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Volume 68 
Part 12 
Page o3336  
December 2012  

Received 22 October 2012
Accepted 7 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.040
wR = 0.103
Data-to-parameter ratio = 19.2
Details
Open access

5-Cyclopentyl-2-(4-fluorophenyl)-3-isopropylsulfonyl-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, C22H23FO3S, the cyclopentyl ring adopts an envelope conformation with the flap atom connected to the benzofuran residue. The 4-fluorophenyl ring makes a dihedral angle of 43.67 (3)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C-H...O and C-H...[pi] interactions, forming a three--dimensional network. The crystal structure also exhibits slipped [pi]-[pi] interactions between the benzene and furan rings of neighbouring molecules [centroid-centroid distance = 3.883 (2) Å and slippage = 1.731 (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, o1000.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2591.]).

[Scheme 1]

Experimental

Crystal data
  • C22H23FO3S

  • Mr = 386.46

  • Monoclinic, P 21 /n

  • a = 9.4736 (3) Å

  • b = 19.6185 (7) Å

  • c = 10.8018 (3) Å

  • [beta] = 108.833 (1)°

  • V = 1900.12 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 173 K

  • 0.40 × 0.39 × 0.36 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 = 0.678, Tmax = 0.746

  • 18610 measured reflections

  • 4714 independent reflections

  • 3948 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.103

  • S = 1.03

  • 4714 reflections

  • 246 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.35 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2-C7 benzene ring.

D-H...A D-H H...A D...A D-H...A
C6-H6...O2i 0.95 2.60 3.3341 (17) 135
C18-H18...O3ii 0.95 2.48 3.2932 (19) 144
C21-H21A...Cg1iii 0.98 2.71 3.693 (2) 177
Symmetry codes: (i) x-1, y, z; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) -x+1, -y+1, -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 (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: FY2075 ).


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., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o1000.  [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, o2591.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3336  [ doi:10.1107/S1600536812045916 ]

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