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Volume 69 
Part 7 
Page o1026  
July 2013  

Received 23 May 2013
Accepted 29 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.042
wR = 0.124
Data-to-parameter ratio = 19.2
Details
Open access

5-Cyclohexyl-3-(3-fluorophenylsulfinyl)-2-methyl-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, C21H21FO2S, the cyclohexyl ring adopts a chair conformation. The 3-fluorophenyl ring makes a dihedral angle of 83.16 (4)° with the mean plane [r.m.s. deviation = 0.005 (1) Å] of the benzofuran ring system. In the crystal, molecules are linked by pairs of C-H...[pi] interactions into inversion dimers, which are further packed into stacks along the a-axis direction by C-H...[pi] interactions.

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, o1157.], 2012a[Choi, H. D., Seo, P. J. & Lee, U. (2012a). Acta Cryst. E68, o205.],b[Choi, H. D., Seo, P. J. & Lee, U. (2012b). Acta Cryst. E68, o947.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21FO2S

  • Mr = 356.44

  • Triclinic, [P \overline 1]

  • a = 8.9147 (1) Å

  • b = 10.1270 (2) Å

  • c = 10.5101 (2) Å

  • [alpha] = 90.376 (1)°

  • [beta] = 110.407 (1)°

  • [gamma] = 97.439 (1)°

  • V = 880.44 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 173 K

  • 0.33 × 0.31 × 0.29 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 = 0.692, Tmax = 0.746

  • 19435 measured reflections

  • 4369 independent reflections

  • 3897 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.124

  • S = 1.04

  • 4369 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.94 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1/C2/C7/O1/C8 furan ring and the C2-C7 benzene ring, respectively.

D-H...A D-H H...A D...A D-H...A
C13-H13A...Cg1i 0.99 3.00 3.697 (1) 128
C14-H14B...Cg2i 0.99 2.91 3.569 (1) 125
C19-H19...Cg2ii 0.95 2.90 3.677 (1) 140
Symmetry codes: (i) -x+1, -y, -z+1; (ii) x+1, y, z.

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: BX2442 ).


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. (2012a). Acta Cryst. E68, o205.  [CSD] [CrossRef] [IUCr Journals]
Choi, H. D., Seo, P. J. & Lee, U. (2012b). Acta Cryst. E68, o947.  [CSD] [CrossRef] [IUCr Journals]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1157.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1026  [ doi:10.1107/S160053681301475X ]

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