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Volume 68 
Part 11 
Page o3192  
November 2012  

Received 15 October 2012
Accepted 17 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.025
wR = 0.060
Data-to-parameter ratio = 19.4
Details
Open access

2-(4-Fluorophenyl)-5-iodo-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

There are two symmetry-independent molecules, A and B, in the asymmetric unit of the title compound, C17H14FIO3S. The dihedral angle formed by the 4-fluorophenyl ring and the mean plane [r.m.s. deviation = 0.013 (2) Å in molecule A and 0.016 (2) Å in molecule B] of the benzofuran fragment is 57.71 (7)° in molecule A and 44.95 (7)° in molecule B. In the crystal, molecules are linked by weak C-H...O hydrogen bonds and I...O contacts [I...O = 3.3646 (15) and 3.2354 (14) Å], forming a three--dimensional network.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010a). Acta Cryst. E66, o1043.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o3261.]). For a review of halogen bonding, see: Politzer et al. (2007[Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.]).

[Scheme 1]

Experimental

Crystal data
  • C17H14FIO3S

  • Mr = 444.24

  • Triclinic, [P \overline 1]

  • a = 11.7419 (2) Å

  • b = 12.8226 (2) Å

  • c = 12.8474 (2) Å

  • [alpha] = 66.576 (1)°

  • [beta] = 82.703 (1)°

  • [gamma] = 67.769 (1)°

  • V = 1642.36 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.10 mm-1

  • T = 173 K

  • 0.31 × 0.22 × 0.22 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 = 0.594, Tmax = 0.746

  • 30779 measured reflections

  • 8149 independent reflections

  • 7224 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.025

  • wR(F2) = 0.060

  • S = 1.01

  • 8149 reflections

  • 419 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -0.88 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6...O1i 0.95 2.56 3.418 (2) 150
C15-H15...O2ii 1.00 2.52 3.520 (3) 177
C30-H30...O2iii 0.95 2.58 3.463 (3) 155
C31-H31...O3iii 0.95 2.58 3.260 (2) 129
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+1, -z+1; (iii) 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 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) 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: LD2079 ).


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. (2010a). Acta Cryst. E66, o1043.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o3261.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3192  [ doi:10.1107/S1600536812043218 ]

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