2-[(2-Chlorophenyl)iminomethyl]-4,6-diiodophenol

The asymmetric unit of the title compound, C13H8ClI2NO, contains half of the molecule situated on a mirror plane. The hydroxy group is involved in the formation of an intramolecular O—H⋯N hydrogen bond. π–π interactions between the benzene rings of neighbouring molecules [centroid–centroid distance = 3.629 (3) Å] form stacks along the b axis. In the crystal, weak C—H⋯O and C—H⋯Cl interactions are observed.

The asymmetric unit of the title compound, C 13 H 8 ClI 2 NO, contains half of the molecule situated on a mirror plane. The hydroxy group is involved in the formation of an intramolecular O-HÁ Á ÁN hydrogen bond.interactions between the benzene rings of neighbouring molecules [centroid-centroid distance = 3.629 (3) Å ] form stacks along the b axis. In the crystal, weak C-HÁ Á ÁO and C-HÁ Á ÁCl interactions are observed.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5247).  (Table 1). Bond distances are within normal values (Allen et al., 1987), and are comparable with those reported in the literature for related compounds (Weiser et al., 2006;Barba et al., 2009;Francis et al., 2003).
The mixture was stirred at room temperature for 30 min to give a yellow solution. Yellow block-shaped single crystals were obtained by slow evaporation of the solution containing the compound in air.

Refinement
C-bound H atoms were positioned geometrically and allowed to ride on their parent atoms, with C-H = 0.93 Å and U iso = 1.2 U eq (C). Atom H1 was located on a difference map and isotropically refined.

Computing details
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008  The molecular structure of the title compound, showing the atom labelling scheme. The displacement ellipsoids are drawn at the 30% probability level. Intramolecular hydrogen bond is indicated by a dashed line. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 1.13 e Å −3 Δρ min = −0.76 e Å −3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.0030 (6) 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.