5-Bromo-3-ethyl­sulfinyl-2-(4-fluoro­phenyl)-1-benzofuran

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

doi:10.1107/S1600536810000590

Volume 66
Part 2
Page o323
February 2010

Received 4 January 2010
Accepted 6 January 2010
Online 9 January 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.024
wR = 0.068
Data-to-parameter ratio = 16.9
Details

5-Bromo-3-ethylsulfinyl-2-(4-fluorophenyl)-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, C₁₆H₁₂BrFO₂S, the 4-fluorophenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 5.94 (5)°. The crystal structure exhibits aromatic [pi] - [pi] interactions between the benzene ring and the 4-fluorophenyl ring of an adjacent molecule [centroid-centroid distance = 3.632 (2) Å], and a BrO halogen bond with a BrO distance of 3.101 (1) Å.

Related literature

For the crystal structures of similar 2-(4-fluorophenyl)-5-halo-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009, 2010a,b). For the biological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Howlett et al. (1999). 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

C₁₆H₁₂BrFO₂S
M_r = 367.23
Triclinic, $[P \overline 1]$
a = 7.2806 (5) Å
b = 9.4999 (6) Å
c = 10.8334 (6) Å
= 101.360 (3)°
= 98.783 (3)°
= 104.771 (3)°
V = 693.87 (8) Å³
Z = 2
Mo K radiation
= 3.12 mm^-1
T = 100 K
0.30 × 0.26 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.457, T_max = 0.606
12298 measured reflections
3202 independent reflections
3040 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.068
S = 1.01
3202 reflections
190 parameters
H-atom parameters constrained
_max = 0.48 e Å^-3
_min = -0.47 e Å^-3

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: SI2236 ).

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 GbR, Bonn, Germany.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2608.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o44.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o104.
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.
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. (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