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Volume 69 
Part 9 
Page o1452  
September 2013  

Received 5 August 2013
Accepted 12 August 2013
Online 21 August 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.100
Data-to-parameter ratio = 17.0
Details
Open access

5-Cyclohexyl-2-(4-fluorophenyl)-3-phenylsulfinyl-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

The asymmetric unit of the title compound, C26H23FO2S, contains two independent molecules (A and B), in both of which the cyclohexyl ring adopts a chair conformation. The benzofuran ring systems, the 4-fluorophenyl and phenyl rings are essentially planar, with r.m.s. deviations of 0.008 (1), 0.002 (1) and 0.003 (1) Å, respectively, for molecule A, and 0.016 (1), 0.004 (1) and 0.002 (1) Å, respectively, for molecule B. The dihedral angles between the benzofuran ring system and the pendant 4-fluorophenyl and phenyl rings are 12.3 (7) and 85.42 (4)°, respectively, for molecule A, and 39.67 (6) and 72.17 (4)°, respectively, for molecule B. In the crystal, molecules are linked by weak C-H...O and C-H...[pi] interactions, resulting in a three-dimensional network.

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, o498.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1237.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.]).

[Scheme 1]

Experimental

Crystal data
  • C26H23FO2S

  • Mr = 418.50

  • Triclinic, [P \overline 1]

  • a = 9.1536 (2) Å

  • b = 12.6562 (2) Å

  • c = 19.3939 (4) Å

  • [alpha] = 84.674 (1)°

  • [beta] = 79.667 (1)°

  • [gamma] = 72.405 (1)°

  • V = 2105.15 (7) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.18 mm-1

  • T = 173 K

  • 0.38 × 0.27 × 0.25 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 = 0.702, Tmax = 0.746

  • 36372 measured reflections

  • 9183 independent reflections

  • 7799 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.100

  • S = 1.03

  • 9183 reflections

  • 541 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C41-C46 4-fluorophenyl ring and the C2-C7 benzene ring, respectively.

D-H...A D-H H...A D...A D-H...A
C10-H10B...O2i 0.99 2.47 3.384 (2) 153
C22-H22...O2i 0.95 2.42 3.2365 (19) 144
C19-H19...O4ii 0.95 2.44 3.3442 (19) 159
C40-H40B...Cg1iii 0.99 2.84 3.763 (2) 155
C45-H45...Cg2 0.95 2.82 3.602 (2) 140
C50-H50...Cg1iv 0.95 2.80 3.619 (2) 144
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x, -y+1, -z+1; (iii) -x, -y+2, -z+1; (iv) -x+1, -y+1, -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: MW2115 ).


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, o1237.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o498.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1452  [ doi:10.1107/S1600536813022678 ]

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