2-(3-Ethyl­sulfanyl-5-fluoro-1-benzofuran-2-yl)acetic acid

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

doi:10.1107/S160053680903671X

Volume 65
Part 10
Page o2482
October 2009

Received 8 September 2009
Accepted 11 September 2009
Online 16 September 2009

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.005 Å
R = 0.047
wR = 0.113
Data-to-parameter ratio = 16.0
Details

2-(3-Ethylsulfanyl-5-fluoro-1-benzofuran-2-yl)acetic acid

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

The title compound, C₁₂H₁₁FO₃S, was prepared by alkaline hydrolysis of ethyl 2-(3-ethylsulfanyl-5-fluoro-1-benzofuran-2-yl) acetate. In the crystal structure, the carboxyl groups are involved in intermolecular O-HO hydrogen bonds, which link the molecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by aromatic [pi] - [pi] interactions between the furan ring and the benzene ring of neighbouring benzofuran ring systems [centroid-centroid distance = 3.684 (5) Å].

Related literature

For the crystal structures of similar 2-(5-halo-1-benzofuran-2-yl) acetic acid derivatives, see: Choi et al. (2009a,b). For the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999).

Experimental

Crystal data

C₁₂H₁₁FO₃S
M_r = 254.27
Monoclinic, P 2₁ /n
a = 10.6009 (9) Å
b = 8.3319 (7) Å
c = 13.395 (1) Å
= 96.138 (1)°
V = 1176.34 (17) Å³
Z = 4
Mo K radiation
= 0.28 mm^-1
T = 173 K
0.25 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) T_min = 0.931, T_max = 0.958
9646 measured reflections
2543 independent reflections
1541 reflections with I > 2(I)
R_int = 0.072

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.113
S = 1.16
2543 reflections
159 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.28 e Å^-3
_min = -0.33 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O2-H2O3ⁱ	0.85 (5)	1.81 (5)	2.654 (3)	177 (5)
Symmetry code: (i) -x+2, -y, -z+1.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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: ZQ2007 ).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o563.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1813.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.

organic compounds