5-Chloro-3-cyclo­hexyl­sulfinyl-2-methyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536811007859

Volume 67
Part 4
Page o804
April 2011

Received 28 February 2011
Accepted 2 March 2011
Online 9 March 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.033
wR = 0.084
Data-to-parameter ratio = 19.1
Details

5-Chloro-3-cyclohexylsulfinyl-2-methyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b 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

There are two independent molecules in the asymmetric unit of the title compound, C₁₅H₁₇ClO₂S, in each of which the cyclohexyl rings adopt chair conformations. In the crystal, molecules are linked by weak intermolecular C-HO hydrogen bonds.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2006); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the structure of 5-bromo-3-cyclohexylsulfinyl-2-methyl-1-benzofuran, see: Choi et al. (2011).

Experimental

Crystal data

C₁₅H₁₇ClO₂S
M_r = 296.80
Monoclinic, P 2₁
a = 12.0755 (2) Å
b = 9.0033 (2) Å
c = 13.9112 (2) Å
= 108.667 (1)°
V = 1432.86 (4) Å³
Z = 4
Mo K radiation
= 0.41 mm^-1
T = 173 K
0.28 × 0.24 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.896, T_max = 0.932
14184 measured reflections
6583 independent reflections
6143 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.084
S = 1.03
6583 reflections
345 parameters
1 restraint
H-atom parameters constrained
_max = 0.40 e Å^-3
_min = -0.37 e Å^-3
Absolute structure: Flack (1983), 2822 Friedel pairs
Flack parameter: 0.03 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O2ⁱ	0.95	2.54	3.469 (3)	166
Symmetry code: (i) x, y+1, z.

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, 1997) 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: HG5004 ).

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.
Aslam, S. N., Stevenson, P. C., Phythian, S. J., Veitch, N. C. & Hall, D. R. (2006). Tetrahedron, 62, 4214-4226.
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. (2011). Acta Cryst. E67, o527.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Soekamto, N. H., Achmad, S. A., Ghisalberti, E. L., Hakim, E. H. & Syah, Y. M. (2003). Phytochemistry, 64, 831-834.

organic compounds