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Acta Cryst. (2010). E66, m529    [ doi:10.1107/S1600536810012742 ]

Bis(2-methylquinolin-8-olato-[kappa]2N,O)lead(II)

G. Mohammadnezhad, A. R. Ghanbarpour, M. M. Amini and S. W. Ng

Abstract top

The PbII atom in the title compound, [Pb(C10H8NO)2], is chelated by two oxine (2-methylquinolin-8-olate) anions in a [Psi]-trigonal-bipyramidal geometry; the N atoms occupy the axial sites. The molecule lies about a twofold rotation axis.

Comment top

Bis(quinolin-8-olato)lead(II) exists as a centrosymmetric dinuclear entity in which one of the two oxygen atoms also functions as a bridge. As adjacent molecules are linked by a weaker Pb···O interaction to generate a chain motif, the metal atom is regarded as being six-coordinate in a Ψ-pentagonal bipyramidal geometry, the lone pair electrons occupying an axial site (Zhu et al., 2005). In the present methyl-substituted analogue, the substituent is able to block the approach of neighboring potentially coordinating atoms so that the compound is only four-coordinate (Scheme I, Fig. 1). The coordination polyhedron is a Ψ-trigonal bipyramid and the lone pair electrons occupy an equatorial site. The axial sites are occupied by the nitrogen atoms and the oxygen atoms occupy the other equatorial sites. The lone pair compresses the O–Pb–O angle (Table 1).

Related literature top

For the crystal structure of bis(quinolin-8-olato)lead(II), see: Zhu et al. (2005).

Experimental top

Lead (II) acetate trihydrate (1 mmol, 0.38 g), 2-methyl-8-hydroxyquinoline (1 mmol, 0.16 g) and sodium azide (1 mmol, 0.13 g) were loaded in to a convection tube; the tube was filled with 2:1 methanol/water and kept at 333 K. Crystals were collected after 1 week (m.p. > 543 K).

Refinement top

H-atoms were placed in calculated positions (C—H 0.94 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C). The final difference Fourier map had a large peak/deep hole in the vicinity of the lead atom.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound; ellipsoids are drawn at the 50% probability level and H atoms are of arbitrary radius.
Bis(2-methylquinolin-8-olato-κ2N,O)lead(II) top
Crystal data top
[Pb(C10H8NO)2]F(000) = 992
Mr = 523.54Dx = 2.110 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 2952 reflections
a = 22.439 (2) Åθ = 2.6–25.2°
b = 4.7636 (5) ŵ = 10.25 mm−1
c = 15.7139 (15) ÅT = 223 K
β = 101.167 (1)°Prism, yellow
V = 1647.9 (3) Å30.30 × 0.06 × 0.04 mm
Z = 4
Data collection top
Bruker SMART APEX
diffractometer		1890 independent reflections
Radiation source: fine-focus sealed tube1765 reflections with I > 2σ(I)
graphiteRint = 0.053
ω scansθmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −28→28
Tmin = 0.149, Tmax = 0.685k = −6→6
7405 measured reflectionsl = −20→18
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.027Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.030P)2]
where P = (Fo2 + 2Fc2)/3
1890 reflections(Δ/σ)max = 0.001
115 parametersΔρmax = 1.69 e Å−3
0 restraintsΔρmin = −1.50 e Å−3
Crystal data top
[Pb(C10H8NO)2]V = 1647.9 (3) Å3
Mr = 523.54Z = 4
Monoclinic, C2/cMo Kα radiation
a = 22.439 (2) ŵ = 10.25 mm−1
b = 4.7636 (5) ÅT = 223 K
c = 15.7139 (15) Å0.30 × 0.06 × 0.04 mm
β = 101.167 (1)°
Data collection top
Bruker SMART APEX
diffractometer		1890 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		1765 reflections with I > 2σ(I)
Tmin = 0.149, Tmax = 0.685Rint = 0.053
7405 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.027H-atom parameters constrained
wR(F2) = 0.063Δρmax = 1.69 e Å−3
S = 1.02Δρmin = −1.50 e Å−3
1890 reflectionsAbsolute structure: ?
115 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pb10.50000.67661 (5)0.75000.02578 (9)
O10.55706 (16)0.3516 (7)0.6978 (2)0.0336 (8)
N10.57862 (15)0.4778 (8)0.8701 (2)0.0226 (7)
C10.6024 (2)0.2268 (10)0.7500 (3)0.0278 (10)
C20.6392 (2)0.0290 (11)0.7206 (3)0.0344 (11)
H20.6321−0.01690.66130.041*
C30.6864 (2)−0.1029 (11)0.7771 (4)0.0393 (13)
H30.7104−0.23510.75470.047*
C40.6991 (2)−0.0466 (10)0.8640 (4)0.0355 (11)
H40.7312−0.13880.90080.043*
C50.6632 (2)0.1522 (9)0.8974 (3)0.0286 (10)
C60.6149 (2)0.2861 (9)0.8407 (3)0.0237 (9)
C70.6717 (2)0.2286 (11)0.9859 (3)0.0333 (11)
H70.70270.14351.02660.040*
C80.6349 (2)0.4264 (11)1.0127 (3)0.0326 (11)
H80.64140.48031.07130.039*
C90.5878 (2)0.5476 (10)0.9526 (3)0.0263 (9)
C100.5462 (2)0.7635 (10)0.9794 (3)0.0317 (11)
H10A0.50480.72670.95010.048*
H10B0.55830.94900.96370.048*
H10C0.54870.75421.04170.048*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.02798 (15)0.02687 (14)0.02138 (14)0.0000.00204 (10)0.000
O10.0356 (19)0.0411 (19)0.0233 (18)0.0073 (15)0.0033 (15)−0.0031 (14)
N10.0225 (18)0.0247 (18)0.0207 (18)−0.0014 (15)0.0039 (14)−0.0012 (15)
C10.030 (3)0.030 (2)0.025 (2)−0.0004 (19)0.008 (2)−0.0019 (19)
C20.034 (3)0.037 (3)0.034 (3)−0.002 (2)0.012 (2)−0.006 (2)
C30.032 (3)0.034 (3)0.056 (4)0.004 (2)0.019 (3)−0.006 (2)
C40.025 (2)0.031 (2)0.050 (3)0.004 (2)0.007 (2)0.004 (2)
C50.021 (2)0.028 (2)0.035 (3)−0.0044 (18)0.003 (2)0.0039 (19)
C60.020 (2)0.027 (2)0.025 (2)−0.0052 (17)0.0053 (18)−0.0028 (18)
C70.028 (3)0.039 (3)0.030 (3)−0.004 (2)−0.003 (2)0.010 (2)
C80.036 (3)0.040 (3)0.021 (2)−0.005 (2)0.004 (2)0.000 (2)
C90.027 (2)0.028 (2)0.024 (2)−0.0103 (19)0.0062 (18)−0.0040 (19)
C100.036 (3)0.036 (2)0.026 (3)−0.007 (2)0.012 (2)−0.008 (2)
Geometric parameters (Å, °) top
Pb1—O1i2.262 (3)C4—C51.409 (7)
Pb1—O12.262 (3)C4—H40.9400
Pb1—N1i2.507 (3)C5—C71.414 (8)
Pb1—N12.507 (3)C5—C61.416 (7)
O1—C11.318 (6)C7—C81.371 (8)
N1—C91.316 (5)C7—H70.9400
N1—C61.363 (6)C8—C91.399 (7)
C1—C21.390 (7)C8—H80.9400
C1—C61.426 (7)C9—C101.501 (7)
C2—C31.393 (8)C10—H10A0.9700
C2—H20.9400C10—H10B0.9700
C3—C41.366 (8)C10—H10C0.9700
C3—H30.9400
O1—Pb1—O1i93.6 (2)C4—C5—C7124.2 (5)
O1i—Pb1—N1i69.46 (12)C4—C5—C6119.4 (5)
O1—Pb1—N1i80.42 (12)C7—C5—C6116.4 (4)
O1i—Pb1—N180.42 (12)N1—C6—C5121.5 (4)
O1—Pb1—N169.46 (12)N1—C6—C1117.2 (4)
N1—Pb1—N1i135.6 (1)C5—C6—C1121.3 (4)
C1—O1—Pb1120.4 (3)C8—C7—C5120.3 (5)
C9—N1—C6121.0 (4)C8—C7—H7119.9
C9—N1—Pb1126.8 (3)C5—C7—H7119.9
C6—N1—Pb1112.1 (3)C7—C8—C9119.9 (4)
O1—C1—C2122.4 (5)C7—C8—H8120.1
O1—C1—C6120.8 (4)C9—C8—H8120.1
C2—C1—C6116.8 (5)N1—C9—C8120.9 (4)
C1—C2—C3121.5 (5)N1—C9—C10117.5 (4)
C1—C2—H2119.3C8—C9—C10121.6 (4)
C3—C2—H2119.3C9—C10—H10A109.5
C4—C3—C2122.3 (5)C9—C10—H10B109.5
C4—C3—H3118.9H10A—C10—H10B109.5
C2—C3—H3118.9C9—C10—H10C109.5
C3—C4—C5118.8 (5)H10A—C10—H10C109.5
C3—C4—H4120.6H10B—C10—H10C109.5
C5—C4—H4120.6
O1i—Pb1—O1—C1−80.4 (3)C9—N1—C6—C1−178.9 (4)
N1i—Pb1—O1—C1−148.9 (4)Pb1—N1—C6—C1−1.1 (5)
N1—Pb1—O1—C1−2.0 (3)C4—C5—C6—N1179.4 (4)
O1i—Pb1—N1—C9−83.2 (4)C7—C5—C6—N1−0.1 (6)
O1—Pb1—N1—C9179.2 (4)C4—C5—C6—C1−0.9 (7)
N1i—Pb1—N1—C9−130.3 (4)C7—C5—C6—C1179.6 (4)
O1i—Pb1—N1—C699.1 (3)O1—C1—C6—N1−0.7 (6)
O1—Pb1—N1—C61.6 (3)C2—C1—C6—N1−179.4 (4)
N1i—Pb1—N1—C652.0 (3)O1—C1—C6—C5179.6 (4)
Pb1—O1—C1—C2−179.0 (4)C2—C1—C6—C50.9 (7)
Pb1—O1—C1—C62.4 (6)C4—C5—C7—C8179.4 (5)
O1—C1—C2—C3−179.2 (5)C6—C5—C7—C8−1.1 (7)
C6—C1—C2—C3−0.6 (7)C5—C7—C8—C91.7 (7)
C1—C2—C3—C40.2 (8)C6—N1—C9—C8−0.2 (6)
C2—C3—C4—C5−0.2 (8)Pb1—N1—C9—C8−177.7 (3)
C3—C4—C5—C7180.0 (5)C6—N1—C9—C10179.2 (4)
C3—C4—C5—C60.5 (7)Pb1—N1—C9—C101.7 (6)
C9—N1—C6—C50.8 (6)C7—C8—C9—N1−1.0 (7)
Pb1—N1—C6—C5178.6 (3)C7—C8—C9—C10179.6 (5)
Symmetry codes: (i) −x+1, y, −z+3/2.
Table 1
Selected geometric parameters (Å, °) top
Pb1—O12.262 (3)Pb1—N12.507 (3)
O1—Pb1—O1i93.6 (2)N1—Pb1—N1i135.6 (1)
Symmetry codes: (i) −x+1, y, −z+3/2.
Acknowledgements top

We thank the Graduate Study Council of Shahid Beheshti University (project No. 600/2097) and the University of Malaya for supporting this study.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2010). publCIF. In preparation.

Zhu, L.-H., Zeng, M.-H. & Ng, S. W. (2005). Acta Cryst. E61, m1082–m1084.