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Volume 69 
Part 7 
Page o1093  
July 2013  

Received 3 June 2013
Accepted 7 June 2013
Online 12 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.046
wR = 0.128
Data-to-parameter ratio = 18.1
Details
Open access

3-Ethylsulfinyl-2-(3-fluorophenyl)-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, C22H17FO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran ring system and the pendant 3-fluorophenyl and phenyl rings are 23.92 (5) and 32.44 (5)°, respectively. In the crystal, molecules are linked by two weak C-H...O(sulfinyl) hydrogen bonds and a C-H...[pi] interaction, forming a sheet, which lies in the ab plane. A [pi]-[pi] interaction between the benzene and furan rings of neighbouring molecules [centroid-centroid distance = 3.976 (2) Å] links the molecules into inversion dimers and connects adjacent sheets, resulting in 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., Lee, H. K., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o4480-o4481.], 2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1167.]).

[Scheme 1]

Experimental

Crystal data
  • C22H17FO2S

  • Mr = 364.42

  • Monoclinic, P 21 /n

  • a = 12.6447 (3) Å

  • b = 7.1680 (2) Å

  • c = 19.2382 (5) Å

  • [beta] = 100.592 (2)°

  • V = 1713.99 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 173 K

  • 0.38 × 0.25 × 0.18 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 = 0.684, Tmax = 0.746

  • 16390 measured reflections

  • 4269 independent reflections

  • 3406 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.128

  • S = 1.04

  • 4269 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.85 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C9-C14 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C12-H12...O2i 0.95 2.49 3.166 (3) 128
C21-H21A...O2ii 0.99 2.58 3.367 (3) 136
C14-H14...Cg1iii 0.95 2.66 3.466 (3) 143
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

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, 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: GO2092 ).


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., Lee, H. K., Son, B. W. & Lee, U. (2006). Acta Cryst. E62, o4480-o4481.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1167.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1093  [ doi:10.1107/S1600536813015924 ]

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