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Volume 69 
Part 7 
Page o1135  
July 2013  

Received 12 June 2013
Accepted 17 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.029
wR = 0.075
Data-to-parameter ratio = 18.3
Details
Open access

5-Bromo-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, C21H14BrFO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 1.50 (8) and 81.47 (6)°, respectively. In the crystal, molecules are linked by weak C-H...O hydrogen bonds into supramolecular chains running along the a-axis direction. A short S...O contact [2.9623 (13) Å] involving the sulfinyl groups is observed between inversion-related chains.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2609.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.]). For details of sulfinyl-sulfinyl interactions, see: Choi et al. (2008[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1061.]). For a review of carbonyl-carbonyl interactions, see: Allen et al. (1998[Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.]).

[Scheme 1]

Experimental

Crystal data
  • C21H14BrFO2S

  • Mr = 429.29

  • Triclinic, [P \overline 1]

  • a = 7.9961 (2) Å

  • b = 10.6641 (2) Å

  • c = 11.1695 (2) Å

  • [alpha] = 71.980 (1)°

  • [beta] = 74.694 (1)°

  • [gamma] = 79.964 (1)°

  • V = 869.13 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.51 mm-1

  • T = 173 K

  • 0.30 × 0.24 × 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 = 0.523, Tmax = 0.665

  • 20230 measured reflections

  • 4315 independent reflections

  • 3839 reflections with I > 2[sigma](I)

  • Rint = 0.042

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.075

  • S = 1.05

  • 4315 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20...O2i 0.95 2.33 3.280 (3) 176
Symmetry code: (i) 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 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: XU5714 ).


Acknowledgements

This work was supported by a Dong-eui University grant (2013AA075).

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.  [Web of Science] [CrossRef] [IUCr Journals]
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., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1061.  [CSD] [CrossRef] [IUCr Journals]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2609.  [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, o1135  [ doi:10.1107/S1600536813016760 ]

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