cis-Di­chloro­tetrakis(2-mercapto-1-tert-butyl­imidazole)­lead(II)

Evans, R.N.; Mihalcik, D.J.; Jones, D.S.; Rabinovich, D.

doi:10.1107/S160053680301064X

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cis-Dichlorotetrakis(2-mercapto-1-tert-butylimidazole)lead(II)

R. N. Evans, D. J. Mihalcik, D. S. Jones and D. Rabinovich

The crystal and molecular structure of the title compound, [PbCl₂(C₇H₁₂N₂S)₄], the first mononuclear lead complex containing a 2-mercapto-1-alkylimidazole ligand to be structurally characterized, has been determined by single-crystal X-ray diffraction. The six-coordinate Pb atom displays a distorted octahedral geometry and is surrounded by four thione groups and two cis chloro ligands, with average Pb-S and Pb-Cl bond distances of 2.946 (3) and 3.058 (2) Å, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301064X/ac6039sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301064X/ac6039Isup2.hkl Contains datablock I

CCDC reference: 214792

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.011 Å
R factor = 0.047
wR factor = 0.130
Data-to-parameter ratio = 17.0

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No syntax errors found

ADDSYM reports no extra symmetry

Comment top

The coordination chemistry of lead with sulfur-donor ligands is surprisingly underdeveloped despite the purported thiophilicity of this metal. According to a recent survey, only about 16% of all Pb^II compounds in the Cambridge Structural Database (CSD; Version 5.24, November 2002; Allen, 2002) contain one or more sulfur-donor groups (Claudio et al., 2003). Heterocyclic thione and thionate ligands are no exception, and very few derivatives of lead have been isolated with such donors despite the large number of complexes obtained with them for both transition and main group metals (Raper, 1985; Akrivos, 2001). In view of this imbalance and because of our interest in the coordination chemistry of lead with simple thione-type donor ligands, we set out to prepare new complexes with N-substituted mercaptoimidazoles. We report here the synthesis, characterization and structure of cis-dichlorotetrakis(2-mercapto-1-tert-butylimidazole)lead(II), (I), the first mononuclear lead complex containing a 2-mercapto-1-alkylimidazole ligand.

The crystal and molecular structure of (I) was determined by single-crystal X-ray diffraction (Fig. 1). The Pb atom in cis-Pb(Hmim^tBu)₄Cl₂ is coordinated to the thione moieties of four mercaptoimidazole groups and to two adjacent chloro ligands in a distorted octahedral environment, with the trans and cis angles in the approximate ranges 154–170 and 82–112°, respectively. The two Pb—S distances to the thione ligands trans to the chlorides (ca 2.89 Å) are slightly shorter than those for the mutually trans thiones (ca 3.00 Å). While these values are only moderately longer than the corresponding bond lengths to the terminal methimazole groups in the dinuclear derivative Pb₂(Hmim^Me)₆(NO₃)₄ (ca 2.84 Å; Bristow et al., 1987), they are comparable to those found in other Pb^II complexes with thioureas or heterocyclic thiones (Goldberg & Herbstein, 1972; Herbstein & Kaftory, 1972; Williams et al., 1992). It is also interesting to note that the average C—S bond length in cis-Pb(Hmim^tBu)₄Cl₂ (ca 1.71 Å) is very similar to the corresponding averages found for the group 12 metal derivatives (Hmim^tBu)₄MBr₂ (M = Zn, Cd, Hg) (ca 1.72 Å) or even in free Hmim^tBu (1.70 Å; White et al., 2003). The Pb—Cl bond lengths, 3.037 (2) and 3.079 (2) Å, while longer than the mean value found in the CSD for such terminal interactions in six-coordinate Pb^II (2.87 Å), are still within the range of observed distances for such bonds (2.617–3.348 Å; Allen & Kennard, 1993).

Experimental top

A solution of 2-mercapto-1-tert-butylimidazole (0.150 g, 0.960 mmol) in methanol (1 ml) was added to a stirred solution of PbCl₂ (0.067 g, 0.240 mmol) in water (5 ml), resulting in the immediate formation of an off-white precipitate and a pale yellow solution. After stirring the suspension for 30 min, the product was isolated by filtration and dried in vacuo for 14 h (0.126 g, 58%). NMR data (in CD₂Cl₂): ¹H δ 1.74 [s, 36H, C(CH₃)₃], 6.72 (d, ³J_H–H = 2.3 Hz, 4H, imidazole H), 6.84 (d, ³J_H–H = 2.3 Hz, 4H, imidazole H), 11.91 (br s, 4H, NH); ¹³C d 28.5 [q, ¹J_C–H = 128 Hz, 12 C, C(CH₃)₃], 59.1 [s, 4 C, C(CH₃)₃], 114.2 (d, ¹J_C—H = 176 Hz, 4 C, imidazole C), 116.3 (d, ¹J_C–H = 167 Hz, 4 C, imidazole C), 156.8 (s, 4 C, C═S). IR data (cm⁻¹): 3137 (m), 3096 (s), 3015 (m), 2974 (s), 2917 (m), 2884 (m), 2782 (w), 2729 (w), 1576 (s), 1474 (s), 1455 (m), 1414 (m), 1399 (m), 1369 (m), 1312 (versus), 1264 (w), 1238 (versus), 1225 (s), 1178 (w), 1126 (m), 1118 (m), 1043 (w), 1014 (w), 935 (w), 913 (w), 795 (m), 768 (w), 723 (m), 684 (s), 591 (w), 546 (m), 458 (w). Analysis calculated for C₂₈H₄₈Cl₂N₈PbS₄: C 37.2, H 5.4, N 12.4%; found: C 37.5, H 5.2, N 12.5%.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. A view of the title compound, showing 30% probability ellipsoids. H atoms have been obmitted for clarity.
	Fig. 2. A packing diagram of the title compound, viewed down the a axis.

cis-Dichlorotetrakis(2-mercapto-1-tert-butylimidazole)lead(II) top

Crystal data top

[PbCl₂(C₇H₁₂N₂S)₄]	F(000) = 1808
M_r = 903.07	D_x = 1.543 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 155 K
Hall symbol: -P 2ybc	Cu Kα radiation, λ = 1.5418 Å
a = 10.2683 (11) Å	Cell parameters from 25 reflections
b = 10.9843 (13) Å	θ = 11.0–20.8°
c = 34.514 (4) Å	µ = 11.97 mm⁻¹
β = 93.294 (9)°	T = 293 K
V = 3886.4 (8) Å³	Irregular, yellow
Z = 4	0.40 × 0.29 × 0.17 mm

Data collection top

Enraf-Nonius CAD-4 diffractometer	5838 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	R_int = 0.051
Graphite monochromator	θ_max = 66.9°, θ_min = 2.6°
non–profiled ω/2θ scans	h = −12→12
Absorption correction: analytical (Katayama, 1986)	k = 0→13
T_min = 0.048, T_max = 0.214	l = −34→41
10879 measured reflections	3 standard reflections every 60 min
6878 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.130	w = 1/[σ²(F_o²) + (0.0906P)² + 2.6577P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.001
6878 reflections	Δρ_max = 1.68 e Å⁻³
404 parameters	Δρ_min = −1.50 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00190 (9)

Crystal data top

[PbCl₂(C₇H₁₂N₂S)₄]	V = 3886.4 (8) Å³
M_r = 903.07	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 10.2683 (11) Å	µ = 11.97 mm⁻¹
b = 10.9843 (13) Å	T = 293 K
c = 34.514 (4) Å	0.40 × 0.29 × 0.17 mm
β = 93.294 (9)°

Data collection top

Enraf-Nonius CAD-4 diffractometer	5838 reflections with I > 2σ(I)
Absorption correction: analytical (Katayama, 1986)	R_int = 0.051
T_min = 0.048, T_max = 0.214	3 standard reflections every 60 min
10879 measured reflections	intensity decay: none
6878 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.130	H-atom parameters constrained
S = 1.03	Δρ_max = 1.68 e Å⁻³
6878 reflections	Δρ_min = −1.50 e Å⁻³
404 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	0.275402 (19)	0.415611 (19)	0.120267 (6)	0.04968 (13)
Cl1	0.47136 (16)	0.24054 (15)	0.08822 (6)	0.0708 (4)
Cl2	0.07031 (18)	0.36497 (17)	0.05362 (5)	0.0702 (4)
S11	0.10801 (15)	0.29085 (17)	0.17993 (5)	0.0656 (4)
C11	−0.0355 (6)	0.2407 (5)	0.15933 (16)	0.0513 (12)
N12	−0.1413 (4)	0.1922 (4)	0.17545 (14)	0.0541 (11)
C12	−0.1592 (6)	0.1763 (6)	0.21807 (19)	0.0628 (15)
C12A	−0.1471 (9)	0.2995 (7)	0.2377 (2)	0.086 (2)
H12A	−0.2157	0.352	0.2276	0.094 (5)*
H12B	−0.0641	0.3349	0.2328	0.094 (5)*
H12C	−0.1538	0.2898	0.2651	0.094 (5)*
C12B	−0.2966 (8)	0.1274 (9)	0.2225 (3)	0.093 (3)
H12D	−0.3593	0.1879	0.2139	0.094 (5)*
H12E	−0.3076	0.1085	0.2493	0.094 (5)*
H12F	−0.3094	0.0552	0.2071	0.094 (5)*
C12C	−0.0605 (8)	0.0856 (6)	0.2347 (2)	0.0739 (19)
H12G	−0.0694	0.0778	0.2621	0.094 (5)*
H12H	0.0259	0.1134	0.2301	0.094 (5)*
H12I	−0.0753	0.008	0.2224	0.094 (5)*
C13	−0.2329 (6)	0.1596 (6)	0.1461 (2)	0.0652 (16)
H13	−0.3132	0.1232	0.1496	0.096 (10)*
C14	−0.1861 (7)	0.1895 (7)	0.1122 (2)	0.0661 (16)
H14	−0.2278	0.1794	0.0878	0.096 (10)*
N15	−0.0644 (5)	0.2381 (5)	0.12027 (14)	0.0563 (11)
H15	−0.0134	0.2634	0.1031	0.073 (11)*
S21	0.41821 (16)	0.62131 (15)	0.08922 (5)	0.0630 (4)
C21	0.5368 (6)	0.5890 (5)	0.05808 (18)	0.0527 (13)
N22	0.6157 (5)	0.6656 (5)	0.04006 (15)	0.0607 (12)
C22	0.6187 (7)	0.8013 (7)	0.0433 (2)	0.0704 (17)
C22A	0.7190 (9)	0.8523 (9)	0.0162 (3)	0.100 (3)
H22A	0.8042	0.8221	0.0241	0.094 (5)*
H22B	0.7191	0.9396	0.0175	0.094 (5)*
H22C	0.6965	0.8269	−0.01	0.094 (5)*
C22B	0.6584 (10)	0.8339 (9)	0.0850 (3)	0.094 (3)
H22D	0.5945	0.8032	0.1018	0.094 (5)*
H22E	0.6639	0.9208	0.0876	0.094 (5)*
H22F	0.7418	0.7984	0.0921	0.094 (5)*
C22C	0.4856 (8)	0.8519 (8)	0.0307 (3)	0.088 (2)
H22G	0.4671	0.8351	0.0036	0.094 (5)*
H22H	0.4849	0.9383	0.0348	0.094 (5)*
H22I	0.4204	0.8144	0.0456	0.094 (5)*
C23	0.6992 (8)	0.5977 (8)	0.0185 (2)	0.079 (2)
H23	0.764	0.6287	0.0035	0.096 (10)*
C24	0.6701 (8)	0.4789 (9)	0.0229 (2)	0.078 (2)
H24	0.7099	0.4127	0.0117	0.096 (10)*
N25	0.5700 (5)	0.4760 (5)	0.04733 (16)	0.0620 (12)
H25	0.533	0.4105	0.0548	0.073 (11)*
S31	0.43764 (16)	0.44040 (16)	0.19034 (5)	0.0622 (4)
C31	0.5808 (5)	0.4869 (5)	0.17185 (16)	0.0512 (12)
N32	0.6627 (5)	0.5802 (4)	0.18264 (15)	0.0529 (11)
C32	0.6423 (6)	0.6735 (6)	0.21346 (18)	0.0589 (14)
C32A	0.5161 (7)	0.7427 (7)	0.2027 (2)	0.0693 (17)
H32A	0.5265	0.7892	0.1795	0.094 (5)*
H32B	0.4967	0.7966	0.2234	0.094 (5)*
H32C	0.4458	0.6858	0.1982	0.094 (5)*
C32B	0.6390 (8)	0.6091 (7)	0.2522 (2)	0.0690 (17)
H32D	0.57	0.5499	0.2511	0.094 (5)*
H32E	0.6239	0.6675	0.2722	0.094 (5)*
H32F	0.7208	0.5689	0.258	0.094 (5)*
C32C	0.7564 (8)	0.7635 (7)	0.2148 (2)	0.0753 (19)
H32G	0.8369	0.7199	0.2193	0.094 (5)*
H32H	0.7465	0.8209	0.2354	0.094 (5)*
H32I	0.7572	0.8061	0.1905	0.094 (5)*
C33	0.7672 (6)	0.5780 (6)	0.1591 (2)	0.0617 (15)
H33	0.8369	0.6323	0.1602	0.096 (10)*
C34	0.7511 (6)	0.4854 (6)	0.1345 (2)	0.0646 (15)
H34	0.8066	0.4632	0.1153	0.096 (10)*
N35	0.6365 (5)	0.4286 (4)	0.14295 (16)	0.0599 (13)
H35	0.6051	0.3648	0.1313	0.073 (11)*
S41	0.1170 (2)	0.62401 (18)	0.13937 (6)	0.0732 (5)
C41	0.1089 (5)	0.7028 (6)	0.09631 (18)	0.0563 (13)
N42	0.1317 (5)	0.8226 (5)	0.08930 (14)	0.0549 (11)
C42	0.1618 (7)	0.9208 (6)	0.1187 (2)	0.0640 (16)
C42A	0.0488 (9)	0.9321 (7)	0.1448 (3)	0.083 (2)
H42A	−0.0295	0.9508	0.1293	0.094 (5)*
H42B	0.0665	0.996	0.1633	0.094 (5)*
H42C	0.0376	0.8566	0.1582	0.094 (5)*
C42B	0.2873 (9)	0.8913 (8)	0.1418 (3)	0.087 (2)
H42D	0.2777	0.8156	0.1552	0.094 (5)*
H42E	0.3067	0.955	0.1603	0.094 (5)*
H42F	0.357	0.8845	0.1246	0.094 (5)*
C42C	0.1768 (9)	1.0427 (7)	0.0973 (3)	0.086 (2)
H42G	0.1026	1.0553	0.0796	0.094 (5)*
H42H	0.2547	1.0408	0.0832	0.094 (5)*
H42I	0.1825	1.1079	0.1158	0.094 (5)*
C43	0.1163 (7)	0.8402 (8)	0.0497 (2)	0.0741 (18)
H43	0.127	0.9138	0.0369	0.096 (10)*
C44	0.0838 (7)	0.7358 (8)	0.0328 (2)	0.078 (2)
H44	0.0673	0.722	0.0064	0.096 (10)*
N45	0.0796 (5)	0.6524 (6)	0.06178 (17)	0.0703 (15)
H45	0.0604	0.5768	0.0583	0.073 (11)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.04515 (17)	0.04777 (17)	0.05645 (18)	−0.00382 (8)	0.00574 (10)	−0.00037 (8)
Cl1	0.0649 (9)	0.0560 (8)	0.0910 (11)	−0.0060 (7)	0.0010 (8)	−0.0084 (8)
Cl2	0.0824 (10)	0.0735 (10)	0.0550 (8)	−0.0150 (8)	0.0060 (7)	−0.0033 (7)
S11	0.0577 (8)	0.0785 (10)	0.0606 (8)	−0.0171 (7)	0.0027 (7)	0.0101 (7)
C11	0.054 (3)	0.047 (3)	0.053 (3)	0.003 (2)	0.011 (2)	0.003 (2)
N12	0.053 (3)	0.045 (2)	0.066 (3)	0.004 (2)	0.016 (2)	0.002 (2)
C12	0.065 (4)	0.055 (3)	0.071 (4)	0.001 (3)	0.029 (3)	0.003 (3)
C12A	0.119 (6)	0.064 (4)	0.080 (5)	0.007 (4)	0.043 (5)	−0.004 (4)
C12B	0.066 (4)	0.103 (6)	0.112 (7)	−0.008 (4)	0.040 (4)	0.017 (5)
C12C	0.083 (5)	0.066 (4)	0.074 (4)	0.007 (3)	0.017 (4)	0.014 (3)
C13	0.049 (3)	0.056 (3)	0.090 (5)	0.001 (3)	0.004 (3)	−0.007 (3)
C14	0.060 (3)	0.063 (4)	0.074 (4)	0.007 (3)	−0.005 (3)	−0.010 (3)
N15	0.048 (2)	0.063 (3)	0.058 (3)	0.005 (2)	0.004 (2)	−0.001 (2)
S21	0.0621 (9)	0.0523 (7)	0.0775 (10)	0.0040 (7)	0.0293 (7)	0.0078 (7)
C21	0.049 (3)	0.054 (3)	0.056 (3)	0.001 (2)	0.010 (2)	0.003 (2)
N22	0.053 (3)	0.064 (3)	0.066 (3)	0.002 (2)	0.015 (2)	0.009 (2)
C22	0.065 (4)	0.066 (4)	0.082 (4)	−0.007 (3)	0.016 (3)	0.015 (3)
C22A	0.094 (6)	0.094 (6)	0.115 (7)	−0.019 (5)	0.040 (5)	0.024 (5)
C22B	0.110 (7)	0.077 (5)	0.097 (6)	−0.026 (5)	0.001 (5)	−0.001 (4)
C22C	0.092 (5)	0.070 (5)	0.104 (6)	0.008 (4)	0.020 (5)	0.027 (4)
C23	0.064 (4)	0.100 (6)	0.076 (5)	0.007 (4)	0.028 (4)	0.008 (4)
C24	0.078 (5)	0.093 (6)	0.064 (4)	0.019 (4)	0.024 (3)	−0.004 (4)
N25	0.063 (3)	0.061 (3)	0.064 (3)	0.002 (3)	0.017 (2)	0.001 (2)
S31	0.0584 (8)	0.0706 (9)	0.0578 (8)	−0.0151 (7)	0.0056 (6)	0.0021 (7)
C31	0.052 (3)	0.047 (3)	0.055 (3)	0.001 (2)	−0.001 (2)	0.003 (2)
N32	0.047 (2)	0.050 (3)	0.061 (3)	−0.0007 (19)	0.001 (2)	−0.003 (2)
C32	0.060 (3)	0.054 (3)	0.062 (3)	−0.003 (3)	−0.004 (3)	0.000 (3)
C32A	0.075 (4)	0.061 (4)	0.071 (4)	0.014 (3)	−0.002 (3)	−0.004 (3)
C32B	0.078 (4)	0.069 (4)	0.059 (4)	−0.003 (3)	−0.006 (3)	−0.004 (3)
C32C	0.082 (5)	0.063 (4)	0.079 (4)	−0.018 (4)	−0.010 (4)	−0.004 (3)
C33	0.046 (3)	0.060 (4)	0.079 (4)	−0.001 (3)	0.007 (3)	0.003 (3)
C34	0.051 (3)	0.063 (4)	0.081 (4)	0.006 (3)	0.012 (3)	−0.004 (3)
N35	0.062 (3)	0.050 (3)	0.067 (3)	0.002 (2)	0.007 (2)	−0.010 (2)
S41	0.0808 (11)	0.0669 (10)	0.0744 (10)	0.0154 (9)	0.0275 (9)	0.0098 (8)
C41	0.046 (3)	0.062 (3)	0.061 (3)	0.000 (3)	0.003 (2)	−0.006 (3)
N42	0.052 (2)	0.052 (3)	0.061 (3)	0.011 (2)	0.005 (2)	0.003 (2)
C42	0.058 (4)	0.054 (3)	0.081 (4)	0.006 (3)	0.007 (3)	−0.013 (3)
C42A	0.096 (6)	0.062 (4)	0.093 (5)	0.019 (4)	0.035 (5)	−0.009 (4)
C42B	0.087 (5)	0.081 (5)	0.090 (6)	0.014 (4)	−0.017 (4)	−0.024 (4)
C42C	0.091 (5)	0.052 (4)	0.116 (7)	−0.007 (4)	0.016 (5)	0.003 (4)
C43	0.076 (4)	0.080 (5)	0.066 (4)	0.013 (4)	−0.003 (3)	0.011 (4)
C44	0.076 (4)	0.088 (5)	0.070 (4)	0.012 (4)	−0.012 (3)	0.004 (4)
N45	0.059 (3)	0.071 (4)	0.081 (4)	−0.001 (3)	−0.001 (3)	−0.016 (3)

Geometric parameters (Å, º) top

Pb1—S31	2.8698 (16)	C24—N25	1.366 (9)
Pb1—S41	2.9057 (19)	C24—H24	0.93
Pb1—S21	2.9299 (16)	N25—H25	0.86
Pb1—Cl1	3.0374 (18)	S31—C31	1.714 (6)
Pb1—Cl2	3.0787 (17)	C31—N35	1.341 (8)
Pb1—S11	3.0790 (16)	C31—N32	1.364 (7)
S11—C11	1.691 (6)	N32—C33	1.384 (8)
C11—N12	1.358 (7)	N32—C32	1.500 (8)
C11—N15	1.364 (7)	C32—C32B	1.516 (9)
N12—C13	1.388 (8)	C32—C32C	1.531 (9)
N12—C12	1.503 (8)	C32—C32A	1.531 (9)
C12—C12C	1.511 (9)	C32A—H32A	0.96
C12—C12A	1.515 (10)	C32A—H32B	0.96
C12—C12B	1.526 (9)	C32A—H32C	0.96
C12A—H12A	0.96	C32B—H32D	0.96
C12A—H12B	0.96	C32B—H32E	0.96
C12A—H12C	0.96	C32B—H32F	0.96
C12B—H12D	0.96	C32C—H32G	0.96
C12B—H12E	0.96	C32C—H32H	0.96
C12B—H12F	0.96	C32C—H32I	0.96
C12C—H12G	0.96	C33—C34	1.328 (9)
C12C—H12H	0.96	C33—H33	0.93
C12C—H12I	0.96	C34—N35	1.379 (8)
C13—C14	1.333 (10)	C34—H34	0.93
C13—H13	0.93	N35—H35	0.86
C14—N15	1.373 (8)	S41—C41	1.717 (7)
C14—H14	0.93	C41—N45	1.333 (8)
N15—H15	0.86	C41—N42	1.361 (8)
S21—C21	1.707 (6)	N42—C43	1.381 (8)
C21—N22	1.344 (8)	N42—C42	1.500 (8)
C21—N25	1.345 (8)	C42—C42B	1.511 (10)
N22—C23	1.386 (9)	C42—C42A	1.515 (10)
N22—C22	1.496 (9)	C42—C42C	1.540 (10)
C22—C22C	1.517 (10)	C42A—H42A	0.96
C22—C22B	1.516 (11)	C42A—H42B	0.96
C22—C22A	1.537 (10)	C42A—H42C	0.96
C22A—H22A	0.96	C42B—H42D	0.96
C22A—H22B	0.96	C42B—H42E	0.96
C22A—H22C	0.96	C42B—H42F	0.96
C22B—H22D	0.96	C42C—H42G	0.96
C22B—H22E	0.96	C42C—H42H	0.96
C22B—H22F	0.96	C42C—H42I	0.96
C22C—H22G	0.96	C43—C44	1.321 (11)
C22C—H22H	0.96	C43—H43	0.93
C22C—H22I	0.96	C44—N45	1.359 (10)
C23—C24	1.350 (11)	C44—H44	0.93
C23—H23	0.93	N45—H45	0.86

S31—Pb1—S41	92.26 (6)	N22—C23—H23	126
S31—Pb1—S21	87.51 (5)	C23—C24—N25	105.9 (7)
S41—Pb1—S21	76.93 (5)	C23—C24—H24	127.1
S31—Pb1—Cl1	90.14 (5)	N25—C24—H24	127.1
S41—Pb1—Cl1	166.54 (5)	C21—N25—C24	111.1 (6)
S21—Pb1—Cl1	89.95 (5)	C21—N25—H25	124.5
S31—Pb1—Cl2	170.34 (5)	C24—N25—H25	124.5
S41—Pb1—Cl2	86.79 (6)	C31—S31—Pb1	100.6 (2)
S21—Pb1—Cl2	101.62 (5)	N35—C31—N32	106.3 (5)
Cl1—Pb1—Cl2	93.01 (5)	N35—C31—S31	123.1 (4)
S31—Pb1—S11	78.34 (4)	N32—C31—S31	130.6 (5)
S41—Pb1—S11	81.82 (5)	C31—N32—C33	108.3 (5)
S21—Pb1—S11	153.93 (5)	C31—N32—C32	126.8 (5)
Cl1—Pb1—S11	111.64 (5)	C33—N32—C32	124.9 (5)
Cl2—Pb1—S11	92.01 (4)	N32—C32—C32B	108.5 (5)
C11—S11—Pb1	111.7 (2)	N32—C32—C32C	109.0 (5)
N12—C11—N15	105.3 (5)	C32B—C32—C32C	109.3 (5)
N12—C11—S11	130.8 (5)	N32—C32—C32A	108.5 (5)
N15—C11—S11	123.9 (4)	C32B—C32—C32A	112.7 (6)
C11—N12—C13	109.1 (5)	C32C—C32—C32A	108.8 (6)
C11—N12—C12	126.3 (5)	C32—C32A—H32A	109.5
C13—N12—C12	124.6 (5)	C32—C32A—H32B	109.5
N12—C12—C12C	109.3 (5)	H32A—C32A—H32B	109.5
N12—C12—C12A	108.8 (5)	C32—C32A—H32C	109.5
C12C—C12—C12A	112.6 (7)	H32A—C32A—H32C	109.5
N12—C12—C12B	107.7 (6)	H32B—C32A—H32C	109.5
C12C—C12—C12B	109.5 (6)	C32—C32B—H32D	109.5
C12A—C12—C12B	108.8 (6)	C32—C32B—H32E	109.5
C12—C12A—H12A	109.5	H32D—C32B—H32E	109.5
C12—C12A—H12B	109.5	C32—C32B—H32F	109.5
H12A—C12A—H12B	109.5	H32D—C32B—H32F	109.5
C12—C12A—H12C	109.5	H32E—C32B—H32F	109.5
H12A—C12A—H12C	109.5	C32—C32C—H32G	109.5
H12B—C12A—H12C	109.5	C32—C32C—H32H	109.5
C12—C12B—H12D	109.5	H32G—C32C—H32H	109.5
C12—C12B—H12E	109.5	C32—C32C—H32I	109.5
H12D—C12B—H12E	109.5	H32G—C32C—H32I	109.5
C12—C12B—H12F	109.5	H32H—C32C—H32I	109.5
H12D—C12B—H12F	109.5	C34—C33—N32	108.4 (6)
H12E—C12B—H12F	109.5	C34—C33—H33	125.8
C12—C12C—H12G	109.5	N32—C33—H33	125.8
C12—C12C—H12H	109.5	C33—C34—N35	106.8 (6)
H12G—C12C—H12H	109.5	C33—C34—H34	126.6
C12—C12C—H12I	109.5	N35—C34—H34	126.6
H12G—C12C—H12I	109.5	C31—N35—C34	110.3 (5)
H12H—C12C—H12I	109.5	C31—N35—H35	124.9
C14—C13—N12	108.3 (6)	C34—N35—H35	124.9
C14—C13—H13	125.9	C41—S41—Pb1	101.6 (2)
N12—C13—H13	125.9	N45—C41—N42	106.0 (6)
C13—C14—N15	106.7 (6)	N45—C41—S41	124.2 (5)
C13—C14—H14	126.7	N42—C41—S41	129.8 (5)
N15—C14—H14	126.7	C41—N42—C43	107.5 (6)
C11—N15—C14	110.7 (5)	C41—N42—C42	127.3 (5)
C11—N15—H15	124.7	C43—N42—C42	125.1 (6)
C14—N15—H15	124.7	N42—C42—C42B	109.8 (5)
C21—S21—Pb1	117.4 (2)	N42—C42—C42A	109.0 (6)
N22—C21—N25	106.3 (5)	C42B—C42—C42A	111.3 (7)
N22—C21—S21	129.2 (5)	N42—C42—C42C	108.9 (6)
N25—C21—S21	124.5 (5)	C42B—C42—C42C	109.5 (7)
C21—N22—C23	108.7 (6)	C42A—C42—C42C	108.4 (6)
C21—N22—C22	126.8 (5)	C42—C42A—H42A	109.5
C23—N22—C22	124.4 (6)	C42—C42A—H42B	109.5
N22—C22—C22C	109.2 (6)	H42A—C42A—H42B	109.5
N22—C22—C22B	108.1 (6)	C42—C42A—H42C	109.5
C22C—C22—C22B	112.0 (7)	H42A—C42A—H42C	109.5
N22—C22—C22A	109.2 (7)	H42B—C42A—H42C	109.5
C22C—C22—C22A	108.4 (7)	C42—C42B—H42D	109.5
C22B—C22—C22A	109.9 (7)	C42—C42B—H42E	109.5
C22—C22A—H22A	109.5	H42D—C42B—H42E	109.5
C22—C22A—H22B	109.5	C42—C42B—H42F	109.5
H22A—C22A—H22B	109.5	H42D—C42B—H42F	109.5
C22—C22A—H22C	109.5	H42E—C42B—H42F	109.5
H22A—C22A—H22C	109.5	C42—C42C—H42G	109.5
H22B—C22A—H22C	109.5	C42—C42C—H42H	109.5
C22—C22B—H22D	109.5	H42G—C42C—H42H	109.5
C22—C22B—H22E	109.5	C42—C42C—H42I	109.5
H22D—C22B—H22E	109.5	H42G—C42C—H42I	109.5
C22—C22B—H22F	109.5	H42H—C42C—H42I	109.5
H22D—C22B—H22F	109.5	C44—C43—N42	109.1 (7)
H22E—C22B—H22F	109.5	C44—C43—H43	125.4
C22—C22C—H22G	109.5	N42—C43—H43	125.4
C22—C22C—H22H	109.5	C43—C44—N45	106.2 (7)
H22G—C22C—H22H	109.5	C43—C44—H44	126.9
C22—C22C—H22I	109.5	N45—C44—H44	126.9
H22G—C22C—H22I	109.5	C41—N45—C44	111.3 (6)
H22H—C22C—H22I	109.5	C41—N45—H45	124.3
C24—C23—N22	108.0 (6)	C44—N45—H45	124.3
C24—C23—H23	126

Experimental details

Crystal data
Chemical formula	[PbCl₂(C₇H₁₂N₂S)₄]
M_r	903.07
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.2683 (11), 10.9843 (13), 34.514 (4)
β (°)	93.294 (9)
V (Å³)	3886.4 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	11.97
Crystal size (mm)	0.40 × 0.29 × 0.17

Data collection
Diffractometer	Enraf-Nonius CAD-4 diffractometer
Absorption correction	Analytical (Katayama, 1986)
T_min, T_max	0.048, 0.214
No. of measured, independent and observed [I > 2σ(I)] reflections	10879, 6878, 5838
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.130, 1.03
No. of reflections	6878
No. of parameters	404
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.68, −1.50

Computer programs: CAD-4 EXPRESS (Enraf-Nonius, 1994), CAD-4 EXPRESS, XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

Pb1—S31	2.8698 (16)	Pb1—Cl1	3.0374 (18)
Pb1—S41	2.9057 (19)	Pb1—Cl2	3.0787 (17)
Pb1—S21	2.9299 (16)	Pb1—S11	3.0790 (16)

S31—Pb1—S41	92.26 (6)	S21—Pb1—Cl2	101.62 (5)
S31—Pb1—S21	87.51 (5)	Cl1—Pb1—Cl2	93.01 (5)
S41—Pb1—S21	76.93 (5)	S31—Pb1—S11	78.34 (4)
S31—Pb1—Cl1	90.14 (5)	S41—Pb1—S11	81.82 (5)
S41—Pb1—Cl1	166.54 (5)	S21—Pb1—S11	153.93 (5)
S21—Pb1—Cl1	89.95 (5)	Cl1—Pb1—S11	111.64 (5)
S31—Pb1—Cl2	170.34 (5)	Cl2—Pb1—S11	92.01 (4)
S41—Pb1—Cl2	86.79 (6)

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