5-Cyclo­pentyl-3-methyl­sulfinyl-2-phenyl-1-benzofuran

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

doi:10.1107/S1600536811010920

Volume 67
Part 4
Page o1000
April 2011

Received 21 March 2011
Accepted 23 March 2011
Online 31 March 2011

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
Disorder in main residue
R = 0.055
wR = 0.139
Data-to-parameter ratio = 16.4
Details

5-Cyclopentyl-3-methylsulfinyl-2-phenyl-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

In the title compound, C₂₀H₂₀O₂S, the cyclopentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The phenyl ring makes a dihedral angle of 32.36 (9)° with the mean plane of the benzofuran fragment. In the crystal, molecules are linked through weak C-HO interactions. In the cyclopentyl ring, two adjacent C atoms are disordered over two sets of sites with site occupancy factors of 0.675 (8) and 0.325 (8).

Related literature

For the biological 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 structural studies of related 2-aryl-5-cyclohexyl-3-methylsulfinyl-1-benzofuran derivatives, see: Choi et al. (2011a,b).

Experimental

Crystal data

C₂₀H₂₀O₂S
M_r = 324.42
Monoclinic, P 2₁ /c
a = 5.9586 (7) Å
b = 25.397 (3) Å
c = 10.7804 (12) Å
= 90.038 (2)°
V = 1631.4 (3) Å³
Z = 4
Mo K radiation
= 0.21 mm^-1
T = 173 K
0.34 × 0.15 × 0.12 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.934, T_max = 0.976
15888 measured reflections
3749 independent reflections
2998 reflections with I > 2(I)
R_int = 0.043

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.139
S = 1.06
3749 reflections
228 parameters
36 restraints
H-atom parameters constrained
_max = 0.42 e Å^-3
_min = -0.37 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C19-H19O2ⁱ	0.95	2.53	3.324 (3)	142
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: TK2730 ).

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. (2011a). Acta Cryst. E67, o281.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011b). Acta Cryst. E67, o470.
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.
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