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In the title compound, [Zn2(C6H10NS2)4], the Zn atom is tetra­hedrally coordinated by one S,S′-bidentate and two S-monodentate dithio­carbamate ligands. The monodentate ligands also bridge to a second Zn atom, resulting in a metallacyclic dimer, generated by inversion symmetry.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806015479/hb2040sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806015479/hb2040Isup2.hkl
Contains datablock I

CCDC reference: 610778

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.034
  • wR factor = 0.079
  • Data-to-parameter ratio = 16.9

checkCIF/PLATON results

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Alert level C PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Zn1 - S1 .. 7.28 su PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.11 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: CrysAlis RED (Oxford Diffraction, 2004); cell refinement: CrysAlis RED; data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.

Bis(µ-piperidine-1-dithiocarboxylato-κ2S:S')[bis(piperidine-1- dithiocarboxylato-κ2S,S')zinc(II)] top
Crystal data top
[Zn2(C6H10NS2)4]Z = 1
Mr = 771.83F(000) = 400
Triclinic, P1Dx = 1.554 Mg m3
Hall symbol: -P 1Melting point: 503 K
a = 8.7109 (19) ÅMo Kα radiation, λ = 0.71073 Å
b = 9.624 (2) ÅCell parameters from 62 reflections
c = 11.3166 (16) Åθ = 3.8–23.3°
α = 103.343 (17)°µ = 1.98 mm1
β = 97.502 (15)°T = 293 K
γ = 112.87 (2)°Plate, colourless
V = 824.5 (3) Å30.25 × 0.16 × 0.03 mm
Data collection top
Oxford Diffraction Xcalibur2 CCD
diffractometer
2913 independent reflections
Radiation source: Enhance (Mo) X-ray Source1918 reflections with I > 2sσ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 8.6225 pixels mm-1θmax = 25.1°, θmin = 4.3°
ω/2θ scansh = 1010
Absorption correction: analytical
(CrysAlis RED; Oxford Diffraction, 2004)
k = 1111
Tmin = 0.644, Tmax = 0.915l = 1313
5594 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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H-atom parameters constrained
S = 0.93 w = 1/[σ2(Fo2) + (0.0367P)2]
where P = (Fo2 + 2Fc2)/3
2913 reflections(Δ/σ)max < 0.001
172 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
Zn10.85880 (5)0.28090 (5)0.39831 (4)0.03979 (15)
S10.67735 (11)0.04555 (12)0.21557 (9)0.0460 (3)
S20.58612 (11)0.19658 (12)0.43598 (8)0.0421 (3)
S30.97351 (11)0.50963 (11)0.33291 (9)0.0379 (2)
S40.90492 (12)0.74800 (12)0.51053 (9)0.0452 (3)
N10.3572 (3)0.0581 (3)0.2505 (3)0.0381 (7)
N20.6972 (4)0.5685 (4)0.2875 (3)0.0426 (8)
C10.5213 (4)0.0474 (4)0.2949 (3)0.0333 (8)
C20.2222 (4)0.0629 (5)0.3182 (3)0.0454 (10)
H2A0.27100.02350.39630.054*
H2B0.17690.16180.33790.054*
C30.0784 (5)0.0488 (5)0.2389 (4)0.0510 (11)
H3A0.12140.05550.22780.061*
H3B0.01270.05930.28220.061*
C40.0060 (5)0.1739 (5)0.1118 (4)0.0613 (12)
H4A0.07810.15530.06090.074*
H4B0.05150.27770.12200.074*
C50.1487 (5)0.1705 (6)0.0458 (4)0.0648 (13)
H5A0.10160.25800.03150.078*
H5B0.19480.07260.02470.078*
C60.2915 (5)0.1825 (5)0.1279 (4)0.0578 (12)
H6A0.24880.28590.14040.069*
H6B0.38440.17170.08650.069*
C70.8406 (4)0.6026 (4)0.3695 (3)0.0362 (9)
C80.5861 (5)0.6500 (5)0.3109 (4)0.0533 (11)
H8A0.58350.70670.25060.064*
H8B0.63180.72630.39420.064*
C90.4073 (5)0.5300 (5)0.2997 (4)0.0611 (13)
H9A0.33440.58380.31360.073*
H9B0.41020.47930.36420.073*
C100.3303 (5)0.4039 (5)0.1722 (4)0.0553 (11)
H10A0.31300.45150.10790.066*
H10B0.21960.32370.17130.066*
C110.4518 (5)0.3282 (5)0.1457 (4)0.0538 (11)
H11A0.45270.26560.20160.065*
H11B0.40960.25720.06040.065*
C120.6319 (5)0.4491 (5)0.1625 (4)0.0527 (11)
H12A0.70640.39630.15200.063*
H12B0.63410.50160.09870.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0255 (2)0.0380 (3)0.0465 (3)0.00815 (19)0.00375 (18)0.00915 (19)
S10.0294 (5)0.0440 (6)0.0476 (6)0.0091 (5)0.0092 (4)0.0038 (5)
S20.0288 (5)0.0457 (6)0.0335 (5)0.0066 (4)0.0039 (4)0.0016 (4)
S30.0259 (5)0.0374 (6)0.0465 (6)0.0111 (4)0.0111 (4)0.0095 (4)
S40.0379 (5)0.0457 (6)0.0415 (6)0.0206 (5)0.0018 (4)0.0034 (4)
N10.0257 (15)0.0352 (18)0.0393 (18)0.0070 (14)0.0044 (13)0.0005 (14)
N20.0301 (16)0.045 (2)0.0401 (18)0.0166 (15)0.0024 (14)0.0046 (14)
C10.0322 (19)0.034 (2)0.032 (2)0.0129 (17)0.0060 (15)0.0114 (16)
C20.0296 (19)0.052 (3)0.041 (2)0.0072 (18)0.0106 (17)0.0094 (18)
C30.036 (2)0.056 (3)0.052 (3)0.019 (2)0.0088 (19)0.005 (2)
C40.040 (2)0.079 (3)0.046 (3)0.020 (2)0.0047 (19)0.002 (2)
C50.053 (3)0.073 (3)0.043 (3)0.016 (2)0.003 (2)0.004 (2)
C60.035 (2)0.048 (3)0.061 (3)0.005 (2)0.007 (2)0.010 (2)
C70.0272 (18)0.030 (2)0.044 (2)0.0064 (16)0.0102 (17)0.0084 (16)
C80.043 (2)0.055 (3)0.055 (3)0.027 (2)0.0020 (19)0.002 (2)
C90.037 (2)0.089 (4)0.048 (3)0.032 (2)0.0036 (19)0.000 (2)
C100.034 (2)0.066 (3)0.049 (3)0.016 (2)0.0017 (19)0.004 (2)
C110.047 (2)0.050 (3)0.047 (3)0.016 (2)0.0052 (19)0.0001 (19)
C120.038 (2)0.067 (3)0.042 (2)0.023 (2)0.0005 (18)0.002 (2)
Geometric parameters (Å, º) top
Zn1—S4i2.3240 (11)C4—H4A0.9700
Zn1—S22.3256 (11)C4—H4B0.9700
Zn1—S32.3722 (12)C5—C61.511 (6)
Zn1—S12.4712 (13)C5—H5A0.9700
C1—S11.727 (3)C5—H5B0.9700
C1—S21.734 (3)C6—H6A0.9700
C7—S31.753 (3)C6—H6B0.9700
C7—S41.716 (3)C8—C91.503 (5)
S4—Zn1i2.3240 (11)C8—H8A0.9700
N1—C11.332 (4)C8—H8B0.9700
N1—C61.476 (4)C9—C101.520 (5)
N1—C21.477 (4)C9—H9A0.9700
N2—C71.329 (4)C9—H9B0.9700
N2—C121.474 (4)C10—C111.524 (5)
N2—C81.478 (4)C10—H10A0.9700
C2—C31.512 (5)C10—H10B0.9700
C2—H2A0.9700C11—C121.501 (5)
C2—H2B0.9700C11—H11A0.9700
C3—C41.513 (5)C11—H11B0.9700
C3—H3A0.9700C12—H12A0.9700
C3—H3B0.9700C12—H12B0.9700
C4—C51.525 (5)
S4i—Zn1—S2129.05 (4)C4—C5—H5B109.4
S4i—Zn1—S3105.56 (4)H5A—C5—H5B108.0
S2—Zn1—S3120.12 (4)N1—C6—C5110.9 (3)
S4i—Zn1—S1109.75 (4)N1—C6—H6A109.5
S2—Zn1—S175.86 (4)C5—C6—H6A109.5
S3—Zn1—S1110.18 (4)N1—C6—H6B109.5
C1—S1—Zn181.41 (12)C5—C6—H6B109.5
C1—S2—Zn185.74 (12)H6A—C6—H6B108.1
C7—S3—Zn1102.87 (12)N2—C7—S4120.1 (3)
C7—S4—Zn1i98.90 (13)N2—C7—S3121.1 (3)
C1—N1—C6123.3 (3)S4—C7—S3118.7 (2)
C1—N1—C2123.8 (3)N2—C8—C9109.4 (3)
C6—N1—C2113.0 (3)N2—C8—H8A109.8
C7—N2—C12124.8 (3)C9—C8—H8A109.8
C7—N2—C8123.2 (3)N2—C8—H8B109.8
C12—N2—C8112.0 (3)C9—C8—H8B109.8
N1—C1—S1122.6 (3)H8A—C8—H8B108.2
N1—C1—S2120.4 (3)C8—C9—C10112.4 (3)
S1—C1—S2116.98 (19)C8—C9—H9A109.1
N1—C2—C3110.2 (3)C10—C9—H9A109.1
N1—C2—H2A109.6C8—C9—H9B109.1
C3—C2—H2A109.6C10—C9—H9B109.1
N1—C2—H2B109.6H9A—C9—H9B107.9
C3—C2—H2B109.6C9—C10—C11109.2 (3)
H2A—C2—H2B108.1C9—C10—H10A109.8
C2—C3—C4111.8 (3)C11—C10—H10A109.8
C2—C3—H3A109.3C9—C10—H10B109.8
C4—C3—H3A109.3C11—C10—H10B109.8
C2—C3—H3B109.3H10A—C10—H10B108.3
C4—C3—H3B109.3C12—C11—C10112.3 (3)
H3A—C3—H3B107.9C12—C11—H11A109.1
C3—C4—C5110.7 (3)C10—C11—H11A109.1
C3—C4—H4A109.5C12—C11—H11B109.1
C5—C4—H4A109.5C10—C11—H11B109.1
C3—C4—H4B109.5H11A—C11—H11B107.9
C5—C4—H4B109.5N2—C12—C11111.4 (3)
H4A—C4—H4B108.1N2—C12—H12A109.4
C6—C5—C4111.1 (4)C11—C12—H12A109.4
C6—C5—H5A109.4N2—C12—H12B109.4
C4—C5—H5A109.4C11—C12—H12B109.4
C6—C5—H5B109.4H12A—C12—H12B108.0
S4i—Zn1—S1—C1126.94 (12)C3—C4—C5—C653.4 (5)
S2—Zn1—S1—C10.08 (12)C1—N1—C6—C5122.6 (4)
S3—Zn1—S1—C1117.23 (12)C2—N1—C6—C557.3 (4)
S4i—Zn1—S2—C1104.22 (12)C4—C5—C6—N154.7 (5)
S3—Zn1—S2—C1105.30 (12)C12—N2—C7—S4178.4 (3)
S1—Zn1—S2—C10.08 (12)C8—N2—C7—S40.2 (5)
S4i—Zn1—S3—C7140.31 (13)C12—N2—C7—S32.2 (5)
S2—Zn1—S3—C716.28 (13)C8—N2—C7—S3176.4 (3)
S1—Zn1—S3—C7101.25 (13)Zn1i—S4—C7—N2175.3 (3)
C6—N1—C1—S12.3 (5)Zn1i—S4—C7—S38.4 (2)
C2—N1—C1—S1177.8 (3)Zn1—S3—C7—N289.2 (3)
C6—N1—C1—S2176.5 (3)Zn1—S3—C7—S494.5 (2)
C2—N1—C1—S23.4 (5)C7—N2—C8—C9122.7 (4)
Zn1—S1—C1—N1178.7 (3)C12—N2—C8—C958.5 (4)
Zn1—S1—C1—S20.11 (17)N2—C8—C9—C1057.7 (5)
Zn1—S2—C1—N1178.8 (3)C8—C9—C10—C1154.3 (5)
Zn1—S2—C1—S10.12 (18)C9—C10—C11—C1251.9 (5)
C1—N1—C2—C3122.9 (4)C7—N2—C12—C11124.0 (4)
C6—N1—C2—C357.0 (4)C8—N2—C12—C1157.3 (4)
N1—C2—C3—C455.1 (4)C10—C11—C12—N254.0 (5)
C2—C3—C4—C553.9 (5)
Symmetry code: (i) x+2, y+1, z+1.
 

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