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The title compounds are electron-poor ethynes. The structure determination of bis­(tert-butyl­sulfonyl)ethyne, C10H18O4S2, (I), is the first of a bis-sulfonyl-substituted ethyne. The mol­ecule is situated on a crystallographic inversion centre. The S-Csp bond [1.737 (2) Å] is the longest of this type reported to date. 1-tert-Butyl­sulfinyl-2-tert-butylsulfonyl­ethyne, C10H18O3S2, (II), which is basically the same as (I) minus one O atom, crystallizes isomorphous with (I). This results in a nearly equal distribution of the three O atoms over the four possible positions.

Supporting information

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Portable Document Format (PDF) file https://doi.org/10.1107/S0108270106047834/av3049sup4.pdf
Supplementary material

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Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106047834/av3049sup1.cif
Contains datablocks I, II, global

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Structure factor file (CIF format) https://doi.org/10.1107/S0108270106047834/av3049Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106047834/av3049IIsup3.hkl
Contains datablock II

CCDC references: 631316; 631317

Comment top

The high reactivity of bis(tert-butylsulfonyl)ethyne, (I), as a dienophile in Diels–Alder reactions has been demonstrated in several reports (Riera et al., 1990; Virgili et al., 1991; Gleiter & Ohlbach, 1994; Gleiter et al., 1996). Compound (I) is the only known stable ethyne substituted by two sulfonyl groups, whereas bis(arylsulfonyl)ethynes are reported as unstable at room temperature (Pasquato et al., 1991).

Compound (I) forms colourless polyhedral crystals and crystallizes in the monoclinic space group P21/c. Crystallographically imposed inversion symmetry was found in the structure of (I). Thus, there is only half a molecule in the asymmetric unit. This structure determination is the first to be reported of an uncomplexed bis-sulfonyl-substituted ethyne. Structures of mono-sulfonyl-substituted ethynes are also very rare (Hu et al., 2004; Tykwinski et al., 1993), so there is very little knowledge of the geometric parameters of such compounds. The CC triple bond is rather short (1.194 Å), whereas the sulfonyl SO2—Csp bond is the longest of this type reported to date.

It is interesting to note that all sulfonyl SO2—Csp bonds known in the literature [1.707 Å (Hu et al., 2004), 1.711 Å (Tykwinski et al., 1993) and 1.737 Å (present work)] are significantly longer than reported sulfide S—Csp bonds (mean 1.681 Å, SE standard error? = 0.001, standard deviation = 0.013; Cambridge Structural Database, Version?; Allen, 2002). This observation was confirmed by the determination and investigation of the structure of a mixed sulfonyl–thio compound, tert-butylsulfonyl-tert-butylthioethyne, (III) (Werz et al., 2006), which continues the series of (I) and (II), with another O atom absent at the same site. In that compound, the SO2—Csp bond is also longer than the S—Csp bond [1.697 (2) and 1.684 (3) Å, respectively]. In the case of saturated sp3 C atoms, this is not the case: in contrast, the sulfonyl SO2—Csp3 bonds have a mean length of 1.788 Å (standard error? = 0.001, standard deviation = 0.024), which is significantly shorter than the sulfide S—Csp3 bonds, with a mean length of 1.812 Å (standard error? = 0.001, standard deviation = 0.024) (Allen, 2002).

The bond angles at the S atom of (I) are as expected. The smallest angle is Csp3—S—Csp (Value?) and the largest is OS O (Value?). The OS—C angles are within this range, with the OS—Csp angles being smaller than the OS—Csp3 angles.

Due to the symmetry of the molecule of (I), the torsion angle tert-butyl—SO2—SO2tert-butyl is exactly 180°. In contrast, in the mixed compound (III) (Werz et al., 2006), the torsion tert-butyl—SO2Stert-butyl is nearly perfectly orthogonal (91.5°). We assume electronic rather than steric reasons. Further examinations are in progress.

The sulfonyl–sulfinyl compound 1-tert-butylsulfonyl-2-tert-butylsulfinylethyne, (II), with its three O atoms, is in the middle of the series between compounds (I) and (III). It crystallizes isomorphous with (I), which results in a nearly equal distribution of the three O atoms over the four possible positions. From an analytical point of view (chromatography, NMR, FAB mass spectrometry; see Experimental), it is already inherently clear that there can only be three O atoms, which means that in the asymmetric unit the sum of the occupancies of the two oxygen atoms must add to 1.5. The disorder of the O atoms leads to a somewhat restricted quality of the structure compared with (I) and thus prevents a detailed quantitative discussion of the results. Because of the disorder, the torsion angle tert-butyl—SO2—SO—tert-butyl is exactly 180°, and thus compound (II) is much more similar to (I) than to (III) (Werz et al., 2006).

Experimental top

Compound (I) was obtained from bis(tert-butylthio)ethyne by oxidation with chloroperbenzoic acid (Riera et al., 1990). It was recrystallized from what solvent? The preparation of (II) was carried out as follows. tert-Butylsulfonyl-tert-butylthioethyne, (III) (Werz et al., 2006) (1.0 equivalent) was dissolved in chloroform and petroleum ether (4:1, v/v). The mixture was cooled to 273 K and a solution of m-CPBA (0.9 equivalents) in chloroform was added slowly. The mixture was stirred for 2 d while warming to room temperature. After 2 d, the mixture was cooled to 273 K and filtered. The filtrate was washed three times with Na2S2O3 solution and then three times with NaHCO3 solution. The organic phase was dried over Na2SO4 and concentrated. Silica-gel column chromatography yielded the desired compound in pure form as the major product (64%), with compound (I) as a by-product. The two compounds could be easily distinguished by thin-layer chromatography. The structure of (II) was assigned unequivocally by NMR and mass spectrometric analyses: 1H NMR (500 MHz, CDCl3, δ, p.p.m.): 1.45 (s, 9H), 1.49 (s, 9H); 13C NMR (125 MHz, CHCl3, δ, p.p.m.): 22.9 (CH3), 23.3 (CH3), 60.9 (C), 61.9(C), 89.2 (Csp), 92.1 (Csp); MS (FAB+), calculated: 250.3781; found: 250.3785.

Refinement top

For compound (I), all H atoms could be located in a difference Fourier map and were refined isotropically; the resulting C—H distances range from 0.91 (3) to 0.99 (2) Å. For compound (II), the H atoms were taken into account using appropriate riding models, with C—H = 0.98 Å and with Uiso(H) = 1.5Ueq(C). [Please check added text] The occupancy values of the two disordered O atoms were restrained using the SHELXL SUMP command to add to 1.5.

Structure description top

The high reactivity of bis(tert-butylsulfonyl)ethyne, (I), as a dienophile in Diels–Alder reactions has been demonstrated in several reports (Riera et al., 1990; Virgili et al., 1991; Gleiter & Ohlbach, 1994; Gleiter et al., 1996). Compound (I) is the only known stable ethyne substituted by two sulfonyl groups, whereas bis(arylsulfonyl)ethynes are reported as unstable at room temperature (Pasquato et al., 1991).

Compound (I) forms colourless polyhedral crystals and crystallizes in the monoclinic space group P21/c. Crystallographically imposed inversion symmetry was found in the structure of (I). Thus, there is only half a molecule in the asymmetric unit. This structure determination is the first to be reported of an uncomplexed bis-sulfonyl-substituted ethyne. Structures of mono-sulfonyl-substituted ethynes are also very rare (Hu et al., 2004; Tykwinski et al., 1993), so there is very little knowledge of the geometric parameters of such compounds. The CC triple bond is rather short (1.194 Å), whereas the sulfonyl SO2—Csp bond is the longest of this type reported to date.

It is interesting to note that all sulfonyl SO2—Csp bonds known in the literature [1.707 Å (Hu et al., 2004), 1.711 Å (Tykwinski et al., 1993) and 1.737 Å (present work)] are significantly longer than reported sulfide S—Csp bonds (mean 1.681 Å, SE standard error? = 0.001, standard deviation = 0.013; Cambridge Structural Database, Version?; Allen, 2002). This observation was confirmed by the determination and investigation of the structure of a mixed sulfonyl–thio compound, tert-butylsulfonyl-tert-butylthioethyne, (III) (Werz et al., 2006), which continues the series of (I) and (II), with another O atom absent at the same site. In that compound, the SO2—Csp bond is also longer than the S—Csp bond [1.697 (2) and 1.684 (3) Å, respectively]. In the case of saturated sp3 C atoms, this is not the case: in contrast, the sulfonyl SO2—Csp3 bonds have a mean length of 1.788 Å (standard error? = 0.001, standard deviation = 0.024), which is significantly shorter than the sulfide S—Csp3 bonds, with a mean length of 1.812 Å (standard error? = 0.001, standard deviation = 0.024) (Allen, 2002).

The bond angles at the S atom of (I) are as expected. The smallest angle is Csp3—S—Csp (Value?) and the largest is OS O (Value?). The OS—C angles are within this range, with the OS—Csp angles being smaller than the OS—Csp3 angles.

Due to the symmetry of the molecule of (I), the torsion angle tert-butyl—SO2—SO2tert-butyl is exactly 180°. In contrast, in the mixed compound (III) (Werz et al., 2006), the torsion tert-butyl—SO2Stert-butyl is nearly perfectly orthogonal (91.5°). We assume electronic rather than steric reasons. Further examinations are in progress.

The sulfonyl–sulfinyl compound 1-tert-butylsulfonyl-2-tert-butylsulfinylethyne, (II), with its three O atoms, is in the middle of the series between compounds (I) and (III). It crystallizes isomorphous with (I), which results in a nearly equal distribution of the three O atoms over the four possible positions. From an analytical point of view (chromatography, NMR, FAB mass spectrometry; see Experimental), it is already inherently clear that there can only be three O atoms, which means that in the asymmetric unit the sum of the occupancies of the two oxygen atoms must add to 1.5. The disorder of the O atoms leads to a somewhat restricted quality of the structure compared with (I) and thus prevents a detailed quantitative discussion of the results. Because of the disorder, the torsion angle tert-butyl—SO2—SO—tert-butyl is exactly 180°, and thus compound (II) is much more similar to (I) than to (III) (Werz et al., 2006).

Computing details top

Data collection: SMART (Bruker, 2001) for (I). Cell refinement: SAINT-Plus (Bruker, 2001) for (I). Data reduction: SAINT-Plus for (I). Program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) for (I). Program(s) used to refine structure: SHELXL97 (Sheldrick, 1997) for (I). Molecular graphics: XP (Sheldrick, 1998) for (I). Software used to prepare material for publication: SHELXL97 for (I).

Figures top
[Figure 1] Fig. 1. A view of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. Unlabelled atoms are related to labelled atoms by the symmetry operator (1 - x,1 - y,-z). The plot for the isomorphous compound (II) is identical to that for (I) except that the occupancies of O1 and O2 are 0.655 (6) and 0.845 (6) respectively.
(I) Bis(tert-butylsulfonyl)ethyne top
Crystal data top
C10H18O4S2F(000) = 284
Mr = 266.36Dx = 1.368 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3981 reflections
a = 5.7037 (7) Åθ = 5.4–56.4°
b = 10.7251 (14) ŵ = 0.41 mm1
c = 10.5678 (14) ÅT = 100 K
β = 90.267 (2)°Polyhedron, colourless
V = 646.45 (14) Å30.39 × 0.21 × 0.09 mm
Z = 2
Data collection top
Bruker APEX
diffractometer
1599 independent reflections
Radiation source: fine-focus sealed tube1559 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.022
ω scansθmax = 28.3°, θmin = 2.7°
Absorption correction: multi-scan
(Blessing, 1995)
h = 77
Tmin = 0.854, Tmax = 0.960k = 1414
6615 measured reflectionsl = 1314
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084All H-atom parameters refined
S = 1.28 w = 1/[σ2(Fo2) + (0.0158P)2 + 0.7261P]
where P = (Fo2 + 2Fc2)/3
1599 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.35 e Å3
Crystal data top
C10H18O4S2V = 646.45 (14) Å3
Mr = 266.36Z = 2
Monoclinic, P21/nMo Kα radiation
a = 5.7037 (7) ŵ = 0.41 mm1
b = 10.7251 (14) ÅT = 100 K
c = 10.5678 (14) Å0.39 × 0.21 × 0.09 mm
β = 90.267 (2)°
Data collection top
Bruker APEX
diffractometer
1599 independent reflections
Absorption correction: multi-scan
(Blessing, 1995)
1559 reflections with I > 2σ(I)
Tmin = 0.854, Tmax = 0.960Rint = 0.022
6615 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.084All H-atom parameters refined
S = 1.28Δρmax = 0.40 e Å3
1599 reflectionsΔρmin = 0.35 e Å3
109 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
xyzUiso*/Ueq
S10.22664 (7)0.39214 (4)0.12201 (4)0.01359 (13)
O10.0492 (2)0.48056 (13)0.15527 (13)0.0201 (3)
O20.1607 (2)0.28301 (12)0.05177 (12)0.0206 (3)
C10.4308 (3)0.47174 (17)0.03109 (16)0.0160 (3)
C20.3928 (3)0.34710 (16)0.26033 (16)0.0143 (3)
C30.2114 (3)0.28751 (19)0.34855 (18)0.0200 (4)
H3A0.093 (4)0.348 (2)0.374 (2)0.020 (6)*
H3B0.292 (4)0.260 (2)0.421 (2)0.031 (7)*
H3C0.129 (5)0.218 (3)0.307 (3)0.036 (7)*
C40.5020 (4)0.46317 (18)0.32022 (18)0.0200 (4)
H4A0.383 (4)0.525 (2)0.345 (2)0.022 (6)*
H4B0.616 (5)0.502 (2)0.263 (3)0.033 (7)*
H4C0.578 (5)0.440 (2)0.393 (3)0.031 (7)*
C50.5795 (3)0.25378 (18)0.21940 (18)0.0186 (4)
H5A0.660 (4)0.229 (2)0.294 (2)0.020 (6)*
H5B0.508 (4)0.180 (2)0.178 (2)0.022 (6)*
H5C0.686 (4)0.291 (2)0.166 (2)0.026 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0137 (2)0.0154 (2)0.0117 (2)0.00155 (15)0.00001 (14)0.00180 (15)
O10.0166 (6)0.0229 (7)0.0208 (6)0.0034 (5)0.0022 (5)0.0032 (5)
O20.0235 (7)0.0207 (7)0.0177 (6)0.0058 (5)0.0036 (5)0.0010 (5)
C10.0173 (8)0.0168 (8)0.0138 (8)0.0009 (6)0.0002 (6)0.0014 (6)
C20.0138 (7)0.0173 (8)0.0119 (7)0.0005 (6)0.0003 (6)0.0028 (6)
C30.0173 (8)0.0260 (10)0.0168 (9)0.0007 (7)0.0024 (7)0.0071 (7)
C40.0225 (9)0.0219 (9)0.0155 (9)0.0027 (7)0.0032 (7)0.0024 (7)
C50.0152 (8)0.0201 (9)0.0205 (9)0.0026 (7)0.0008 (7)0.0027 (7)
Geometric parameters (Å, º) top
S1—O11.4321 (14)C3—H3B0.94 (3)
S1—O21.4351 (13)C3—H3C0.98 (3)
S1—C11.7374 (18)C4—H4A0.98 (2)
S1—C21.8044 (17)C4—H4B0.98 (3)
C1—C1i1.195 (4)C4—H4C0.91 (3)
C2—C51.526 (2)C5—H5A0.95 (2)
C2—C41.528 (2)C5—H5B0.99 (2)
C2—C31.535 (2)C5—H5C0.92 (3)
C3—H3A0.98 (2)
O1—S1—O2118.90 (8)C2—C3—H3C111.4 (16)
O1—S1—C1106.66 (8)H3A—C3—H3C107 (2)
O2—S1—C1106.82 (8)H3B—C3—H3C111 (2)
O1—S1—C2110.35 (8)C2—C4—H4A112.2 (14)
O2—S1—C2109.63 (8)C2—C4—H4B110.9 (15)
C1—S1—C2103.22 (8)H4A—C4—H4B110 (2)
C1i—C1—S1178.9 (2)C2—C4—H4C108.2 (16)
C5—C2—C4111.61 (15)H4A—C4—H4C107 (2)
C5—C2—C3111.87 (15)H4B—C4—H4C108 (2)
C4—C2—C3111.23 (15)C2—C5—H5A106.5 (14)
C5—C2—S1108.10 (12)C2—C5—H5B111.3 (14)
C4—C2—S1109.21 (12)H5A—C5—H5B110.0 (19)
C3—C2—S1104.50 (12)C2—C5—H5C110.5 (15)
C2—C3—H3A110.9 (13)H5A—C5—H5C108 (2)
C2—C3—H3B107.3 (16)H5B—C5—H5C111 (2)
H3A—C3—H3B109 (2)
Symmetry code: (i) x+1, y+1, z.
(II) 1-tert-Butylsulfonyl-2-tert-butylsulfinylethyne top
Crystal data top
C10H18O3S2Z = 2
Mr = 250.36F(000) = 268
Monoclinic, P21/nDx = 1.281 Mg m3
Hall symbol: -P 2ynCell parameters from 1857 reflections
a = 5.7463 (4) ŵ = 0.40 mm1
b = 10.7328 (8) ÅT = 200 K
c = 10.5299 (7) ÅPolyhedron, colourless
β = 92.109 (1)°0.56 × 0.10 × 0.08 mm
V = 648.98 (8) Å3
Data collection top
Absorption correction: multi-scan
(Blessing, 1995)
Tmin = 0.73, Tmax = 0.97
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0379P)2 + 1.6512P]
where P = (Fo2 + 2Fc2)/3
1326 reflections(Δ/σ)max < 0.001
78 parametersΔρmax = 0.95 e Å3
1 restraintΔρmin = 0.80 e Å3
Crystal data top
C10H18O3S2β = 92.109 (1)°
Mr = 250.36V = 648.98 (8) Å3
Monoclinic, P21/nZ = 2
a = 5.7463 (4) ŵ = 0.40 mm1
b = 10.7328 (8) ÅT = 200 K
c = 10.5299 (7) Å0.56 × 0.10 × 0.08 mm
Data collection top
Absorption correction: multi-scan
(Blessing, 1995)
Tmin = 0.73, Tmax = 0.97
Refinement top
R[F2 > 2σ(F2)] = 0.0621 restraint
wR(F2) = 0.147H-atom parameters constrained
S = 1.05Δρmax = 0.95 e Å3
1326 reflectionsΔρmin = 0.80 e Å3
78 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.22683 (16)0.40575 (11)0.12677 (9)0.0460 (3)
O10.0685 (8)0.4894 (4)0.1539 (4)0.0518 (14)0.655 (6)
O20.1454 (7)0.2938 (4)0.0639 (3)0.0721 (15)0.845 (6)
C10.4347 (6)0.4747 (4)0.0335 (3)0.0403 (9)
C20.4053 (6)0.3611 (3)0.2654 (3)0.0317 (7)
C30.2277 (6)0.3112 (4)0.3583 (3)0.0452 (10)
H3A0.12360.37890.38240.068*
H3B0.30990.27860.43440.068*
H3C0.13610.24440.31730.068*
C40.5320 (7)0.4748 (4)0.3191 (3)0.0447 (9)
H4A0.41860.54020.33680.067*
H4B0.64150.50560.25720.067*
H4C0.61750.45210.39800.067*
C50.5740 (7)0.2610 (4)0.2263 (4)0.0485 (10)
H5A0.66040.22970.30170.073*
H5B0.68340.29610.16670.073*
H5C0.48750.19240.18520.073*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0359 (5)0.0718 (7)0.0301 (5)0.0125 (5)0.0010 (3)0.0149 (5)
O10.057 (3)0.053 (3)0.046 (2)0.006 (2)0.004 (2)0.014 (2)
O20.079 (3)0.097 (3)0.0392 (19)0.056 (2)0.0132 (17)0.0001 (19)
C10.0385 (19)0.054 (2)0.0281 (17)0.0000 (17)0.0003 (13)0.0103 (16)
C20.0299 (16)0.0409 (19)0.0244 (15)0.0005 (14)0.0018 (12)0.0056 (14)
C30.037 (2)0.062 (3)0.037 (2)0.0005 (18)0.0083 (16)0.0188 (18)
C40.048 (2)0.055 (2)0.0304 (18)0.0058 (19)0.0028 (16)0.0042 (17)
C50.044 (2)0.045 (2)0.058 (2)0.0036 (18)0.0127 (18)0.0033 (19)
Geometric parameters (Å, º) top
S1—O11.317 (4)C3—H3B0.9800
S1—O21.441 (4)C3—H3C0.9800
S1—C11.739 (4)C4—H4A0.9800
S1—C21.818 (3)C4—H4B0.9800
C1—C1i1.182 (7)C4—H4C0.9800
C2—C51.514 (5)C5—H5A0.9800
C2—C41.520 (5)C5—H5B0.9800
C2—C31.535 (4)C5—H5C0.9800
C3—H3A0.9800
O1—S1—O2116.9 (3)C2—C3—H3C109.5
O1—S1—C1109.1 (2)H3A—C3—H3C109.5
O2—S1—C1108.2 (2)H3B—C3—H3C109.5
O1—S1—C2112.3 (2)C2—C4—H4A109.5
O2—S1—C2108.3 (2)C2—C4—H4B109.5
C1—S1—C2100.77 (16)H4A—C4—H4B109.5
C1i—C1—S1176.0 (5)C2—C4—H4C109.5
C5—C2—C4111.6 (3)H4A—C4—H4C109.5
C5—C2—C3111.9 (3)H4B—C4—H4C109.5
C4—C2—C3111.3 (3)C2—C5—H5A109.5
C5—C2—S1108.5 (3)C2—C5—H5B109.5
C4—C2—S1109.6 (2)H5A—C5—H5B109.5
C3—C2—S1103.6 (2)C2—C5—H5C109.5
C2—C3—H3A109.5H5A—C5—H5C109.5
C2—C3—H3B109.5H5B—C5—H5C109.5
H3A—C3—H3B109.5
Symmetry code: (i) x+1, y+1, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC10H18O4S2C10H18O3S2
Mr266.36250.36
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/n
Temperature (K)100200
a, b, c (Å)5.7037 (7), 10.7251 (14), 10.5678 (14)5.7463 (4), 10.7328 (8), 10.5299 (7)
α, β, γ (°)90, 90.267 (2), 9090, 92.109 (1), 90
V3)646.45 (14)648.98 (8)
Z22
Radiation typeMo Kα?, λ = ? Å
µ (mm1)0.410.40
Crystal size (mm)0.39 × 0.21 × 0.090.56 × 0.10 × 0.08
Data collection
DiffractometerBruker APEX?
Absorption correctionMulti-scan
(Blessing, 1995)
Multi-scan
(Blessing, 1995)
Tmin, Tmax0.854, 0.9600.73, 0.97
No. of measured, independent and
observed reflections
6615, 1599, 1559 [I > 2σ(I)]?, ?, ? (?)
Rint0.022?
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.037, 0.084, 1.28 0.062, 0.147, 1.05
No. of reflections15991326
No. of parameters10978
No. of restraints01
H-atom treatmentAll H-atom parameters refinedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.350.95, 0.80

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2001), SAINT-Plus, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Sheldrick, 1998), SHELXL97.

Selected geometric parameters (Å, º) for (I) top
S1—O11.4321 (14)S1—C21.8044 (17)
S1—O21.4351 (13)C1—C1i1.195 (4)
S1—C11.7374 (18)
O1—S1—O2118.90 (8)O2—S1—C2109.63 (8)
O1—S1—C1106.66 (8)C1—S1—C2103.22 (8)
O2—S1—C1106.82 (8)C1i—C1—S1178.9 (2)
O1—S1—C2110.35 (8)
Symmetry code: (i) x+1, y+1, z.
 

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