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Volume 69 
Part 8 
Page o1299  
August 2013  

Received 25 June 2013
Accepted 18 July 2013
Online 24 July 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.033
wR = 0.085
Data-to-parameter ratio = 17.1
Details
Open access

3-(2-Bromophenylsulfinyl)-2,5,7-trimethyl-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, both the benzofuran and 2-bromophenyl rings are virtually planar, with r.m.s. deviations of 0.009 (2) and 0.006 (2) Å, respectively. The dihedral angle between these mean planes is 89.31 (7)°. In the crystal, molecules are linked via pairs of C-H...[pi] interactions into inversion dimers. These dimers are further linked by C-H...[pi] interactions into supramolecular chains running along the b axis. In addition, C-S...[pi] interactions, with an S-to-ring-centroid distance of 3.50 (2) Å, are observed between inversion-related 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, o472.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o482.]).

[Scheme 1]

Experimental

Crystal data
  • C17H15BrO2S

  • Mr = 363.26

  • Triclinic, [P \overline 1]

  • a = 7.540 (3) Å

  • b = 8.415 (3) Å

  • c = 12.722 (4) Å

  • [alpha] = 98.933 (19)°

  • [beta] = 105.001 (19)°

  • [gamma] = 93.530 (18)°

  • V = 765.9 (5) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.82 mm-1

  • T = 173 K

  • 0.32 × 0.26 × 0.20 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 = 0.522, Tmax = 0.746

  • 12648 measured reflections

  • 3304 independent reflections

  • 2857 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.033

  • wR(F2) = 0.085

  • S = 1.12

  • 3304 reflections

  • 193 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.54 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2-C7 benzene ring and the C1/C2/C7/O1/C8 furan ring, respectively.

D-H...A D-H H...A D...A D-H...A
C9-H9C...Cg1i 0.98 2.92 3.594 (3) 127
C16-H16...Cg2ii 0.95 2.78 3.551 (3) 139
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) x, y+1, 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: FJ2637 ).


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, U. (2012). Acta Cryst. E68, o482.  [CSD] [CrossRef] [IUCr Journals]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o472.  [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, o1299  [ doi:10.1107/S1600536813019867 ]

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