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The structure of 2,5-bis­(methyl­thio)-1,4-benzo­quinone, C8H8O2S2, is composed of an essentially planar centrosymmetric benzo­quinone substituted with two methyl­thio groups. The important bond distances are S—Csp3 1.788 (2) and S—Csp2 1.724 (2) Å, and the two Csp2—Csp2 distances are 1.447 (3) and 1.504 (3) Å, which differ significantly. There are short S...S interactions of 3.430 (1) Å and Csp2—H...O-type contacts forming a dimeric motif with graph set R22(8). The structure of 2-methyl-3-(methyl­sulfonyl)­benzo­[b]­thio­phene, C10H10O2S2, is composed of an essentially planar benzo­thio­phene moiety substituted with methyl and methyl­sulfonyl groups. The mean values of the important bond distances are endocyclic S—Csp2 1.734 (3), S=O 1.434 (4) and C—Caromatic 1.389 (10) Å. The exocyclic S—Csp2 and S—Csp3 distances are 1.759 (4) and 1.763 (5) Å, respectively.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001402/bk1513sup1.cif
Contains datablocks Global, I, IV

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001402/bk1513Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001402/bk1513IVsup3.hkl
Contains datablock IV

CCDC references: 145537; 145538

Comment top

Recently, 2,5-bis(methylthio)-1,4-benzoquinone, (I), has been used to prepare sulfur-quinone polyurethane coatings which are applied to protect iron surfaces. Surprisingly, the synthesis of (I) was not reported until 1998 and then was obtained in only 15% yield by reaction of 1,4-benzoquinone with sodium thiomethoxide (Hu & Nikles, 1998). Using a clay-catalyzed one-step thioalkylation procedure developed in our laboratories (Clark et al., 1996), we have been able to make compound (I) in good yield and on a large scale. Conveniently, one half of the quinone reagent re-oxidizes the intermediate product to yield the product, (I) (scheme). 1H NMR analysis of (I), which is obtained from ethanol as brilliant red crystals, does not allow differentiation of (I) from its 2,3-bis(methylthio) isomer. X-ray analysis showed, however, that the clay-catalyzed synthesis reported herein yielded the 2,5-isomer as the sole product. \scheme

A one-step thioalkylation procedure developed in our laboratory allows addition of –SR groups to aromatics and heteroaromatics (Clark et al., 1996). However, it was clear that reaction of 2,3-methylbenzo[b]thiophene, (III), with dimethyl disulfide over a clay catalyst did not yield the expected 5,6-disubstituted product, but an oily compound in which one of either the 2- or 3-methyl groups had been replaced by an –SCH3 substituent (scheme). Since an ipso-substitution of this type is quite rare and because other spectroscopic methods could not differentiate whether substitution had occurred at the 2- or 3- positions, the product was oxidized to its crystalline sulfonyl derivative using a literature procedure (Aitken et al., 1994) and was subjected to X-ray crystallographic analysis. This analysis showed that the 3-thiomethyl derivative, (IV), had been produced, suggesting that a sulfur-assisted ipso-substitution had taken place.

The structure of (I) is composed of centrosymmetric molecules which are essentially planar [maximum deviation 0.026 (2) Å for C3]. The bond distances agree well with the corresponding values reported for bis-, tris- and tetrakis(thiophenyl)benzoquinones (Cambridge Structural Database; Allen & Kennard, 1993). The S—Csp3 and S—Csp2 bond distances of 1.788 (2) and 1.724 (2) Å, respectively, differ significantly. The bonds C3=O1 [1.227 (3) Å] and C1=C2 [1.353 (3) Å] are double bonds. The Csp2—Csp2 bonds, C1—C3i [1.504 (3) Å; symmetry code: (i) -x, -y, 1 - z] and C2—C3 [1.447 (3) Å], are in excellent agreement with the values reported for the thiophenylbenzoquinone structures mentioned above. The S1—C1—C3i angle of 112.85 (15)° is smaller than the value of 120° expected for a Csp2 C-atom, perhaps because of intermolecular methyl-methyl and methyl-carbonyl interactions.

The molecules of (I) pack in layers which lie perpendiular to the (101) plane. Within the layers there are short S···S interactions of 3.430 (1) Å between the molecules related by inversion centers. There are also short Csp2—H···O type contacts (H···O 2.56 Å and Csp2—H···O 164°) forming a dimeric motif with graph set R22(8) (Fig. 2); similar interactions in the crystal structures of quinones have been discussed by Bernstein et al. (1994).

The structure of (IV) is composed of discrete molecules separated by normal van der Waals distances. The benzothiophene moiety is essentially planar [maximum deviation 0.021 (4) Å for C5], with S2 and C9 of the methylsulfonyl and methyl groups lying 0.045 (5) and 0.022 (6) Å, respectively, on the same side of the plane. The intramolecular repulsion between the two substituents is relieved by the widening of the C2—C1—C9 angle to 132.5 (4)°. The important bond distances are endocyclic S—Csp2 (mean) 1.734 (3), exocyclic S—Csp2 1.759 (4), S—Csp3 1.763 (5), S=O (mean) 1.434 (4) and C—Caromatic (mean) 1.389 (10) Å.

Experimental top

A mixture of 1,4-benzoquinone (54 g, 0.5 mol), dimethyl disulfide (28.2 g, 0.3 mol) and montmorillonite K-10 (ex-Fluka) impregnated with 2 mmol g-1 ZnCl2 (50 g; Clark et al., 1996) in dichloromethane (500 ml) was stirred for 16 h at 293 K. Filtration of the reaction mixture afforded a red solid comprised of the clay catalyst and the product, (I). The filtrate contained a small amount of (I), excess dimethyl disulfide and the quinol, (II), formed during re-oxidation of the reaction intermediate. Soxhlet extraction of the red solid with dichloromethane over 20 h gave (I) as a red solid (34 g, 63%). Recrystallization from ethanol afforded red plates. Compound (IV) was prepared using K-10 montmorillonite clay and the method described previously by Clark et al. (1996), and was oxidized to its sulfonyl derivative using a method employed by Aitken et al. (1994). Crystals of (IV) were obtained by slow crystallization from aqueous ethanol.

Refinement top

For both compounds, H atoms were treated as riding, with default C—H distances and Uiso values. The absolute structure of compound (IV) could not be established in this analysis because no Friedel pairs were collected.

Computing details top

Data collection: CAD-4 Software (Enraf-Nonius, 1989) for (I); MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) for (IV). Cell refinement: CAD-4 Software for (I); MSC/AFC Diffractometer Control Software for (IV). For both compounds, data reduction: TEXSAN (Molecular Structure Corporation, 1994); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN; software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) drawing of (I) with the atomic numbering scheme. Displacement ellipsoids have been plotted at the 50% probability level and H atoms assigned arbitrary radii [symmetry code: (i) -x, -y, 1 - z].
[Figure 2] Fig. 2. The unit cell packing of (I) showing Csp2—H···O type contacts forming a dimeric motif.
[Figure 3] Fig. 3. ORTEPII (Johnson, 1976) drawing of (IV) with the atomic numbering scheme. Displacement ellipsoids have been plotted at the 50% probability level and H atoms assigned arbitrary radii.
(I) 2,5-Bis(methylthio)-1,4-benzoquinone top
Crystal data top
C8H8O2S2Z = 1
Mr = 200.26F(000) = 104
Triclinic, P1Dx = 1.525 Mg m3
a = 4.032 (2) ÅCu Kα radiation, λ = 1.54178 Å
b = 5.717 (1) ÅCell parameters from 25 reflections
c = 9.626 (1) Åθ = 10–20°
α = 86.04 (1)°µ = 5.17 mm1
β = 80.60 (2)°T = 293 K
γ = 86.09 (3)°Plate, red
V = 218.0 (1) Å30.36 × 0.28 × 0.08 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
757 reflections with I<2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.030
Graphite monochromatorθmax = 68.0°, θmin = 5.0°
ω–2θ scansh = 44
Absorption correction: empirical (using intensity measurements)
ψ-scan (3 reflections) (North et al., 1968)
k = 66
Tmin = 0.22, Tmax = 0.66l = 1111
1535 measured reflections3 standard reflections every 200 reflections
791 independent reflections intensity decay: <0.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.043H-atom parameters constrained
wR(F2) = 0.111 w = 1/[σ2(Fo2) + (0.0671P)2 + 0.0706P]
where P = (Fo2 + 2Fc2)/3
S = 1.15(Δ/σ)max < 0.001
791 reflectionsΔρmax = 0.39 e Å3
56 parametersΔρmin = 0.32 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.060 (10)
Crystal data top
C8H8O2S2γ = 86.09 (3)°
Mr = 200.26V = 218.0 (1) Å3
Triclinic, P1Z = 1
a = 4.032 (2) ÅCu Kα radiation
b = 5.717 (1) ŵ = 5.17 mm1
c = 9.626 (1) ÅT = 293 K
α = 86.04 (1)°0.36 × 0.28 × 0.08 mm
β = 80.60 (2)°
Data collection top
Enraf-Nonius CAD-4
diffractometer
757 reflections with I<2σ(I)
Absorption correction: empirical (using intensity measurements)
ψ-scan (3 reflections) (North et al., 1968)
Rint = 0.030
Tmin = 0.22, Tmax = 0.663 standard reflections every 200 reflections
1535 measured reflections intensity decay: <0.5%
791 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.111H-atom parameters constrained
S = 1.15Δρmax = 0.39 e Å3
791 reflectionsΔρmin = 0.32 e Å3
56 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.08707 (14)0.02197 (9)0.16908 (5)0.0402 (3)
O10.2593 (5)0.3313 (3)0.66402 (18)0.0496 (5)
C10.0574 (5)0.0295 (4)0.3500 (2)0.0313 (5)
C20.1864 (5)0.1979 (4)0.4351 (2)0.0349 (5)
H20.30730.32800.39550.042*
C30.1404 (5)0.1802 (4)0.5863 (2)0.0338 (5)
C40.2975 (7)0.2992 (4)0.1260 (3)0.0455 (6)
H4A0.51340.31050.15650.068*
H4B0.32740.31260.02580.068*
H4C0.16460.42340.17260.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0562 (5)0.0385 (4)0.0247 (4)0.0085 (3)0.0079 (3)0.0006 (2)
O10.0707 (12)0.0401 (9)0.0353 (9)0.0213 (8)0.0131 (8)0.0040 (7)
C10.0348 (10)0.0304 (10)0.0280 (10)0.0005 (8)0.0054 (8)0.0006 (8)
C20.0435 (11)0.0300 (10)0.0300 (11)0.0070 (8)0.0064 (9)0.0017 (8)
C30.0405 (11)0.0290 (11)0.0314 (11)0.0034 (8)0.0083 (8)0.0017 (8)
C40.0562 (14)0.0445 (13)0.0338 (12)0.0080 (10)0.0033 (10)0.0081 (10)
Geometric parameters (Å, º) top
S1—C11.724 (2)C1—C3i1.504 (3)
S1—C41.788 (2)C2—C31.447 (3)
O1—C31.227 (3)C3—C1i1.504 (3)
C1—C21.353 (3)
C1—S1—C4102.83 (11)C1—C2—C3121.5 (2)
C2—C1—C3i119.5 (2)O1—C3—C2121.8 (2)
C2—C1—S1127.68 (17)O1—C3—C1i119.1 (2)
C3i—C1—S1112.84 (15)C2—C3—C1i119.1 (2)
C4—S1—C1—C24.5 (2)S1—C1—C2—C3179.95 (16)
C4—S1—C1—C3i175.06 (15)C1—C2—C3—O1179.4 (2)
C3i—C1—C2—C30.4 (3)C1—C2—C3—C1i0.4 (3)
Symmetry code: (i) x, y, z+1.
(IV) 2-Methyl-3-(methylsulfonyl)benzo[b]thiophene top
Crystal data top
C10H10O2S2F(000) = 236
Mr = 226.30Dx = 1.454 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71069 Å
a = 5.8228 (5) ÅCell parameters from 25 reflections
b = 10.440 (1) Åθ = 10–20°
c = 8.6217 (9) ŵ = 0.48 mm1
β = 99.57 (1)°T = 293 K
V = 516.8 (1) Å3Prismatic, colorless
Z = 20.55 × 0.38 × 0.35 mm
Data collection top
Rigaku-AFC-6S
diffractometer
1063 reflections with I<2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 27.6°, θmin = 2.4°
ω/2θ scansh = 07
Absorption correction: empirical (using intensity measurements)
via ψ-scan (3 reflections) (North et al., 1968)
k = 013
Tmin = 0.78, Tmax = 0.85l = 1111
1385 measured reflections3 standard reflections every 200 reflections
1268 independent reflections intensity decay: 1.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.109 w = 1/[σ2(Fo2) + (0.0656P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.19(Δ/σ)max < 0.001
1268 reflectionsΔρmax = 0.23 e Å3
128 parametersΔρmin = 0.29 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.07 (15)
Crystal data top
C10H10O2S2V = 516.8 (1) Å3
Mr = 226.30Z = 2
Monoclinic, P21Mo Kα radiation
a = 5.8228 (5) ŵ = 0.48 mm1
b = 10.440 (1) ÅT = 293 K
c = 8.6217 (9) Å0.55 × 0.38 × 0.35 mm
β = 99.57 (1)°
Data collection top
Rigaku-AFC-6S
diffractometer
1063 reflections with I<2σ(I)
Absorption correction: empirical (using intensity measurements)
via ψ-scan (3 reflections) (North et al., 1968)
Rint = 0.027
Tmin = 0.78, Tmax = 0.853 standard reflections every 200 reflections
1385 measured reflections intensity decay: 1.3%
1268 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.029H-atom parameters constrained
wR(F2) = 0.109Δρmax = 0.23 e Å3
S = 1.19Δρmin = 0.29 e Å3
1268 reflectionsAbsolute structure: Flack (1983)
128 parametersAbsolute structure parameter: 0.07 (15)
1 restraint
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.51440 (19)0.30871 (11)0.07085 (11)0.0463 (3)
S20.65668 (15)0.47553 (10)0.52923 (10)0.0388 (2)
O10.6269 (6)0.6112 (4)0.5389 (4)0.0656 (10)
O20.8850 (5)0.4247 (4)0.5847 (4)0.0607 (10)
C10.6643 (6)0.3336 (4)0.2593 (4)0.0366 (8)
C20.5609 (6)0.4265 (4)0.3340 (4)0.0333 (7)
C30.3523 (6)0.4818 (4)0.2406 (4)0.0360 (7)
C40.1984 (7)0.5750 (4)0.2783 (5)0.0471 (10)
H40.22400.61470.37620.057*
C50.0054 (8)0.6072 (5)0.1664 (6)0.0563 (12)
H50.09930.66810.19110.068*
C60.0331 (8)0.5507 (6)0.0205 (6)0.0590 (13)
H60.16250.57450.05220.071*
C70.1169 (7)0.4595 (5)0.0196 (5)0.0522 (11)
H70.09090.42180.11870.063*
C80.3080 (7)0.4249 (4)0.0910 (4)0.0399 (8)
C90.8775 (8)0.2541 (5)0.3081 (6)0.0498 (10)
H9A0.93230.26570.41860.075*
H9B0.99650.28020.24990.075*
H9C0.84080.16550.28730.075*
C100.4619 (8)0.4013 (6)0.6374 (5)0.0538 (12)
H10A0.50150.42480.74620.081*
H10B0.47220.31000.62730.081*
H10C0.30580.42870.59750.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0513 (6)0.0555 (6)0.0322 (4)0.0040 (5)0.0068 (4)0.0078 (5)
S20.0326 (4)0.0503 (5)0.0313 (4)0.0048 (4)0.0014 (3)0.0061 (4)
O10.080 (2)0.050 (2)0.060 (2)0.0099 (18)0.0084 (18)0.0157 (16)
O20.0322 (13)0.100 (3)0.0459 (16)0.0022 (17)0.0047 (12)0.0082 (18)
C10.0355 (17)0.043 (2)0.0325 (16)0.0071 (16)0.0085 (13)0.0020 (15)
C20.0309 (16)0.0404 (19)0.0281 (15)0.0068 (15)0.0031 (13)0.0026 (14)
C30.0353 (15)0.0391 (18)0.0321 (16)0.0068 (18)0.0013 (12)0.0050 (17)
C40.046 (2)0.042 (2)0.050 (2)0.0023 (18)0.0010 (18)0.0007 (18)
C50.045 (2)0.053 (3)0.069 (3)0.010 (2)0.004 (2)0.011 (2)
C60.046 (2)0.070 (3)0.055 (3)0.000 (2)0.011 (2)0.017 (2)
C70.051 (2)0.066 (3)0.0357 (18)0.010 (2)0.0065 (16)0.008 (2)
C80.0403 (19)0.047 (2)0.0313 (17)0.0087 (18)0.0031 (14)0.0039 (16)
C90.047 (2)0.051 (3)0.053 (2)0.006 (2)0.0123 (19)0.002 (2)
C100.045 (2)0.084 (4)0.034 (2)0.003 (2)0.0115 (17)0.001 (2)
Geometric parameters (Å, º) top
S1—C11.731 (4)C2—C31.460 (5)
S1—C81.736 (4)C3—C41.397 (6)
S2—O11.431 (4)C3—C81.405 (5)
S2—O21.437 (3)C4—C51.395 (6)
S2—C21.759 (4)C5—C61.374 (8)
S2—C101.763 (5)C6—C71.375 (7)
C1—C21.359 (6)C7—C81.387 (5)
C1—C91.494 (6)
C1—S1—C892.9 (2)C3—C2—S2121.0 (3)
O1—S2—O2117.4 (2)C4—C3—C8118.8 (3)
O1—S2—C2108.7 (2)C4—C3—C2130.8 (4)
O2—S2—C2109.8 (2)C8—C3—C2110.4 (4)
O1—S2—C10108.0 (3)C5—C4—C3118.7 (4)
O2—S2—C10107.6 (2)C6—C5—C4121.4 (5)
C2—S2—C10104.4 (2)C5—C6—C7120.9 (4)
C2—C1—C9132.5 (4)C6—C7—C8118.6 (4)
C2—C1—S1111.0 (3)C7—C8—C3121.6 (4)
C9—C1—S1116.5 (3)C7—C8—S1127.1 (4)
C1—C2—C3114.5 (3)C3—C8—S1111.3 (3)
C1—C2—S2124.5 (3)
C8—S1—C1—C20.0 (3)S2—C2—C3—C8178.3 (3)
C8—S1—C1—C9179.0 (3)C8—C3—C4—C50.5 (6)
C9—C1—C2—C3179.1 (4)C2—C3—C4—C5177.7 (4)
S1—C1—C2—C30.3 (4)C3—C4—C5—C61.0 (7)
C9—C1—C2—S23.2 (6)C4—C5—C6—C70.6 (8)
S1—C1—C2—S2178.0 (2)C5—C6—C7—C80.4 (7)
O1—S2—C2—C1142.6 (3)C6—C7—C8—C30.9 (7)
O2—S2—C2—C112.8 (4)C6—C7—C8—S1177.4 (3)
C10—S2—C2—C1102.3 (4)C4—C3—C8—C70.4 (6)
O1—S2—C2—C339.9 (4)C2—C3—C8—C7179.0 (4)
O2—S2—C2—C3169.6 (3)C4—C3—C8—S1178.1 (3)
C10—S2—C2—C375.2 (3)C2—C3—C8—S10.5 (4)
C1—C2—C3—C4177.8 (4)C1—S1—C8—C7178.7 (4)
S2—C2—C3—C40.1 (6)C1—S1—C8—C30.3 (3)
C1—C2—C3—C80.5 (4)

Experimental details

(I)(IV)
Crystal data
Chemical formulaC8H8O2S2C10H10O2S2
Mr200.26226.30
Crystal system, space groupTriclinic, P1Monoclinic, P21
Temperature (K)293293
a, b, c (Å)4.032 (2), 5.717 (1), 9.626 (1)5.8228 (5), 10.440 (1), 8.6217 (9)
α, β, γ (°)86.04 (1), 80.60 (2), 86.09 (3)90, 99.57 (1), 90
V3)218.0 (1)516.8 (1)
Z12
Radiation typeCu KαMo Kα
µ (mm1)5.170.48
Crystal size (mm)0.36 × 0.28 × 0.080.55 × 0.38 × 0.35
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Rigaku-AFC-6S
diffractometer
Absorption correctionEmpirical (using intensity measurements)
ψ-scan (3 reflections) (North et al., 1968)
Empirical (using intensity measurements)
via ψ-scan (3 reflections) (North et al., 1968)
Tmin, Tmax0.22, 0.660.78, 0.85
No. of measured, independent and
observed [I<2σ(I)] reflections
1535, 791, 757 1385, 1268, 1063
Rint0.0300.027
(sin θ/λ)max1)0.6010.652
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.111, 1.15 0.029, 0.109, 1.19
No. of reflections7911268
No. of parameters56128
No. of restraints01
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.39, 0.320.23, 0.29
Absolute structure?Flack (1983)
Absolute structure parameter?0.07 (15)

Computer programs: CAD-4 Software (Enraf-Nonius, 1989), MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988), CAD-4 Software, MSC/AFC Diffractometer Control Software, TEXSAN (Molecular Structure Corporation, 1994), SAPI91 (Fan, 1991), SHELXL97 (Sheldrick, 1997), TEXSAN, SHELXL97.

Selected geometric parameters (Å, º) for (I) top
S1—C11.724 (2)C1—C21.353 (3)
S1—C41.788 (2)C1—C3i1.504 (3)
O1—C31.227 (3)C2—C31.447 (3)
C1—S1—C4102.83 (11)C1—C2—C3121.5 (2)
C2—C1—C3i119.5 (2)O1—C3—C2121.8 (2)
C2—C1—S1127.68 (17)O1—C3—C1i119.1 (2)
C3i—C1—S1112.84 (15)C2—C3—C1i119.1 (2)
C4—S1—C1—C24.5 (2)S1—C1—C2—C3179.95 (16)
C4—S1—C1—C3i175.06 (15)C1—C2—C3—O1179.4 (2)
C3i—C1—C2—C30.4 (3)C1—C2—C3—C1i0.4 (3)
Symmetry code: (i) x, y, z+1.
Selected geometric parameters (Å, º) for (IV) top
S1—C11.731 (4)S2—O21.437 (3)
S1—C81.736 (4)S2—C21.759 (4)
S2—O11.431 (4)S2—C101.763 (5)
C1—S1—C892.9 (2)O1—S2—C10108.0 (3)
O1—S2—O2117.4 (2)O2—S2—C10107.6 (2)
O1—S2—C2108.7 (2)C2—S2—C10104.4 (2)
O2—S2—C2109.8 (2)
 

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