2-(4-Fluoro­phen­yl)-5-iodo-3-isopropyl­sulfonyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812043218

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 (C-C) = 0.003 Å
R = 0.025
wR = 0.060
Data-to-parameter ratio = 19.4
Details

2-(4-Fluorophenyl)-5-iodo-3-isopropylsulfonyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a and Uk Lee ^b ^*

^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-HO hydrogen bonds and IO contacts [IO = 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,b). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental

Crystal data

C₁₇H₁₄FIO₃S
M_r = 444.24
Triclinic, $[P \overline 1]$
a = 11.7419 (2) Å
b = 12.8226 (2) Å
c = 12.8474 (2) Å
= 66.576 (1)°
= 82.703 (1)°
= 67.769 (1)°
V = 1642.36 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.594, T_max = 0.746
30779 measured reflections
8149 independent reflections
7224 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.025
wR(F²) = 0.060
S = 1.01
8149 reflections
419 parameters
H-atom parameters constrained
_max = 0.65 e Å^-3
_min = -0.88 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C6-H6O1ⁱ	0.95	2.56	3.418 (2)	150
C15-H15O2ⁱⁱ	1.00	2.52	3.520 (3)	177
C30-H30O2ⁱⁱⁱ	0.95	2.58	3.463 (3)	155
C31-H31O3ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); 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.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010b). Acta Cryst. E66, o3261.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305-311.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds