2-(4-Chloro­phen­yl)-5-fluoro-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536810001157

Volume 66
Part 2
Page o364
February 2010

Received 4 January 2010
Accepted 10 January 2010
Online 16 January 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.088
Data-to-parameter ratio = 16.6
Details

2-(4-Chlorophenyl)-5-fluoro-3-methylsulfinyl-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, C₁₅H₁₀ClFO₂S, the O atom and the methyl group of the methylsulfinyl substituent are located on opposite sides of the plane through the benzofuran fragment. The 4-chlorophenyl ring is rotated out of the benzofuran plane, as indicated by the dihedral angle of 21.04 (4)°. The crystal structure exhibits a weak intermolecular C-HO hydrogen bond and a ClO halogen bond [ClO = 3.254 (1) Å].

Related literature

For the crystal structures of similar 5-fluoro-2-(4-halophenyl)-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2009a,b,c). For the biological properties 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

C₁₅H₁₀ClFO₂S
M_r = 308.74
Triclinic, $[P \overline 1]$
a = 7.7088 (5) Å
b = 8.5241 (5) Å
c = 11.6369 (7) Å
= 74.572 (3)°
= 70.893 (3)°
= 67.109 (3)°
V = 657.13 (7) Å³
Z = 2
Mo K radiation
= 0.46 mm^-1
T = 100 K
0.25 × 0.22 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.895, T_max = 0.942
10607 measured reflections
3020 independent reflections
2629 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.088
S = 1.03
3020 reflections
182 parameters
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.27 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C10-H10O2ⁱ	0.93	2.52	3.347 (2)	148
Symmetry code: (i) -x, -y+1, -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: VM2017 ).

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. (2009a). Acta Cryst. E65, o2084.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o2115.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009c). Acta Cryst. E65, o2608.
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