3-(4-Fluoro­phenyl­sulfin­yl)-5-iodo-2-methyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536810024931

Volume 66
Part 7
Page o1876
July 2010

Received 10 May 2010
Accepted 25 June 2010
Online 30 June 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.029
wR = 0.077
Data-to-parameter ratio = 18.1
Details

3-(4-Fluorophenylsulfinyl)-5-iodo-2-methyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^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 4-fluorophenyl group of the 4-fluorophenylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment; the 4-fluorophenyl ring is nearly perpendicular to this plane, making a dihedral angle of 83.37 (7)°. The crystal structure is stabilized by weak intermolecular C-HO hydrogen bonds and an IO interaction [IO = 3.255 (2) Å]. The crystal structure also exhibits intermolecular C-F [pi] interactions [3.068 (2) Å], and aromatic [pi] - [pi] interactions between the furan and benzene rings of neighbouring benzofuran fragments [centroid-centroid distance = 3.636 (2) Å].

Related literature

For the crystal structures of similar 3-(4-fluorophenylsulfinyl)-2-methyl-1-benzofuran derivatives, see: Choi et al. (2010a,b,c). For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental

Crystal data

C₁₅H₁₀FIO₂S
M_r = 400.19
Monoclinic, P 2₁ /c
a = 13.1665 (4) Å
b = 11.4338 (4) Å
c = 9.9296 (3) Å
= 107.181 (1)°
V = 1428.13 (8) Å³
Z = 4
Mo K radiation
= 2.40 mm^-1
T = 173 K
0.27 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.565, T_max = 0.648
12825 measured reflections
3297 independent reflections
2990 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.077
S = 1.11
3297 reflections
182 parameters
H-atom parameters constrained
_max = 0.58 e Å^-3
_min = -1.56 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O1ⁱ	0.93	2.55	3.472 (3)	170
C9-H9CO2ⁱⁱ	0.96	2.53	3.277 (3)	135
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: CS2129 ).

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.
Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.
Brandenburg, K. (1998). DIAMOND. Crystal Impact GmbH, Bonn, Germany.
Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o472.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o543.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010c). Acta Cryst. E66, o564.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model., 13, 305-311.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.

organic compounds