2-(5-Bromo-3-isopropyl­sulfanyl-1-benzofuran-2-yl)acetic acid

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

doi:10.1107/S1600536811052160

Volume 68
Part 1
Page o58
January 2012

Received 3 November 2011
Accepted 3 December 2011
Online 10 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.024
wR = 0.064
Data-to-parameter ratio = 18.2
Details

2-(5-Bromo-3-isopropylsulfanyl-1-benzofuran-2-yl)acetic acid

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

The title compound, C₁₃H₁₃BrO₃S, was prepared by alkaline hydrolysis of ethyl 2-(5-bromo-3-isopropylsulfanyl-1-benzofuran-2-yl)acetate. In the crystal, the carboxyl groups are involved in intermolecular O-HO hydrogen bonds, which link the molecules into dimers. These dimers are further packed into stacks along the c axis by intermolecular C-H [pi] interactions, and by slipped [pi] - [pi] interactions between the furan rings of adjacent molecules [centroid-centroid distance = 3.472 (2) Å, interplanar distance = 3.398 (2) Å and slippage = 0.713 (2) Å].

Related literature

For the pharmacological 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 the crystal structures of related compounds, see: Choi et al. (2009a,b).

Experimental

Crystal data

C₁₃H₁₃BrO₃S
M_r = 329.20
Triclinic, $[P \overline 1]$
a = 7.4689 (3) Å
b = 9.9449 (4) Å
c = 10.0653 (4) Å
= 98.415 (2)°
= 102.146 (2)°
= 110.341 (3)°
V = 665.38 (5) Å³
Z = 2
Mo K radiation
= 3.24 mm^-1
T = 296 K
0.24 × 0.17 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.510, T_max = 0.738
11869 measured reflections
3082 independent reflections
2731 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.064
S = 1.03
3082 reflections
169 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.52 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2-C7 ring.

D-HA	D-H	HA	DA	D-HA
O2-H2OO3ⁱ	0.74 (3)	1.90 (3)	2.640 (2)	177 (3)
C9-H9BCg2ⁱⁱ	0.97	2.72 (1)	3.376 (2)	126
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+1, -y+1, -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: BG2430 ).

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. (2009a). Acta Cryst. E65, o563.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o726.
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