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Acta Cryst. (2009). E65, m471    [ doi:10.1107/S1600536809011155 ]

Bis([mu]-N-benzyl-N-tetradecyldithiocarbamato-[kappa]2S:S')bis[(N-benzyl-N-tetradecyldithiocarbamato-[kappa]2S,S')zinc(II)]

C.-M. Jia, W.-B. Yuan, Q. Lin, Q. Zhang and J. Pei

Abstract top

In the title compound, [Zn2(C22H36NS2)4], two bidentate dithiocarbamate groups chelate directly to the ZnII atoms, whereas the two remaining dithiocarbamate ligands bridge the Zn atoms via a crystallographic inversion centre. The Zn atoms show a strongly distorted tetrahedral geometry. Adding the long S...S distance with the inversion centre being in the middle, the resulting five-coordinate geometry around the Zn atoms can be considered to be between distorted rectangular pyramidal and trigonal bipyramidal, with a calculated [tau] value of 0.31. In this dimer complex, two inversion-related tetradecyl carbon chains exhibit all-trans conformations, and the other two chains show a cis conformation at the end of the chains.

Comment top

Some crystal structures of centrosymmetric dimeric zincII–dithiocarbamate complexes have been reported, and this family compounds involve the similar ligands such as ethylisopropyldithiocarbamate (Baba, Farina, Othman et al., 2001), ethylbutyldithiocarbamate (Baba, Farina, Kassim et al., 2001) and piperidine-1-dithiocarbamate (Shaheen et al.,2006).

In the title complex (I), representing another member of dimeric dithiocarbamate complexes, two inversion related tetradecyl carbon chains exhibit all trans-conformations, and the other two chains show a cis-conformation at the end of the chains. The Zn–S bond lengths are within the sum of the covalent radii of 2.47 Å (S = 1.02 Å, Zn = 1.45 Å) (Table 1), and they agree with the values found in the literatures (Baba, Farina, Othman et al., 2001; 2001b; Shaheen et al., 2006). However, two of the six tetrahedral angles [S2–Zn1–S1=75.71°(2) and S4–Zn1–S2=136.18°(2)] differ greatly from the ideal value, 109.5°. Consequently, the longer distance of 2.8879 (6) Å for Zn1–S3A may be considered, which expands the view of a strongly distorted tetrahedral ZnS4 evironment: if the symmetry related atom S3A (symmetry code: 2-x, -y, 1-z) is added to the Zn environment, a rectangular pyramidal or a trigonal bipyramidal geometry can be calculated by using the formula τ = (β - α)/60, which is applicable to five-co-ordinate structures within the structural continuum between trigonal bipyramidal and rectangular pyramidal (Addison et al., 1984). In this structure, the "rectangular" unit consists of S1, S2 S4, S3A, and S3 is considered as the axial atom. The largest angles within the four atoms S1-S3A are β = 154.92 (2)° for S1–Zn1–S3A and α = 136.18 (2)° for S2–Zn1–S4. As a result, τ is (154.92-136.18)/60 = 0.31, indicating a 69% rectangular pyramidal geometry.

Related literature top

For related centrosymmetric dimeric ZnII structures, see: Baba, Farina, Othman et al. (2001); Baba, Farina, Kassim et al. (2001); Shaheen et al. (2006). For an analysis of five-coordinate crystal structures, see: Addison et al. (1984).

Experimental top

White crystals of (I) were obtained by slow evaporation of a solution in dichloromethane (10 ml) of benzyl(tetradecyl)carbamatodithioic acid (0.076 g, 0.2 mmol) and Zn(OAc)2 (0.022 g, 0.1 mmol).

Refinement top

H atoms were positioned geometrically (C–H = 0.95–0.99 Å) and allowed to ride on their parent atoms with Uiso(H) = 1.2 Ueq(C).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. A perspective view of the dimer complex of (I). Displacement ellipsoids are drawn at the 50% probability level. Symmetry code for the atoms labelled with an A: (2 - x, -y, 1 - z).
Bis(µ-N-benzyl-N-tetradecyldithiocarbamato- κ2S:S')bis[(N-benzyl-N- tetradecyldithiocarbamato-κ2S,S')zinc(II)] top
Crystal data top
[Zn2(C22H36NS2)4]Z = 1
Mr = 1645.29F(000) = 888
Triclinic, P1Dx = 1.215 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 11.007 (1) ÅCell parameters from 6628 reflections
b = 11.640 (1) Åθ = 3.0–27.5°
c = 18.818 (2) ŵ = 0.76 mm−1
α = 85.645 (4)°T = 153 K
β = 76.913 (4)°Claviform, white
γ = 73.263 (4)°0.43 × 0.10 × 0.10 mm
V = 2248.7 (4) Å3
Data collection top
Rigaku SPIDER
diffractometer		7979 independent reflections
Radiation source: Rotating Anode7057 reflections with I > 2σ(I)
graphiteRint = 0.024
Detector resolution: 28.5714 pixels mm-1θmax = 25.3°, θmin = 3.0°
ω scansh = −13→13
Absorption correction: empirical (using intensity measurements)
(ABSCOR; Higashi, 1995)		k = −13→13
Tmin = 0.734, Tmax = 0.928l = −22→22
15746 measured reflections
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)] = 0.037Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0466P)2 + 0.22P]
where P = (Fo2 + 2Fc2)/3
7979 reflections(Δ/σ)max = 0.001
462 parametersΔρmax = 0.37 e Å−3
0 restraintsΔρmin = −0.25 e Å−3
Crystal data top
[Zn2(C22H36NS2)4]γ = 73.263 (4)°
Mr = 1645.29V = 2248.7 (4) Å3
Triclinic, P1Z = 1
a = 11.007 (1) ÅMo Kα radiation
b = 11.640 (1) ŵ = 0.76 mm−1
c = 18.818 (2) ÅT = 153 K
α = 85.645 (4)°0.43 × 0.10 × 0.10 mm
β = 76.913 (4)°
Data collection top
Rigaku SPIDER
diffractometer		7979 independent reflections
Absorption correction: empirical (using intensity measurements)
(ABSCOR; Higashi, 1995)		7057 reflections with I > 2σ(I)
Tmin = 0.734, Tmax = 0.928Rint = 0.024
15746 measured reflectionsθmax = 25.3°
Refinement top
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.087Δρmax = 0.37 e Å−3
S = 1.01Δρmin = −0.25 e Å−3
7979 reflectionsAbsolute structure: ?
462 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
Zn10.83591 (2)0.04989 (2)0.478389 (13)0.02398 (8)
S10.62087 (5)0.16828 (5)0.46274 (3)0.02492 (13)
S20.69528 (5)0.01501 (5)0.58593 (3)0.02590 (13)
S30.97178 (5)0.16703 (4)0.49421 (3)0.02298 (12)
S40.94700 (5)−0.05478 (5)0.37081 (3)0.02584 (13)
N10.44801 (16)0.12946 (15)0.58110 (9)0.0223 (4)
N20.83787 (15)0.23154 (14)0.63025 (9)0.0220 (4)
C10.57256 (19)0.10751 (17)0.54731 (11)0.0219 (4)
C20.3428 (2)0.20710 (19)0.54799 (12)0.0272 (5)
H2A0.26910.17140.55800.033*
H2B0.37460.20890.49440.033*
C30.29449 (19)0.33458 (19)0.57567 (11)0.0263 (5)
C40.1671 (2)0.3788 (2)0.61380 (13)0.0347 (5)
H40.11050.32870.62230.042*
C50.1217 (2)0.4952 (2)0.63952 (14)0.0421 (6)
H50.03470.52400.66600.050*
C60.2020 (2)0.5698 (2)0.62687 (14)0.0404 (6)
H60.17050.64990.64400.049*
C70.3282 (2)0.5264 (2)0.58913 (13)0.0369 (6)
H70.38440.57690.58060.044*
C80.3742 (2)0.4103 (2)0.56352 (12)0.0300 (5)
H80.46150.38200.53730.036*
C90.4060 (2)0.06529 (19)0.64844 (11)0.0266 (5)
H9A0.48360.00710.66110.032*
H9B0.34900.01900.63860.032*
C100.3337 (2)0.1449 (2)0.71421 (11)0.0278 (5)
H10A0.25030.19590.70400.033*
H10B0.31320.09310.75680.033*
C110.4075 (2)0.22489 (19)0.73399 (11)0.0279 (5)
H11A0.42420.27980.69250.033*
H11B0.49260.17450.74220.033*
C120.3352 (2)0.2987 (2)0.80179 (12)0.0332 (5)
H12A0.24680.34280.79550.040*
H12B0.32620.24370.84420.040*
C130.4018 (2)0.3877 (2)0.81796 (12)0.0340 (5)
H13A0.49160.34350.82180.041*
H13B0.40780.44410.77600.041*
C140.3365 (2)0.4600 (2)0.88661 (12)0.0342 (5)
H14A0.33180.40430.92890.041*
H14B0.24650.50420.88330.041*
C150.4060 (2)0.5490 (2)0.89997 (12)0.0341 (5)
H15A0.41120.60420.85740.041*
H15B0.49590.50460.90340.041*
C160.3417 (2)0.6231 (2)0.96837 (13)0.0341 (5)
H16A0.25110.66610.96560.041*
H16B0.33870.56821.01120.041*
C170.4102 (2)0.7137 (2)0.97988 (12)0.0340 (5)
H17A0.41080.77000.93770.041*
H17B0.50160.67090.98100.041*
C180.3486 (2)0.7857 (2)1.04965 (12)0.0336 (5)
H18A0.25670.82741.04900.040*
H18B0.34950.72961.09190.040*
C190.4158 (2)0.8777 (2)1.06021 (12)0.0326 (5)
H19A0.41350.93461.01830.039*
H19B0.50810.83621.05990.039*
C200.3563 (2)0.9484 (2)1.13037 (12)0.0315 (5)
H20A0.26400.98991.13070.038*
H20B0.35880.89161.17230.038*
C210.4238 (2)1.0405 (2)1.14052 (13)0.0410 (6)
H21A0.42301.09641.09810.049*
H21B0.51570.99891.14130.049*
C220.3622 (3)1.1126 (2)1.20980 (14)0.0517 (7)
H22A0.27121.15431.20950.062*
H22B0.40911.17151.21240.062*
H22C0.36641.05851.25230.062*
C230.94184 (19)0.15950 (17)0.58946 (11)0.0211 (4)
C240.73607 (19)0.31852 (18)0.59877 (12)0.0262 (5)
H24A0.65080.30520.62150.031*
H24B0.75290.30360.54590.031*
C250.72970 (19)0.44683 (18)0.60955 (11)0.0221 (4)
C260.6207 (2)0.5230 (2)0.65140 (12)0.0317 (5)
H260.54830.49440.67370.038*
C270.6166 (2)0.6411 (2)0.66099 (14)0.0427 (6)
H270.54160.69280.69010.051*
C280.7200 (3)0.6833 (2)0.62873 (14)0.0430 (6)
H280.71720.76420.63560.052*
C290.8279 (2)0.6086 (2)0.58637 (13)0.0391 (6)
H290.89950.63810.56350.047*
C300.8329 (2)0.4914 (2)0.57690 (12)0.0307 (5)
H300.90810.44030.54760.037*
C310.8067 (2)0.2133 (2)0.71060 (11)0.0277 (5)
H31A0.82200.12620.72060.033*
H31B0.71290.25170.72860.033*
C320.8813 (2)0.2607 (2)0.75521 (12)0.0300 (5)
H32A0.88320.21310.80100.036*
H32B0.97210.24640.72750.036*
C330.8288 (2)0.39255 (19)0.77481 (12)0.0282 (5)
H33A0.73430.41100.79560.034*
H33B0.84150.44180.72990.034*
C340.8954 (2)0.4262 (2)0.82971 (12)0.0307 (5)
H34A0.88680.37330.87320.037*
H34B0.98910.41100.80770.037*
C350.8410 (2)0.5560 (2)0.85387 (12)0.0329 (5)
H35A0.74620.57280.87310.040*
H35B0.85470.60900.81090.040*
C360.9027 (2)0.5862 (2)0.91201 (13)0.0339 (5)
H36A0.99700.57230.89190.041*
H36B0.89230.53070.95400.041*
C370.8459 (2)0.7147 (2)0.93915 (13)0.0323 (5)
H37A0.85830.77020.89740.039*
H37B0.75130.72920.95820.039*
C380.9059 (2)0.7432 (2)0.99842 (12)0.0318 (5)
H38A1.00050.72850.97930.038*
H38B0.89350.68761.04020.038*
C390.8494 (2)0.8716 (2)1.02573 (12)0.0308 (5)
H39A0.86100.92730.98390.037*
H39B0.75500.88611.04530.037*
C400.9106 (2)0.8998 (2)1.08433 (12)0.0314 (5)
H40A1.00510.88511.06470.038*
H40B0.89900.84411.12610.038*
C410.8545 (2)1.0287 (2)1.11195 (12)0.0323 (5)
H41A0.86421.08481.07020.039*
H41B0.76051.04301.13310.039*
C420.9204 (2)1.0552 (2)1.16927 (13)0.0391 (6)
H42A1.01461.03891.14810.047*
H42B0.90980.99911.21090.047*
C430.8696 (3)1.1830 (2)1.19806 (14)0.0480 (7)
H43A0.92981.19671.22630.058*
H43B0.86811.24011.15630.058*
C440.7356 (3)1.2077 (3)1.24580 (16)0.0590 (8)
H44A0.67531.19521.21790.071*
H44B0.70691.29091.26250.071*
H44C0.73701.15321.28810.071*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.02638 (15)0.02349 (14)0.02330 (14)−0.00954 (11)−0.00226 (10)−0.00692 (10)
S10.0280 (3)0.0263 (3)0.0206 (3)−0.0076 (2)−0.0048 (2)−0.0019 (2)
S20.0276 (3)0.0223 (3)0.0270 (3)−0.0070 (2)−0.0050 (2)0.0018 (2)
S30.0277 (3)0.0216 (3)0.0215 (3)−0.0105 (2)−0.0037 (2)−0.0017 (2)
S40.0300 (3)0.0246 (3)0.0215 (3)−0.0030 (2)−0.0067 (2)−0.0061 (2)
N10.0254 (9)0.0223 (9)0.0216 (9)−0.0097 (7)−0.0050 (7)−0.0034 (7)
N20.0228 (9)0.0213 (9)0.0235 (9)−0.0085 (7)−0.0034 (7)−0.0062 (7)
C10.0287 (11)0.0158 (10)0.0230 (11)−0.0073 (9)−0.0054 (9)−0.0080 (8)
C20.0242 (11)0.0310 (12)0.0303 (12)−0.0114 (10)−0.0079 (9)−0.0034 (9)
C30.0254 (11)0.0305 (12)0.0247 (11)−0.0082 (10)−0.0093 (9)0.0020 (9)
C40.0266 (12)0.0379 (14)0.0404 (14)−0.0101 (11)−0.0070 (10)−0.0013 (11)
C50.0271 (13)0.0409 (15)0.0493 (16)0.0004 (11)−0.0007 (11)−0.0074 (12)
C60.0434 (15)0.0258 (13)0.0491 (16)−0.0016 (11)−0.0130 (12)−0.0045 (11)
C70.0403 (14)0.0267 (13)0.0466 (15)−0.0129 (11)−0.0120 (12)0.0043 (11)
C80.0261 (12)0.0307 (13)0.0323 (12)−0.0081 (10)−0.0052 (10)0.0021 (10)
C90.0289 (12)0.0267 (12)0.0267 (11)−0.0141 (10)−0.0015 (9)−0.0030 (9)
C100.0292 (12)0.0316 (12)0.0236 (11)−0.0120 (10)−0.0028 (9)−0.0021 (9)
C110.0302 (12)0.0316 (12)0.0244 (11)−0.0129 (10)−0.0045 (9)−0.0029 (9)
C120.0352 (13)0.0404 (14)0.0280 (12)−0.0168 (11)−0.0043 (10)−0.0075 (10)
C130.0410 (13)0.0371 (13)0.0286 (12)−0.0187 (11)−0.0053 (10)−0.0046 (10)
C140.0352 (13)0.0374 (14)0.0329 (13)−0.0143 (11)−0.0050 (10)−0.0088 (10)
C150.0401 (13)0.0346 (13)0.0311 (12)−0.0162 (11)−0.0055 (10)−0.0068 (10)
C160.0342 (13)0.0349 (13)0.0349 (13)−0.0101 (11)−0.0078 (10)−0.0082 (10)
C170.0400 (13)0.0344 (13)0.0316 (13)−0.0147 (11)−0.0078 (10)−0.0065 (10)
C180.0338 (13)0.0341 (13)0.0344 (13)−0.0111 (11)−0.0057 (10)−0.0068 (10)
C190.0365 (13)0.0328 (13)0.0294 (12)−0.0127 (11)−0.0037 (10)−0.0050 (10)
C200.0371 (13)0.0309 (13)0.0277 (12)−0.0099 (10)−0.0075 (10)−0.0035 (10)
C210.0569 (16)0.0363 (14)0.0337 (13)−0.0178 (12)−0.0089 (12)−0.0069 (11)
C220.081 (2)0.0381 (15)0.0388 (15)−0.0133 (14)−0.0196 (14)−0.0083 (12)
C230.0257 (11)0.0207 (10)0.0218 (10)−0.0142 (9)−0.0037 (9)−0.0037 (8)
C240.0210 (11)0.0259 (12)0.0325 (12)−0.0051 (9)−0.0066 (9)−0.0079 (9)
C250.0257 (11)0.0213 (11)0.0200 (10)−0.0048 (9)−0.0077 (9)−0.0024 (8)
C260.0271 (12)0.0306 (13)0.0343 (13)−0.0045 (10)−0.0033 (10)−0.0058 (10)
C270.0452 (15)0.0300 (13)0.0455 (15)0.0058 (12)−0.0110 (12)−0.0146 (11)
C280.0699 (18)0.0204 (12)0.0445 (15)−0.0114 (13)−0.0259 (14)0.0016 (11)
C290.0547 (16)0.0349 (14)0.0349 (14)−0.0250 (13)−0.0107 (12)0.0084 (11)
C300.0348 (13)0.0302 (12)0.0268 (12)−0.0122 (10)−0.0013 (10)−0.0022 (9)
C310.0279 (12)0.0294 (12)0.0242 (11)−0.0099 (10)0.0018 (9)−0.0051 (9)
C320.0307 (12)0.0330 (13)0.0252 (11)−0.0063 (10)−0.0042 (9)−0.0093 (9)
C330.0317 (12)0.0287 (12)0.0257 (11)−0.0091 (10)−0.0069 (9)−0.0045 (9)
C340.0355 (13)0.0311 (13)0.0264 (12)−0.0074 (10)−0.0089 (10)−0.0062 (9)
C350.0378 (13)0.0321 (13)0.0304 (12)−0.0076 (11)−0.0115 (10)−0.0050 (10)
C360.0365 (13)0.0330 (13)0.0340 (13)−0.0081 (11)−0.0105 (10)−0.0099 (10)
C370.0352 (13)0.0309 (13)0.0331 (13)−0.0090 (10)−0.0111 (10)−0.0045 (10)
C380.0351 (13)0.0320 (13)0.0308 (12)−0.0099 (10)−0.0091 (10)−0.0068 (10)
C390.0358 (13)0.0304 (12)0.0278 (12)−0.0103 (10)−0.0078 (10)−0.0030 (10)
C400.0343 (13)0.0334 (13)0.0277 (12)−0.0099 (10)−0.0064 (10)−0.0059 (10)
C410.0392 (13)0.0307 (13)0.0279 (12)−0.0114 (11)−0.0061 (10)−0.0025 (10)
C420.0410 (14)0.0441 (15)0.0349 (14)−0.0134 (12)−0.0074 (11)−0.0130 (11)
C430.0604 (17)0.0489 (16)0.0404 (15)−0.0254 (14)−0.0051 (13)−0.0131 (12)
C440.0670 (19)0.0537 (18)0.0540 (18)−0.0136 (16)−0.0067 (15)−0.0190 (15)
Geometric parameters (Å, °) top
Zn1—S42.3396 (6)C20—H20B0.9900
Zn1—S22.3398 (6)C21—C221.517 (3)
Zn1—S32.3711 (6)C21—H21A0.9900
Zn1—S12.4420 (6)C21—H21B0.9900
Zn1—S3i2.8879 (6)C22—H22A0.9800
S1—C11.726 (2)C22—H22B0.9800
S2—C11.732 (2)C22—H22C0.9800
S3—C231.748 (2)C23—S4i1.720 (2)
S4—C23i1.720 (2)C24—C251.502 (3)
N1—C11.333 (3)C24—H24A0.9900
N1—C91.472 (3)C24—H24B0.9900
N1—C21.478 (3)C25—C301.383 (3)
N2—C231.323 (2)C25—C261.383 (3)
N2—C241.479 (3)C26—C271.386 (3)
N2—C311.486 (3)C26—H260.9500
C2—C31.514 (3)C27—C281.368 (4)
C2—H2A0.9900C27—H270.9500
C2—H2B0.9900C28—C291.373 (3)
C3—C81.387 (3)C28—H280.9500
C3—C41.390 (3)C29—C301.373 (3)
C4—C51.386 (3)C29—H290.9500
C4—H40.9500C30—H300.9500
C5—C61.381 (3)C31—C321.525 (3)
C5—H50.9500C31—H31A0.9900
C6—C71.376 (3)C31—H31B0.9900
C6—H60.9500C32—C331.518 (3)
C7—C81.382 (3)C32—H32A0.9900
C7—H70.9500C32—H32B0.9900
C8—H80.9500C33—C341.525 (3)
C9—C101.525 (3)C33—H33A0.9900
C9—H9A0.9900C33—H33B0.9900
C9—H9B0.9900C34—C351.520 (3)
C10—C111.514 (3)C34—H34A0.9900
C10—H10A0.9900C34—H34B0.9900
C10—H10B0.9900C35—C361.522 (3)
C11—C121.521 (3)C35—H35A0.9900
C11—H11A0.9900C35—H35B0.9900
C11—H11B0.9900C36—C371.523 (3)
C12—C131.513 (3)C36—H36A0.9900
C12—H12A0.9900C36—H36B0.9900
C12—H12B0.9900C37—C381.519 (3)
C13—C141.513 (3)C37—H37A0.9900
C13—H13A0.9900C37—H37B0.9900
C13—H13B0.9900C38—C391.523 (3)
C14—C151.518 (3)C38—H38A0.9900
C14—H14A0.9900C38—H38B0.9900
C14—H14B0.9900C39—C401.516 (3)
C15—C161.518 (3)C39—H39A0.9900
C15—H15A0.9900C39—H39B0.9900
C15—H15B0.9900C40—C411.530 (3)
C16—C171.515 (3)C40—H40A0.9900
C16—H16A0.9900C40—H40B0.9900
C16—H16B0.9900C41—C421.523 (3)
C17—C181.524 (3)C41—H41A0.9900
C17—H17A0.9900C41—H41B0.9900
C17—H17B0.9900C42—C431.525 (3)
C18—C191.512 (3)C42—H42A0.9900
C18—H18A0.9900C42—H42B0.9900
C18—H18B0.9900C43—C441.504 (4)
C19—C201.521 (3)C43—H43A0.9900
C19—H19A0.9900C43—H43B0.9900
C19—H19B0.9900C44—H44A0.9800
C20—C211.514 (3)C44—H44B0.9800
C20—H20A0.9900C44—H44C0.9800
S4—Zn1—S2136.18 (2)C21—C22—H22A109.5
S4—Zn1—S3103.77 (2)C21—C22—H22B109.5
S2—Zn1—S3114.12 (2)H22A—C22—H22B109.5
S4—Zn1—S1108.81 (2)C21—C22—H22C109.5
S2—Zn1—S175.71 (2)H22A—C22—H22C109.5
S3—Zn1—S1113.87 (2)H22B—C22—H22C109.5
S1—Zn1—S3i154.92 (2)N2—C23—S4i120.54 (15)
C1—S1—Zn182.52 (7)N2—C23—S3121.74 (16)
C1—S2—Zn185.54 (7)S4i—C23—S3117.72 (11)
C23—S3—Zn197.24 (6)N2—C24—C25113.18 (17)
C23i—S4—Zn195.32 (7)N2—C24—H24A108.9
C1—N1—C9121.94 (17)C25—C24—H24A108.9
C1—N1—C2121.80 (17)N2—C24—H24B108.9
C9—N1—C2115.75 (16)C25—C24—H24B108.9
C23—N2—C24122.55 (17)H24A—C24—H24B107.8
C23—N2—C31120.41 (17)C30—C25—C26118.7 (2)
C24—N2—C31116.19 (16)C30—C25—C24120.33 (18)
N1—C1—S1122.21 (16)C26—C25—C24121.01 (18)
N1—C1—S2121.59 (16)C25—C26—C27120.3 (2)
S1—C1—S2116.20 (11)C25—C26—H26119.9
N1—C2—C3113.80 (17)C27—C26—H26119.9
N1—C2—H2A108.8C28—C27—C26120.3 (2)
C3—C2—H2A108.8C28—C27—H27119.9
N1—C2—H2B108.8C26—C27—H27119.9
C3—C2—H2B108.8C27—C28—C29119.8 (2)
H2A—C2—H2B107.7C27—C28—H28120.1
C8—C3—C4118.3 (2)C29—C28—H28120.1
C8—C3—C2121.65 (18)C28—C29—C30120.3 (2)
C4—C3—C2120.08 (19)C28—C29—H29119.9
C5—C4—C3120.7 (2)C30—C29—H29119.9
C5—C4—H4119.7C29—C30—C25120.8 (2)
C3—C4—H4119.7C29—C30—H30119.6
C6—C5—C4120.5 (2)C25—C30—H30119.6
C6—C5—H5119.8N2—C31—C32117.10 (17)
C4—C5—H5119.8N2—C31—H31A108.0
C7—C6—C5119.1 (2)C32—C31—H31A108.0
C7—C6—H6120.5N2—C31—H31B108.0
C5—C6—H6120.5C32—C31—H31B108.0
C6—C7—C8120.7 (2)H31A—C31—H31B107.3
C6—C7—H7119.6C33—C32—C31116.30 (18)
C8—C7—H7119.6C33—C32—H32A108.2
C7—C8—C3120.8 (2)C31—C32—H32A108.2
C7—C8—H8119.6C33—C32—H32B108.2
C3—C8—H8119.6C31—C32—H32B108.2
N1—C9—C10115.12 (17)H32A—C32—H32B107.4
N1—C9—H9A108.5C32—C33—C34112.19 (18)
C10—C9—H9A108.5C32—C33—H33A109.2
N1—C9—H9B108.5C34—C33—H33A109.2
C10—C9—H9B108.5C32—C33—H33B109.2
H9A—C9—H9B107.5C34—C33—H33B109.2
C11—C10—C9114.41 (17)H33A—C33—H33B107.9
C11—C10—H10A108.7C35—C34—C33113.98 (18)
C9—C10—H10A108.7C35—C34—H34A108.8
C11—C10—H10B108.7C33—C34—H34A108.8
C9—C10—H10B108.7C35—C34—H34B108.8
H10A—C10—H10B107.6C33—C34—H34B108.8
C10—C11—C12112.98 (17)H34A—C34—H34B107.7
C10—C11—H11A109.0C34—C35—C36113.37 (19)
C12—C11—H11A109.0C34—C35—H35A108.9
C10—C11—H11B109.0C36—C35—H35A108.9
C12—C11—H11B109.0C34—C35—H35B108.9
H11A—C11—H11B107.8C36—C35—H35B108.9
C13—C12—C11113.47 (18)H35A—C35—H35B107.7
C13—C12—H12A108.9C35—C36—C37114.20 (19)
C11—C12—H12A108.9C35—C36—H36A108.7
C13—C12—H12B108.9C37—C36—H36A108.7
C11—C12—H12B108.9C35—C36—H36B108.7
H12A—C12—H12B107.7C37—C36—H36B108.7
C14—C13—C12115.53 (18)H36A—C36—H36B107.6
C14—C13—H13A108.4C38—C37—C36113.87 (19)
C12—C13—H13A108.4C38—C37—H37A108.8
C14—C13—H13B108.4C36—C37—H37A108.8
C12—C13—H13B108.4C38—C37—H37B108.8
H13A—C13—H13B107.5C36—C37—H37B108.8
C13—C14—C15113.56 (18)H37A—C37—H37B107.7
C13—C14—H14A108.9C37—C38—C39114.07 (19)
C15—C14—H14A108.9C37—C38—H38A108.7
C13—C14—H14B108.9C39—C38—H38A108.7
C15—C14—H14B108.9C37—C38—H38B108.7
H14A—C14—H14B107.7C39—C38—H38B108.7
C14—C15—C16114.49 (18)H38A—C38—H38B107.6
C14—C15—H15A108.6C40—C39—C38113.79 (19)
C16—C15—H15A108.6C40—C39—H39A108.8
C14—C15—H15B108.6C38—C39—H39A108.8
C16—C15—H15B108.6C40—C39—H39B108.8
H15A—C15—H15B107.6C38—C39—H39B108.8
C17—C16—C15113.85 (18)H39A—C39—H39B107.7
C17—C16—H16A108.8C39—C40—C41114.09 (19)
C15—C16—H16A108.8C39—C40—H40A108.7
C17—C16—H16B108.8C41—C40—H40A108.7
C15—C16—H16B108.8C39—C40—H40B108.7
H16A—C16—H16B107.7C41—C40—H40B108.7
C16—C17—C18114.13 (19)H40A—C40—H40B107.6
C16—C17—H17A108.7C42—C41—C40112.82 (19)
C18—C17—H17A108.7C42—C41—H41A109.0
C16—C17—H17B108.7C40—C41—H41A109.0
C18—C17—H17B108.7C42—C41—H41B109.0
H17A—C17—H17B107.6C40—C41—H41B109.0
C19—C18—C17113.93 (18)H41A—C41—H41B107.8
C19—C18—H18A108.8C41—C42—C43115.1 (2)
C17—C18—H18A108.8C41—C42—H42A108.5
C19—C18—H18B108.8C43—C42—H42A108.5
C17—C18—H18B108.8C41—C42—H42B108.5
H18A—C18—H18B107.7C43—C42—H42B108.5
C18—C19—C20114.23 (18)H42A—C42—H42B107.5
C18—C19—H19A108.7C44—C43—C42112.5 (2)
C20—C19—H19A108.7C44—C43—H43A109.1
C18—C19—H19B108.7C42—C43—H43A109.1
C20—C19—H19B108.7C44—C43—H43B109.1
H19A—C19—H19B107.6C42—C43—H43B109.1
C21—C20—C19113.98 (19)H43A—C43—H43B107.8
C21—C20—H20A108.8C43—C44—H44A109.5
C19—C20—H20A108.8C43—C44—H44B109.5
C21—C20—H20B108.8H44A—C44—H44B109.5
C19—C20—H20B108.8C43—C44—H44C109.5
H20A—C20—H20B107.7H44A—C44—H44C109.5
C20—C21—C22113.7 (2)H44B—C44—H44C109.5
C20—C21—H21A108.8S4—Zn1—S3i68.266 (19)
C22—C21—H21A108.8S2—Zn1—S3i89.532 (19)
C20—C21—H21B108.8S3—Zn1—S3i90.553 (19)
C22—C21—H21B108.8S1—Zn1—S3i154.920 (19)
H21A—C21—H21B107.7C23i—S4—Zn195.32 (7)
S4—Zn1—S1—C1133.25 (7)C13—C14—C15—C16179.7 (2)
S2—Zn1—S1—C1−1.16 (6)C14—C15—C16—C17−178.5 (2)
S3—Zn1—S1—C1−111.56 (7)C15—C16—C17—C18−178.2 (2)
S4—Zn1—S2—C1−101.28 (7)C16—C17—C18—C19−178.9 (2)
S3—Zn1—S2—C1111.24 (7)C17—C18—C19—C20−179.0 (2)
S1—Zn1—S2—C11.15 (6)C18—C19—C20—C21−179.9 (2)
S4—Zn1—S3—C23−144.88 (7)C19—C20—C21—C22178.7 (2)
S2—Zn1—S3—C2312.59 (7)C24—N2—C23—S4i−176.67 (14)
S1—Zn1—S3—C2396.99 (7)C31—N2—C23—S4i−7.6 (2)
S2—Zn1—S4—C23i−71.68 (7)C24—N2—C23—S33.5 (3)
S3—Zn1—S4—C23i77.98 (7)C31—N2—C23—S3172.55 (14)
S1—Zn1—S4—C23i−160.44 (6)Zn1—S3—C23—N2−82.29 (16)
C9—N1—C1—S1171.79 (14)Zn1—S3—C23—S4i97.90 (10)
C2—N1—C1—S10.3 (3)C23—N2—C24—C25−112.7 (2)
C9—N1—C1—S2−7.7 (3)C31—N2—C24—C2577.9 (2)
C2—N1—C1—S2−179.22 (14)N2—C24—C25—C3064.7 (3)
Zn1—S1—C1—N1−177.87 (16)N2—C24—C25—C26−116.0 (2)
Zn1—S1—C1—S21.69 (9)C30—C25—C26—C27−0.9 (3)
Zn1—S2—C1—N1177.81 (16)C24—C25—C26—C27179.8 (2)
Zn1—S2—C1—S1−1.76 (10)C25—C26—C27—C280.4 (4)
C1—N1—C2—C3−98.4 (2)C26—C27—C28—C290.4 (4)
C9—N1—C2—C389.6 (2)C27—C28—C29—C30−0.7 (4)
N1—C2—C3—C864.1 (3)C28—C29—C30—C250.2 (4)
N1—C2—C3—C4−116.5 (2)C26—C25—C30—C290.6 (3)
C8—C3—C4—C5−0.6 (3)C24—C25—C30—C29179.9 (2)
C2—C3—C4—C5179.9 (2)C23—N2—C31—C3280.0 (2)
C3—C4—C5—C60.8 (4)C24—N2—C31—C32−110.3 (2)
C4—C5—C6—C7−0.8 (4)N2—C31—C32—C3383.7 (2)
C5—C6—C7—C80.6 (4)C31—C32—C33—C34170.34 (18)
C6—C7—C8—C3−0.4 (4)C32—C33—C34—C35−177.04 (18)
C4—C3—C8—C70.4 (3)C33—C34—C35—C36176.50 (19)
C2—C3—C8—C7179.9 (2)C34—C35—C36—C37−177.71 (19)
C1—N1—C9—C10121.0 (2)C35—C36—C37—C38178.65 (19)
C2—N1—C9—C10−67.1 (2)C36—C37—C38—C39179.98 (19)
N1—C9—C10—C11−56.0 (3)C37—C38—C39—C40−179.42 (19)
C9—C10—C11—C12−177.38 (19)C38—C39—C40—C41179.92 (18)
C10—C11—C12—C13−174.42 (19)C39—C40—C41—C42−178.47 (19)
C11—C12—C13—C14−177.7 (2)C40—C41—C42—C43179.18 (19)
C12—C13—C14—C15−179.3 (2)C41—C42—C43—C4470.9 (3)
Symmetry codes: (i) −x+2, −y, −z+1.
Table 1
Selected geometric parameters (Å, °) top
Zn1—S42.3396 (6)Zn1—S12.4420 (6)
Zn1—S22.3398 (6)Zn1—S3i2.8879 (6)
Zn1—S32.3711 (6)
S4—Zn1—S2136.18 (2)S1—Zn1—S3i154.92 (2)
Symmetry codes: (i) −x+2, −y, −z+1.
Acknowledgements top

We are grateful to the National Natural Science Foundation of China (grant No. 20761003, 20871061) and the National 973 Introducing Program (grant No. 2008CB617512) for financial support.

references
References top

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