catena-Poly[[(1,10-phenanthroline-5,6-dione-κ2N,N′)lead(II)]-μ-terephthalato-κ2O1:O4]

Cong, F.-D.; Yu, F.-Y.; Wei, Z.; Ng, S.W.

doi:10.1107/S1600536809046455

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page m1544

doi:10.1107/S1600536809046455

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catena-Poly[[(1,10-phenanthroline-5,6-dione-κ²N,N′)lead(II)]-μ-terephthalato-κ²O¹:O⁴]

Fang-Di Cong,^a ^* Feng-Yang Yu,^a Zhen Wei ^a and Seik Weng Ng ^b

^aDepartment of Basic Science, Tianjin Agricultural University, Tjianjin 300384, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: congfangdi666@yahoo.com.cn

(Received 1 November 2009; accepted 4 November 2009; online 7 November 2009)

The Pb^II atom in the polymeric title compound, [Pb(C₈H₄O₄)(C₁₂H₆N₂O₂)]_n, is chelated by the N-heterocycle, and adjacent atoms are bridged by rigid terephthalate dianions into a linear chain. The Pb^II atom is stereochemically active in a ψ-square-pyramidal coordination geometry in which the lone-pair electrons occupy a basal site. When three other weaker Pb⋯O interactions are considered, the geometry is a ψ-dodecahedron.

Related literature

For the crystal structure of lead(II) terephthalate, see: Tan et al. (2009 ).

Experimental

Crystal data

[Pb(C₈H₄O₄)(C₁₂H₆N₂O₂)]
M_r = 581.49
Monoclinic, P 2₁ /c
a = 10.428 (1) Å
b = 15.187 (1) Å
c = 11.478 (3) Å
β = 114.444 (1)°
V = 1654.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 10.24 mm⁻¹
T = 295 K
0.24 × 0.22 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.193, T_max = 0.234
8875 measured reflections
3233 independent reflections
2369 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.086
S = 1.00
3233 reflections
262 parameters
H-atom parameters constrained
Δρ_max = 1.94 e Å⁻³
Δρ_min = −0.95 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—O1	2.410 (6)
Pb1—O2	3.211 (5)
Pb1—O2ⁱ	3.176 (6)
Pb1—O3ⁱⁱ	2.301 (5)
Pb1—O4ⁱⁱ	2.910 (5)
Pb1—N1	2.535 (6)
Pb1—N2	2.626 (6)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046455/ci2964sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046455/ci2964Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of lead(II) terephthalate, see: Tan et al. (2009).

Experimental top

Lead nitrate (0.5 mmol, 0.166 g), terephthalic acid (0.5 mmol, 0.083 g) and phenanthrene-9,10-dione (0.5 mmol, 0.104 g) in water (12 ml) were heated at 443 K for 3 days in a Teflon-lined, stainless-steel Parr bomb. The bomb was slowly cooled to room temperature after which crystals were collected in 40% yield.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2009).

Figures top

	Fig. 1. Displacement ellipsoid plot (Barbour, 2001) of a part of the polymeric Pb(C₈H₄O₂)(C₁₂H₆N₂O₂) chain at the 70% probability level; H atoms are drawn as spheres of arbitrary radius. Symmetry code: (i) 2-x, 1/2+y, 3/2-z.
	Fig. 2. Detail of the polyhedron surrounding the lead atom. Symmetry codes: (i) 1-x, 1-y, 1-z; (ii) 2-x, 1/2+y, 3/2-z.

catena-Poly[[(1,10-phenanthroline-5,6-dione- κ²N,N')lead(II)]-µ-terephthalato-κ²O¹:O⁴] top

Crystal data top

[Pb(C₈H₄O₄)(C₁₂H₆N₂O₂)]	F(000) = 1096
M_r = 581.49	D_x = 2.334 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2807 reflections
a = 10.428 (1) Å	θ = 2.4–25.4°
b = 15.187 (1) Å	µ = 10.24 mm⁻¹
c = 11.478 (3) Å	T = 295 K
β = 114.444 (1)°	Block, yellow
V = 1654.8 (5) Å³	0.24 × 0.22 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3233 independent reflections
Radiation source: fine-focus sealed tube	2369 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→7
T_min = 0.193, T_max = 0.234	k = −18→18
8875 measured reflections	l = −12→14

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0491P)²] where P = (F_o² + 2F_c²)/3
3233 reflections	(Δ/σ)_max = 0.001
262 parameters	Δρ_max = 1.94 e Å⁻³
0 restraints	Δρ_min = −0.95 e Å⁻³

Crystal data top

[Pb(C₈H₄O₄)(C₁₂H₆N₂O₂)]	V = 1654.8 (5) Å³
M_r = 581.49	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.428 (1) Å	µ = 10.24 mm⁻¹
b = 15.187 (1) Å	T = 295 K
c = 11.478 (3) Å	0.24 × 0.22 × 0.20 mm
β = 114.444 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	3233 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2369 reflections with I > 2σ(I)
T_min = 0.193, T_max = 0.234	R_int = 0.036
8875 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.086	H-atom parameters constrained
S = 1.00	Δρ_max = 1.94 e Å⁻³
3233 reflections	Δρ_min = −0.95 e Å⁻³
262 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	0.60601 (3)	0.525108 (19)	0.39442 (2)	0.02978 (11)
O1	0.8123 (7)	0.4460 (4)	0.5353 (5)	0.0548 (17)
O2	0.7155 (6)	0.4344 (4)	0.6715 (5)	0.0489 (15)
O3	1.2513 (6)	0.1473 (4)	1.0397 (5)	0.0434 (14)
O4	1.3459 (6)	0.1510 (4)	0.9005 (5)	0.0414 (14)
O5	0.7884 (6)	0.5551 (4)	−0.1400 (5)	0.0396 (14)
O6	0.5419 (6)	0.6582 (4)	−0.2269 (4)	0.0401 (14)
N1	0.7358 (7)	0.4976 (4)	0.2537 (6)	0.0313 (15)
N2	0.5139 (6)	0.6109 (4)	0.1764 (5)	0.0273 (14)
C1	0.8093 (8)	0.4176 (5)	0.6363 (6)	0.0274 (16)
C2	0.9298 (7)	0.3592 (5)	0.7180 (6)	0.0269 (16)
C3	0.9398 (8)	0.3284 (5)	0.8348 (6)	0.0328 (18)
H3	0.8732	0.3456	0.8647	0.039*
C4	1.0481 (8)	0.2719 (5)	0.9082 (6)	0.0307 (17)
H4	1.0530	0.2514	0.9862	0.037*
C5	1.1492 (8)	0.2459 (4)	0.8653 (6)	0.0250 (15)
C6	1.1423 (8)	0.2799 (5)	0.7518 (6)	0.0266 (16)
H6	1.2107	0.2642	0.7234	0.032*
C7	1.0367 (8)	0.3362 (4)	0.6798 (6)	0.0279 (17)
H7	1.0359	0.3595	0.6046	0.033*
C8	1.2578 (8)	0.1772 (5)	0.9386 (7)	0.0274 (16)
C9	0.8489 (9)	0.4464 (5)	0.2881 (7)	0.039 (2)
H9	0.8807	0.4198	0.3681	0.047*
C10	0.9226 (8)	0.4296 (6)	0.2157 (7)	0.0373 (19)
H10	1.0007	0.3927	0.2460	0.045*
C11	0.8796 (8)	0.4678 (5)	0.0993 (7)	0.0353 (18)
H11	0.9284	0.4576	0.0487	0.042*
C12	0.7620 (7)	0.5226 (5)	0.0555 (6)	0.0253 (15)
C13	0.7110 (8)	0.5659 (5)	−0.0684 (6)	0.0291 (17)
C14	0.5958 (8)	0.6182 (5)	−0.1084 (6)	0.0294 (16)
C15	0.5252 (8)	0.6348 (5)	−0.0279 (6)	0.0275 (16)
C16	0.4105 (8)	0.6930 (5)	−0.0603 (7)	0.0371 (19)
H16	0.3745	0.7208	−0.1397	0.044*
C17	0.3523 (9)	0.7087 (5)	0.0235 (7)	0.041 (2)
H17	0.2778	0.7481	0.0027	0.049*
C18	0.4045 (8)	0.6657 (5)	0.1401 (7)	0.0354 (19)
H18	0.3614	0.6754	0.1956	0.042*
C19	0.5741 (7)	0.5947 (4)	0.0952 (6)	0.0230 (15)
C20	0.6907 (7)	0.5364 (4)	0.1342 (6)	0.0237 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.02839 (17)	0.03876 (18)	0.02215 (15)	−0.00225 (15)	0.01043 (12)	0.00065 (13)
O1	0.044 (4)	0.090 (5)	0.032 (3)	0.022 (3)	0.018 (3)	0.020 (3)
O2	0.045 (4)	0.067 (4)	0.043 (3)	0.017 (3)	0.026 (3)	0.012 (3)
O3	0.054 (4)	0.050 (3)	0.032 (3)	0.017 (3)	0.024 (3)	0.012 (3)
O4	0.039 (3)	0.055 (4)	0.035 (3)	0.011 (3)	0.020 (3)	0.009 (3)
O5	0.037 (3)	0.060 (4)	0.031 (3)	0.000 (3)	0.025 (3)	0.000 (3)
O6	0.040 (3)	0.058 (4)	0.022 (3)	0.007 (3)	0.012 (3)	0.012 (2)
N1	0.031 (4)	0.031 (3)	0.030 (3)	0.007 (3)	0.012 (3)	0.007 (2)
N2	0.029 (4)	0.030 (3)	0.024 (3)	0.000 (3)	0.013 (3)	−0.001 (2)
C1	0.030 (4)	0.031 (4)	0.020 (4)	−0.003 (3)	0.010 (3)	−0.005 (3)
C2	0.023 (4)	0.031 (4)	0.020 (4)	0.000 (3)	0.002 (3)	−0.001 (3)
C3	0.032 (4)	0.048 (5)	0.019 (4)	0.006 (4)	0.011 (3)	0.002 (3)
C4	0.035 (4)	0.038 (4)	0.019 (4)	0.001 (4)	0.011 (3)	0.007 (3)
C5	0.030 (4)	0.023 (4)	0.023 (4)	−0.005 (3)	0.012 (3)	−0.004 (3)
C6	0.028 (4)	0.036 (4)	0.019 (3)	0.001 (3)	0.013 (3)	0.001 (3)
C7	0.032 (4)	0.030 (4)	0.021 (4)	0.000 (3)	0.011 (3)	0.004 (3)
C8	0.028 (4)	0.029 (4)	0.025 (4)	−0.005 (3)	0.012 (3)	−0.004 (3)
C9	0.042 (5)	0.044 (5)	0.028 (4)	0.013 (4)	0.010 (4)	0.005 (3)
C10	0.031 (4)	0.049 (5)	0.031 (4)	0.007 (4)	0.012 (4)	0.006 (4)
C11	0.035 (5)	0.038 (4)	0.038 (4)	0.001 (4)	0.020 (4)	−0.003 (4)
C12	0.024 (4)	0.031 (4)	0.022 (3)	0.000 (4)	0.011 (3)	−0.007 (3)
C13	0.030 (4)	0.035 (4)	0.023 (4)	−0.005 (4)	0.012 (3)	−0.010 (3)
C14	0.031 (4)	0.035 (4)	0.020 (3)	−0.009 (4)	0.009 (3)	−0.002 (3)
C15	0.023 (4)	0.034 (4)	0.021 (4)	−0.005 (3)	0.005 (3)	−0.001 (3)
C16	0.034 (5)	0.043 (5)	0.031 (4)	0.008 (4)	0.010 (4)	0.008 (4)
C17	0.041 (5)	0.042 (5)	0.036 (5)	0.011 (4)	0.014 (4)	0.012 (4)
C18	0.033 (5)	0.038 (4)	0.037 (5)	0.002 (4)	0.016 (4)	−0.008 (3)
C19	0.024 (4)	0.023 (3)	0.020 (3)	−0.007 (3)	0.007 (3)	−0.003 (3)
C20	0.020 (4)	0.030 (4)	0.017 (3)	−0.005 (3)	0.002 (3)	−0.005 (3)

Geometric parameters (Å, º) top

Pb1—O1	2.410 (6)	C5—C6	1.375 (9)
Pb1—O2	3.211 (5)	C5—C8	1.514 (10)
Pb1—O2ⁱ	3.176 (6)	C6—C7	1.369 (9)
Pb1—O3ⁱⁱ	2.301 (5)	C6—H6	0.93
Pb1—O4ⁱⁱ	2.910 (5)	C7—H7	0.93
Pb1—N1	2.535 (6)	C9—C10	1.369 (11)
Pb1—N2	2.626 (6)	C9—H9	0.93
O1—C1	1.249 (8)	C10—C11	1.352 (10)
O2—C1	1.230 (9)	C10—H10	0.93
O3—C8	1.273 (8)	C11—C12	1.392 (10)
O4—C8	1.235 (9)	C11—H11	0.93
O5—C13	1.380 (8)	C12—C20	1.403 (9)
O6—C14	1.379 (8)	C12—C13	1.453 (10)
N1—C9	1.329 (10)	C13—C14	1.352 (10)
N1—C20	1.384 (9)	C14—C15	1.423 (10)
N2—C18	1.332 (9)	C15—C16	1.408 (10)
N2—C19	1.345 (8)	C15—C19	1.425 (9)
C1—C2	1.507 (10)	C16—C17	1.354 (10)
C2—C3	1.382 (9)	C16—H16	0.93
C2—C7	1.401 (10)	C17—C18	1.383 (10)
C3—C4	1.390 (10)	C17—H17	0.93
C3—H3	0.93	C18—H18	0.93
C4—C5	1.392 (10)	C19—C20	1.419 (9)
C4—H4	0.93

O3ⁱⁱ—Pb1—O1	84.5 (2)	C7—C6—C5	121.3 (7)
O3ⁱⁱ—Pb1—N1	84.2 (2)	C7—C6—H6	119.3
O1—Pb1—N1	77.40 (19)	C5—C6—H6	119.3
O3ⁱⁱ—Pb1—N2	81.07 (18)	C6—C7—C2	120.8 (6)
O1—Pb1—N2	139.46 (19)	C6—C7—H7	119.6
N1—Pb1—N2	63.61 (19)	C2—C7—H7	119.6
O3ⁱⁱ—Pb1—O4ⁱⁱ	48.16 (16)	O4—C8—O3	122.4 (7)
O1—Pb1—O4ⁱⁱ	88.69 (19)	O4—C8—C5	121.3 (6)
N1—Pb1—O4ⁱⁱ	131.65 (18)	O3—C8—C5	116.3 (7)
N2—Pb1—O4ⁱⁱ	108.50 (17)	N1—C9—C10	125.5 (7)
O3ⁱⁱ—Pb1—O2ⁱ	113.41 (19)	N1—C9—H9	117.2
O1—Pb1—O2ⁱ	144.83 (17)	C10—C9—H9	117.2
N1—Pb1—O2ⁱ	132.01 (18)	C11—C10—C9	118.7 (8)
N2—Pb1—O2ⁱ	75.11 (16)	C11—C10—H10	120.7
O4ⁱⁱ—Pb1—O2ⁱ	82.96 (15)	C9—C10—H10	120.7
O3ⁱⁱ—Pb1—O2	95.96 (17)	C10—C11—C12	119.7 (7)
O1—Pb1—O2	43.00 (17)	C10—C11—H11	120.1
N1—Pb1—O2	119.73 (17)	C12—C11—H11	120.1
N2—Pb1—O2	175.42 (16)	C11—C12—C20	118.6 (6)
O4ⁱⁱ—Pb1—O2	66.98 (16)	C11—C12—C13	122.4 (6)
O2ⁱ—Pb1—O2	103.09 (13)	C20—C12—C13	119.0 (6)
C1—O1—Pb1	115.9 (5)	C14—C13—O5	121.6 (7)
C1—O2—Pb1	76.6 (4)	C14—C13—C12	120.9 (6)
C8—O3—Pb1ⁱⁱⁱ	108.4 (5)	O5—C13—C12	117.5 (6)
C9—N1—C20	116.0 (7)	C13—C14—O6	122.4 (7)
C9—N1—Pb1	123.3 (5)	C13—C14—C15	120.6 (7)
C20—N1—Pb1	120.6 (5)	O6—C14—C15	117.0 (7)
C18—N2—C19	118.9 (6)	C16—C15—C14	123.4 (7)
C18—N2—Pb1	122.4 (5)	C16—C15—C19	116.6 (7)
C19—N2—Pb1	118.6 (4)	C14—C15—C19	119.9 (7)
O2—C1—O1	124.2 (7)	C17—C16—C15	120.3 (7)
O2—C1—C2	119.3 (6)	C17—C16—H16	119.9
O1—C1—C2	116.5 (7)	C15—C16—H16	119.9
C3—C2—C7	117.9 (7)	C16—C17—C18	119.5 (8)
C3—C2—C1	120.8 (7)	C16—C17—H17	120.3
C7—C2—C1	121.2 (6)	C18—C17—H17	120.3
C2—C3—C4	120.8 (7)	N2—C18—C17	122.7 (7)
C2—C3—H3	119.6	N2—C18—H18	118.7
C4—C3—H3	119.6	C17—C18—H18	118.7
C3—C4—C5	120.4 (6)	N2—C19—C20	118.7 (6)
C3—C4—H4	119.8	N2—C19—C15	122.0 (6)
C5—C4—H4	119.8	C20—C19—C15	119.2 (6)
C6—C5—C4	118.5 (7)	N1—C20—C12	121.4 (6)
C6—C5—C8	121.3 (7)	N1—C20—C19	118.3 (6)
C4—C5—C8	120.1 (6)	C12—C20—C19	120.2 (6)

O3ⁱⁱ—Pb1—O1—C1	108.0 (6)	Pb1ⁱⁱⁱ—O3—C8—O4	−10.9 (9)
N1—Pb1—O1—C1	−166.8 (6)	Pb1ⁱⁱⁱ—O3—C8—C5	167.9 (5)
N2—Pb1—O1—C1	177.4 (5)	C6—C5—C8—O4	1.9 (11)
O4ⁱⁱ—Pb1—O1—C1	59.9 (6)	C4—C5—C8—O4	177.7 (7)
O2ⁱ—Pb1—O1—C1	−15.9 (8)	C6—C5—C8—O3	−177.0 (7)
O2—Pb1—O1—C1	3.2 (5)	C4—C5—C8—O3	−1.2 (10)
O3ⁱⁱ—Pb1—O2—C1	−78.4 (5)	C20—N1—C9—C10	0.1 (12)
O1—Pb1—O2—C1	−3.0 (5)	Pb1—N1—C9—C10	−179.9 (7)
N1—Pb1—O2—C1	8.3 (5)	N1—C9—C10—C11	0.4 (13)
O4ⁱⁱ—Pb1—O2—C1	−117.8 (5)	C9—C10—C11—C12	−0.3 (12)
O2ⁱ—Pb1—O2—C1	165.8 (5)	C10—C11—C12—C20	−0.2 (11)
O3ⁱⁱ—Pb1—N1—C9	93.9 (6)	C10—C11—C12—C13	179.7 (7)
O1—Pb1—N1—C9	8.2 (6)	C11—C12—C13—C14	179.5 (7)
N2—Pb1—N1—C9	176.8 (7)	C20—C12—C13—C14	−0.6 (11)
O4ⁱⁱ—Pb1—N1—C9	84.9 (6)	C11—C12—C13—O5	−3.7 (10)
O2ⁱ—Pb1—N1—C9	−149.6 (6)	C20—C12—C13—O5	176.2 (6)
O2—Pb1—N1—C9	0.3 (7)	O5—C13—C14—O6	5.3 (11)
O3ⁱⁱ—Pb1—N1—C20	−86.2 (5)	C12—C13—C14—O6	−178.0 (6)
O1—Pb1—N1—C20	−171.9 (6)	O5—C13—C14—C15	−174.1 (6)
N2—Pb1—N1—C20	−3.3 (5)	C12—C13—C14—C15	2.6 (11)
O4ⁱⁱ—Pb1—N1—C20	−95.2 (5)	C13—C14—C15—C16	175.8 (7)
O2ⁱ—Pb1—N1—C20	30.3 (6)	O6—C14—C15—C16	−3.7 (11)
O2—Pb1—N1—C20	−179.7 (5)	C13—C14—C15—C19	−1.4 (11)
O3ⁱⁱ—Pb1—N2—C18	−92.5 (6)	O6—C14—C15—C19	179.2 (6)
O1—Pb1—N2—C18	−163.1 (5)	C14—C15—C16—C17	−177.0 (8)
N1—Pb1—N2—C18	179.6 (6)	C19—C15—C16—C17	0.2 (11)
O4ⁱⁱ—Pb1—N2—C18	−52.4 (6)	C15—C16—C17—C18	−1.4 (13)
O2ⁱ—Pb1—N2—C18	24.8 (5)	C19—N2—C18—C17	−1.9 (11)
O3ⁱⁱ—Pb1—N2—C19	91.7 (5)	Pb1—N2—C18—C17	−177.6 (6)
O1—Pb1—N2—C19	21.1 (6)	C16—C17—C18—N2	2.3 (13)
N1—Pb1—N2—C19	3.8 (5)	C18—N2—C19—C20	180.0 (6)
O4ⁱⁱ—Pb1—N2—C19	131.8 (5)	Pb1—N2—C19—C20	−4.1 (8)
O2ⁱ—Pb1—N2—C19	−151.0 (5)	C18—N2—C19—C15	0.5 (10)
Pb1—O2—C1—O1	4.8 (7)	Pb1—N2—C19—C15	176.5 (5)
Pb1—O2—C1—C2	−175.3 (6)	C16—C15—C19—N2	0.3 (10)
Pb1—O1—C1—O2	−6.9 (10)	C14—C15—C19—N2	177.6 (6)
Pb1—O1—C1—C2	173.2 (5)	C16—C15—C19—C20	−179.1 (6)
O2—C1—C2—C3	−3.5 (11)	C14—C15—C19—C20	−1.8 (10)
O1—C1—C2—C3	176.5 (7)	C9—N1—C20—C12	−0.7 (10)
O2—C1—C2—C7	178.1 (7)	Pb1—N1—C20—C12	179.4 (5)
O1—C1—C2—C7	−1.9 (10)	C9—N1—C20—C19	−177.3 (7)
C7—C2—C3—C4	−3.9 (11)	Pb1—N1—C20—C19	2.7 (8)
C1—C2—C3—C4	177.6 (7)	C11—C12—C20—N1	0.7 (10)
C2—C3—C4—C5	0.5 (11)	C13—C12—C20—N1	−179.2 (6)
C3—C4—C5—C6	2.4 (10)	C11—C12—C20—C19	177.3 (6)
C3—C4—C5—C8	−173.6 (7)	C13—C12—C20—C19	−2.6 (10)
C4—C5—C6—C7	−1.7 (10)	N2—C19—C20—N1	1.0 (9)
C8—C5—C6—C7	174.2 (6)	C15—C19—C20—N1	−179.5 (6)
C5—C6—C7—C2	−1.8 (11)	N2—C19—C20—C12	−175.7 (6)
C3—C2—C7—C6	4.6 (11)	C15—C19—C20—C12	3.8 (9)
C1—C2—C7—C6	−177.0 (6)

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

Experimental details

Crystal data
Chemical formula	[Pb(C₈H₄O₄)(C₁₂H₆N₂O₂)]
M_r	581.49
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.428 (1), 15.187 (1), 11.478 (3)
β (°)	114.444 (1)
V (Å³)	1654.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.24
Crystal size (mm)	0.24 × 0.22 × 0.20

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.193, 0.234
No. of measured, independent and observed [I > 2σ(I)] reflections	8875, 3233, 2369
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.086, 1.00
No. of reflections	3233
No. of parameters	262
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.94, −0.95

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Pb1—O1	2.410 (6)	Pb1—O4ⁱⁱ	2.910 (5)
Pb1—O2	3.211 (5)	Pb1—N1	2.535 (6)
Pb1—O2ⁱ	3.176 (6)	Pb1—N2	2.626 (6)
Pb1—O3ⁱⁱ	2.301 (5)

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

Acknowledgements

The authors thank Tianjin Agricultural University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, Y.-X., Meng, F.-Y., Wu, M.-C. & Zeng, M.-H. (2009). J. Mol. Struct. 928, 176–181. Web of Science CSD CrossRef CAS Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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