5-Iodo-2,7-dimethyl-3-phenyl­sulfonyl-1-benzofuran

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536808011240

Volume 64
Part 5
Page o930
May 2008

Received 18 April 2008
Accepted 20 April 2008
Online 30 April 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R = 0.027
wR = 0.075
Data-to-parameter ratio = 17.0
Details

5-Iodo-2,7-dimethyl-3-phenylsulfonyl-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b 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

The title compound, C₁₆H₁₃IO₃S, was prepared by the oxidation of 5-iodo-2,7-dimethyl-3-phenylsulfanyl-1-benzofuran with 3-chloroperoxybenzoic acid. The phenyl ring makes a dihedral angle of 76.31 (8)° with the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic [pi] - [pi] interactions between the furan and benzene rings of neighbouring molecules, and between the benzene rings of neighbouring molecules; the centroid-centroid distances within the stack are 3.700 (4) and 3.788 (4) Å. In addition, the crystal structure exhibits inter- and intramolecular C-HO interactions, and an IO halogen bond with an IO distance of 3.282 (2) Å and a nearly linear C-IO angle of 165.69 (8)°.

Related literature

For the crystal structures of similar 3-phenylsulfonyl-1-benzofuran compounds, see: Choi et al. (2008a,b). For a review of halogen bonding, see: Politzer et al. (2007).

Experimental

Crystal data

C₁₆H₁₃IO₃S
M_r = 412.22
Monoclinic, P 2₁ /n
a = 8.1165 (5) Å
b = 14.0295 (9) Å
c = 13.2470 (8) Å
= 90.320 (1)°
V = 1508.42 (16) Å³
Z = 4
Mo K radiation
= 2.27 mm^-1
T = 173 (2) K
0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) T_min = 0.579, T_max = 0.641
9110 measured reflections
3285 independent reflections
3069 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.026
wR(F²) = 0.074
S = 0.99
3285 reflections
193 parameters
H-atom parameters constrained
_max = 1.13 e Å^-3
_min = -1.01 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11O1ⁱ	0.95	2.59	3.382 (4)	141
C13-H13O3ⁱⁱ	0.95	2.44	3.342 (4)	159
C14-H14O2	0.95	2.58	2.931 (4)	103
C16-H16BO3	0.98	2.48	3.191 (4)	129
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x-1, y, z.

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); 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: ZL2112 ).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o793.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o794.
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. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds