5-Cyclo­hexyl-2-(3-fluoro­phen­yl)-3-methyl­sulfinyl-1-benzofuran

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

doi:10.1107/S1600536812008343

Volume 68
Part 4
Page o944
April 2012

Received 20 February 2012
Accepted 24 February 2012
Online 3 March 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.096
Data-to-parameter ratio = 19.8
Details

5-Cyclohexyl-2-(3-fluorophenyl)-3-methylsulfinyl-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, C₂₁H₂₁FO₂S, the cyclohexyl ring adopts a chair conformation. The 3-fluorophenyl ring makes a dihedral angle of 38.38 (6)° with the mean plane [r.m.s. deviation = 0.010 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C-HO hydrogen bonds.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011a,b).

Experimental

Crystal data

C₂₁H₂₁FO₂S
M_r = 356.44
Orthorhombic, P n a 2₁
a = 12.7767 (10) Å
b = 13.0764 (10) Å
c = 10.7711 (8) Å
V = 1799.6 (2) Å³
Z = 4
Mo K radiation
= 0.20 mm^-1
T = 173 K
0.34 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.935, T_max = 0.961
17893 measured reflections
4503 independent reflections
4036 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.096
S = 1.03
4503 reflections
227 parameters
1 restraint
H-atom parameters constrained
_max = 0.33 e Å^-3
_min = -0.25 e Å^-3
Absolute structure: Flack (1983), 2131 Friedel pairs
Flack parameter: -0.07 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C21-H21BO2ⁱ	0.98	2.30	3.276 (3)	176
Symmetry code: (i) $[-x+1, -y, z-{\script{1\over 2}}]$ .

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: BH2416 ).

Acknowledgements

This work was supported by a Dongeui University Foundation grant (2011).

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., 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.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds