3-(4-Fluoro­phenyl­sulfon­yl)-5-iodo-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S1600536811052792

Volume 68
Part 1
Page o96
January 2012

Received 6 December 2011
Accepted 7 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.022
wR = 0.057
Data-to-parameter ratio = 18.8
Details

3-(4-Fluorophenylsulfonyl)-5-iodo-2,7-dimethyl-1-benzofuran

Pil Ja Seo,^a Hong Dae Choi,^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, C₁₆H₁₂FIO₃S, the 4-fluorophenyl ring makes a dihedral angle of 72.31 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C-HO hydrogen bonds, and by an II contact [3.7764 (3) Å]. The crystal structure also exhibits a weak C-I [pi] [3.901 (3) Å] interaction and a slipped [pi] - [pi] interaction between the furan and benzene rings of neighbouring molecules [centroid-centroid distance = 3.845 (3), interplanar distance = 3.555 (3) and slippage = 1.465 (3) Å].

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For related structures, see: Choi et al. (2008, 2011).

Experimental

Crystal data

C₁₆H₁₂FIO₃S
M_r = 430.22
Triclinic, $[P \overline 1]$
a = 7.5839 (2) Å
b = 10.2443 (3) Å
c = 10.4651 (3) Å
= 79.424 (1)°
= 75.652 (1)°
= 80.361 (1)°
V = 767.94 (4) Å³
Z = 2
Mo K radiation
= 2.24 mm^-1
T = 173 K
0.32 × 0.30 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.534, T_max = 0.689
13962 measured reflections
3785 independent reflections
3585 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.022
wR(F²) = 0.057
S = 1.08
3785 reflections
201 parameters
H-atom parameters constrained
_max = 0.47 e Å^-3
_min = -0.72 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O3ⁱ	0.95	2.54	3.253 (2)	132
C15-H15O2ⁱⁱ	0.95	2.52	3.294 (3)	139
Symmetry codes: (i) -x, -y, -z+2; (ii) -x+1, -y, -z+1.

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: BH2405 ).

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, 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. (2008). Acta Cryst. E64, o930.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1082.
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.
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