Methyl 4-iodosalicylate

Structure

2-hy­droxy-4-iodo­benzoic acid methyl ester (methyl 4-iodo­salicylate, C8H7IO3) allows for an effective way of incorporating the methyl salicylates within larger organic mol­ecules, using such methodologies as McClure protocols, which take advantage of the iodine atom at the 4-position of the aromatic ring for the formation of carbon-carbon bonds. The iodine atom is also capable of forming supra­molecular synthons, which may be useful for crystal engineering. At 90 K, the methyl 4-iodo­salicylat displays monoclinic (P21/c) symmetry with one mol­ecule in the asymmetric unit. Inter­molecular hydrogen bonding inter­actions occur between the hy­droxy groups of one mol­ecule and the carbonyl oxygen atom of the methyl ester of an adjacent mol­ecule to form a centrosymmetric dimeric pair with H⋯O = 2.53 (4) Å. An O3—H3⋯O2 intra­molecular hydrogen bond also exists with an H⋯O distance of 2.05 (4) Å. The C5⋯C8 [3.326 (3) Å] and O3⋯H1C (2.51 Å) inter­actions provide only short contacts between the stacks of offset (102) parallel sheets, which make up the crystal. These sheets, in turn, contain the inversion-generated hydrogen-bonded dimers. The non-hydrogen atoms of the mol­ecule are essentially coplanar with no displacement from the mean mol­ecular plane greater than 0.132 Å.