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Acta Cryst. (2008). E64, m1515    [ doi:10.1107/S1600536808035642 ]

(4-Hydroxymethyl-1H-imidazole-[kappa]N3)bis(tri-tert-butoxysilanethiolato-[kappa]2O,S)cadmium(II)

A. Dolega, K. Baranowska and Z. Jarzabek

Abstract top

The CdII atom in the title compound, [Cd(C12H27O3SSi)2(C4H6N2O)], is pentacoordinated by two O and two S atoms from the O,S-chelating silanethiolate residue and one N from the 4-hydroxymethylimidazole ligand and shows a strongly distorted trigonal-bipyramidal geometry. The title complex is isostructural with its zinc analog. The hydroxy group of the ligand is involved in intramolecular O-H...S hydrogen bonding and also acts as an acceptor in the formation of an intermolecular N-H...O hydrogen bond, which links molecules of the complex into zigzag chains parallel to the b axis. One of the tert-butyl groups is disordered over two orientations with occupancies of 0.557 (12):0.443 (12).

Comment top

We investigate structural and spectroscopic features of simple inorganic complexes - models of the catalytic site of the enzyme alcohol dehydrogenase. We use tri-tert- butoxysilanethiol as a source of thiolate function and substituted imidazoles as histidine analogs (Dołęga et al., 2008, and references therein)

Complex (I) is isostructural with (4-hydroxymethyl-1H- imidazole-κN)bis(tri-tert-butoxysilanethiolatoκ2:O,S)zinc(II) (Dołęga et al., 2008) thus the overall geometry, crystal packing and hydrogen bonds parameters in the title compound and its zinc analog are practically the same. The differences in metal-ligand bond lengths stem from the differences in zinc and cadmium radii. Additionally, the title complex shows a very large (> 140°) S—Cd—S angle, considerably larger than the respective angle in the zinc analog, a feature very characteristic of five-coordinated cadmium tri-tert-butoxysilanethiolates with CdNO2S2 kernels (Dołęga et al., 2006, Dołęga et al., 2007).

The molecular structure of (I) is shown in Fig. 1 and crystal packing diagram is presented in Fig.2.

Related literature top

For similar compounds, see: Dołęga et al. (2006, 2007, 2008). For the synthetic procedure, see: Wojnowski et al. (1992).

Experimental top

The title compound was prepared and crystallized by slow evaporation of solvent from toluene solution containing equimolar amounts of cadmium bis(tri-tert-butoxysilanethiolate) (Wojnowski et al. 1992) and 4(5)-hydroxymethylimidazole.

Refinement top

All C–H hydrogen atoms were refined as riding on carbon atoms with methyl C–H = 0.98 Å, methylene C–H = 0.99 Å, aromatic C–H = 0.95 Å and Uiso(H)=1.2 Ueq(C) for aromatic and methylene CH and 1.5Ueq(C) for methyl groups. H7D (OH) was found in the difference Fourier map and refined without constraints. Atoms C22—C24 are disordered over two positions (0.557 (12)/0.443 (12)). All atoms in the disordered tert-butyl group were set as isotropic (C21—C24). The voids of 61 Å3, present in the structure, are surrounded by tert-butyl groups and contain only insignificat residual electron density (the highest residual density in the void is 0.70 e/A3).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the title molecule, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms, except those from OH and NH groups, have been omitted. Hydrogen bonds are indicated with dashed lines. Only the major conformation for the disordered methyl groups (C24-C25) is shown.
[Figure 2] Fig. 2. A view of one-dimensional chains of molecules linked by hydrogen bonds along the c axis. All tBu groups have been omitted for clarity. Hydrogen bonds are indicated with dashed lines.
(4-Hydroxymethyl-1H-imidazole-κN3)bis(tri-tert- butoxysilanethiolato-κ2O,S)cadmium(II) top
Crystal data top
[Cd(C12H27O3SSi)2(C4H6N2O)]F(000) = 1624
Mr = 769.48Dx = 1.287 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25578 reflections
a = 16.3362 (4) Åθ = 2.0–32.5°
b = 9.1279 (2) ŵ = 0.75 mm−1
c = 26.6535 (6) ÅT = 120 K
β = 92.258 (2)°Prism, colourless
V = 3971.36 (16) Å30.13 × 0.10 × 0.06 mm
Z = 4
Data collection top
Oxford Diffraction KM-4-CCD
diffractometer		7385 independent reflections
graphite6448 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1Rint = 0.026
0.6° wide ω scansθmax = 25.5°, θmin = 2.0°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006)		h = −19→19
Tmin = 0.856, Tmax = 0.923k = −11→11
27726 measured reflectionsl = −32→31
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.14 w = 1/[σ2(Fo2) + (0.067P)2]
where P = (Fo2 + 2Fc2)/3
7385 reflections(Δ/σ)max = 0.001
376 parametersΔρmax = 1.14 e Å−3
0 restraintsΔρmin = −0.80 e Å−3
Crystal data top
[Cd(C12H27O3SSi)2(C4H6N2O)]V = 3971.36 (16) Å3
Mr = 769.48Z = 4
Monoclinic, P21/cMo Kα radiation
a = 16.3362 (4) ŵ = 0.75 mm−1
b = 9.1279 (2) ÅT = 120 K
c = 26.6535 (6) Å0.13 × 0.10 × 0.06 mm
β = 92.258 (2)°
Data collection top
Oxford Diffraction KM-4-CCD
diffractometer		7385 independent reflections
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006)		6448 reflections with I > 2σ(I)
Tmin = 0.856, Tmax = 0.923Rint = 0.026
27726 measured reflectionsθmax = 25.5°
Refinement top
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.096Δρmax = 1.14 e Å−3
S = 1.14Δρmin = −0.80 e Å−3
7385 reflectionsAbsolute structure: ?
376 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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*/UeqOcc. (<1)
C10.26185 (15)0.7084 (3)0.33154 (9)0.0242 (5)
C20.22265 (16)0.6933 (3)0.38215 (9)0.0295 (6)
H2A0.1630.6870.37710.044*
H2B0.23660.77880.4030.044*
H2C0.24310.60430.3990.044*
C30.35460 (16)0.7180 (3)0.33821 (12)0.0421 (7)
H3A0.36920.79970.36070.063*
H3B0.37840.7340.30550.063*
H3C0.37590.62640.35280.063*
C40.2371 (2)0.5823 (3)0.29714 (12)0.0403 (7)
H4A0.17720.57770.29350.06*
H4B0.2580.49020.31150.06*
H4C0.260.59750.26410.06*
C50.01249 (14)0.8699 (3)0.30993 (9)0.0238 (5)
C60.0257 (2)0.8463 (5)0.25496 (12)0.0602 (11)
H6A0.07090.7770.25110.09*
H6B0.03940.93990.23930.09*
H6C−0.02430.80670.23870.09*
C7−0.0044 (2)0.7254 (4)0.33537 (13)0.0545 (10)
H7A0.04120.65790.33030.082*
H7B−0.05510.6830.32090.082*
H7C−0.01030.74170.37140.082*
C8−0.0562 (2)0.9759 (4)0.31701 (18)0.0668 (12)
H8A−0.06380.99020.3530.1*
H8B−0.10670.93690.30110.1*
H8C−0.04291.06990.30160.1*
C90.18831 (15)1.1593 (3)0.40703 (9)0.0241 (5)
C100.1511 (2)1.0770 (3)0.45032 (11)0.0400 (7)
H10A0.19241.01180.4660.06*
H10B0.10431.01880.43760.06*
H10C0.13261.14730.47530.06*
C110.12555 (16)1.2614 (3)0.38198 (10)0.0314 (6)
H11A0.07731.2050.37070.047*
H11B0.14961.3090.35310.047*
H11C0.10941.33620.40610.047*
C120.26370 (16)1.2447 (3)0.42515 (10)0.0335 (6)
H12A0.30341.17760.44140.05*
H12B0.24781.31950.44930.05*
H12C0.28851.2920.39650.05*
C130.32921 (15)1.1821 (3)0.11528 (9)0.0246 (5)
C140.2878 (2)1.2913 (3)0.14824 (11)0.0392 (7)
H14A0.30641.27640.18330.059*
H14B0.22831.27770.14510.059*
H14C0.30171.39090.13780.059*
C150.42211 (17)1.1921 (3)0.12177 (12)0.0390 (7)
H15A0.44741.12040.09980.059*
H15B0.43871.17140.15680.059*
H15C0.441.29090.11290.059*
C160.30189 (18)1.2020 (3)0.06035 (10)0.0350 (6)
H16A0.32961.12980.03980.052*
H16B0.31611.3010.04940.052*
H16C0.24251.18820.05660.052*
C170.14114 (14)0.8571 (3)0.05674 (9)0.0264 (5)
C180.11468 (19)0.9139 (4)0.00481 (12)0.0495 (8)
H18A0.13940.8533−0.02090.074*
H18B0.13281.01560.00130.074*
H18C0.05490.90920.00070.074*
C190.11857 (17)0.6972 (3)0.06231 (12)0.0402 (7)
H19A0.14320.64010.03570.06*
H19B0.05890.68670.05980.06*
H19C0.13910.66130.09510.06*
C200.10348 (17)0.9486 (3)0.09720 (12)0.0398 (7)
H20A0.11871.05160.09290.06*
H20B0.12360.91430.13030.06*
H20C0.04370.93920.09460.06*
C210.41036 (15)0.7600 (3)0.03827 (10)0.0269 (5)*
C220.4994 (4)0.7341 (9)0.0418 (2)0.0366 (16)*0.557 (12)
H22A0.52830.82820.04170.055*0.557 (12)
H22B0.51560.67540.01310.055*0.557 (12)
H22C0.51360.68160.0730.055*0.557 (12)
C230.3867 (4)0.8458 (9)−0.0118 (2)0.0353 (15)*0.557 (12)
H23A0.32740.862−0.0140.053*0.557 (12)
H23B0.4030.788−0.04070.053*0.557 (12)
H23C0.41510.9404−0.01160.053*0.557 (12)
C240.3652 (4)0.6113 (6)0.0381 (2)0.0345 (16)*0.557 (12)
H24A0.3060.62810.03590.052*0.557 (12)
H24B0.37980.5580.0690.052*0.557 (12)
H24C0.38130.55350.00910.052*0.557 (12)
C22A0.5059 (4)0.7874 (10)0.0386 (3)0.0291 (18)*0.443 (12)
H22D0.53020.76220.07170.044*0.443 (12)
H22E0.51650.89090.03140.044*0.443 (12)
H22F0.53020.72620.01290.044*0.443 (12)
C23A0.3726 (5)0.7941 (11)−0.0107 (3)0.0321 (19)*0.443 (12)
H23D0.38490.8958−0.01950.048*0.443 (12)
H23E0.31310.7814−0.00950.048*0.443 (12)
H23F0.39420.7282−0.03590.048*0.443 (12)
C24A0.3960 (5)0.6023 (8)0.0563 (3)0.040 (2)*0.443 (12)
H24D0.42310.58830.08940.06*0.443 (12)
H24E0.41870.53320.03230.06*0.443 (12)
H24F0.33710.58480.05850.06*0.443 (12)
C250.46391 (14)0.9188 (3)0.22131 (9)0.0228 (5)
H250.45510.86110.19190.027*
C260.52586 (15)1.0311 (3)0.28461 (10)0.0248 (5)
H260.56691.06680.30770.03*
C270.44361 (14)1.0570 (2)0.28528 (9)0.0205 (5)
C280.39708 (14)1.1424 (3)0.32243 (9)0.0238 (5)
H28A0.35891.07570.33910.029*
H28B0.43611.18140.34850.029*
Cd10.273167 (9)0.943674 (18)0.220582 (6)0.01814 (8)
N10.40537 (11)0.9853 (2)0.24532 (7)0.0199 (4)
N20.53725 (13)0.9431 (2)0.24375 (9)0.0258 (5)
H20.58440.90890.2340.031*
O10.23479 (9)0.84275 (17)0.30576 (6)0.0207 (3)
O20.08452 (10)0.93091 (17)0.33613 (6)0.0220 (4)
O30.21789 (10)1.05130 (16)0.37210 (6)0.0199 (4)
O40.30355 (10)1.03704 (17)0.13302 (6)0.0214 (4)
O50.22966 (9)0.87083 (18)0.05928 (6)0.0214 (4)
O60.38600 (9)0.85444 (18)0.07826 (6)0.0235 (4)
O70.35133 (11)1.26197 (18)0.30055 (7)0.0249 (4)
S10.18152 (3)1.12091 (6)0.25939 (2)0.01828 (13)
S20.27794 (4)0.73133 (6)0.16373 (2)0.02216 (14)
Si10.17558 (4)0.97987 (7)0.32161 (2)0.01673 (14)
Si20.29845 (4)0.87600 (7)0.10490 (2)0.01808 (14)
H7D0.3073 (18)1.230 (3)0.2908 (11)0.032 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0289 (13)0.0189 (12)0.0246 (13)0.0058 (10)0.0011 (10)0.0068 (10)
C20.0374 (14)0.0285 (14)0.0228 (13)0.0034 (11)0.0033 (11)0.0067 (11)
C30.0305 (15)0.0423 (17)0.0537 (19)0.0115 (13)0.0052 (13)0.0252 (15)
C40.070 (2)0.0199 (13)0.0316 (16)0.0063 (13)0.0060 (14)0.0035 (12)
C50.0174 (11)0.0277 (13)0.0262 (13)−0.0069 (10)0.0006 (9)0.0011 (10)
C60.0413 (18)0.104 (3)0.0351 (18)−0.039 (2)0.0027 (14)−0.0169 (19)
C70.0508 (19)0.049 (2)0.061 (2)−0.0304 (16)−0.0249 (16)0.0225 (17)
C80.0348 (18)0.055 (2)0.108 (3)0.0125 (16)−0.025 (2)−0.025 (2)
C90.0268 (13)0.0268 (13)0.0190 (12)−0.0028 (10)0.0055 (10)−0.0072 (10)
C100.0499 (18)0.0429 (17)0.0283 (15)−0.0050 (14)0.0163 (13)0.0008 (13)
C110.0331 (14)0.0291 (14)0.0319 (15)0.0023 (11)0.0015 (11)−0.0098 (11)
C120.0352 (15)0.0379 (15)0.0272 (14)−0.0035 (12)0.0009 (11)−0.0117 (12)
C130.0366 (14)0.0151 (11)0.0223 (13)−0.0049 (10)0.0042 (10)0.0033 (10)
C140.0596 (19)0.0186 (13)0.0402 (17)−0.0046 (13)0.0145 (14)−0.0015 (12)
C150.0404 (16)0.0299 (15)0.0466 (18)−0.0127 (12)0.0011 (13)0.0064 (13)
C160.0544 (18)0.0249 (14)0.0254 (14)−0.0051 (12)−0.0007 (12)0.0069 (11)
C170.0173 (12)0.0373 (15)0.0247 (13)0.0020 (10)0.0023 (9)−0.0056 (11)
C180.0286 (15)0.083 (2)0.0361 (17)0.0086 (16)−0.0062 (13)0.0082 (17)
C190.0319 (15)0.0428 (17)0.0459 (18)−0.0100 (13)0.0021 (13)−0.0115 (14)
C200.0256 (14)0.0496 (19)0.0447 (18)0.0052 (12)0.0082 (12)−0.0174 (14)
C250.0219 (12)0.0215 (12)0.0253 (13)0.0008 (9)0.0036 (10)−0.0024 (10)
C260.0195 (12)0.0224 (12)0.0324 (14)−0.0008 (9)−0.0011 (10)−0.0014 (10)
C270.0188 (12)0.0198 (12)0.0229 (13)−0.0020 (9)0.0007 (9)0.0036 (9)
C280.0199 (12)0.0270 (13)0.0243 (13)−0.0017 (10)0.0001 (9)−0.0031 (10)
Cd10.01793 (11)0.01975 (12)0.01684 (11)0.00073 (6)0.00194 (7)−0.00169 (6)
N10.0179 (10)0.0200 (10)0.0217 (10)0.0015 (8)0.0020 (8)0.0005 (8)
N20.0174 (10)0.0237 (11)0.0366 (13)0.0030 (8)0.0048 (9)0.0001 (9)
O10.0246 (8)0.0175 (8)0.0202 (8)0.0042 (7)0.0029 (6)0.0038 (7)
O20.0192 (8)0.0248 (9)0.0223 (9)−0.0067 (6)0.0031 (7)−0.0003 (7)
O30.0196 (8)0.0216 (9)0.0186 (8)−0.0008 (6)0.0004 (7)−0.0019 (6)
O40.0298 (9)0.0154 (8)0.0192 (9)−0.0034 (7)0.0046 (7)0.0011 (6)
O50.0194 (8)0.0263 (9)0.0186 (8)−0.0003 (7)0.0013 (6)−0.0020 (7)
O60.0215 (8)0.0284 (9)0.0207 (9)−0.0007 (7)0.0028 (7)−0.0048 (7)
O70.0186 (9)0.0203 (9)0.0361 (10)−0.0023 (7)0.0049 (7)−0.0036 (7)
S10.0180 (3)0.0178 (3)0.0192 (3)0.0024 (2)0.0022 (2)0.0024 (2)
S20.0313 (3)0.0164 (3)0.0190 (3)−0.0008 (2)0.0029 (2)0.0002 (2)
Si10.0153 (3)0.0172 (3)0.0179 (3)−0.0018 (2)0.0027 (2)−0.0009 (2)
Si20.0209 (3)0.0174 (3)0.0160 (3)−0.0005 (2)0.0023 (2)−0.0008 (2)
Geometric parameters (Å, °) top
C1—O11.466 (3)C18—H18C0.98
C1—C41.517 (4)C19—H19A0.98
C1—C31.521 (4)C19—H19B0.98
C1—C21.522 (3)C19—H19C0.98
C2—H2A0.98C20—H20A0.98
C2—H2B0.98C20—H20B0.98
C2—H2C0.98C20—H20C0.98
C3—H3A0.98C21—O61.439 (3)
C3—H3B0.98C21—C23A1.454 (7)
C3—H3C0.98C21—C221.473 (6)
C4—H4A0.98C21—C24A1.539 (8)
C4—H4B0.98C21—C241.545 (6)
C4—H4C0.98C21—C22A1.580 (7)
C5—O21.455 (3)C21—C231.581 (7)
C5—C81.499 (4)C22—H22A0.98
C5—C61.505 (4)C22—H22B0.98
C5—C71.513 (4)C22—H22C0.98
C6—H6A0.98C23—H23A0.98
C6—H6B0.98C23—H23B0.98
C6—H6C0.98C23—H23C0.98
C7—H7A0.98C24—H24A0.98
C7—H7B0.98C24—H24B0.98
C7—H7C0.98C24—H24C0.98
C8—H8A0.98C22A—H22D0.98
C8—H8B0.98C22A—H22E0.98
C8—H8C0.98C22A—H22F0.98
C9—O31.452 (3)C23A—H23D0.98
C9—C121.520 (3)C23A—H23E0.98
C9—C111.521 (4)C23A—H23F0.98
C9—C101.523 (4)C24A—H24D0.98
C10—H10A0.98C24A—H24E0.98
C10—H10B0.98C24A—H24F0.98
C10—H10C0.98C25—N11.319 (3)
C11—H11A0.98C25—N21.336 (3)
C11—H11B0.98C25—H250.95
C11—H11C0.98C26—C271.365 (3)
C12—H12A0.98C26—N21.372 (3)
C12—H12B0.98C26—H260.95
C12—H12C0.98C27—N11.378 (3)
C13—O41.472 (3)C27—C281.492 (3)
C13—C141.507 (4)C28—O71.433 (3)
C13—C151.523 (4)C28—H28A0.99
C13—C161.525 (3)C28—H28B0.99
C14—H14A0.98Cd1—N12.2653 (19)
C14—H14B0.98Cd1—S12.4599 (6)
C14—H14C0.98Cd1—S22.4633 (6)
C15—H15A0.98Cd1—O12.5511 (16)
C15—H15B0.98Cd1—O42.5516 (16)
C15—H15C0.98N2—H20.88
C16—H16A0.98O1—Si11.6471 (16)
C16—H16B0.98O2—Si11.6147 (17)
C16—H16C0.98O3—Si11.6250 (17)
C17—O51.450 (3)O4—Si21.6505 (17)
C17—C201.514 (4)O5—Si21.6236 (16)
C17—C191.514 (4)O6—Si21.6335 (17)
C17—C181.524 (4)O7—H7D0.81 (3)
C18—H18A0.98S1—Si12.1047 (8)
C18—H18B0.98S2—Si22.0872 (8)
O1—C1—C4106.44 (19)C17—C20—H20B109.5
O1—C1—C3106.70 (19)H20A—C20—H20B109.5
C4—C1—C3110.8 (2)C17—C20—H20C109.5
O1—C1—C2111.21 (19)H20A—C20—H20C109.5
C4—C1—C2110.8 (2)H20B—C20—H20C109.5
C3—C1—C2110.7 (2)O6—C21—C23A114.6 (4)
C1—C2—H2A109.5O6—C21—C22110.5 (3)
C1—C2—H2B109.5C23A—C21—C22118.4 (4)
H2A—C2—H2B109.5O6—C21—C24A106.2 (3)
C1—C2—H2C109.5C23A—C21—C24A114.5 (5)
H2A—C2—H2C109.5C22—C21—C24A89.6 (4)
H2B—C2—H2C109.5O6—C21—C24112.5 (3)
C1—C3—H3A109.5C23A—C21—C2490.0 (4)
C1—C3—H3B109.5C22—C21—C24109.2 (4)
H3A—C3—H3B109.5O6—C21—C22A101.7 (3)
C1—C3—H3C109.5C23A—C21—C22A110.8 (4)
H3A—C3—H3C109.5C24A—C21—C22A108.0 (4)
H3B—C3—H3C109.5C24—C21—C22A127.6 (4)
C1—C4—H4A109.5O6—C21—C23105.3 (3)
C1—C4—H4B109.5C22—C21—C23110.0 (4)
H4A—C4—H4B109.5C24A—C21—C23133.7 (4)
C1—C4—H4C109.5C24—C21—C23109.4 (4)
H4A—C4—H4C109.5C22A—C21—C2397.7 (4)
H4B—C4—H4C109.5C21—C22—H22A109.5
O2—C5—C8106.7 (2)C21—C22—H22B109.5
O2—C5—C6112.2 (2)H22A—C22—H22B109.5
C8—C5—C6110.6 (3)C21—C22—H22C109.5
O2—C5—C7106.1 (2)H22A—C22—H22C109.5
C8—C5—C7110.8 (3)H22B—C22—H22C109.5
C6—C5—C7110.3 (3)C21—C23—H23A109.5
C5—C6—H6A109.5C21—C23—H23B109.5
C5—C6—H6B109.5H23A—C23—H23B109.5
H6A—C6—H6B109.5C21—C23—H23C109.5
C5—C6—H6C109.5H23A—C23—H23C109.5
H6A—C6—H6C109.5H23B—C23—H23C109.5
H6B—C6—H6C109.5C21—C24—H24A109.5
C5—C7—H7A109.5C21—C24—H24B109.5
C5—C7—H7B109.5H24A—C24—H24B109.5
H7A—C7—H7B109.5C21—C24—H24C109.5
C5—C7—H7C109.5H24A—C24—H24C109.5
H7A—C7—H7C109.5H24B—C24—H24C109.5
H7B—C7—H7C109.5C21—C22A—H22D109.5
C5—C8—H8A109.5C21—C22A—H22E109.5
C5—C8—H8B109.5H22D—C22A—H22E109.5
H8A—C8—H8B109.5C21—C22A—H22F109.5
C5—C8—H8C109.5H22D—C22A—H22F109.5
H8A—C8—H8C109.5H22E—C22A—H22F109.5
H8B—C8—H8C109.5C21—C23A—H23D109.5
O3—C9—C12105.42 (19)C21—C23A—H23E109.5
O3—C9—C11111.74 (19)H23D—C23A—H23E109.5
C12—C9—C11110.4 (2)C21—C23A—H23F109.5
O3—C9—C10107.7 (2)H23D—C23A—H23F109.5
C12—C9—C10110.8 (2)H23E—C23A—H23F109.5
C11—C9—C10110.7 (2)C21—C24A—H24D109.5
C9—C10—H10A109.5C21—C24A—H24E109.5
C9—C10—H10B109.5H24D—C24A—H24E109.5
H10A—C10—H10B109.5C21—C24A—H24F109.5
C9—C10—H10C109.5H24D—C24A—H24F109.5
H10A—C10—H10C109.5H24E—C24A—H24F109.5
H10B—C10—H10C109.5N1—C25—N2111.1 (2)
C9—C11—H11A109.5N1—C25—H25124.4
C9—C11—H11B109.5N2—C25—H25124.4
H11A—C11—H11B109.5C27—C26—N2106.0 (2)
C9—C11—H11C109.5C27—C26—H26127
H11A—C11—H11C109.5N2—C26—H26127
H11B—C11—H11C109.5C26—C27—N1108.9 (2)
C9—C12—H12A109.5C26—C27—C28128.8 (2)
C9—C12—H12B109.5N1—C27—C28122.3 (2)
H12A—C12—H12B109.5O7—C28—C27113.51 (19)
C9—C12—H12C109.5O7—C28—H28A108.9
H12A—C12—H12C109.5C27—C28—H28A108.9
H12B—C12—H12C109.5O7—C28—H28B108.9
O4—C13—C14105.52 (19)C27—C28—H28B108.9
O4—C13—C15108.2 (2)H28A—C28—H28B107.7
C14—C13—C15111.2 (2)N1—Cd1—S1110.88 (5)
O4—C13—C16109.86 (19)N1—Cd1—S2104.96 (5)
C14—C13—C16111.1 (2)S1—Cd1—S2144.16 (2)
C15—C13—C16110.8 (2)N1—Cd1—O193.81 (6)
C13—C14—H14A109.5S1—Cd1—O171.84 (4)
C13—C14—H14B109.5S2—Cd1—O1106.15 (4)
H14A—C14—H14B109.5N1—Cd1—O489.58 (6)
C13—C14—H14C109.5S1—Cd1—O4107.97 (4)
H14A—C14—H14C109.5S2—Cd1—O471.83 (4)
H14B—C14—H14C109.5O1—Cd1—O4176.43 (5)
C13—C15—H15A109.5C25—N1—C27106.15 (19)
C13—C15—H15B109.5C25—N1—Cd1118.84 (16)
H15A—C15—H15B109.5C27—N1—Cd1134.62 (16)
C13—C15—H15C109.5C25—N2—C26107.8 (2)
H15A—C15—H15C109.5C25—N2—H2126.1
H15B—C15—H15C109.5C26—N2—H2126.1
C13—C16—H16A109.5C1—O1—Si1133.23 (14)
C13—C16—H16B109.5C1—O1—Cd1129.74 (13)
H16A—C16—H16B109.5Si1—O1—Cd196.97 (7)
C13—C16—H16C109.5C5—O2—Si1136.55 (15)
H16A—C16—H16C109.5C9—O3—Si1131.46 (15)
H16B—C16—H16C109.5C13—O4—Si2131.67 (15)
O5—C17—C20110.6 (2)C13—O4—Cd1131.47 (13)
O5—C17—C19109.0 (2)Si2—O4—Cd196.30 (7)
C20—C17—C19110.8 (2)C17—O5—Si2134.18 (14)
O5—C17—C18105.0 (2)C21—O6—Si2131.80 (15)
C20—C17—C18110.5 (2)C28—O7—H7D108 (2)
C19—C17—C18110.8 (2)Si1—S1—Cd188.67 (3)
C17—C18—H18A109.5Si2—S2—Cd188.52 (3)
C17—C18—H18B109.5O2—Si1—O3106.16 (9)
H18A—C18—H18B109.5O2—Si1—O1114.02 (9)
C17—C18—H18C109.5O3—Si1—O1106.40 (9)
H18A—C18—H18C109.5O2—Si1—S1115.45 (7)
H18B—C18—H18C109.5O3—Si1—S1112.07 (7)
C17—C19—H19A109.5O1—Si1—S1102.53 (6)
C17—C19—H19B109.5O5—Si2—O6105.25 (8)
H19A—C19—H19B109.5O5—Si2—O4112.77 (9)
C17—C19—H19C109.5O6—Si2—O4105.98 (9)
H19A—C19—H19C109.5O5—Si2—S2114.67 (7)
H19B—C19—H19C109.5O6—Si2—S2114.80 (7)
C17—C20—H20A109.5O4—Si2—S2103.24 (7)
N2—C26—C27—N10.1 (3)S2—Cd1—O4—Si22.44 (6)
N2—C26—C27—C28178.1 (2)C20—C17—O5—Si241.1 (3)
C26—C27—C28—O7121.6 (3)C19—C17—O5—Si2−80.9 (3)
N1—C27—C28—O7−60.7 (3)C18—C17—O5—Si2160.4 (2)
N2—C25—N1—C270.3 (3)C23A—C21—O6—Si267.3 (5)
N2—C25—N1—Cd1−173.57 (15)C22—C21—O6—Si2−155.9 (4)
C26—C27—N1—C25−0.3 (3)C24A—C21—O6—Si2−60.2 (4)
C28—C27—N1—C25−178.4 (2)C24—C21—O6—Si2−33.6 (4)
C26—C27—N1—Cd1172.21 (17)C22A—C21—O6—Si2−173.1 (4)
C28—C27—N1—Cd1−5.9 (3)C23—C21—O6—Si285.4 (4)
S1—Cd1—N1—C25−167.65 (16)N1—Cd1—S1—Si1−87.21 (6)
S2—Cd1—N1—C2512.51 (19)S2—Cd1—S1—Si192.52 (4)
O1—Cd1—N1—C25120.35 (18)O1—Cd1—S1—Si1−0.09 (4)
O4—Cd1—N1—C25−58.54 (18)O4—Cd1—S1—Si1176.16 (4)
S1—Cd1—N1—C2720.6 (2)N1—Cd1—S2—Si2−86.42 (6)
S2—Cd1—N1—C27−159.2 (2)S1—Cd1—S2—Si293.83 (4)
O1—Cd1—N1—C27−51.4 (2)O1—Cd1—S2—Si2175.01 (4)
O4—Cd1—N1—C27129.7 (2)O4—Cd1—S2—Si2−1.92 (4)
N1—C25—N2—C26−0.3 (3)C5—O2—Si1—O3175.4 (2)
C27—C26—N2—C250.1 (3)C5—O2—Si1—O1−67.8 (2)
C4—C1—O1—Si1124.2 (2)C5—O2—Si1—S150.6 (2)
C3—C1—O1—Si1−117.5 (2)C9—O3—Si1—O2−47.8 (2)
C2—C1—O1—Si13.4 (3)C9—O3—Si1—O1−169.64 (18)
C4—C1—O1—Cd1−59.4 (2)C9—O3—Si1—S179.05 (19)
C3—C1—O1—Cd159.0 (3)C1—O1—Si1—O2−57.3 (2)
C2—C1—O1—Cd1179.85 (14)Cd1—O1—Si1—O2125.37 (8)
N1—Cd1—O1—C1−66.57 (18)C1—O1—Si1—O359.3 (2)
S1—Cd1—O1—C1−177.30 (18)Cd1—O1—Si1—O3−117.96 (8)
S2—Cd1—O1—C140.21 (17)C1—O1—Si1—S1177.14 (18)
N1—Cd1—O1—Si1110.85 (8)Cd1—O1—Si1—S1−0.14 (6)
S1—Cd1—O1—Si10.12 (5)Cd1—S1—Si1—O2−124.43 (7)
S2—Cd1—O1—Si1−142.37 (6)Cd1—S1—Si1—O3113.86 (7)
C8—C5—O2—Si1−121.4 (3)Cd1—S1—Si1—O10.14 (6)
C6—C5—O2—Si1−0.2 (4)C17—O5—Si2—O6167.1 (2)
C7—C5—O2—Si1120.3 (3)C17—O5—Si2—O4−77.9 (2)
C12—C9—O3—Si1−146.96 (18)C17—O5—Si2—S239.9 (2)
C11—C9—O3—Si1−27.0 (3)C21—O6—Si2—O5−40.8 (2)
C10—C9—O3—Si194.7 (2)C21—O6—Si2—O4−160.5 (2)
C14—C13—O4—Si2156.53 (19)C21—O6—Si2—S286.2 (2)
C15—C13—O4—Si2−84.3 (3)C13—O4—Si2—O5−66.5 (2)
C16—C13—O4—Si236.7 (3)Cd1—O4—Si2—O5121.51 (8)
C14—C13—O4—Cd1−34.2 (3)C13—O4—Si2—O648.1 (2)
C15—C13—O4—Cd185.0 (2)Cd1—O4—Si2—O6−123.85 (8)
C16—C13—O4—Cd1−153.95 (17)C13—O4—Si2—S2169.15 (19)
N1—Cd1—O4—C13−63.63 (19)Cd1—O4—Si2—S2−2.81 (7)
S1—Cd1—O4—C1348.22 (19)Cd1—S2—Si2—O5−120.17 (7)
S2—Cd1—O4—C13−169.54 (19)Cd1—S2—Si2—O6117.74 (7)
N1—Cd1—O4—Si2108.35 (8)Cd1—S2—Si2—O42.90 (7)
S1—Cd1—O4—Si2−139.79 (6)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O7i0.881.962.759 (3)151
O7—H7D···S10.81 (3)2.41 (3)3.2119 (19)176 (3)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2.
Table 1
Selected geometric parameters (Å, °) top
Cd1—N12.2653 (19)Cd1—O42.5516 (16)
Cd1—S12.4599 (6)S1—Si12.1047 (8)
Cd1—S22.4633 (6)S2—Si22.0872 (8)
Cd1—O12.5511 (16)
N1—Cd1—S1110.88 (5)S1—Cd1—O171.84 (4)
S1—Cd1—S2144.16 (2)O1—Cd1—O4176.43 (5)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O7i0.881.962.759 (3)151
O7—H7D···S10.81 (3)2.41 (3)3.2119 (19)176 (3)
Symmetry codes: (i) −x+1, y−1/2, −z+1/2.
Acknowledgements top

The work was undertaken with financial support from the Polish Ministry of Science and Higher Education (grant No. N N204 274835).

references
References top

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