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Acta Cryst. (2007). E63, m2071    [ doi:10.1107/S1600536807031984 ]

Hexaaquazinc(II) D-camphor-10-sulfonate

M. Schepke, F. T. Edelmann and S. Blaurock

Abstract top

The structure of the title compound, [Zn(H2O)6](C10H15O4S)2, consists of two D-camphor-10-sulfonate anions, together with essentially regular octahedral [Zn(H2O)6]2+ cations. The coordinated water molecules around the zinc ion are engaged in an extensive network of hydrogen bonds with the O atoms of the sulfonate groups. Distances between hydrogen-bonded O atoms are in the range 2.704 (4)-2.845 (4) Å. The title compound and its nickel and copper analogues are isomorphous.

Comment top

The title compound was prepared as part of an ongoing research project to develop new materials for the zinc-catalyzed production of polycarbonates from CO2 and epoxides (ethylene oxide, propylene oxide etc.). Two analogous metal salts of D-camphor-10-sulfonic acid have been structurally characterized previously (copper: Couldwell et al., 1978; nickel: Henderson & Nicholson, 1995). Here we present the crystal structure of [Zn(H2O)6].

The three metal salts of D-camphor-10 sulfonic acid are isomorphous. The lattice of the title compound consists of [Zn(H2O)6] cations and two crystallographically independent D-camphor-sulfonate anions. The cation is essentially octahedral, with Zn—O distances ranging from 2.048 (2) to 2.099 (2) Å and O—Zn—O angles between 82.99 (11) and 96.47 (6)°. No coordination of either the sulfonate or the ketone O atoms of the anions is observed.

The two independent D-camphor-10 sulfonate anions show only small differences in bond parameters. As in the lattices of the related nickel and copper compounds, the water sphere and the O atoms of the sulfonate groups are involved in a complex hydrogen bonding network. In contrast to the structure of the nickel complex, in which all H atoms were reported to take part in hydrogen bonds, we find that two water H atoms (H01 & H03) of the title compound do not form hydrogen bonds. This may be associated with the difficulty in localizing H atoms in pseudosymmetric structures, a problem that surprisingly was not mentioned in the earlier reports (see X-ray details).

Related literature top

For related literature, see: Couldwell et al. (1978); Henderson & Nicholson (1995); Sheldrick (1990).

Experimental top

The title compound was prepared by saturating a hot aqueous solution of D-camphor-10-sulfonic acid with zinc oxide, followed by filtration and slow evaporation at ambient temperature.

Refinement top

All H atoms were refined with a riding model with O—H = 0.84 Å, C—H ranging from 0.98–1.00Å and U(H) = 1.2 Ueq(C,O) or U(H) = 1.5 Ueq(Cmethyl). It is probable that X-ray data alone cannot provide unambiguous positions for all H.

Computing details top

Data collection: XSCANS (Fait, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Siemens, 1995); software used to prepare material for publication: SHELXTL-Plus.

Figures top
[Figure 1] Fig. 1. The molecule of the title compound in the crystal. Thermal ellipsoids represent 50% probability levels. H-Atom radii are arbitrary.
Hexaaquazinc(II) D-camphor-10-sulfonate top
Crystal data top
[Zn(H2O)6](C10H15O4S)2F(000) = 672
Mr = 636.03Dx = 1.484 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2ybCell parameters from 66 reflections
a = 11.7293 (14) Åθ = 3–12.5°
b = 7.0854 (8) ŵ = 1.07 mm−1
c = 17.169 (2) ÅT = 173 K
β = 93.841 (10)°Plate, colourless
V = 1423.7 (3) Å30.60 × 0.60 × 0.20 mm
Z = 2
Data collection top
Siemens P4
diffractometer		5903 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
graphiteθmax = 28.8°, θmin = 3.0°
ω scansh = −15→15
Absorption correction: empirical (using intensity measurements)
(Siemens, 1994)		k = −9→9
Tmin = 0.565, Tmax = 0.814l = 0→22
7590 measured reflections3 standard reflections every 247 reflections
7364 independent reflections intensity decay: none
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)] = 0.034H-atom parameters constrained
wR(F2) = 0.087 w = 1/[σ2(Fo2) + (0.0537P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.005
7364 reflectionsΔρmax = 0.51 e Å−3
334 parametersΔρmin = −0.47 e Å−3
1 restraintAbsolute structure: Flack (1983), 3392 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: −0.005 (10)
Crystal data top
[Zn(H2O)6](C10H15O4S)2V = 1423.7 (3) Å3
Mr = 636.03Z = 2
Monoclinic, P21Mo Kα radiation
a = 11.7293 (14) ŵ = 1.07 mm−1
b = 7.0854 (8) ÅT = 173 K
c = 17.169 (2) Å0.60 × 0.60 × 0.20 mm
β = 93.841 (10)°
Data collection top
Siemens P4
diffractometer		5903 reflections with I > 2σ(I)
Absorption correction: empirical (using intensity measurements)
(Siemens, 1994)		Rint = 0.023
Tmin = 0.565, Tmax = 0.814θmax = 28.8°
7590 measured reflections3 standard reflections every 247 reflections
7364 independent reflections intensity decay: none
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.51 e Å−3
S = 0.97Δρmin = −0.47 e Å−3
7364 reflectionsAbsolute structure: Flack (1983), 3392 Friedel pairs
334 parametersFlack parameter: −0.005 (10)
1 restraint
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
Zn0.24152 (2)0.23602 (6)0.494431 (14)0.01905 (7)
O110.35940 (15)0.2373 (4)0.58803 (11)0.0380 (4)
H010.42410.26230.57250.046*
H020.36350.12110.59730.046*
O120.12659 (17)0.2322 (4)0.39833 (12)0.0437 (5)
H030.07730.15690.41320.052*
H040.09070.33480.39410.052*
O130.1539 (2)0.4604 (3)0.54210 (15)0.0260 (5)
H050.08680.44200.55480.031*
H060.15350.57490.52960.031*
O140.32956 (19)0.0144 (3)0.44599 (15)0.0263 (6)
H070.39610.00900.43080.032*
H080.3149−0.09840.45640.032*
O150.1528 (2)0.0204 (3)0.54855 (15)0.0265 (5)
H090.1738−0.09270.55270.032*
H100.08430.01680.55970.032*
O160.3304 (2)0.4525 (3)0.44272 (16)0.0316 (6)
H110.31190.56510.43330.038*
H120.39710.44580.42810.038*
S−0.08148 (4)0.23795 (13)0.66721 (3)0.01718 (10)
O1−0.0216 (2)0.0609 (3)0.65366 (14)0.0227 (5)
O2−0.01836 (19)0.4015 (3)0.64225 (14)0.0237 (5)
O3−0.19981 (12)0.2363 (4)0.63493 (9)0.0248 (3)
C10.00787 (17)0.2248 (5)0.82661 (12)0.0186 (4)
C2−0.0241 (2)0.2782 (4)0.90868 (15)0.0279 (7)
C30.0859 (2)0.2888 (5)0.96047 (16)0.0353 (8)
H3A0.08550.19821.00440.042*
H3B0.09940.41770.98140.042*
C40.17475 (19)0.2344 (6)0.90275 (13)0.0268 (5)
H40.25480.27270.91930.032*
C50.1589 (2)0.0215 (4)0.88764 (16)0.0280 (6)
H5A0.1549−0.04900.93720.034*
H5B0.2219−0.03020.85850.034*
C60.0428 (2)0.0126 (4)0.83773 (16)0.0226 (5)
H6A−0.0152−0.05760.86550.027*
H6B0.0522−0.04890.78680.027*
C70.1269 (2)0.3230 (4)0.82407 (15)0.0203 (5)
C80.1166 (3)0.5399 (4)0.8263 (2)0.0358 (7)
H8A0.19230.59530.83830.043*
H8B0.06550.57660.86650.043*
H8C0.08550.58570.77530.043*
C90.1999 (2)0.2681 (4)0.75685 (14)0.0260 (7)
H9A0.27980.30170.77040.031*
H9B0.17250.33560.70940.031*
H9C0.19400.13180.74780.031*
O4−0.11982 (18)0.3062 (4)0.92834 (12)0.0454 (6)
C10−0.09305 (19)0.2637 (4)0.76947 (13)0.0199 (6)
H11A−0.11780.39500.77860.024*
H11B−0.15610.18040.78390.024*
S'0.40990 (4)−0.26391 (13)0.65060 (3)0.01825 (10)
O1'0.4675 (2)−0.4357 (3)0.62698 (15)0.0253 (5)
O2'0.46865 (19)−0.0944 (3)0.62639 (15)0.0234 (5)
O3'0.28824 (12)−0.2646 (4)0.62623 (9)0.0255 (3)
C1'0.53121 (17)−0.2603 (5)0.79946 (12)0.0202 (4)
C2'0.5312 (3)−0.3858 (4)0.87247 (17)0.0281 (6)
C3'0.6312 (3)−0.3214 (4)0.92760 (18)0.0368 (8)
H3'10.6872−0.42440.93810.044*
H3'20.6048−0.27500.97770.044*
C4'0.6823 (2)−0.1597 (4)0.88023 (16)0.0271 (6)
H4'0.7314−0.06910.91210.033*
C5'0.74126 (19)−0.2540 (6)0.81366 (15)0.0301 (5)
H5'10.7911−0.35870.83330.036*
H5'20.7876−0.16180.78610.036*
C6'0.6400 (2)−0.3285 (4)0.75948 (16)0.0245 (6)
H6'10.6419−0.46790.75600.029*
H6'20.6421−0.27500.70630.029*
C7'0.5732 (2)−0.0704 (4)0.83839 (15)0.0218 (5)
C8'0.4922 (3)0.0105 (5)0.8950 (2)0.0334 (8)
H8'10.4646−0.09110.92760.040*
H8'20.42710.06990.86580.040*
H8'30.53240.10490.92830.040*
C9'0.6006 (2)0.0861 (4)0.78097 (17)0.0288 (6)
H9'10.52950.13170.75410.035*
H9'20.65090.03610.74250.035*
H9'30.63890.19050.80950.035*
O4'0.4641 (2)−0.5084 (3)0.88454 (15)0.0405 (6)
C10'0.41553 (17)−0.2650 (6)0.75433 (12)0.0228 (4)
H11C0.3713−0.15490.77110.027*
H11D0.3751−0.37950.77070.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn0.01953 (12)0.01708 (11)0.02041 (12)−0.00012 (19)0.00036 (9)0.0005 (2)
O110.0426 (10)0.0213 (8)0.0473 (11)0.0010 (15)−0.0189 (8)0.0040 (15)
O120.0539 (11)0.0211 (9)0.0518 (11)−0.0047 (15)−0.0287 (9)0.0055 (16)
O130.0290 (13)0.0186 (12)0.0311 (13)−0.0012 (10)0.0072 (11)−0.0011 (10)
O140.0218 (13)0.0234 (12)0.0346 (15)0.0021 (10)0.0082 (11)−0.0007 (11)
O150.0228 (12)0.0240 (13)0.0340 (14)−0.0006 (10)0.0104 (10)0.0037 (10)
O160.0298 (14)0.0245 (13)0.0416 (17)0.0063 (11)0.0107 (12)0.0131 (12)
S0.0163 (2)0.0165 (2)0.0185 (2)0.0004 (4)−0.00026 (17)−0.0013 (4)
O10.0243 (12)0.0192 (11)0.0241 (11)0.0017 (9)−0.0010 (9)−0.0046 (8)
O20.0225 (12)0.0206 (11)0.0281 (12)−0.0026 (9)0.0027 (9)0.0058 (9)
O30.0186 (7)0.0275 (8)0.0273 (8)−0.0018 (13)−0.0051 (6)0.0003 (13)
C10.0178 (9)0.0216 (12)0.0163 (9)0.0030 (14)0.0007 (7)0.0024 (14)
C20.0317 (13)0.0301 (18)0.0220 (12)0.0004 (10)0.0032 (10)−0.0047 (10)
C30.0382 (16)0.047 (2)0.0205 (13)−0.0005 (12)−0.0004 (11)−0.0061 (11)
C40.0231 (10)0.0327 (12)0.0238 (10)−0.0050 (19)−0.0048 (8)0.0032 (19)
C50.0281 (14)0.0294 (15)0.0258 (14)0.0030 (11)−0.0045 (11)0.0048 (11)
C60.0255 (13)0.0179 (12)0.0244 (13)−0.0023 (10)0.0007 (10)0.0045 (10)
C70.0160 (11)0.0205 (12)0.0240 (13)−0.0019 (9)−0.0008 (10)−0.0005 (10)
C80.0377 (17)0.0240 (15)0.0445 (18)−0.0064 (13)−0.0055 (14)−0.0038 (13)
C90.0216 (11)0.033 (2)0.0238 (11)−0.0013 (11)0.0026 (9)0.0045 (11)
O40.0312 (11)0.0763 (18)0.0298 (11)0.0040 (11)0.0112 (9)−0.0116 (10)
C100.0163 (9)0.0250 (17)0.0184 (10)0.0023 (10)0.0013 (8)−0.0009 (10)
S'0.0153 (2)0.0172 (2)0.0220 (2)−0.0003 (4)−0.00066 (18)0.0007 (4)
O1'0.0248 (13)0.0203 (12)0.0303 (13)−0.0014 (10)−0.0029 (11)−0.0057 (10)
O2'0.0178 (12)0.0217 (11)0.0310 (13)−0.0031 (9)0.0034 (10)0.0036 (10)
O3'0.0167 (7)0.0271 (8)0.0319 (8)−0.0018 (12)−0.0040 (6)−0.0023 (14)
C1'0.0187 (9)0.0208 (10)0.0211 (9)−0.0035 (16)0.0008 (8)0.0005 (17)
C2'0.0327 (15)0.0248 (14)0.0263 (14)−0.0019 (12)−0.0011 (12)0.0016 (11)
C3'0.0413 (17)0.0409 (18)0.0265 (14)−0.0017 (13)−0.0091 (13)0.0050 (11)
C4'0.0248 (13)0.0277 (15)0.0278 (14)−0.0003 (11)−0.0062 (11)−0.0025 (11)
C5'0.0202 (10)0.0333 (14)0.0360 (12)0.0044 (17)−0.0044 (9)−0.0015 (19)
C6'0.0180 (12)0.0269 (13)0.0284 (13)0.0027 (9)−0.0003 (11)−0.0052 (10)
C7'0.0182 (12)0.0244 (14)0.0231 (13)−0.0024 (10)0.0029 (10)−0.0052 (10)
C8'0.0277 (15)0.0366 (17)0.0367 (18)−0.0037 (13)0.0086 (14)−0.0138 (14)
C9'0.0255 (14)0.0249 (14)0.0358 (16)−0.0052 (11)0.0012 (12)−0.0010 (12)
O4'0.0471 (15)0.0360 (13)0.0381 (14)−0.0126 (11)−0.0002 (11)0.0105 (10)
C10'0.0178 (9)0.0294 (11)0.0215 (10)−0.0022 (17)0.0032 (8)−0.0002 (18)
Geometric parameters (Å, °) top
Zn—O112.0485 (17)C7—C81.543 (4)
Zn—O122.0597 (17)C8—H8A0.9800
Zn—O142.083 (2)C8—H8B0.9800
Zn—O162.086 (2)C8—H8C0.9800
Zn—O132.090 (2)C9—H9A0.9800
Zn—O152.100 (2)C9—H9B0.9800
O11—H010.8405C9—H9C0.9800
O11—H020.8387C10—H11A0.9900
O12—H030.8394C10—H11B0.9900
O12—H040.8407S'—O2'1.459 (2)
O13—H050.8401S'—O3'1.4600 (14)
O13—H060.8394S'—O1'1.462 (2)
O14—H070.8404S'—C10'1.778 (2)
O14—H080.8397C1'—C10'1.517 (3)
O15—H090.8403C1'—C2'1.537 (4)
O15—H100.8391C1'—C6'1.566 (3)
O16—H110.8392C1'—C7'1.567 (4)
O16—H120.8396C2'—O4'1.200 (4)
S—O21.455 (2)C2'—C3'1.527 (4)
S—O31.4596 (14)C3'—C4'1.549 (4)
S—O11.464 (2)C3'—H3'10.9900
S—C101.779 (2)C3'—H3'20.9900
C1—C101.511 (3)C4'—C5'1.529 (4)
C1—C21.530 (3)C4'—C7'1.559 (4)
C1—C71.563 (3)C4'—H4'1.0000
C1—C61.566 (4)C5'—C6'1.551 (3)
C2—O41.210 (3)C5'—H5'10.9900
C2—C31.519 (4)C5'—H5'20.9900
C3—C41.535 (4)C6'—H6'10.9900
C3—H3A0.9900C6'—H6'20.9900
C3—H3B0.9900C7'—C8'1.517 (4)
C4—C51.540 (5)C7'—C9'1.532 (4)
C4—C71.560 (3)C8'—H8'10.9800
C4—H41.0000C8'—H8'20.9800
C5—C61.561 (3)C8'—H8'30.9800
C5—H5A0.9900C9'—H9'10.9800
C5—H5B0.9900C9'—H9'20.9800
C6—H6A0.9900C9'—H9'30.9800
C6—H6B0.9900C10'—H11C0.9900
C7—C91.533 (3)C10'—H11D0.9900
O11—Zn—O12178.36 (9)H8A—C8—H8B109.5
O11—Zn—O1489.42 (10)C7—C8—H8C109.5
O12—Zn—O1489.18 (11)H8A—C8—H8C109.5
O11—Zn—O1690.03 (11)H8B—C8—H8C109.5
O12—Zn—O1689.28 (11)C7—C9—H9A109.5
O14—Zn—O1696.27 (6)C7—C9—H9B109.5
O11—Zn—O1390.77 (11)H9A—C9—H9B109.5
O12—Zn—O1390.62 (11)C7—C9—H9C109.5
O14—Zn—O13179.36 (12)H9A—C9—H9C109.5
O16—Zn—O1383.13 (11)H9B—C9—H9C109.5
O11—Zn—O1589.10 (11)C1—C10—S120.91 (16)
O12—Zn—O1591.61 (11)C1—C10—H11A107.1
O14—Zn—O1584.37 (11)S—C10—H11A107.1
O16—Zn—O15178.92 (12)C1—C10—H11B107.1
O13—Zn—O1596.24 (6)S—C10—H11B107.1
Zn—O11—H01109.1H11A—C10—H11B106.8
Zn—O11—H0299.9O2'—S'—O3'113.11 (15)
H01—O11—H02103.0O2'—S'—O1'111.75 (9)
Zn—O12—H03101.0O3'—S'—O1'112.23 (15)
Zn—O12—H04110.8O2'—S'—C10'107.61 (17)
H03—O12—H04103.0O3'—S'—C10'104.89 (9)
Zn—O13—H05118.5O1'—S'—C10'106.69 (17)
Zn—O13—H06128.9C10'—C1'—C2'110.8 (2)
H05—O13—H06103.2C10'—C1'—C6'119.8 (2)
Zn—O14—H07130.8C2'—C1'—C6'102.9 (2)
Zn—O14—H08121.2C10'—C1'—C7'118.8 (3)
H07—O14—H08103.3C2'—C1'—C7'99.55 (19)
Zn—O15—H09125.5C6'—C1'—C7'102.11 (19)
Zn—O15—H10129.3O4'—C2'—C3'126.5 (3)
H09—O15—H10103.4O4'—C2'—C1'126.6 (3)
Zn—O16—H11130.6C3'—C2'—C1'106.9 (2)
Zn—O16—H12126.0C2'—C3'—C4'101.7 (2)
H11—O16—H12103.3C2'—C3'—H3'1111.4
O2—S—O3112.59 (15)C4'—C3'—H3'1111.4
O2—S—O1112.13 (10)C2'—C3'—H3'2111.4
O3—S—O1112.77 (16)C4'—C3'—H3'2111.4
O2—S—C10106.45 (14)H3'1—C3'—H3'2109.3
O3—S—C10104.01 (10)C5'—C4'—C3'106.2 (3)
O1—S—C10108.28 (14)C5'—C4'—C7'103.4 (2)
C10—C1—C2108.9 (2)C3'—C4'—C7'102.0 (2)
C10—C1—C7124.3 (2)C5'—C4'—H4'114.6
C2—C1—C7100.9 (2)C3'—C4'—H4'114.6
C10—C1—C6116.2 (2)C7'—C4'—H4'114.6
C2—C1—C6101.7 (2)C4'—C5'—C6'103.34 (19)
C7—C1—C6101.77 (19)C4'—C5'—H5'1111.1
O4—C2—C3126.6 (3)C6'—C5'—H5'1111.1
O4—C2—C1125.9 (2)C4'—C5'—H5'2111.1
C3—C2—C1107.5 (2)C6'—C5'—H5'2111.1
C2—C3—C4101.3 (2)H5'1—C5'—H5'2109.1
C2—C3—H3A111.5C5'—C6'—C1'104.2 (2)
C4—C3—H3A111.5C5'—C6'—H6'1110.9
C2—C3—H3B111.5C1'—C6'—H6'1110.9
C4—C3—H3B111.5C5'—C6'—H6'2110.9
H3A—C3—H3B109.3C1'—C6'—H6'2110.9
C3—C4—C5106.0 (2)H6'1—C6'—H6'2108.9
C3—C4—C7103.7 (2)C8'—C7'—C9'107.8 (2)
C5—C4—C7102.5 (2)C8'—C7'—C4'112.8 (2)
C3—C4—H4114.4C9'—C7'—C4'112.9 (2)
C5—C4—H4114.4C8'—C7'—C1'113.9 (2)
C7—C4—H4114.4C9'—C7'—C1'114.9 (2)
C4—C5—C6102.9 (2)C4'—C7'—C1'94.2 (2)
C4—C5—H5A111.2C7'—C8'—H8'1109.5
C6—C5—H5A111.2C7'—C8'—H8'2109.5
C4—C5—H5B111.2H8'1—C8'—H8'2109.5
C6—C5—H5B111.2C7'—C8'—H8'3109.5
H5A—C5—H5B109.1H8'1—C8'—H8'3109.5
C5—C6—C1103.9 (2)H8'2—C8'—H8'3109.5
C5—C6—H6A111.0C7'—C9'—H9'1109.5
C1—C6—H6A111.0C7'—C9'—H9'2109.5
C5—C6—H6B111.0H9'1—C9'—H9'2109.5
C1—C6—H6B111.0C7'—C9'—H9'3109.5
H6A—C6—H6B109.0H9'1—C9'—H9'3109.5
C9—C7—C8108.6 (2)H9'2—C9'—H9'3109.5
C9—C7—C4111.3 (2)C1'—C10'—S'118.91 (14)
C8—C7—C4113.8 (3)C1'—C10'—H11C107.6
C9—C7—C1116.9 (2)S'—C10'—H11C107.6
C8—C7—C1111.8 (2)C1'—C10'—H11D107.6
C4—C7—C193.85 (19)S'—C10'—H11D107.6
C7—C8—H8A109.5H11C—C10'—H11D107.0
C7—C8—H8B109.5
C10—C1—C2—O415.3 (4)C10'—C1'—C2'—O4'18.1 (5)
C7—C1—C2—O4147.5 (3)C6'—C1'—C2'—O4'−111.2 (3)
C6—C1—C2—O4−107.9 (3)C7'—C1'—C2'—O4'144.0 (3)
C10—C1—C2—C3−164.9 (2)C10'—C1'—C2'—C3'−160.6 (3)
C7—C1—C2—C3−32.7 (3)C6'—C1'—C2'—C3'70.2 (3)
C6—C1—C2—C371.9 (2)C7'—C1'—C2'—C3'−34.7 (3)
O4—C2—C3—C4178.5 (3)O4'—C2'—C3'—C4'−178.8 (3)
C1—C2—C3—C4−1.3 (3)C1'—C2'—C3'—C4'−0.2 (3)
C2—C3—C4—C5−72.1 (3)C2'—C3'—C4'—C5'−72.4 (3)
C2—C3—C4—C735.4 (3)C2'—C3'—C4'—C7'35.5 (3)
C3—C4—C5—C671.2 (2)C3'—C4'—C5'—C6'70.7 (3)
C7—C4—C5—C6−37.2 (2)C7'—C4'—C5'—C6'−36.3 (3)
C4—C5—C6—C12.5 (2)C4'—C5'—C6'—C1'2.4 (3)
C10—C1—C6—C5170.7 (2)C10'—C1'—C6'—C5'165.4 (3)
C2—C1—C6—C5−71.2 (2)C2'—C1'—C6'—C5'−71.2 (3)
C7—C1—C6—C532.7 (2)C7'—C1'—C6'—C5'31.7 (3)
C3—C4—C7—C9−175.0 (2)C5'—C4'—C7'—C8'172.5 (3)
C5—C4—C7—C9−64.9 (3)C3'—C4'—C7'—C8'62.3 (3)
C3—C4—C7—C861.9 (3)C5'—C4'—C7'—C9'−64.9 (3)
C5—C4—C7—C8172.0 (2)C3'—C4'—C7'—C9'−175.1 (2)
C3—C4—C7—C1−54.1 (3)C5'—C4'—C7'—C1'54.3 (2)
C5—C4—C7—C156.1 (2)C3'—C4'—C7'—C1'−55.8 (2)
C10—C1—C7—C9−70.6 (4)C10'—C1'—C7'—C8'57.0 (3)
C2—C1—C7—C9167.4 (2)C2'—C1'—C7'—C8'−63.2 (3)
C6—C1—C7—C962.8 (3)C6'—C1'—C7'—C8'−168.8 (2)
C10—C1—C7—C855.5 (3)C10'—C1'—C7'—C9'−68.1 (3)
C2—C1—C7—C8−66.5 (3)C2'—C1'—C7'—C9'171.7 (2)
C6—C1—C7—C8−171.1 (2)C6'—C1'—C7'—C9'66.1 (3)
C10—C1—C7—C4173.1 (3)C10'—C1'—C7'—C4'174.2 (2)
C2—C1—C7—C451.1 (3)C2'—C1'—C7'—C4'54.0 (2)
C6—C1—C7—C4−53.5 (2)C6'—C1'—C7'—C4'−51.5 (2)
C2—C1—C10—S174.2 (2)C2'—C1'—C10'—S'−142.1 (3)
C7—C1—C10—S55.8 (4)C6'—C1'—C10'—S'−22.6 (5)
C6—C1—C10—S−71.7 (3)C7'—C1'—C10'—S'103.6 (3)
O2—S—C10—C1−75.9 (3)O2'—S'—C10'—C1'−58.0 (3)
O3—S—C10—C1165.0 (3)O3'—S'—C10'—C1'−178.7 (3)
O1—S—C10—C144.9 (3)O1'—S'—C10'—C1'62.1 (3)
Acknowledgements top

The authors thank the Otto-von-Guericke-Universität for financial support of this work.

references
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