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Acta Cryst. (2007). E63, m1774    [ doi:10.1107/S1600536807025500 ]

(2-Ethylimidazole-[kappa]N)bis(tri-tert-butoxysilanethiolato-[kappa]2O,S)zinc(II) propan-2-ol solvate

A. Dolega, M. Wieczerzak and K. Baranowska

Abstract top

In the title compound, [Zn(C12H27O3SSi)2(C5H8N2)]·C3H8O, the ZnII centre is coordinated by the N atom of the 2-ethylimidazole ligand and two S and two O atoms of the two thiolate ligands in a trigonal-bipyramidal geometry. The hydroxyl group of the propan-2-ol solvent molecule forms N-H...O and O-H...S hydrogen bonds with adjacent molecules, linking them into chains.

Comment top

The geometry of coordinating atoms in the molecule of the title complex, (I) (Fig. 1), may be approximated to distorted trigonal bipyramidal.The central atom of zinc is coordinated by five atoms; two sulfur S1, S2, one nitrogen N1 and two oxygen atoms O1 and O4 (Fig. 1). The basal trigonal plane is formed by atoms Zn1, S1, S2 and N1; Zn1 deviates from the plane at the O4 side by 0.0460 (5) Å and it is the most deviating atom. The O1 and O4 atoms occupy two apical positions. The perpendicular distances between O1, O4 and plane Zn1—S1—S2—N1 are 2.4134 (14) Å and 2.3701 (13) Å respectively. Complexation of O1 and O4 with zinc is reflected in the respective Si—O bond lengths: Si1—O1 and Si2—O4 are definitely longer then the rest of Si—O bonds.

Molecules of zinc thiolate and 2-propanol are linked via N—H···O and O—H···S hydrogen bonds to generate antiparallel chains along the c axis, as shown in Fig. 2. The tert-butyl groups on both sides of each chain prevent other interactions than hydrophobic between the chains.

The analogous penta-coordinated complex with 1-methylimidazole (which has a blocked N—H function) also has a tbp geometry (Dołęga Anna et al., 2004) but the molecules pack in crystal as discrete units.

Related literature top

For an analogous compound with 1-methylimidazole, see Dołęga et al. (2004).

Experimental top

The title compound crystallized from acetonitrile and 2-propanol solution of equimolar quantities of zinc acetyloacetonate, tri-tert-butoxysilanethiol and 2-ethylimidazole at 255 K.

Refinement top

All H atoms were positioned geometrically and refined using riding model with C—H distances of 0.93 and with isotropic temperature factors Uiso 1.2 times the equivalent isotropic temperature factors Ueq of their attached atoms.

Computing details top

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

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms. H-atoms of tert-butyl groups have been omitted.
[Figure 2] Fig. 2. The packing of (I) viewed approximately down the c axis. The antiparallel chains connected by O—H···S and N—H···O hydrogen bonds (dashed lines) are shown. All tert-butyl groups have been omitted as are most H-atoms. Symmetry codes: i: x - 1,y,z; ii: -x,-y + 2,-z; iii: -x - 1,-y + 2,-z
(2-Ethylimidazole-κN)bis(tri-tert-butoxysilanethiolato-κ2O,S)zinc(II) propan-2-ol solvate top
Crystal data top
[Zn(C12H27O3SSi)2(C5H8N2)]·C3H8OF(000) = 1688
Mr = 780.57Dx = 1.161 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 26429 reflections
a = 9.8958 (2) Åθ = 2.2–32.3°
b = 25.3673 (6) ŵ = 0.74 mm−1
c = 19.8040 (5) ÅT = 120 K
β = 116.064 (2)°Prism, colourless
V = 4465.82 (18) Å30.32 × 0.16 × 0.09 mm
Z = 4
Data collection top
Oxford Diffraction KM-4-CCD κ-geometry
diffractometer		7709 independent reflections
graphite6892 reflections with I > 2σ(I)
Detector resolution: 8.1883 pixels mm-1Rint = 0.018
ω scans, 0.75° widthθmax = 25.1°, θmin = 2.2°
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006)		h = −11→11
Tmin = 0.769, Tmax = 0.885k = −29→30
25240 measured reflectionsl = −23→16
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)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096H-atom parameters constrained
S = 1.13 w = 1/[σ2(Fo2) + (0.0555P)2 + 1.9663P]
where P = (Fo2 + 2Fc2)/3
7709 reflections(Δ/σ)max = 0.002
436 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −0.32 e Å−3
Crystal data top
[Zn(C12H27O3SSi)2(C5H8N2)]·C3H8OV = 4465.82 (18) Å3
Mr = 780.57Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.8958 (2) ŵ = 0.74 mm−1
b = 25.3673 (6) ÅT = 120 K
c = 19.8040 (5) Å0.32 × 0.16 × 0.09 mm
β = 116.064 (2)°
Data collection top
Oxford Diffraction KM-4-CCD κ-geometry
diffractometer		7709 independent reflections
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2006)		6892 reflections with I > 2σ(I)
Tmin = 0.769, Tmax = 0.885Rint = 0.018
25240 measured reflectionsθmax = 25.1°
Refinement top
R[F2 > 2σ(F2)] = 0.034H-atom parameters constrained
wR(F2) = 0.096Δρmax = 0.43 e Å−3
S = 1.13Δρmin = −0.32 e Å−3
7709 reflectionsAbsolute structure: ?
436 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*/Ueq
Zn10.11065 (2)0.858298 (9)0.168011 (12)0.02689 (9)
S1−0.14032 (5)0.838733 (18)0.11807 (3)0.02538 (12)
S20.27814 (6)0.866765 (19)0.29095 (3)0.02821 (12)
Si1−0.09197 (6)0.75822 (2)0.12344 (3)0.02343 (13)
Si20.22006 (6)0.94624 (2)0.28076 (3)0.02166 (12)
O10.09257 (15)0.75833 (5)0.15834 (8)0.0287 (3)
O2−0.15485 (17)0.72856 (5)0.04283 (8)0.0306 (3)
O3−0.15266 (17)0.72450 (5)0.17437 (8)0.0303 (3)
O40.09130 (14)0.95017 (5)0.19224 (7)0.0226 (3)
O50.16053 (15)0.96744 (5)0.34042 (8)0.0283 (3)
O60.35044 (15)0.98787 (5)0.28657 (7)0.0247 (3)
N10.17911 (19)0.86101 (6)0.08619 (10)0.0274 (4)
N20.3103 (2)0.86372 (7)0.02171 (10)0.0350 (4)
H20.38550.8690.01020.042*
C10.1993 (3)0.71605 (9)0.16691 (14)0.0388 (5)
C20.3435 (3)0.73192 (11)0.23355 (16)0.0534 (7)
H2A0.37380.76710.22480.064*
H2B0.42280.70650.240.064*
H2C0.32750.73250.2790.064*
C30.2208 (4)0.71335 (12)0.09567 (16)0.0575 (7)
H3A0.12390.70620.05260.069*
H3B0.29190.68510.10030.069*
H3C0.26050.74710.0880.069*
C40.1415 (3)0.66356 (10)0.18129 (17)0.0538 (7)
H4A0.12120.66680.22530.065*
H4B0.21760.63620.19060.065*
H4C0.04860.65390.13730.065*
C5−0.2955 (3)0.70240 (9)−0.00344 (12)0.0383 (5)
C6−0.4276 (3)0.73258 (12)−0.00333 (16)0.0556 (7)
H6A−0.42150.73230.04740.067*
H6B−0.52180.7159−0.03830.067*
H6C−0.42490.7691−0.0190.067*
C7−0.2893 (4)0.64690 (10)0.02595 (17)0.0646 (9)
H7A−0.20120.62860.02690.078*
H7B−0.38080.6278−0.0070.078*
H7C−0.28170.64830.07690.078*
C8−0.3043 (3)0.70145 (11)−0.08191 (13)0.0487 (6)
H8A−0.30560.7377−0.09940.058*
H8B−0.39640.6833−0.11620.058*
H8C−0.21660.6828−0.08080.058*
C9−0.1582 (3)0.73539 (9)0.24493 (12)0.0355 (5)
C10−0.0101 (3)0.75815 (10)0.30176 (13)0.0428 (6)
H10A0.07150.73340.30940.051*
H10B−0.01490.7640.34960.051*
H10C0.00880.79170.2830.051*
C11−0.2876 (3)0.77313 (11)0.23045 (15)0.0494 (6)
H11A−0.26520.80750.21520.059*
H11B−0.30050.77720.27650.059*
H11C−0.38030.7590.19040.059*
C12−0.1868 (4)0.68200 (11)0.27136 (15)0.0555 (7)
H12A−0.28460.66840.23510.067*
H12B−0.18690.68590.32060.067*
H12C−0.10750.65730.27540.067*
C130.0247 (2)0.99659 (7)0.14529 (11)0.0264 (4)
C140.1271 (3)1.01286 (10)0.10996 (13)0.0399 (5)
H14A0.22631.02230.14960.048*
H14B0.08361.04330.07710.048*
H14C0.13740.98350.08040.048*
C15−0.1274 (2)0.97845 (8)0.08538 (11)0.0302 (4)
H15A−0.1130.94930.05680.036*
H15B−0.17731.00780.05130.036*
H15C−0.190.96660.10950.036*
C160.0056 (3)1.04084 (8)0.19196 (13)0.0374 (5)
H16A−0.0581.02870.21530.045*
H16B−0.04191.07120.15950.045*
H16C0.10431.05120.23120.045*
C170.0593 (3)0.94675 (10)0.36897 (12)0.0361 (5)
C18−0.0770 (3)0.92107 (11)0.30563 (13)0.0432 (6)
H18A−0.12720.94680.26530.052*
H18B−0.14740.90910.32510.052*
H18C−0.04410.89080.28580.052*
C190.1431 (3)0.90773 (12)0.43099 (14)0.0530 (7)
H19A0.1750.87770.41040.064*
H19B0.0770.89540.45280.064*
H19C0.23180.92480.47010.064*
C200.0106 (3)0.99499 (12)0.39924 (15)0.0511 (7)
H20A0.09941.01190.43860.061*
H20B−0.05790.98390.42030.061*
H20C−0.04091.02010.35820.061*
C210.4762 (2)1.01019 (8)0.35030 (11)0.0266 (4)
C220.4187 (3)1.05600 (10)0.38037 (15)0.0447 (6)
H22A0.36761.08160.340.054*
H22B0.50361.07310.42170.054*
H22C0.34791.04270.39870.054*
C230.5826 (3)1.03099 (12)0.32033 (15)0.0506 (6)
H23A0.61871.00170.30040.061*
H23B0.66841.04820.3610.061*
H23C0.52981.05650.28020.061*
C240.5511 (3)0.96889 (10)0.40965 (14)0.0490 (6)
H24A0.47880.95520.42670.059*
H24B0.63680.98460.45230.059*
H24C0.58650.940.38860.059*
C250.0917 (2)0.84240 (9)0.01462 (12)0.0343 (5)
H25−0.00910.8304−0.00350.041*
C260.1718 (3)0.84400 (9)−0.02545 (13)0.0378 (5)
H260.13880.8335−0.07630.045*
C270.3117 (2)0.87356 (8)0.08902 (12)0.0318 (5)
C280.4440 (3)0.89577 (12)0.15449 (14)0.0539 (7)
H28A0.41240.90550.19380.065*
H28B0.52150.86790.17550.065*
C290.5123 (4)0.94198 (12)0.13745 (17)0.0628 (8)
H29A0.54090.93330.09730.075*
H29B0.6020.95250.18260.075*
H29C0.43980.97110.12110.075*
O70.54940 (18)0.62127 (8)0.48632 (9)0.0447 (4)
H70.63680.63080.51620.054*
C300.5533 (2)0.59525 (9)0.42315 (12)0.0328 (5)
H300.61210.56180.44050.039*
C310.6262 (3)0.62962 (10)0.38684 (14)0.0424 (6)
H31A0.7290.63810.42350.051*
H31B0.56820.66230.36920.051*
H31C0.62880.61090.34410.051*
C320.3924 (3)0.58204 (11)0.37114 (14)0.0456 (6)
H32A0.33430.61470.35380.055*
H32B0.34950.56050.3980.055*
H32C0.38880.56230.32780.055*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02290 (14)0.03310 (15)0.02241 (14)−0.00520 (9)0.00787 (11)−0.00236 (9)
S10.0221 (2)0.0231 (2)0.0275 (3)−0.00115 (18)0.0077 (2)−0.00005 (18)
S20.0275 (3)0.0241 (2)0.0242 (3)0.00294 (19)0.0032 (2)0.00118 (18)
Si10.0273 (3)0.0212 (3)0.0222 (3)−0.0029 (2)0.0113 (2)−0.0008 (2)
Si20.0200 (3)0.0229 (3)0.0185 (3)0.0002 (2)0.0052 (2)−0.00069 (19)
O10.0280 (8)0.0257 (7)0.0315 (8)0.0033 (6)0.0122 (7)0.0012 (6)
O20.0374 (8)0.0301 (7)0.0256 (8)−0.0085 (6)0.0149 (7)−0.0053 (6)
O30.0419 (9)0.0269 (7)0.0258 (7)−0.0070 (6)0.0182 (7)−0.0018 (6)
O40.0201 (7)0.0216 (6)0.0203 (7)0.0012 (5)0.0036 (6)0.0016 (5)
O50.0269 (7)0.0346 (8)0.0237 (7)−0.0022 (6)0.0113 (6)−0.0037 (6)
O60.0219 (7)0.0277 (7)0.0198 (7)−0.0025 (5)0.0048 (6)−0.0009 (5)
N10.0251 (9)0.0285 (9)0.0267 (9)−0.0032 (7)0.0096 (8)−0.0008 (7)
N20.0300 (10)0.0440 (11)0.0345 (10)−0.0017 (8)0.0174 (9)0.0028 (8)
C10.0382 (13)0.0324 (11)0.0470 (14)0.0135 (10)0.0198 (11)0.0051 (10)
C20.0346 (14)0.0544 (16)0.0619 (18)0.0154 (12)0.0127 (13)0.0028 (13)
C30.0698 (19)0.0546 (16)0.0609 (18)0.0253 (14)0.0404 (16)0.0045 (13)
C40.0567 (16)0.0319 (13)0.0716 (19)0.0143 (12)0.0271 (15)0.0093 (12)
C50.0481 (14)0.0354 (12)0.0281 (12)−0.0207 (10)0.0138 (11)−0.0098 (9)
C60.0407 (15)0.0767 (19)0.0458 (16)−0.0236 (13)0.0158 (13)−0.0202 (14)
C70.102 (3)0.0393 (14)0.0476 (16)−0.0335 (15)0.0280 (17)−0.0087 (12)
C80.0609 (17)0.0530 (15)0.0287 (13)−0.0182 (13)0.0166 (12)−0.0106 (11)
C90.0498 (14)0.0361 (12)0.0263 (11)−0.0087 (10)0.0219 (11)−0.0010 (9)
C100.0582 (16)0.0429 (13)0.0277 (12)−0.0087 (11)0.0192 (12)0.0001 (10)
C110.0584 (16)0.0609 (16)0.0430 (15)−0.0023 (13)0.0353 (14)−0.0032 (12)
C120.088 (2)0.0476 (15)0.0413 (15)−0.0232 (14)0.0375 (16)0.0003 (11)
C130.0240 (10)0.0236 (9)0.0233 (10)0.0010 (8)0.0028 (9)0.0049 (8)
C140.0322 (12)0.0464 (13)0.0349 (12)−0.0047 (10)0.0091 (10)0.0122 (10)
C150.0246 (10)0.0315 (10)0.0256 (11)0.0011 (8)0.0029 (9)0.0031 (8)
C160.0350 (12)0.0267 (10)0.0339 (12)0.0061 (9)0.0001 (10)−0.0008 (9)
C170.0325 (12)0.0525 (14)0.0268 (11)−0.0091 (10)0.0161 (10)−0.0055 (9)
C180.0343 (13)0.0610 (15)0.0361 (13)−0.0151 (11)0.0172 (11)−0.0092 (11)
C190.0545 (16)0.0713 (18)0.0346 (14)−0.0109 (14)0.0208 (13)0.0078 (12)
C200.0425 (14)0.0752 (18)0.0424 (14)−0.0064 (13)0.0248 (12)−0.0205 (13)
C210.0221 (10)0.0290 (10)0.0215 (10)−0.0041 (8)0.0031 (8)−0.0027 (8)
C220.0401 (14)0.0395 (13)0.0439 (14)−0.0024 (10)0.0088 (12)−0.0116 (10)
C230.0394 (14)0.0657 (17)0.0432 (15)−0.0195 (12)0.0148 (12)−0.0081 (12)
C240.0393 (14)0.0429 (14)0.0390 (14)−0.0043 (11)−0.0065 (12)0.0052 (11)
C250.0290 (11)0.0437 (12)0.0281 (11)−0.0096 (9)0.0106 (10)−0.0062 (9)
C260.0410 (13)0.0439 (13)0.0290 (12)−0.0072 (10)0.0158 (11)−0.0053 (9)
C270.0292 (11)0.0351 (11)0.0300 (11)−0.0025 (9)0.0120 (10)0.0053 (9)
C280.0367 (14)0.0796 (19)0.0365 (14)−0.0215 (13)0.0079 (12)0.0050 (13)
C290.0608 (18)0.0635 (18)0.0585 (18)−0.0278 (15)0.0209 (15)−0.0179 (14)
O70.0265 (8)0.0795 (12)0.0296 (9)−0.0119 (8)0.0137 (7)−0.0124 (8)
C300.0286 (11)0.0398 (12)0.0293 (11)0.0002 (9)0.0121 (10)0.0012 (9)
C310.0415 (14)0.0523 (14)0.0394 (13)−0.0064 (11)0.0233 (12)−0.0001 (11)
C320.0376 (13)0.0612 (16)0.0373 (13)−0.0107 (11)0.0158 (11)−0.0080 (11)
Geometric parameters (Å, °) top
Zn1—N12.0134 (17)C12—H12C0.98
Zn1—S22.2749 (6)C13—C161.518 (3)
Zn1—S12.2878 (5)C13—C141.519 (3)
Zn1—O42.4039 (12)C13—C151.522 (3)
Zn1—O12.5436 (14)C14—H14A0.98
S1—Si12.0897 (7)C14—H14B0.98
S2—Si22.0818 (7)C14—H14C0.98
Si1—O11.6442 (15)C15—H15A0.98
Si1—O21.6214 (14)C15—H15B0.98
Si1—O31.6253 (14)C15—H15C0.98
Si2—O41.6563 (13)C16—H16A0.98
Si2—O51.6261 (14)C16—H16B0.98
Si2—O61.6317 (14)C16—H16C0.98
O1—C11.462 (2)C17—C191.510 (4)
O2—C51.448 (3)C17—C181.527 (3)
O3—C91.449 (2)C17—C201.531 (3)
O4—C131.465 (2)C18—H18A0.98
O5—C171.448 (2)C18—H18B0.98
O6—C211.443 (2)C18—H18C0.98
N1—C271.327 (3)C19—H19A0.98
N1—C251.379 (3)C19—H19B0.98
N2—C271.350 (3)C19—H19C0.98
N2—C261.370 (3)C20—H20A0.98
N2—H20.88C20—H20B0.98
C1—C21.512 (4)C20—H20C0.98
C1—C31.518 (3)C21—C241.504 (3)
C1—C41.524 (3)C21—C231.513 (3)
C2—H2A0.98C21—C221.525 (3)
C2—H2B0.98C22—H22A0.98
C2—H2C0.98C22—H22B0.98
C3—H3A0.98C22—H22C0.98
C3—H3B0.98C23—H23A0.98
C3—H3C0.98C23—H23B0.98
C4—H4A0.98C23—H23C0.98
C4—H4B0.98C24—H24A0.98
C4—H4C0.98C24—H24B0.98
C5—C71.514 (3)C24—H24C0.98
C5—C61.515 (4)C25—C261.346 (3)
C5—C81.518 (3)C25—H250.95
C6—H6A0.98C26—H260.95
C6—H6B0.98C27—C281.490 (3)
C6—H6C0.98C28—C291.464 (4)
C7—H7A0.98C28—H28A0.99
C7—H7B0.98C28—H28B0.99
C7—H7C0.98C29—H29A0.98
C8—H8A0.98C29—H29B0.98
C8—H8B0.98C29—H29C0.98
C8—H8C0.98O7—C301.430 (3)
C9—C101.516 (3)O7—H70.8401
C9—C111.521 (4)C30—C311.501 (3)
C9—C121.523 (3)C30—C321.506 (3)
C10—H10A0.98C30—H301
C10—H10B0.98C31—H31A0.98
C10—H10C0.98C31—H31B0.98
C11—H11A0.98C31—H31C0.98
C11—H11B0.98C32—H32A0.98
C11—H11C0.98C32—H32B0.98
C12—H12A0.98C32—H32C0.98
C12—H12B0.98
N1—Zn1—S2120.90 (5)O4—C13—C16110.46 (16)
N1—Zn1—S1110.16 (5)O4—C13—C14107.82 (16)
S2—Zn1—S1128.70 (2)C16—C13—C14111.48 (18)
N1—Zn1—O4102.24 (6)O4—C13—C15105.46 (15)
S2—Zn1—O477.25 (3)C16—C13—C15110.65 (17)
S1—Zn1—O497.47 (3)C14—C13—C15110.76 (17)
N1—Zn1—O190.62 (6)C13—C14—H14A109.5
S2—Zn1—O199.72 (3)C13—C14—H14B109.5
S1—Zn1—O173.98 (3)H14A—C14—H14B109.5
O4—Zn1—O1166.52 (4)C13—C14—H14C109.5
Si1—S1—Zn190.53 (2)H14A—C14—H14C109.5
Si2—S2—Zn186.98 (2)H14B—C14—H14C109.5
O2—Si1—O3106.26 (7)C13—C15—H15A109.5
O2—Si1—O1106.83 (8)C13—C15—H15B109.5
O3—Si1—O1112.64 (8)H15A—C15—H15B109.5
O2—Si1—S1115.04 (6)C13—C15—H15C109.5
O3—Si1—S1114.04 (6)H15A—C15—H15C109.5
O1—Si1—S1101.94 (6)H15B—C15—H15C109.5
O5—Si2—O6105.21 (7)C13—C16—H16A109.5
O5—Si2—O4113.16 (7)C13—C16—H16B109.5
O6—Si2—O4104.62 (7)H16A—C16—H16B109.5
O5—Si2—S2114.99 (6)C13—C16—H16C109.5
O6—Si2—S2116.35 (6)H16A—C16—H16C109.5
O4—Si2—S2102.24 (5)H16B—C16—H16C109.5
C1—O1—Si1131.29 (14)O5—C17—C19109.18 (19)
C1—O1—Zn1134.39 (12)O5—C17—C18110.31 (17)
Si1—O1—Zn193.54 (6)C19—C17—C18111.1 (2)
C5—O2—Si1133.00 (13)O5—C17—C20104.71 (18)
C9—O3—Si1132.76 (13)C19—C17—C20111.1 (2)
C13—O4—Si2129.96 (12)C18—C17—C20110.2 (2)
C13—O4—Zn1134.86 (11)C17—C18—H18A109.5
Si2—O4—Zn193.52 (6)C17—C18—H18B109.5
C17—O5—Si2134.23 (13)H18A—C18—H18B109.5
C21—O6—Si2131.84 (12)C17—C18—H18C109.5
C27—N1—C25106.70 (17)H18A—C18—H18C109.5
C27—N1—Zn1130.56 (15)H18B—C18—H18C109.5
C25—N1—Zn1122.31 (14)C17—C19—H19A109.5
C27—N2—C26108.30 (18)C17—C19—H19B109.5
C27—N2—H2125.8H19A—C19—H19B109.5
C26—N2—H2125.9C17—C19—H19C109.5
O1—C1—C2105.24 (18)H19A—C19—H19C109.5
O1—C1—C3108.31 (18)H19B—C19—H19C109.5
C2—C1—C3111.0 (2)C17—C20—H20A109.5
O1—C1—C4110.58 (19)C17—C20—H20B109.5
C2—C1—C4110.9 (2)H20A—C20—H20B109.5
C3—C1—C4110.6 (2)C17—C20—H20C109.5
C1—C2—H2A109.5H20A—C20—H20C109.5
C1—C2—H2B109.5H20B—C20—H20C109.5
H2A—C2—H2B109.5O6—C21—C24110.46 (17)
C1—C2—H2C109.5O6—C21—C23105.98 (16)
H2A—C2—H2C109.5C24—C21—C23111.1 (2)
H2B—C2—H2C109.5O6—C21—C22108.30 (16)
C1—C3—H3A109.5C24—C21—C22111.5 (2)
C1—C3—H3B109.5C23—C21—C22109.33 (19)
H3A—C3—H3B109.5C21—C22—H22A109.5
C1—C3—H3C109.5C21—C22—H22B109.5
H3A—C3—H3C109.5H22A—C22—H22B109.5
H3B—C3—H3C109.5C21—C22—H22C109.5
C1—C4—H4A109.5H22A—C22—H22C109.5
C1—C4—H4B109.5H22B—C22—H22C109.5
H4A—C4—H4B109.5C21—C23—H23A109.5
C1—C4—H4C109.5C21—C23—H23B109.5
H4A—C4—H4C109.5H23A—C23—H23B109.5
H4B—C4—H4C109.5C21—C23—H23C109.5
O2—C5—C7108.5 (2)H23A—C23—H23C109.5
O2—C5—C6110.94 (18)H23B—C23—H23C109.5
C7—C5—C6111.0 (2)C21—C24—H24A109.5
O2—C5—C8105.17 (18)C21—C24—H24B109.5
C7—C5—C8110.7 (2)H24A—C24—H24B109.5
C6—C5—C8110.4 (2)C21—C24—H24C109.5
C5—C6—H6A109.5H24A—C24—H24C109.5
C5—C6—H6B109.5H24B—C24—H24C109.5
H6A—C6—H6B109.5C26—C25—N1109.25 (19)
C5—C6—H6C109.5C26—C25—H25125.4
H6A—C6—H6C109.5N1—C25—H25125.4
H6B—C6—H6C109.5C25—C26—N2106.31 (19)
C5—C7—H7A109.5C25—C26—H26126.8
C5—C7—H7B109.5N2—C26—H26126.8
H7A—C7—H7B109.5N1—C27—N2109.44 (19)
C5—C7—H7C109.5N1—C27—C28127.0 (2)
H7A—C7—H7C109.5N2—C27—C28123.6 (2)
H7B—C7—H7C109.5C29—C28—C27114.8 (2)
C5—C8—H8A109.5C29—C28—H28A108.6
C5—C8—H8B109.5C27—C28—H28A108.6
H8A—C8—H8B109.5C29—C28—H28B108.6
C5—C8—H8C109.5C27—C28—H28B108.6
H8A—C8—H8C109.5H28A—C28—H28B107.5
H8B—C8—H8C109.5C28—C29—H29A109.5
O3—C9—C10110.77 (18)C28—C29—H29B109.5
O3—C9—C11108.88 (18)H29A—C29—H29B109.5
C10—C9—C11111.0 (2)C28—C29—H29C109.5
O3—C9—C12104.69 (17)H29A—C29—H29C109.5
C10—C9—C12110.4 (2)H29B—C29—H29C109.5
C11—C9—C12110.9 (2)C30—O7—H7109.4
C9—C10—H10A109.5O7—C30—C31110.75 (19)
C9—C10—H10B109.5O7—C30—C32105.92 (18)
H10A—C10—H10B109.5C31—C30—C32112.8 (2)
C9—C10—H10C109.5O7—C30—H30109.1
H10A—C10—H10C109.5C31—C30—H30109.1
H10B—C10—H10C109.5C32—C30—H30109.1
C9—C11—H11A109.5C30—C31—H31A109.5
C9—C11—H11B109.5C30—C31—H31B109.5
H11A—C11—H11B109.5H31A—C31—H31B109.5
C9—C11—H11C109.5C30—C31—H31C109.5
H11A—C11—H11C109.5H31A—C31—H31C109.5
H11B—C11—H11C109.5H31B—C31—H31C109.5
C9—C12—H12A109.5C30—C32—H32A109.5
C9—C12—H12B109.5C30—C32—H32B109.5
H12A—C12—H12B109.5H32A—C32—H32B109.5
C9—C12—H12C109.5C30—C32—H32C109.5
H12A—C12—H12C109.5H32A—C32—H32C109.5
H12B—C12—H12C109.5H32B—C32—H32C109.5
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O7i0.881.892.774 (2)179
O7—H7···S1ii0.842.373.1976 (16)168
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x+1, −y+3/2, z+1/2.
Table 1
Selected geometric parameters (Å, °) top
Zn1—N12.0134 (17)Zn1—O12.5436 (14)
Zn1—S22.2749 (6)S1—Si12.0897 (7)
Zn1—S12.2878 (5)S2—Si22.0818 (7)
Zn1—O42.4039 (12)
N1—Zn1—S2120.90 (5)S2—Zn1—S1128.70 (2)
N1—Zn1—S1110.16 (5)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2···O7i0.881.892.774 (2)179
O7—H7···S1ii0.842.373.1976 (16)168
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x+1, −y+3/2, z+1/2.
Acknowledgements top

This work was carried out with financial support from the Polish Ministry of Science and Higher Education (grant No. 3 T09A 12028).

references
References top

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Oxford Diffraction (2006). CrysAlis CCD and CrysAlis RED. Versions 1.171.29.9. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.

Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.