Literature DB >> 22969499

Bis[N-benzyl-N-(2-phenyl-eth-yl)dithio-carbamato-κ(2)S,S']lead(II).

E Sathiyaraj, S Thirumaran, S Selvanayagam.   

Abstract

The mol-ecule of the title compound, [Pb(C(16)H(16)NS(2))(2)], is located on a twofold rotation axis, which runs through the Pb(II) atom. The two dithio-carbamate ligands coordinate the metal in a pyramidal configuration through the S atoms. The two phenyl rings of each dithocarbamate ligand are aligned at a dihedral angle of 78.4 (1)°. The mol-ecular conformation is stabilized by intra-molecular C-H⋯S inter-actions.

Entities:  

Year:  2012        PMID： 22969499      PMCID： PMC3435626          DOI： 10.1107/S1600536812036161

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For general background of the title compound, see: Davidovich et al. (2010 ▶); Picket & O’Brien (2001 ▶); Srinivasan & Thirumaran (2012 ▶); Sathiyaraj & Thirumaran (2012 ▶); Green et al. (2004 ▶); Koh et al. (2003 ▶). For the preparation, see: Sathiyaraj & Thirumaran (2012 ▶). For a related structure, see: Davidovich et al. (2010 ▶)

Experimental

Crystal data

[Pb(C16H16NS2)2] M = 780.03 Monoclinic, a = 28.5467 (12) Å b = 5.5321 (2) Å c = 19.4158 (8) Å β = 101.600 (2)° V = 3003.6 (2) Å3 Z = 4 Mo Kα radiation μ = 5.92 mm−1 T = 292 K 0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.384, T max = 0.384 13027 measured reflections 3711 independent reflections 3006 reflections with I > 2σ(I) R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.028 wR(F 2) = 0.062 S = 1.04 3711 reflections 177 parameters H-atom parameters constrained Δρmax = 0.43 e Å−3 Δρmin = −1.25 e Å−3 Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036161/bt5972sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812036161/bt5972Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
[Pb(C16H16NS2)2]F(000) = 1536
Mr = 780.03Dx = 1.725 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5527 reflections
a = 28.5467 (12) Åθ = 1.5–28.3°
b = 5.5321 (2) ŵ = 5.92 mm−1
c = 19.4158 (8) ÅT = 292 K
β = 101.600 (2)°Block, brown
V = 3003.6 (2) Å30.20 × 0.20 × 0.20 mm
Z = 4
Bruker SMART APEXII area-detector diffractometer3711 independent reflections
Radiation source: fine-focus sealed tube3006 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω and φ scansθmax = 28.3°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2008)h = −37→31
Tmin = 0.384, Tmax = 0.384k = −7→7
13027 measured reflectionsl = −25→25
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.062H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0254P)2 + 1.657P] where P = (Fo2 + 2Fc2)/3
3711 reflections(Δ/σ)max = 0.001
177 parametersΔρmax = 0.43 e Å−3
0 restraintsΔρmin = −1.25 e Å−3
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.
xyzUiso*/Ueq
Pb11.00001.14280 (3)0.75000.05084 (8)
S10.99115 (3)0.94809 (17)0.61154 (4)0.04494 (19)
S20.93213 (3)0.80487 (16)0.71424 (4)0.0473 (2)
N10.92789 (9)0.5899 (4)0.59107 (12)0.0373 (6)
C10.94871 (10)0.7651 (6)0.63419 (14)0.0339 (6)
C20.94211 (11)0.5417 (6)0.52408 (15)0.0440 (7)
H2A0.93970.36910.51530.053*
H2B0.97550.58620.52870.053*
C30.91358 (11)0.6706 (5)0.46061 (15)0.0343 (6)
C40.88722 (12)0.8758 (5)0.46490 (17)0.0427 (7)
H40.88530.93690.50890.051*
C50.86360 (12)0.9926 (6)0.40547 (17)0.0498 (8)
H50.84601.13170.40950.060*
C60.86593 (13)0.9041 (7)0.34018 (18)0.0571 (10)
H60.85010.98320.29990.069*
C70.89154 (14)0.6993 (8)0.33484 (17)0.0569 (10)
H70.89310.63910.29060.068*
C80.91528 (12)0.5799 (6)0.39433 (16)0.0453 (8)
H80.93230.43930.39000.054*
C90.89245 (11)0.4222 (6)0.61033 (17)0.0419 (7)
H9A0.89570.42250.66100.050*
H9B0.89920.25980.59620.050*
C100.84215 (12)0.4865 (8)0.5771 (2)0.0612 (10)
H10A0.83820.47560.52640.073*
H10B0.83600.65230.58880.073*
C110.80629 (12)0.3225 (6)0.60110 (19)0.0492 (8)
C120.78865 (14)0.1181 (7)0.5636 (2)0.0564 (9)
H120.80000.07620.52360.068*
C130.75473 (12)−0.0232 (7)0.58444 (19)0.0542 (9)
H130.7434−0.15990.55850.065*
C140.73735 (13)0.0338 (7)0.6428 (2)0.0579 (9)
H140.7137−0.06080.65610.070*
C150.75511 (14)0.2325 (8)0.68166 (19)0.0629 (10)
H150.74390.27190.72200.075*
C160.78937 (14)0.3730 (6)0.6612 (2)0.0584 (10)
H160.80150.50570.68850.070*
U11U22U33U12U13U23
Pb10.05114 (13)0.03239 (11)0.05977 (12)0.000−0.01087 (8)0.000
S10.0350 (4)0.0494 (5)0.0505 (4)−0.0041 (4)0.0088 (3)0.0104 (4)
S20.0515 (5)0.0542 (5)0.0374 (4)−0.0131 (4)0.0120 (4)−0.0068 (4)
N10.0362 (14)0.0397 (14)0.0366 (12)−0.0003 (11)0.0088 (11)−0.0024 (11)
C10.0303 (15)0.0344 (15)0.0355 (14)0.0031 (13)0.0033 (12)0.0036 (13)
C20.0473 (19)0.0463 (18)0.0398 (15)0.0094 (16)0.0121 (14)−0.0061 (15)
C30.0352 (16)0.0323 (16)0.0381 (14)−0.0058 (12)0.0142 (13)−0.0051 (12)
C40.0476 (19)0.0378 (18)0.0431 (16)−0.0015 (14)0.0100 (14)−0.0079 (14)
C50.054 (2)0.0366 (19)0.0565 (19)0.0008 (15)0.0067 (16)0.0025 (16)
C60.055 (2)0.068 (3)0.0470 (19)−0.0091 (19)0.0068 (17)0.0178 (18)
C70.062 (2)0.075 (3)0.0374 (17)−0.008 (2)0.0185 (17)−0.0050 (17)
C80.0453 (19)0.0483 (19)0.0460 (17)−0.0039 (15)0.0182 (15)−0.0098 (15)
C90.0423 (18)0.0355 (16)0.0459 (16)0.0000 (14)0.0045 (14)−0.0028 (14)
C100.041 (2)0.067 (3)0.076 (2)0.0087 (18)0.0135 (18)0.030 (2)
C110.0356 (18)0.052 (2)0.061 (2)0.0064 (15)0.0116 (16)0.0140 (17)
C120.052 (2)0.063 (3)0.057 (2)0.0107 (18)0.0173 (18)−0.0014 (19)
C130.049 (2)0.043 (2)0.066 (2)−0.0022 (16)0.0033 (17)−0.0008 (18)
C140.047 (2)0.057 (2)0.071 (2)−0.0051 (18)0.0141 (19)0.016 (2)
C150.069 (3)0.069 (3)0.058 (2)−0.007 (2)0.029 (2)−0.001 (2)
C160.058 (2)0.054 (2)0.063 (2)−0.0103 (17)0.0127 (19)−0.0096 (17)
Pb1—S2i2.6813 (8)C7—C81.384 (5)
Pb1—S22.6813 (8)C7—H70.9300
Pb1—S1i2.8597 (9)C8—H80.9300
Pb1—S12.8597 (9)C9—C101.494 (4)
S1—C11.703 (3)C9—H9A0.9700
S2—C11.727 (3)C9—H9B0.9700
N1—C11.339 (4)C10—C111.510 (5)
N1—C21.463 (4)C10—H10A0.9700
N1—C91.475 (4)C10—H10B0.9700
C2—C31.512 (4)C11—C161.378 (5)
C2—H2A0.9700C11—C121.384 (5)
C2—H2B0.9700C12—C131.368 (5)
C3—C41.373 (4)C12—H120.9300
C3—C81.391 (4)C13—C141.362 (5)
C4—C51.375 (4)C13—H130.9300
C4—H40.9300C14—C151.372 (6)
C5—C61.373 (5)C14—H140.9300
C5—H50.9300C15—C161.369 (5)
C6—C71.363 (5)C15—H150.9300
C6—H60.9300C16—H160.9300
S2i—Pb1—S291.59 (4)C8—C7—H7119.6
S2i—Pb1—S1i64.61 (2)C7—C8—C3119.8 (3)
S2—Pb1—S1i84.46 (2)C7—C8—H8120.1
S2i—Pb1—S184.46 (2)C3—C8—H8120.1
S2—Pb1—S164.61 (2)N1—C9—C10112.9 (3)
S1i—Pb1—S1135.74 (4)N1—C9—H9A109.0
C1—S1—Pb185.08 (10)C10—C9—H9A109.0
C1—S2—Pb190.43 (11)N1—C9—H9B109.0
C1—N1—C2121.3 (3)C10—C9—H9B109.0
C1—N1—C9122.5 (2)H9A—C9—H9B107.8
C2—N1—C9116.0 (2)C9—C10—C11112.1 (3)
N1—C1—S1121.2 (2)C9—C10—H10A109.2
N1—C1—S2119.2 (2)C11—C10—H10A109.2
S1—C1—S2119.63 (17)C9—C10—H10B109.2
N1—C2—C3116.0 (2)C11—C10—H10B109.2
N1—C2—H2A108.3H10A—C10—H10B107.9
C3—C2—H2A108.3C16—C11—C12117.3 (3)
N1—C2—H2B108.3C16—C11—C10121.0 (3)
C3—C2—H2B108.3C12—C11—C10121.7 (3)
H2A—C2—H2B107.4C13—C12—C11121.1 (3)
C4—C3—C8118.4 (3)C13—C12—H12119.5
C4—C3—C2123.5 (3)C11—C12—H12119.5
C8—C3—C2118.1 (3)C14—C13—C12120.8 (3)
C3—C4—C5121.3 (3)C14—C13—H13119.6
C3—C4—H4119.3C12—C13—H13119.6
C5—C4—H4119.3C13—C14—C15119.2 (3)
C6—C5—C4120.0 (3)C13—C14—H14120.4
C6—C5—H5120.0C15—C14—H14120.4
C4—C5—H5120.0C16—C15—C14120.1 (3)
C7—C6—C5119.5 (3)C16—C15—H15119.9
C7—C6—H6120.2C14—C15—H15119.9
C5—C6—H6120.2C15—C16—C11121.5 (3)
C6—C7—C8120.9 (3)C15—C16—H16119.2
C6—C7—H7119.6C11—C16—H16119.2
S2i—Pb1—S1—C191.43 (10)C3—C4—C5—C60.3 (5)
S2—Pb1—S1—C1−2.98 (10)C4—C5—C6—C70.4 (5)
S1i—Pb1—S1—C147.21 (10)C5—C6—C7—C8−0.1 (6)
S2i—Pb1—S2—C1−80.18 (10)C6—C7—C8—C3−0.8 (5)
S1i—Pb1—S2—C1−144.48 (10)C4—C3—C8—C71.4 (5)
S1—Pb1—S2—C12.93 (10)C2—C3—C8—C7−176.9 (3)
C2—N1—C1—S12.6 (4)C1—N1—C9—C10101.6 (3)
C9—N1—C1—S1177.5 (2)C2—N1—C9—C10−83.3 (3)
C2—N1—C1—S2−177.3 (2)N1—C9—C10—C11−176.3 (3)
C9—N1—C1—S2−2.4 (4)C9—C10—C11—C1687.0 (4)
Pb1—S1—C1—N1−175.1 (2)C9—C10—C11—C12−93.8 (4)
Pb1—S1—C1—S24.81 (16)C16—C11—C12—C131.9 (5)
Pb1—S2—C1—N1174.8 (2)C10—C11—C12—C13−177.3 (3)
Pb1—S2—C1—S1−5.11 (17)C11—C12—C13—C140.1 (5)
C1—N1—C2—C3−92.9 (3)C12—C13—C14—C15−1.5 (6)
C9—N1—C2—C391.9 (3)C13—C14—C15—C161.0 (6)
N1—C2—C3—C420.9 (5)C14—C15—C16—C111.1 (6)
N1—C2—C3—C8−160.9 (3)C12—C11—C16—C15−2.5 (5)
C8—C3—C4—C5−1.1 (5)C10—C11—C16—C15176.7 (4)
C2—C3—C4—C5177.0 (3)
D—H···AD—HH···AD···AD—H···A
C9—H9A···S20.972.492.986 (3)112
C2—H2B···S10.972.552.990 (4)107
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C9—H9A⋯S20.972.492.986 (3)112
C2—H2B⋯S10.972.552.990 (4)107
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