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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 [sigma](C-C) = 0.003 Å
R = 0.024
wR = 0.064
Data-to-parameter ratio = 18.2
Details
Open access

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

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-H...O 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[Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.]); Galal et al. (2009[Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.]); Khan et al. (2005[Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.]). For natural products with benzofuran rings, see: Akgul & Anil (2003[Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.]); Soekamto et al. (2003[Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.]). For the crystal structures of related compounds, see: Choi et al. (2009a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o563.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o726.]).

[Scheme 1]

Experimental

Crystal data
  • C13H13BrO3S

  • Mr = 329.20

  • Triclinic, [P \overline 1]

  • a = 7.4689 (3) Å

  • b = 9.9449 (4) Å

  • c = 10.0653 (4) Å

  • [alpha] = 98.415 (2)°

  • [beta] = 102.146 (2)°

  • [gamma] = 110.341 (3)°

  • V = 665.38 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.510, Tmax = 0.738

  • 11869 measured reflections

  • 3082 independent reflections

  • 2731 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2-C7 ring.

D-H...A D-H H...A D...A D-H...A
O2-H2O...O3i 0.74 (3) 1.90 (3) 2.640 (2) 177 (3)
C9-H9B...Cg2ii 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[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2. SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.  [ISI] [CrossRef] [PubMed] [ChemPort]
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.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o726.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.  [CrossRef] [PubMed] [ChemPort]
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o58  [ doi:10.1107/S1600536811052160 ]

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