catena-Poly[[(1,10-phenanthroline)lead(II)]bis­(μ-5-chloro-2-hy­droxy­benzoato)]

Yang, L.; Li, B.; Xue, Q.; Huo, Y.; Wang, G.

doi:10.1107/S1600536810023561

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 8| August 2010| Page m987

https://doi.org/10.1107/S1600536810023561

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catena-Poly[[(1,10-phenanthroline)lead(II)]bis(μ-5-chloro-2-hydroxybenzoato)]

Lei Yang,^a ^* Bing Li,^b Qing Xue,^a Yu Huo ^a and Gaopeng Wang ^a

^aDepartment of Physics–Chemistry, Henan Polytechnic University, Jiao Zuo, 454150, People's Republic of China, and ^bDepartment of Chemistry, Zhejiang Forestry University, Lin'an, 311300, People's Republic of China
^*Correspondence e-mail: xcy78413@tom.com

(Received 27 May 2010; accepted 17 June 2010; online 21 July 2010)

In the title polymer, [Pb(C₇H₄ClO₃)₂(C₁₂H₈N₂)]_n, the Pb(II) ion displays a distorted pseudo-octahedral coordination geometry. The metal center is coordinated by six O atoms from four 5-chlorosalicylate ligands and two N atoms from a chelating phenanthroline ligand. The polymeric structure is built up from bridging carboxylate O atoms, forming chains along [100]. The crystal structure is stabilized by π–π interactions between the 1,10-phenanthroline and 5-chlorosalicylate ligands, the shortest centroid–centroid separation between neighbouring aromatic rings being 3.652 (1) Å.

Related literature

For related non-polymeric complexes including 5-chlorosalicylate ligands, see: Wen & Ying (2007 ); Wen et al. (2008 ).

Experimental

Crystal data

[Pb(C₇H₄ClO₃)₂(C₁₂H₈N₂)]
M_r = 730.51
Triclinic, $[P \overline 1]$
a = 8.9100 (1) Å
b = 11.2959 (1) Å
c = 13.5816 (1) Å
α = 75.508 (1)°
β = 86.302 (1)°
γ = 68.342 (1)°
V = 1229.43 (2) Å³
Z = 2
Mo Kα radiation
μ = 7.13 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.24 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.156, T_max = 0.181
21579 measured reflections
5987 independent reflections
5339 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.064
S = 1.05
5987 reflections
334 parameters
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810023561/bh2289sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810023561/bh2289Isup2.hkl

checkCIF report

Comment top

The Pb(II) ion in the asymmetric unit is pseudo-octahedrally coordinated (Fig. 1), with coordination to six O atoms from four 5-chlorosalicylate ligands, and two N atoms from a chelating phenanthroline (phen) ligand. Two related complexes, [Zn(C₇H₄ClO₃)₂(C₁₂H₈N₂)(H₂O)] and [Cd(C₇H₄ClO₃)₂(C₁₂H₈N₂)₂], were reported (Wen & Ying, 2007; Wen et al., 2008, respectively), both with 5-chlorosalicylate ions acting as monodentate ligands, while in the title polymer, 5-chlorosalicylate ions are bidentate ligands.

The Pb—O distances (Table 1) vary from 2.458 (3) to 2.887 (3) Å, which are close to those found in Pb₂(PMIDA).1.5H₂O [from 2.331 (9) to 2.876 (9) Å; H₄PMIDA is N-(phosphonomethyl)iminodiacetic acid]. Each pair of adjacent Pb(II) ions is bridged by the O1 atom of 5-chlorosalicylate, which forms a SBU (secondary building units, Fig. 2) including two Pb polyhedron, six 5-chlorosalicylate and two phen. The Pb···Pb distance in the dimeric unit is 4.3587 (2) Å. The SBU is bridged by O5 atom of 5-chlorosalicylate, to give rise to a zigzag chain (Fig. 3). The excellent coordinating ability and large conjugated systems of phen and 5-chlorosalicylate allow to form π···π interactions. The chains are extended into the framework through π..π interactions between the ligands from adjacent chains.

Related literature top

For related non-polymeric complexes including 5-chlorosalicylate ligands, see: Wen & Ying (2007); Wen et al. (2008).

Experimental top

The pH value of a mixture of Pb(NO₃)₂ (0.5 mmol), phen (0.5 mmol) and 5-chlorosalicylic acid (0.5 mmol) in 8 ml of distilled water and 16 ml of ethanol was adjusted between 5 and 6 by addition of sodium hydroxide. The resultant solution was refluxed for 6 h. After cooling, yellow crystals were formed over 2 days, at room temperature.

Structure description top

For related non-polymeric complexes including 5-chlorosalicylate ligands, see: Wen & Ying (2007); Wen et al. (2008).

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The Pb coordination geometry in the title compound, with thermal ellipsoids at the 50% probability level. Symmetry codes: A 1 - x, -y, -z; B: -x, -y, -z.
	Fig. 2. A section of the structure of the title complex showing SBU with shared corner O atoms.
	Fig. 3. The chain of the title polymer, viewed down the a axis.

catena-Poly[[(1,10-phenanthroline)lead(II)]bis(µ-5-chloro- 2-hydroxybenzoato)] top

Crystal data top

[Pb(C₇H₄ClO₃)₂(C₁₂H₈N₂)]	Z = 2
M_r = 730.51	F(000) = 700
Triclinic, P1	D_x = 1.973 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9100 (1) Å	Cell parameters from 5987 reflections
b = 11.2959 (1) Å	θ = 2.8–26.9°
c = 13.5816 (1) Å	µ = 7.13 mm⁻¹
α = 75.508 (1)°	T = 296 K
β = 86.302 (1)°	Block, yellow
γ = 68.342 (1)°	0.28 × 0.25 × 0.24 mm
V = 1229.43 (2) Å³

Data collection top

Bruker APEXII CCD diffractometer	5987 independent reflections
Radiation source: fine-focus sealed tube	5339 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 28.2°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.156, T_max = 0.181	k = −14→14
21579 measured reflections	l = −18→17

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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0349P)² + 0.472P] where P = (F_o² + 2F_c²)/3
5987 reflections	(Δ/σ)_max = 0.001
334 parameters	Δρ_max = 1.18 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³
0 constraints

Crystal data top

[Pb(C₇H₄ClO₃)₂(C₁₂H₈N₂)]	γ = 68.342 (1)°
M_r = 730.51	V = 1229.43 (2) Å³
Triclinic, P1	Z = 2
a = 8.9100 (1) Å	Mo Kα radiation
b = 11.2959 (1) Å	µ = 7.13 mm⁻¹
c = 13.5816 (1) Å	T = 296 K
α = 75.508 (1)°	0.28 × 0.25 × 0.24 mm
β = 86.302 (1)°

Data collection top

Bruker APEXII CCD diffractometer	5987 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5339 reflections with I > 2σ(I)
T_min = 0.156, T_max = 0.181	R_int = 0.029
21579 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	0 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 1.05	Δρ_max = 1.18 e Å⁻³
5987 reflections	Δρ_min = −0.59 e Å⁻³
334 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	0.258486 (14)	−0.038882 (12)	−0.001073 (10)	0.03675 (5)
Cl1	1.04796 (14)	−0.31797 (16)	0.36720 (10)	0.0779 (4)
Cl2	−0.2949 (2)	−0.0117 (2)	0.47404 (14)	0.1106 (6)
O5	0.0025 (3)	0.0001 (3)	0.1216 (2)	0.0495 (6)
O1	0.5607 (4)	−0.1240 (3)	0.0939 (2)	0.0548 (7)
O2	0.3533 (3)	−0.1567 (3)	0.1750 (2)	0.0569 (7)
O4	0.1160 (4)	0.1481 (3)	0.1053 (2)	0.0604 (8)
N1	0.2350 (4)	−0.2615 (3)	0.0256 (2)	0.0423 (7)
N2	0.4307 (4)	−0.1896 (3)	−0.1218 (3)	0.0449 (7)
C12	0.2979 (4)	−0.3371 (3)	−0.0407 (3)	0.0394 (8)
O3	0.3774 (4)	−0.2835 (5)	0.3602 (3)	0.0882 (13)
H3B	0.3326	−0.2436	0.3043	0.132*
C11	0.3981 (4)	−0.2980 (4)	−0.1197 (3)	0.0409 (8)
C13	0.5001 (4)	−0.1665 (3)	0.1727 (3)	0.0417 (8)
C14	0.5973 (4)	−0.2334 (4)	0.2701 (3)	0.0421 (8)
C15	0.5322 (5)	−0.2888 (6)	0.3575 (3)	0.0609 (12)
C7	0.4610 (5)	−0.3747 (4)	−0.1912 (3)	0.0509 (10)
C8	0.5574 (6)	−0.3329 (5)	−0.2661 (4)	0.0615 (12)
H8A	0.6005	−0.3804	−0.3148	0.074*
O6	0.0401 (4)	0.3062 (3)	0.2185 (3)	0.0704 (9)
H6B	0.0809	0.2756	0.1702	0.106*
C21	−0.0455 (4)	0.1217 (4)	0.2486 (3)	0.0419 (8)
C4	0.2689 (5)	−0.4538 (4)	−0.0344 (4)	0.0496 (9)
C1	0.1447 (5)	−0.2992 (4)	0.0995 (3)	0.0506 (9)
H1A	0.1000	−0.2465	0.1446	0.061*
C22	−0.0349 (5)	0.2293 (5)	0.2767 (3)	0.0512 (10)
C19	0.7579 (5)	−0.2452 (4)	0.2740 (3)	0.0449 (8)
H19A	0.8040	−0.2107	0.2160	0.054*
C20	0.0289 (4)	0.0873 (4)	0.1522 (3)	0.0447 (9)
C9	0.5890 (6)	−0.2234 (5)	−0.2688 (4)	0.0634 (12)
H9A	0.6523	−0.1946	−0.3191	0.076*
C2	0.1143 (6)	−0.4148 (5)	0.1118 (4)	0.0590 (11)
H2A	0.0533	−0.4396	0.1655	0.071*
C10	0.5239 (5)	−0.1554 (5)	−0.1941 (3)	0.0551 (10)
H10A	0.5475	−0.0814	−0.1952	0.066*
C26	−0.1257 (5)	0.0475 (4)	0.3101 (3)	0.0510 (9)
H26A	−0.1347	−0.0236	0.2916	0.061*
C3	0.1744 (6)	−0.4899 (4)	0.0450 (4)	0.0616 (12)
H3A	0.1529	−0.5660	0.0517	0.074*
C5	0.3351 (6)	−0.5275 (5)	−0.1086 (4)	0.0664 (13)
H5A	0.3147	−0.6033	−0.1054	0.080*
C6	0.4259 (6)	−0.4894 (5)	−0.1825 (4)	0.0660 (13)
H6A	0.4673	−0.5396	−0.2297	0.079*
C25	−0.1914 (6)	0.0793 (5)	0.3981 (3)	0.0638 (12)
C24	−0.1821 (6)	0.1881 (6)	0.4256 (4)	0.0740 (15)
H24A	−0.2285	0.2099	0.4851	0.089*
C23	−0.1051 (6)	0.2610 (6)	0.3650 (4)	0.0688 (13)
H23A	−0.0993	0.3335	0.3830	0.083*
C18	0.8483 (5)	−0.3069 (5)	0.3622 (3)	0.0616 (12)
C17	0.7827 (7)	−0.3620 (7)	0.4485 (4)	0.0867 (19)
H17A	0.8447	−0.4035	0.5085	0.104*
C16	0.6277 (7)	−0.3553 (7)	0.4453 (4)	0.090 (2)
H16A	0.5853	−0.3956	0.5025	0.108*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.03379 (8)	0.04199 (8)	0.03692 (8)	−0.01778 (5)	0.00344 (5)	−0.00846 (5)
Cl1	0.0494 (6)	0.1113 (10)	0.0641 (8)	−0.0373 (7)	−0.0139 (5)	0.0104 (7)
Cl2	0.1064 (12)	0.1390 (15)	0.0809 (10)	−0.0634 (11)	0.0396 (9)	0.0020 (10)
O5	0.0489 (15)	0.0541 (15)	0.0449 (16)	−0.0154 (13)	−0.0012 (12)	−0.0156 (13)
O1	0.0612 (18)	0.0596 (17)	0.0402 (16)	−0.0272 (15)	−0.0072 (13)	0.0037 (13)
O2	0.0420 (15)	0.0743 (19)	0.0543 (18)	−0.0233 (14)	−0.0065 (13)	−0.0106 (15)
O4	0.0583 (18)	0.072 (2)	0.0588 (19)	−0.0311 (16)	0.0224 (15)	−0.0228 (16)
N1	0.0386 (16)	0.0421 (15)	0.0465 (18)	−0.0169 (13)	0.0001 (13)	−0.0076 (13)
N2	0.0396 (16)	0.0503 (18)	0.0479 (19)	−0.0189 (14)	0.0051 (14)	−0.0144 (15)
C12	0.0337 (17)	0.0355 (17)	0.044 (2)	−0.0068 (14)	−0.0094 (15)	−0.0072 (14)
O3	0.054 (2)	0.168 (4)	0.055 (2)	−0.063 (2)	0.0100 (16)	−0.016 (2)
C11	0.0334 (17)	0.0426 (18)	0.043 (2)	−0.0090 (15)	−0.0082 (15)	−0.0089 (15)
C13	0.0431 (19)	0.0386 (18)	0.046 (2)	−0.0132 (15)	−0.0020 (16)	−0.0157 (16)
C14	0.0409 (19)	0.051 (2)	0.038 (2)	−0.0194 (16)	0.0004 (15)	−0.0123 (16)
C15	0.052 (2)	0.097 (4)	0.042 (2)	−0.037 (2)	0.0066 (19)	−0.017 (2)
C7	0.047 (2)	0.049 (2)	0.048 (2)	−0.0041 (17)	−0.0109 (18)	−0.0144 (18)
C8	0.059 (3)	0.073 (3)	0.045 (2)	−0.010 (2)	0.003 (2)	−0.023 (2)
O6	0.068 (2)	0.075 (2)	0.085 (3)	−0.0421 (18)	0.0217 (18)	−0.0284 (19)
C21	0.0324 (17)	0.054 (2)	0.0364 (19)	−0.0137 (16)	−0.0002 (14)	−0.0095 (16)
C4	0.050 (2)	0.0374 (19)	0.058 (2)	−0.0137 (17)	−0.0157 (19)	−0.0045 (17)
C1	0.050 (2)	0.051 (2)	0.050 (2)	−0.0226 (18)	0.0022 (18)	−0.0045 (18)
C22	0.038 (2)	0.065 (3)	0.052 (2)	−0.0196 (19)	0.0005 (17)	−0.016 (2)
C19	0.0416 (19)	0.052 (2)	0.039 (2)	−0.0193 (17)	0.0012 (16)	−0.0035 (16)
C20	0.0338 (18)	0.055 (2)	0.040 (2)	−0.0095 (16)	−0.0021 (15)	−0.0103 (17)
C9	0.053 (3)	0.079 (3)	0.055 (3)	−0.020 (2)	0.010 (2)	−0.017 (2)
C2	0.054 (2)	0.058 (3)	0.061 (3)	−0.029 (2)	0.000 (2)	0.005 (2)
C10	0.050 (2)	0.064 (3)	0.056 (3)	−0.026 (2)	0.014 (2)	−0.018 (2)
C26	0.044 (2)	0.061 (2)	0.046 (2)	−0.0218 (19)	0.0014 (17)	−0.0048 (18)
C3	0.061 (3)	0.046 (2)	0.078 (3)	−0.027 (2)	−0.011 (2)	−0.003 (2)
C5	0.072 (3)	0.045 (2)	0.085 (4)	−0.019 (2)	−0.014 (3)	−0.021 (2)
C6	0.073 (3)	0.054 (2)	0.069 (3)	−0.010 (2)	−0.007 (3)	−0.029 (2)
C25	0.052 (2)	0.088 (3)	0.043 (2)	−0.028 (2)	0.0101 (19)	0.000 (2)
C24	0.061 (3)	0.111 (4)	0.047 (3)	−0.022 (3)	0.012 (2)	−0.030 (3)
C23	0.065 (3)	0.087 (3)	0.063 (3)	−0.028 (3)	0.011 (2)	−0.036 (3)
C18	0.049 (2)	0.090 (3)	0.044 (2)	−0.033 (2)	−0.0051 (19)	−0.001 (2)
C17	0.068 (3)	0.146 (6)	0.042 (3)	−0.053 (4)	−0.011 (2)	0.010 (3)
C16	0.078 (4)	0.157 (6)	0.040 (3)	−0.067 (4)	0.001 (2)	0.006 (3)

Geometric parameters (Å, º) top

Pb1—O2	2.458 (3)	C8—H8A	0.9300
Pb1—O5	2.703 (3)	O6—C22	1.358 (6)
Pb1—O4	2.734 (3)	O6—H6B	0.8200
Pb1—O5ⁱ	2.768 (3)	C21—C26	1.388 (6)
Pb1—O1	2.785 (3)	C21—C22	1.399 (6)
Pb1—O1ⁱⁱ	2.887 (3)	C21—C20	1.502 (5)
Pb1—N1	2.534 (3)	C4—C3	1.398 (7)
Pb1—N2	2.662 (3)	C4—C5	1.426 (7)
Cl1—C18	1.742 (4)	C1—C2	1.397 (6)
Cl2—C25	1.737 (5)	C1—H1A	0.9300
O5—C20	1.259 (5)	C22—C23	1.382 (6)
O5—Pb1ⁱ	2.768 (3)	C19—C18	1.364 (6)
O1—C13	1.235 (5)	C19—H19A	0.9300
O1—Pb1ⁱⁱ	2.887 (3)	C9—C10	1.393 (7)
O2—C13	1.270 (5)	C9—H9A	0.9300
O4—C20	1.261 (5)	C2—C3	1.348 (7)
N1—C1	1.331 (5)	C2—H2A	0.9300
N1—C12	1.350 (5)	C10—H10A	0.9300
N2—C10	1.321 (5)	C26—C25	1.366 (6)
N2—C11	1.353 (5)	C26—H26A	0.9300
C12—C4	1.416 (5)	C3—H3A	0.9300
C12—C11	1.439 (5)	C5—C6	1.336 (8)
O3—C15	1.357 (5)	C5—H5A	0.9300
O3—H3B	0.8200	C6—H6A	0.9300
C11—C7	1.415 (5)	C25—C24	1.402 (8)
C13—C14	1.495 (5)	C24—C23	1.354 (8)
C14—C19	1.390 (5)	C24—H24A	0.9300
C14—C15	1.395 (6)	C23—H23A	0.9300
C15—C16	1.386 (7)	C18—C17	1.385 (7)
C7—C8	1.394 (7)	C17—C16	1.358 (7)
C7—C6	1.417 (7)	C17—H17A	0.9300
C8—C9	1.358 (7)	C16—H16A	0.9300

O2—Pb1—N1	74.00 (10)	O2—C13—C14	116.7 (4)
O2—Pb1—N2	107.51 (10)	O1—C13—Pb1	68.5 (2)
N1—Pb1—N2	63.52 (10)	O2—C13—Pb1	53.5 (2)
O2—Pb1—O5	70.89 (9)	C14—C13—Pb1	170.2 (3)
N1—Pb1—O5	81.85 (9)	C19—C14—C15	118.5 (4)
N2—Pb1—O5	143.50 (9)	C19—C14—C13	120.0 (3)
O2—Pb1—O4	76.94 (10)	C15—C14—C13	121.5 (3)
N1—Pb1—O4	128.10 (10)	O3—C15—C16	117.5 (4)
N2—Pb1—O4	168.25 (9)	O3—C15—C14	122.5 (4)
O5—Pb1—O4	48.05 (9)	C16—C15—C14	120.0 (4)
O2—Pb1—O5ⁱ	135.16 (9)	C8—C7—C11	117.1 (4)
N1—Pb1—O5ⁱ	73.83 (9)	C8—C7—C6	123.7 (4)
N2—Pb1—O5ⁱ	84.71 (9)	C11—C7—C6	119.2 (4)
O5—Pb1—O5ⁱ	74.36 (9)	C9—C8—C7	120.6 (4)
O4—Pb1—O5ⁱ	99.85 (9)	C9—C8—H8A	119.7
O2—Pb1—O1	48.91 (9)	C7—C8—H8A	119.7
N1—Pb1—O1	97.78 (9)	C22—O6—H6B	109.5
N2—Pb1—O1	81.42 (10)	C26—C21—C22	119.5 (4)
O5—Pb1—O1	116.23 (9)	C26—C21—C20	120.4 (4)
O4—Pb1—O1	94.20 (10)	C22—C21—C20	120.1 (4)
O5ⁱ—Pb1—O1	165.95 (9)	C3—C4—C12	117.3 (4)
O2—Pb1—O1ⁱⁱ	111.66 (9)	C3—C4—C5	123.5 (4)
N1—Pb1—O1ⁱⁱ	145.69 (10)	C12—C4—C5	119.2 (4)
N2—Pb1—O1ⁱⁱ	83.09 (9)	N1—C1—C2	122.6 (4)
O5—Pb1—O1ⁱⁱ	132.42 (9)	N1—C1—H1A	118.7
O4—Pb1—O1ⁱⁱ	85.17 (9)	C2—C1—H1A	118.7
O5ⁱ—Pb1—O1ⁱⁱ	112.58 (8)	O6—C22—C23	118.4 (4)
O1—Pb1—O1ⁱⁱ	68.01 (9)	O6—C22—C21	121.9 (4)
O2—Pb1—C13	24.55 (10)	C23—C22—C21	119.7 (4)
N1—Pb1—C13	85.87 (10)	C18—C19—C14	120.6 (4)
N2—Pb1—C13	94.97 (10)	C18—C19—H19A	119.7
O5—Pb1—C13	93.59 (10)	C14—C19—H19A	119.7
O4—Pb1—C13	84.95 (10)	O5—C20—O4	122.8 (4)
O5ⁱ—Pb1—C13	157.51 (10)	O5—C20—C21	119.4 (4)
O1—Pb1—C13	24.36 (9)	O4—C20—C21	117.8 (4)
O1ⁱⁱ—Pb1—C13	89.63 (10)	O5—C20—Pb1	62.0 (2)
O2—Pb1—C20	68.44 (10)	O4—C20—Pb1	63.4 (2)
N1—Pb1—C20	103.98 (11)	C21—C20—Pb1	163.5 (2)
N2—Pb1—C20	167.39 (11)	C8—C9—C10	118.2 (5)
O5—Pb1—C20	24.29 (10)	C8—C9—H9A	120.9
O4—Pb1—C20	24.36 (10)	C10—C9—H9A	120.9
O5ⁱ—Pb1—C20	90.21 (9)	C3—C2—C1	119.2 (4)
O1—Pb1—C20	102.90 (9)	C3—C2—H2A	120.4
O1ⁱⁱ—Pb1—C20	109.53 (11)	C1—C2—H2A	120.4
C13—Pb1—C20	85.33 (10)	N2—C10—C9	124.0 (5)
O2—Pb1—Pb1ⁱ	104.32 (7)	N2—C10—H10A	118.0
N1—Pb1—Pb1ⁱ	74.65 (7)	C9—C10—H10A	118.0
N2—Pb1—Pb1ⁱ	116.10 (7)	C25—C26—C21	119.7 (4)
O5—Pb1—Pb1ⁱ	37.70 (6)	C25—C26—H26A	120.1
O4—Pb1—Pb1ⁱ	72.18 (7)	C21—C26—H26A	120.1
O5ⁱ—Pb1—Pb1ⁱ	36.66 (6)	C2—C3—C4	120.3 (4)
O1—Pb1—Pb1ⁱ	152.88 (6)	C2—C3—H3A	119.8
O1ⁱⁱ—Pb1—Pb1ⁱ	131.46 (6)	C4—C3—H3A	119.8
C13—Pb1—Pb1ⁱ	128.72 (8)	C6—C5—C4	121.2 (4)
C20—Pb1—Pb1ⁱ	55.75 (7)	C6—C5—H5A	119.4
C20—O5—Pb1	93.7 (2)	C4—C5—H5A	119.4
C20—O5—Pb1ⁱ	126.0 (2)	C5—C6—C7	121.9 (4)
Pb1—O5—Pb1ⁱ	105.64 (9)	C5—C6—H6A	119.0
C13—O1—Pb1	87.2 (2)	C7—C6—H6A	119.0
C13—O1—Pb1ⁱⁱ	145.9 (3)	C26—C25—C24	120.7 (4)
Pb1—O1—Pb1ⁱⁱ	111.99 (9)	C26—C25—Cl2	119.8 (4)
C13—O2—Pb1	101.9 (3)	C24—C25—Cl2	119.5 (4)
C20—O4—Pb1	92.2 (2)	C23—C24—C25	119.5 (4)
C1—N1—C12	118.6 (3)	C23—C24—H24A	120.3
C1—N1—Pb1	119.9 (3)	C25—C24—H24A	120.3
C12—N1—Pb1	121.1 (2)	C24—C23—C22	120.9 (5)
C10—N2—C11	117.9 (4)	C24—C23—H23A	119.6
C10—N2—Pb1	124.7 (3)	C22—C23—H23A	119.6
C11—N2—Pb1	116.5 (2)	C19—C18—C17	120.4 (4)
N1—C12—C4	121.9 (4)	C19—C18—Cl1	120.3 (3)
N1—C12—C11	118.9 (3)	C17—C18—Cl1	119.3 (4)
C4—C12—C11	119.2 (4)	C16—C17—C18	119.9 (5)
C15—O3—H3B	109.5	C16—C17—H17A	120.1
N2—C11—C7	122.2 (4)	C18—C17—H17A	120.1
N2—C11—C12	118.5 (3)	C17—C16—C15	120.5 (5)
C7—C11—C12	119.3 (4)	C17—C16—H16A	119.8
O1—C13—O2	122.0 (4)	C15—C16—H16A	119.8
O1—C13—C14	121.3 (3)

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

Experimental details

Crystal data
Chemical formula	[Pb(C₇H₄ClO₃)₂(C₁₂H₈N₂)]
M_r	730.51
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.9100 (1), 11.2959 (1), 13.5816 (1)
α, β, γ (°)	75.508 (1), 86.302 (1), 68.342 (1)
V (Å³)	1229.43 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	7.13
Crystal size (mm)	0.28 × 0.25 × 0.24

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.156, 0.181
No. of measured, independent and observed [I > 2σ(I)] reflections	21579, 5987, 5339
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.664

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.064, 1.05
No. of reflections	5987
No. of parameters	334
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.18, −0.59

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

The authors are grateful for financial support from the Foundation of Zhejiang Educational Committee (No. Y200908533), the Open Fund for Zhejiang Provincial Key of Biological and Chemical Utilization of Forest Resources (No. 200907) and the Fund of Zhejiang Forestry University (No. 235100998).

References

Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wen, D., Xie, J. & Jiang, X. (2008). Acta Cryst. E64, m851–m852. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wen, D. & Ying, S. (2007). Acta Cryst. E63, m2407–m2408. Web of Science CSD CrossRef IUCr Journals Google Scholar

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