3-(4-Bromo­phenyl­sulfon­yl)-5-ethyl-2-methyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812048313

Volume 68
Part 12
Page o3487
December 2012

Received 8 November 2012
Accepted 25 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R = 0.034
wR = 0.067
Data-to-parameter ratio = 15.3
Details

3-(4-Bromophenylsulfonyl)-5-ethyl-2-methyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a and Uk Lee ^b ^*

^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, C₁₇H₁₅BrO₃S, the 4-bromophenyl ring makes a dihedral angle of 76.58 (9)° with the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C-HO and C-H [pi] interactions.

Related literature

For the biological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For the crystal structures of related compounds, see: Choi et al. (2010, 2011).

Experimental

Crystal data

C₁₇H₁₅BrO₃S
M_r = 379.26
Tetragonal, P 4₃
a = 10.2785 (3) Å
c = 15.2899 (6) Å
V = 1615.34 (9) Å³
Z = 4
Mo K radiation
= 2.68 mm^-1
T = 173 K
0.31 × 0.17 × 0.15 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.450, T_max = 0.746
8518 measured reflections
3085 independent reflections
2558 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.034
wR(F²) = 0.067
S = 1.03
3085 reflections
201 parameters
1 restraint
H-atom parameters constrained
_max = 0.35 e Å^-3
_min = -0.29 e Å^-3
Absolute structure: Flack (1983), 1000 Friedel pairs
Flack parameter: 0.001 (7)

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2-C7 benzene ring.

D-HA	D-H	HA	DA	D-HA
C6-H6O3ⁱ	0.95	2.53	3.238 (4)	131
C11-H11AO3ⁱⁱ	0.98	2.58	3.321 (4)	132
C14-H14Cgⁱⁱⁱ	0.95	2.70	3.495 (4)	142
Symmetry codes: (i) $[-x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[-y+1, x, z-{\script{1\over 4}}]$ ; (iii) $[y, -x+1, z+{\script{1\over 4}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RN2111 ).

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

Aslam, S. N., Stevenson, P. C., Kokubun, T. & Hall, D. R. (2009). Microbiol. Res. 164, 191-195.
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, o2575.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1278.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Galal, S. A., Abd El-All, A. S., Abdallah, M. M. & El-Diwani, H. I. (2009). Bioorg. Med. Chem. Lett. 19, 2420-2428.
Khan, M. W., Alam, M. J., Rashid, M. A. & Chowdhury, R. (2005). Bioorg. Med. Chem. 13, 4796-4805.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds