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Acta Crystallogr Sect E Struct Rep Online. 2010 September 1; 66(Pt 9): m1165–m1166.
Published online 2010 August 28. doi:  10.1107/S1600536810033672
PMCID: PMC3008025

Bis(N-sec-butyl-N-n-propyl­dithio­carbamato-κ2 S,S′)(1,10-phenanthroline-κ2 N,N′)zinc(II)

Abstract

Two independent but very similar mol­ecules comprise the asymmetric unit of the title compound, [Zn(C8H16NS2)2(C12H8N2)]. The N2S4 donor set about Zn is defined by two symmetrically chelating dithio­carbamate ligands and a 1,10-phenanthroline ligand. Distortions from the ideal octa­hedral coordination geometry arise from the restricted bite angles of the ligands. The main feature of the crystal packing is the formation of tetra­meric supra­molecular aggregates mediated by C—H(...)S inter­actions. Disorder was found in each of the sec-butyl groups. This was resolved over two positions in each case with the major components of the disorder having site occupancies in the range 0.551 (6)–0.725 (5).

Related literature

For a review on the supra­molecular aggregation patterns of zinc-triad dithio­carbamates, see: Tiekink (2003 [triangle]). For crystal engineering studies on dithio­carbamates and their zinc compounds, see: Benson et al. (2007 [triangle]); Howie et al. (2008 [triangle]). For the structure of the mononuclear binary precursor compound, see: Awang et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1165-scheme1.jpg

Experimental

Crystal data

  • [Zn(C8H16NS2)2(C12H8N2)]
  • M r = 626.25
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1165-efi1.jpg
  • a = 13.4195 (5) Å
  • b = 14.3946 (5) Å
  • c = 16.6444 (5) Å
  • α = 92.727 (3)°
  • β = 90.998 (3)°
  • γ = 103.368 (3)°
  • V = 3123.18 (18) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 1.08 mm−1
  • T = 100 K
  • 0.30 × 0.25 × 0.10 mm

Data collection

  • Oxford Diffraction Xcaliber Eos Gemini diffractometer
  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 [triangle]) T min = 0.824, T max = 1.000
  • 53206 measured reflections
  • 14179 independent reflections
  • 10260 reflections with I > 2σ(I)
  • R int = 0.034

Refinement

  • R[F 2 > 2σ(F 2)] = 0.034
  • wR(F 2) = 0.099
  • S = 1.05
  • 14179 reflections
  • 790 parameters
  • 302 restraints
  • H-atom parameters constrained
  • Δρmax = 1.32 e Å−3
  • Δρmin = −0.59 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 [triangle]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]) and DIAMOND (Brandenburg, 2006 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033672/bt5329sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033672/bt5329Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank UKM (UKM-GUP-NBT-08–27-111 and UKM-ST-06-FRGS0092–2010), UPM and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

Dithiocarbamate anions (Howie et al., 2008) and their zinc derivatives, including their adducts with nitrogen-containing bases (Benson et al., 2007), attract attention in crystal engineering endeavours. Often the polynuclear structures found in the structures of the parent binary precursor compounds are broken down in the presence of base. However, in the present study, the parent binary compound Zn[S2N(sec-Bu)(n-Pr)]2 (Awang et al., 2010) was found to be mononuclear in its crystal structure, an observation consistent with the influence of the relatively large iso-butyl groups (Tiekink, 2003). Not surprisingly, its 1:1 1,10-phenanthroline adduct, (I), is also mononuclear.

The crystallographic asymmetric unit of (I) comprises two very similar molecules, Figs 1 and 2. Each Zn atom is coordinated by two dithiocarbamate ligands which form similar Zn–S bond distances, Table 1, with the range being relatively narrow, i.e. 2.4881 (6) Å, for Zn2–S6, to 2.5311 (6) Å, for Zn1–S2. Similarly, the Zn–N bond distances span a narrow range, Table 1. The coordination geometry is based on an octahedron with deviations related to the restricted bite distances of the chelating ligands.

The presence of C–H···S interactions, Table 1, lead to the formation of tetrameric supramolecular aggregates in the crystal structure of (I). The S8 atom is pivotal in these. The molecules comprising the asymmetric unit are connected by the C–H···S8 interaction involving the C28–H28a atom. The dimeric aggregates thus formed are linked via the C–H···S8 interaction involving the C50–H50 atom, Fig. 3. Globally, the molecules pack into layers parallel to (0 1 1) and inter-digitate, Fig. 4.

Experimental

Carbon disulfide (20 mmol) was dropped into an ethanol solution (100 ml) of N-sec-butyl-N-n-propylamine (20 mmol). The solution was kept at 273 K for an hour. Zinc chloride (10 mmol) dissolved in ethanol (50 ml) was added to give a white precipitate. This was collected and redissolved in chloroform (50 ml). The solution was mixed with a solution of 1,10-phenanthroline (10 mmol) dissolved in ethanol (10 mol). The yellow solution was set aside for the growth of crystals.

Refinement

H-atoms were placed in calculated positions (C—H 0.95 to 1.00 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2 to 1.5Uequiv(C).

All sec-butyl groups were found to be disordered. For each group, the site occupancies were refined. The major component had site occupancy factor of 0.551 (6) for the C5-containing group, 0.725 (5) for the C13-group, 0.587 (6) for the C33-group, and 0.557 (6) for the C41-group. For both the ordered n-propyl and disordered sec-butyl groups, the 1,2-related C–C distances were tightly restrained to 1.500±0.005 Å and the 1,3-related ones to 2.51±0.01 Å. Within the S2C–NC2 fragment, the S2C–N distances were restrained to 1.35±0.01 Å and the N–Calkyl distances to 1.45±0.01 Å. Finally, all anisotropic displacement parameters were refined individually except for the C33' and C36' atoms which were refined isotropically. Additionally, the anisotropic displacement parameters for the carbon atoms of both the ordered n-propyl and disordered sec-butyl groups were tightly restrained to be nearly isotropic.

The maximum and minimum residual electron density peaks of 1.32 and 0.59 eÅ-3, respectively, were located 0.50 Å and 0.28 Å from the H36b and C40 atoms, respectively.

Figures

Fig. 1.
The molecular structure of the first independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only the major components of the disordered atoms associated with the sec-butyl groups are shown ...
Fig. 2.
The molecular structure of the second independent molecule in (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. Only the major components of the disordered atoms associated with the sec-butyl groups are shown ...
Fig. 3.
Supramolecular tetrameric unit in (I) mediated by C–H···S interactions, shown as orange dashed lines. Hydrogen atoms not involved in the C–H···S interactions have been omitted for reasons ...
Fig. 4.
A view in projection down the a axis showing the inter-digitation of layers in (I).

Crystal data

[Zn(C8H16NS2)2(C12H8N2)]Z = 4
Mr = 626.25F(000) = 1320
Triclinic, P1Dx = 1.332 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.4195 (5) ÅCell parameters from 25754 reflections
b = 14.3946 (5) Åθ = 2.2–29.2°
c = 16.6444 (5) ŵ = 1.08 mm1
α = 92.727 (3)°T = 100 K
β = 90.998 (3)°Prism, yellow
γ = 103.368 (3)°0.30 × 0.25 × 0.10 mm
V = 3123.18 (18) Å3

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer14179 independent reflections
Radiation source: fine-focus sealed tube10260 reflections with I > 2σ(I)
graphiteRint = 0.034
Detector resolution: 16.1952 pixels mm-1θmax = 27.5°, θmin = 2.2°
ω scansh = −17→17
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)k = −18→18
Tmin = 0.824, Tmax = 1.000l = −21→21
53206 measured reflections

Refinement

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) = 0.099H-atom parameters constrained
S = 1.05w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3
14179 reflections(Δ/σ)max = 0.001
790 parametersΔρmax = 1.32 e Å3
302 restraintsΔρmin = −0.59 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
Zn10.239825 (18)0.874711 (17)0.166771 (14)0.02154 (7)
Zn20.801467 (18)0.639792 (17)0.331410 (14)0.02174 (7)
S10.35079 (4)1.00240 (4)0.25789 (3)0.02757 (13)
S20.12697 (4)0.96605 (4)0.24166 (3)0.02515 (13)
S30.23307 (4)0.72779 (4)0.24177 (3)0.02953 (14)
S40.36271 (5)0.78842 (4)0.10466 (3)0.02983 (14)
S50.79867 (4)0.78922 (4)0.26012 (3)0.02810 (13)
S60.67551 (4)0.71816 (4)0.39812 (3)0.02944 (13)
S70.68307 (4)0.50772 (4)0.25064 (4)0.02980 (14)
S80.90639 (4)0.56207 (4)0.23704 (3)0.02479 (13)
N10.23999 (13)1.10333 (14)0.34135 (11)0.0317 (5)
N20.37212 (14)0.63516 (13)0.18675 (11)0.0293 (4)
N30.25422 (13)0.96448 (13)0.06232 (10)0.0242 (4)
N40.09827 (13)0.81818 (12)0.09271 (10)0.0218 (4)
N50.66886 (13)0.88235 (13)0.33127 (11)0.0289 (4)
N60.78352 (14)0.42815 (15)0.13972 (13)0.0452 (6)
N70.80350 (14)0.55248 (13)0.43810 (11)0.0260 (4)
N80.94593 (13)0.70603 (12)0.39861 (10)0.0224 (4)
C10.23924 (16)1.03239 (14)0.28596 (12)0.0224 (5)
C20.33750 (16)1.15812 (17)0.37841 (13)0.0342 (6)
H2A0.38151.11330.38930.041*
H2B0.32331.18720.43080.041*
C30.39618 (19)1.23626 (19)0.32837 (15)0.0455 (7)
H3A0.40491.20910.27390.055*
H3B0.35651.28580.32270.055*
C40.5000 (2)1.2816 (2)0.36624 (19)0.0721 (10)
H4A0.53621.33190.33250.108*
H4B0.53981.23290.37110.108*
H4C0.49151.30960.41980.108*
C50.1437 (4)1.1151 (4)0.3785 (4)0.045 (2)0.551 (6)
H50.08541.07190.34730.054*0.551 (6)
C60.1371 (5)1.2168 (4)0.3660 (3)0.0583 (19)0.551 (6)
H6A0.19841.26070.39170.070*0.551 (6)
H6B0.07631.22880.39360.070*0.551 (6)
C70.1300 (10)1.2400 (7)0.2786 (4)0.077 (3)0.551 (6)
H7A0.12561.30680.27550.115*0.551 (6)
H7B0.06881.19790.25280.115*0.551 (6)
H7C0.19111.23040.25110.115*0.551 (6)
C80.1342 (9)1.0898 (6)0.4651 (4)0.057 (3)0.551 (6)
H8A0.13911.02330.46960.086*0.551 (6)
H8B0.06791.09720.48460.086*0.551 (6)
H8C0.18951.13220.49750.086*0.551 (6)
C5'0.1483 (5)1.1437 (5)0.3539 (4)0.035 (2)0.449 (6)
H5'0.09021.09220.33090.041*0.449 (6)
C6'0.1248 (5)1.1511 (4)0.4421 (3)0.0372 (17)0.449 (6)
H6'A0.17281.20790.46790.045*0.449 (6)
H6'B0.05461.16100.44720.045*0.449 (6)
C7'0.1329 (12)1.0645 (7)0.4866 (6)0.047 (2)0.449 (6)
H7'A0.11551.07340.54290.071*0.449 (6)
H7'B0.20301.05580.48400.071*0.449 (6)
H7'C0.08531.00790.46180.071*0.449 (6)
C8'0.1378 (10)1.2314 (7)0.3107 (5)0.062 (3)0.449 (6)
H8'A0.15461.22390.25410.094*0.449 (6)
H8'B0.18471.28810.33590.094*0.449 (6)
H8'C0.06721.23880.31420.094*0.449 (6)
C90.32818 (16)0.70920 (15)0.17887 (13)0.0245 (5)
C100.44458 (17)0.61559 (17)0.12801 (15)0.0392 (6)
H10A0.42030.62780.07390.047*
H10B0.44510.54690.12820.047*
C110.55093 (17)0.67274 (19)0.14187 (16)0.0450 (7)
H11A0.57800.65780.19420.054*
H11B0.55130.74170.14400.054*
C120.6207 (2)0.6506 (2)0.07366 (19)0.0656 (10)
H12A0.69050.68910.08380.098*
H12B0.59430.66600.02190.098*
H12C0.62130.58250.07220.098*
C130.3381 (3)0.5637 (3)0.2476 (2)0.0340 (16)*0.725 (5)
H130.31270.60040.29220.041*0.725 (5)
C140.2466 (3)0.4848 (3)0.2225 (3)0.0404 (11)0.725 (5)
H14A0.19080.51380.20410.048*0.725 (5)
H14B0.22250.44840.27030.048*0.725 (5)
C150.2658 (4)0.4155 (3)0.1566 (2)0.0670 (15)0.725 (5)
H15A0.20270.36660.14430.101*0.725 (5)
H15B0.31980.38500.17460.101*0.725 (5)
H15C0.28740.45020.10830.101*0.725 (5)
C160.4247 (3)0.5297 (4)0.2862 (3)0.0372 (12)0.725 (5)
H16A0.48100.58470.30130.056*0.725 (5)
H16B0.44890.48640.24800.056*0.725 (5)
H16C0.40040.49570.33440.056*0.725 (5)
C13'0.3510 (9)0.5757 (8)0.2572 (5)0.027 (3)*0.275 (5)
H13'0.31490.60940.29720.033*0.275 (5)
C14'0.4455 (9)0.5609 (11)0.2977 (8)0.064 (6)0.275 (5)
H14C0.48170.52820.25800.076*0.275 (5)
H14D0.49070.62460.31160.076*0.275 (5)
C15'0.4339 (7)0.5057 (7)0.3715 (5)0.050 (3)0.275 (5)
H15D0.37760.44890.36310.075*0.275 (5)
H15E0.41890.54580.41690.075*0.275 (5)
H15F0.49760.48610.38330.075*0.275 (5)
C16'0.2764 (14)0.4862 (13)0.2259 (16)0.158 (12)0.275 (5)
H16D0.30660.45640.18130.237*0.275 (5)
H16E0.21320.50220.20690.237*0.275 (5)
H16F0.26080.44160.26910.237*0.275 (5)
C170.33347 (18)1.03520 (17)0.04694 (14)0.0329 (5)
H170.39301.04620.08100.040*
C180.33270 (19)1.09401 (18)−0.01748 (15)0.0397 (6)
H180.39111.1434−0.02690.048*
C190.24760 (19)1.07993 (18)−0.06662 (14)0.0362 (6)
H190.24531.1210−0.10930.043*
C200.16330 (17)1.00413 (16)−0.05364 (13)0.0278 (5)
C210.17103 (16)0.94775 (15)0.01207 (12)0.0228 (5)
C220.07059 (18)0.98366 (18)−0.10259 (13)0.0333 (6)
H220.06541.0209−0.14740.040*
C23−0.00922 (18)0.91165 (17)−0.08521 (13)0.0315 (5)
H23−0.07010.8998−0.11780.038*
C24−0.00404 (16)0.85280 (16)−0.01878 (13)0.0262 (5)
C250.08632 (15)0.87023 (15)0.02919 (12)0.0216 (4)
C26−0.08585 (17)0.77978 (17)0.00372 (14)0.0323 (6)
H26−0.14880.7656−0.02640.039*
C27−0.07429 (17)0.72921 (17)0.06938 (14)0.0322 (5)
H27−0.12950.68030.08570.039*
C280.01936 (16)0.74993 (16)0.11228 (13)0.0268 (5)
H28A0.02670.71360.15730.032*
C290.70977 (16)0.80548 (15)0.33003 (13)0.0260 (5)
C300.59164 (16)0.89209 (18)0.39022 (15)0.0386 (6)
H30A0.59070.96050.39760.046*
H30B0.61220.87120.44250.046*
C310.48387 (16)0.83533 (19)0.36736 (15)0.0405 (6)
H31A0.46270.85570.31500.049*
H31B0.48380.76660.36090.049*
C320.4074 (2)0.8491 (3)0.42999 (17)0.0604 (9)
H32A0.33910.81130.41320.091*
H32B0.40610.91690.43560.091*
H32C0.42750.82810.48170.091*
C330.7071 (4)0.9658 (3)0.2849 (3)0.0330 (17)*0.587 (6)
H330.75360.94810.24360.040*0.587 (6)
C340.7694 (5)1.0455 (5)0.3393 (3)0.048 (2)0.587 (6)
H34A0.81801.02050.37270.057*0.587 (6)
H34B0.72341.07120.37560.057*0.587 (6)
C350.8275 (6)1.1239 (5)0.2903 (4)0.110 (3)0.587 (6)
H35A0.86951.17440.32620.165*0.587 (6)
H35B0.77911.15050.25910.165*0.587 (6)
H35C0.87191.09810.25350.165*0.587 (6)
C360.6203 (5)0.9954 (6)0.2410 (5)0.0475 (17)0.587 (6)
H36A0.58120.94110.20730.071*0.587 (6)
H36B0.64861.04850.20720.071*0.587 (6)
H36C0.57501.01570.28030.071*0.587 (6)
C33'0.6986 (5)0.9574 (4)0.2709 (4)0.032 (2)*0.413 (6)
H33'0.74320.93260.23170.039*0.413 (6)
C34'0.7623 (6)1.0510 (6)0.3072 (6)0.047 (3)0.413 (6)
H34C0.77381.09840.26510.056*0.413 (6)
H34D0.72281.07490.35000.056*0.413 (6)
C35'0.8640 (5)1.0453 (6)0.3423 (5)0.071 (3)0.413 (6)
H35D0.89701.10680.36980.107*0.413 (6)
H35E0.90761.03050.29920.107*0.413 (6)
H35F0.85410.99500.38100.107*0.413 (6)
C36'0.6090 (7)0.9754 (7)0.2220 (6)0.032 (2)*0.413 (6)
H36D0.57180.91550.19440.048*0.413 (6)
H36E0.63451.02250.18210.048*0.413 (6)
H36F0.56270.99990.25790.048*0.413 (6)
C370.79047 (17)0.49164 (15)0.20281 (13)0.0273 (5)
C380.6826 (2)0.3684 (2)0.11202 (16)0.0580 (9)
H38A0.68620.34800.05470.070*
H38B0.63090.40740.11590.070*
C390.6487 (2)0.2819 (2)0.15941 (19)0.0749 (11)
H39A0.64870.30120.21730.090*
H39B0.69680.23960.15230.090*
C400.5406 (3)0.2280 (3)0.1309 (2)0.1136 (18)
H40A0.51840.17150.16240.170*
H40B0.54110.20820.07390.170*
H40C0.49310.27010.13840.170*
C410.8671 (4)0.4267 (4)0.0836 (3)0.0364 (15)0.557 (6)
H410.92920.47510.10450.044*0.557 (6)
C420.8886 (4)0.3293 (4)0.0892 (3)0.0545 (18)0.557 (6)
H42A0.94710.32580.05470.065*0.557 (6)
H42B0.82820.28120.06680.065*0.557 (6)
C430.9128 (9)0.3019 (7)0.1721 (5)0.066 (3)0.557 (6)
H43A0.92470.23710.16910.100*0.557 (6)
H43B0.85510.30360.20700.100*0.557 (6)
H43C0.97440.34700.19430.100*0.557 (6)
C440.8444 (9)0.4498 (6)−0.0015 (4)0.046 (2)0.557 (6)
H44A0.83130.5140−0.00130.069*0.557 (6)
H44B0.78380.4030−0.02340.069*0.557 (6)
H44C0.90320.4473−0.03490.069*0.557 (6)
C41'0.8808 (5)0.4012 (6)0.1153 (3)0.045 (2)0.443 (6)
H41'0.93340.46300.12180.054*0.443 (6)
C42'0.8747 (5)0.3790 (5)0.0256 (3)0.053 (2)0.443 (6)
H42C0.93990.36430.00860.064*0.443 (6)
H42D0.81930.32110.01320.064*0.443 (6)
C43'0.8546 (13)0.4592 (9)−0.0221 (6)0.062 (4)0.443 (6)
H43D0.85910.51610.01380.093*0.443 (6)
H43E0.78600.4401−0.04740.093*0.443 (6)
H43F0.90580.4739−0.06380.093*0.443 (6)
C44'0.9294 (11)0.3322 (8)0.1591 (6)0.062 (3)0.443 (6)
H44D0.88510.26760.15250.093*0.443 (6)
H44E0.93800.35190.21650.093*0.443 (6)
H44F0.99640.33230.13670.093*0.443 (6)
C450.73245 (19)0.47705 (18)0.45705 (15)0.0377 (6)
H450.67380.45610.42240.045*
C460.7400 (2)0.4268 (2)0.52591 (16)0.0456 (7)
H460.68700.37320.53740.055*
C470.8238 (2)0.45501 (19)0.57653 (15)0.0408 (7)
H470.83020.42100.62310.049*
C480.90100 (19)0.53560 (18)0.55858 (13)0.0329 (6)
C490.88660 (17)0.58166 (16)0.48816 (12)0.0253 (5)
C500.9926 (2)0.5698 (2)0.60707 (14)0.0389 (6)
H501.00190.53910.65500.047*
C511.0654 (2)0.6444 (2)0.58583 (14)0.0389 (6)
H511.12580.66510.61870.047*
C521.05418 (17)0.69385 (17)0.51424 (13)0.0295 (5)
C530.96394 (16)0.66307 (16)0.46640 (12)0.0230 (5)
C541.12855 (18)0.77028 (19)0.48772 (14)0.0360 (6)
H541.19090.79310.51780.043*
C551.11122 (17)0.81217 (17)0.41822 (14)0.0331 (5)
H551.16190.86330.39930.040*
C561.01803 (16)0.77887 (16)0.37545 (13)0.0276 (5)
H561.00590.80950.32810.033*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Zn10.02242 (14)0.01901 (13)0.02348 (13)0.00553 (10)−0.00139 (10)0.00109 (10)
Zn20.02268 (14)0.02026 (14)0.02312 (14)0.00700 (10)−0.00043 (10)0.00007 (10)
S10.0223 (3)0.0292 (3)0.0326 (3)0.0100 (2)−0.0038 (2)−0.0026 (2)
S20.0220 (3)0.0253 (3)0.0270 (3)0.0048 (2)−0.0031 (2)−0.0052 (2)
S30.0270 (3)0.0299 (3)0.0344 (3)0.0102 (2)0.0060 (2)0.0094 (3)
S40.0375 (3)0.0279 (3)0.0285 (3)0.0150 (3)0.0082 (3)0.0073 (2)
S50.0269 (3)0.0256 (3)0.0352 (3)0.0124 (2)0.0033 (2)0.0047 (2)
S60.0309 (3)0.0336 (3)0.0273 (3)0.0149 (3)0.0017 (2)0.0003 (2)
S70.0224 (3)0.0293 (3)0.0374 (3)0.0065 (2)0.0035 (2)−0.0054 (3)
S80.0227 (3)0.0235 (3)0.0271 (3)0.0041 (2)0.0004 (2)−0.0031 (2)
N10.0226 (10)0.0339 (12)0.0341 (11)0.0005 (9)0.0029 (8)−0.0131 (9)
N20.0361 (11)0.0242 (10)0.0304 (10)0.0119 (9)0.0076 (9)0.0037 (8)
N30.0241 (10)0.0224 (10)0.0264 (10)0.0056 (8)−0.0008 (8)0.0026 (8)
N40.0230 (9)0.0203 (9)0.0219 (9)0.0055 (8)0.0009 (7)−0.0021 (7)
N50.0258 (10)0.0263 (11)0.0368 (11)0.0123 (8)−0.0015 (8)−0.0046 (8)
N60.0287 (11)0.0439 (14)0.0523 (14)−0.0080 (10)0.0143 (10)−0.0273 (11)
N70.0278 (10)0.0255 (10)0.0266 (10)0.0099 (8)0.0054 (8)0.0024 (8)
N80.0234 (9)0.0229 (10)0.0227 (9)0.0097 (8)0.0018 (7)−0.0017 (7)
C10.0253 (11)0.0206 (11)0.0203 (10)0.0031 (9)0.0008 (9)0.0032 (9)
C20.0275 (13)0.0417 (15)0.0266 (12)−0.0032 (11)−0.0007 (10)−0.0124 (10)
C30.0458 (16)0.0363 (15)0.0463 (16)−0.0059 (12)−0.0011 (13)−0.0011 (12)
C40.0567 (19)0.071 (2)0.066 (2)−0.0306 (17)−0.0016 (16)0.0080 (18)
C50.026 (3)0.046 (4)0.053 (4)−0.006 (3)0.019 (3)−0.024 (3)
C60.047 (3)0.063 (4)0.069 (4)0.029 (3)−0.009 (3)−0.031 (3)
C70.094 (5)0.061 (5)0.086 (6)0.044 (4)−0.031 (5)0.001 (4)
C80.051 (4)0.061 (6)0.051 (5)−0.001 (5)0.024 (4)−0.011 (4)
C5'0.027 (3)0.030 (4)0.043 (4)0.004 (3)0.009 (3)−0.013 (3)
C6'0.035 (3)0.038 (4)0.040 (4)0.014 (3)0.002 (3)−0.007 (3)
C7'0.049 (5)0.052 (5)0.042 (5)0.014 (4)0.010 (4)0.012 (4)
C8'0.077 (6)0.070 (5)0.060 (6)0.055 (4)0.007 (6)0.020 (5)
C90.0271 (12)0.0204 (11)0.0262 (11)0.0066 (9)−0.0014 (9)0.0003 (9)
C100.0447 (15)0.0330 (14)0.0461 (15)0.0199 (12)0.0108 (12)0.0066 (12)
C110.0398 (15)0.0392 (16)0.0599 (18)0.0149 (12)0.0053 (13)0.0117 (13)
C120.0481 (18)0.060 (2)0.098 (3)0.0249 (16)0.0317 (18)0.0305 (19)
C140.042 (2)0.025 (2)0.053 (3)0.0022 (16)0.0203 (19)0.0114 (17)
C150.079 (3)0.045 (3)0.069 (3)0.002 (2)−0.005 (2)−0.003 (2)
C160.034 (2)0.031 (3)0.050 (3)0.010 (2)0.0083 (19)0.0180 (19)
C14'0.044 (7)0.057 (9)0.078 (8)−0.021 (6)−0.008 (6)0.040 (7)
C15'0.049 (6)0.050 (6)0.059 (6)0.024 (5)0.015 (5)0.017 (5)
C16'0.170 (15)0.151 (15)0.141 (14)0.014 (10)−0.012 (9)0.014 (9)
C170.0285 (13)0.0287 (13)0.0394 (14)0.0013 (10)−0.0022 (11)0.0066 (11)
C180.0398 (15)0.0341 (15)0.0423 (15)−0.0001 (12)0.0058 (12)0.0140 (12)
C190.0452 (15)0.0341 (14)0.0313 (13)0.0108 (12)0.0070 (11)0.0131 (11)
C200.0354 (13)0.0298 (13)0.0221 (11)0.0158 (11)0.0013 (10)0.0006 (9)
C210.0260 (12)0.0241 (12)0.0208 (11)0.0110 (9)0.0024 (9)−0.0004 (9)
C220.0429 (15)0.0420 (15)0.0216 (11)0.0234 (12)−0.0022 (10)0.0012 (10)
C230.0330 (13)0.0389 (14)0.0263 (12)0.0189 (11)−0.0076 (10)−0.0083 (10)
C240.0268 (12)0.0290 (13)0.0251 (11)0.0134 (10)−0.0037 (9)−0.0085 (9)
C250.0229 (11)0.0217 (11)0.0217 (11)0.0092 (9)0.0007 (9)−0.0043 (9)
C260.0225 (12)0.0352 (14)0.0390 (14)0.0099 (10)−0.0056 (10)−0.0137 (11)
C270.0234 (12)0.0302 (13)0.0401 (14)0.0021 (10)0.0029 (10)−0.0070 (11)
C280.0265 (12)0.0233 (12)0.0294 (12)0.0039 (10)0.0030 (10)−0.0027 (9)
C290.0219 (11)0.0245 (12)0.0310 (12)0.0065 (9)−0.0065 (9)−0.0057 (9)
C300.0385 (14)0.0426 (15)0.0417 (14)0.0246 (12)0.0040 (12)−0.0043 (12)
C310.0315 (14)0.0462 (16)0.0489 (16)0.0175 (12)0.0086 (12)0.0094 (13)
C320.0468 (17)0.091 (3)0.0545 (18)0.0339 (17)0.0156 (14)0.0254 (17)
C340.051 (4)0.037 (3)0.048 (4)−0.005 (3)−0.006 (3)0.001 (3)
C350.143 (7)0.078 (5)0.105 (5)0.017 (5)0.009 (5)0.007 (4)
C360.050 (3)0.042 (4)0.057 (4)0.022 (3)0.001 (3)0.000 (3)
C34'0.044 (5)0.040 (5)0.052 (6)0.001 (4)0.010 (4)−0.008 (4)
C35'0.084 (6)0.059 (5)0.065 (5)0.008 (4)0.001 (4)−0.012 (4)
C370.0262 (12)0.0230 (12)0.0309 (12)0.0030 (10)0.0040 (10)−0.0029 (10)
C380.0557 (18)0.058 (2)0.0447 (17)−0.0132 (15)0.0106 (14)−0.0243 (14)
C390.083 (2)0.062 (2)0.064 (2)−0.0119 (19)0.0188 (19)−0.0179 (18)
C400.090 (3)0.132 (4)0.068 (2)−0.074 (3)0.020 (2)−0.030 (2)
C410.038 (3)0.039 (3)0.027 (3)0.000 (2)0.015 (2)−0.006 (2)
C420.058 (3)0.062 (4)0.049 (4)0.028 (3)0.008 (3)−0.017 (3)
C430.087 (6)0.060 (6)0.069 (5)0.053 (5)−0.008 (4)−0.006 (4)
C440.048 (4)0.048 (4)0.030 (3)−0.013 (3)0.022 (4)−0.004 (3)
C41'0.038 (4)0.050 (5)0.044 (4)0.011 (3)0.010 (3)−0.023 (4)
C42'0.042 (4)0.062 (5)0.052 (4)0.012 (3)−0.004 (3)−0.020 (4)
C43'0.054 (6)0.081 (7)0.051 (6)0.012 (5)0.032 (5)−0.004 (5)
C44'0.068 (5)0.049 (6)0.069 (6)0.015 (5)0.011 (5)−0.011 (4)
C450.0364 (14)0.0336 (14)0.0424 (15)0.0045 (11)0.0082 (12)0.0099 (12)
C460.0530 (18)0.0359 (15)0.0495 (17)0.0093 (13)0.0200 (14)0.0184 (13)
C470.0585 (18)0.0406 (16)0.0337 (14)0.0283 (14)0.0205 (13)0.0171 (12)
C480.0450 (15)0.0402 (15)0.0238 (12)0.0291 (12)0.0102 (11)0.0060 (10)
C490.0302 (12)0.0283 (12)0.0226 (11)0.0171 (10)0.0064 (9)0.0014 (9)
C500.0533 (17)0.0552 (18)0.0201 (12)0.0364 (14)0.0053 (11)0.0042 (11)
C510.0392 (15)0.0610 (19)0.0250 (12)0.0316 (14)−0.0050 (11)−0.0066 (12)
C520.0298 (13)0.0397 (14)0.0229 (11)0.0180 (11)−0.0003 (10)−0.0079 (10)
C530.0250 (11)0.0291 (12)0.0193 (10)0.0160 (10)0.0022 (9)−0.0039 (9)
C540.0242 (12)0.0494 (16)0.0344 (13)0.0125 (11)−0.0071 (10)−0.0152 (12)
C550.0236 (12)0.0325 (14)0.0412 (14)0.0037 (10)0.0016 (11)−0.0059 (11)
C560.0266 (12)0.0270 (12)0.0287 (12)0.0062 (10)0.0011 (10)−0.0016 (10)

Geometric parameters (Å, °)

Zn1—N32.1998 (17)C16'—H16E0.9800
Zn1—N42.2133 (17)C16'—H16F0.9800
Zn1—S32.4912 (6)C17—C181.399 (3)
Zn1—S42.4930 (6)C17—H170.9500
Zn1—S12.5073 (6)C18—C191.363 (3)
Zn1—S22.5311 (6)C18—H180.9500
Zn2—N82.2106 (17)C19—C201.406 (3)
Zn2—N72.2272 (18)C19—H190.9500
Zn2—S62.4881 (6)C20—C211.409 (3)
Zn2—S72.4964 (6)C20—C221.439 (3)
Zn2—S52.5129 (6)C21—C251.440 (3)
Zn2—S82.5178 (6)C22—C231.353 (3)
S1—C11.717 (2)C22—H220.9500
S2—C11.719 (2)C23—C241.435 (3)
S3—C91.725 (2)C23—H230.9500
S4—C91.718 (2)C24—C261.403 (3)
S5—C291.727 (2)C24—C251.406 (3)
S6—C291.721 (2)C26—C271.368 (3)
S7—C371.715 (2)C26—H260.9500
S8—C371.720 (2)C27—C281.398 (3)
N1—C11.341 (2)C27—H270.9500
N1—C21.471 (2)C28—H28A0.9500
N1—C51.483 (4)C30—C311.520 (3)
N1—C5'1.491 (4)C30—H30A0.9900
N2—C91.342 (2)C30—H30B0.9900
N2—C101.454 (3)C31—C321.513 (3)
N2—C131.479 (3)C31—H31A0.9900
N2—C13'1.478 (5)C31—H31B0.9900
N3—C171.329 (3)C32—H32A0.9800
N3—C211.352 (3)C32—H32B0.9800
N4—C281.324 (3)C32—H32C0.9800
N4—C251.353 (3)C33—C341.504 (4)
N5—C291.344 (2)C33—C361.517 (4)
N5—C331.455 (4)C33—H331.0000
N5—C301.465 (2)C34—C351.501 (5)
N5—C33'1.502 (4)C34—H34A0.9900
N6—C371.346 (2)C34—H34B0.9900
N6—C411.476 (4)C35—H35A0.9800
N6—C381.479 (3)C35—H35B0.9800
N6—C41'1.502 (4)C35—H35C0.9800
N7—C451.324 (3)C36—H36A0.9800
N7—C491.354 (3)C36—H36B0.9800
N8—C561.329 (3)C36—H36C0.9800
N8—C531.356 (3)C33'—C34'1.511 (5)
C2—C31.510 (3)C33'—C36'1.519 (5)
C2—H2A0.9900C33'—H33'1.0000
C2—H2B0.9900C34'—C35'1.496 (5)
C3—C41.508 (3)C34'—H34C0.9900
C3—H3A0.9900C34'—H34D0.9900
C3—H3B0.9900C35'—H35D0.9800
C4—H4A0.9800C35'—H35E0.9800
C4—H4B0.9800C35'—H35F0.9800
C4—H4C0.9800C36'—H36D0.9800
C5—C81.504 (5)C36'—H36E0.9800
C5—C61.510 (4)C36'—H36F0.9800
C5—H51.0000C38—C391.491 (3)
C6—C71.513 (5)C38—H38A0.9900
C6—H6A0.9900C38—H38B0.9900
C6—H6B0.9900C39—C401.534 (3)
C7—H7A0.9800C39—H39A0.9900
C7—H7B0.9800C39—H39B0.9900
C7—H7C0.9800C40—H40A0.9800
C8—H8A0.9800C40—H40B0.9800
C8—H8B0.9800C40—H40C0.9800
C8—H8C0.9800C41—C421.502 (4)
C5'—C6'1.511 (5)C41—C441.511 (5)
C5'—C8'1.514 (5)C41—H411.0000
C5'—H5'1.0000C42—C431.504 (5)
C6'—C7'1.503 (5)C42—H42A0.9900
C6'—H6'A0.9900C42—H42B0.9900
C6'—H6'B0.9900C43—H43A0.9800
C7'—H7'A0.9800C43—H43B0.9800
C7'—H7'B0.9800C43—H43C0.9800
C7'—H7'C0.9800C44—H44A0.9800
C8'—H8'A0.9800C44—H44B0.9800
C8'—H8'B0.9800C44—H44C0.9800
C8'—H8'C0.9800C41'—C42'1.509 (4)
C10—C111.481 (3)C41'—C44'1.515 (5)
C10—H10A0.9900C41'—H41'1.0000
C10—H10B0.9900C42'—C43'1.504 (5)
C11—C121.552 (3)C42'—H42C0.9900
C11—H11A0.9900C42'—H42D0.9900
C11—H11B0.9900C43'—H43D0.9800
C12—H12A0.9800C43'—H43E0.9800
C12—H12B0.9800C43'—H43F0.9800
C12—H12C0.9800C44'—H44D0.9800
C13—C141.505 (4)C44'—H44E0.9800
C13—C161.508 (4)C44'—H44F0.9800
C13—H131.0000C45—C461.399 (3)
C14—C151.512 (4)C45—H450.9500
C14—H14A0.9900C46—C471.365 (4)
C14—H14B0.9900C46—H460.9500
C15—H15A0.9800C47—C481.413 (4)
C15—H15B0.9800C47—H470.9500
C15—H15C0.9800C48—C491.406 (3)
C16—H16A0.9800C48—C501.433 (4)
C16—H16B0.9800C49—C531.440 (3)
C16—H16C0.9800C50—C511.340 (4)
C13'—C14'1.489 (5)C50—H500.9500
C13'—C16'1.502 (5)C51—C521.440 (3)
C13'—H13'1.0000C51—H510.9500
C14'—C15'1.487 (5)C52—C541.398 (3)
C14'—H14C0.9900C52—C531.408 (3)
C14'—H14D0.9900C54—C551.370 (3)
C15'—H15D0.9800C54—H540.9500
C15'—H15E0.9800C55—C561.400 (3)
C15'—H15F0.9800C55—H550.9500
C16'—H16D0.9800C56—H560.9500
N3—Zn1—N474.71 (6)N3—C17—H17118.7
N3—Zn1—S3157.35 (5)C18—C17—H17118.7
N4—Zn1—S396.54 (5)C19—C18—C17119.6 (2)
N3—Zn1—S489.08 (5)C19—C18—H18120.2
N4—Zn1—S4102.50 (5)C17—C18—H18120.2
S3—Zn1—S472.192 (19)C18—C19—C20119.5 (2)
N3—Zn1—S194.18 (5)C18—C19—H19120.3
N4—Zn1—S1151.09 (5)C20—C19—H19120.3
S3—Zn1—S1102.47 (2)C19—C20—C21117.2 (2)
S4—Zn1—S1103.93 (2)C19—C20—C22123.3 (2)
N3—Zn1—S293.96 (5)C21—C20—C22119.5 (2)
N4—Zn1—S282.85 (5)N3—C21—C20122.9 (2)
S3—Zn1—S2105.81 (2)N3—C21—C25117.40 (18)
S4—Zn1—S2174.40 (2)C20—C21—C25119.6 (2)
S1—Zn1—S271.186 (18)C23—C22—C20120.4 (2)
N8—Zn2—N774.40 (7)C23—C22—H22119.8
N8—Zn2—S6102.68 (5)C20—C22—H22119.8
N7—Zn2—S689.67 (5)C22—C23—C24121.6 (2)
N8—Zn2—S7153.90 (5)C22—C23—H23119.2
N7—Zn2—S793.72 (5)C24—C23—H23119.2
S6—Zn2—S7100.36 (2)C26—C24—C25117.0 (2)
N8—Zn2—S593.35 (5)C26—C24—C23123.8 (2)
N7—Zn2—S5155.36 (5)C25—C24—C23119.1 (2)
S6—Zn2—S571.94 (2)N4—C25—C24123.2 (2)
S7—Zn2—S5105.38 (2)N4—C25—C21117.05 (18)
N8—Zn2—S887.39 (5)C24—C25—C21119.71 (19)
N7—Zn2—S899.97 (5)C27—C26—C24119.5 (2)
S6—Zn2—S8167.69 (2)C27—C26—H26120.3
S7—Zn2—S871.587 (19)C24—C26—H26120.3
S5—Zn2—S8100.75 (2)C26—C27—C28119.5 (2)
C1—S1—Zn186.21 (7)C26—C27—H27120.2
C1—S2—Zn185.43 (7)C28—C27—H27120.2
C9—S3—Zn185.23 (7)N4—C28—C27122.6 (2)
C9—S4—Zn185.31 (7)N4—C28—H28A118.7
C29—S5—Zn285.15 (7)C27—C28—H28A118.7
C29—S6—Zn286.06 (7)N5—C29—S6121.38 (16)
C37—S7—Zn285.90 (7)N5—C29—S5121.80 (17)
C37—S8—Zn285.13 (7)S6—C29—S5116.82 (12)
C1—N1—C2120.16 (18)N5—C30—C31114.43 (19)
C1—N1—C5120.8 (3)N5—C30—H30A108.7
C2—N1—C5117.9 (3)C31—C30—H30A108.7
C1—N1—C5'121.6 (4)N5—C30—H30B108.7
C2—N1—C5'116.8 (4)C31—C30—H30B108.7
C9—N2—C10120.25 (18)H30A—C30—H30B107.6
C9—N2—C13121.4 (2)C32—C31—C30112.0 (2)
C10—N2—C13117.8 (2)C32—C31—H31A109.2
C9—N2—C13'120.2 (5)C30—C31—H31A109.2
C10—N2—C13'119.4 (5)C32—C31—H31B109.2
C17—N3—C21118.16 (19)C30—C31—H31B109.2
C17—N3—Zn1126.42 (15)H31A—C31—H31B107.9
C21—N3—Zn1115.32 (13)C31—C32—H32A109.5
C28—N4—C25118.08 (18)C31—C32—H32B109.5
C28—N4—Zn1125.97 (14)H32A—C32—H32B109.5
C25—N4—Zn1114.93 (13)C31—C32—H32C109.5
C29—N5—C33123.7 (3)H32A—C32—H32C109.5
C29—N5—C30120.03 (19)H32B—C32—H32C109.5
C33—N5—C30115.6 (3)N5—C33—C34109.6 (4)
C29—N5—C33'120.8 (4)N5—C33—C36111.2 (5)
C30—N5—C33'119.2 (4)C34—C33—C36112.4 (5)
C37—N6—C41124.0 (3)N5—C33—H33107.8
C37—N6—C38120.24 (19)C34—C33—H33107.8
C41—N6—C38114.5 (3)C36—C33—H33107.8
C37—N6—C41'116.8 (3)C33—C34—C35110.2 (4)
C38—N6—C41'120.7 (3)C33—C34—H34A109.6
C45—N7—C49117.9 (2)C35—C34—H34A109.6
C45—N7—Zn2126.87 (16)C33—C34—H34B109.6
C49—N7—Zn2115.19 (14)C35—C34—H34B109.6
C56—N8—C53118.30 (19)H34A—C34—H34B108.1
C56—N8—Zn2125.75 (14)C34—C35—H35A109.5
C53—N8—Zn2115.78 (14)C34—C35—H35B109.5
N1—C1—S1121.14 (16)H35A—C35—H35B109.5
N1—C1—S2121.67 (16)C34—C35—H35C109.5
S1—C1—S2117.17 (12)H35A—C35—H35C109.5
N1—C2—C3114.70 (19)H35B—C35—H35C109.5
N1—C2—H2A108.6C33—C36—H36A109.5
C3—C2—H2A108.6C33—C36—H36B109.5
N1—C2—H2B108.6H36A—C36—H36B109.5
C3—C2—H2B108.6C33—C36—H36C109.5
H2A—C2—H2B107.6H36A—C36—H36C109.5
C4—C3—C2111.4 (2)H36B—C36—H36C109.5
C4—C3—H3A109.4N5—C33'—C34'113.2 (6)
C2—C3—H3A109.4N5—C33'—C36'114.1 (6)
C4—C3—H3B109.4C34'—C33'—C36'109.8 (5)
C2—C3—H3B109.4N5—C33'—H33'106.4
H3A—C3—H3B108.0C34'—C33'—H33'106.4
C3—C4—H4A109.5C36'—C33'—H33'106.4
C3—C4—H4B109.5C35'—C34'—C33'114.6 (6)
H4A—C4—H4B109.5C35'—C34'—H34C108.6
C3—C4—H4C109.5C33'—C34'—H34C108.6
H4A—C4—H4C109.5C35'—C34'—H34D108.6
H4B—C4—H4C109.5C33'—C34'—H34D108.6
N1—C5—C8114.4 (6)H34C—C34'—H34D107.6
N1—C5—C6106.3 (4)C34'—C35'—H35D109.5
C8—C5—C6113.1 (5)C34'—C35'—H35E109.5
N1—C5—H5107.6H35D—C35'—H35E109.5
C8—C5—H5107.6C34'—C35'—H35F109.5
C6—C5—H5107.6H35D—C35'—H35F109.5
C5—C6—C7114.4 (5)H35E—C35'—H35F109.5
C5—C6—H6A108.7C33'—C36'—H36D109.5
C7—C6—H6A108.7C33'—C36'—H36E109.5
C5—C6—H6B108.7H36D—C36'—H36E109.5
C7—C6—H6B108.7C33'—C36'—H36F109.5
H6A—C6—H6B107.6H36D—C36'—H36F109.5
C6—C7—H7A109.5H36E—C36'—H36F109.5
C6—C7—H7B109.5N6—C37—S7121.07 (16)
H7A—C7—H7B109.5N6—C37—S8121.64 (16)
C6—C7—H7C109.5S7—C37—S8117.26 (12)
H7A—C7—H7C109.5N6—C38—C39113.0 (2)
H7B—C7—H7C109.5N6—C38—H38A109.0
C5—C8—H8A109.5C39—C38—H38A109.0
C5—C8—H8B109.5N6—C38—H38B109.0
H8A—C8—H8B109.5C39—C38—H38B109.0
C5—C8—H8C109.5H38A—C38—H38B107.8
H8A—C8—H8C109.5C38—C39—C40109.7 (3)
H8B—C8—H8C109.5C38—C39—H39A109.7
N1—C5'—C6'111.4 (4)C40—C39—H39A109.7
N1—C5'—C8'120.0 (6)C38—C39—H39B109.7
C6'—C5'—C8'112.2 (5)C40—C39—H39B109.7
N1—C5'—H5'103.7H39A—C39—H39B108.2
C6'—C5'—H5'103.7C39—C40—H40A109.5
C8'—C5'—H5'103.7C39—C40—H40B109.5
C7'—C6'—C5'113.6 (5)H40A—C40—H40B109.5
C7'—C6'—H6'A108.8C39—C40—H40C109.5
C5'—C6'—H6'A108.8H40A—C40—H40C109.5
C7'—C6'—H6'B108.8H40B—C40—H40C109.5
C5'—C6'—H6'B108.8N6—C41—C42105.0 (3)
H6'A—C6'—H6'B107.7N6—C41—C44114.4 (6)
C6'—C7'—H7'A109.5C42—C41—C44113.3 (5)
C6'—C7'—H7'B109.5N6—C41—H41108.0
H7'A—C7'—H7'B109.5C42—C41—H41108.0
C6'—C7'—H7'C109.5C44—C41—H41108.0
H7'A—C7'—H7'C109.5C41—C42—C43116.1 (5)
H7'B—C7'—H7'C109.5C41—C42—H42A108.3
C5'—C8'—H8'A109.5C43—C42—H42A108.3
C5'—C8'—H8'B109.5C41—C42—H42B108.3
H8'A—C8'—H8'B109.5C43—C42—H42B108.3
C5'—C8'—H8'C109.5H42A—C42—H42B107.4
H8'A—C8'—H8'C109.5C42—C43—H43A109.5
H8'B—C8'—H8'C109.5C42—C43—H43B109.5
N2—C9—S4121.47 (16)H43A—C43—H43B109.5
N2—C9—S3121.44 (16)C42—C43—H43C109.5
S4—C9—S3117.08 (12)H43A—C43—H43C109.5
N2—C10—C11114.7 (2)H43B—C43—H43C109.5
N2—C10—H10A108.6C41—C44—H44A109.5
C11—C10—H10A108.6C41—C44—H44B109.5
N2—C10—H10B108.6H44A—C44—H44B109.5
C11—C10—H10B108.6C41—C44—H44C109.5
H10A—C10—H10B107.6H44A—C44—H44C109.5
C10—C11—C12110.7 (2)H44B—C44—H44C109.5
C10—C11—H11A109.5N6—C41'—C42'108.3 (4)
C12—C11—H11A109.5N6—C41'—C44'124.3 (7)
C10—C11—H11B109.5C42'—C41'—C44'111.4 (5)
C12—C11—H11B109.5N6—C41'—H41'103.5
H11A—C11—H11B108.1C42'—C41'—H41'103.5
C11—C12—H12A109.5C44'—C41'—H41'103.5
C11—C12—H12B109.5C43'—C42'—C41'113.4 (6)
H12A—C12—H12B109.5C43'—C42'—H42C108.9
C11—C12—H12C109.5C41'—C42'—H42C108.9
H12A—C12—H12C109.5C43'—C42'—H42D108.9
H12B—C12—H12C109.5C41'—C42'—H42D108.9
N2—C13—C14115.2 (3)H42C—C42'—H42D107.7
N2—C13—C16113.5 (3)C42'—C43'—H43D109.5
C14—C13—C16114.0 (3)C42'—C43'—H43E109.5
N2—C13—H13104.1H43D—C43'—H43E109.5
C14—C13—H13104.1C42'—C43'—H43F109.5
C16—C13—H13104.1H43D—C43'—H43F109.5
C13—C14—C15114.9 (4)H43E—C43'—H43F109.5
C13—C14—H14A108.5C41'—C44'—H44D109.5
C15—C14—H14A108.5C41'—C44'—H44E109.5
C13—C14—H14B108.5H44D—C44'—H44E109.5
C15—C14—H14B108.5C41'—C44'—H44F109.5
H14A—C14—H14B107.5H44D—C44'—H44F109.5
C14—C15—H15A109.5H44E—C44'—H44F109.5
C14—C15—H15B109.5N7—C45—C46122.9 (3)
H15A—C15—H15B109.5N7—C45—H45118.6
C14—C15—H15C109.5C46—C45—H45118.6
H15A—C15—H15C109.5C47—C46—C45119.7 (2)
H15B—C15—H15C109.5C47—C46—H46120.1
C13—C16—H16A109.5C45—C46—H46120.1
C13—C16—H16B109.5C46—C47—C48119.0 (2)
H16A—C16—H16B109.5C46—C47—H47120.5
C13—C16—H16C109.5C48—C47—H47120.5
H16A—C16—H16C109.5C49—C48—C47117.2 (2)
H16B—C16—H16C109.5C49—C48—C50119.6 (2)
N2—C13'—C14'113.2 (7)C47—C48—C50123.2 (2)
N2—C13'—C16'104.6 (12)N7—C49—C48123.3 (2)
C14'—C13'—C16'115.4 (8)N7—C49—C53117.43 (18)
N2—C13'—H13'107.8C48—C49—C53119.3 (2)
C14'—C13'—H13'107.8C51—C50—C48121.0 (2)
C16'—C13'—H13'107.8C51—C50—H50119.5
C15'—C14'—C13'118.0 (7)C48—C50—H50119.5
C15'—C14'—H14C107.8C50—C51—C52121.5 (2)
C13'—C14'—H14C107.8C50—C51—H51119.3
C15'—C14'—H14D107.8C52—C51—H51119.3
C13'—C14'—H14D107.8C54—C52—C53117.1 (2)
H14C—C14'—H14D107.2C54—C52—C51124.1 (2)
C14'—C15'—H15D109.5C53—C52—C51118.7 (2)
C14'—C15'—H15E109.5N8—C53—C52122.9 (2)
H15D—C15'—H15E109.5N8—C53—C49117.18 (19)
C14'—C15'—H15F109.5C52—C53—C49119.9 (2)
H15D—C15'—H15F109.5C55—C54—C52119.8 (2)
H15E—C15'—H15F109.5C55—C54—H54120.1
C13'—C16'—H16D109.5C52—C54—H54120.1
C13'—C16'—H16E109.5C54—C55—C56119.3 (2)
H16D—C16'—H16E109.5C54—C55—H55120.3
C13'—C16'—H16F109.5C56—C55—H55120.3
H16D—C16'—H16F109.5N8—C56—C55122.4 (2)
H16E—C16'—H16F109.5N8—C56—H56118.8
N3—C17—C18122.6 (2)C55—C56—H56118.8
N3—Zn1—S1—C192.65 (8)N2—C13'—C14'—C15'177.4 (12)
N4—Zn1—S1—C127.14 (12)C16'—C13'—C14'—C15'−62 (2)
S3—Zn1—S1—C1−102.80 (7)C21—N3—C17—C181.8 (3)
S4—Zn1—S1—C1−177.26 (7)Zn1—N3—C17—C18−174.46 (18)
S2—Zn1—S1—C1−0.12 (7)N3—C17—C18—C190.7 (4)
N3—Zn1—S2—C1−92.95 (8)C17—C18—C19—C20−2.4 (4)
N4—Zn1—S2—C1−166.99 (8)C18—C19—C20—C211.7 (3)
S3—Zn1—S2—C198.21 (7)C18—C19—C20—C22−179.7 (2)
S1—Zn1—S2—C10.12 (7)C17—N3—C21—C20−2.5 (3)
N3—Zn1—S3—C938.15 (14)Zn1—N3—C21—C20174.12 (16)
N4—Zn1—S3—C9103.67 (8)C17—N3—C21—C25179.38 (19)
S4—Zn1—S3—C92.60 (7)Zn1—N3—C21—C25−3.9 (2)
S1—Zn1—S3—C9−98.24 (7)C19—C20—C21—N30.8 (3)
S2—Zn1—S3—C9−171.94 (7)C22—C20—C21—N3−177.8 (2)
N3—Zn1—S4—C9−169.67 (9)C19—C20—C21—C25178.9 (2)
N4—Zn1—S4—C9−95.55 (9)C22—C20—C21—C250.2 (3)
S3—Zn1—S4—C9−2.61 (7)C19—C20—C22—C23−177.7 (2)
S1—Zn1—S4—C996.25 (8)C21—C20—C22—C230.9 (3)
N8—Zn2—S5—C29−101.08 (8)C20—C22—C23—C24−0.9 (3)
N7—Zn2—S5—C29−42.31 (14)C22—C23—C24—C26177.4 (2)
S6—Zn2—S5—C291.17 (7)C22—C23—C24—C25−0.2 (3)
S7—Zn2—S5—C2997.27 (7)C28—N4—C25—C24−2.7 (3)
S8—Zn2—S5—C29170.94 (7)Zn1—N4—C25—C24−171.81 (16)
N8—Zn2—S6—C2988.24 (9)C28—N4—C25—C21176.34 (18)
N7—Zn2—S6—C29162.16 (9)Zn1—N4—C25—C217.2 (2)
S7—Zn2—S6—C29−104.12 (7)C26—C24—C25—N42.5 (3)
S5—Zn2—S6—C29−1.17 (7)C23—C24—C25—N4−179.68 (19)
S8—Zn2—S6—C29−56.09 (13)C26—C24—C25—C21−176.47 (19)
N8—Zn2—S7—C37−40.10 (13)C23—C24—C25—C211.3 (3)
N7—Zn2—S7—C37−101.43 (9)N3—C21—C25—N4−2.2 (3)
S6—Zn2—S7—C37168.23 (8)C20—C21—C25—N4179.62 (19)
S5—Zn2—S7—C3794.29 (8)N3—C21—C25—C24176.82 (19)
S8—Zn2—S7—C37−2.15 (8)C20—C21—C25—C24−1.3 (3)
N8—Zn2—S8—C37166.44 (9)C25—C24—C26—C27−0.6 (3)
N7—Zn2—S8—C3792.78 (9)C23—C24—C26—C27−178.2 (2)
S6—Zn2—S8—C37−48.28 (13)C24—C26—C27—C28−1.1 (3)
S7—Zn2—S8—C372.15 (8)C25—N4—C28—C270.9 (3)
S5—Zn2—S8—C37−100.64 (8)Zn1—N4—C28—C27168.68 (16)
N4—Zn1—N3—C17−178.0 (2)C26—C27—C28—N41.0 (3)
S3—Zn1—N3—C17−108.4 (2)C33—N5—C29—S6169.0 (3)
S4—Zn1—N3—C17−74.75 (18)C30—N5—C29—S6−1.4 (3)
S1—Zn1—N3—C1729.15 (19)C33'—N5—C29—S6−179.3 (3)
S2—Zn1—N3—C17100.55 (18)C33—N5—C29—S5−11.2 (4)
N4—Zn1—N3—C215.67 (14)C30—N5—C29—S5178.36 (15)
S3—Zn1—N3—C2175.3 (2)C33'—N5—C29—S50.5 (4)
S4—Zn1—N3—C21108.89 (15)Zn2—S6—C29—N5−178.39 (18)
S1—Zn1—N3—C21−147.20 (14)Zn2—S6—C29—S51.81 (11)
S2—Zn1—N3—C21−75.81 (15)Zn2—S5—C29—N5178.41 (18)
N3—Zn1—N4—C28−174.97 (18)Zn2—S5—C29—S6−1.80 (11)
S3—Zn1—N4—C2826.34 (17)C29—N5—C30—C31−80.8 (3)
S4—Zn1—N4—C2899.49 (17)C33—N5—C30—C31108.0 (3)
S1—Zn1—N4—C28−104.76 (18)C33'—N5—C30—C3197.1 (4)
S2—Zn1—N4—C28−78.85 (17)N5—C30—C31—C32−179.3 (2)
N3—Zn1—N4—C25−6.84 (14)C29—N5—C33—C34−102.5 (5)
S3—Zn1—N4—C25−165.54 (13)C30—N5—C33—C3468.3 (5)
S4—Zn1—N4—C25−92.39 (14)C33'—N5—C33—C34−179 (3)
S1—Zn1—N4—C2563.36 (18)C29—N5—C33—C36132.6 (4)
S2—Zn1—N4—C2589.27 (14)C30—N5—C33—C36−56.6 (5)
N8—Zn2—N7—C45179.7 (2)C33'—N5—C33—C3656 (3)
S6—Zn2—N7—C4576.44 (19)N5—C33—C34—C35167.9 (6)
S7—Zn2—N7—C45−23.92 (19)C36—C33—C34—C35−67.9 (8)
S5—Zn2—N7—C45117.29 (19)C29—N5—C33'—C34'−110.0 (6)
S8—Zn2—N7—C45−95.86 (19)C33—N5—C33'—C34'0(3)
N8—Zn2—N7—C490.28 (14)C30—N5—C33'—C34'72.1 (6)
S6—Zn2—N7—C49−102.99 (14)C29—N5—C33'—C36'123.3 (6)
S7—Zn2—N7—C49156.65 (14)C33—N5—C33'—C36'−127 (3)
S5—Zn2—N7—C49−62.1 (2)C30—N5—C33'—C36'−54.6 (7)
S8—Zn2—N7—C4984.71 (14)N5—C33'—C34'—C35'63.2 (10)
N7—Zn2—N8—C56175.97 (18)C36'—C33'—C34'—C35'−167.9 (8)
S6—Zn2—N8—C56−97.99 (16)C41—N6—C37—S7164.3 (3)
S7—Zn2—N8—C56110.59 (17)C38—N6—C37—S7−2.0 (4)
S5—Zn2—N8—C56−25.76 (17)C41'—N6—C37—S7−165.0 (3)
S8—Zn2—N8—C5674.86 (17)C41—N6—C37—S8−13.9 (4)
N7—Zn2—N8—C530.78 (14)C38—N6—C37—S8179.8 (2)
S6—Zn2—N8—C5386.82 (14)C41'—N6—C37—S816.7 (4)
S7—Zn2—N8—C53−64.60 (19)Zn2—S7—C37—N6−174.9 (2)
S5—Zn2—N8—C53159.05 (13)Zn2—S7—C37—S83.36 (12)
S8—Zn2—N8—C53−100.33 (14)Zn2—S8—C37—N6174.9 (2)
C2—N1—C1—S11.0 (3)Zn2—S8—C37—S7−3.34 (12)
C5—N1—C1—S1−166.3 (3)C37—N6—C38—C39−82.8 (3)
C5'—N1—C1—S1167.0 (3)C41—N6—C38—C39109.7 (3)
C2—N1—C1—S2179.54 (16)C41'—N6—C38—C3979.6 (4)
C5—N1—C1—S212.3 (4)N6—C38—C39—C40176.0 (3)
C5'—N1—C1—S2−14.5 (4)C37—N6—C41—C42121.0 (4)
Zn1—S1—C1—N1178.84 (18)C38—N6—C41—C42−72.0 (4)
Zn1—S1—C1—S20.19 (11)C41'—N6—C41—C4237.9 (8)
Zn1—S2—C1—N1−178.83 (18)C37—N6—C41—C44−114.2 (5)
Zn1—S2—C1—S1−0.19 (11)C38—N6—C41—C4452.8 (6)
C1—N1—C2—C381.1 (3)C41'—N6—C41—C44162.6 (13)
C5—N1—C2—C3−111.3 (3)N6—C41—C42—C43−55.0 (7)
C5'—N1—C2—C3−85.6 (3)C44—C41—C42—C43179.5 (8)
N1—C2—C3—C4−173.8 (2)C37—N6—C41'—C42'−148.7 (4)
C1—N1—C5—C8108.7 (6)C41—N6—C41'—C42'−36.1 (7)
C2—N1—C5—C8−58.9 (6)C38—N6—C41'—C42'48.3 (6)
C5'—N1—C5—C8−152.3 (17)C37—N6—C41'—C44'77.5 (9)
C1—N1—C5—C6−125.7 (4)C41—N6—C41'—C44'−169.8 (15)
C2—N1—C5—C666.7 (5)C38—N6—C41'—C44'−85.4 (8)
C5'—N1—C5—C6−26.7 (11)N6—C41'—C42'—C43'55.8 (10)
N1—C5—C6—C762.5 (8)C44'—C41'—C42'—C43'−164.2 (11)
C8—C5—C6—C7−171.1 (8)C49—N7—C45—C46−0.2 (3)
C1—N1—C5'—C6'132.0 (5)Zn2—N7—C45—C46−179.59 (19)
C2—N1—C5'—C6'−61.6 (6)N7—C45—C46—C47−0.4 (4)
C5—N1—C5'—C6'36.9 (11)C45—C46—C47—C480.7 (4)
C1—N1—C5'—C8'−94.0 (8)C46—C47—C48—C49−0.6 (3)
C2—N1—C5'—C8'72.4 (8)C46—C47—C48—C50−178.8 (2)
C5—N1—C5'—C8'170.9 (19)C45—N7—C49—C480.3 (3)
N1—C5'—C6'—C7'−43.3 (10)Zn2—N7—C49—C48179.80 (16)
C8'—C5'—C6'—C7'179.0 (10)C45—N7—C49—C53179.3 (2)
C10—N2—C9—S4−5.1 (3)Zn2—N7—C49—C53−1.3 (2)
C13—N2—C9—S4−176.3 (2)C47—C48—C49—N70.1 (3)
C13'—N2—C9—S4171.9 (5)C50—C48—C49—N7178.4 (2)
C10—N2—C9—S3173.76 (16)C47—C48—C49—C53−178.9 (2)
C13—N2—C9—S32.6 (3)C50—C48—C49—C53−0.6 (3)
C13'—N2—C9—S3−9.2 (6)C49—C48—C50—C51−0.8 (3)
Zn1—S4—C9—N2−177.02 (18)C47—C48—C50—C51177.4 (2)
Zn1—S4—C9—S34.03 (11)C48—C50—C51—C520.7 (4)
Zn1—S3—C9—N2177.02 (18)C50—C51—C52—C54−178.1 (2)
Zn1—S3—C9—S4−4.03 (11)C50—C51—C52—C530.6 (3)
C9—N2—C10—C1183.3 (3)C56—N8—C53—C521.8 (3)
C13—N2—C10—C11−105.2 (3)Zn2—N8—C53—C52177.33 (16)
C13'—N2—C10—C11−93.9 (6)C56—N8—C53—C49−177.27 (18)
N2—C10—C11—C12−176.9 (2)Zn2—N8—C53—C49−1.7 (2)
C9—N2—C13—C1483.7 (4)C54—C52—C53—N8−2.1 (3)
C10—N2—C13—C14−87.7 (4)C51—C52—C53—N8179.05 (19)
C13'—N2—C13—C14170 (4)C54—C52—C53—C49176.87 (19)
C9—N2—C13—C16−142.2 (3)C51—C52—C53—C49−1.9 (3)
C10—N2—C13—C1646.4 (4)N7—C49—C53—N82.0 (3)
C13'—N2—C13—C16−56 (3)C48—C49—C53—N8−179.02 (19)
N2—C13—C14—C1568.7 (5)N7—C49—C53—C52−177.07 (19)
C16—C13—C14—C15−65.1 (5)C48—C49—C53—C521.9 (3)
C9—N2—C13'—C14'−130.7 (9)C53—C52—C54—C550.6 (3)
C10—N2—C13'—C14'46.4 (12)C51—C52—C54—C55179.3 (2)
C13—N2—C13'—C14'130 (4)C52—C54—C55—C561.3 (3)
C9—N2—C13'—C16'102.9 (10)C53—N8—C56—C550.2 (3)
C10—N2—C13'—C16'−80.0 (11)Zn2—N8—C56—C55−174.88 (16)
C13—N2—C13'—C16'3(3)C54—C55—C56—N8−1.7 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C28—H28a···S8i0.952.803.560 (2)137
C50—H50···S8ii0.952.803.702 (3)158

Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5329).

References

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