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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 8| August 2013| Page m457
doi:10.1107/S1600536813019259

Bis{N-benzyl-N-[2-(thio­phen-2-yl)eth­yl]di­thio­carbamato-κ2S,S′}lead(II)

E. Sathiyaraj,a S. Thirumaran,a B. Sridharb and S. Selvanayagamc*

aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, India, bLaboratory of X-ray Crystallography, Indian Institute of Chemical Technology, Hyderabad 500 007, India, and cDepartment of Physics, Kalasalingam University, Krishnankoil 626 126, India
*Correspondence e-mail: s_selvanayagam@rediffmail.com

(Received 6 July 2013; accepted 11 July 2013; online 17 July 2013)

The mol­ecule of the title compound, [Pb(C14H14NS3)2], is located on a twofold rotation axis. The di­thio­carbamate anion S,S′-chelates to the PbII atom, which shows a Ψ-trigonal–bipyramidal coordination. The thio­phene ring is disordered over two positions, the major component having 71.3 (7)% occupancy. The mol­ecular conformation is stabilized by intra­molecular C—H⋯S inter­actions.

Related literature

For a related structure, see: Sathiyaraj et al. (2012[Sathiyaraj, E., Thirumaran, S. & Selvanayagam, S. (2012). Acta Cryst. E68, m1217.]). For the superposition of structures, see: Gans & Shalloway (2001[Gans, J. D. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.]).

[Scheme 1]

Experimental

Crystal data

  • [Pb(C14H14NS3)2]

  • Mr = 792.07

  • Monoclinic, C 2/c

  • a = 27.459 (2) Å

  • b = 5.5580 (4) Å

  • c = 19.4670 (15) Å

  • β = 100.168 (2)°

  • V = 2924.3 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 6.22 mm−1

  • T = 292 K

  • 0.20 × 0.08 × 0.06 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.699, Tmax = 0.707

  • 16187 measured reflections

  • 3487 independent reflections

  • 3089 reflections with I > 2σ(I)

  • Rint = 0.023
Refinement

  • R[F2 > 2σ(F2)] = 0.026

  • wR(F2) = 0.074

  • S = 1.01

  • 3487 reflections

  • 172 parameters

  • 23 restraints

  • H-atom parameters constrained

  • Δρmax = 0.91 e Å−3

  • Δρmin = −0.84 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H2A⋯S1 0.97 2.47 2.998 (4) 114
C8—H8B⋯S2 0.97 2.53 2.988 (4) 109

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SMART, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2013 and PLATON (Spek, 2009)[Spek, A. L. (2009). Acta Cryst. D65, 148-155.].

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536813019259/ng5336sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813019259/ng5336Isup2.hkl

checkCIF report


Comment top

In continuation of our work on the crystal structure analysis of lead complexes, we have undertaken a single-crystal X-ray diffraction study for the title compound, and the results are presented here.

The X-ray study confirmed the molecular structure and atomic connectivity for (I), as illustrated in Fig. 1. The Pb atom is coordinated by four sulfur atom from two dithiocarbamate anions. The asymmetry in Pb-S bonds suggests that the lone pair on Pb(II) is stereochemically active. The geometry of this coordination PbS4 polyhedron is trigonal bipyramid. The geometry is similar to that reported for bis[N-benzyl-N-(2-phenylethyl)dithiocarbamato]lead(II) (Sathiyaraj et al., 2012).The superposition of the coordination polyhedron (PbS4) of (I) with this related reported structure, using Qmol (Gans & Shalloway, 2001) shows the r.m.s. deviation is 0.005 Å.

The sum of the angles at N1 [359.7°] is in accordance with sp2 hybridization. The thiophene ring is disordered over two positions, with a major component being 71.3 (7)%. The dihedral angles between the phenyl and the major and minor components of the thiophene ring are 74.8 (1) and 74.7 (1)°, respectively.

In addition to the van der Waals interactions, the molecular structure is influenced only by intramolecular C—H···S hydrogen bonds.

Related literature top

For a related structure, see: Sathiyaraj et al. (2012). For the superposition of structures, see: Gans & Shalloway (2001).

Experimental top

Benzyl(2-(thiophene-2-yl)ethyl)amine (4 mmol) and carbon disulfide (4 mmol) were dissolved in ethanol (20ml) and stirred for 30minutes. To this solution, an aqueous solution (100 ml) of Pb(NO3)2 (2 mmol) was added with constant stirring. A pale yellow powder precipitated that was filtered and dried. Single crystals of (I) were obtained by slow evaporation of dichloromethane and acetone (1:1) solution of the title compound at room temperature.

Refinement top

H atoms were placed in idealized positions and allowed to ride on their parent atoms, with C—H distances of 0.93-0.97 Å, and Uiso(H) = 1.2Ueq(C) for H atoms. The thiophene ring is disordered over two positions, with a major component being 71.3 (7)%. Pairs of C—S, C—C and C=C bond distances were restrained to 1.74 (1), 1.43 (1) and 1.37 (1) Å, respectively. The bond distances C3—C4 and C3—C4' were restrained to within 0.01 Å of each other. The temperature factors of C5' was set to those of S3 (as were these pairs: C4' to C4, S3' to C5, C6' to C6 and C7' to C7). The planarity of thiophene ring atoms were restrained to within 0.01 Å3 of each other. Pairs of C—S and C—C 1,3 bond distances were restrained to the values of 2.58 (1) and 2.33 (1) Å, respectively.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008); PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. The minor occupied atoms of the disordered part have been omitted for clarity
Bis{N-benzyl-N-[2-(thiophen-2-yl)ethyl]dithiocarbamato-κ2S,S'}lead(II) top
Crystal data top
[Pb(C14H14NS3)2]F(000) = 1552
Mr = 792.07Dx = 1.799 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 27.459 (2) ÅCell parameters from 8428 reflections
b = 5.5580 (4) Åθ = 2.5–27.6°
c = 19.4670 (15) ŵ = 6.22 mm−1
β = 100.168 (2)°T = 292 K
V = 2924.3 (4) Å3Needle, yellow
Z = 40.20 × 0.08 × 0.06 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3089 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
ω scansθmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		h = −35→35
Tmin = 0.699, Tmax = 0.707k = −7→7
16187 measured reflectionsl = −25→25
3487 independent reflections
Refinement top
Refinement on F223 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026H-atom parameters constrained
wR(F2) = 0.074 w = 1/[σ2(Fo2) + (0.0483P)2 + 2.5197P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max = 0.001
3487 reflectionsΔρmax = 0.91 e Å−3
172 parametersΔρmin = −0.84 e Å−3
Crystal data top
[Pb(C14H14NS3)2]V = 2924.3 (4) Å3
Mr = 792.07Z = 4
Monoclinic, C2/cMo Kα radiation
a = 27.459 (2) ŵ = 6.22 mm−1
b = 5.5580 (4) ÅT = 292 K
c = 19.4670 (15) Å0.20 × 0.08 × 0.06 mm
β = 100.168 (2)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer		3487 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3089 reflections with I > 2σ(I)
Tmin = 0.699, Tmax = 0.707Rint = 0.023
16187 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.02623 restraints
wR(F2) = 0.074H-atom parameters constrained
S = 1.01Δρmax = 0.91 e Å−3
3487 reflectionsΔρmin = −0.84 e Å−3
172 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
Pb10.50001.14399 (3)0.75000.06000 (9)
S10.42993 (3)0.80812 (17)0.71606 (4)0.0567 (2)
S20.49150 (3)0.95155 (16)0.61228 (4)0.05250 (18)
N10.42564 (10)0.5970 (5)0.59289 (13)0.0471 (5)
C10.44701 (10)0.7691 (6)0.63555 (14)0.0422 (5)
C20.38975 (13)0.4246 (6)0.61323 (18)0.0540 (7)
H2A0.39010.43890.66300.065*
H2B0.40000.26230.60420.065*
C30.33791 (14)0.4638 (10)0.5748 (3)0.0812 (13)
H3A0.32870.63020.58050.097*
H3B0.33700.43560.52550.097*
S30.28129 (10)0.3223 (5)0.67259 (11)0.0953 (8)0.713 (7)
C40.3015 (4)0.3061 (14)0.5993 (4)0.0749 (18)0.713 (7)
C50.2819 (4)0.1084 (14)0.5602 (4)0.098 (2)0.713 (7)
H50.28930.06920.51680.118*0.713 (7)
C60.2487 (2)−0.0298 (10)0.5950 (4)0.087 (2)0.713 (7)
H60.2320−0.16740.57660.105*0.713 (7)
C70.2449 (3)0.0673 (15)0.6581 (4)0.096 (3)0.713 (7)
H70.22560.00570.68870.115*0.713 (7)
S3'0.2817 (3)0.0438 (10)0.5716 (4)0.098 (2)0.287 (7)
C4'0.3056 (10)0.273 (4)0.5972 (14)0.0749 (18)0.287 (7)
C5'0.2874 (9)0.372 (3)0.6629 (9)0.0953 (8)0.287 (7)
H5'0.29780.51330.68680.114*0.287 (7)
C6'0.2511 (6)0.204 (3)0.6800 (6)0.087 (2)0.287 (7)
H6'0.23440.22240.71740.105*0.287 (7)
C7'0.2443 (6)0.015 (3)0.6342 (9)0.096 (3)0.287 (7)
H7'0.2226−0.11140.63640.115*0.287 (7)
C80.44094 (12)0.5488 (6)0.52616 (16)0.0519 (7)
H8A0.43920.37660.51800.062*
H8B0.47530.59630.52980.062*
C90.41122 (7)0.6731 (3)0.46313 (8)0.0426 (6)
C100.41287 (8)0.5775 (3)0.39761 (10)0.0541 (7)
H100.43070.43730.39360.065*
C110.38794 (9)0.6913 (4)0.33807 (8)0.0647 (9)
H110.38900.62730.29420.078*
C120.36135 (9)0.9008 (4)0.34405 (9)0.0665 (9)
H120.34470.97690.30420.080*
C130.35970 (8)0.9964 (3)0.40957 (11)0.0597 (8)
H130.34191.13660.41360.072*
C140.38463 (8)0.8826 (3)0.46911 (8)0.0513 (7)
H140.38350.94660.51290.062*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.06332 (13)0.04215 (11)0.06445 (13)0.000−0.01642 (8)0.000
S10.0622 (5)0.0666 (5)0.0418 (4)−0.0148 (4)0.0101 (3)−0.0066 (3)
S20.0442 (4)0.0575 (4)0.0549 (4)−0.0057 (3)0.0064 (3)0.0094 (3)
N10.0475 (13)0.0506 (13)0.0428 (12)−0.0029 (10)0.0064 (10)−0.0014 (10)
C10.0369 (12)0.0451 (14)0.0425 (13)0.0017 (11)0.0009 (10)0.0046 (12)
C20.0555 (17)0.0498 (16)0.0543 (17)−0.0029 (14)0.0028 (14)0.0007 (14)
C30.0510 (19)0.089 (3)0.101 (3)0.0012 (19)0.0061 (19)0.044 (3)
S30.0902 (14)0.1277 (18)0.0723 (11)−0.0234 (11)0.0257 (9)0.0052 (10)
C40.046 (2)0.079 (4)0.098 (3)0.007 (3)0.009 (2)0.036 (3)
C50.103 (2)0.046 (3)0.157 (4)−0.014 (2)0.054 (3)−0.011 (3)
C60.070 (3)0.071 (4)0.119 (6)−0.005 (3)0.011 (4)0.031 (4)
C70.062 (3)0.120 (6)0.103 (7)−0.022 (3)0.011 (4)0.056 (6)
S3'0.103 (2)0.046 (3)0.157 (4)−0.014 (2)0.054 (3)−0.011 (3)
C4'0.046 (2)0.079 (4)0.098 (3)0.007 (3)0.009 (2)0.036 (3)
C5'0.0902 (14)0.1277 (18)0.0723 (11)−0.0234 (11)0.0257 (9)0.0052 (10)
C6'0.070 (3)0.071 (4)0.119 (6)−0.005 (3)0.011 (4)0.031 (4)
C7'0.062 (3)0.120 (6)0.103 (7)−0.022 (3)0.011 (4)0.056 (6)
C80.0540 (16)0.0537 (17)0.0485 (15)0.0076 (14)0.0106 (13)−0.0070 (14)
C90.0415 (13)0.0436 (14)0.0439 (14)−0.0071 (11)0.0109 (11)−0.0057 (11)
C100.0554 (17)0.0604 (18)0.0488 (16)−0.0032 (14)0.0157 (14)−0.0080 (14)
C110.071 (2)0.084 (3)0.0416 (16)−0.0063 (19)0.0158 (16)−0.0065 (16)
C120.066 (2)0.081 (2)0.0514 (18)−0.0083 (18)0.0062 (16)0.0150 (17)
C130.0651 (19)0.0493 (17)0.0624 (19)−0.0014 (15)0.0049 (16)0.0041 (15)
C140.0577 (18)0.0453 (16)0.0498 (16)−0.0026 (13)0.0062 (14)−0.0076 (12)
Geometric parameters (Å, º) top
Pb1—S1i2.6785 (9)C7—H70.9300
Pb1—S12.6785 (9)S3'—C4'1.48 (2)
Pb1—S22.8575 (9)S3'—C7'1.733 (9)
Pb1—S2i2.8576 (9)C4'—C5'1.56 (3)
S1—C11.727 (3)C5'—C6'1.446 (9)
S2—C11.709 (3)C5'—H5'0.9300
N1—C11.333 (4)C6'—C7'1.369 (9)
N1—C81.459 (4)C6'—H6'0.9300
N1—C21.478 (4)C7'—H7'0.9300
C2—C31.502 (5)C8—C91.515 (4)
C2—H2A0.9700C8—H8A0.9700
C2—H2B0.9700C8—H8B0.9700
C3—C41.471 (6)C9—C101.3900
C3—C4'1.497 (10)C9—C141.3900
C3—H3A0.9700C10—C111.3900
C3—H3B0.9700C10—H100.9300
S3—C41.622 (7)C11—C121.3900
S3—C71.728 (7)C11—H110.9300
C4—C51.389 (8)C12—C131.3900
C5—C61.449 (7)C12—H120.9300
C5—H50.9300C13—C141.3900
C6—C71.361 (7)C13—H130.9300
C6—H60.9300C14—H140.9300
S1i—Pb1—S191.64 (5)S3—C7—H7125.1
S1i—Pb1—S284.65 (2)C4'—S3'—C7'97.1 (11)
S1—Pb1—S264.63 (2)S3'—C4'—C3140 (2)
S1i—Pb1—S2i64.63 (2)S3'—C4'—C5'113.3 (10)
S1—Pb1—S2i84.65 (2)C3—C4'—C5'106.3 (15)
S2—Pb1—S2i136.04 (3)C6'—C5'—C4'107.1 (7)
C1—S1—Pb190.74 (10)C6'—C5'—H5'126.4
C1—S2—Pb185.25 (10)C4'—C5'—H5'126.4
C1—N1—C8121.5 (3)C7'—C6'—C5'111.3 (6)
C1—N1—C2122.7 (3)C7'—C6'—H6'124.3
C8—N1—C2115.5 (3)C5'—C6'—H6'124.3
N1—C1—S2121.2 (2)C6'—C7'—S3'111.1 (7)
N1—C1—S1119.7 (2)C6'—C7'—H7'124.4
S2—C1—S1119.17 (18)S3'—C7'—H7'124.4
N1—C2—C3113.0 (3)N1—C8—C9116.0 (2)
N1—C2—H2A109.0N1—C8—H8A108.3
C3—C2—H2A109.0C9—C8—H8A108.3
N1—C2—H2B109.0N1—C8—H8B108.3
C3—C2—H2B109.0C9—C8—H8B108.3
H2A—C2—H2B107.8H8A—C8—H8B107.4
C4—C3—C2113.0 (5)C10—C9—C14120.0
C4'—C3—C2108.1 (12)C10—C9—C8117.94 (16)
C4—C3—H3A109.0C14—C9—C8122.00 (16)
C2—C3—H3A109.0C11—C10—C9120.0
C4—C3—H3B109.0C11—C10—H10120.0
C2—C3—H3B109.0C9—C10—H10120.0
H3A—C3—H3B107.8C12—C11—C10120.0
C4—S3—C795.1 (3)C12—C11—H11120.0
C5—C4—C3120.9 (7)C10—C11—H11120.0
C5—C4—S3111.5 (4)C11—C12—C13120.0
C3—C4—S3127.6 (5)C11—C12—H12120.0
C4—C5—C6112.2 (5)C13—C12—H12120.0
C4—C5—H5123.9C14—C13—C12120.0
C6—C5—H5123.9C14—C13—H13120.0
C7—C6—C5111.4 (5)C12—C13—H13120.0
C7—C6—H6124.3C13—C14—C9120.0
C5—C6—H6124.3C13—C14—H14120.0
C6—C7—S3109.8 (4)C9—C14—H14120.0
C6—C7—H7125.1
C8—N1—C1—S23.1 (4)C7'—S3'—C4'—C3−169 (4)
C2—N1—C1—S2175.4 (2)C7'—S3'—C4'—C5'0.01 (16)
C8—N1—C1—S1−176.5 (2)C4—C3—C4'—S3'132 (12)
C2—N1—C1—S1−4.1 (4)C2—C3—C4'—S3'−102 (3)
Pb1—S2—C1—N1−175.3 (2)C4—C3—C4'—C5'−38 (9)
Pb1—S2—C1—S14.30 (16)C2—C3—C4'—C5'88.1 (9)
Pb1—S1—C1—N1175.0 (2)S3'—C4'—C5'—C6'0.0 (2)
Pb1—S1—C1—S2−4.57 (17)C3—C4'—C5'—C6'173 (2)
C1—N1—C2—C3110.3 (4)C4'—C5'—C6'—C7'0.0 (4)
C8—N1—C2—C3−76.9 (4)C5'—C6'—C7'—S3'0.0 (5)
N1—C2—C3—C4−175.1 (5)C4'—S3'—C7'—C6'0.0 (4)
N1—C2—C3—C4'177.4 (13)C1—N1—C8—C9−94.7 (3)
C4'—C3—C4—C5−48 (9)C2—N1—C8—C992.4 (3)
C2—C3—C4—C5−104.5 (6)N1—C8—C9—C10−159.4 (2)
C4'—C3—C4—S3129 (10)N1—C8—C9—C1423.5 (4)
C2—C3—C4—S371.9 (10)C14—C9—C10—C110.0
C7—S3—C4—C50.00 (15)C8—C9—C10—C11−177.2 (2)
C7—S3—C4—C3−176.7 (11)C9—C10—C11—C120.0
C3—C4—C5—C6177.2 (10)C10—C11—C12—C130.0
S3—C4—C5—C60.2 (2)C11—C12—C13—C140.0
C4—C5—C6—C7−0.4 (4)C12—C13—C14—C90.0
C5—C6—C7—S30.4 (4)C10—C9—C14—C130.0
C4—S3—C7—C6−0.2 (3)C8—C9—C14—C13177.1 (2)
Symmetry code: (i) −x+1, y, −z+3/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···S10.972.472.998 (4)114
C8—H8B···S20.972.532.988 (4)109
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2A···S10.972.472.998 (4)114.3
C8—H8B···S20.972.532.988 (4)108.6
 

Acknowledgements

ES is thankful to the University Grants Commission (UGC), India, for the award of a BSR–SAP research fellowship. SS acknowledges the Department of Science and Technology (DST), India, for providing computing facilities under the DST Fast-Track Scheme.

References

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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 69| Part 8| August 2013| Page m457
doi:10.1107/S1600536813019259
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