3-Ethyl­sulfinyl-2-(4-fluoro­phen­yl)-5,6-methyl­enedi­oxy-1-benzofuran

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

doi:10.1107/S160053681001617X

Volume 66
Part 6
Page o1296
June 2010

Received 20 April 2010
Accepted 3 May 2010
Online 8 May 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 15.3
Details

3-Ethylsulfinyl-2-(4-fluorophenyl)-5,6-methylenedioxy-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, C₁₇H₁₃FO₄S, the 4-fluorophenyl ring makes a dihedral angle of 4.92 (4)° with the plane of the 5,6-methylenedioxy-1-benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C-HO and C-HF hydrogen bonds.

Related literature

For the crystal structures of similar 2-aryl-5,6-methylenedioxy-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007, 2010). 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).

Experimental

Crystal data

C₁₇H₁₃FO₄S
M_r = 332.33
Triclinic, $[P \overline 1]$
a = 7.1081 (9) Å
b = 9.631 (1) Å
c = 10.708 (1) Å
= 93.201 (2)°
= 95.510 (2)°
= 105.423 (2)°
V = 700.85 (13) Å³
Z = 2
Mo K radiation
= 0.26 mm^-1
T = 173 K
0.40 × 0.36 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.610, T_max = 0.746
6872 measured reflections
3194 independent reflections
2955 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.093
S = 1.03
3194 reflections
209 parameters
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C12-H12O4ⁱ	0.93	2.62	3.380 (2)	140
C16-H16AFⁱⁱ	0.97	2.56	3.2090 (17)	125
C17-H17BO4ⁱⁱⁱ	0.96	2.61	3.469 (2)	149
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y, z+1; (iii) x+1, y, z.

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: FL2302 ).

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). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Lee, H. K., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o519-o520.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o605.
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