectively, and with U iso (H) = 1.2 or 1.5U eq of the parent atoms.  The molecular structure of the title compound with the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.

Figure 2
A view of the packing and the intramolecular hydrogen bonding (dashed lines) of (I) in the unitcell.

Special details
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. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.