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Volume 67 
Part 7 
Page o1689  
July 2011  

Received 30 May 2011
Accepted 2 June 2011
Online 18 June 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.045
wR = 0.119
Data-to-parameter ratio = 15.4
Details
Open access

3-Cyclopentylsulfonyl-5-fluoro-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

There are two independent molecules, A and B, in the asymmetric unit of the title compound, C14H15FO3S, in each of which the cyclopentyl ring adopts an envelope conformation. The benzofuran units in each molecule are essentially planar, with mean deviations from the least-squares plane defined by the nine constituent ring atoms of 0.009 (2) Å for molecule A and 0.013 (2) Å for molecule B. In the crystal, molecules are linked by weak C-H...O hydrogen bonds. In the cyclopentyl ring of molecule B, one C atom is disordered over two positions with site-occupancy factors of 0.60 (2) and 0.40 (2).

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 a structural study of the related compound 5-bromo-3-cyclopentylsulfinyl-2-methyl-1-benzofuran, see: Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1386.]).

[Scheme 1]

Experimental

Crystal data
  • C14H15FO3S

  • Mr = 282.32

  • Triclinic, [P \overline 1]

  • a = 10.0568 (8) Å

  • b = 10.2697 (8) Å

  • c = 13.2894 (10) Å

  • [alpha] = 95.033 (4)°

  • [beta] = 109.140 (4)°

  • [gamma] = 91.229 (4)°

  • V = 1289.82 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 173 K

  • 0.26 × 0.24 × 0.20 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 = 0.936, Tmax = 0.948

  • 21777 measured reflections

  • 5565 independent reflections

  • 4022 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.119

  • S = 1.03

  • 5565 reflections

  • 361 parameters

  • 20 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9C...O6i 0.98 2.45 3.348 (3) 152
C19-H19...O6ii 0.95 2.58 3.469 (3) 157
C23-H23A...O2iii 0.98 2.50 3.318 (3) 141
Symmetry codes: (i) x-1, y-1, z; (ii) x-1, y, z; (iii) x+1, y, 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: GO2016 ).


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.
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]
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1386.  [CrossRef] [details]
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 (2011). E67, o1689  [ doi:10.1107/S1600536811021222 ]

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