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Volume 69 
Part 9 
Page o1462  
September 2013  

Received 13 August 2013
Accepted 18 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.074
Data-to-parameter ratio = 13.0
Details
Open access

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

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, C22H23FO2S, the cyclohexyl ring adopts a chair conformation. The dihedral angle between the mean plane [r.m.s. deviation = 0.013 (2) Å] of the benzofuran ring system and the mean plane [r.m.s. deviation = 0.009 (2) Å] of the 3-fluorophenyl ring is 24.80 (4)°. In the crystal, molecules are connected by C-H...O hydrogen bonds, forming chains along [10-1]. These chains are linked via C-H...F hydrogen bonds, forming a three-dimensional structure. There are also interplanar interactions present involving the furan ring of the benzofuran ring system and the 3-fluorophenyl ring [centroid-centroid distance = 3.728 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2011[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o470.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o944.]).

[Scheme 1]

Experimental

Crystal data
  • C22H23FO2S

  • Mr = 370.46

  • Monoclinic, C c

  • a = 15.1363 (5) Å

  • b = 15.9252 (6) Å

  • c = 10.6440 (6) Å

  • [beta] = 133.053 (1)°

  • V = 1874.83 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 173 K

  • 0.40 × 0.29 × 0.19 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.634, Tmax = 0.746

  • 8392 measured reflections

  • 3085 independent reflections

  • 2842 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.074

  • S = 1.04

  • 3085 reflections

  • 237 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1045 (51%) Friedel pairs

  • Absolute structure parameter: 0.05 (7)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16...O2i 0.95 2.54 3.291 (3) 136
C3-H3...F1ii 0.95 2.54 3.438 (3) 159
Symmetry codes: (i) [x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, y+{\script{1\over 2}}, z-1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2636 ).


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

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. & Lee, U. (2012). Acta Cryst. E68, o944.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o470.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1462  [ doi:10.1107/S1600536813023180 ]

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