Bis(2-methyl­quinolin-8-olato-κ2N,O)­lead(II)

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

doi:10.1107/S1600536810012742

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page m529

https://doi.org/10.1107/S1600536810012742

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Bis(2-methylquinolin-8-olato-κ²N,O)lead(II)

Gholamhossein Mohammadnezhad,^a Ali Reza Ghanbarpour,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 April 2010; accepted 6 April 2010; online 17 April 2010)

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

Related literature

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

Experimental

Crystal data

[Pb(C₁₀H₈NO)₂]
M_r = 523.54
Monoclinic, C 2/c
a = 22.439 (2) Å
b = 4.7636 (5) Å
c = 15.7139 (15) Å
β = 101.167 (1)°
V = 1647.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 10.25 mm⁻¹
T = 223 K
0.30 × 0.06 × 0.04 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.149, T_max = 0.685
7405 measured reflections
1890 independent reflections
1765 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.027
wR(F²) = 0.063
S = 1.02
1890 reflections
115 parameters
H-atom parameters constrained
Δρ_max = 1.69 e Å⁻³
Δρ_min = −1.50 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Pb1—O1	2.262 (3)
Pb1—N1	2.507 (3)

O1—Pb1—O1ⁱ	93.6 (2)
N1—Pb1—N1ⁱ	135.6 (1)
Symmetry code: (i) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810012742/bt5241sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810012742/bt5241Isup2.hkl

checkCIF report

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).

Structure description top

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

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

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
M_r = 523.54	D_x = 2.110 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2952 reflections
a = 22.439 (2) Å	θ = 2.6–25.2°
b = 4.7636 (5) Å	µ = 10.25 mm⁻¹
c = 15.7139 (15) Å	T = 223 K
β = 101.167 (1)°	Prism, yellow
V = 1647.9 (3) Å³	0.30 × 0.06 × 0.04 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	1890 independent reflections
Radiation source: fine-focus sealed tube	1765 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
ω scans	θ_max = 27.5°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −28→28
T_min = 0.149, T_max = 0.685	k = −6→6
7405 measured reflections	l = −20→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.027	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.030P)²] where P = (F_o² + 2F_c²)/3
1890 reflections	(Δ/σ)_max = 0.001
115 parameters	Δρ_max = 1.69 e Å⁻³
0 restraints	Δρ_min = −1.50 e Å⁻³

Crystal data top

[Pb(C₁₀H₈NO)₂]	V = 1647.9 (3) Å³
M_r = 523.54	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 22.439 (2) Å	µ = 10.25 mm⁻¹
b = 4.7636 (5) Å	T = 223 K
c = 15.7139 (15) Å	0.30 × 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)
T_min = 0.149, T_max = 0.685	R_int = 0.053
7405 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.063	H-atom parameters constrained
S = 1.02	Δρ_max = 1.69 e Å⁻³
1890 reflections	Δρ_min = −1.50 e Å⁻³
115 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	0.5000	0.67661 (5)	0.7500	0.02578 (9)
O1	0.55706 (16)	0.3516 (7)	0.6978 (2)	0.0336 (8)
N1	0.57862 (15)	0.4778 (8)	0.8701 (2)	0.0226 (7)
C1	0.6024 (2)	0.2268 (10)	0.7500 (3)	0.0278 (10)
C2	0.6392 (2)	0.0290 (11)	0.7206 (3)	0.0344 (11)
H2	0.6321	−0.0169	0.6613	0.041*
C3	0.6864 (2)	−0.1029 (11)	0.7771 (4)	0.0393 (13)
H3	0.7104	−0.2351	0.7547	0.047*
C4	0.6991 (2)	−0.0466 (10)	0.8640 (4)	0.0355 (11)
H4	0.7312	−0.1388	0.9008	0.043*
C5	0.6632 (2)	0.1522 (9)	0.8974 (3)	0.0286 (10)
C6	0.6149 (2)	0.2861 (9)	0.8407 (3)	0.0237 (9)
C7	0.6717 (2)	0.2286 (11)	0.9859 (3)	0.0333 (11)
H7	0.7027	0.1435	1.0266	0.040*
C8	0.6349 (2)	0.4264 (11)	1.0127 (3)	0.0326 (11)
H8	0.6414	0.4803	1.0713	0.039*
C9	0.5878 (2)	0.5476 (10)	0.9526 (3)	0.0263 (9)
C10	0.5462 (2)	0.7635 (10)	0.9794 (3)	0.0317 (11)
H10A	0.5048	0.7267	0.9501	0.048*
H10B	0.5583	0.9490	0.9637	0.048*
H10C	0.5487	0.7542	1.0417	0.048*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.02798 (15)	0.02687 (14)	0.02138 (14)	0.000	0.00204 (10)	0.000
O1	0.0356 (19)	0.0411 (19)	0.0233 (18)	0.0073 (15)	0.0033 (15)	−0.0031 (14)
N1	0.0225 (18)	0.0247 (18)	0.0207 (18)	−0.0014 (15)	0.0039 (14)	−0.0012 (15)
C1	0.030 (3)	0.030 (2)	0.025 (2)	−0.0004 (19)	0.008 (2)	−0.0019 (19)
C2	0.034 (3)	0.037 (3)	0.034 (3)	−0.002 (2)	0.012 (2)	−0.006 (2)
C3	0.032 (3)	0.034 (3)	0.056 (4)	0.004 (2)	0.019 (3)	−0.006 (2)
C4	0.025 (2)	0.031 (2)	0.050 (3)	0.004 (2)	0.007 (2)	0.004 (2)
C5	0.021 (2)	0.028 (2)	0.035 (3)	−0.0044 (18)	0.003 (2)	0.0039 (19)
C6	0.020 (2)	0.027 (2)	0.025 (2)	−0.0052 (17)	0.0053 (18)	−0.0028 (18)
C7	0.028 (3)	0.039 (3)	0.030 (3)	−0.004 (2)	−0.003 (2)	0.010 (2)
C8	0.036 (3)	0.040 (3)	0.021 (2)	−0.005 (2)	0.004 (2)	0.000 (2)
C9	0.027 (2)	0.028 (2)	0.024 (2)	−0.0103 (19)	0.0062 (18)	−0.0040 (19)
C10	0.036 (3)	0.036 (2)	0.026 (3)	−0.007 (2)	0.012 (2)	−0.008 (2)

Geometric parameters (Å, º) top

Pb1—O1ⁱ	2.262 (3)	C4—C5	1.409 (7)
Pb1—O1	2.262 (3)	C4—H4	0.9400
Pb1—N1ⁱ	2.507 (3)	C5—C7	1.414 (8)
Pb1—N1	2.507 (3)	C5—C6	1.416 (7)
O1—C1	1.318 (6)	C7—C8	1.371 (8)
N1—C9	1.316 (5)	C7—H7	0.9400
N1—C6	1.363 (6)	C8—C9	1.399 (7)
C1—C2	1.390 (7)	C8—H8	0.9400
C1—C6	1.426 (7)	C9—C10	1.501 (7)
C2—C3	1.393 (8)	C10—H10A	0.9700
C2—H2	0.9400	C10—H10B	0.9700
C3—C4	1.366 (8)	C10—H10C	0.9700
C3—H3	0.9400

O1—Pb1—O1ⁱ	93.6 (2)	C4—C5—C7	124.2 (5)
O1ⁱ—Pb1—N1ⁱ	69.46 (12)	C4—C5—C6	119.4 (5)
O1—Pb1—N1ⁱ	80.42 (12)	C7—C5—C6	116.4 (4)
O1ⁱ—Pb1—N1	80.42 (12)	N1—C6—C5	121.5 (4)
O1—Pb1—N1	69.46 (12)	N1—C6—C1	117.2 (4)
N1—Pb1—N1ⁱ	135.6 (1)	C5—C6—C1	121.3 (4)
C1—O1—Pb1	120.4 (3)	C8—C7—C5	120.3 (5)
C9—N1—C6	121.0 (4)	C8—C7—H7	119.9
C9—N1—Pb1	126.8 (3)	C5—C7—H7	119.9
C6—N1—Pb1	112.1 (3)	C7—C8—C9	119.9 (4)
O1—C1—C2	122.4 (5)	C7—C8—H8	120.1
O1—C1—C6	120.8 (4)	C9—C8—H8	120.1
C2—C1—C6	116.8 (5)	N1—C9—C8	120.9 (4)
C1—C2—C3	121.5 (5)	N1—C9—C10	117.5 (4)
C1—C2—H2	119.3	C8—C9—C10	121.6 (4)
C3—C2—H2	119.3	C9—C10—H10A	109.5
C4—C3—C2	122.3 (5)	C9—C10—H10B	109.5
C4—C3—H3	118.9	H10A—C10—H10B	109.5
C2—C3—H3	118.9	C9—C10—H10C	109.5
C3—C4—C5	118.8 (5)	H10A—C10—H10C	109.5
C3—C4—H4	120.6	H10B—C10—H10C	109.5
C5—C4—H4	120.6

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—N1	179.4 (4)
O1ⁱ—Pb1—N1—C9	−83.2 (4)	C7—C5—C6—N1	−0.1 (6)
O1—Pb1—N1—C9	179.2 (4)	C4—C5—C6—C1	−0.9 (7)
N1ⁱ—Pb1—N1—C9	−130.3 (4)	C7—C5—C6—C1	179.6 (4)
O1ⁱ—Pb1—N1—C6	99.1 (3)	O1—C1—C6—N1	−0.7 (6)
O1—Pb1—N1—C6	1.6 (3)	C2—C1—C6—N1	−179.4 (4)
N1ⁱ—Pb1—N1—C6	52.0 (3)	O1—C1—C6—C5	179.6 (4)
Pb1—O1—C1—C2	−179.0 (4)	C2—C1—C6—C5	0.9 (7)
Pb1—O1—C1—C6	2.4 (6)	C4—C5—C7—C8	179.4 (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—C9	1.7 (7)
C1—C2—C3—C4	0.2 (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—C7	180.0 (5)	C6—N1—C9—C10	179.2 (4)
C3—C4—C5—C6	0.5 (7)	Pb1—N1—C9—C10	1.7 (6)
C9—N1—C6—C5	0.8 (6)	C7—C8—C9—N1	−1.0 (7)
Pb1—N1—C6—C5	178.6 (3)	C7—C8—C9—C10	179.6 (5)

Symmetry code: (i) −x+1, y, −z+3/2.

Experimental details

Crystal data
Chemical formula	[Pb(C₁₀H₈NO)₂]
M_r	523.54
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	223
a, b, c (Å)	22.439 (2), 4.7636 (5), 15.7139 (15)
β (°)	101.167 (1)
V (Å³)	1647.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.25
Crystal size (mm)	0.30 × 0.06 × 0.04

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.149, 0.685
No. of measured, independent and observed [I > 2σ(I)] reflections	7405, 1890, 1765
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.063, 1.02
No. of reflections	1890
No. of parameters	115
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.69, −1.50

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected geometric parameters (Å, º) top

Pb1—O1	2.262 (3)	Pb1—N1	2.507 (3)

O1—Pb1—O1ⁱ	93.6 (2)	N1—Pb1—N1ⁱ	135.6 (1)

Symmetry code: (i) −x+1, y, −z+3/2.

Acknowledgements

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

References

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