Isopropyl 2-(5-iodo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

Hong Dae Choi; Pil Ja Seo; Byeng Wha Son; Uk Lee

doi:10.1107/S1600536808037471

. 2008 Nov 20;64(Pt 12):o2384. doi: 10.1107/S1600536808037471

Isopropyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate

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

PMCID: PMC2960084 PMID: 21581355

Abstract

In the title compound, C₁₄H₁₅IO₄S, 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 C—H⋯π interactions between a methyl H atom and the benzene ring of an adjacent molecule, and by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar isopropyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C₁₄H₁₅IO₄S
M _r = 406.22
Triclinic,
a = 8.0584 (7) Å
b = 10.1959 (9) Å
c = 10.8367 (9) Å
α = 70.369 (2)°
β = 81.926 (2)°
γ = 66.882 (1)°
V = 771.24 (12) Å³
Z = 2
Mo Kα radiation
μ = 2.22 mm⁻¹
T = 298 (2) K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T _min = 0.595, T _max = 0.806
4396 measured reflections
2965 independent reflections
2639 reflections with I > 2σ(I)
R _int = 0.011

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.079
S = 1.13
2965 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.57 e Å⁻³

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 Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037471/bq2107sup1.cif

e-64-o2384-sup1.cif^{(18.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037471/bq2107Isup2.hkl

e-64-o2384-Isup2.hkl^{(145.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg is the centroid of the C2–C7 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4ⁱ	0.93	2.57	3.451 (4)	159
C9—H9B⋯O4ⁱⁱ	0.97	2.41	3.373 (4)	170
C13—H13C⋯Cgⁱⁱⁱ	0.96	2.78	3.532 (5)	136

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

supplementary crystallographic information

Comment

As a part of our ongoing studies of the synthesis and structure of isopropyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, we have recently described the crystal structures of isopropyl 2-(5-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008a) and isopropyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl) acetate (Choi et al., 2008b). Here we report the crystal structure of the title compound, isopropyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl) acetate (Fig. 1). The benzofuran unit is essentially planar, with a mean deviation of 0.013 (2) Å from the least-squares plane defined by the nine constituent atoms. The molecular packing is stabilized by C—H···π interactions between a methyl H atom of isopropyl group and the benzene ring of the benzofuran unit, with a C13—H13C···Cgⁱⁱⁱ separation of 2.78 Å (Fig. 2 and Table 1; Cg is the centroid of the C2–C7 benzene ring, symmetry code as in Fig. 2). Also weak intermolecular C—H···O hydrogen bonds in the structure were observed (Table 1 & Fig. 2).

Experimental

77% 3-chloroperoxybenzoic acid (197 mg, 0.88 mmol) was added in small portions to a stirred solution of isopropyl 2-(5-iodo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (321 mg, 0.8 mmol) in dichloromethane (30 ml) at 273 K. After being stirred for 3 h at room temperature, the mixture was washed with saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated in vacuum. The residue was purified by column chromatography (hexane-ethyl acetate, 1:2 v/v) to afford the title compound as a colorless solid [yield 80%, m.p. 420–421 K; R_f = 0.63 (hexane-ethyl acetate, 1;2 v/v)]. Single crystals suitable for X–ray diffraction were prepared by evaporation of a solution of the title compound in acetone at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 1.27 (d, J = 6.20 Hz, 6H), 3.07 (s, 3H), 4.0 (s, 2H), 5.01-5.07 (m, 1H), 7.29 (d, J = 8.80 Hz, 1H), 7.66 (d, J = 8.76 Hz, 1H), 8.29 (s, 1H); EI-MS 406 [M⁺].