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Volume 69 
Part 6 
Page o820  
June 2013  

Received 17 April 2013
Accepted 30 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.023
wR = 0.062
Data-to-parameter ratio = 18.7
Details
Open access

2-(4-Fluorophenyl)-5-iodo-7-methyl-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

In the title compound, C21H14FIO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.007 (1) Å] of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 3.66 (7) and 82.37 (6)°, respectively. In the crystal, molecules are linked by pairs of C-H...I hydrogen bonds into centrosymmetric dimers, which are further packed into stacks along the b axis by C-H...O hydrogen bonds. In addition, the stacked molecules exhibit inversion-related S...O contacts [2.9627 (14) Å] involving the sulfinyl groups.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o1809.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o1237.]). For details of sulfinyl-sulfinyl interactions, see: Choi et al. (2008[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008). Acta Cryst. E64, o1061.]) and for a review of carbonyl-carbonyl interactions, see: Allen et al. (1998[Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.]).

[Scheme 1]

Experimental

Crystal data
  • C21H14FIO2S

  • Mr = 476.28

  • Triclinic, [P \overline 1]

  • a = 8.1060 (3) Å

  • b = 10.7771 (4) Å

  • c = 11.2639 (4) Å

  • [alpha] = 71.814 (2)°

  • [beta] = 74.496 (2)°

  • [gamma] = 79.038 (2)°

  • V = 894.69 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 1.93 mm-1

  • T = 173 K

  • 0.36 × 0.28 × 0.19 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 = 0.562, Tmax = 0.746

  • 16292 measured reflections

  • 4404 independent reflections

  • 4125 reflections with I > 2[sigma](I)

  • Rint = 0.036

Refinement
  • R[F2 > 2[sigma](F2)] = 0.023

  • wR(F2) = 0.062

  • S = 1.05

  • 4404 reflections

  • 236 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.63 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C20-H20...O2i 0.95 2.36 3.314 (3) 177
C17-H17...I1ii 0.95 2.97 3.705 (2) 135
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z+2.

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: LD2102 ).


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

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.  [ISI] [CrossRef] [details]
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. (2008). Acta Cryst. E64, o1061.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o1809.  [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, o820  [ doi:10.1107/S1600536813011793 ]

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