Received 22 July 2009
In the title compound, C15H10FIO2S, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane through the benzofuran fragment. The 4-iodophenyl ring is rotated out of the benzofuran plane by a dihedral angle of 39.4 (1)°. The crystal structure is stabilized by an intermolecular C-HO hydrogen bond and an IO halogen bond [3.055 (2) Å]. The crystal structure also exhibits an intermolecular C-H interaction between the methyl H atom and the 4-iodophenyl ring of an adjacent benzofuran molecule, and aromatic - interactions between the benzene rings of neighbouring benzofuran systems [centroid-centroid distance = 3.558 (3) Å].
For the crystal structures of similar 2-(4-iodophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2008a,b). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999). For a review of halogen bonding, see: Politzer et al. (2007).
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: VM2001 ).
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o1061.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o1088.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.