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Volume 69 
Part 7 
Page o1050  
July 2013  

Received 20 May 2013
Accepted 4 June 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.036
wR = 0.098
Data-to-parameter ratio = 18.6
Details
Open access

5-Chloro-2-methyl-3-(4-methylphenylsulfonyl)-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

The title compound, C16H13ClO3S, crystallized with two independent molecules in the asymmetric unit. The 4-methylphenyl rings make dihedral angles of 75.15 (4)° and 72.18 (4)° with the planes of the benzofuran ring systems in the two molecules. 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. (2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2350.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o2027.]).

[Scheme 1]

Experimental

Crystal data
  • C16H13ClO3S

  • Mr = 320.77

  • Triclinic, [P \overline 1]

  • a = 7.3725 (2) Å

  • b = 10.0967 (3) Å

  • c = 20.8173 (7) Å

  • [alpha] = 98.086 (1)°

  • [beta] = 99.547 (2)°

  • [gamma] = 106.547 (1)°

  • V = 1435.62 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.42 mm-1

  • T = 173 K

  • 0.41 × 0.29 × 0.23 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 = 0.670, Tmax = 0.746

  • 26328 measured reflections

  • 7109 independent reflections

  • 5967 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.098

  • S = 1.04

  • 7109 reflections

  • 383 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C26-C31 ring.

D-H...A D-H H...A D...A D-H...A
C15-H15...O2i 0.95 2.56 3.251 (2) 130
C27-H27...O6ii 0.95 2.55 3.248 (2) 131
C30-H30...O3iii 0.95 2.48 3.361 (2) 154
C22-H22...Cgiv 0.95 2.71 3.572 (2) 136
Symmetry codes: (i) -x, -y, -z+1; (ii) -x, -y, -z; (iii) x+1, y, z; (iv) -x+1, -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: PK2485 ).


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, o2027.  [CSD] [CrossRef] [IUCr Journals]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2350.  [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, o1050  [ doi:10.1107/S1600536813015468 ]

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