[Journal logo]

Volume 69 
Part 6 
Page o894  
June 2013  

Received 30 April 2013
Accepted 1 May 2013
Online 15 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.044
wR = 0.116
Data-to-parameter ratio = 19.6
Details
Open access

5-Cyclohexyl-3-(2-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 2-fluorophenyl ring makes a dihedral angle of 88.47 (4)° with the mean plane [r.m.s. deviation = 0.013 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C-H...O and C-H...[pi] interactions, forming chains propagating along [100]. The crystal structure also exhibits slipped [pi]-[pi] interactions between the furan rings of neighboring molecules [centroid-to-centroid distance = 3.397 (2) Å, interplanar distance = 3.346 (2) Å and slippage = 0.586 (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, o768.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o205.]).

[Scheme 1]

Experimental

Crystal data
  • C21H21FO2S

  • Mr = 356.44

  • Triclinic, [P \overline 1]

  • a = 9.0667 (2) Å

  • b = 10.3647 (2) Å

  • c = 10.6838 (2) Å

  • [alpha] = 105.395 (1)°

  • [beta] = 93.418 (1)°

  • [gamma] = 110.839 (1)°

  • V = 891.33 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 173 K

  • 0.30 × 0.22 × 0.21 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 = 0.681, Tmax = 0.746

  • 16785 measured reflections

  • 4455 independent reflections

  • 3495 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.116

  • S = 1.04

  • 4455 reflections

  • 227 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2-C7 benzene ring.

D-H...A D-H H...A D...A D-H...A
C3-H3...O2i 0.95 2.60 3.5024 (19) 160
C20-H20...O1ii 0.95 2.53 3.316 (2) 140
C21-H21...O2i 0.95 2.49 3.332 (2) 148
C14-H14B...Cg2iii 0.99 2.69 3.618 (2) 156
C15-H15B...Cg2iv 0.98 2.85 3.422 (2) 118
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y, z; (iii) -x+1, -y+1, -z+1; (iv) -x+2, -y+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 (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: ZL2547 ).


Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (grant No. 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, o205.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o768.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o894  [ doi:10.1107/S1600536813011902 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.