Received 18 April 2008
The title compound, C16H13IO3S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 76.31 (8)° with the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic - interactions between the furan and benzene rings of neighbouring molecules, and between the benzene rings of neighbouring molecules; the centroid-centroid distances within the stack are 3.700 (4) and 3.788 (4) Å. In addition, the crystal structure exhibits inter- and intramolecular C-HO interactions, and an IO halogen bond with an IO distance of 3.282 (2) Å and a nearly linear C-IO angle of 165.69 (8)°.
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZL2112 ).
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