Bis{N-benzyl-N-[2-(thio-phen-2-yl)eth-yl]di-thio-carbamato-κ(2) S,S'}lead(II).

The mol-ecule of the title compound, [Pb(C14H14NS3)2], is located on a twofold rotation axis. The di-thio-carbamate anion S,S'-chelates to the Pb(II) atom, which shows a Ψ-trigonal-bipyramidal coordination. The thio-phene ring is disordered over two positions, the major component having 71.3 (7)% occupancy. The mol-ecular conformation is stabilized by intra-molecular C-H⋯S inter-actions.

Related literature

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

Experimental

Crystal data

[Pb(C14H14NS3)2]

M = 792.07

Monoclinic,

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 ▶) T min = 0.699, T max = 0.707

16187 measured reflections

3487 independent reflections

3089 reflections with I > 2σ(I)

R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 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

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 and PLATON (Spek, 2009) ▶.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813019259/ng5336sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Pb(C14H14NS3)2]	F(000) = 1552
Mr = 792.07	Dx = 1.799 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 27.459 (2) Å	Cell parameters from 8428 reflections
b = 5.5580 (4) Å	θ = 2.5–27.6°
c = 19.4670 (15) Å	µ = 6.22 mm−1
β = 100.168 (2)°	T = 292 K
V = 2924.3 (4) Å3	Needle, yellow
Z = 4	0.20 × 0.08 × 0.06 mm

Bruker SMART APEX CCD area-detector diffractometer	3089 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.023
ω scans	θmax = 28.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −35→35
Tmin = 0.699, Tmax = 0.707	k = −7→7
16187 measured reflections	l = −25→25
3487 independent reflections

Refinement on F2	23 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.026	H-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 reflections	Δρmax = 0.91 e Å−3
172 parameters	Δρmin = −0.84 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Pb1	0.5000	1.14399 (3)	0.7500	0.06000 (9)
S1	0.42993 (3)	0.80812 (17)	0.71606 (4)	0.0567 (2)
S2	0.49150 (3)	0.95155 (16)	0.61228 (4)	0.05250 (18)
N1	0.42564 (10)	0.5970 (5)	0.59289 (13)	0.0471 (5)
C1	0.44701 (10)	0.7691 (6)	0.63555 (14)	0.0422 (5)
C2	0.38975 (13)	0.4246 (6)	0.61323 (18)	0.0540 (7)
H2A	0.3901	0.4389	0.6630	0.065*
H2B	0.4000	0.2623	0.6042	0.065*
C3	0.33791 (14)	0.4638 (10)	0.5748 (3)	0.0812 (13)
H3A	0.3287	0.6302	0.5805	0.097*
H3B	0.3370	0.4356	0.5255	0.097*
S3	0.28129 (10)	0.3223 (5)	0.67259 (11)	0.0953 (8)	0.713 (7)
C4	0.3015 (4)	0.3061 (14)	0.5993 (4)	0.0749 (18)	0.713 (7)
C5	0.2819 (4)	0.1084 (14)	0.5602 (4)	0.098 (2)	0.713 (7)
H5	0.2893	0.0692	0.5168	0.118*	0.713 (7)
C6	0.2487 (2)	−0.0298 (10)	0.5950 (4)	0.087 (2)	0.713 (7)
H6	0.2320	−0.1674	0.5766	0.105*	0.713 (7)
C7	0.2449 (3)	0.0673 (15)	0.6581 (4)	0.096 (3)	0.713 (7)
H7	0.2256	0.0057	0.6887	0.115*	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'	0.2978	0.5133	0.6868	0.114*	0.287 (7)
C6'	0.2511 (6)	0.204 (3)	0.6800 (6)	0.087 (2)	0.287 (7)
H6'	0.2344	0.2224	0.7174	0.105*	0.287 (7)
C7'	0.2443 (6)	0.015 (3)	0.6342 (9)	0.096 (3)	0.287 (7)
H7'	0.2226	−0.1114	0.6364	0.115*	0.287 (7)
C8	0.44094 (12)	0.5488 (6)	0.52616 (16)	0.0519 (7)
H8A	0.4392	0.3766	0.5180	0.062*
H8B	0.4753	0.5963	0.5298	0.062*
C9	0.41122 (7)	0.6731 (3)	0.46313 (8)	0.0426 (6)
C10	0.41287 (8)	0.5775 (3)	0.39761 (10)	0.0541 (7)
H10	0.4307	0.4373	0.3936	0.065*
C11	0.38794 (9)	0.6913 (4)	0.33807 (8)	0.0647 (9)
H11	0.3890	0.6273	0.2942	0.078*
C12	0.36135 (9)	0.9008 (4)	0.34405 (9)	0.0665 (9)
H12	0.3447	0.9769	0.3042	0.080*
C13	0.35970 (8)	0.9964 (3)	0.40957 (11)	0.0597 (8)
H13	0.3419	1.1366	0.4136	0.072*
C14	0.38463 (8)	0.8826 (3)	0.46911 (8)	0.0513 (7)
H14	0.3835	0.9466	0.5129	0.062*

	U11	U22	U33	U12	U13	U23
Pb1	0.06332 (13)	0.04215 (11)	0.06445 (13)	0.000	−0.01642 (8)	0.000
S1	0.0622 (5)	0.0666 (5)	0.0418 (4)	−0.0148 (4)	0.0101 (3)	−0.0066 (3)
S2	0.0442 (4)	0.0575 (4)	0.0549 (4)	−0.0057 (3)	0.0064 (3)	0.0094 (3)
N1	0.0475 (13)	0.0506 (13)	0.0428 (12)	−0.0029 (10)	0.0064 (10)	−0.0014 (10)
C1	0.0369 (12)	0.0451 (14)	0.0425 (13)	0.0017 (11)	0.0009 (10)	0.0046 (12)
C2	0.0555 (17)	0.0498 (16)	0.0543 (17)	−0.0029 (14)	0.0028 (14)	0.0007 (14)
C3	0.0510 (19)	0.089 (3)	0.101 (3)	0.0012 (19)	0.0061 (19)	0.044 (3)
S3	0.0902 (14)	0.1277 (18)	0.0723 (11)	−0.0234 (11)	0.0257 (9)	0.0052 (10)
C4	0.046 (2)	0.079 (4)	0.098 (3)	0.007 (3)	0.009 (2)	0.036 (3)
C5	0.103 (2)	0.046 (3)	0.157 (4)	−0.014 (2)	0.054 (3)	−0.011 (3)
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)
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)
C8	0.0540 (16)	0.0537 (17)	0.0485 (15)	0.0076 (14)	0.0106 (13)	−0.0070 (14)
C9	0.0415 (13)	0.0436 (14)	0.0439 (14)	−0.0071 (11)	0.0109 (11)	−0.0057 (11)
C10	0.0554 (17)	0.0604 (18)	0.0488 (16)	−0.0032 (14)	0.0157 (14)	−0.0080 (14)
C11	0.071 (2)	0.084 (3)	0.0416 (16)	−0.0063 (19)	0.0158 (16)	−0.0065 (16)
C12	0.066 (2)	0.081 (2)	0.0514 (18)	−0.0083 (18)	0.0062 (16)	0.0150 (17)
C13	0.0651 (19)	0.0493 (17)	0.0624 (19)	−0.0014 (15)	0.0049 (16)	0.0041 (15)
C14	0.0577 (18)	0.0453 (16)	0.0498 (16)	−0.0026 (13)	0.0062 (14)	−0.0076 (12)

Pb1—S1i	2.6785 (9)	C7—H7	0.9300
Pb1—S1	2.6785 (9)	S3'—C4'	1.48 (2)
Pb1—S2	2.8575 (9)	S3'—C7'	1.733 (9)
Pb1—S2i	2.8576 (9)	C4'—C5'	1.56 (3)
S1—C1	1.727 (3)	C5'—C6'	1.446 (9)
S2—C1	1.709 (3)	C5'—H5'	0.9300
N1—C1	1.333 (4)	C6'—C7'	1.369 (9)
N1—C8	1.459 (4)	C6'—H6'	0.9300
N1—C2	1.478 (4)	C7'—H7'	0.9300
C2—C3	1.502 (5)	C8—C9	1.515 (4)
C2—H2A	0.9700	C8—H8A	0.9700
C2—H2B	0.9700	C8—H8B	0.9700
C3—C4	1.471 (6)	C9—C10	1.3900
C3—C4'	1.497 (10)	C9—C14	1.3900
C3—H3A	0.9700	C10—C11	1.3900
C3—H3B	0.9700	C10—H10	0.9300
S3—C4	1.622 (7)	C11—C12	1.3900
S3—C7	1.728 (7)	C11—H11	0.9300
C4—C5	1.389 (8)	C12—C13	1.3900
C5—C6	1.449 (7)	C12—H12	0.9300
C5—H5	0.9300	C13—C14	1.3900
C6—C7	1.361 (7)	C13—H13	0.9300
C6—H6	0.9300	C14—H14	0.9300
S1i—Pb1—S1	91.64 (5)	S3—C7—H7	125.1
S1i—Pb1—S2	84.65 (2)	C4'—S3'—C7'	97.1 (11)
S1—Pb1—S2	64.63 (2)	S3'—C4'—C3	140 (2)
S1i—Pb1—S2i	64.63 (2)	S3'—C4'—C5'	113.3 (10)
S1—Pb1—S2i	84.65 (2)	C3—C4'—C5'	106.3 (15)
S2—Pb1—S2i	136.04 (3)	C6'—C5'—C4'	107.1 (7)
C1—S1—Pb1	90.74 (10)	C6'—C5'—H5'	126.4
C1—S2—Pb1	85.25 (10)	C4'—C5'—H5'	126.4
C1—N1—C8	121.5 (3)	C7'—C6'—C5'	111.3 (6)
C1—N1—C2	122.7 (3)	C7'—C6'—H6'	124.3
C8—N1—C2	115.5 (3)	C5'—C6'—H6'	124.3
N1—C1—S2	121.2 (2)	C6'—C7'—S3'	111.1 (7)
N1—C1—S1	119.7 (2)	C6'—C7'—H7'	124.4
S2—C1—S1	119.17 (18)	S3'—C7'—H7'	124.4
N1—C2—C3	113.0 (3)	N1—C8—C9	116.0 (2)
N1—C2—H2A	109.0	N1—C8—H8A	108.3
C3—C2—H2A	109.0	C9—C8—H8A	108.3
N1—C2—H2B	109.0	N1—C8—H8B	108.3
C3—C2—H2B	109.0	C9—C8—H8B	108.3
H2A—C2—H2B	107.8	H8A—C8—H8B	107.4
C4—C3—C2	113.0 (5)	C10—C9—C14	120.0
C4'—C3—C2	108.1 (12)	C10—C9—C8	117.94 (16)
C4—C3—H3A	109.0	C14—C9—C8	122.00 (16)
C2—C3—H3A	109.0	C11—C10—C9	120.0
C4—C3—H3B	109.0	C11—C10—H10	120.0
C2—C3—H3B	109.0	C9—C10—H10	120.0
H3A—C3—H3B	107.8	C12—C11—C10	120.0
C4—S3—C7	95.1 (3)	C12—C11—H11	120.0
C5—C4—C3	120.9 (7)	C10—C11—H11	120.0
C5—C4—S3	111.5 (4)	C11—C12—C13	120.0
C3—C4—S3	127.6 (5)	C11—C12—H12	120.0
C4—C5—C6	112.2 (5)	C13—C12—H12	120.0
C4—C5—H5	123.9	C14—C13—C12	120.0
C6—C5—H5	123.9	C14—C13—H13	120.0
C7—C6—C5	111.4 (5)	C12—C13—H13	120.0
C7—C6—H6	124.3	C13—C14—C9	120.0
C5—C6—H6	124.3	C13—C14—H14	120.0
C6—C7—S3	109.8 (4)	C9—C14—H14	120.0
C6—C7—H7	125.1
C8—N1—C1—S2	3.1 (4)	C7'—S3'—C4'—C3	−169 (4)
C2—N1—C1—S2	175.4 (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—S1	4.30 (16)	C2—C3—C4'—C5'	88.1 (9)
Pb1—S1—C1—N1	175.0 (2)	S3'—C4'—C5'—C6'	0.0 (2)
Pb1—S1—C1—S2	−4.57 (17)	C3—C4'—C5'—C6'	173 (2)
C1—N1—C2—C3	110.3 (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—C9	92.4 (3)
C2—C3—C4—C5	−104.5 (6)	N1—C8—C9—C10	−159.4 (2)
C4'—C3—C4—S3	129 (10)	N1—C8—C9—C14	23.5 (4)
C2—C3—C4—S3	71.9 (10)	C14—C9—C10—C11	0.0
C7—S3—C4—C5	0.00 (15)	C8—C9—C10—C11	−177.2 (2)
C7—S3—C4—C3	−176.7 (11)	C9—C10—C11—C12	0.0
C3—C4—C5—C6	177.2 (10)	C10—C11—C12—C13	0.0
S3—C4—C5—C6	0.2 (2)	C11—C12—C13—C14	0.0
C4—C5—C6—C7	−0.4 (4)	C12—C13—C14—C9	0.0
C5—C6—C7—S3	0.4 (4)	C10—C9—C14—C13	0.0
C4—S3—C7—C6	−0.2 (3)	C8—C9—C14—C13	177.1 (2)

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

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