(E)-2-[(4-Iodophenyl)iminomethyl]-6-methylphenol

The title compound, C14H12INO, adopts the phenol–imine tautomeric form. The dihedral angle between the aromatic rings is 20.6 (3)°. The molecular conformation is stabilized by an intramolecular O—H⋯N hydrogen bond while in the crystal, weak intermolecular C—H⋯O hydrogen bonds link the molecules into a zigzag chain parallel to the b axis.


Structure Reports Online
The molecular structure of the title compound, C 14 H 17 O 1 N 1 I 1, shows that the molecule exists in the phenol-imine form This conformation is stabilized by intramolecular N-H···O hydrogen bond (Table 1, Fig. 1) forming S(6) ring (Bernstein et al., 1995). weak intermolecular C-H···O hydrogen bonds link the molecules forming a zig-zag chain parallel to the b axis (Table 1, Fig. 2). The I atom is slightly out of the C9-C14 ring by 0.18 (1)Å.

Refinement
The position of the H1 atom was obtained from a difference map of the electron density in the unit-cell and was refined freely.
Other H atoms were positioned geometrically and treated using a riding model, fixing the bond lengths at 0.93 Å for aromatic CH and at 0.96 Å for CH 3 . The displacement parameters of the H atoms were constrained as U iso (H)= 1.2U eq (1.5U eq for methyl) of the parent atom. Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme and 30% probability displacement ellipsoids. H atoms are represented as small spheres of arbitrary radii. H bond is shown as dashed lines.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 Rfactors(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.