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Acta Cryst. (2009). E65, o1240    [ doi:10.1107/S1600536809016298 ]

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

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

Abstract top

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 [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.

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···Cg2ix 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···Cg3viii, 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···O4xi and O4···S1xi 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; Rf = 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+].

Refinement top

All H atoms were geometrically positioned and refined using a riding model, with C—H = 0.93 Å for the aryl, 0.97 Å for the methylene, and 0.96 Å for the methyl H atoms. Uiso(H) = 1.2Ueq(C) for the aryl and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.

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
[Figure 1] Fig. 1. The molecular structure of the title compound, showing displacement ellipsoids drawn at the 30% probability level.
[Figure 2] 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.]
[Figure 3] 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
C13H13IO4SZ = 4
Mr = 392.19F000 = 768
Triclinic, P1Dx = 1.767 Mg m−3
Hall symbol: -p 1Mo Kα radiation
λ = 0.71073 Å
a = 7.5424 (4) ÅCell parameters from 6307 reflections
b = 11.2177 (6) Åθ = 2.3–28.2º
c = 17.845 (1) ŵ = 2.32 mm−1
α = 77.701 (1)ºT = 293 K
β = 88.074 (1)ºBlock, colorless
γ = 88.229 (1)º0.30 × 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 tube5328 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
Detector resolution: 10.0 pixels mm-1θmax = 27.0º
T = 293 Kθmin = 1.9º
φ and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)		k = −14→14
Tmin = 0.574, Tmax = 0.790l = −22→22
12617 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050H-atom parameters constrained
wR(F2) = 0.088  w = 1/[σ2(Fo2) + (0.0184P)2 + 4.3135P]
where P = (Fo2 + 2Fc2)/3
S = 1.18(Δ/σ)max < 0.001
6248 reflectionsΔρmax = 1.15 e Å−3
349 parametersΔρmin = −1.46 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C13H13IO4Sγ = 88.229 (1)º
Mr = 392.19V = 1473.92 (14) Å3
Triclinic, P1Z = 4
a = 7.5424 (4) ÅMo Kα
b = 11.2177 (6) ŵ = 2.32 mm−1
c = 17.845 (1) ÅT = 293 K
α = 77.701 (1)º0.30 × 0.20 × 0.10 mm
β = 88.074 (1)º
Data collection top
Bruker SMART CCD
diffractometer		6248 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)		5328 reflections with I > 2σ(I)
Tmin = 0.574, Tmax = 0.790Rint = 0.027
12617 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.050349 parameters
wR(F2) = 0.088H-atom parameters constrained
S = 1.18Δρmax = 1.15 e Å−3
6248 reflectionsΔρmin = −1.46 e Å−3
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
xyzUiso*/Ueq
I10.66948 (5)−0.00958 (3)0.780861 (19)0.03974 (11)
S10.92033 (15)0.36686 (11)0.47095 (7)0.0253 (3)
O10.7992 (4)0.0463 (3)0.43207 (17)0.0234 (7)
O20.7940 (4)0.2574 (3)0.20886 (18)0.0285 (8)
O30.6320 (5)0.3131 (3)0.30365 (19)0.0340 (8)
O41.0056 (5)0.3653 (3)0.5448 (2)0.0343 (8)
C10.8593 (6)0.2142 (4)0.4747 (3)0.0210 (9)
C20.7987 (6)0.1252 (4)0.5400 (3)0.0193 (9)
C30.7743 (6)0.1181 (4)0.6187 (3)0.0217 (10)
H30.80120.18270.64110.026*
C40.7085 (6)0.0108 (4)0.6616 (3)0.0226 (10)
C50.6671 (6)−0.0880 (4)0.6299 (3)0.0249 (10)
H50.6212−0.15790.66140.030*
C60.6938 (6)−0.0833 (4)0.5515 (3)0.0260 (10)
C70.7615 (5)0.0234 (4)0.5097 (2)0.0192 (9)
C80.8613 (6)0.1634 (4)0.4126 (3)0.0236 (10)
C90.9133 (6)0.2074 (5)0.3309 (3)0.0304 (12)
H9A0.96290.13930.31090.037*
H9B1.00560.26690.32740.037*
C100.7613 (6)0.2650 (4)0.2812 (3)0.0229 (10)
C110.6621 (7)0.3127 (5)0.1547 (3)0.0333 (12)
H11A0.55790.26400.16250.050*
H11B0.70860.31770.10340.050*
H11C0.63190.39330.16210.050*
C120.6516 (7)−0.1891 (5)0.5159 (3)0.0331 (12)
H12A0.5628−0.16390.47810.050*
H12B0.6079−0.25500.55500.050*
H12C0.7571−0.21580.49200.050*
C130.7001 (7)0.4299 (5)0.4797 (4)0.0403 (14)
H13A0.64440.38830.52670.060*
H13B0.63170.41980.43710.060*
H13C0.70690.51510.47980.060*
I21.27204 (4)0.47039 (3)0.246411 (19)0.02932 (10)
S20.68848 (15)0.62050 (11)−0.02104 (6)0.0208 (2)
O50.5483 (4)0.7323 (3)0.16778 (17)0.0228 (7)
O60.2057 (4)0.9129 (3)−0.0229 (2)0.0348 (9)
O70.5006 (4)0.8964 (3)−0.04426 (19)0.0307 (8)
O80.7522 (4)0.4897 (3)−0.01091 (18)0.0288 (8)
C140.6717 (6)0.6561 (4)0.0710 (2)0.0192 (9)
C150.7950 (6)0.6310 (4)0.1331 (2)0.0201 (9)
C160.9597 (6)0.5710 (4)0.1474 (3)0.0226 (10)
H161.02030.53740.11030.027*
C171.0283 (6)0.5640 (4)0.2189 (3)0.0241 (10)
C180.9410 (7)0.6153 (4)0.2756 (3)0.0287 (11)
H180.99400.60920.32270.034*
C190.7787 (7)0.6744 (5)0.2632 (3)0.0291 (11)
C200.7105 (6)0.6795 (4)0.1915 (3)0.0221 (10)
C210.5275 (6)0.7141 (4)0.0946 (2)0.0189 (9)
C220.3549 (6)0.7575 (4)0.0601 (3)0.0232 (10)
H22A0.27780.78190.09910.028*
H22B0.30000.69020.04420.028*
C230.3682 (6)0.8633 (4)−0.0081 (3)0.0215 (10)
C240.1942 (8)1.0119 (5)−0.0898 (3)0.0457 (15)
H24A0.26911.0767−0.08370.069*
H24B0.07371.0418−0.09530.069*
H24C0.23220.9828−0.13470.069*
C250.6774 (8)0.7295 (6)0.3224 (3)0.0482 (16)
H25A0.74360.71630.36860.072*
H25B0.56430.69170.33330.072*
H25C0.66000.81550.30310.072*
C260.8772 (6)0.7101 (5)−0.0563 (3)0.0284 (11)
H26A0.97630.6818−0.02430.043*
H26B0.85070.7941−0.05560.043*
H26C0.90610.7024−0.10790.043*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I10.0579 (3)0.0384 (2)0.02000 (17)0.01037 (17)0.00379 (15)−0.00193 (14)
S10.0221 (6)0.0216 (6)0.0315 (6)−0.0007 (5)−0.0032 (5)−0.0038 (5)
O10.0225 (16)0.0297 (18)0.0195 (16)0.0001 (14)−0.0032 (13)−0.0085 (14)
O20.0289 (18)0.038 (2)0.0172 (16)0.0048 (15)−0.0014 (14)−0.0026 (14)
O30.0275 (19)0.045 (2)0.0254 (18)0.0095 (16)0.0018 (15)−0.0014 (16)
O40.040 (2)0.030 (2)0.0317 (19)−0.0043 (16)−0.0048 (16)−0.0033 (16)
C10.019 (2)0.020 (2)0.024 (2)−0.0017 (18)−0.0020 (18)−0.0055 (19)
C20.016 (2)0.017 (2)0.024 (2)0.0020 (17)−0.0005 (17)−0.0028 (18)
C30.024 (2)0.021 (2)0.021 (2)0.0042 (18)−0.0073 (18)−0.0058 (18)
C40.020 (2)0.029 (3)0.020 (2)0.0078 (19)−0.0036 (18)−0.0077 (19)
C50.022 (2)0.018 (2)0.032 (3)0.0036 (18)0.0000 (19)−0.0002 (19)
C60.018 (2)0.023 (2)0.038 (3)0.0060 (19)−0.005 (2)−0.009 (2)
C70.014 (2)0.028 (2)0.016 (2)0.0004 (18)−0.0050 (16)−0.0048 (18)
C80.016 (2)0.025 (2)0.028 (2)0.0031 (18)−0.0052 (18)−0.001 (2)
C90.021 (2)0.048 (3)0.020 (2)0.005 (2)0.0014 (19)−0.002 (2)
C100.018 (2)0.027 (3)0.021 (2)−0.0007 (19)−0.0011 (18)0.0006 (19)
C110.032 (3)0.044 (3)0.021 (2)0.001 (2)−0.005 (2)−0.002 (2)
C120.026 (3)0.028 (3)0.048 (3)0.001 (2)−0.004 (2)−0.015 (2)
C130.022 (3)0.023 (3)0.075 (4)0.002 (2)−0.007 (3)−0.010 (3)
I20.02201 (16)0.03174 (19)0.03059 (18)0.00357 (13)−0.00415 (13)0.00141 (14)
S20.0241 (6)0.0247 (6)0.0145 (5)0.0012 (5)−0.0013 (4)−0.0061 (4)
O50.0260 (17)0.0245 (17)0.0187 (16)0.0080 (13)−0.0023 (13)−0.0074 (13)
O60.0237 (18)0.032 (2)0.043 (2)0.0059 (15)−0.0063 (16)0.0050 (16)
O70.0295 (19)0.033 (2)0.0262 (18)0.0012 (15)0.0048 (15)0.0008 (15)
O80.037 (2)0.0257 (18)0.0240 (17)0.0027 (15)0.0050 (15)−0.0080 (14)
C140.022 (2)0.020 (2)0.015 (2)−0.0008 (18)0.0016 (17)−0.0042 (17)
C150.026 (2)0.019 (2)0.016 (2)−0.0026 (18)0.0017 (18)−0.0044 (17)
C160.024 (2)0.023 (2)0.020 (2)0.0008 (19)0.0015 (18)−0.0059 (19)
C170.022 (2)0.020 (2)0.027 (2)0.0006 (19)−0.0035 (19)0.0011 (19)
C180.036 (3)0.030 (3)0.020 (2)0.004 (2)−0.011 (2)−0.005 (2)
C190.041 (3)0.031 (3)0.016 (2)0.010 (2)−0.006 (2)−0.009 (2)
C200.027 (2)0.020 (2)0.018 (2)0.0035 (19)−0.0024 (18)−0.0028 (18)
C210.024 (2)0.019 (2)0.014 (2)−0.0021 (18)−0.0015 (17)−0.0018 (17)
C220.022 (2)0.030 (3)0.017 (2)−0.0006 (19)0.0015 (18)−0.0037 (19)
C230.027 (2)0.015 (2)0.026 (2)0.0066 (19)0.001 (2)−0.0125 (19)
C240.037 (3)0.038 (3)0.053 (4)0.011 (3)−0.011 (3)0.011 (3)
C250.057 (4)0.066 (4)0.027 (3)0.029 (3)−0.011 (3)−0.023 (3)
C260.031 (3)0.032 (3)0.021 (2)−0.004 (2)0.008 (2)−0.002 (2)
Geometric parameters (Å, °) top
I1—C42.103 (4)I2—C172.108 (4)
I1—O7i3.300 (3)I2—O3iii3.264 (3)
S1—O41.482 (4)S2—O81.505 (3)
S1—C11.773 (5)S2—C141.771 (4)
S1—C131.800 (5)S2—C261.786 (5)
S1—O4ii3.025 (4)O5—C211.379 (5)
O1—C71.375 (5)O5—C201.382 (5)
O1—C81.378 (6)O6—C231.341 (5)
O2—C101.326 (6)O6—C241.451 (6)
O2—C111.442 (6)O7—C231.196 (5)
O3—C101.198 (5)C14—C211.351 (6)
C1—C81.349 (6)C14—C151.446 (6)
C1—C21.435 (6)C15—C201.400 (6)
C2—C31.397 (6)C15—C161.400 (6)
C2—C71.403 (6)C16—C171.379 (6)
C3—C41.378 (6)C16—H160.9300
C3—H30.9300C17—C181.403 (7)
C4—C51.395 (7)C18—C191.376 (7)
C5—C61.397 (7)C18—H180.9300
C5—H50.9300C19—C201.385 (6)
C6—C71.371 (7)C19—C251.509 (7)
C6—C121.507 (7)C21—C221.482 (6)
C8—C91.481 (6)C22—C231.511 (6)
C9—C101.516 (6)C22—H22A0.9700
C9—H9A0.9700C22—H22B0.9700
C9—H9B0.9700C24—H24A0.9600
C11—H11A0.9600C24—H24B0.9600
C11—H11B0.9600C24—H24C0.9600
C11—H11C0.9600C25—H25A0.9600
C12—H12A0.9600C25—H25B0.9600
C12—H12B0.9600C25—H25C0.9600
C12—H12C0.9600C26—H26A0.9600
C13—H13A0.9600C26—H26B0.9600
C13—H13B0.9600C26—H26C0.9600
C13—H13C0.9600
I1···O7i3.300 (3)I2···O3iii3.264 (3)
C4—I1—O7i160.08 (15)H13B—C13—H13C109.5
O4—S1—C1105.7 (2)C17—I2—O3iii174.78 (14)
O4—S1—C13106.0 (3)O8—S2—C14107.7 (2)
C1—S1—C1397.4 (2)O8—S2—C26105.5 (2)
O4—S1—O4ii78.94 (17)C14—S2—C2697.6 (2)
C1—S1—O4ii174.59 (17)C21—O5—C20106.4 (3)
C13—S1—O4ii78.48 (18)C23—O6—C24115.7 (4)
C7—O1—C8106.4 (3)C21—C14—C15107.9 (4)
C10—O2—C11116.0 (4)C21—C14—S2122.2 (3)
C8—C1—C2108.3 (4)C15—C14—S2130.0 (3)
C8—C1—S1123.4 (4)C20—C15—C16118.7 (4)
C2—C1—S1128.3 (3)C20—C15—C14104.4 (4)
C3—C2—C7119.1 (4)C16—C15—C14136.8 (4)
C3—C2—C1136.7 (4)C17—C16—C15117.0 (4)
C7—C2—C1104.2 (4)C17—C16—H16121.5
C4—C3—C2116.8 (4)C15—C16—H16121.5
C4—C3—H3121.6C16—C17—C18122.7 (4)
C2—C3—H3121.6C16—C17—I2119.5 (3)
C3—C4—C5123.2 (4)C18—C17—I2117.8 (3)
C3—C4—I1119.8 (3)C19—C18—C17121.4 (4)
C5—C4—I1117.1 (3)C19—C18—H18119.3
C4—C5—C6120.7 (4)C17—C18—H18119.3
C4—C5—H5119.6C18—C19—C20115.2 (4)
C6—C5—H5119.6C18—C19—C25123.8 (4)
C7—C6—C5115.5 (4)C20—C19—C25121.0 (5)
C7—C6—C12122.6 (5)O5—C20—C19124.6 (4)
C5—C6—C12121.8 (5)O5—C20—C15110.5 (4)
C6—C7—O1124.8 (4)C19—C20—C15124.9 (4)
C6—C7—C2124.6 (4)C14—C21—O5110.8 (4)
O1—C7—C2110.6 (4)C14—C21—C22134.1 (4)
C1—C8—O1110.5 (4)O5—C21—C22115.1 (4)
C1—C8—C9133.7 (5)C21—C22—C23114.2 (4)
O1—C8—C9115.8 (4)C21—C22—H22A108.7
C8—C9—C10113.7 (4)C23—C22—H22A108.7
C8—C9—H9A108.8C21—C22—H22B108.7
C10—C9—H9A108.8C23—C22—H22B108.7
C8—C9—H9B108.8H22A—C22—H22B107.6
C10—C9—H9B108.8O7—C23—O6125.1 (4)
H9A—C9—H9B107.7O7—C23—C22126.0 (4)
O3—C10—O2124.9 (4)O6—C23—C22108.8 (4)
O3—C10—C9124.9 (4)O6—C24—H24A109.5
O2—C10—C9110.2 (4)O6—C24—H24B109.5
O2—C11—H11A109.5H24A—C24—H24B109.5
O2—C11—H11B109.5O6—C24—H24C109.5
H11A—C11—H11B109.5H24A—C24—H24C109.5
O2—C11—H11C109.5H24B—C24—H24C109.5
H11A—C11—H11C109.5C19—C25—H25A109.5
H11B—C11—H11C109.5C19—C25—H25B109.5
C6—C12—H12A109.5H25A—C25—H25B109.5
C6—C12—H12B109.5C19—C25—H25C109.5
H12A—C12—H12B109.5H25A—C25—H25C109.5
C6—C12—H12C109.5H25B—C25—H25C109.5
H12A—C12—H12C109.5S2—C26—H26A109.5
H12B—C12—H12C109.5S2—C26—H26B109.5
S1—C13—H13A109.5H26A—C26—H26B109.5
S1—C13—H13B109.5S2—C26—H26C109.5
H13A—C13—H13B109.5H26A—C26—H26C109.5
S1—C13—H13C109.5H26B—C26—H26C109.5
H13A—C13—H13C109.5
O4—S1—C1—C8−146.0 (4)C8—C9—C10—O2−155.0 (4)
C13—S1—C1—C8105.1 (4)O8—S2—C14—C21−133.1 (4)
O4—S1—C1—C235.0 (5)C26—S2—C14—C21117.9 (4)
C13—S1—C1—C2−74.0 (5)O8—S2—C14—C1545.9 (5)
C8—C1—C2—C3176.9 (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—C7177.2 (3)C21—C14—C15—C16176.6 (5)
C7—C2—C3—C4−2.1 (6)S2—C14—C15—C16−2.5 (8)
C1—C2—C3—C4179.2 (5)C20—C15—C16—C17−0.1 (6)
C2—C3—C4—C50.1 (7)C14—C15—C16—C17−176.9 (5)
C2—C3—C4—I1179.4 (3)C15—C16—C17—C18−0.9 (7)
O7i—I1—C4—C3150.8 (3)C15—C16—C17—I2178.1 (3)
O7i—I1—C4—C5−29.9 (6)C16—C17—C18—C191.1 (8)
C3—C4—C5—C61.0 (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—C25179.0 (5)
C4—C5—C6—C12179.5 (4)C21—O5—C20—C19−177.8 (5)
C5—C6—C7—O1179.3 (4)C21—O5—C20—C151.7 (5)
C12—C6—C7—O1−0.3 (7)C18—C19—C20—O5178.6 (4)
C5—C6—C7—C2−2.0 (7)C25—C19—C20—O5−0.6 (8)
C12—C6—C7—C2178.4 (4)C18—C19—C20—C15−0.7 (8)
C8—O1—C7—C6179.0 (4)C25—C19—C20—C15−180.0 (5)
C8—O1—C7—C20.1 (5)C16—C15—C20—O5−178.5 (4)
C3—C2—C7—C63.2 (7)C14—C15—C20—O5−0.7 (5)
C1—C2—C7—C6−177.7 (4)C16—C15—C20—C190.9 (7)
C3—C2—C7—O1−178.0 (4)C14—C15—C20—C19178.7 (5)
C1—C2—C7—O11.1 (5)C15—C14—C21—O51.6 (5)
C2—C1—C8—O12.2 (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—C222.9 (7)
S1—C1—C8—C92.3 (8)C20—O5—C21—C14−2.0 (5)
C7—O1—C8—C1−1.4 (5)C20—O5—C21—C22176.3 (4)
C7—O1—C8—C9179.1 (4)C14—C21—C22—C23−68.7 (7)
C1—C8—C9—C10−92.0 (6)O5—C21—C22—C23113.6 (4)
O1—C8—C9—C1087.3 (5)C24—O6—C23—O71.9 (7)
C11—O2—C10—O30.4 (7)C24—O6—C23—C22−176.7 (4)
C11—O2—C10—C9−177.9 (4)C21—C22—C23—O715.9 (7)
C8—C9—C10—O326.6 (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, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O3iv0.932.593.430 (6)150
C11—H11B···O80.962.513.254 (6)134
C12—H12C···O4v0.962.583.489 (6)158
C16—H16···O8vi0.932.483.373 (6)160
C18—H18···O4ii0.932.443.297 (6)153
C22—H22B···O8vii0.972.273.215 (6)164
C12—H12A···Cg1iv0.962.853.734 (7)153
C24—H24A···Cg3viii0.962.733.574 (7)147
Symmetry codes: (iv) −x+1, −y, −z+1; (v) −x+2, −y, −z+1; (vi) −x+2, −y+1, −z; (ii) −x+2, −y+1, −z+1; (vii) −x+1, −y+1, −z; (viii) −x+1, −y+2, −z.
Table 1
Selected geometric parameters (Å) top
I1···O7i3.300 (3)I2···O3ii3.264 (3)
Symmetry codes: (i) x, y−1, z+1; (ii) x+1, y, z.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O3iii0.932.593.430 (6)150
C11—H11B···O80.962.513.254 (6)134
C12—H12C···O4iv0.962.583.489 (6)158
C16—H16···O8v0.932.483.373 (6)160
C18—H18···O4vi0.932.443.297 (6)153
C22—H22B···O8vii0.972.273.215 (6)164
C12—H12A···Cg1iii0.962.853.734 (7)153
C24—H24A···Cg3viii0.962.733.574 (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.
Acknowledgements top

No Acknowledgements

references
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