[Journal logo]

Volume 69 
Part 7 
Page o1187  
July 2013  

Received 13 June 2013
Accepted 26 June 2013
Online 29 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.123
Data-to-parameter ratio = 18.1
Details
Open access

5-Fluoro-2-(4-fluorophenyl)-7-methyl-3-phenylsulfinyl-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, C21H14F2O2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (2) Å] of the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 5.93 (9) and 80.23 (5)°, respectively. In the crystal, molecules are linked by weak C-H...O and 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. (2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o498.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1237.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.]).

[Scheme 1]

Experimental

Crystal data
  • C21H14F2O2S

  • Mr = 368.38

  • Monoclinic, P 21 /n

  • a = 12.3698 (8) Å

  • b = 7.9967 (5) Å

  • c = 17.4195 (10) Å

  • [beta] = 100.323 (4)°

  • V = 1695.20 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.22 mm-1

  • T = 173 K

  • 0.30 × 0.26 × 0.10 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 = 0.655, Tmax = 0.746

  • 30145 measured reflections

  • 4267 independent reflections

  • 3147 reflections with I > 2[sigma](I)

  • Rint = 0.065

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.123

  • S = 1.04

  • 4267 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C16-C21 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C20-H20...O2i 0.95 2.35 3.252 (3) 158
C9-H9B...Cg1ii 0.98 2.79 3.519 (2) 132
Symmetry codes: (i) x, y-1, z; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\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: GG2118 ).


Acknowledgements

This work was supported by a Dong-eui University grant (No. 2013AA076).

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, U. (2012). Acta Cryst. E68, o1237.  [CSD] [CrossRef] [IUCr Journals]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o498.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1187  [ doi:10.1107/S1600536813017583 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.