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

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

doi:10.1107/S160053681103933X

Volume 67
Part 10
Page o2805
October 2011

Received 14 September 2011
Accepted 25 September 2011
Online 30 September 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.044
wR = 0.143
Data-to-parameter ratio = 18.8
Details

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

Pil Ja Seo,^a Hong Dae Choi,^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

In the title compound, C₁₄H₁₅ClO₃S, the cyclopenyl ring adopts an envelope conformation. In the crystal, molecules are linked by weak intermolecular C-HO hydrogen bonds into dual chains propagating in [100]. The dual chains arise from pairs of the same or different hydrogen bonds between adjacent molecules.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009); Galal et al. (2009); Khan et al. (2005). For natural products with benzofuran rings, see: Akgul & Anil (2003); Soekamto et al. (2003). For the crystal structures of related compounds, see: Seo et al. (2011a,b).

Experimental

Crystal data

C₁₄H₁₅ClO₃S
M_r = 298.77
Triclinic, $[P \overline 1]$
a = 7.4833 (8) Å
b = 8.7888 (9) Å
c = 10.9061 (10) Å
= 66.919 (5)°
= 82.848 (6)°
= 82.689 (6)°
V = 652.31 (11) Å³
Z = 2
Mo K radiation
= 0.45 mm^-1
T = 173 K
0.39 × 0.27 × 0.22 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.844, T_max = 0.905
11884 measured reflections
3252 independent reflections
2721 reflections with I > 2(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.143
S = 1.05
3252 reflections
173 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.73 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O3ⁱ	0.95	2.51	3.420 (2)	160
C12-H12AO2ⁱⁱ	0.99	2.59	3.557 (2)	167
C13-H13BO3ⁱⁱ	0.99	2.61	3.516 (3)	153
Symmetry codes: (i) -x, -y+2, -z+1; (ii) x+1, y, 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: CV5153 ).

References

Akgul, Y. Y. & Anil, H. (2003). Phytochemistry, 63, 939-943.
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.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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.
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011a). Acta Cryst. E67, o1386.
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o1689.
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