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Volume 65 
Part 9 
Page o2115  
September 2009  

Received 22 July 2009
Accepted 4 August 2009
Online 8 August 2009

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.004 Å
R = 0.022
wR = 0.055
Data-to-parameter ratio = 16.2
Details
Open access

5-Fluoro-2-(4-iodophenyl)-3-methylsulfinyl-1-benzofuran

aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
Correspondence e-mail: uklee@pknu.ac.kr

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-H...O hydrogen bond and an I...O halogen bond [3.055 (2) Å]. The crystal structure also exhibits an intermolecular C-H...[pi] interaction between the methyl H atom and the 4-iodophenyl ring of an adjacent benzofuran molecule, and aromatic [pi]-[pi] interactions between the benzene rings of neighbouring benzofuran systems [centroid-centroid distance = 3.558 (3) Å].

Related literature

For the crystal structures of similar 2-(4-iodophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2008a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o1061.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o1088.]). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999[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.]); Twyman & Allsop (1999[Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.]). For a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data
  • C15H10FIO2S

  • Mr = 400.19

  • Triclinic, [P \overline 1]

  • a = 8.8989 (5) Å

  • b = 9.2370 (5) Å

  • c = 10.3357 (5) Å

  • [alpha] = 105.579 (1)°

  • [beta] = 115.302 (1)°

  • [gamma] = 101.671 (1)°

  • V = 689.08 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.48 mm-1

  • T = 273 K

  • 0.25 × 0.15 × 0.10 mm

Data collection
  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.])) Tmin = 0.650, Tmax = 0.784

  • 5972 measured reflections

  • 2957 independent reflections

  • 2689 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.022

  • wR(F2) = 0.055

  • S = 1.09

  • 2957 reflections

  • 182 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.68 e Å-3

  • [Delta][rho]min = -0.55 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C15-H15C...O2i 0.96 2.42 3.238 (3) 143
C15-H15B...Cg3ii 0.96 2.91 3.554 (3) 126
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+1, -z. Cg3 is the centroid of the C9-C14 benzene ring.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: VM2001 ).


References

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.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o1088.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
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.  [CrossRef] [PubMed] [ChemPort]
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2009). E65, o2115  [ doi:10.1107/S1600536809030992 ]

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