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Acta Cryst. (2008). E64, m680    [ doi:10.1107/S1600536808010003 ]

[mu]-1,2-Di-4-pyridylethane-[kappa]2N:N'-bis[bis(N,N-diisopropyldithiocarbamato-[kappa]2S,S')zinc(II)]

V. Avila and E. R. T. Tiekink

Abstract top

In the dinuclear title compound, [Zn{S2CN(n-Pr)2}2{(NC5H4)CH2CH2(C5H4N)}] or [Zn2(C7H14NS2)4(C12H12N2)], each Zn atom adopts a distorted trigonal-bipyramidal ZnNS4 geometry. The crystal structure involves intermolecular C-H...S hydrogen bonds.

Comment top

Interest in the title compound (I), Fig. 1 & Table 1, rests with an on-going investigation of the aggregation patterns of zinc and cadmium 1,1-dithiolates (Lai et al., 2004, Chen et al., 2006 & Benson et al., 2007). The dimeric structure features two highly distorted trigonal bipyramidal NS4 coordination geometries with values of τ = 0.64 and 0.72 for Zn1 and Zn2, respectively (Addison et al., 1984). The dithiocarbamate ligands coordinate forming almost symmetrical Zn—S bond distances in accord with expectation (Tiekink, 2006). The primary interactions between molecules are of the type C—H···S, Table 2. Each dimer participates in four such interactions. Dimers are arranged in an herringbone fashion in the bc-plane, Fig. 2. The resultant layers are basically flat with the n-propyl groups projecting above and below to inter-digitate with adjacent layers, Fig. 3.

Related literature top

For related structures, see: Lai et al. (2004); Chen et al. (2006); Benson et al. (2007). For related literature, see: Tiekink (2006). For structure analysis, see: Addison et al. (1984).

Experimental top

The title compound was prepared by refluxing the parent zinc dithiocarbamate with 1,2-bis(4-pyridyl)ethane using a literature procedure (Lai et al., 2004). Colourless crystals of (I) were isolated by the slow evaporation of an ethanol/methanol (1/1) solution; m.p. 451 - 453 K.

Refinement top

The H atoms were geometrically placed (C—H = 0.95–0.99 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: PATTY in DIRDIF92 (Beurskens et al., 1992); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms). For clarity only the first atom of consecutively numbered iso-propyl groups and the N and two C atoms of the bispyridylethane ligand have been numbered.
[Figure 2] Fig. 2. View of a layer in (I) highlighting the herringbone arrangement. Colour code: Zn (orange), S (yellow), O (red), N (blue), C (grey) & H (green).
[Figure 3] Fig. 3. Side-on view of a layer in (I). Colour code as for Fig. 2.
µ-1,2-Di-4-pyridylethane-κ2N:N'- bis[bis(N,N-diisopropyldithiocarbamato- κ2S,S')zinc(II)] top
Crystal data top
[Zn2(C7H14NS2)4(C12H12N2)]F(000) = 2152
Mr = 1020.22Dx = 1.338 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 17064 reflections
a = 18.645 (5) Åθ = 2.1–30.5°
b = 15.464 (5) ŵ = 1.31 mm−1
c = 17.567 (4) ÅT = 98 K
β = 90.756 (11)°Block, colourless
V = 5064 (3) Å30.15 × 0.11 × 0.11 mm
Z = 4
Data collection top
Rigaku AFC12K/SATURN724
diffractometer		10501 independent reflections
Radiation source: fine-focus sealed tube9945 reflections with I > 2σ(I)
graphiteRint = 0.040
ω scansθmax = 26.5°, θmin = 1.8°
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		h = −20→23
Tmin = 0.757, Tmax = 1k = −19→19
52873 measured reflectionsl = −22→22
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.0347P)2 + 4.0808P]
where P = (Fo2 + 2Fc2)/3
10501 reflections(Δ/σ)max = 0.001
505 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.41 e Å−3
Crystal data top
[Zn2(C7H14NS2)4(C12H12N2)]V = 5064 (3) Å3
Mr = 1020.22Z = 4
Monoclinic, P21/cMo Kα radiation
a = 18.645 (5) ŵ = 1.31 mm−1
b = 15.464 (5) ÅT = 98 K
c = 17.567 (4) Å0.15 × 0.11 × 0.11 mm
β = 90.756 (11)°
Data collection top
Rigaku AFC12K/SATURN724
diffractometer		9945 reflections with I > 2σ(I)
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)		Rint = 0.040
Tmin = 0.757, Tmax = 1θmax = 26.5°
52873 measured reflectionsStandard reflections: 0
10501 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.089Δρmax = 0.47 e Å−3
S = 1.14Δρmin = −0.41 e Å−3
10501 reflectionsAbsolute structure: ?
505 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
Zn10.276298 (14)0.197149 (17)0.666864 (15)0.01860 (7)
Zn20.233401 (14)0.792692 (17)0.113503 (15)0.01919 (7)
S10.17394 (3)0.17012 (4)0.74108 (3)0.02267 (13)
S20.19934 (3)0.08862 (4)0.59234 (3)0.02227 (13)
S30.38566 (3)0.12770 (4)0.69274 (3)0.02016 (12)
S40.33916 (3)0.28608 (4)0.77400 (3)0.01942 (12)
S50.14013 (3)0.88860 (4)0.08654 (3)0.02158 (13)
S60.25034 (3)0.92616 (4)0.20351 (3)0.02157 (13)
S70.34319 (3)0.79323 (4)0.05134 (3)0.02127 (13)
S80.22111 (3)0.68586 (4)0.00107 (3)0.02082 (13)
N10.07846 (11)0.06823 (13)0.67052 (11)0.0228 (4)
N20.46332 (10)0.20599 (12)0.80062 (11)0.0192 (4)
N30.28479 (10)0.29088 (12)0.58188 (11)0.0182 (4)
N40.23109 (10)0.70372 (12)0.20140 (11)0.0185 (4)
N50.14157 (10)1.03193 (12)0.17162 (11)0.0203 (4)
N60.35081 (10)0.68252 (12)−0.06437 (11)0.0202 (4)
C10.14307 (12)0.10457 (14)0.66783 (13)0.0197 (5)
C20.02924 (14)0.07935 (17)0.73493 (15)0.0290 (6)
H2A0.05700.10020.77970.035*
H2B0.00860.02240.74810.035*
C3−0.03145 (15)0.14235 (18)0.71824 (18)0.0370 (7)
H3A−0.05790.12270.67220.044*
H3B−0.06520.14140.76120.044*
C4−0.00637 (16)0.23467 (19)0.7060 (2)0.0501 (9)
H4A−0.04780.27150.69400.075*
H4B0.02730.23630.66360.075*
H4C0.01760.25580.75230.075*
C50.05257 (13)0.00974 (15)0.60992 (14)0.0247 (5)
H5A0.07190.02920.56060.030*
H5B−0.00040.01320.60660.030*
C60.07454 (14)−0.08379 (16)0.62354 (16)0.0308 (6)
H6A0.0580−0.10220.67440.037*
H6B0.1275−0.08810.62320.037*
C70.04309 (15)−0.14398 (19)0.56328 (19)0.0418 (7)
H7A0.0579−0.20350.57420.063*
H7B0.0605−0.12700.51300.063*
H7C−0.0094−0.14020.56370.063*
C80.40247 (12)0.20721 (14)0.76077 (13)0.0186 (5)
C90.47860 (13)0.27132 (15)0.85971 (13)0.0209 (5)
H9A0.51030.24550.89920.025*
H9B0.43310.28780.88430.025*
C100.51413 (15)0.35234 (16)0.82855 (14)0.0281 (6)
H10A0.55670.33570.79880.034*
H10B0.48010.38250.79390.034*
C110.53706 (15)0.41336 (16)0.89228 (15)0.0302 (6)
H11A0.55930.46500.87040.045*
H11B0.57170.38410.92590.045*
H11C0.49500.43040.92150.045*
C120.52046 (12)0.14240 (15)0.78581 (13)0.0213 (5)
H12A0.56680.16630.80430.026*
H12B0.52410.13380.73010.026*
C130.50823 (13)0.05467 (15)0.82364 (13)0.0237 (5)
H13A0.46640.02640.79880.028*
H13B0.55070.01770.81490.028*
C140.49519 (14)0.05979 (16)0.90901 (14)0.0270 (5)
H14A0.48680.00160.92900.041*
H14B0.45310.09600.91840.041*
H14C0.53730.08510.93450.041*
C150.30356 (12)0.37329 (15)0.59697 (13)0.0204 (5)
H150.31270.38950.64840.025*
C160.31004 (12)0.43544 (15)0.54064 (13)0.0207 (5)
H160.32260.49310.55390.025*
C170.29832 (12)0.41359 (15)0.46541 (13)0.0215 (5)
C180.27989 (14)0.32803 (16)0.44944 (14)0.0246 (5)
H180.27170.31010.39830.029*
C190.27354 (13)0.26952 (15)0.50843 (13)0.0231 (5)
H190.26060.21160.49660.028*
C200.30233 (13)0.47978 (16)0.40236 (14)0.0251 (5)
H20A0.32270.45260.35640.030*
H20B0.33460.52750.41830.030*
C210.22824 (13)0.51607 (15)0.38322 (13)0.0232 (5)
H21A0.19610.46800.36790.028*
H21B0.20820.54320.42930.028*
C220.22989 (12)0.58203 (15)0.32004 (13)0.0205 (5)
C230.20409 (13)0.66545 (15)0.33017 (13)0.0225 (5)
H230.18540.68250.37800.027*
C240.20565 (13)0.72358 (15)0.27055 (13)0.0224 (5)
H240.18790.78040.27880.027*
C250.25688 (13)0.62323 (15)0.19170 (13)0.0227 (5)
H250.27560.60810.14350.027*
C260.25737 (13)0.56184 (15)0.24854 (13)0.0224 (5)
H260.27630.50590.23920.027*
C270.17453 (12)0.95762 (14)0.15605 (13)0.0193 (5)
C280.16746 (13)1.09056 (15)0.23204 (13)0.0211 (5)
H28A0.15531.15080.21780.025*
H28B0.22041.08630.23600.025*
C290.13528 (13)1.07032 (16)0.30966 (14)0.0251 (5)
H29A0.08241.07570.30640.030*
H29B0.14701.01000.32410.030*
C300.16433 (14)1.13174 (17)0.37031 (14)0.0285 (6)
H30A0.14341.11730.41960.043*
H30B0.15171.19130.35670.043*
H30C0.21661.12620.37380.043*
C310.08007 (13)1.06331 (15)0.12656 (14)0.0242 (5)
H31A0.04851.09810.15950.029*
H31B0.05211.01330.10730.029*
C320.10403 (14)1.11850 (17)0.05937 (15)0.0304 (6)
H32A0.12761.17160.07880.036*
H32B0.13971.08590.02950.036*
C330.04147 (17)1.1435 (2)0.00780 (19)0.0479 (8)
H33A0.05891.1792−0.03420.072*
H33B0.00631.17630.03700.072*
H33C0.01881.0911−0.01280.072*
C340.30891 (12)0.71559 (15)−0.01075 (13)0.0191 (5)
C350.32439 (13)0.62269 (16)−0.12376 (13)0.0235 (5)
H35A0.33710.6462−0.17420.028*
H35B0.27140.6199−0.12140.028*
C360.35456 (14)0.53096 (16)−0.11662 (15)0.0283 (5)
H36A0.33790.4965−0.16090.034*
H36B0.40760.5337−0.11830.034*
C370.33268 (16)0.48523 (17)−0.04401 (15)0.0340 (6)
H37A0.35370.4271−0.04280.051*
H37B0.28030.4808−0.04260.051*
H37C0.35000.51830.00020.051*
C380.42600 (13)0.71040 (15)−0.07166 (14)0.0209 (5)
H38A0.45370.6631−0.09520.025*
H38B0.44640.7206−0.02010.025*
C390.43520 (14)0.79207 (16)−0.11890 (15)0.0269 (5)
H39A0.42230.7801−0.17270.032*
H39B0.40290.8379−0.10000.032*
C400.51250 (14)0.82263 (17)−0.11344 (16)0.0310 (6)
H40A0.51830.8750−0.14420.046*
H40B0.54430.7772−0.13240.046*
H40C0.52480.8354−0.06020.046*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01984 (14)0.01810 (14)0.01781 (14)−0.00116 (10)−0.00162 (10)0.00323 (10)
Zn20.02074 (14)0.01852 (14)0.01832 (14)0.00293 (10)0.00090 (11)0.00377 (10)
S10.0264 (3)0.0201 (3)0.0216 (3)−0.0050 (2)0.0031 (2)−0.0030 (2)
S20.0238 (3)0.0234 (3)0.0196 (3)−0.0045 (2)0.0012 (2)−0.0015 (2)
S30.0239 (3)0.0168 (3)0.0196 (3)0.0009 (2)−0.0034 (2)−0.0014 (2)
S40.0219 (3)0.0182 (3)0.0180 (3)0.0021 (2)−0.0028 (2)−0.0004 (2)
S50.0230 (3)0.0191 (3)0.0226 (3)0.0028 (2)−0.0059 (2)−0.0028 (2)
S60.0253 (3)0.0186 (3)0.0206 (3)0.0018 (2)−0.0063 (2)0.0012 (2)
S70.0196 (3)0.0236 (3)0.0207 (3)−0.0013 (2)0.0001 (2)−0.0038 (2)
S80.0199 (3)0.0237 (3)0.0188 (3)−0.0016 (2)−0.0010 (2)−0.0006 (2)
N10.0235 (10)0.0208 (10)0.0240 (10)−0.0029 (8)0.0007 (8)−0.0021 (8)
N20.0209 (10)0.0181 (10)0.0186 (10)0.0005 (7)−0.0034 (8)−0.0003 (8)
N30.0215 (10)0.0157 (9)0.0173 (10)0.0007 (7)−0.0005 (8)0.0018 (7)
N40.0217 (10)0.0155 (9)0.0183 (10)0.0011 (7)−0.0003 (8)0.0000 (7)
N50.0232 (10)0.0170 (9)0.0207 (10)−0.0009 (8)−0.0009 (8)−0.0008 (8)
N60.0211 (10)0.0218 (10)0.0177 (10)0.0006 (8)−0.0010 (8)−0.0017 (8)
C10.0232 (11)0.0142 (11)0.0218 (11)−0.0016 (9)−0.0009 (9)0.0027 (9)
C20.0299 (13)0.0257 (13)0.0317 (14)−0.0072 (11)0.0108 (11)−0.0016 (11)
C30.0294 (14)0.0285 (14)0.0534 (18)−0.0032 (11)0.0134 (13)−0.0024 (13)
C40.0307 (15)0.0302 (16)0.090 (3)0.0008 (12)0.0138 (16)0.0025 (16)
C50.0230 (12)0.0219 (12)0.0291 (13)−0.0040 (10)−0.0019 (10)−0.0020 (10)
C60.0277 (13)0.0235 (13)0.0410 (15)−0.0013 (10)−0.0029 (12)−0.0059 (11)
C70.0319 (15)0.0314 (15)0.062 (2)−0.0014 (12)−0.0045 (14)−0.0186 (14)
C80.0231 (12)0.0171 (11)0.0155 (11)−0.0044 (9)−0.0003 (9)0.0040 (9)
C90.0238 (12)0.0196 (11)0.0191 (11)−0.0026 (9)−0.0054 (9)−0.0006 (9)
C100.0375 (14)0.0230 (13)0.0237 (13)−0.0076 (11)−0.0072 (11)0.0033 (10)
C110.0390 (15)0.0215 (13)0.0300 (14)−0.0059 (11)−0.0076 (11)0.0035 (11)
C120.0201 (11)0.0210 (12)0.0229 (12)0.0026 (9)−0.0007 (9)0.0017 (9)
C130.0278 (12)0.0219 (12)0.0215 (12)0.0037 (10)−0.0017 (10)0.0018 (10)
C140.0329 (14)0.0243 (13)0.0238 (13)−0.0027 (10)−0.0020 (10)0.0027 (10)
C150.0238 (12)0.0207 (12)0.0168 (11)0.0008 (9)−0.0003 (9)−0.0019 (9)
C160.0252 (12)0.0160 (11)0.0209 (11)−0.0022 (9)−0.0009 (9)0.0020 (9)
C170.0215 (11)0.0230 (12)0.0201 (11)0.0025 (9)0.0003 (9)0.0047 (9)
C180.0348 (14)0.0227 (12)0.0162 (11)0.0011 (10)0.0006 (10)0.0008 (10)
C190.0326 (13)0.0179 (11)0.0188 (11)0.0005 (10)−0.0015 (10)−0.0018 (9)
C200.0293 (13)0.0259 (13)0.0201 (12)−0.0016 (10)−0.0009 (10)0.0073 (10)
C210.0308 (13)0.0210 (12)0.0178 (11)0.0025 (10)0.0014 (10)0.0027 (9)
C220.0245 (12)0.0183 (11)0.0187 (11)−0.0005 (9)−0.0004 (9)0.0009 (9)
C230.0300 (13)0.0196 (12)0.0180 (11)0.0010 (10)0.0021 (10)−0.0008 (9)
C240.0275 (12)0.0173 (11)0.0224 (12)0.0034 (9)0.0024 (10)−0.0011 (9)
C250.0279 (12)0.0222 (12)0.0180 (11)0.0039 (10)−0.0003 (10)−0.0002 (9)
C260.0297 (13)0.0173 (11)0.0201 (12)0.0052 (9)−0.0003 (10)−0.0001 (9)
C270.0234 (11)0.0164 (11)0.0182 (11)−0.0028 (9)0.0012 (9)0.0026 (9)
C280.0236 (12)0.0180 (11)0.0218 (12)−0.0036 (9)0.0017 (9)−0.0030 (9)
C290.0266 (12)0.0241 (12)0.0247 (13)−0.0038 (10)0.0009 (10)−0.0021 (10)
C300.0329 (14)0.0316 (14)0.0209 (12)−0.0039 (11)−0.0009 (10)−0.0016 (11)
C310.0203 (11)0.0198 (12)0.0326 (13)0.0035 (9)−0.0046 (10)−0.0018 (10)
C320.0289 (13)0.0297 (14)0.0324 (14)0.0030 (11)−0.0068 (11)0.0060 (11)
C330.0469 (18)0.0470 (19)0.0491 (19)0.0063 (15)−0.0201 (15)0.0101 (15)
C340.0211 (11)0.0200 (11)0.0163 (11)0.0024 (9)−0.0018 (9)0.0041 (9)
C350.0274 (12)0.0273 (13)0.0157 (11)0.0022 (10)−0.0020 (9)−0.0038 (10)
C360.0313 (13)0.0240 (13)0.0295 (13)0.0010 (10)−0.0016 (11)−0.0045 (11)
C370.0438 (16)0.0254 (13)0.0326 (15)−0.0059 (12)−0.0059 (12)0.0007 (11)
C380.0213 (12)0.0215 (12)0.0200 (12)0.0003 (9)0.0011 (9)0.0001 (9)
C390.0314 (14)0.0252 (13)0.0243 (13)0.0017 (10)0.0077 (11)0.0031 (10)
C400.0348 (14)0.0249 (13)0.0336 (15)−0.0038 (11)0.0114 (12)−0.0045 (11)
Geometric parameters (Å, °) top
Zn1—S12.3627 (8)C13—H13A0.9900
Zn1—S22.5573 (8)C13—H13B0.9900
Zn1—S32.3437 (8)C14—H14A0.9800
Zn1—S42.5978 (8)C14—H14B0.9800
Zn1—N32.0882 (19)C14—H14C0.9800
Zn2—S52.3295 (8)C15—C161.386 (3)
Zn2—S62.6166 (9)C15—H150.9500
Zn2—S72.3327 (9)C16—C171.379 (3)
Zn2—S82.5829 (8)C16—H160.9500
Zn2—N42.0691 (19)C17—C181.394 (3)
S1—C11.731 (2)C17—C201.511 (3)
S2—C11.720 (2)C18—C191.382 (3)
S3—C81.740 (2)C18—H180.9500
S4—C81.715 (2)C19—H190.9500
S5—C271.738 (2)C20—C211.524 (3)
S6—C271.702 (2)C20—H20A0.9900
S7—C341.738 (2)C20—H20B0.9900
S8—C341.716 (2)C21—C221.508 (3)
N1—C11.331 (3)C21—H21A0.9900
N1—C51.473 (3)C21—H21B0.9900
N1—C21.476 (3)C22—C231.389 (3)
N2—C81.326 (3)C22—C261.398 (3)
N2—C91.474 (3)C23—C241.381 (3)
N2—C121.475 (3)C23—H230.9500
N3—C191.346 (3)C24—H240.9500
N3—C151.347 (3)C25—C261.378 (3)
N4—C241.345 (3)C25—H250.9500
N4—C251.346 (3)C26—H260.9500
N5—C271.333 (3)C28—C291.529 (3)
N5—C311.467 (3)C28—H28A0.9900
N5—C281.473 (3)C28—H28B0.9900
N6—C341.334 (3)C29—C301.522 (3)
N6—C381.474 (3)C29—H29A0.9900
N6—C351.474 (3)C29—H29B0.9900
C2—C31.519 (4)C30—H30A0.9800
C2—H2A0.9900C30—H30B0.9800
C2—H2B0.9900C30—H30C0.9800
C3—C41.519 (4)C31—C321.528 (4)
C3—H3A0.9900C31—H31A0.9900
C3—H3B0.9900C31—H31B0.9900
C4—H4A0.9800C32—C331.517 (4)
C4—H4B0.9800C32—H32A0.9900
C4—H4C0.9800C32—H32B0.9900
C5—C61.521 (3)C33—H33A0.9800
C5—H5A0.9900C33—H33B0.9800
C5—H5B0.9900C33—H33C0.9800
C6—C71.521 (4)C35—C361.530 (3)
C6—H6A0.9900C35—H35A0.9900
C6—H6B0.9900C35—H35B0.9900
C7—H7A0.9800C36—C371.519 (4)
C7—H7B0.9800C36—H36A0.9900
C7—H7C0.9800C36—H36B0.9900
C9—C101.522 (3)C37—H37A0.9800
C9—H9A0.9900C37—H37B0.9800
C9—H9B0.9900C37—H37C0.9800
C10—C111.521 (3)C38—C391.522 (3)
C10—H10A0.9900C38—H38A0.9900
C10—H10B0.9900C38—H38B0.9900
C11—H11A0.9800C39—C401.519 (4)
C11—H11B0.9800C39—H39A0.9900
C11—H11C0.9800C39—H39B0.9900
C12—C131.529 (3)C40—H40A0.9800
C12—H12A0.9900C40—H40B0.9800
C12—H12B0.9900C40—H40C0.9800
C13—C141.524 (3)
N3—Zn1—S3112.50 (6)H14A—C14—H14C109.5
N3—Zn1—S1125.92 (6)H14B—C14—H14C109.5
S3—Zn1—S1121.26 (3)N3—C15—C16122.7 (2)
N3—Zn1—S297.87 (6)N3—C15—H15118.6
S3—Zn1—S2106.22 (3)C16—C15—H15118.6
S1—Zn1—S273.42 (3)C17—C16—C15120.0 (2)
N3—Zn1—S496.47 (6)C17—C16—H16120.0
S3—Zn1—S473.68 (3)C15—C16—H16120.0
S1—Zn1—S493.09 (3)C16—C17—C18117.4 (2)
S2—Zn1—S4164.37 (2)C16—C17—C20121.9 (2)
N4—Zn2—S5123.52 (6)C18—C17—C20120.6 (2)
N4—Zn2—S7112.26 (6)C19—C18—C17119.6 (2)
S5—Zn2—S7124.05 (3)C19—C18—H18120.2
N4—Zn2—S898.21 (6)C17—C18—H18120.2
S5—Zn2—S8101.15 (3)N3—C19—C18123.0 (2)
S7—Zn2—S873.37 (2)N3—C19—H19118.5
N4—Zn2—S694.42 (6)C18—C19—H19118.5
S5—Zn2—S672.81 (3)C17—C20—C21111.0 (2)
S7—Zn2—S6100.40 (2)C17—C20—H20A109.4
S6—Zn2—S8167.27 (2)C21—C20—H20A109.4
C1—S1—Zn187.50 (8)C17—C20—H20B109.4
C1—S2—Zn181.66 (8)C21—C20—H20B109.4
C8—S3—Zn187.58 (8)H20A—C20—H20B108.0
C8—S4—Zn180.22 (8)C22—C21—C20112.6 (2)
C27—S5—Zn288.89 (8)C22—C21—H21A109.1
C27—S6—Zn280.60 (8)C20—C21—H21A109.1
C34—S7—Zn288.49 (8)C22—C21—H21B109.1
C34—S8—Zn281.14 (8)C20—C21—H21B109.1
C1—N1—C5121.4 (2)H21A—C21—H21B107.8
C1—N1—C2123.4 (2)C23—C22—C26117.0 (2)
C5—N1—C2115.10 (19)C23—C22—C21121.6 (2)
C8—N2—C9121.23 (19)C26—C22—C21121.4 (2)
C8—N2—C12122.10 (19)C24—C23—C22119.8 (2)
C9—N2—C12116.61 (18)C24—C23—H23120.1
C19—N3—C15117.24 (19)C22—C23—H23120.1
C19—N3—Zn1120.18 (15)N4—C24—C23123.2 (2)
C15—N3—Zn1122.54 (15)N4—C24—H24118.4
C24—N4—C25117.1 (2)C23—C24—H24118.4
C24—N4—Zn2122.21 (15)N4—C25—C26123.0 (2)
C25—N4—Zn2120.62 (15)N4—C25—H25118.5
C27—N5—C31122.23 (19)C26—C25—H25118.5
C27—N5—C28122.1 (2)C25—C26—C22119.9 (2)
C31—N5—C28115.58 (19)C25—C26—H26120.1
C34—N6—C38121.05 (19)C22—C26—H26120.1
C34—N6—C35123.2 (2)N5—C27—S6121.86 (17)
C38—N6—C35115.55 (19)N5—C27—S5120.44 (18)
N1—C1—S2121.91 (18)S6—C27—S5117.70 (13)
N1—C1—S1120.88 (18)N5—C28—C29112.82 (19)
S2—C1—S1117.21 (13)N5—C28—H28A109.0
N1—C2—C3113.3 (2)C29—C28—H28A109.0
N1—C2—H2A108.9N5—C28—H28B109.0
C3—C2—H2A108.9C29—C28—H28B109.0
N1—C2—H2B108.9H28A—C28—H28B107.8
C3—C2—H2B108.9C30—C29—C28110.9 (2)
H2A—C2—H2B107.7C30—C29—H29A109.5
C4—C3—C2113.6 (2)C28—C29—H29A109.5
C4—C3—H3A108.8C30—C29—H29B109.5
C2—C3—H3A108.8C28—C29—H29B109.5
C4—C3—H3B108.8H29A—C29—H29B108.1
C2—C3—H3B108.8C29—C30—H30A109.5
H3A—C3—H3B107.7C29—C30—H30B109.5
C3—C4—H4A109.5H30A—C30—H30B109.5
C3—C4—H4B109.5C29—C30—H30C109.5
H4A—C4—H4B109.5H30A—C30—H30C109.5
C3—C4—H4C109.5H30B—C30—H30C109.5
H4A—C4—H4C109.5N5—C31—C32111.5 (2)
H4B—C4—H4C109.5N5—C31—H31A109.3
N1—C5—C6112.6 (2)C32—C31—H31A109.3
N1—C5—H5A109.1N5—C31—H31B109.3
C6—C5—H5A109.1C32—C31—H31B109.3
N1—C5—H5B109.1H31A—C31—H31B108.0
C6—C5—H5B109.1C33—C32—C31111.9 (2)
H5A—C5—H5B107.8C33—C32—H32A109.2
C5—C6—C7111.8 (2)C31—C32—H32A109.2
C5—C6—H6A109.3C33—C32—H32B109.2
C7—C6—H6A109.3C31—C32—H32B109.2
C5—C6—H6B109.3H32A—C32—H32B107.9
C7—C6—H6B109.3C32—C33—H33A109.5
H6A—C6—H6B107.9C32—C33—H33B109.5
C6—C7—H7A109.5H33A—C33—H33B109.5
C6—C7—H7B109.5C32—C33—H33C109.5
H7A—C7—H7B109.5H33A—C33—H33C109.5
C6—C7—H7C109.5H33B—C33—H33C109.5
H7A—C7—H7C109.5N6—C34—S8123.47 (18)
H7B—C7—H7C109.5N6—C34—S7119.62 (18)
N2—C8—S4121.63 (17)S8—C34—S7116.92 (13)
N2—C8—S3119.85 (18)N6—C35—C36113.9 (2)
S4—C8—S3118.52 (13)N6—C35—H35A108.8
N2—C9—C10113.1 (2)C36—C35—H35A108.8
N2—C9—H9A109.0N6—C35—H35B108.8
C10—C9—H9A109.0C36—C35—H35B108.8
N2—C9—H9B109.0H35A—C35—H35B107.7
C10—C9—H9B109.0C37—C36—C35113.4 (2)
H9A—C9—H9B107.8C37—C36—H36A108.9
C11—C10—C9111.4 (2)C35—C36—H36A108.9
C11—C10—H10A109.3C37—C36—H36B108.9
C9—C10—H10A109.3C35—C36—H36B108.9
C11—C10—H10B109.3H36A—C36—H36B107.7
C9—C10—H10B109.3C36—C37—H37A109.5
H10A—C10—H10B108.0C36—C37—H37B109.5
C10—C11—H11A109.5H37A—C37—H37B109.5
C10—C11—H11B109.5C36—C37—H37C109.5
H11A—C11—H11B109.5H37A—C37—H37C109.5
C10—C11—H11C109.5H37B—C37—H37C109.5
H11A—C11—H11C109.5N6—C38—C39113.84 (19)
H11B—C11—H11C109.5N6—C38—H38A108.8
N2—C12—C13113.74 (19)C39—C38—H38A108.8
N2—C12—H12A108.8N6—C38—H38B108.8
C13—C12—H12A108.8C39—C38—H38B108.8
N2—C12—H12B108.8H38A—C38—H38B107.7
C13—C12—H12B108.8C40—C39—C38109.7 (2)
H12A—C12—H12B107.7C40—C39—H39A109.7
C14—C13—C12114.1 (2)C38—C39—H39A109.7
C14—C13—H13A108.7C40—C39—H39B109.7
C12—C13—H13A108.7C38—C39—H39B109.7
C14—C13—H13B108.7H39A—C39—H39B108.2
C12—C13—H13B108.7C39—C40—H40A109.5
H13A—C13—H13B107.6C39—C40—H40B109.5
C13—C14—H14A109.5H40A—C40—H40B109.5
C13—C14—H14B109.5C39—C40—H40C109.5
H14A—C14—H14B109.5H40A—C40—H40C109.5
C13—C14—H14C109.5H40B—C40—H40C109.5
N3—Zn1—S1—C184.91 (10)C12—N2—C8—S34.3 (3)
S3—Zn1—S1—C1−102.05 (8)Zn1—S4—C8—N2179.3 (2)
S2—Zn1—S1—C1−2.83 (8)Zn1—S4—C8—S3−0.32 (11)
S4—Zn1—S1—C1−174.81 (8)Zn1—S3—C8—N2−179.31 (18)
N3—Zn1—S2—C1−122.35 (9)Zn1—S3—C8—S40.35 (12)
S3—Zn1—S2—C1121.38 (8)C8—N2—C9—C10−87.7 (3)
S1—Zn1—S2—C12.88 (8)C12—N2—C9—C1089.4 (2)
S4—Zn1—S2—C134.02 (12)N2—C9—C10—C11−173.2 (2)
N3—Zn1—S3—C890.13 (10)C8—N2—C12—C13−82.4 (3)
S1—Zn1—S3—C8−83.78 (8)C9—N2—C12—C13100.6 (2)
S2—Zn1—S3—C8−163.92 (7)N2—C12—C13—C14−53.5 (3)
S4—Zn1—S3—C8−0.21 (7)C19—N3—C15—C161.3 (3)
N3—Zn1—S4—C8−111.38 (9)Zn1—N3—C15—C16179.25 (17)
S3—Zn1—S4—C80.22 (8)N3—C15—C16—C17−1.1 (4)
S1—Zn1—S4—C8121.93 (8)C15—C16—C17—C180.2 (3)
S2—Zn1—S4—C892.17 (11)C15—C16—C17—C20177.9 (2)
N4—Zn2—S5—C2783.52 (10)C16—C17—C18—C190.5 (4)
S7—Zn2—S5—C27−91.36 (8)C20—C17—C18—C19−177.2 (2)
S8—Zn2—S5—C27−168.71 (8)C15—N3—C19—C18−0.5 (4)
S6—Zn2—S5—C27−0.27 (8)Zn1—N3—C19—C18−178.53 (19)
N4—Zn2—S6—C27−123.49 (9)C17—C18—C19—N3−0.4 (4)
S5—Zn2—S6—C270.28 (8)C16—C17—C20—C21−94.6 (3)
S7—Zn2—S6—C27122.90 (8)C18—C17—C20—C2183.0 (3)
S8—Zn2—S6—C2763.46 (13)C17—C20—C21—C22−179.6 (2)
N4—Zn2—S7—C3490.49 (10)C20—C21—C22—C23−122.9 (2)
S5—Zn2—S7—C34−94.13 (8)C20—C21—C22—C2657.3 (3)
S8—Zn2—S7—C34−1.74 (7)C26—C22—C23—C240.8 (3)
S6—Zn2—S7—C34−170.32 (8)C21—C22—C23—C24−179.1 (2)
N4—Zn2—S8—C34−109.09 (9)C25—N4—C24—C23−1.0 (3)
S5—Zn2—S8—C34124.24 (8)Zn2—N4—C24—C23−179.50 (18)
S7—Zn2—S8—C341.78 (8)C22—C23—C24—N40.2 (4)
S6—Zn2—S8—C3463.91 (12)C24—N4—C25—C260.7 (3)
S3—Zn1—N3—C1990.38 (18)Zn2—N4—C25—C26179.25 (18)
S1—Zn1—N3—C19−96.06 (18)N4—C25—C26—C220.3 (4)
S2—Zn1—N3—C19−20.87 (18)C23—C22—C26—C25−1.0 (3)
S4—Zn1—N3—C19165.37 (17)C21—C22—C26—C25178.8 (2)
S3—Zn1—N3—C15−87.53 (18)C31—N5—C27—S6174.39 (17)
S1—Zn1—N3—C1586.03 (18)C28—N5—C27—S6−1.5 (3)
S2—Zn1—N3—C15161.22 (17)C31—N5—C27—S5−6.4 (3)
S4—Zn1—N3—C15−12.54 (18)C28—N5—C27—S5177.64 (16)
S5—Zn2—N4—C24−41.6 (2)Zn2—S6—C27—N5178.8 (2)
S7—Zn2—N4—C24133.80 (17)Zn2—S6—C27—S5−0.41 (11)
S8—Zn2—N4—C24−150.88 (18)Zn2—S5—C27—N5−178.76 (18)
S6—Zn2—N4—C2430.66 (18)Zn2—S5—C27—S60.45 (13)
S5—Zn2—N4—C25139.88 (16)C27—N5—C28—C29−89.1 (3)
S7—Zn2—N4—C25−44.70 (19)C31—N5—C28—C2994.7 (2)
S8—Zn2—N4—C2530.62 (18)N5—C28—C29—C30179.3 (2)
S6—Zn2—N4—C25−147.83 (17)C27—N5—C31—C32−89.0 (3)
C5—N1—C1—S22.1 (3)C28—N5—C31—C3287.1 (2)
C2—N1—C1—S2178.98 (18)N5—C31—C32—C33174.1 (2)
C5—N1—C1—S1−177.72 (17)C38—N6—C34—S8−179.81 (16)
C2—N1—C1—S1−0.9 (3)C35—N6—C34—S85.8 (3)
Zn1—S2—C1—N1175.9 (2)C38—N6—C34—S70.3 (3)
Zn1—S2—C1—S1−4.24 (11)C35—N6—C34—S7−174.08 (17)
Zn1—S1—C1—N1−175.59 (19)Zn2—S8—C34—N6177.6 (2)
Zn1—S1—C1—S24.54 (12)Zn2—S8—C34—S7−2.57 (11)
C1—N1—C2—C3103.4 (3)Zn2—S7—C34—N6−177.32 (18)
C5—N1—C2—C3−79.6 (3)Zn2—S7—C34—S82.82 (12)
N1—C2—C3—C4−65.2 (3)C34—N6—C35—C36−112.6 (2)
C1—N1—C5—C687.4 (3)C38—N6—C35—C3672.7 (3)
C2—N1—C5—C6−89.7 (3)N6—C35—C36—C3763.7 (3)
N1—C5—C6—C7176.1 (2)C34—N6—C38—C39−84.9 (3)
C9—N2—C8—S41.6 (3)C35—N6—C38—C3990.0 (2)
C12—N2—C8—S4−175.34 (16)N6—C38—C39—C40171.8 (2)
C9—N2—C8—S3−178.76 (16)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C28—H28a···S1i0.992.823.706 (3)149
C40—H40b···S3ii0.982.873.834 (3)170
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2.
Table 1
Selected geometric parameters (Å, °) top
Zn1—S12.3627 (8)Zn2—S52.3295 (8)
Zn1—S22.5573 (8)Zn2—S62.6166 (9)
Zn1—S32.3437 (8)Zn2—S72.3327 (9)
Zn1—S42.5978 (8)Zn2—S82.5829 (8)
Zn1—N32.0882 (19)Zn2—N42.0691 (19)
N3—Zn1—S1125.92 (6)S5—Zn2—S7124.05 (3)
S2—Zn1—S4164.37 (2)S6—Zn2—S8167.27 (2)
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C28—H28a···S1i0.992.823.706 (3)149
C40—H40b···S3ii0.982.873.834 (3)170
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+1, y+1/2, −z+1/2.
references
References top

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