Bis(quinoline-2-carboxyl­ato-κ2N,O)lead(II)

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

doi:10.1107/S1600536810027509

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m946

https://doi.org/10.1107/S1600536810027509

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Bis(quinoline-2-carboxylato-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 11 July 2010; accepted 11 July 2010; online 17 July 2010)

The Pb^II atom in the title compound, [Pb(C₁₀H₆NO₂)₂], is N,O-chelated by two quinoline-2-carboxylate anions in a distorted Ψ-trigonal–bipyramidal environment; four atoms are connected to the Pb^II atom by regular coordination bonds. The structure also features two somewhat long Pb⋯O interactions [2.952 (3) and 3.014 (3) Å]. These long interactions give rise to a layer coordination polymer having the lead atom in a distorted Ψ-monocapped octahedral geometry.

Related literature

For a related structure, see: Zhang et al. (2007 ).

Experimental

Crystal data

[Pb(C₁₀H₆NO₂)₂]
M_r = 551.51
Monoclinic, P 2₁ /c
a = 16.4510 (15) Å
b = 7.2895 (7) Å
c = 14.1877 (13) Å
β = 108.981 (1)°
V = 1608.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 10.52 mm⁻¹
T = 100 K
0.15 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.301, T_max = 0.621
9758 measured reflections
3669 independent reflections
3119 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.058
S = 1.03
3669 reflections
244 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 1.64 e Å⁻³
Δρ_min = −0.93 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—O1	2.304 (3)
Pb1—O2ⁱ	2.952 (3)
Pb1—O3	2.295 (3)
Pb1—O4ⁱⁱ	3.014 (3)
Pb1—N1	2.567 (4)
Pb1—N2	2.531 (4)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) x, y-1, z.

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/S1600536810027509/xu2797sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810027509/xu2797Isup2.hkl

checkCIF report

Comment top

The lone-pair of electrons in lead(II) compounds is usually stereochemically active but the interpretation of the geometry when longer interactions are taken into account is, on the other hand, not usually so rigorous. Lead bis(quinoline-2-carboxylate) crystallizes as a DMSO-coordinated monohydrate but there is no mention of the geometry (Zhang et al., 2007). An examination of the published figure suggests a Ψ-octahedral arrangement.

In the title anhydrous compound (Scheme I, Fig. 1), the lead atom is N,O-chelated by the carboxylate anions in a Ψ-trigonal bipyramidal environment. However, when two other weaker interactions are considered, the lead atom the exists in a Ψ-monocapped octahedral geometry (Fig. 2).

Related literature top

For a related structure, see: Zhang et al. (2007).

Experimental top

Lead(II) acetate (1 mmol, 0.38 g), quinoline-2-carboxylic acid (1 mmol, 0.17 g) and sodium nitrite (1 mmol, 0.07 g) were loaded into one arm of a convection tube and both of the arms were filled slowly by methanol. The chemical-bearing arm was immersed in an oil bath kept at 333 K. Crystals were formed on the inside surface of the arm kept at room temperature after a week.

Structure description top

For a related structure, see: Zhang et al. (2007).

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. Thermal ellipsoid plot (Barbour, 2001) of the molecule of Pb(C₁₀H₆NO₂)₂ depicted as a part of a layer at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. Details of the Pb···O interactions are given in Table 1.
	Fig. 2. Ψ-Monocapped octahedral geometry of lead. Symmetry codes are given in Table 1.

Bis(quinoline-2-carboxylato-κ²N,O)lead(II) top

Crystal data top

[Pb(C₁₀H₆NO₂)₂]	F(000) = 1040
M_r = 551.51	D_x = 2.277 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3819 reflections
a = 16.4510 (15) Å	θ = 2.6–28.3°
b = 7.2895 (7) Å	µ = 10.52 mm⁻¹
c = 14.1877 (13) Å	T = 100 K
β = 108.981 (1)°	Prism, colorless
V = 1608.9 (3) Å³	0.15 × 0.10 × 0.05 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	3669 independent reflections
Radiation source: fine-focus sealed tube	3119 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.5°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→21
T_min = 0.301, T_max = 0.621	k = −8→9
9758 measured reflections	l = −18→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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.058	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0278P)² + 0.2749P] where P = (F_o² + 2F_c²)/3
3669 reflections	(Δ/σ)_max = 0.002
244 parameters	Δρ_max = 1.64 e Å⁻³
6 restraints	Δρ_min = −0.93 e Å⁻³

Crystal data top

[Pb(C₁₀H₆NO₂)₂]	V = 1608.9 (3) Å³
M_r = 551.51	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 16.4510 (15) Å	µ = 10.52 mm⁻¹
b = 7.2895 (7) Å	T = 100 K
c = 14.1877 (13) Å	0.15 × 0.10 × 0.05 mm
β = 108.981 (1)°

Data collection top

Bruker SMART APEX diffractometer	3669 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3119 reflections with I > 2σ(I)
T_min = 0.301, T_max = 0.621	R_int = 0.033
9758 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	6 restraints
wR(F²) = 0.058	H-atom parameters constrained
S = 1.03	Δρ_max = 1.64 e Å⁻³
3669 reflections	Δρ_min = −0.93 e Å⁻³
244 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	0.747914 (11)	0.70412 (2)	0.535665 (12)	0.00980 (6)
O1	0.7953 (2)	0.6837 (4)	0.4000 (2)	0.0147 (7)
O2	0.7691 (2)	0.6491 (5)	0.2362 (2)	0.0184 (7)
O3	0.7075 (2)	1.0028 (4)	0.4949 (2)	0.0144 (7)
O4	0.7419 (2)	1.2990 (4)	0.4913 (3)	0.0196 (7)
N1	0.6232 (2)	0.6704 (5)	0.3714 (3)	0.0107 (8)
N2	0.8766 (2)	0.9163 (5)	0.5793 (3)	0.0114 (8)
C1	0.7447 (3)	0.6590 (6)	0.3111 (3)	0.0126 (10)
C2	0.6487 (3)	0.6425 (6)	0.2937 (3)	0.0103 (9)
C3	0.5919 (3)	0.6023 (6)	0.1978 (3)	0.0131 (9)
H3	0.6131	0.5808	0.1439	0.016*
C4	0.5058 (3)	0.5948 (6)	0.1835 (3)	0.0138 (9)
H4	0.4663	0.5701	0.1191	0.017*
C5	0.4753 (3)	0.6238 (6)	0.2649 (3)	0.0136 (9)
C6	0.3874 (3)	0.6160 (6)	0.2565 (3)	0.0155 (10)
H6	0.3456	0.5914	0.1936	0.019*
C7	0.3621 (3)	0.6437 (6)	0.3383 (4)	0.0176 (10)
H7	0.3029	0.6358	0.3320	0.021*
C8	0.4233 (3)	0.6839 (6)	0.4319 (4)	0.0159 (10)
H8	0.4049	0.7041	0.4880	0.019*
C9	0.5090 (3)	0.6940 (6)	0.4427 (3)	0.0152 (10)
H9	0.5496	0.7228	0.5058	0.018*
C10	0.5372 (3)	0.6615 (6)	0.3599 (3)	0.0087 (9)
C11	0.7614 (3)	1.1369 (6)	0.5093 (3)	0.0134 (10)
C12	0.8565 (3)	1.0885 (6)	0.5515 (3)	0.0104 (9)
C13	0.9195 (3)	1.2240 (6)	0.5577 (3)	0.0138 (10)
H13	0.9031	1.3456	0.5356	0.017*
C14	1.0048 (3)	1.1769 (6)	0.5963 (3)	0.0146 (10)
H14	1.0480	1.2657	0.6002	0.018*
C15	1.0278 (3)	0.9972 (6)	0.6300 (3)	0.0126 (9)
C16	1.1143 (3)	0.9387 (6)	0.6713 (3)	0.0155 (10)
H16	1.1597	1.0243	0.6805	0.019*
C17	1.1325 (3)	0.7599 (7)	0.6981 (3)	0.0169 (10)
H17	1.1907	0.7213	0.7233	0.020*
C18	1.0664 (3)	0.6316 (7)	0.6888 (3)	0.0141 (10)
H18	1.0803	0.5082	0.7093	0.017*
C19	0.9823 (3)	0.6841 (6)	0.6505 (3)	0.0136 (10)
H19	0.9379	0.5973	0.6446	0.016*
C20	0.9612 (3)	0.8672 (6)	0.6195 (3)	0.0093 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.00792 (9)	0.01030 (9)	0.01183 (8)	−0.00087 (7)	0.00412 (6)	0.00058 (7)
O1	0.0075 (17)	0.0208 (19)	0.0172 (16)	−0.0020 (14)	0.0061 (13)	−0.0022 (13)
O2	0.0192 (19)	0.0226 (18)	0.0175 (16)	0.0033 (15)	0.0117 (14)	−0.0028 (14)
O3	0.0095 (17)	0.0113 (17)	0.0208 (16)	−0.0028 (14)	0.0028 (14)	−0.0009 (13)
O4	0.020 (2)	0.0117 (17)	0.0315 (19)	0.0039 (15)	0.0149 (15)	0.0054 (15)
N1	0.012 (2)	0.0061 (18)	0.0169 (18)	−0.0005 (15)	0.0080 (16)	0.0009 (14)
N2	0.014 (2)	0.0097 (19)	0.0115 (17)	−0.0021 (16)	0.0052 (15)	−0.0014 (14)
C1	0.013 (3)	0.008 (2)	0.020 (2)	0.0001 (18)	0.009 (2)	0.0037 (17)
C2	0.007 (2)	0.006 (2)	0.017 (2)	0.0002 (17)	0.0025 (18)	0.0001 (16)
C3	0.014 (2)	0.013 (2)	0.013 (2)	−0.0032 (19)	0.0045 (18)	−0.0013 (18)
C4	0.015 (3)	0.007 (2)	0.015 (2)	−0.0004 (19)	−0.0009 (18)	0.0007 (17)
C5	0.014 (3)	0.010 (2)	0.016 (2)	0.000 (2)	0.0039 (19)	0.0010 (18)
C6	0.012 (3)	0.013 (2)	0.019 (2)	0.001 (2)	0.0007 (19)	0.0007 (19)
C7	0.010 (3)	0.015 (2)	0.026 (3)	0.000 (2)	0.004 (2)	0.0054 (19)
C8	0.013 (3)	0.012 (2)	0.023 (2)	0.001 (2)	0.007 (2)	0.0040 (19)
C9	0.014 (3)	0.013 (2)	0.016 (2)	0.001 (2)	0.0012 (19)	0.0003 (18)
C10	0.005 (2)	0.005 (2)	0.014 (2)	−0.0006 (16)	0.0015 (17)	0.0007 (15)
C11	0.017 (3)	0.013 (2)	0.012 (2)	0.005 (2)	0.0062 (19)	0.0029 (17)
C12	0.013 (2)	0.012 (2)	0.0087 (19)	0.0034 (18)	0.0066 (17)	−0.0013 (16)
C13	0.019 (3)	0.008 (2)	0.014 (2)	0.001 (2)	0.0065 (19)	0.0034 (17)
C14	0.015 (3)	0.013 (2)	0.017 (2)	−0.0075 (19)	0.0074 (19)	−0.0052 (18)
C15	0.014 (2)	0.013 (2)	0.013 (2)	−0.0028 (19)	0.0073 (18)	−0.0023 (17)
C16	0.010 (2)	0.017 (2)	0.020 (2)	−0.0033 (19)	0.0052 (19)	−0.0039 (19)
C17	0.012 (3)	0.021 (3)	0.016 (2)	0.004 (2)	0.0020 (19)	−0.0007 (18)
C18	0.012 (3)	0.015 (2)	0.015 (2)	0.001 (2)	0.0041 (19)	0.0008 (18)
C19	0.013 (2)	0.014 (2)	0.013 (2)	−0.003 (2)	0.0024 (18)	−0.0011 (18)
C20	0.007 (2)	0.013 (2)	0.0096 (19)	−0.0013 (18)	0.0049 (17)	−0.0030 (17)

Geometric parameters (Å, º) top

Pb1—O1	2.304 (3)	C6—H6	0.9500
Pb1—O2ⁱ	2.952 (3)	C7—C8	1.412 (7)
Pb1—O3	2.295 (3)	C7—H7	0.9500
Pb1—O4ⁱⁱ	3.014 (3)	C8—C9	1.370 (7)
Pb1—N1	2.567 (4)	C8—H8	0.9500
Pb1—N2	2.531 (4)	C9—C10	1.417 (6)
O1—C1	1.279 (6)	C9—H9	0.9500
O2—C1	1.255 (5)	C11—C12	1.525 (6)
O3—C11	1.290 (6)	C12—C13	1.413 (6)
O4—C11	1.229 (5)	C13—C14	1.373 (7)
N1—C2	1.318 (6)	C13—H13	0.9500
N1—C10	1.370 (6)	C14—C15	1.404 (6)
N2—C12	1.325 (5)	C14—H14	0.9500
N2—C20	1.368 (6)	C15—C16	1.417 (6)
C1—C2	1.521 (6)	C15—C20	1.419 (6)
C2—C3	1.408 (6)	C16—C17	1.363 (6)
C3—C4	1.366 (6)	C16—H16	0.9500
C3—H3	0.9500	C17—C18	1.408 (7)
C4—C5	1.416 (6)	C17—H17	0.9500
C4—H4	0.9500	C18—C19	1.366 (6)
C5—C6	1.413 (6)	C18—H18	0.9500
C5—C10	1.427 (6)	C19—C20	1.413 (6)
C6—C7	1.370 (6)	C19—H19	0.9500

O3—Pb1—O1	89.98 (11)	C6—C7—H7	119.8
O3—Pb1—N2	68.45 (11)	C8—C7—H7	119.8
O1—Pb1—N2	76.13 (11)	C9—C8—C7	120.6 (5)
O3—Pb1—N1	77.38 (11)	C9—C8—H8	119.7
O1—Pb1—N1	67.90 (11)	C7—C8—H8	119.7
N2—Pb1—N1	129.71 (11)	C8—C9—C10	120.1 (4)
O3—Pb1—O2ⁱ	80.37 (10)	C8—C9—H9	120.0
O1—Pb1—O2ⁱ	149.57 (10)	C10—C9—H9	120.0
N2—Pb1—O2ⁱ	73.48 (10)	N1—C10—C9	119.8 (4)
N1—Pb1—O2ⁱ	135.90 (11)	N1—C10—C5	120.9 (4)
O3—Pb1—O4ⁱⁱ	152.83 (10)	C9—C10—C5	119.3 (4)
O1—Pb1—O4ⁱⁱ	76.09 (10)	O4—C11—O3	125.2 (4)
N2—Pb1—O4ⁱⁱ	128.16 (11)	O4—C11—C12	118.0 (4)
N1—Pb1—O4ⁱⁱ	75.78 (10)	O3—C11—C12	116.8 (4)
O2ⁱ—Pb1—O4ⁱⁱ	122.81 (9)	N2—C12—C13	122.4 (4)
C1—O1—Pb1	122.9 (3)	N2—C12—C11	117.5 (4)
C11—O3—Pb1	123.4 (3)	C13—C12—C11	120.1 (4)
C2—N1—C10	119.3 (4)	C14—C13—C12	118.9 (4)
C2—N1—Pb1	113.3 (3)	C14—C13—H13	120.5
C10—N1—Pb1	127.0 (3)	C12—C13—H13	120.5
C12—N2—C20	119.6 (4)	C13—C14—C15	119.8 (4)
C12—N2—Pb1	113.4 (3)	C13—C14—H14	120.1
C20—N2—Pb1	126.7 (3)	C15—C14—H14	120.1
O2—C1—O1	123.9 (4)	C14—C15—C16	123.0 (4)
O2—C1—C2	117.3 (4)	C14—C15—C20	118.3 (4)
O1—C1—C2	118.8 (4)	C16—C15—C20	118.6 (4)
N1—C2—C3	123.3 (4)	C17—C16—C15	120.2 (4)
N1—C2—C1	116.6 (4)	C17—C16—H16	119.9
C3—C2—C1	120.1 (4)	C15—C16—H16	119.9
C4—C3—C2	118.8 (4)	C16—C17—C18	121.1 (5)
C4—C3—H3	120.6	C16—C17—H17	119.5
C2—C3—H3	120.6	C18—C17—H17	119.5
C3—C4—C5	119.9 (4)	C19—C18—C17	120.1 (5)
C3—C4—H4	120.0	C19—C18—H18	119.9
C5—C4—H4	120.0	C17—C18—H18	119.9
C6—C5—C4	123.3 (4)	C18—C19—C20	120.2 (4)
C6—C5—C10	119.0 (4)	C18—C19—H19	119.9
C4—C5—C10	117.8 (4)	C20—C19—H19	119.9
C7—C6—C5	120.5 (4)	N2—C20—C19	119.4 (4)
C7—C6—H6	119.7	N2—C20—C15	121.0 (4)
C5—C6—H6	119.7	C19—C20—C15	119.6 (4)
C6—C7—C8	120.5 (5)

O3—Pb1—O1—C1	−79.2 (3)	C4—C5—C6—C7	179.4 (5)
N2—Pb1—O1—C1	−147.0 (3)	C10—C5—C6—C7	−0.2 (7)
N1—Pb1—O1—C1	−2.8 (3)	C5—C6—C7—C8	1.2 (7)
O2ⁱ—Pb1—O1—C1	−149.9 (3)	C6—C7—C8—C9	−0.7 (7)
O4ⁱⁱ—Pb1—O1—C1	77.2 (3)	C7—C8—C9—C10	−0.9 (7)
O1—Pb1—O3—C11	−74.7 (3)	C2—N1—C10—C9	−179.1 (4)
N2—Pb1—O3—C11	0.4 (3)	Pb1—N1—C10—C9	7.8 (5)
N1—Pb1—O3—C11	−142.0 (3)	C2—N1—C10—C5	−0.4 (6)
O2ⁱ—Pb1—O3—C11	76.3 (3)	Pb1—N1—C10—C5	−173.5 (3)
O4ⁱⁱ—Pb1—O3—C11	−132.9 (3)	C8—C9—C10—N1	−179.5 (4)
O3—Pb1—N1—C2	100.8 (3)	C8—C9—C10—C5	1.9 (6)
O1—Pb1—N1—C2	5.6 (3)	C6—C5—C10—N1	−180.0 (4)
N2—Pb1—N1—C2	53.2 (3)	C4—C5—C10—N1	0.4 (6)
O2ⁱ—Pb1—N1—C2	162.2 (3)	C6—C5—C10—C9	−1.3 (6)
O4ⁱⁱ—Pb1—N1—C2	−75.0 (3)	C4—C5—C10—C9	179.1 (4)
O3—Pb1—N1—C10	−85.8 (3)	Pb1—O3—C11—O4	−177.6 (3)
O1—Pb1—N1—C10	179.0 (4)	Pb1—O3—C11—C12	2.8 (5)
N2—Pb1—N1—C10	−133.3 (3)	C20—N2—C12—C13	2.8 (6)
O2ⁱ—Pb1—N1—C10	−24.3 (4)	Pb1—N2—C12—C13	−172.1 (3)
O4ⁱⁱ—Pb1—N1—C10	98.5 (3)	C20—N2—C12—C11	−178.7 (3)
O3—Pb1—N2—C12	−3.8 (3)	Pb1—N2—C12—C11	6.5 (4)
O1—Pb1—N2—C12	91.8 (3)	O4—C11—C12—N2	173.9 (4)
N1—Pb1—N2—C12	46.9 (3)	O3—C11—C12—N2	−6.5 (6)
O2ⁱ—Pb1—N2—C12	−89.8 (3)	O4—C11—C12—C13	−7.6 (6)
O4ⁱⁱ—Pb1—N2—C12	151.2 (2)	O3—C11—C12—C13	172.1 (4)
O3—Pb1—N2—C20	−178.2 (3)	N2—C12—C13—C14	−1.7 (6)
O1—Pb1—N2—C20	−82.6 (3)	C11—C12—C13—C14	179.8 (4)
N1—Pb1—N2—C20	−127.5 (3)	C12—C13—C14—C15	−0.9 (7)
O2ⁱ—Pb1—N2—C20	95.9 (3)	C13—C14—C15—C16	−179.5 (4)
O4ⁱⁱ—Pb1—N2—C20	−23.2 (4)	C13—C14—C15—C20	2.3 (6)
Pb1—O1—C1—O2	179.4 (3)	C14—C15—C16—C17	−176.7 (4)
Pb1—O1—C1—C2	0.1 (5)	C20—C15—C16—C17	1.5 (6)
C10—N1—C2—C3	−0.4 (6)	C15—C16—C17—C18	−2.4 (7)
Pb1—N1—C2—C3	173.6 (3)	C16—C17—C18—C19	1.5 (7)
C10—N1—C2—C1	178.5 (4)	C17—C18—C19—C20	0.3 (7)
Pb1—N1—C2—C1	−7.5 (5)	C12—N2—C20—C19	179.0 (4)
O2—C1—C2—N1	−173.8 (4)	Pb1—N2—C20—C19	−6.9 (5)
O1—C1—C2—N1	5.5 (6)	C12—N2—C20—C15	−1.3 (6)
O2—C1—C2—C3	5.2 (6)	Pb1—N2—C20—C15	172.8 (3)
O1—C1—C2—C3	−175.5 (4)	C18—C19—C20—N2	178.6 (4)
N1—C2—C3—C4	1.2 (7)	C18—C19—C20—C15	−1.1 (6)
C1—C2—C3—C4	−177.7 (4)	C14—C15—C20—N2	−1.3 (6)
C2—C3—C4—C5	−1.1 (7)	C16—C15—C20—N2	−179.5 (4)
C3—C4—C5—C6	−179.2 (4)	C14—C15—C20—C19	178.5 (4)
C3—C4—C5—C10	0.4 (7)	C16—C15—C20—C19	0.2 (6)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[Pb(C₁₀H₆NO₂)₂]
M_r	551.51
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	16.4510 (15), 7.2895 (7), 14.1877 (13)
β (°)	108.981 (1)
V (Å³)	1608.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.52
Crystal size (mm)	0.15 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.301, 0.621
No. of measured, independent and observed [I > 2σ(I)] reflections	9758, 3669, 3119
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.058, 1.03
No. of reflections	3669
No. of parameters	244
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.64, −0.93

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

Selected bond lengths (Å) top

Pb1—O1	2.304 (3)	Pb1—O4ⁱⁱ	3.014 (3)
Pb1—O2ⁱ	2.952 (3)	Pb1—N1	2.567 (4)
Pb1—O3	2.295 (3)	Pb1—N2	2.531 (4)

Symmetry codes: (i) x, −y+3/2, z+1/2; (ii) x, y−1, z.

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

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