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Volume 68 
Part 1 
Page o205  
January 2012  

Received 14 December 2011
Accepted 15 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.097
Data-to-parameter ratio = 20.5
Details
Open access

3-(4-Bromophenylsulfinyl)-5-cyclohexyl-2-methyl-1-benzofuran

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, C21H21BrO2S, the cyclohexyl ring adopts a chair conformation. The 4-bromophenyl ring makes a dihedral angle of 81.62 (6)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked by weak C-H...O and C-H...[pi] interactions. The crystal structure also exhibits a slipped [pi]-[pi] interaction between the furan rings of neighbouring molecules [centroid-centroid distances = 3.540 (3) Å, interplanar distance = 3.481 (3) Å and slippage = 0.644 (3) Å].

Related literature

For the biological 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. (2011a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o768.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o1157.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21BrO2S

  • Mr = 417.35

  • Monoclinic, P 21 /c

  • a = 16.7340 (4) Å

  • b = 8.8290 (2) Å

  • c = 13.0178 (3) Å

  • [beta] = 105.197 (1)°

  • V = 1856.05 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.34 mm-1

  • T = 173 K

  • 0.25 × 0.23 × 0.11 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 = 0.561, Tmax = 0.746

  • 17836 measured reflections

  • 4653 independent reflections

  • 3467 reflections with I > 2[sigma](I)

  • Rint = 0.039

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.04

  • 4653 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.52 e Å-3

  • [Delta][rho]min = -0.61 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2-C7 benzene ring.

D-H...A D-H H...A D...A D-H...A
C17-H17...O2i 0.95 2.47 3.112 (3) 125
C15-H15B...Cg2ii 0.98 3.06 3.532 (3) 111
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) -x, -y+1, -z+1.

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: FF2048 ).


Acknowledgements

This work was supported by Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

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. (2011a). Acta Cryst. E67, o768.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o1157.  [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, o205  [ doi:10.1107/S1600536811054158 ]

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