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Volume 66 
Part 6 
Page o1296  
June 2010  

Received 20 April 2010
Accepted 3 May 2010
Online 8 May 2010

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 15.3
Details
Open access

3-Ethylsulfinyl-2-(4-fluorophenyl)-5,6-methylenedioxy-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, C17H13FO4S, the 4-fluorophenyl ring makes a dihedral angle of 4.92 (4)° with the plane of the 5,6-methylenedioxy-1-benzofuran fragment. In the crystal, molecules are linked by weak intermolecular C-H...O and C-H...F hydrogen bonds.

Related literature

For the crystal structures of similar 2-aryl-5,6-methylenedioxy-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2007[Choi, H. D., Seo, P. J., Lee, H. K., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o519-o520.], 2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o605.]). For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006[Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C17H13FO4S

  • Mr = 332.33

  • Triclinic, [P \overline 1]

  • a = 7.1081 (9) Å

  • b = 9.631 (1) Å

  • c = 10.708 (1) Å

  • [alpha] = 93.201 (2)°

  • [beta] = 95.510 (2)°

  • [gamma] = 105.423 (2)°

  • V = 700.85 (13) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 173 K

  • 0.40 × 0.36 × 0.28 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 = 0.610, Tmax = 0.746

  • 6872 measured reflections

  • 3194 independent reflections

  • 2955 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.093

  • S = 1.03

  • 3194 reflections

  • 209 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C12-H12...O4i 0.93 2.62 3.380 (2) 140
C16-H16A...Fii 0.97 2.56 3.2090 (17) 125
C17-H17B...O4iii 0.96 2.61 3.469 (2) 149
Symmetry codes: (i) -x, -y, -z+1; (ii) x, y, z+1; (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: FL2302 ).


References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.  [ISI] [CrossRef] [PubMed] [ChemPort]
Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.  [ISI] [CrossRef] [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., Lee, H. K., Son, B. W. & Lee, U. (2007). Acta Cryst. E63, o519-o520.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o605.  [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 (2010). E66, o1296  [ doi:10.1107/S160053681001617X ]

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