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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 68| Part 4| April 2012| Pages m489-m490
doi:10.1107/S1600536812011877

Redetermination of (D-penicillaminato)lead(II)

Adam C. Schell,a Masood Parveza and Farideh Jalilehvanda*

aDepartment of Chemistry, The University of Calgary, 2500 University Drive NW, Calgary, Alberta, Canada T2N 1N4
*Correspondence e-mail: faridehj@ucalgary.ca

(Received 13 January 2012; accepted 19 March 2012; online 28 March 2012)

In the title coordination polymer, [Pb(C5H9NO2S)]n {systematic name: catena-poly[(μ-2-amino-3-methyl-3-sulfido­butano­ato)lead(II)]}, the D-penicillaminate ligand coordin­ates to the metal ion in an N,S,O-tridentate mode. The S atom acts as a bridge to two neighbouring PbII ions, thereby forming a double thiol­ate chain. Moreover, the coordinating carboxyl­ate O atom forms bridges to the PbII ions in the adjacent chain. The overall coordination sphere of the PbII ion can be described as a highly distorted penta­gonal bipyramid with a void in the equatorial plane between the long Pb—S bonds probably occupied by the stereochemically active inert electron pair. The amino H atoms form N—H⋯S and N—H⋯O hydrogen bonds, resulting in a cluster of four complex units, giving rise to an R44(16) ring lying in the ab plane. The crystal structure of the title compound has been reported previously [Freeman et al. (1974[Freeman, H. C., Stevens, G. N. & Taylor, I. F. J. (1974). Chem. Soc. Chem. Commun. pp. 366-367.]). Chem. Soc. Chem. Commun. pp. 366–367] but the atomic coordinates have not been deposited in the Cambridge Structural Database (refcode DPENPB). Additional details of the hydrogen bonding are presented here.

Related literature

For an earlier characterization of the title compound, see: Freeman et al. (1974[Freeman, H. C., Stevens, G. N. & Taylor, I. F. J. (1974). Chem. Soc. Chem. Commun. pp. 366-367.]). For neurotoxic effects of Pb, see: Needleman (2004[Needleman, H. (2004). Annu. Rev. Med. 55, 209-222.]); Bressler et al. (1999[Bressler, J., Kim, K.-A., Chakraborti, T. & Goldstein, G. (1999). Neurochem. Res. 24, 595-600.]); Godwin (2001[Godwin, H. A. (2001). Curr. Opin. Chem. Biol. 5, 223-227.]). For treatments of lead(II) poisoning, see: Sinicropi et al. (2010)[Sinicropi, M. S., Amantea, D., Caruso, A. & Saturnino, C. (2010). Arch. Toxicol. 84, 501-520.]; Casas & Sordo (2006[Casas, J. S. & Sordo, J. (2006). Lead: Chemistry, Analytical Aspects, Environmental Impact and Health Effects, edited by J.S. Casas & J. Sordo, Amesterdam: Elsevier Science Technology.]). For graph-set notation, see: Bernstein et al. (1994[Bernstein, J., Etter, M. C. & Leiserowitz, L. (1994). Structure Correlation, edited by H. -B. Bürgi & J. D. Dunitz, Vol. 2., pp. 431-507. New York: VCH.]).

[Scheme 1]

Experimental

Crystal data

  • [Pb(C5H9NO2S)]

  • Mr = 354.38

  • Monoclinic, P 21

  • a = 6.251 (4) Å

  • b = 6.179 (3) Å

  • c = 10.259 (6) Å

  • β = 107.72 (2)°

  • V = 377.5 (4) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 22.56 mm−1

  • T = 123 K

  • 0.06 × 0.05 × 0.02 mm
Data collection

  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.345, Tmax = 0.661

  • 6589 measured reflections

  • 2157 independent reflections

  • 2027 reflections with I > 2σ(I)

  • Rint = 0.059
Refinement

  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.085

  • S = 1.09

  • 2157 reflections

  • 93 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 2.76 e Å−3

  • Δρmin = −3.17 e Å−3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 966 Friedel pairs

  • Flack parameter: 0.03 (2)

Table 1
Selected bond lengths (Å)

Pb1—N1 2.444 (9)
Pb1—O1 2.451 (7)
Pb1—S1 2.714 (2)
Pb1—O1i 2.719 (7)
Pb1—S1ii 3.091 (3)
Pb1—S1iii 3.465 (3)
Symmetry codes: (i) [-x+2, y-{\script{1\over 2}}, -z+1]; (ii) [-x+1, y-{\script{1\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z+1].

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1B⋯S1iii 0.92 2.59 3.453 (8) 156
N1—H1A⋯O2iv 0.92 2.24 3.070 (10) 150
Symmetry codes: (iii) x+1, y, z; (iv) x, y-1, z.

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius B V, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr. and R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr. and R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812011877/hb6608sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812011877/hb6608Isup2.hkl

checkCIF report


Comment top

Lead is a serious environmental contaminant. The extensive use of lead as metal and in lead compounds into modern times, e. g., in alkyl lead additives in leaded gasoline, battery manufacturing and in paints, has made lead a ubiquitous pollutant in the ecosystem. The soluble PbII ion with its 5 d10 6 s2 electronic configuration in the valence shell has a very flexible coordination behaviour. It is a neurotoxic heavy metal ion that perturbs multiple enzyme systems affecting areas of the brain that regulate behavior and nerve cell development and any site with sulfhydryl groups is vulnerable (Needleman, 2004). In particular Zn(II) can be replaced in enzymes, e. g., inhibiting the heme biosynthetic pathway, even though the effective ionic radius in four-coordination of the soft PbII ion (0.98 Å) is significantly larger than that of ZnII (0.60 Å). PbII can also adapt to replace Ca(II) in bone (Bressler et al., 1999; Godwin, 2001).

Treatments of lead(II) poisoning are mainly based on using chelators that form strong bonds to heavy metal ions, such as the disodium salt of the calcium edta complex (CaNa2edta) and dimercaprol (BAL), which are injected, and DMSA (meso-2, 3-dimercaptosuccinic acid) and D-penicillamine (H2Pen), which are administered orally (Sinicropi et al., 2010; Casas & Sordo, 2006).

The binding of PbII to the tridentate chelator H2Pen containing a sulfhydryl group is of interest for better understanding of the coordination behaviour in biological systems and for the design of specific detoxifying agents. The coordination geometry around the PbII ion in the crystalline title compound (PbPen), which precipitates in a wide pH range from penicillamine solutions containing lead(II) ions, was previously discussed by Freeman et al., (1974). However, the atomic coordinates of the crystal structure were not reported, nor deposited in the Cambridge Structural Database (refcode: DPENPB]. Here, we report the crystal structure of PbPen, and also discuss the Pb—Pb distances in this polymeric structure with double bridged thiolate chains.

Mixing Pb(NO3)2 and D-penicillamine in 1:2 molar ratio resulted in a 1:1 complex, PbPen, formed in an alkaline solution. The ligand is coordinated to the PbII ion in a tridentate mode: Pb—N 2.444 (9) Å, Pb—O 2.451 (7) Å and Pb—S 2.714 (2) Å (Fig. 1). The sulfur atom acts as a bridge with Pb—S distances of 3.091 (2) and 3.464 (2) Å to two other neighbouring PbII ions located at 4.363 Å relative to the original PbII ion, forming a double thiolate chain in a polymeric structure. Moreover, the coordinated carboxylate oxygen atom forms bridges to the lead ions (Pb—O 2.720 (7) Å) in the adjacent chain with two PbII ions at 4.663 Å relative to the central PbII ion (Fig. 2). The coordination sphere of lead can be described as a distorted pentagonal bipyramid if the Pb—O interactions to the carboxylate oxygen atoms are considered as axial interaction opposite the short Pb—S bond (2.714 (2) Å), and also including a possible stereochemically active inert electron pair in the void in the equatorial plane between the two long Pb—S interactions, 3.091 (2) Å and 3.464 (2) Å (Fig. 3) (Freeman et al., 1974).

The amino H-atoms of the title complex are hydrogen bonded to a S-atom (N1—H1B···S1) along the a-axis and an O-atom (N1—H1A···O2) along the b-axis resulting in a cluster of four complex units giving rise to a 16-membered ring in the ab-plane which can be best described as a R44(16) motif in the graph set notation (Bernstein et al., 1994) (Fig. 4).

Related literature top

For an earlier characterization of the title compound, see: Freeman et al. (1974). For neurotoxic effects of Pb, see: Needleman (2004); Bressler et al. (1999); Godwin (2001). For treatments of lead(II) poisoning, see: Sinicropi et al. (2010); Casas & Sordo (2006). For graph-set notation, see: (Bernstein et al. 1994).

Experimental top

To a solution of 2 mmol penicillamine (H2Pen) in boiled O2-free water, 1 mmol Pb(NO3)2 was added, forming a white precipitate, which was dissolved by adding 2 and 6 M NaOH solution, increasing the pH to 11.2; [Pb2+] = 0.1 M. After several days in the refrigerator colorless plates formed.

Refinement top

All H atoms were positioned geometrically and refined using a riding model, with N—H = 0.92 Å and C—H = 0.98 and 1.00 Å, for methyl and methylene H-atoms, respectively, and the Uiso(H) were allowed at 1.5Ueq(N/C). An absolute structure was determined using 966 Friedel pairs of reflections which were not merged; the Flack parameter was 0.03 (2) (Flack, 1983). The largest residual peaks in the final difference map were located in the close proximity of the Pb atom and may be attributed to inadequate absorption correction.

Structure description top

Lead is a serious environmental contaminant. The extensive use of lead as metal and in lead compounds into modern times, e. g., in alkyl lead additives in leaded gasoline, battery manufacturing and in paints, has made lead a ubiquitous pollutant in the ecosystem. The soluble PbII ion with its 5 d10 6 s2 electronic configuration in the valence shell has a very flexible coordination behaviour. It is a neurotoxic heavy metal ion that perturbs multiple enzyme systems affecting areas of the brain that regulate behavior and nerve cell development and any site with sulfhydryl groups is vulnerable (Needleman, 2004). In particular Zn(II) can be replaced in enzymes, e. g., inhibiting the heme biosynthetic pathway, even though the effective ionic radius in four-coordination of the soft PbII ion (0.98 Å) is significantly larger than that of ZnII (0.60 Å). PbII can also adapt to replace Ca(II) in bone (Bressler et al., 1999; Godwin, 2001).

Treatments of lead(II) poisoning are mainly based on using chelators that form strong bonds to heavy metal ions, such as the disodium salt of the calcium edta complex (CaNa2edta) and dimercaprol (BAL), which are injected, and DMSA (meso-2, 3-dimercaptosuccinic acid) and D-penicillamine (H2Pen), which are administered orally (Sinicropi et al., 2010; Casas & Sordo, 2006).

The binding of PbII to the tridentate chelator H2Pen containing a sulfhydryl group is of interest for better understanding of the coordination behaviour in biological systems and for the design of specific detoxifying agents. The coordination geometry around the PbII ion in the crystalline title compound (PbPen), which precipitates in a wide pH range from penicillamine solutions containing lead(II) ions, was previously discussed by Freeman et al., (1974). However, the atomic coordinates of the crystal structure were not reported, nor deposited in the Cambridge Structural Database (refcode: DPENPB]. Here, we report the crystal structure of PbPen, and also discuss the Pb—Pb distances in this polymeric structure with double bridged thiolate chains.

Mixing Pb(NO3)2 and D-penicillamine in 1:2 molar ratio resulted in a 1:1 complex, PbPen, formed in an alkaline solution. The ligand is coordinated to the PbII ion in a tridentate mode: Pb—N 2.444 (9) Å, Pb—O 2.451 (7) Å and Pb—S 2.714 (2) Å (Fig. 1). The sulfur atom acts as a bridge with Pb—S distances of 3.091 (2) and 3.464 (2) Å to two other neighbouring PbII ions located at 4.363 Å relative to the original PbII ion, forming a double thiolate chain in a polymeric structure. Moreover, the coordinated carboxylate oxygen atom forms bridges to the lead ions (Pb—O 2.720 (7) Å) in the adjacent chain with two PbII ions at 4.663 Å relative to the central PbII ion (Fig. 2). The coordination sphere of lead can be described as a distorted pentagonal bipyramid if the Pb—O interactions to the carboxylate oxygen atoms are considered as axial interaction opposite the short Pb—S bond (2.714 (2) Å), and also including a possible stereochemically active inert electron pair in the void in the equatorial plane between the two long Pb—S interactions, 3.091 (2) Å and 3.464 (2) Å (Fig. 3) (Freeman et al., 1974).

The amino H-atoms of the title complex are hydrogen bonded to a S-atom (N1—H1B···S1) along the a-axis and an O-atom (N1—H1A···O2) along the b-axis resulting in a cluster of four complex units giving rise to a 16-membered ring in the ab-plane which can be best described as a R44(16) motif in the graph set notation (Bernstein et al., 1994) (Fig. 4).

For an earlier characterization of the title compound, see: Freeman et al. (1974). For neurotoxic effects of Pb, see: Needleman (2004); Bressler et al. (1999); Godwin (2001). For treatments of lead(II) poisoning, see: Sinicropi et al. (2010); Casas & Sordo (2006). For graph-set notation, see: (Bernstein et al. 1994).

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. H atoms were omitted for clarity. [Symmetry codes: * -x + 2, -1/2 + y, -z + 1; ' -x + 1, -1/2 + y, -z + 1; " -x + 1, 1/2 + y, -z + 1]
[Figure 2] Fig. 2. A perspective drawing of the title compound showing coordination geometry around Pb and double bridges formed by sulfur atoms giving rise to infinite chains held together via bridging carboxylate groups. H atoms were omitted for clarity.
[Figure 3] Fig. 3. A view of the unit cell of the crystal structure of the title compound. H atoms non-participating in hydrogen-bonding were omitted for clarity. Long bond distances are drawn as dotted lines.
[Figure 4] Fig. 4. A view of the N—-H···O and N—H···S hydrogen bonds (dotted lines) in the crystal structure of the title compound. H atoms were omitted for clarity.
catena-poly[(µ-2-amino-3-methyl-3-sulfidobutanoato)lead(II)] top
Crystal data top
[Pb(C5H9NO2S)]F(000) = 320
Mr = 354.38Dx = 3.118 Mg m−3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 2175 reflections
a = 6.251 (4) Åθ = 3.4–30.0°
b = 6.179 (3) ŵ = 22.56 mm−1
c = 10.259 (6) ÅT = 123 K
β = 107.72 (2)°Plate, colorless
V = 377.5 (4) Å30.06 × 0.05 × 0.02 mm
Z = 2
Data collection top
Nonius KappaCCD
diffractometer		2157 independent reflections
Radiation source: fine-focus sealed tube2027 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ω and φ scansθmax = 30.0°, θmin = 3.4°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)		h = −8→8
Tmin = 0.345, Tmax = 0.661k = −8→8
6589 measured reflectionsl = −14→14
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.085 w = 1/[σ2(Fo2) + (0.0541P)2 + 1.7279P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
2157 reflectionsΔρmax = 2.76 e Å−3
93 parametersΔρmin = −3.17 e Å−3
1 restraintAbsolute structure: Flack (1983), 966 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.03 (2)
Crystal data top
[Pb(C5H9NO2S)]V = 377.5 (4) Å3
Mr = 354.38Z = 2
Monoclinic, P21Mo Kα radiation
a = 6.251 (4) ŵ = 22.56 mm−1
b = 6.179 (3) ÅT = 123 K
c = 10.259 (6) Å0.06 × 0.05 × 0.02 mm
β = 107.72 (2)°
Data collection top
Nonius KappaCCD
diffractometer		2157 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)		2027 reflections with I > 2σ(I)
Tmin = 0.345, Tmax = 0.661Rint = 0.059
6589 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.032H-atom parameters constrained
wR(F2) = 0.085Δρmax = 2.76 e Å−3
S = 1.09Δρmin = −3.17 e Å−3
2157 reflectionsAbsolute structure: Flack (1983), 966 Friedel pairs
93 parametersAbsolute structure parameter: 0.03 (2)
1 restraint
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
xyzUiso*/Ueq
Pb10.70681 (4)0.20419 (12)0.44819 (2)0.01059 (9)
S10.4620 (3)0.2363 (4)0.6251 (2)0.0123 (5)
O10.9300 (11)0.4969 (11)0.5855 (7)0.0145 (13)
O21.0202 (11)0.6382 (11)0.7971 (7)0.0162 (13)
N10.9562 (13)0.0937 (13)0.6716 (9)0.0152 (16)
H1A0.9180−0.04160.69490.018*
H1B1.10320.09120.67150.018*
C10.6876 (13)0.2355 (15)0.7921 (9)0.0103 (18)
C20.9226 (13)0.2620 (12)0.7695 (9)0.0091 (16)
H21.03990.23890.85960.011*
C30.9615 (14)0.4861 (15)0.7162 (9)0.0106 (16)
C40.645 (2)0.410 (2)0.8842 (13)0.014 (2)
H4A0.75840.39990.97430.017*
H4B0.49540.39020.89400.017*
H4C0.65440.55190.84410.017*
C50.680 (2)0.016 (2)0.8594 (14)0.018 (2)
H5A0.80640.00490.94360.021*
H5B0.6895−0.09980.79640.021*
H5C0.53840.00310.88160.021*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.00940 (13)0.01069 (14)0.01203 (14)0.0004 (2)0.00381 (9)0.0000 (2)
S10.0067 (7)0.0167 (15)0.0139 (8)0.0002 (8)0.0039 (6)−0.0002 (9)
O10.013 (3)0.016 (3)0.015 (3)−0.001 (2)0.005 (2)0.002 (3)
O20.021 (3)0.012 (3)0.016 (3)−0.005 (2)0.006 (3)−0.002 (2)
N10.011 (3)0.011 (4)0.025 (4)0.003 (3)0.008 (3)0.001 (3)
C10.012 (3)0.008 (5)0.012 (3)0.001 (3)0.005 (3)0.005 (3)
C20.004 (3)0.010 (4)0.011 (4)0.000 (2)−0.001 (3)−0.006 (3)
C30.003 (3)0.014 (4)0.015 (4)0.000 (3)0.002 (3)0.003 (3)
C40.015 (5)0.016 (5)0.014 (5)−0.002 (4)0.009 (4)−0.006 (4)
C50.017 (5)0.015 (5)0.025 (6)−0.002 (4)0.011 (4)−0.003 (4)
Geometric parameters (Å, º) top
Pb1—N12.444 (9)N1—H1B0.9200
Pb1—O12.451 (7)C1—C41.507 (15)
Pb1—S12.714 (2)C1—C51.528 (16)
Pb1—O1i2.719 (7)C1—C21.564 (11)
Pb1—S1ii3.091 (3)C2—C31.535 (12)
Pb1—S1iii3.465 (3)C2—H21.0000
S1—Pb1iii3.091 (3)C4—H4A0.9800
S1—C11.858 (9)C4—H4B0.9800
O1—C31.297 (11)C4—H4C0.9800
O1—Pb1iv2.719 (7)C5—H5A0.9800
O2—C31.233 (11)C5—H5B0.9800
N1—C21.504 (11)C5—H5C0.9800
N1—H1A0.9200
N1—Pb1—O165.0 (3)C4—C1—S1110.3 (7)
N1—Pb1—S173.8 (2)C5—C1—S1107.4 (7)
O1—Pb1—S184.25 (17)C2—C1—S1110.3 (6)
N1—Pb1—O1i70.7 (2)N1—C2—C3108.5 (7)
O1—Pb1—O1i93.98 (13)N1—C2—C1110.8 (7)
S1—Pb1—O1i141.45 (16)C3—C2—C1113.9 (7)
N1—Pb1—S1ii92.28 (19)N1—C2—H2107.8
O1—Pb1—S1ii157.30 (16)C3—C2—H2107.8
S1—Pb1—S1ii90.61 (6)C1—C2—H2107.8
O1i—Pb1—S1ii76.40 (15)O2—C3—O1125.2 (9)
C1—S1—Pb1101.1 (3)O2—C3—C2119.7 (8)
C1—S1—Pb1iii109.5 (3)O1—C3—C2115.1 (8)
Pb1—S1—Pb1iii97.24 (7)C1—C4—H4A109.5
C3—O1—Pb1115.9 (6)C1—C4—H4B109.5
C3—O1—Pb1iv106.6 (5)H4A—C4—H4B109.5
Pb1—O1—Pb1iv128.8 (3)C1—C4—H4C109.5
C2—N1—Pb1104.7 (5)H4A—C4—H4C109.5
C2—N1—H1A110.8H4B—C4—H4C109.5
Pb1—N1—H1A110.8C1—C5—H5A109.5
C2—N1—H1B110.8C1—C5—H5B109.5
Pb1—N1—H1B110.8H5A—C5—H5B109.5
H1A—N1—H1B108.9C1—C5—H5C109.5
C4—C1—C5108.3 (8)H5A—C5—H5C109.5
C4—C1—C2111.7 (8)H5B—C5—H5C109.5
C5—C1—C2108.7 (8)
N1—Pb1—S1—C117.3 (4)Pb1iii—S1—C1—C432.8 (7)
O1—Pb1—S1—C1−48.4 (4)Pb1—S1—C1—C5−107.5 (6)
O1i—Pb1—S1—C140.8 (4)Pb1iii—S1—C1—C5150.6 (6)
S1ii—Pb1—S1—C1109.5 (3)Pb1—S1—C1—C210.8 (6)
N1—Pb1—S1—Pb1iii128.8 (2)Pb1iii—S1—C1—C2−91.1 (6)
O1—Pb1—S1—Pb1iii63.19 (17)Pb1—N1—C2—C3−53.8 (7)
O1i—Pb1—S1—Pb1iii152.4 (2)Pb1—N1—C2—C171.9 (7)
S1ii—Pb1—S1—Pb1iii−138.97 (9)C4—C1—C2—N1−177.1 (8)
N1—Pb1—O1—C3−36.8 (6)C5—C1—C2—N163.5 (10)
S1—Pb1—O1—C338.0 (6)S1—C1—C2—N1−54.0 (8)
O1i—Pb1—O1—C3−103.4 (5)C4—C1—C2—C3−54.5 (10)
S1ii—Pb1—O1—C3−39.7 (8)C5—C1—C2—C3−173.9 (8)
N1—Pb1—O1—Pb1iv106.1 (4)S1—C1—C2—C368.6 (8)
S1—Pb1—O1—Pb1iv−179.1 (3)Pb1—O1—C3—O2−161.7 (7)
O1i—Pb1—O1—Pb1iv39.6 (3)Pb1iv—O1—C3—O247.6 (10)
S1ii—Pb1—O1—Pb1iv103.2 (4)Pb1—O1—C3—C218.9 (9)
O1—Pb1—N1—C245.4 (5)Pb1iv—O1—C3—C2−131.8 (6)
S1—Pb1—N1—C2−45.8 (5)N1—C2—C3—O2−154.8 (8)
O1i—Pb1—N1—C2149.5 (5)C1—C2—C3—O281.3 (10)
S1ii—Pb1—N1—C2−135.8 (5)N1—C2—C3—O124.6 (9)
Pb1—S1—C1—C4134.7 (7)C1—C2—C3—O1−99.3 (8)
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+1; (iv) −x+2, y+1/2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···S1v0.922.593.453 (8)156
N1—H1A···O2vi0.922.243.070 (10)150
Symmetry codes: (v) x+1, y, z; (vi) x, y−1, z.

Experimental details

Crystal data
Chemical formula[Pb(C5H9NO2S)]
Mr354.38
Crystal system, space groupMonoclinic, P21
Temperature (K)123
a, b, c (Å)6.251 (4), 6.179 (3), 10.259 (6)
β (°) 107.72 (2)
V (Å3)377.5 (4)
Z2
Radiation typeMo Kα
µ (mm−1)22.56
Crystal size (mm)0.06 × 0.05 × 0.02
Data collection
DiffractometerNonius KappaCCD
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.345, 0.661
No. of measured, independent and
observed [I > 2σ(I)] reflections		6589, 2157, 2027
Rint0.059
(sin θ/λ)max (Å−1)0.703
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.085, 1.09
No. of reflections2157
No. of parameters93
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)2.76, −3.17
Absolute structureFlack (1983), 966 Friedel pairs
Absolute structure parameter0.03 (2)

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Selected bond lengths (Å) top
Pb1—N12.444 (9)Pb1—O1i2.719 (7)
Pb1—O12.451 (7)Pb1—S1ii3.091 (3)
Pb1—S12.714 (2)Pb1—S1iii3.465 (3)
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+1, y+1/2, −z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···S1iv0.922.593.453 (8)156
N1—H1A···O2v0.922.243.070 (10)150
Symmetry codes: (iv) x+1, y, z; (v) x, y−1, z.
 

Acknowledgements

This research was supported by the National Science and Engineering Research Council (NSERC) of Canada, the Canadian Foundation for Innovation (CFI) and the Province of Alberta (Department of Innovation and Science).

References

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ISSN: 2056-9890
Volume 68| Part 4| April 2012| Pages m489-m490
doi:10.1107/S1600536812011877
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