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

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

doi:10.1107/S1600536809016298

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1240

doi:10.1107/S1600536809016298

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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

(Received 5 March 2009; accepted 30 April 2009; online 14 May 2009)

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 π–π interactions between the benzene and furan ring [centroid–centroid distance = 3.866 (7) Å], and by intermolecular C—H⋯π interactions and a sulfinyl–sulfinyl interaction [S⋯O = 3.025 (4) Å]. The crystal structure also exhibits weak intermolecular C—H⋯O hydrogen bonds and two different I⋯O 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
α = 77.701 (1)°
β = 88.074 (1)°
γ = 88.229 (1)°
V = 1473.92 (14) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.088
S = 1.18
6248 reflections
349 parameters
H-atom parameters constrained
Δρ_max = 1.15 e Å⁻³
Δρ_min = −1.46 e Å⁻³

Table 1
Selected interatomic distances (Å)

I1⋯O7ⁱ	3.300 (3)
I2⋯O3ⁱⁱ	3.264 (3)
Symmetry codes: (i) x, y-1, z+1; (ii) x+1, y, z.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3ⁱⁱⁱ	0.93	2.59	3.430 (6)	150
C11—H11B⋯O8	0.96	2.51	3.254 (6)	134
C12—H12C⋯O4^iv	0.96	2.58	3.489 (6)	158
C16—H16⋯O8^v	0.93	2.48	3.373 (6)	160
C18—H18⋯O4^vi	0.93	2.44	3.297 (6)	153
C22—H22B⋯O8^vii	0.97	2.27	3.215 (6)	164
C12—H12A⋯Cg1ⁱⁱⁱ	0.96	2.85	3.734 (7)	153
C24—H24A⋯Cg3^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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809016298/gw2062sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809016298/gw2062Isup2.hkl

checkCIF report

Comment top

This work is related to our previous communications on the synthesis and structure of alkyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, viz. isopropyl 2-(5-iodo-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008a) and isopropyl 2-(5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008b). Here we report the crystal structure of the title compound, methyl 2-(5-iodo-7-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Fig. 1). The benzofuran unit is essentially planar, with a mean deviation of 0.017 (4) Å for two independent molecules, from the least-squares plane defined by the nine constituent atoms.

The molecular packing (Fig. 2 & 3) is stabilized by aromatic π—π interactions between the benzene ring and the furan ring of adjacent benzofuran units, with a Cg1···Cg2^ix distance of 3.866 (7) Å (Cg1 and Cg2 are the centroids of the C2–C7 benzene ring and the C1/C2/C7/O1/C8 furan ring; symmetry code as in Fig. 3). The crystal packing is further stabilized by C—H···π interactions (Table 2 and Fig. 3); the first between the methyl H atom and the benzene ring of the benzofuran unit, i.e. C12—H12A···Cg1ⁱⁱⁱ, the second between the methyl H atom and the furan ring of the benzofuran unit, i.e. C24—H24A···Cg3^viii, respectively (Cg3 is the centroid of the C14/C15/C20/O5/C21 furan ring; symmetry code as in Fig. 3), and by an intermolecular sulfinyl–sulfinyl interaction interpreted as simliar to a type–II carbonyl–carbonyl interaction (Allen et al., 1998), with S1···O4^xi and O4···S1^xi distance of 3.025 (4) Å (Fig. 3; symmetry code as in Fig. 3). In addition, the crystal packing exhibits weak intermolecular C—H···O hydrogen bonds (Fig. 2 and Table 2). In crystal structure, there are two different I···O halogen bonds (Politzer et al., 2007) between the two independent iodine atoms and the oxygen atoms of neighbouring C═O units (Fig. 2 and Table 1).

Related literature top

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). Cg1 and Cg3 are the centroids of the C2–C7 benzene ring and the C14/C15/C20/O5/C21 furan ring, respectively.

Experimental top

77% 3–chloroperoxybenzoic acid (123 mg, 0.55 mmol) was added in small portions to a stirred solution of methyl 2-(5-iodo-7-methyl-3-methylsulfanyl-1-benzofuran-2-yl)acetate (202 mg, 0.5 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 (ethyl acetate) to afford the title compound as a colorless solid [yield 83%, m.p. 414–415 K; R_f = 0.63 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 2.46 (s, 3H), 3.05 (s, 3H), 3.76 (s, 3H), 4.07 (s, 2H), 7.49 (s, 1H), 8.07 (s, 1H); EI—MS 392 [M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. C—H···O hydrogen bond and I···O halogen bond (dotted lines) in the title compound [Symmetry code: (i) x, y - 1, z + 1; (ii) x + 1, y, z; (iii) -x + 1, -y, -z + 1; (iv) -x + 2, -y, -z + 1; (v) -x + 2, -y + 1, -z; (vi) 2 - x, 1 - y, 1 - z; (vii) - x + 1, - y + 1, - z.]
	Fig. 3. π—π, C—H···π, and S···O interactions (dotted lines) in the title compound. Cg denotes the ring centroids [Symmetry code: (iii) - x + 1, - y, - z + 1; (viii) - x + 1, - y + 2, - z; (ix) - x + 2, - y, - z + 1; (x) x + 1, y, z; (xi) - x + 2, - y + 1, - z + 1.]

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

Crystal data top

C₁₃H₁₃IO₄S	Z = 4
M_r = 392.19	F(000) = 768
Triclinic, P1	D_x = 1.767 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5424 (4) Å	Cell parameters from 6307 reflections
b = 11.2177 (6) Å	θ = 2.3–28.2°
c = 17.845 (1) Å	µ = 2.32 mm⁻¹
α = 77.701 (1)°	T = 293 K
β = 88.074 (1)°	Block, colorless
γ = 88.229 (1)°	0.30 × 0.20 × 0.10 mm
V = 1473.92 (14) Å³

Data collection top

Bruker SMART CCD diffractometer	6248 independent reflections
Radiation source: fine-focus sealed tube	5328 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
Detector resolution: 10.0 pixels mm^-1	θ_max = 27.0°, θ_min = 1.9°
ϕ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −14→14
T_min = 0.574, T_max = 0.790	l = −22→22
12617 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.050	Hydrogen site location: difference Fourier map
wR(F²) = 0.088	H-atom parameters constrained
S = 1.18	w = 1/[σ²(F_o²) + (0.0184P)² + 4.3135P] where P = (F_o² + 2F_c²)/3
6248 reflections	(Δ/σ)_max < 0.001
349 parameters	Δρ_max = 1.15 e Å⁻³
0 restraints	Δρ_min = −1.46 e Å⁻³

Crystal data top

C₁₃H₁₃IO₄S	γ = 88.229 (1)°
M_r = 392.19	V = 1473.92 (14) Å³
Triclinic, P1	Z = 4
a = 7.5424 (4) Å	Mo Kα radiation
b = 11.2177 (6) Å	µ = 2.32 mm⁻¹
c = 17.845 (1) Å	T = 293 K
α = 77.701 (1)°	0.30 × 0.20 × 0.10 mm
β = 88.074 (1)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.088	H-atom parameters constrained
S = 1.18	Δρ_max = 1.15 e Å⁻³
6248 reflections	Δρ_min = −1.46 e Å⁻³
349 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
I1	0.66948 (5)	−0.00958 (3)	0.780861 (19)	0.03974 (11)
S1	0.92033 (15)	0.36686 (11)	0.47095 (7)	0.0253 (3)
O1	0.7992 (4)	0.0463 (3)	0.43207 (17)	0.0234 (7)
O2	0.7940 (4)	0.2574 (3)	0.20886 (18)	0.0285 (8)
O3	0.6320 (5)	0.3131 (3)	0.30365 (19)	0.0340 (8)
O4	1.0056 (5)	0.3653 (3)	0.5448 (2)	0.0343 (8)
C1	0.8593 (6)	0.2142 (4)	0.4747 (3)	0.0210 (9)
C2	0.7987 (6)	0.1252 (4)	0.5400 (3)	0.0193 (9)
C3	0.7743 (6)	0.1181 (4)	0.6187 (3)	0.0217 (10)
H3	0.8012	0.1827	0.6411	0.026*
C4	0.7085 (6)	0.0108 (4)	0.6616 (3)	0.0226 (10)
C5	0.6671 (6)	−0.0880 (4)	0.6299 (3)	0.0249 (10)
H5	0.6212	−0.1579	0.6614	0.030*
C6	0.6938 (6)	−0.0833 (4)	0.5515 (3)	0.0260 (10)
C7	0.7615 (5)	0.0234 (4)	0.5097 (2)	0.0192 (9)
C8	0.8613 (6)	0.1634 (4)	0.4126 (3)	0.0236 (10)
C9	0.9133 (6)	0.2074 (5)	0.3309 (3)	0.0304 (12)
H9A	0.9629	0.1393	0.3109	0.037*
H9B	1.0056	0.2669	0.3274	0.037*
C10	0.7613 (6)	0.2650 (4)	0.2812 (3)	0.0229 (10)
C11	0.6621 (7)	0.3127 (5)	0.1547 (3)	0.0333 (12)
H11A	0.5579	0.2640	0.1625	0.050*
H11B	0.7086	0.3177	0.1034	0.050*
H11C	0.6319	0.3933	0.1621	0.050*
C12	0.6516 (7)	−0.1891 (5)	0.5159 (3)	0.0331 (12)
H12A	0.5628	−0.1639	0.4781	0.050*
H12B	0.6079	−0.2550	0.5550	0.050*
H12C	0.7571	−0.2158	0.4920	0.050*
C13	0.7001 (7)	0.4299 (5)	0.4797 (4)	0.0403 (14)
H13A	0.6444	0.3883	0.5267	0.060*
H13B	0.6317	0.4198	0.4371	0.060*
H13C	0.7069	0.5151	0.4798	0.060*
I2	1.27204 (4)	0.47039 (3)	0.246411 (19)	0.02932 (10)
S2	0.68848 (15)	0.62050 (11)	−0.02104 (6)	0.0208 (2)
O5	0.5483 (4)	0.7323 (3)	0.16778 (17)	0.0228 (7)
O6	0.2057 (4)	0.9129 (3)	−0.0229 (2)	0.0348 (9)
O7	0.5006 (4)	0.8964 (3)	−0.04426 (19)	0.0307 (8)
O8	0.7522 (4)	0.4897 (3)	−0.01091 (18)	0.0288 (8)
C14	0.6717 (6)	0.6561 (4)	0.0710 (2)	0.0192 (9)
C15	0.7950 (6)	0.6310 (4)	0.1331 (2)	0.0201 (9)
C16	0.9597 (6)	0.5710 (4)	0.1474 (3)	0.0226 (10)
H16	1.0203	0.5374	0.1103	0.027*
C17	1.0283 (6)	0.5640 (4)	0.2189 (3)	0.0241 (10)
C18	0.9410 (7)	0.6153 (4)	0.2756 (3)	0.0287 (11)
H18	0.9940	0.6092	0.3227	0.034*
C19	0.7787 (7)	0.6744 (5)	0.2632 (3)	0.0291 (11)
C20	0.7105 (6)	0.6795 (4)	0.1915 (3)	0.0221 (10)
C21	0.5275 (6)	0.7141 (4)	0.0946 (2)	0.0189 (9)
C22	0.3549 (6)	0.7575 (4)	0.0601 (3)	0.0232 (10)
H22A	0.2778	0.7819	0.0991	0.028*
H22B	0.3000	0.6902	0.0442	0.028*
C23	0.3682 (6)	0.8633 (4)	−0.0081 (3)	0.0215 (10)
C24	0.1942 (8)	1.0119 (5)	−0.0898 (3)	0.0457 (15)
H24A	0.2691	1.0767	−0.0837	0.069*
H24B	0.0737	1.0418	−0.0953	0.069*
H24C	0.2322	0.9828	−0.1347	0.069*
C25	0.6774 (8)	0.7295 (6)	0.3224 (3)	0.0482 (16)
H25A	0.7436	0.7163	0.3686	0.072*
H25B	0.5643	0.6917	0.3333	0.072*
H25C	0.6600	0.8155	0.3031	0.072*
C26	0.8772 (6)	0.7101 (5)	−0.0563 (3)	0.0284 (11)
H26A	0.9763	0.6818	−0.0243	0.043*
H26B	0.8507	0.7941	−0.0556	0.043*
H26C	0.9061	0.7024	−0.1079	0.043*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0579 (3)	0.0384 (2)	0.02000 (17)	0.01037 (17)	0.00379 (15)	−0.00193 (14)
S1	0.0221 (6)	0.0216 (6)	0.0315 (6)	−0.0007 (5)	−0.0032 (5)	−0.0038 (5)
O1	0.0225 (16)	0.0297 (18)	0.0195 (16)	0.0001 (14)	−0.0032 (13)	−0.0085 (14)
O2	0.0289 (18)	0.038 (2)	0.0172 (16)	0.0048 (15)	−0.0014 (14)	−0.0026 (14)
O3	0.0275 (19)	0.045 (2)	0.0254 (18)	0.0095 (16)	0.0018 (15)	−0.0014 (16)
O4	0.040 (2)	0.030 (2)	0.0317 (19)	−0.0043 (16)	−0.0048 (16)	−0.0033 (16)
C1	0.019 (2)	0.020 (2)	0.024 (2)	−0.0017 (18)	−0.0020 (18)	−0.0055 (19)
C2	0.016 (2)	0.017 (2)	0.024 (2)	0.0020 (17)	−0.0005 (17)	−0.0028 (18)
C3	0.024 (2)	0.021 (2)	0.021 (2)	0.0042 (18)	−0.0073 (18)	−0.0058 (18)
C4	0.020 (2)	0.029 (3)	0.020 (2)	0.0078 (19)	−0.0036 (18)	−0.0077 (19)
C5	0.022 (2)	0.018 (2)	0.032 (3)	0.0036 (18)	0.0000 (19)	−0.0002 (19)
C6	0.018 (2)	0.023 (2)	0.038 (3)	0.0060 (19)	−0.005 (2)	−0.009 (2)
C7	0.014 (2)	0.028 (2)	0.016 (2)	0.0004 (18)	−0.0050 (16)	−0.0048 (18)
C8	0.016 (2)	0.025 (2)	0.028 (2)	0.0031 (18)	−0.0052 (18)	−0.001 (2)
C9	0.021 (2)	0.048 (3)	0.020 (2)	0.005 (2)	0.0014 (19)	−0.002 (2)
C10	0.018 (2)	0.027 (3)	0.021 (2)	−0.0007 (19)	−0.0011 (18)	0.0006 (19)
C11	0.032 (3)	0.044 (3)	0.021 (2)	0.001 (2)	−0.005 (2)	−0.002 (2)
C12	0.026 (3)	0.028 (3)	0.048 (3)	0.001 (2)	−0.004 (2)	−0.015 (2)
C13	0.022 (3)	0.023 (3)	0.075 (4)	0.002 (2)	−0.007 (3)	−0.010 (3)
I2	0.02201 (16)	0.03174 (19)	0.03059 (18)	0.00357 (13)	−0.00415 (13)	0.00141 (14)
S2	0.0241 (6)	0.0247 (6)	0.0145 (5)	0.0012 (5)	−0.0013 (4)	−0.0061 (4)
O5	0.0260 (17)	0.0245 (17)	0.0187 (16)	0.0080 (13)	−0.0023 (13)	−0.0074 (13)
O6	0.0237 (18)	0.032 (2)	0.043 (2)	0.0059 (15)	−0.0063 (16)	0.0050 (16)
O7	0.0295 (19)	0.033 (2)	0.0262 (18)	0.0012 (15)	0.0048 (15)	0.0008 (15)
O8	0.037 (2)	0.0257 (18)	0.0240 (17)	0.0027 (15)	0.0050 (15)	−0.0080 (14)
C14	0.022 (2)	0.020 (2)	0.015 (2)	−0.0008 (18)	0.0016 (17)	−0.0042 (17)
C15	0.026 (2)	0.019 (2)	0.016 (2)	−0.0026 (18)	0.0017 (18)	−0.0044 (17)
C16	0.024 (2)	0.023 (2)	0.020 (2)	0.0008 (19)	0.0015 (18)	−0.0059 (19)
C17	0.022 (2)	0.020 (2)	0.027 (2)	0.0006 (19)	−0.0035 (19)	0.0011 (19)
C18	0.036 (3)	0.030 (3)	0.020 (2)	0.004 (2)	−0.011 (2)	−0.005 (2)
C19	0.041 (3)	0.031 (3)	0.016 (2)	0.010 (2)	−0.006 (2)	−0.009 (2)
C20	0.027 (2)	0.020 (2)	0.018 (2)	0.0035 (19)	−0.0024 (18)	−0.0028 (18)
C21	0.024 (2)	0.019 (2)	0.014 (2)	−0.0021 (18)	−0.0015 (17)	−0.0018 (17)
C22	0.022 (2)	0.030 (3)	0.017 (2)	−0.0006 (19)	0.0015 (18)	−0.0037 (19)
C23	0.027 (2)	0.015 (2)	0.026 (2)	0.0066 (19)	0.001 (2)	−0.0125 (19)
C24	0.037 (3)	0.038 (3)	0.053 (4)	0.011 (3)	−0.011 (3)	0.011 (3)
C25	0.057 (4)	0.066 (4)	0.027 (3)	0.029 (3)	−0.011 (3)	−0.023 (3)
C26	0.031 (3)	0.032 (3)	0.021 (2)	−0.004 (2)	0.008 (2)	−0.002 (2)

Geometric parameters (Å, º) top

I1—C4	2.103 (4)	I2—C17	2.108 (4)
I1—O7ⁱ	3.300 (3)	I2—O3ⁱⁱⁱ	3.264 (3)
S1—O4	1.482 (4)	S2—O8	1.505 (3)
S1—C1	1.773 (5)	S2—C14	1.771 (4)
S1—C13	1.800 (5)	S2—C26	1.786 (5)
S1—O4ⁱⁱ	3.025 (4)	O5—C21	1.379 (5)
O1—C7	1.375 (5)	O5—C20	1.382 (5)
O1—C8	1.378 (6)	O6—C23	1.341 (5)
O2—C10	1.326 (6)	O6—C24	1.451 (6)
O2—C11	1.442 (6)	O7—C23	1.196 (5)
O3—C10	1.198 (5)	C14—C21	1.351 (6)
C1—C8	1.349 (6)	C14—C15	1.446 (6)
C1—C2	1.435 (6)	C15—C20	1.400 (6)
C2—C3	1.397 (6)	C15—C16	1.400 (6)
C2—C7	1.403 (6)	C16—C17	1.379 (6)
C3—C4	1.378 (6)	C16—H16	0.9300
C3—H3	0.9300	C17—C18	1.403 (7)
C4—C5	1.395 (7)	C18—C19	1.376 (7)
C5—C6	1.397 (7)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.385 (6)
C6—C7	1.371 (7)	C19—C25	1.509 (7)
C6—C12	1.507 (7)	C21—C22	1.482 (6)
C8—C9	1.481 (6)	C22—C23	1.511 (6)
C9—C10	1.516 (6)	C22—H22A	0.9700
C9—H9A	0.9700	C22—H22B	0.9700
C9—H9B	0.9700	C24—H24A	0.9600
C11—H11A	0.9600	C24—H24B	0.9600
C11—H11B	0.9600	C24—H24C	0.9600
C11—H11C	0.9600	C25—H25A	0.9600
C12—H12A	0.9600	C25—H25B	0.9600
C12—H12B	0.9600	C25—H25C	0.9600
C12—H12C	0.9600	C26—H26A	0.9600
C13—H13A	0.9600	C26—H26B	0.9600
C13—H13B	0.9600	C26—H26C	0.9600
C13—H13C	0.9600

I1···O7ⁱ	3.300 (3)	I2···O3ⁱⁱⁱ	3.264 (3)

C4—I1—O7ⁱ	160.08 (15)	H13B—C13—H13C	109.5
O4—S1—C1	105.7 (2)	C17—I2—O3ⁱⁱⁱ	174.78 (14)
O4—S1—C13	106.0 (3)	O8—S2—C14	107.7 (2)
C1—S1—C13	97.4 (2)	O8—S2—C26	105.5 (2)
O4—S1—O4ⁱⁱ	78.94 (17)	C14—S2—C26	97.6 (2)
C1—S1—O4ⁱⁱ	174.59 (17)	C21—O5—C20	106.4 (3)
C13—S1—O4ⁱⁱ	78.48 (18)	C23—O6—C24	115.7 (4)
C7—O1—C8	106.4 (3)	C21—C14—C15	107.9 (4)
C10—O2—C11	116.0 (4)	C21—C14—S2	122.2 (3)
C8—C1—C2	108.3 (4)	C15—C14—S2	130.0 (3)
C8—C1—S1	123.4 (4)	C20—C15—C16	118.7 (4)
C2—C1—S1	128.3 (3)	C20—C15—C14	104.4 (4)
C3—C2—C7	119.1 (4)	C16—C15—C14	136.8 (4)
C3—C2—C1	136.7 (4)	C17—C16—C15	117.0 (4)
C7—C2—C1	104.2 (4)	C17—C16—H16	121.5
C4—C3—C2	116.8 (4)	C15—C16—H16	121.5
C4—C3—H3	121.6	C16—C17—C18	122.7 (4)
C2—C3—H3	121.6	C16—C17—I2	119.5 (3)
C3—C4—C5	123.2 (4)	C18—C17—I2	117.8 (3)
C3—C4—I1	119.8 (3)	C19—C18—C17	121.4 (4)
C5—C4—I1	117.1 (3)	C19—C18—H18	119.3
C4—C5—C6	120.7 (4)	C17—C18—H18	119.3
C4—C5—H5	119.6	C18—C19—C20	115.2 (4)
C6—C5—H5	119.6	C18—C19—C25	123.8 (4)
C7—C6—C5	115.5 (4)	C20—C19—C25	121.0 (5)
C7—C6—C12	122.6 (5)	O5—C20—C19	124.6 (4)
C5—C6—C12	121.8 (5)	O5—C20—C15	110.5 (4)
C6—C7—O1	124.8 (4)	C19—C20—C15	124.9 (4)
C6—C7—C2	124.6 (4)	C14—C21—O5	110.8 (4)
O1—C7—C2	110.6 (4)	C14—C21—C22	134.1 (4)
C1—C8—O1	110.5 (4)	O5—C21—C22	115.1 (4)
C1—C8—C9	133.7 (5)	C21—C22—C23	114.2 (4)
O1—C8—C9	115.8 (4)	C21—C22—H22A	108.7
C8—C9—C10	113.7 (4)	C23—C22—H22A	108.7
C8—C9—H9A	108.8	C21—C22—H22B	108.7
C10—C9—H9A	108.8	C23—C22—H22B	108.7
C8—C9—H9B	108.8	H22A—C22—H22B	107.6
C10—C9—H9B	108.8	O7—C23—O6	125.1 (4)
H9A—C9—H9B	107.7	O7—C23—C22	126.0 (4)
O3—C10—O2	124.9 (4)	O6—C23—C22	108.8 (4)
O3—C10—C9	124.9 (4)	O6—C24—H24A	109.5
O2—C10—C9	110.2 (4)	O6—C24—H24B	109.5
O2—C11—H11A	109.5	H24A—C24—H24B	109.5
O2—C11—H11B	109.5	O6—C24—H24C	109.5
H11A—C11—H11B	109.5	H24A—C24—H24C	109.5
O2—C11—H11C	109.5	H24B—C24—H24C	109.5
H11A—C11—H11C	109.5	C19—C25—H25A	109.5
H11B—C11—H11C	109.5	C19—C25—H25B	109.5
C6—C12—H12A	109.5	H25A—C25—H25B	109.5
C6—C12—H12B	109.5	C19—C25—H25C	109.5
H12A—C12—H12B	109.5	H25A—C25—H25C	109.5
C6—C12—H12C	109.5	H25B—C25—H25C	109.5
H12A—C12—H12C	109.5	S2—C26—H26A	109.5
H12B—C12—H12C	109.5	S2—C26—H26B	109.5
S1—C13—H13A	109.5	H26A—C26—H26B	109.5
S1—C13—H13B	109.5	S2—C26—H26C	109.5
H13A—C13—H13B	109.5	H26A—C26—H26C	109.5
S1—C13—H13C	109.5	H26B—C26—H26C	109.5
H13A—C13—H13C	109.5

O4—S1—C1—C8	−146.0 (4)	C8—C9—C10—O2	−155.0 (4)
C13—S1—C1—C8	105.1 (4)	O8—S2—C14—C21	−133.1 (4)
O4—S1—C1—C2	35.0 (5)	C26—S2—C14—C21	117.9 (4)
C13—S1—C1—C2	−74.0 (5)	O8—S2—C14—C15	45.9 (5)
C8—C1—C2—C3	176.9 (5)	C26—S2—C14—C15	−63.1 (5)
S1—C1—C2—C3	−4.0 (8)	C21—C14—C15—C20	−0.5 (5)
C8—C1—C2—C7	−2.0 (5)	S2—C14—C15—C20	−179.6 (4)
S1—C1—C2—C7	177.2 (3)	C21—C14—C15—C16	176.6 (5)
C7—C2—C3—C4	−2.1 (6)	S2—C14—C15—C16	−2.5 (8)
C1—C2—C3—C4	179.2 (5)	C20—C15—C16—C17	−0.1 (6)
C2—C3—C4—C5	0.1 (7)	C14—C15—C16—C17	−176.9 (5)
C2—C3—C4—I1	179.4 (3)	C15—C16—C17—C18	−0.9 (7)
O7ⁱ—I1—C4—C3	150.8 (3)	C15—C16—C17—I2	178.1 (3)
O7ⁱ—I1—C4—C5	−29.9 (6)	C16—C17—C18—C19	1.1 (8)
C3—C4—C5—C6	1.0 (7)	I2—C17—C18—C19	−177.9 (4)
I1—C4—C5—C6	−178.2 (3)	C17—C18—C19—C20	−0.3 (7)
C4—C5—C6—C7	−0.1 (6)	C17—C18—C19—C25	179.0 (5)
C4—C5—C6—C12	179.5 (4)	C21—O5—C20—C19	−177.8 (5)
C5—C6—C7—O1	179.3 (4)	C21—O5—C20—C15	1.7 (5)
C12—C6—C7—O1	−0.3 (7)	C18—C19—C20—O5	178.6 (4)
C5—C6—C7—C2	−2.0 (7)	C25—C19—C20—O5	−0.6 (8)
C12—C6—C7—C2	178.4 (4)	C18—C19—C20—C15	−0.7 (8)
C8—O1—C7—C6	179.0 (4)	C25—C19—C20—C15	−180.0 (5)
C8—O1—C7—C2	0.1 (5)	C16—C15—C20—O5	−178.5 (4)
C3—C2—C7—C6	3.2 (7)	C14—C15—C20—O5	−0.7 (5)
C1—C2—C7—C6	−177.7 (4)	C16—C15—C20—C19	0.9 (7)
C3—C2—C7—O1	−178.0 (4)	C14—C15—C20—C19	178.7 (5)
C1—C2—C7—O1	1.1 (5)	C15—C14—C21—O5	1.6 (5)
C2—C1—C8—O1	2.2 (5)	S2—C14—C21—O5	−179.2 (3)
S1—C1—C8—O1	−177.0 (3)	C15—C14—C21—C22	−176.3 (5)
C2—C1—C8—C9	−178.5 (5)	S2—C14—C21—C22	2.9 (7)
S1—C1—C8—C9	2.3 (8)	C20—O5—C21—C14	−2.0 (5)
C7—O1—C8—C1	−1.4 (5)	C20—O5—C21—C22	176.3 (4)
C7—O1—C8—C9	179.1 (4)	C14—C21—C22—C23	−68.7 (7)
C1—C8—C9—C10	−92.0 (6)	O5—C21—C22—C23	113.6 (4)
O1—C8—C9—C10	87.3 (5)	C24—O6—C23—O7	1.9 (7)
C11—O2—C10—O3	0.4 (7)	C24—O6—C23—C22	−176.7 (4)
C11—O2—C10—C9	−177.9 (4)	C21—C22—C23—O7	15.9 (7)
C8—C9—C10—O3	26.6 (7)	C21—C22—C23—O6	−165.5 (4)

Symmetry codes: (i) x, y−1, z+1; (ii) −x+2, −y+1, −z+1; (iii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3^iv	0.93	2.59	3.430 (6)	150
C11—H11B···O8	0.96	2.51	3.254 (6)	134
C12—H12C···O4^v	0.96	2.58	3.489 (6)	158
C16—H16···O8^vi	0.93	2.48	3.373 (6)	160
C18—H18···O4ⁱⁱ	0.93	2.44	3.297 (6)	153
C22—H22B···O8^vii	0.97	2.27	3.215 (6)	164
C12—H12A···Cg1^iv	0.96	2.85	3.734 (7)	153
C24—H24A···Cg3^viii	0.96	2.73	3.574 (7)	147

Symmetry codes: (ii) −x+2, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x+2, −y, −z+1; (vi) −x+2, −y+1, −z; (vii) −x+1, −y+1, −z; (viii) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₃IO₄S
M_r	392.19
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.5424 (4), 11.2177 (6), 17.845 (1)
α, β, γ (°)	77.701 (1), 88.074 (1), 88.229 (1)
V (Å³)	1473.92 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.32
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.574, 0.790
No. of measured, independent and observed [I > 2σ(I)] reflections	12617, 6248, 5328
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.088, 1.18
No. of reflections	6248
No. of parameters	349
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.15, −1.46

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Selected interatomic distances (Å) top

I1···O7ⁱ

3.300 (3)

I2···O3ⁱⁱ

3.264 (3)

Symmetry codes: (i) x, y−1, z+1; (ii) x+1, y, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱⁱⁱ	0.93	2.59	3.430 (6)	149.8
C11—H11B···O8	0.96	2.51	3.254 (6)	134.1
C12—H12C···O4^iv	0.96	2.58	3.489 (6)	158.2
C16—H16···O8^v	0.93	2.48	3.373 (6)	159.8
C18—H18···O4^vi	0.93	2.44	3.297 (6)	152.7
C22—H22B···O8^vii	0.97	2.27	3.215 (6)	164.3
C12—H12A···Cg1ⁱⁱⁱ	0.96	2.85	3.734 (7)	153.3
C24—H24A···Cg3^viii	0.96	2.73	3.574 (7)	146.5

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.

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o2384. Web of Science CSD CrossRef IUCr Journals Google Scholar
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o2431. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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