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The Pb atom in the title compound, [Pb(C9H16NS2)2], is chelated in an anisobidentate manner by the di­thio­carbamate group [Pb—S = 2.710 (2)/2.883(2) Å and 2.700 (2)/2.841(2) Å]. The four-coordinate geometry is raised to six through the involvement of the double-bonded S atoms of adjacent di­thio­carbamato groups; the Pb...S interactions [Pb...S = 3.457 (2) and 3.508 (2) Å] result in a chain structure for the compound.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536800020146/na6024sup1.cif
Contains datablocks I, aho33m

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536800020146/na6024Isup2.hkl
Contains datablock I

CCDC reference: 155845

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.053
  • wR factor = 0.146
  • Data-to-parameter ratio = 35.3

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 33.18 From the CIF: _reflns_number_total 7977 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 8816 Completeness (_total/calc) 90.48% Alert C: < 95% complete PLAT_702 Alert C Angle Calc 122.04(5), Rep 122.10(10), Dev. 1.20 Sigma S2 -PB1 -S3 2.565 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check

Comment top

Several lead(II) dithiocarbamates have been reported in the literature, e.g. bis(dimethyldithiocarbamato)lead (Iwasaki, 1980), bis(diethyldithiocarbamato)lead (Zvonkova et al., 1967), bis(diisopropyldithiocarbamato)lead (Ito & Iwasaki, 1980) and bis(N-ethyl-N-isopropyldithiocarbamato)lead(II) (Trindade, 1997; Ng, 1999). These compounds, as well as the title dithiocarbamate, (I), have the Pb atoms in a distorted tetrahedral geometry, and adjacent molecules are linked by Pb···S interactions into chains. The bond dimensions as well as the interactions in the title compound are similar to those found in other dithiocarbamates, and the size of the cyclohexyl ring does not appear to affect the packing.

Experimental top

An excess quantity of carbon disulfide was added dropwise to a solution of lead(II) chloride and ethylcyclohexylamine (1:2 molar ratio) in ethanol. The dithiocarbamate slowly separated from solution; this was collected and air dried to afford crystals (m.p. 421–422 K). Elemental analysis, found (calculated in parenthesis): C 35.37 (35.36), H 4.75 (5.23), N 4.73 (4.58), S 21.44% (20.96%).

Refinement top

The diffraction data are complete to θ = 25°; the overall, slightly low, completeness of the diffraction data is because of the incompleteness in the 25 < θ < 33° range.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson, 1976) plot of (I) at the 50% probability level. H atoms are drawn as spheres of arbitrary radii.
Di(N-cyclohexyl-N-ethyldithiocarbamato)lead(II) top
Crystal data top
[Pb(C9H16NS2)2]Z = 2
Mr = 611.89F(000) = 600
Triclinic, P1Dx = 1.763 Mg m3
a = 9.7180 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.1871 (2) ÅCell parameters from 4596 reflections
c = 11.8751 (3) Åθ = 2.7–33.2°
α = 95.586 (1)°µ = 7.69 mm1
β = 92.978 (1)°T = 298 K
γ = 99.142 (1)°Parallelepiped, yellow
V = 1152.45 (4) Å30.48 × 0.28 × 0.24 mm
Data collection top
Siemens CCD area-detector
diffractometer
7977 independent reflections
Radiation source: fine-focus sealed tube4557 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.030
Detector resolution: 8.33 pixels mm-1θmax = 33.2°, θmin = 2.7°
ω scansh = 1114
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
k = 1515
Tmin = 0.073, Tmax = 0.158l = 1814
10652 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.146Riding
S = 0.99 w = 1/[σ2(Fo2) + (0.065P)2]
where P = (Fo2 + 2Fc2)/3
7977 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 1.32 e Å3
0 restraintsΔρmin = 2.09 e Å3
Crystal data top
[Pb(C9H16NS2)2]γ = 99.142 (1)°
Mr = 611.89V = 1152.45 (4) Å3
Triclinic, P1Z = 2
a = 9.7180 (2) ÅMo Kα radiation
b = 10.1871 (2) ŵ = 7.69 mm1
c = 11.8751 (3) ÅT = 298 K
α = 95.586 (1)°0.48 × 0.28 × 0.24 mm
β = 92.978 (1)°
Data collection top
Siemens CCD area-detector
diffractometer
7977 independent reflections
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
4557 reflections with I > 2σ(I)
Tmin = 0.073, Tmax = 0.158Rint = 0.030
10652 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.146Riding
S = 0.99Δρmax = 1.32 e Å3
7977 reflectionsΔρmin = 2.09 e Å3
226 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pb10.26984 (2)0.58470 (2)0.01673 (2)0.06438 (12)
S10.2738 (2)0.6822 (2)0.2377 (2)0.0620 (4)
S20.0133 (2)0.6614 (2)0.0908 (1)0.0527 (4)
S30.3307 (2)0.8183 (2)0.0739 (2)0.0670 (5)
S40.5590 (2)0.6878 (2)0.0151 (2)0.0589 (4)
N10.0238 (5)0.6901 (5)0.3178 (4)0.048 (1)
N20.5912 (5)0.8659 (5)0.1366 (4)0.046 (1)
C10.0955 (6)0.6786 (6)0.2237 (5)0.047 (1)
C20.1298 (6)0.6725 (6)0.3106 (5)0.045 (1)
C30.1934 (7)0.5330 (7)0.3345 (7)0.063 (2)
C40.3511 (8)0.5127 (9)0.3260 (9)0.082 (2)
C50.4042 (8)0.6166 (9)0.4025 (7)0.076 (2)
C60.3440 (8)0.7535 (9)0.3749 (7)0.073 (2)
C70.1849 (8)0.7787 (7)0.3862 (6)0.064 (2)
C80.0969 (8)0.705 (1)0.4313 (6)0.077 (2)
C90.164 (1)0.849 (1)0.4694 (7)0.107 (4)
C100.5050 (6)0.7973 (6)0.0719 (5)0.048 (1)
C110.7372 (5)0.8396 (6)0.1447 (5)0.042 (1)
C120.7452 (7)0.7291 (6)0.2378 (6)0.056 (2)
C130.8931 (8)0.6965 (8)0.2398 (7)0.067 (2)
C140.9985 (7)0.8210 (8)0.2514 (6)0.064 (2)
C150.9891 (6)0.9292 (7)0.1576 (6)0.061 (2)
C160.8413 (7)0.9647 (6)0.1588 (6)0.055 (1)
C170.5429 (7)0.9666 (7)0.2039 (6)0.061 (2)
C180.491 (1)0.912 (1)0.3226 (8)0.107 (3)
H2a0.15980.68210.23220.054*
H3a0.16230.46780.28080.076*
H3b0.16080.51800.41000.076*
H4a0.38440.51730.24830.099*
H4b0.38760.42460.34650.099*
H5a0.50540.60400.39300.091*
H5b0.37800.60730.48090.091*
H6a0.37850.81970.42540.088*
H6b0.37550.76380.29790.088*
H7a0.15000.86660.36440.076*
H7b0.15250.77620.46450.076*
H8a0.16880.64940.43050.093*
H8b0.03090.67490.48550.093*
H9a0.20950.85440.54360.160*
H9b0.09250.90500.47180.160*
H9c0.23050.87940.41700.160*
H11a0.76490.80790.07300.050*
H12a0.71790.75670.31040.068*
H12b0.68060.64970.22540.068*
H13a0.91650.65960.17040.080*
H13b0.89750.62970.30300.080*
H14a1.09200.79890.24850.077*
H14b0.98070.85300.32410.077*
H15a1.05601.00820.16710.073*
H15b1.01250.89920.08510.073*
H16a0.83631.03360.09740.066*
H16b0.81900.99870.22980.066*
H17a0.61941.03980.20630.073*
H17b0.46841.00230.16630.073*
H18a0.46120.98160.36200.160*
H18b0.41370.84070.32110.160*
H18c0.56480.87830.36110.160*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.0459 (1)0.0562 (2)0.0867 (2)0.0016 (1)0.0234 (1)0.0127 (1)
S10.0356 (7)0.077 (1)0.074 (1)0.0031 (7)0.0074 (7)0.0165 (9)
S20.0407 (7)0.0666 (9)0.0471 (8)0.0019 (6)0.0098 (6)0.0058 (7)
S30.0411 (8)0.090 (1)0.076 (1)0.0244 (8)0.0148 (8)0.012 (1)
S40.0452 (8)0.069 (1)0.070 (1)0.0149 (7)0.0187 (7)0.0269 (8)
N10.040 (2)0.060 (3)0.042 (3)0.000 (2)0.004 (2)0.015 (2)
N20.039 (2)0.047 (3)0.053 (3)0.011 (2)0.005 (2)0.007 (2)
C10.039 (3)0.038 (3)0.063 (4)0.000 (2)0.011 (3)0.005 (2)
C20.041 (3)0.054 (3)0.040 (3)0.008 (2)0.013 (2)0.006 (2)
C30.051 (4)0.050 (3)0.090 (5)0.006 (3)0.010 (3)0.012 (3)
C40.055 (4)0.074 (5)0.111 (7)0.009 (4)0.016 (4)0.005 (5)
C50.046 (4)0.104 (6)0.081 (5)0.010 (4)0.016 (3)0.024 (5)
C60.074 (5)0.088 (5)0.068 (4)0.040 (4)0.025 (4)0.012 (4)
C70.071 (4)0.061 (4)0.059 (4)0.012 (3)0.018 (3)0.001 (3)
C80.053 (4)0.126 (7)0.054 (4)0.004 (4)0.009 (3)0.028 (4)
C90.089 (6)0.149 (9)0.056 (5)0.043 (6)0.002 (4)0.012 (5)
C100.037 (3)0.057 (3)0.050 (3)0.014 (2)0.009 (2)0.001 (3)
C110.033 (2)0.050 (3)0.042 (3)0.005 (2)0.005 (2)0.007 (2)
C120.051 (3)0.049 (3)0.064 (4)0.003 (3)0.004 (3)0.009 (3)
C130.057 (4)0.066 (4)0.079 (5)0.019 (3)0.015 (3)0.007 (4)
C140.052 (4)0.092 (5)0.056 (4)0.022 (4)0.020 (3)0.016 (4)
C150.039 (3)0.074 (4)0.068 (4)0.001 (3)0.011 (3)0.010 (3)
C160.054 (3)0.047 (3)0.062 (4)0.001 (3)0.009 (3)0.001 (3)
C170.051 (4)0.056 (4)0.077 (5)0.012 (3)0.001 (3)0.016 (3)
C180.132 (9)0.106 (7)0.088 (7)0.037 (7)0.026 (6)0.028 (6)
Geometric parameters (Å, º) top
Pb1—S12.710 (2)C3—H3a0.9700
Pb1—S22.883 (2)C3—H3b0.9700
Pb1—S2i3.508 (2)C4—H4a0.9700
Pb1—S32.700 (2)C4—H4b0.9700
Pb1—S42.841 (2)C5—H5a0.9700
Pb1—S4ii3.457 (2)C5—H5b0.9700
S1—C11.726 (6)C6—H6a0.9700
S2—C11.712 (6)C6—H6b0.9700
S3—C101.740 (6)C7—H7a0.9700
S4—C101.714 (6)C7—H7b0.9700
N1—C11.353 (7)C8—H8a0.9700
N1—C21.472 (7)C8—H8b0.9700
N1—C81.473 (9)C9—H9a0.9600
N2—C101.329 (7)C9—H9b0.9600
N2—C171.478 (8)C9—H9c0.9600
N2—C111.492 (7)C11—H11a0.9800
C2—C31.517 (8)C12—H12a0.9700
C2—C71.520 (8)C12—H12b0.9700
C3—C41.51 (1)C13—H13a0.9700
C4—C51.50 (1)C13—H13b0.9700
C5—C61.50 (1)C14—H14a0.9700
C6—C71.52 (1)C14—H14b0.9700
C8—C91.52 (1)C15—H15a0.9700
C11—C121.513 (8)C15—H15b0.9700
C11—C161.524 (8)C16—H16a0.9700
C12—C131.527 (9)C16—H16b0.9700
C13—C141.52 (1)C17—H17a0.9700
C14—C151.51 (1)C17—H17b0.9700
C15—C161.535 (9)C18—H18a0.9600
C17—C181.50 (1)C18—H18b0.9600
C2—H2a0.9800C18—H18c0.9600
S1—Pb1—S264.0 (1)C6—C5—H5b109.7
S1—Pb1—S2i117.3 (1)C4—C5—H5b109.7
S1—Pb1—S398.9 (1)H5a—C5—H5b108.2
S1—Pb1—S490.0 (1)C5—C6—H6a109.2
S1—Pb1—S4ii111.4 (1)C7—C6—H6a109.2
S2—Pb1—S2i70.4 (1)C5—C6—H6b109.2
S2—Pb1—S389.9 (1)C7—C6—H6b109.2
S2—Pb1—S4140.9 (1)H6a—C6—H6b107.9
S2—Pb1—S4ii141.6 (1)C2—C7—H7a109.7
S2i—Pb1—S3122.1 (1)C6—C7—H7a109.7
S2i—Pb1—S4148.0 (1)C2—C7—H7b109.7
S2i—Pb1—S4ii80.8 (1)C6—C7—H7b109.7
S3—Pb1—S464.6 (1)H7a—C7—H7b108.2
S3—Pb1—S4ii127.5 (1)N1—C8—H8a109.1
S4—Pb1—S4ii73.3 (1)C9—C8—H8a109.1
C1—S1—Pb190.0 (2)N1—C8—H8b109.1
C1—S2—Pb184.6 (2)C9—C8—H8b109.1
C10—S3—Pb188.9 (2)H8a—C8—H8b107.8
C10—S4—Pb184.9 (2)C8—C9—H9a109.5
C1—N1—C2121.4 (5)C8—C9—H9b109.5
C1—N1—C8120.4 (5)H9a—C9—H9b109.5
C2—N1—C8117.9 (5)C8—C9—H9c109.5
C10—N2—C17120.6 (5)H9a—C9—H9c109.5
C10—N2—C11120.3 (4)H9b—C9—H9c109.5
C17—N2—C11119.0 (5)N2—C11—H11a107.0
N1—C1—S2121.4 (4)C12—C11—H11a107.0
N1—C1—S1119.4 (5)C16—C11—H11a107.0
S2—C1—S1119.2 (3)C11—C12—H12a109.5
N1—C2—C3111.3 (5)C13—C12—H12a109.5
N1—C2—C7112.7 (5)C11—C12—H12b109.5
C3—C2—C7111.2 (5)C13—C12—H12b109.5
C4—C3—C2112.0 (6)H12a—C12—H12b108.1
C5—C4—C3111.2 (7)C14—C13—H13a109.5
C6—C5—C4109.9 (6)C12—C13—H13a109.5
C5—C6—C7112.3 (6)C14—C13—H13b109.5
C2—C7—C6109.6 (6)C12—C13—H13b109.5
N1—C8—C9112.5 (7)H13a—C13—H13b108.0
N2—C10—S4122.4 (4)C15—C14—H14a109.5
N2—C10—S3119.5 (4)C13—C14—H14a109.5
S4—C10—S3118.0 (3)C15—C14—H14b109.5
N2—C11—C12111.2 (5)C13—C14—H14b109.5
N2—C11—C16113.1 (5)H14a—C14—H14b108.1
C12—C11—C16111.1 (5)C14—C15—H15a109.5
C11—C12—C13110.7 (5)C16—C15—H15a109.5
C14—C13—C12110.9 (6)C14—C15—H15b109.5
C15—C14—C13110.7 (5)C16—C15—H15b109.5
C14—C15—C16110.7 (6)H15a—C15—H15b108.1
C11—C16—C15109.0 (5)C11—C16—H16a109.9
N2—C17—C18113.3 (6)C15—C16—H16a109.9
N1—C2—H2a107.1C11—C16—H16b109.9
C3—C2—H2a107.1C15—C16—H16b109.9
C7—C2—H2a107.1H16a—C16—H16b108.3
C4—C3—H3a109.2N2—C17—H17a108.9
C2—C3—H3a109.2C18—C17—H17a108.9
C4—C3—H3b109.2N2—C17—H17b108.9
C2—C3—H3b109.2C18—C17—H17b108.9
H3a—C3—H3b107.9H17a—C17—H17b107.7
C5—C4—H4a109.4C17—C18—H18a109.5
C3—C4—H4a109.4C17—C18—H18b109.5
C5—C4—H4b109.4H18a—C18—H18b109.5
C3—C4—H4b109.4C17—C18—H18c109.5
H4a—C4—H4b108.0H18a—C18—H18c109.5
C6—C5—H5a109.7H18b—C18—H18c109.5
C4—C5—H5a109.7
S3—Pb1—S1—C194.1 (2)N1—C2—C3—C4179.3 (6)
S4—Pb1—S1—C1158.4 (2)C7—C2—C3—C454.2 (9)
S2—Pb1—S1—C18.7 (2)C2—C3—C4—C556 (1)
S4ii—Pb1—S1—C1129.6 (2)C3—C4—C5—C657 (1)
S2i—Pb1—S1—C139.1 (2)C4—C5—C6—C758.3 (9)
S3—Pb1—S2—C1108.7 (2)N1—C2—C7—C6179.6 (5)
S1—Pb1—S2—C18.8 (2)C3—C2—C7—C653.8 (7)
S4—Pb1—S2—C161.8 (2)C5—C6—C7—C256.8 (8)
S4ii—Pb1—S2—C183.3 (2)C1—N1—C8—C982.7 (9)
S2i—Pb1—S2—C1126.9 (2)C2—N1—C8—C9104.1 (7)
S1—Pb1—S3—C1096.7 (2)C17—N2—C10—S4175.5 (5)
S4—Pb1—S3—C1011.0 (2)C11—N2—C10—S46.2 (8)
S2—Pb1—S3—C10160.3 (2)C17—N2—C10—S34.3 (8)
S4ii—Pb1—S3—C1029.0 (2)C11—N2—C10—S3174.0 (4)
S2i—Pb1—S3—C10133.1 (2)Pb1—S4—C10—N2162.3 (5)
S3—Pb1—S4—C1011.2 (2)Pb1—S4—C10—S317.9 (3)
S1—Pb1—S4—C10111.0 (2)Pb1—S3—C10—N2161.4 (5)
S2—Pb1—S4—C1065.1 (2)Pb1—S3—C10—S418.8 (3)
S4ii—Pb1—S4—C10136.7 (2)C10—N2—C11—C1288.0 (7)
S2i—Pb1—S4—C1099.2 (2)C17—N2—C11—C1290.4 (6)
C2—N1—C1—S27.3 (8)C10—N2—C11—C16146.2 (5)
C8—N1—C1—S2179.7 (5)C17—N2—C11—C1635.4 (7)
C2—N1—C1—S1173.0 (4)N2—C11—C12—C13176.1 (5)
C8—N1—C1—S10.1 (8)C16—C11—C12—C1357.0 (7)
Pb1—S2—C1—N1166.1 (5)C11—C12—C13—C1455.4 (8)
Pb1—S2—C1—S114.3 (3)C12—C13—C14—C1556.2 (8)
Pb1—S1—C1—N1165.2 (5)C13—C14—C15—C1658.2 (8)
Pb1—S1—C1—S215.1 (3)N2—C11—C16—C15176.0 (5)
C1—N1—C2—C398.6 (7)C12—C11—C16—C1558.1 (7)
C8—N1—C2—C374.5 (8)C14—C15—C16—C1158.7 (7)
C1—N1—C2—C7135.6 (6)C10—N2—C17—C1893.5 (9)
C8—N1—C2—C751.3 (8)C11—N2—C17—C1884.8 (8)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula[Pb(C9H16NS2)2]
Mr611.89
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)9.7180 (2), 10.1871 (2), 11.8751 (3)
α, β, γ (°)95.586 (1), 92.978 (1), 99.142 (1)
V3)1152.45 (4)
Z2
Radiation typeMo Kα
µ (mm1)7.69
Crystal size (mm)0.48 × 0.28 × 0.24
Data collection
DiffractometerSiemens CCD area-detector
diffractometer
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.073, 0.158
No. of measured, independent and
observed [I > 2σ(I)] reflections
10652, 7977, 4557
Rint0.030
(sin θ/λ)max1)0.770
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.146, 0.99
No. of reflections7977
No. of parameters226
H-atom treatmentRiding
Δρmax, Δρmin (e Å3)1.32, 2.09

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97.

Selected geometric parameters (Å, º) top
Pb1—S12.710 (2)Pb1—S32.700 (2)
Pb1—S22.883 (2)Pb1—S42.841 (2)
Pb1—S2i3.508 (2)Pb1—S4ii3.457 (2)
S1—Pb1—S264.0 (1)S2—Pb1—S4ii141.6 (1)
S1—Pb1—S2i117.3 (1)S2i—Pb1—S3122.1 (1)
S1—Pb1—S398.9 (1)S2i—Pb1—S4148.0 (1)
S1—Pb1—S490.0 (1)S2i—Pb1—S4ii80.8 (1)
S1—Pb1—S4ii111.4 (1)S3—Pb1—S464.6 (1)
S2—Pb1—S2i70.4 (1)S3—Pb1—S4ii127.5 (1)
S2—Pb1—S389.9 (1)S4—Pb1—S4ii73.3 (1)
S2—Pb1—S4140.9 (1)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z.
 

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