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Acta Crystallogr Sect E Struct Rep Online. 2010 March 1; 66(Pt 3): m298.
Published online 2010 February 13. doi:  10.1107/S1600536810005544
PMCID: PMC2983694

(2,2′-Bipyridine-κ2 N,N′)bis­(4-methyl­benzoato-κ2 O,O′)lead(II)

Abstract

In the title compound, [Pb(C8H7O2)2(C10H8N2)], the PbII ion is coordinated by two N atoms from one 2,2′-bipyridine ligand and four O atoms from two 4-methyl­benzoate anions in a distorted pseudo-square-pyramidal environment, considering one of the carboxyl­ate anions as an apical ligand. Pairs of complex mol­ecules related by inversion centers are organized into dimers via pairs of Pb(...)O inter­actions [3.185 (2) Å] and stacking interactions between 2,2′-bipyridine and 4-methyl­benzoate ligands, with a mean distance between their planes of 3.491 Å.

Related literature

For potential applications of lead compounds, see: Fan & Zhu (2006 [triangle]); Hamilton et al. (2004 [triangle]). For the use of aromatic carboxyl­ates and 2,2′-bipyridine-type ligands in the preparation of metal complexes, see: Wang et al. (2006 [triangle]); Masaoka et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m298-scheme1.jpg

Experimental

Crystal data

  • [Pb(C8H7O2)2(C10H8N2)]
  • M r = 633.65
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m298-efi1.jpg
  • a = 9.5510 (11) Å
  • b = 10.0805 (12) Å
  • c = 13.2483 (15) Å
  • α = 109.865 (1)°
  • β = 97.322 (1)°
  • γ = 90.643 (1)°
  • V = 1187.8 (2) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 7.14 mm−1
  • T = 296 K
  • 0.35 × 0.26 × 0.18 mm

Data collection

  • Bruker APEXII CCD area detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.124, T max = 0.277
  • 14285 measured reflections
  • 5555 independent reflections
  • 4965 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.023
  • wR(F 2) = 0.051
  • S = 1.02
  • 5555 reflections
  • 300 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.77 e Å−3
  • Δρmin = −0.76 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810005544/gk2256sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810005544/gk2256Isup2.hkl

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

Acknowledgments

The authors acknowledge the Doctoral Foundation of Henan Polytechnic University (B2008–58 648265).

supplementary crystallographic information

Comment

Recently, lead compounds have been increasingly studied owing to their possible applications in different fields (Fan et al., 2006; Hamilton et al., 2004), such as ion-exchange, nonlinear optics and catalysis, especially in environmental protection due to the toxicity of lead and in biological systems for its diverse interactions with biological molecules. As an important family of multidentate O-donor ligands, aromatic carboxylate ligands have been extensively employed in the preparation of metal-organic complexes because of their potential properties and intriguing structural topologies (Wang et al., 2006; Masaoka et al., 2001). Herein, we report the structure of the title complex.

The asymmetric unit of the title complex, [Pb(C8H7O2)2(C10H8N2)], contains a PbII cation, two 4-methylbenzoate ligands, one 2,2'-bipyridine ligand, as illustrated in Fig. 1. The PbII atom is hexacoordinated being chelated by two carboxylate groups and one 2,2'-bipyridine. The Pb—O bond lengths are in the range of 2.333 (2) to 2.701 (2) Å. The Pb—N bond lengths are 2.608 (3) to 2.656 (3) Å. The PbII atom has a distorted pseudo-square-pyramidal environment, considering one of the carboxylate anions as an apical ligand. The complex molecules related by inversion center are organized into dimeric units via a pair of Pb···O interactions of 3.185 (2) Å and stacking inteactions between 2,2'-bipyridine and 4-methylbenzoate ligands, with a mean distance between their planes of 3.491 Å.

Experimental

A mixture of Pb(CH3COO)2.3H2O (0.199 g, 0.52 mmol), 4-methylbenzoic acid (0.114 g, 0.84 mmol), 2,2'-bipyridine (0.033 g, 0.21 mmol) and distilled water (10 ml) was sealed in a 25 ml Teflon-lined stainless autoclave. The mixture was heated at 403 K for 7 days to give the colorless crystals suitable for X-ray diffraction analysis.

Refinement

All H atoms bounded to C atoms were placed in calculated positions and treated in a riding-model approximation, with C (aromatic)—H = 0.93 Å, C(methyl)—H = 0.96 Å and Uiso(Haromatic) = 1.2Ueq(C), Uiso(Hmethyl) = 1.5Ueq(C). Two rigid-bond restraints to Uij values (DELU) were imposed on bonded atoms Pb1—O4 and Pb1—O2.

Figures

Fig. 1.
The coordination environment around PbII in the title complex with the atom-labeling scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

Crystal data

[Pb(C8H7O2)2(C10H8N2)]Z = 2
Mr = 633.65F(000) = 612
Triclinic, P1Dx = 1.772 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.5510 (11) ÅCell parameters from 7017 reflections
b = 10.0805 (12) Åθ = 2.2–26.6°
c = 13.2483 (15) ŵ = 7.14 mm1
α = 109.865 (1)°T = 296 K
β = 97.322 (1)°Prism, colorless
γ = 90.643 (1)°0.35 × 0.26 × 0.18 mm
V = 1187.8 (2) Å3

Data collection

Bruker APEXII CCD area detector diffractometer5555 independent reflections
Radiation source: fine-focus sealed tube4965 reflections with I > 2σ(I)
graphiteRint = 0.027
[var phi] and ω scansθmax = 27.8°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −12→12
Tmin = 0.124, Tmax = 0.277k = −13→13
14285 measured reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.023Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.051H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0227P)2 + 0.140P] where P = (Fo2 + 2Fc2)/3
5555 reflections(Δ/σ)max = 0.001
300 parametersΔρmax = 0.77 e Å3
2 restraintsΔρmin = −0.76 e Å3

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Pb10.010726 (12)0.117736 (12)0.677133 (9)0.03988 (5)
O10.2108 (2)0.1792 (2)0.80800 (18)0.0483 (5)
O20.0648 (2)0.3523 (2)0.84728 (18)0.0543 (6)
O30.1789 (3)0.0320 (3)0.5511 (2)0.0601 (6)
O40.1595 (3)0.2603 (2)0.58236 (19)0.0556 (6)
N1−0.0850 (3)0.0481 (3)0.8332 (2)0.0468 (6)
N20.0489 (3)−0.1362 (3)0.6814 (2)0.0454 (6)
C10.1748 (3)0.2982 (3)0.8699 (3)0.0413 (7)
C20.2682 (3)0.3698 (3)0.9753 (3)0.0409 (7)
C30.4063 (3)0.3339 (3)0.9934 (3)0.0488 (8)
H3A0.44300.26320.93950.059*
C40.4895 (4)0.4025 (4)1.0911 (3)0.0586 (10)
H4A0.58250.37811.10160.070*
C50.4386 (4)0.5062 (4)1.1735 (3)0.0559 (9)
C60.3003 (4)0.5395 (4)1.1556 (3)0.0576 (9)
H6A0.26300.60761.21080.069*
C70.2156 (4)0.4740 (3)1.0576 (3)0.0470 (7)
H7A0.12330.50001.04700.056*
C80.5337 (5)0.5824 (5)1.2781 (4)0.0861 (15)
H8A0.59320.51641.29770.129*
H8B0.47700.62441.33430.129*
H8C0.59130.65481.26870.129*
C90.2085 (3)0.1461 (4)0.5346 (3)0.0449 (7)
C100.3033 (3)0.1363 (3)0.4516 (2)0.0413 (7)
C110.3697 (4)0.0135 (4)0.4040 (3)0.0522 (8)
H11A0.3569−0.06400.42540.063*
C120.4548 (4)0.0043 (4)0.3251 (3)0.0571 (9)
H12A0.4985−0.07920.29470.068*
C130.4757 (4)0.1168 (4)0.2909 (3)0.0532 (8)
C140.4090 (4)0.2395 (4)0.3393 (3)0.0662 (11)
H14A0.42090.31680.31730.079*
C150.3258 (4)0.2498 (4)0.4188 (3)0.0584 (9)
H15A0.28440.33420.45080.070*
C160.5663 (5)0.1044 (5)0.2032 (3)0.0709 (11)
H16A0.64550.04950.21180.106*
H16B0.59980.19700.20840.106*
H16C0.51130.05890.13350.106*
C17−0.1533 (4)0.1412 (4)0.9053 (3)0.0553 (9)
H17A−0.15600.23310.90460.066*
C18−0.2200 (4)0.1079 (4)0.9806 (3)0.0599 (10)
H18A−0.26570.17591.03010.072*
C19−0.2174 (4)−0.0266 (4)0.9810 (3)0.0640 (10)
H19A−0.2606−0.05211.03130.077*
C20−0.1495 (4)−0.1250 (4)0.9053 (3)0.0600 (10)
H20A−0.1487−0.21820.90320.072*
C21−0.0830 (3)−0.0847 (3)0.8330 (3)0.0435 (7)
C22−0.0052 (3)−0.1848 (3)0.7519 (3)0.0441 (7)
C230.0131 (5)−0.3217 (4)0.7493 (4)0.0672 (11)
H23A−0.0239−0.35310.79930.081*
C240.0856 (5)−0.4114 (4)0.6734 (4)0.0755 (12)
H24A0.0987−0.50350.67130.091*
C250.1376 (5)−0.3618 (4)0.6014 (4)0.0736 (12)
H25A0.1864−0.42030.54850.088*
C260.1179 (4)−0.2249 (4)0.6073 (3)0.0600 (9)
H26A0.1542−0.19250.55750.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pb10.04568 (8)0.03734 (7)0.03350 (7)0.00681 (5)0.00661 (5)0.00766 (5)
O10.0490 (13)0.0417 (13)0.0455 (12)0.0100 (10)0.0040 (10)0.0047 (10)
O20.0543 (14)0.0485 (12)0.0465 (12)0.0145 (11)−0.0036 (11)0.0024 (8)
O30.0754 (17)0.0499 (15)0.0603 (15)0.0102 (12)0.0314 (13)0.0178 (12)
O40.0650 (15)0.0465 (14)0.0517 (14)0.0039 (11)0.0230 (11)0.0069 (11)
N10.0555 (17)0.0416 (15)0.0474 (16)0.0116 (12)0.0152 (13)0.0175 (13)
N20.0493 (16)0.0372 (14)0.0425 (15)0.0101 (12)0.0068 (12)0.0041 (12)
C10.0449 (18)0.0384 (17)0.0400 (16)0.0004 (13)0.0069 (13)0.0122 (14)
C20.0449 (17)0.0317 (16)0.0451 (17)−0.0002 (13)0.0026 (13)0.0132 (13)
C30.0450 (18)0.0385 (18)0.062 (2)0.0048 (14)0.0081 (16)0.0162 (16)
C40.047 (2)0.045 (2)0.082 (3)−0.0008 (16)−0.0102 (18)0.025 (2)
C50.067 (2)0.0364 (18)0.059 (2)−0.0093 (16)−0.0156 (18)0.0191 (17)
C60.076 (3)0.0364 (18)0.051 (2)0.0046 (17)0.0001 (18)0.0063 (15)
C70.0463 (18)0.0387 (18)0.0507 (19)0.0068 (14)0.0017 (15)0.0102 (15)
C80.100 (4)0.059 (3)0.082 (3)−0.013 (2)−0.036 (3)0.019 (2)
C90.0417 (17)0.0466 (19)0.0370 (16)0.0020 (14)0.0028 (13)0.0035 (14)
C100.0392 (16)0.0446 (18)0.0352 (15)0.0013 (13)0.0022 (12)0.0084 (13)
C110.056 (2)0.050 (2)0.055 (2)0.0112 (16)0.0145 (16)0.0217 (17)
C120.059 (2)0.056 (2)0.059 (2)0.0196 (17)0.0222 (18)0.0187 (19)
C130.0469 (19)0.066 (2)0.050 (2)0.0074 (17)0.0112 (15)0.0227 (18)
C140.076 (3)0.059 (2)0.075 (3)0.009 (2)0.031 (2)0.031 (2)
C150.066 (2)0.045 (2)0.063 (2)0.0092 (17)0.0198 (19)0.0133 (18)
C160.065 (2)0.090 (3)0.068 (3)0.015 (2)0.028 (2)0.033 (2)
C170.068 (2)0.050 (2)0.053 (2)0.0179 (17)0.0216 (18)0.0189 (17)
C180.066 (2)0.066 (3)0.052 (2)0.0174 (19)0.0237 (18)0.0201 (19)
C190.066 (2)0.070 (3)0.064 (2)0.004 (2)0.023 (2)0.029 (2)
C200.071 (2)0.048 (2)0.068 (2)0.0028 (18)0.018 (2)0.0268 (19)
C210.0435 (18)0.0357 (17)0.0495 (18)0.0037 (13)0.0053 (14)0.0129 (14)
C220.0453 (18)0.0346 (17)0.0486 (18)0.0016 (13)0.0036 (14)0.0105 (14)
C230.080 (3)0.040 (2)0.082 (3)0.0076 (19)0.016 (2)0.019 (2)
C240.089 (3)0.036 (2)0.093 (3)0.015 (2)0.010 (3)0.011 (2)
C250.087 (3)0.050 (2)0.071 (3)0.030 (2)0.018 (2)0.001 (2)
C260.069 (2)0.048 (2)0.057 (2)0.0158 (18)0.0149 (18)0.0071 (17)

Geometric parameters (Å, °)

Pb1—O12.333 (2)C10—C111.386 (4)
Pb1—O32.418 (2)C11—C121.383 (5)
Pb1—N22.608 (3)C11—H11A0.9300
Pb1—O22.644 (2)C12—C131.378 (5)
Pb1—N12.656 (3)C12—H12A0.9300
Pb1—O42.701 (2)C13—C141.389 (5)
O1—C11.282 (4)C13—C161.509 (5)
O2—C11.239 (4)C14—C151.376 (5)
O3—C91.277 (4)C14—H14A0.9300
O4—C91.240 (4)C15—H15A0.9300
N1—C171.335 (4)C16—H16A0.9600
N1—C211.339 (4)C16—H16B0.9600
N2—C261.333 (4)C16—H16C0.9600
N2—C221.345 (4)C17—C181.378 (5)
C1—C21.500 (4)C17—H17A0.9300
C2—C71.384 (4)C18—C191.358 (5)
C2—C31.385 (4)C18—H18A0.9300
C3—C41.379 (5)C19—C201.384 (5)
C3—H3A0.9300C19—H19A0.9300
C4—C51.375 (5)C20—C211.378 (5)
C4—H4A0.9300C20—H20A0.9300
C5—C61.377 (5)C21—C221.486 (5)
C5—C81.508 (5)C22—C231.382 (5)
C6—C71.383 (5)C23—C241.372 (6)
C6—H6A0.9300C23—H23A0.9300
C7—H7A0.9300C24—C251.359 (6)
C8—H8A0.9600C24—H24A0.9300
C8—H8B0.9600C25—C261.372 (5)
C8—H8C0.9600C25—H25A0.9300
C9—C101.490 (4)C26—H26A0.9300
C10—C151.379 (5)
O1—Pb1—O384.31 (9)C15—C10—C11118.0 (3)
O1—Pb1—N283.74 (8)C15—C10—C9120.4 (3)
O3—Pb1—N277.33 (8)C11—C10—C9121.6 (3)
O1—Pb1—O252.25 (7)C12—C11—C10121.2 (3)
O3—Pb1—O2121.72 (8)C12—C11—H11A119.4
N2—Pb1—O2124.68 (8)C10—C11—H11A119.4
O1—Pb1—N179.77 (8)C13—C12—C11121.0 (3)
O3—Pb1—N1137.27 (8)C13—C12—H12A119.5
N2—Pb1—N161.75 (8)C11—C12—H12A119.5
O2—Pb1—N177.17 (8)C12—C13—C14117.4 (3)
O1—Pb1—O482.72 (8)C12—C13—C16120.5 (3)
O3—Pb1—O450.77 (8)C14—C13—C16122.1 (3)
N2—Pb1—O4127.29 (8)C15—C14—C13121.8 (4)
O2—Pb1—O483.26 (7)C15—C14—H14A119.1
N1—Pb1—O4159.20 (9)C13—C14—H14A119.1
C1—O1—Pb199.27 (19)C14—C15—C10120.6 (3)
C1—O2—Pb185.80 (18)C14—C15—H15A119.7
C9—O3—Pb199.36 (19)C10—C15—H15A119.7
C9—O4—Pb187.0 (2)C13—C16—H16A109.5
C17—N1—C21118.3 (3)C13—C16—H16B109.5
C17—N1—Pb1119.9 (2)H16A—C16—H16B109.5
C21—N1—Pb1121.1 (2)C13—C16—H16C109.5
C26—N2—C22118.0 (3)H16A—C16—H16C109.5
C26—N2—Pb1119.3 (2)H16B—C16—H16C109.5
C22—N2—Pb1122.6 (2)N1—C17—C18123.3 (3)
O2—C1—O1122.5 (3)N1—C17—H17A118.4
O2—C1—C2119.8 (3)C18—C17—H17A118.4
O1—C1—C2117.7 (3)C19—C18—C17118.5 (4)
C7—C2—C3118.6 (3)C19—C18—H18A120.7
C7—C2—C1119.6 (3)C17—C18—H18A120.7
C3—C2—C1121.8 (3)C18—C19—C20118.9 (3)
C4—C3—C2120.3 (3)C18—C19—H19A120.5
C4—C3—H3A119.9C20—C19—H19A120.5
C2—C3—H3A119.9C21—C20—C19119.8 (3)
C5—C4—C3121.7 (3)C21—C20—H20A120.1
C5—C4—H4A119.2C19—C20—H20A120.1
C3—C4—H4A119.2N1—C21—C20121.1 (3)
C4—C5—C6117.7 (3)N1—C21—C22116.7 (3)
C4—C5—C8120.4 (4)C20—C21—C22122.2 (3)
C6—C5—C8121.9 (4)N2—C22—C23120.9 (3)
C5—C6—C7121.6 (3)N2—C22—C21117.2 (3)
C5—C6—H6A119.2C23—C22—C21121.9 (3)
C7—C6—H6A119.2C24—C23—C22120.4 (4)
C6—C7—C2120.1 (3)C24—C23—H23A119.8
C6—C7—H7A120.0C22—C23—H23A119.8
C2—C7—H7A120.0C25—C24—C23118.1 (4)
C5—C8—H8A109.5C25—C24—H24A120.9
C5—C8—H8B109.5C23—C24—H24A120.9
H8A—C8—H8B109.5C24—C25—C26119.6 (4)
C5—C8—H8C109.5C24—C25—H25A120.2
H8A—C8—H8C109.5C26—C25—H25A120.2
H8B—C8—H8C109.5N2—C26—C25122.9 (4)
O4—C9—O3122.8 (3)N2—C26—H26A118.6
O4—C9—C10120.4 (3)C25—C26—H26A118.6
O3—C9—C10116.8 (3)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2256).

References

  • Bruker (2007). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fan, S. R. & Zhu, L. G. (2006). Inorg. Chem.45, 7935–7942. [PubMed]
  • Hamilton, B. H., Kelley, K. A., Wagler, T. A., Espe, M. P. & Ziegler, C. J. (2004). Inorg. Chem.43, 50–56. [PubMed]
  • Masaoka, S., Furukawa, S., Chang, H. C., Mizutani, T. & Kitagawa, S. (2001). Angew. Chem. Int. Ed.40, 3817–3819. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, X. L., Qin, C. & Wang, E. B. (2006). Cryst. Growth Des.6, 439–443.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography