(IUCr) Methyl 2-(5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate

Volume 65
Part 6
Page o1240
June 2009

Received 5 March 2009
Accepted 30 April 2009
Online 14 May 2009

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.007 Å
R = 0.050
wR = 0.088
Data-to-parameter ratio = 17.9
Details

Methyl 2-(5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate

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

There are two symmetry-independent molecules in the asymmetric unit of the title compound, C₁₃H₁₃IO₄S. In each molecule, the O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by aromatic [pi] - [pi] interactions between the benzene and furan ring [centroid-centroid distance = 3.866 (7) Å], and by intermolecular C-H [pi] interactions and a sulfinyl-sulfinyl interaction [SO = 3.025 (4) Å]. The crystal structure also exhibits weak intermolecular C-HO hydrogen bonds and two different IO halogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2008a,b). For halogen bonding, see: Politzer et al. (2007). For carbonyl-carbonyl interactions, see: Allen et al. (1998).

Experimental

Crystal data

C₁₃H₁₃IO₄S
M_r = 392.19
Triclinic, $[P \overline 1]$
a = 7.5424 (4) Å
b = 11.2177 (6) Å
c = 17.845 (1) Å
= 77.701 (1)°
= 88.074 (1)°
= 88.229 (1)°
V = 1473.92 (14) Å³
Z = 4
Mo K radiation
= 2.32 mm^-1
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) T_min = 0.574, T_max = 0.790
12617 measured reflections
6248 independent reflections
5328 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.088
S = 1.18
6248 reflections
349 parameters
H-atom parameters constrained
_max = 1.15 e Å^-3
_min = -1.46 e Å^-3

Table 1
Selected interatomic distances (Å)

I1O7ⁱ	3.300 (3)
I2O3ⁱⁱ	3.264 (3)
Symmetry codes: (i) x, y-1, z+1; (ii) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C5-H5O3ⁱⁱⁱ	0.93	2.59	3.430 (6)	150
C11-H11BO8	0.96	2.51	3.254 (6)	134
C12-H12CO4^iv	0.96	2.58	3.489 (6)	158
C16-H16O8^v	0.93	2.48	3.373 (6)	160
C18-H18O4^vi	0.93	2.44	3.297 (6)	153
C22-H22BO8^vii	0.97	2.27	3.215 (6)	164
C12-H12ACg1ⁱⁱⁱ	0.96	2.85	3.734 (7)	153
C24-H24ACg3^viii	0.96	2.73	3.574 (7)	147
Symmetry codes: (iii) -x+1, -y, -z+1; (iv) -x+2, -y, -z+1; (v) -x+2, -y+1, -z; (vi) -x+2, -y+1, -z+1; (vii) -x+1, -y+1, -z; (viii) -x+1, -y+2, -z. Cg1 and Cg3 are the centroids of the C2-C7 benzene ring and the C14/C15/C20/O5/C21 furan ring, respectively.

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: GW2062 ).

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320-329.
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, o2384.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o2431.
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. (1999). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds