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Volume 68 
Part 12 
Page o3464  
December 2012  

Received 7 November 2012
Accepted 14 November 2012
Online 28 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.028
wR = 0.075
Data-to-parameter ratio = 19.3
Details
Open access

5-Bromo-7-methyl-2-(4-methylphenyl)-3-methylsulfinyl-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, C17H15BrO2S, the 4-methylphenyl ring makes a dihedral angle of 14.46 (5)° with the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by pairs of Br...O contacts [3.151 (2) Å] into centrosymmetric dimers.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o215.]); Seo et al. (2009[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2302.]). For a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15BrO2S

  • Mr = 363.26

  • Triclinic, [P \overline 1]

  • a = 7.6375 (2) Å

  • b = 9.5170 (2) Å

  • c = 11.2413 (2) Å

  • [alpha] = 75.513 (1)°

  • [beta] = 84.848 (1)°

  • [gamma] = 71.626 (1)°

  • V = 750.72 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.88 mm-1

  • T = 173 K

  • 0.28 × 0.24 × 0.22 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 = 0.504, Tmax = 0.568

  • 14012 measured reflections

  • 3716 independent reflections

  • 3331 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.075

  • S = 1.05

  • 3716 reflections

  • 193 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.48 e Å-3

  • [Delta][rho]min = -0.56 e Å-3

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: RZ5021 ).


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., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o215.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.  [ISI] [CrossRef] [PubMed] [ChemPort]
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2302.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3464  [ doi:10.1107/S160053681204682X ]

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