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Volume 69 
Part 5 
Page o721  
May 2013  

Received 1 April 2013
Accepted 9 April 2013
Online 13 April 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 18.2
Details
Open access

2-(2-Fluorophenyl)-3-methylsulfanyl-5-phenyl-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, C21H15FOS, the dihedral angles between the mean plane [r.m.s. deviation = 0.041 (1) Å] of the benzofuran fragment and the pendant 2-fluorophenyl and phenyl rings are 46.09 (3) and 24.34 (5)°, respectively. In the crystal, molecules are linked by weak C-H...[pi] interactions, forming a three-dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2006[Choi, H. D., Seo, P. J., Kang, B. W., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o4796-o4797.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3006.]).

[Scheme 1]

Experimental

Crystal data
  • C21H15FOS

  • Mr = 334.39

  • Monoclinic, P 21 /n

  • a = 11.1257 (2) Å

  • b = 7.4232 (1) Å

  • c = 19.4212 (3) Å

  • [beta] = 97.319 (1)°

  • V = 1590.90 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 173 K

  • 0.27 × 0.19 × 0.14 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.689, Tmax = 0.746

  • 28795 measured reflections

  • 3967 independent reflections

  • 3190 reflections with I > 2[sigma](I)

  • Rint = 0.040

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

  • wR(F2) = 0.101

  • S = 1.05

  • 3967 reflections

  • 218 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.26 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the C9-C14 phenyl and 2-fluorophenyl rings, respectively.

D-H...A D-H H...A D...A D-H...A
C10-H10...Cg1i 0.95 2.82 3.682 (2) 131
C14-H14...Cg2ii 0.95 2.71 3.528 (2) 145
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+1, -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 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: DS2230 ).


Acknowledgements

This work was supported by the 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

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., Kang, B. W., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o4796-o4797.  [CSD] [CrossRef] [ChemPort] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3006.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o721  [ doi:10.1107/S1600536813009768 ]

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