Di-μ-benzoato-κ3O,O′:O;κ3O:O,O′-bis­[(acetato-κO)(1,10-phenanthroline-κ2N,N′)lead(II)] dihydrate

Gao, J.; Xuan, X.

doi:10.1107/S1600536809025896

metal-organic compounds

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Volume 65| Part 8| August 2009| Page m900

doi:10.1107/S1600536809025896

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Di-μ-benzoato-κ³O,O′:O;κ³O:O,O′-bis[(acetato-κO)(1,10-phenanthroline-κ²N,N′)lead(II)] dihydrate

Junli Gao ^a and Xiaopeng Xuan ^a ^*

^aDepartment of Chemistry, Henan Normal University, Xinxiang 453007, People's Republic of China
^*Correspondence e-mail: xuanxiaopeng@126.com

(Received 22 June 2009; accepted 3 July 2009; online 11 July 2009)

The title compound, [Pb₂(CH₃COO)₂(C₇H₅O₂)₂(C₁₂H₈N₂)₂]·2H₂O, consists of dimeric units built up around a crystallographic centre of symmetry and two non-coordinating water molecules. Each Pb^II unit is six-coordinated by a bidentate 1,10-phenanthroline (phen) ligand, a monodentate acetate anion and a bidentate benzoate anion, which also acts as a bridge linking the two Pb^II atoms. The crystal packing is stabilized by O—H⋯O hydrogen bonds and by π–π interactions between the phen rings of neighboring molecules, with a centroid–centroid distance of 3.577 (3) Å.

Related literature

For information on the coordination chemistry of lead, see: Shimoni-Livny et al. (1998 ). For related structures, see: Li & Yang (2004 ); Xuan et al. (2008 ); Xuan & Zhao (2007 ); Zhao et al. (2007 ); Zhu et al. (2004 ).

Experimental

Crystal data

[Pb₂(C₂H₃O₂)₂(C₇H₅O₂)₂(C₁₂H₈N₂)₂]·2H₂O
M_r = 1171.15
Monoclinic, P 2₁ /n
a = 11.809 (4) Å
b = 13.910 (5) Å
c = 12.290 (4) Å
β = 107.392 (4)°
V = 1926.5 (11) Å³
Z = 2
Mo Kα radiation
μ = 8.79 mm⁻¹
T = 294 K
0.11 × 0.07 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.445, T_max = 0.668
16820 measured reflections
4417 independent reflections
3343 reflections with I > 2σ(I)
R_int = 0.044

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.057
S = 1.03
4417 reflections
263 parameters
18 restraints
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.85 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—O3	2.399 (3)
Pb1—O2	2.426 (3)
Pb1—O1	2.565 (3)
Pb1—O1ⁱ	2.828 (3)
Pb1—N2	2.619 (4)
Pb1—N1	2.688 (4)
Symmetry code: (i) -x, -y, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H2W⋯O3ⁱⁱ	0.83	2.15	2.958 (5)	166
O5—H1W⋯O4	0.83	2.11	2.928 (5)	169
Symmetry code: (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809025896/sj2634sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809025896/sj2634Isup2.hkl

checkCIF report

Comment top

Because of the increasing impact of the toxic heavy metal lead on the natural environment, the coordination behavior of lead ion has received more and more attention. Lead(II) is capable of exhibiting a variable coordination number and geometry with or without a stereochemically active lone pair of electrons (Shimoni-Livny et al. 1998). Among such compounds, a number of centrosymmetric dinuclear lead(II) compounds with 1,10-phenanthroline (phen) or its derivatives and oxygen donor ligands have been structurally characterized (Li & Yang, 2004, Xuan et al. 2008, Xuan & Zhao, 2007, Zhao et al. 2007, Zhu et al. 2004,). Recently, we obtained the title lead(II) complex containing two different kinds of anions, by the reaction of lead acetate, sodium benzoate and phen in ethanol/water mixtures.

The crystal structure of the title compound consists of dimeric units [Pb₂(C₂H₃O₂)₂(C₇H₅O₂)₂(C₁₂H₈N₂)₂], related by a crystallographic inversion centre (Fig. 1), and two uncoordinated water molecules. Both the acetate and benzoate anions are coordinated to each Pb(II) atom and a carboxylate oxygen of each benzoate anion forms a bridge between the two inversion related lead atoms. Each lead atom is chelated by the two N atoms of phen with Pb—N distances of 2.619 (4), and 2.688 (4) Å, three carbonyl oxygen atoms of two benzoate anions and one carbonyl oxygen atoms of an acetate anion. The weak Pb—O bridging interactions form a four-membered Pb₂O₂ quadrilateral with a Pb—Pb separation of 4.289 (5) Å.

The crystal structure is stabilized by intermolecular O—H···O hydrogen bonds (Table 1 and Figure 2). The uncoordinated water molecules participate in hydrogen bonding to oxygen atoms of the acetate anions. The crystal packing is further stabilized by π-π stacking interactions between adjacent phen molecules. The centroid-centroid distance between Cg1 (N1/C8—C11/C19) and Cg2 (N2/C14—C18)[symmetry code: 1 - x, -y, 1 - z] is 3.575 (3) Å.

Related literature top

For information on the coordination chemistry of lead, see: Shimoni-Livny et al. (1998). For related structures, see: Li & Yang (2004); Xuan et al. (2008); Xuan & Zhao (2007); Zhao et al. (2007); Zhu et al. (2004).

Experimental top

A solution (10 ml) of ethanol containing 1,10-phenanthroline (0.5 mmol) and sodium benzoate (1 mmol) was added slowly to a aqueous solution (10 ml) containing lead acetate trihydrate (0.5 mmol). The mixture was refluxed for 5 h and the resulting white precipitate was filtered. Block-like single crystals were obtained by slow evaporation of the filtrate at room temperature after five days.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); 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: publCIF (Westrip, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. [Symmetry code for atoms labelled A: -x, -y, 1 - z].
	Fig. 2. Part of the crystal structure of (I), showing the hydrogen-bonding (dashed lines) interactions.
	Fig. 3. π-π interactions between the aromatic rings of the title compound.

Di-µ-benzoato- κ³O,O':O;κ³O:O,O'- bis[(acetato-κO)(1,10-phenanthroline-κ²N,N')lead(II)] dihydrate top

Crystal data top

[Pb₂(C₂H₃O₂)₂(C₇H₅O₂)₂(C₁₂H₈N₂)₂]·2H₂O	F(000) = 1120
M_r = 1171.15	D_x = 2.019 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3638 reflections
a = 11.809 (4) Å	θ = 2.3–23.1°
b = 13.910 (5) Å	µ = 8.79 mm⁻¹
c = 12.290 (4) Å	T = 294 K
β = 107.392 (4)°	Block, colourless
V = 1926.5 (11) Å³	0.11 × 0.07 × 0.05 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	4417 independent reflections
Radiation source: fine-focus sealed tube	3343 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −15→15
T_min = 0.445, T_max = 0.668	k = −18→18
16820 measured reflections	l = −15→15

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0213P)²] where P = (F_o² + 2F_c²)/3
4417 reflections	(Δ/σ)_max = 0.001
263 parameters	Δρ_max = 0.73 e Å⁻³
18 restraints	Δρ_min = −0.85 e Å⁻³

Crystal data top

[Pb₂(C₂H₃O₂)₂(C₇H₅O₂)₂(C₁₂H₈N₂)₂]·2H₂O	V = 1926.5 (11) Å³
M_r = 1171.15	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.809 (4) Å	µ = 8.79 mm⁻¹
b = 13.910 (5) Å	T = 294 K
c = 12.290 (4) Å	0.11 × 0.07 × 0.05 mm
β = 107.392 (4)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4417 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	3343 reflections with I > 2σ(I)
T_min = 0.445, T_max = 0.668	R_int = 0.044
16820 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	18 restraints
wR(F²) = 0.057	H-atom parameters constrained
S = 1.03	Δρ_max = 0.73 e Å⁻³
4417 reflections	Δρ_min = −0.85 e Å⁻³
263 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)

are estimated using the full covariance matrix. The cell e.s.d.'s are taken

into account individually in the estimation of e.s.d.'s in distances, angles

and torsion angles; correlations between e.s.d.'s in cell parameters are only

used when they are defined by crystal symmetry. An approximate (isotropic)

treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Pb1	0.173727 (14)	0.043850 (12)	0.498903 (14)	0.03372 (6)
N1	0.2720 (3)	−0.0825 (3)	0.3883 (3)	0.0359 (9)
N2	0.3507 (3)	0.1041 (3)	0.4296 (3)	0.0311 (8)
O1	−0.0112 (3)	−0.0419 (2)	0.3725 (3)	0.0457 (8)
O2	0.0805 (3)	0.0648 (2)	0.2958 (3)	0.0423 (8)
O3	0.0861 (3)	0.2009 (2)	0.4678 (3)	0.0518 (7)
O4	0.2321 (3)	0.2249 (2)	0.6272 (3)	0.0544 (8)
O5	0.3305 (3)	0.3221 (3)	0.8466 (3)	0.0727 (12)
H1W	0.3119	0.2922	0.7852	0.109*
H2W	0.4037	0.3247	0.8745	0.109*
C1	−0.0917 (4)	−0.0099 (3)	0.1737 (4)	0.0316 (10)
C2	−0.0902 (4)	0.0467 (4)	0.0825 (4)	0.0496 (13)
H2	−0.0340	0.0953	0.0923	0.059*
C3	−0.1716 (5)	0.0322 (4)	−0.0240 (4)	0.0610 (16)
H3	−0.1702	0.0710	−0.0852	0.073*
C4	−0.2551 (5)	−0.0405 (4)	−0.0383 (5)	0.0591 (15)
H4	−0.3101	−0.0508	−0.1094	0.071*
C5	−0.2564 (4)	−0.0974 (4)	0.0529 (4)	0.0517 (14)
H5	−0.3130	−0.1457	0.0433	0.062*
C6	−0.1751 (4)	−0.0836 (3)	0.1580 (4)	0.0408 (12)
H6	−0.1757	−0.1233	0.2187	0.049*
C7	−0.0022 (4)	0.0053 (3)	0.2875 (4)	0.0358 (11)
C8	0.2340 (5)	−0.1718 (4)	0.3670 (4)	0.0478 (13)
H8	0.1693	−0.1909	0.3903	0.057*
C9	0.2844 (5)	−0.2388 (4)	0.3123 (4)	0.0555 (15)
H9	0.2538	−0.3008	0.2992	0.067*
C10	0.3789 (5)	−0.2130 (4)	0.2779 (4)	0.0510 (14)
H10	0.4144	−0.2572	0.2415	0.061*
C11	0.4235 (4)	−0.1176 (4)	0.2979 (4)	0.0408 (12)
C12	0.5245 (5)	−0.0854 (4)	0.2670 (4)	0.0493 (14)
H12	0.5628	−0.1274	0.2307	0.059*
C13	0.5649 (4)	0.0053 (4)	0.2898 (4)	0.0467 (13)
H13	0.6318	0.0242	0.2703	0.056*
C14	0.5072 (4)	0.0736 (3)	0.3438 (4)	0.0342 (11)
C15	0.5469 (4)	0.1678 (4)	0.3670 (4)	0.0426 (12)
H15	0.6125	0.1896	0.3471	0.051*
C16	0.4878 (4)	0.2280 (4)	0.4197 (4)	0.0429 (12)
H16	0.5116	0.2917	0.4345	0.051*
C17	0.3918 (4)	0.1927 (3)	0.4507 (4)	0.0367 (11)
H17	0.3542	0.2338	0.4885	0.044*
C18	0.4080 (4)	0.0436 (3)	0.3760 (4)	0.0306 (10)
C19	0.3653 (4)	−0.0553 (3)	0.3537 (4)	0.0329 (10)
C20	0.1402 (5)	0.2519 (4)	0.5538 (4)	0.0513 (7)
C21	0.0877 (5)	0.3482 (4)	0.5642 (4)	0.0572 (11)
H21A	0.0272	0.3411	0.6012	0.086*
H21B	0.0535	0.3751	0.4896	0.086*
H21C	0.1487	0.3902	0.6084	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.02875 (9)	0.04061 (11)	0.03074 (10)	−0.00348 (9)	0.00726 (7)	−0.00015 (9)
N1	0.036 (2)	0.031 (2)	0.038 (2)	−0.0030 (17)	0.0064 (18)	−0.0009 (17)
N2	0.030 (2)	0.033 (2)	0.030 (2)	−0.0017 (17)	0.0089 (16)	0.0002 (16)
O1	0.0395 (19)	0.065 (2)	0.0321 (18)	−0.0089 (17)	0.0104 (15)	0.0032 (17)
O2	0.043 (2)	0.039 (2)	0.0392 (19)	−0.0107 (15)	0.0051 (16)	0.0036 (15)
O3	0.0595 (17)	0.0502 (16)	0.0416 (15)	0.0045 (13)	0.0091 (13)	−0.0036 (13)
O4	0.0521 (18)	0.0559 (18)	0.0500 (17)	0.0017 (15)	0.0074 (14)	0.0008 (15)
O5	0.052 (2)	0.087 (3)	0.085 (3)	−0.006 (2)	0.029 (2)	−0.008 (2)
C1	0.028 (2)	0.035 (2)	0.030 (2)	0.004 (2)	0.007 (2)	−0.001 (2)
C2	0.046 (3)	0.056 (3)	0.040 (3)	−0.010 (3)	0.004 (2)	0.007 (3)
C3	0.067 (4)	0.073 (4)	0.037 (3)	−0.004 (3)	0.007 (3)	0.010 (3)
C4	0.058 (4)	0.062 (4)	0.041 (3)	0.003 (3)	−0.010 (3)	−0.006 (3)
C5	0.041 (3)	0.047 (3)	0.055 (3)	−0.005 (2)	−0.004 (3)	−0.007 (3)
C6	0.039 (3)	0.038 (3)	0.043 (3)	0.000 (2)	0.009 (2)	0.003 (2)
C7	0.036 (3)	0.038 (3)	0.034 (3)	0.004 (2)	0.011 (2)	−0.004 (2)
C8	0.050 (3)	0.043 (3)	0.045 (3)	−0.011 (3)	0.007 (3)	0.000 (2)
C9	0.075 (4)	0.033 (3)	0.048 (3)	−0.002 (3)	0.002 (3)	−0.007 (3)
C10	0.071 (4)	0.045 (3)	0.031 (3)	0.013 (3)	0.007 (3)	−0.008 (2)
C11	0.047 (3)	0.046 (3)	0.025 (2)	0.015 (2)	0.005 (2)	0.002 (2)
C12	0.051 (3)	0.059 (4)	0.040 (3)	0.025 (3)	0.017 (3)	0.005 (3)
C13	0.039 (3)	0.068 (4)	0.038 (3)	0.018 (3)	0.019 (2)	0.017 (3)
C14	0.024 (2)	0.050 (3)	0.027 (2)	0.006 (2)	0.0062 (19)	0.013 (2)
C15	0.029 (3)	0.057 (3)	0.039 (3)	−0.007 (2)	0.007 (2)	0.013 (2)
C16	0.038 (3)	0.043 (3)	0.047 (3)	−0.012 (2)	0.011 (2)	0.000 (2)
C17	0.034 (3)	0.039 (3)	0.036 (3)	−0.004 (2)	0.009 (2)	−0.002 (2)
C18	0.027 (2)	0.034 (2)	0.027 (2)	0.003 (2)	0.0023 (18)	0.002 (2)
C19	0.035 (2)	0.035 (3)	0.023 (2)	0.007 (2)	−0.0002 (19)	0.005 (2)
C20	0.0571 (16)	0.0509 (16)	0.0431 (15)	0.0041 (13)	0.0105 (13)	−0.0033 (12)
C21	0.062 (2)	0.055 (2)	0.049 (2)	0.0080 (19)	0.0087 (18)	−0.0094 (18)

Geometric parameters (Å, º) top

Pb1—O3	2.399 (3)	C5—H5	0.9300
Pb1—O2	2.426 (3)	C6—H6	0.9300
Pb1—O1	2.565 (3)	C8—C9	1.384 (7)
Pb1—O1ⁱ	2.828 (3)	C8—H8	0.9300
Pb1—N2	2.619 (4)	C9—C10	1.355 (7)
Pb1—N1	2.688 (4)	C9—H9	0.9300
Pb1—C7	2.851 (5)	C10—C11	1.421 (7)
N1—C8	1.320 (6)	C10—H10	0.9300
N1—C19	1.349 (6)	C11—C19	1.405 (6)
N2—C17	1.321 (5)	C11—C12	1.428 (7)
N2—C18	1.366 (5)	C12—C13	1.348 (7)
O1—C7	1.264 (5)	C12—H12	0.9300
O2—C7	1.261 (5)	C13—C14	1.442 (7)
O3—C20	1.273 (6)	C13—H13	0.9300
O4—C20	1.244 (6)	C14—C15	1.393 (6)
O5—H1W	0.8317	C14—C18	1.407 (6)
O5—H2W	0.8295	C15—C16	1.370 (6)
C1—C2	1.375 (6)	C15—H15	0.9300
C1—C6	1.394 (6)	C16—C17	1.390 (6)
C1—C7	1.495 (6)	C16—H16	0.9300
C2—C3	1.387 (7)	C17—H17	0.9300
C2—H2	0.9300	C18—C19	1.463 (6)
C3—C4	1.387 (7)	C20—C21	1.498 (7)
C3—H3	0.9300	C21—H21A	0.9600
C4—C5	1.377 (7)	C21—H21B	0.9600
C4—H4	0.9300	C21—H21C	0.9600
C5—C6	1.373 (6)

O3—Pb1—O2	71.68 (11)	O1—C7—Pb1	64.1 (2)
O3—Pb1—O1	94.51 (11)	C1—C7—Pb1	176.6 (4)
O2—Pb1—O1	52.41 (10)	N1—C8—C9	124.1 (5)
O3—Pb1—N2	90.27 (12)	N1—C8—H8	118.0
O2—Pb1—N2	77.74 (11)	C9—C8—H8	118.0
O1—Pb1—N2	124.72 (10)	C10—C9—C8	119.2 (5)
O3—Pb1—N1	138.24 (11)	C10—C9—H9	120.4
O2—Pb1—N1	71.93 (11)	C8—C9—H9	120.4
O1—Pb1—N1	78.91 (11)	C9—C10—C11	119.3 (5)
N2—Pb1—N1	62.48 (11)	C9—C10—H10	120.3
O3—Pb1—C7	82.19 (12)	C11—C10—H10	120.3
O2—Pb1—C7	26.08 (12)	C19—C11—C10	116.8 (5)
O1—Pb1—C7	26.33 (11)	C19—C11—C12	120.4 (5)
N2—Pb1—C7	101.47 (13)	C10—C11—C12	122.8 (5)
N1—Pb1—C7	73.94 (12)	C13—C12—C11	120.7 (5)
C8—N1—C19	117.6 (4)	C13—C12—H12	119.7
C8—N1—Pb1	122.9 (3)	C11—C12—H12	119.7
C19—N1—Pb1	119.5 (3)	C12—C13—C14	121.8 (5)
C17—N2—C18	117.6 (4)	C12—C13—H13	119.1
C17—N2—Pb1	121.1 (3)	C14—C13—H13	119.1
C18—N2—Pb1	121.2 (3)	C15—C14—C18	118.6 (4)
C7—O1—Pb1	89.6 (3)	C15—C14—C13	122.6 (5)
C7—O2—Pb1	96.1 (3)	C18—C14—C13	118.8 (5)
C20—O3—Pb1	106.8 (3)	C16—C15—C14	119.0 (4)
H1W—O5—H2W	110.9	C16—C15—H15	120.5
C2—C1—C6	119.3 (4)	C14—C15—H15	120.5
C2—C1—C7	120.2 (4)	C15—C16—C17	119.1 (5)
C6—C1—C7	120.5 (4)	C15—C16—H16	120.5
C1—C2—C3	120.8 (5)	C17—C16—H16	120.5
C1—C2—H2	119.6	N2—C17—C16	124.0 (4)
C3—C2—H2	119.6	N2—C17—H17	118.0
C4—C3—C2	119.4 (5)	C16—C17—H17	118.0
C4—C3—H3	120.3	N2—C18—C14	121.8 (4)
C2—C3—H3	120.3	N2—C18—C19	118.5 (4)
C5—C4—C3	119.7 (5)	C14—C18—C19	119.7 (4)
C5—C4—H4	120.1	N1—C19—C11	123.1 (4)
C3—C4—H4	120.1	N1—C19—C18	118.2 (4)
C6—C5—C4	120.8 (5)	C11—C19—C18	118.7 (4)
C6—C5—H5	119.6	O4—C20—O3	123.1 (5)
C4—C5—H5	119.6	O4—C20—C21	120.1 (5)
C5—C6—C1	119.9 (5)	O3—C20—C21	116.8 (5)
C5—C6—H6	120.0	C20—C21—H21A	109.5
C1—C6—H6	120.0	C20—C21—H21B	109.5
O2—C7—O1	121.9 (4)	H21A—C21—H21B	109.5
O2—C7—C1	118.9 (4)	C20—C21—H21C	109.5
O1—C7—C1	119.2 (4)	H21A—C21—H21C	109.5
O2—C7—Pb1	57.8 (2)	H21B—C21—H21C	109.5

O3—Pb1—N1—C8	−124.4 (3)	C6—C1—C7—O1	−8.0 (7)
O2—Pb1—N1—C8	−93.9 (4)	O3—Pb1—C7—O2	63.8 (3)
O1—Pb1—N1—C8	−40.1 (3)	O1—Pb1—C7—O2	−179.1 (5)
N2—Pb1—N1—C8	−179.2 (4)	N2—Pb1—C7—O2	−24.9 (3)
C7—Pb1—N1—C8	−66.7 (4)	N1—Pb1—C7—O2	−81.6 (3)
O3—Pb1—N1—C19	56.5 (4)	O3—Pb1—C7—O1	−117.1 (3)
O2—Pb1—N1—C19	87.0 (3)	O2—Pb1—C7—O1	179.1 (5)
O1—Pb1—N1—C19	140.8 (3)	N2—Pb1—C7—O1	154.2 (3)
N2—Pb1—N1—C19	1.7 (3)	N1—Pb1—C7—O1	97.5 (3)
C7—Pb1—N1—C19	114.2 (3)	C19—N1—C8—C9	0.4 (7)
O3—Pb1—N2—C17	34.5 (3)	Pb1—N1—C8—C9	−178.7 (4)
O2—Pb1—N2—C17	105.7 (3)	N1—C8—C9—C10	0.2 (8)
O1—Pb1—N2—C17	130.2 (3)	C8—C9—C10—C11	−0.5 (7)
N1—Pb1—N2—C17	−178.5 (3)	C9—C10—C11—C19	0.2 (7)
C7—Pb1—N2—C17	116.6 (3)	C9—C10—C11—C12	178.4 (5)
O3—Pb1—N2—C18	−149.1 (3)	C19—C11—C12—C13	−0.6 (7)
O2—Pb1—N2—C18	−77.9 (3)	C10—C11—C12—C13	−178.6 (4)
O1—Pb1—N2—C18	−53.4 (3)	C11—C12—C13—C14	−1.3 (7)
N1—Pb1—N2—C18	−2.1 (3)	C12—C13—C14—C15	−179.3 (4)
C7—Pb1—N2—C18	−67.0 (3)	C12—C13—C14—C18	1.7 (7)
O3—Pb1—O1—C7	62.2 (3)	C18—C14—C15—C16	−0.3 (6)
O2—Pb1—O1—C7	−0.5 (3)	C13—C14—C15—C16	−179.3 (4)
N2—Pb1—O1—C7	−31.3 (3)	C14—C15—C16—C17	1.5 (7)
N1—Pb1—O1—C7	−76.1 (3)	C18—N2—C17—C16	1.3 (6)
O3—Pb1—O2—C7	−110.5 (3)	Pb1—N2—C17—C16	177.8 (3)
O1—Pb1—O2—C7	0.5 (3)	C15—C16—C17—N2	−2.0 (7)
N2—Pb1—O2—C7	155.0 (3)	C17—N2—C18—C14	−0.1 (6)
N1—Pb1—O2—C7	90.3 (3)	Pb1—N2—C18—C14	−176.5 (3)
O2—Pb1—O3—C20	−157.3 (4)	C17—N2—C18—C19	178.9 (4)
O1—Pb1—O3—C20	154.8 (3)	Pb1—N2—C18—C19	2.5 (5)
N2—Pb1—O3—C20	−80.3 (3)	C15—C14—C18—N2	−0.4 (6)
N1—Pb1—O3—C20	−126.8 (3)	C13—C14—C18—N2	178.6 (4)
C7—Pb1—O3—C20	178.1 (4)	C15—C14—C18—C19	−179.4 (4)
C6—C1—C2—C3	1.0 (8)	C13—C14—C18—C19	−0.3 (6)
C7—C1—C2—C3	178.9 (5)	C8—N1—C19—C11	−0.7 (6)
C1—C2—C3—C4	−0.2 (9)	Pb1—N1—C19—C11	178.4 (3)
C2—C3—C4—C5	0.0 (9)	C8—N1—C19—C18	179.6 (4)
C3—C4—C5—C6	−0.6 (9)	Pb1—N1—C19—C18	−1.2 (5)
C4—C5—C6—C1	1.4 (8)	C10—C11—C19—N1	0.4 (6)
C2—C1—C6—C5	−1.6 (7)	C12—C11—C19—N1	−177.7 (4)
C7—C1—C6—C5	−179.5 (4)	C10—C11—C19—C18	−180.0 (4)
Pb1—O2—C7—O1	−1.0 (5)	C12—C11—C19—C18	1.9 (6)
Pb1—O2—C7—C1	179.3 (4)	N2—C18—C19—N1	−0.8 (6)
Pb1—O1—C7—O2	0.9 (5)	C14—C18—C19—N1	178.2 (4)
Pb1—O1—C7—C1	−179.4 (4)	N2—C18—C19—C11	179.6 (4)
C2—C1—C7—O2	−6.3 (7)	C14—C18—C19—C11	−1.4 (6)
C6—C1—C7—O2	171.7 (4)	Pb1—O3—C20—O4	10.0 (7)
C2—C1—C7—O1	174.0 (4)	Pb1—O3—C20—C21	−169.7 (4)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H2W···O3ⁱⁱ	0.83	2.15	2.958 (5)	166
O5—H1W···O4	0.83	2.11	2.928 (5)	169

Symmetry code: (ii) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	[Pb₂(C₂H₃O₂)₂(C₇H₅O₂)₂(C₁₂H₈N₂)₂]·2H₂O
M_r	1171.15
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	294
a, b, c (Å)	11.809 (4), 13.910 (5), 12.290 (4)
β (°)	107.392 (4)
V (Å³)	1926.5 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	8.79
Crystal size (mm)	0.11 × 0.07 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.445, 0.668
No. of measured, independent and observed [I > 2σ(I)] reflections	16820, 4417, 3343
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.057, 1.03
No. of reflections	4417
No. of parameters	263
No. of restraints	18
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.85

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Pb1—O3	2.399 (3)	Pb1—O1ⁱ	2.828 (3)
Pb1—O2	2.426 (3)	Pb1—N2	2.619 (4)
Pb1—O1	2.565 (3)	Pb1—N1	2.688 (4)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H2W···O3ⁱⁱ	0.83	2.15	2.958 (5)	165.7
O5—H1W···O4	0.83	2.11	2.928 (5)	169.2

Symmetry code: (ii) x+1/2, −y+1/2, z+1/2.

Acknowledgements

We are grateful to the Youth Natural Science Foundation of Henan Normal University for financial support.

References

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