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

Cheng, Y.; Yan, F.; Shi, W.; Zhang, L.

doi:10.1107/S1600536812012974

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 4| April 2012| Pages m528-m529

doi:10.1107/S1600536812012974

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

Yuanzheng Cheng,^a ^* Fang Yan,^a Weiwei Shi ^a and Liping Zhang ^a

^aDepartment of Chemistry, Weifang Medical University, Weifang 261053, People's Republic of China
^*Correspondence e-mail: chyzh111@163.com

(Received 5 March 2012; accepted 24 March 2012; online 31 March 2012)

The title compound, [Pb₂(C₇H₅O₂)₂(NO₃)₂(C₁₂H₈N₂)₂(H₂O)₂], crystallizes as a dinuclear centrosymmetric dimer containing two Pb^II atoms bridged by two benzoate ligands. Each Pb^II atom is seven-coordinated by a water molecule, a nitrate anion, a 1,10-phenanthroline (phen) ligand and two benzoate anions. The crystal packing is stabilized by O—H⋯O hydrogen bonds and by π–π stacking between neighboring phen ligands, with a centroid–centroid distance of 3.557 (3) Å.

Related literature

For related Pb(II) complexes with benzoate and 1,10-phenanthroline ligands, see: Dai et al. (2010 ); Li et al. (2011 ); Gao & Xuan (2009 ); Zhu (2006 ).

Experimental

Crystal data

[Pb₂(C₇H₅O₂)₂(NO₃)₂(C₁₂H₈N₂)₂(H₂O)₂]
M_r = 1177.08
Monoclinic, P 2₁ /c
a = 11.7112 (13) Å
b = 13.5403 (15) Å
c = 14.1328 (11) Å
β = 124.483 (6)°
V = 1847.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 9.18 mm⁻¹
T = 296 K
0.22 × 0.18 × 0.16 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.150, T_max = 0.230
9109 measured reflections
3209 independent reflections
2788 reflections with I > 2σ(I)
R_int = 0.038

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.051
S = 1.04
3209 reflections
262 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 1.03 e Å⁻³
Δρ_min = −0.83 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—O1	2.406 (3)
Pb1—O2	2.552 (3)
Pb1—N1	2.560 (3)
Pb1—N2	2.565 (3)
Pb1—O3	2.635 (3)
Pb1—O6	2.989 (3)
Pb1—O2ⁱ	2.913 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O4ⁱⁱ	0.85	2.29	3.116 (5)	164
O6—H6B⋯O3ⁱ	0.85	2.20	2.971 (7)	150
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); 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, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812012974/lr2055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812012974/lr2055Isup2.hkl

checkCIF report

Comment top

Pb(II) complexes with benzoate and 1,10-phenanthroline ligands have been reported in the literature (Dai et al. 2010; Li et al. 2011; Gao & Xuan. 2009; Zhu 2006). Among the four complexes there is a coordination polymer (Zhu 2006), which contains nitrate ligand. In this paper, we report a new binuclear compound, which contains nitrate ligand too.

The crystal structure of the title complex consists of dimeric units [Pb₂(NO₃)₂(C₇H₅O₂)₂(C₁₂H₈N₂)₂(H₂O)₂] (Figure 1),in which each Pb atom has a seven-coordinate geometry defined by one O atom donor from one water molecule,one O atom from a nitrate anion,two N atoms from 1,10-phenanthroline and three O atoms from two benzoate ligands. The Pb—N bond lengths and Pb—O bond lengths range between 2.560 (3) - 2.565 (3) Å and 2.406 (3) - 2.989 (3) Å (Table 1),The weak Pb—O bridging interactions form a four-membered Pb₂O₂ quadrilateral with Pb—Pb separation of 4.356 Å.

In the crystal, O—H···O hydrogen bonds link the water moleculars with nitrate ligands (Table 2 and Figure.2).Aromatic π-π stacking occurs between neighboring phen ligands (Figure.3).The centroid-centroid distance between Cg1(N1/C1–C5) and Cg2(N2/C8–C12) [symmetry code:-x,1 - y,1 - z] is 3.557 (3) Å.

Related literature top

For related Pb(II) complexes with benzoate and 1,10-phenanthroline ligands, see: Dai et al. (2010); Li et al. (2011); Gao & Xuan (2009); Zhu (2006).

Experimental top

A mixture of Pb(NO₃)₂(0.165 g,0.5 mmol), phenylsuccinic acid (0.097 g, 0.5 mmol), 1,10-phenanthroline(0.099 g, 0.5 mmol) and distilled water(15 ml) was sealed in a 25 ml Teflon-lined stainless autoclave. The mixture was heated at 423 K for 24 h. Then the autoclave was cooled to room temperature, after filtration, the resulting light red filtrate was allowed to stand at room temperature, and evaporation for 2 days afforded block light yellow single crystals. Phenylsuccinic acid was oxidized to benzoic acid under high temperature and pressure.

Structure description top

For related Pb(II) complexes with benzoate and 1,10-phenanthroline ligands, see: Dai et al. (2010); Li et al. (2011); Gao & Xuan (2009); Zhu (2006).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level (symmetry code for atoms labelled A:-x+1,-y + 1, - z+1).
	Fig. 2. Part of the crystal structure of (I),showing O—H···O hydrogen bonds as green dashed lines.
	Fig. 3. The π -π stacking of the 1,10- phenanthroline units in the title compound.

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

Crystal data top

[Pb₂(C₇H₅O₂)₂(NO₃)₂(C₁₂H₈N₂)₂(H₂O)₂]	F(000) = 1120
M_r = 1177.08	D_x = 2.116 Mg m⁻³ D_m = 2.116 (1) Mg m⁻³ D_m measured by not measured
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6315 reflections
a = 11.7112 (13) Å	θ = 2.4–27.7°
b = 13.5403 (15) Å	µ = 9.18 mm⁻¹
c = 14.1328 (11) Å	T = 296 K
β = 124.483 (6)°	Block, light-yellow
V = 1847.3 (3) Å³	0.22 × 0.18 × 0.16 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	3209 independent reflections
Radiation source: fine-focus sealed tube	2788 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
phi and ω scans	θ_max = 25.0°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.150, T_max = 0.230	k = −15→16
9109 measured reflections	l = −16→16

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.051	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0209P)² + 0.9758P] where P = (F_o² + 2F_c²)/3
3209 reflections	(Δ/σ)_max = 0.003
262 parameters	Δρ_max = 1.03 e Å⁻³
6 restraints	Δρ_min = −0.83 e Å⁻³

Crystal data top

[Pb₂(C₇H₅O₂)₂(NO₃)₂(C₁₂H₈N₂)₂(H₂O)₂]	V = 1847.3 (3) Å³
M_r = 1177.08	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7112 (13) Å	µ = 9.18 mm⁻¹
b = 13.5403 (15) Å	T = 296 K
c = 14.1328 (11) Å	0.22 × 0.18 × 0.16 mm
β = 124.483 (6)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	3209 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2788 reflections with I > 2σ(I)
T_min = 0.150, T_max = 0.230	R_int = 0.038
9109 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	6 restraints
wR(F²) = 0.051	H-atom parameters constrained
S = 1.04	Δρ_max = 1.03 e Å⁻³
3209 reflections	Δρ_min = −0.83 e Å⁻³
262 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	0.322274 (15)	0.530376 (10)	0.507038 (13)	0.03399 (7)
O1	0.2190 (3)	0.5567 (2)	0.3057 (3)	0.0426 (7)
O2	0.3808 (3)	0.4428 (2)	0.3797 (3)	0.0431 (7)
O3	0.3786 (4)	0.7099 (2)	0.4726 (3)	0.0574 (9)
O4	0.4076 (4)	0.7422 (3)	0.6335 (3)	0.0750 (11)
O5	0.5305 (5)	0.8164 (3)	0.5870 (4)	0.1065 (16)
N1	0.1221 (3)	0.4070 (2)	0.4019 (3)	0.0336 (7)
N2	0.0825 (3)	0.6004 (2)	0.4347 (3)	0.0302 (7)
N3	0.4402 (4)	0.7581 (3)	0.5646 (4)	0.0557 (10)
C1	−0.0097 (4)	0.4381 (3)	0.3570 (3)	0.0319 (9)
C2	0.1409 (5)	0.3132 (3)	0.3863 (4)	0.0439 (11)
H2	0.2308	0.2909	0.4181	0.053*
C3	0.0314 (5)	0.2464 (3)	0.3242 (4)	0.0467 (11)
H3	0.0485	0.1816	0.3137	0.056*
C4	−0.0996 (5)	0.2771 (3)	0.2796 (4)	0.0465 (11)
H4A	−0.1732	0.2334	0.2384	0.056*
C5	−0.1242 (4)	0.3755 (3)	0.2956 (4)	0.0389 (10)
C6	−0.2605 (4)	0.4123 (4)	0.2514 (4)	0.0468 (11)
H6	−0.3361	0.3700	0.2113	0.056*
C7	−0.2807 (4)	0.5071 (3)	0.2672 (4)	0.0446 (11)
H7	−0.3700	0.5296	0.2372	0.054*
C8	−0.1654 (4)	0.5744 (3)	0.3301 (3)	0.0345 (9)
C9	−0.1820 (4)	0.6735 (3)	0.3479 (4)	0.0400 (10)
H9	−0.2698	0.6988	0.3185	0.048*
C10	−0.0679 (5)	0.7327 (3)	0.4088 (4)	0.0434 (10)
H10	−0.0771	0.7985	0.4221	0.052*
C11	0.0622 (4)	0.6932 (3)	0.4507 (4)	0.0385 (10)
H11	0.1389	0.7343	0.4923	0.046*
C12	−0.0301 (4)	0.5400 (3)	0.3746 (3)	0.0295 (8)
C13	0.2744 (5)	0.4860 (3)	0.1831 (4)	0.0407 (10)
C14	0.3537 (5)	0.4185 (4)	0.1693 (4)	0.0511 (11)
H14	0.4155	0.3773	0.2297	0.061*
C15	0.3405 (6)	0.4129 (4)	0.0664 (5)	0.0624 (13)
H15	0.3952	0.3690	0.0579	0.075*
C16	0.2473 (9)	0.4715 (4)	−0.0234 (6)	0.080 (2)
H16	0.2387	0.4668	−0.0928	0.096*
C17	0.1666 (8)	0.5369 (4)	−0.0129 (5)	0.087 (2)
H17	0.1037	0.5770	−0.0742	0.105*
C18	0.1803 (7)	0.5426 (4)	0.0915 (5)	0.0721 (17)
H18	0.1241	0.5859	0.0990	0.087*
C19	0.2933 (4)	0.4950 (3)	0.2965 (4)	0.0333 (9)
O6	0.4669 (4)	0.3437 (3)	0.6293 (3)	0.0666 (10)
H6A	0.5130	0.3253	0.6990	0.100*
H6B	0.4841	0.3147	0.5853	0.100*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.03010 (10)	0.04089 (10)	0.03137 (11)	0.00026 (7)	0.01764 (8)	0.00064 (7)
O1	0.0506 (19)	0.0452 (16)	0.0353 (18)	0.0131 (14)	0.0263 (17)	0.0059 (13)
O2	0.0395 (17)	0.0530 (17)	0.0372 (18)	0.0071 (14)	0.0219 (16)	0.0072 (14)
O3	0.058 (2)	0.0539 (19)	0.041 (2)	−0.0079 (17)	0.0163 (18)	−0.0010 (17)
O4	0.073 (3)	0.092 (3)	0.059 (3)	0.008 (2)	0.037 (2)	0.001 (2)
O5	0.103 (3)	0.098 (3)	0.090 (4)	−0.064 (3)	0.038 (3)	−0.019 (3)
N1	0.0371 (18)	0.0358 (17)	0.0332 (19)	0.0023 (15)	0.0231 (17)	0.0000 (15)
N2	0.0287 (17)	0.0347 (17)	0.0257 (17)	0.0013 (14)	0.0144 (15)	0.0003 (14)
N3	0.056 (3)	0.051 (2)	0.047 (3)	−0.006 (2)	0.022 (2)	0.004 (2)
C1	0.037 (2)	0.036 (2)	0.026 (2)	−0.0030 (17)	0.020 (2)	0.0001 (16)
C2	0.051 (3)	0.037 (2)	0.049 (3)	0.003 (2)	0.032 (3)	−0.003 (2)
C3	0.061 (3)	0.033 (2)	0.042 (3)	−0.002 (2)	0.027 (3)	−0.0102 (19)
C4	0.056 (3)	0.042 (2)	0.038 (3)	−0.012 (2)	0.025 (3)	−0.008 (2)
C5	0.041 (2)	0.043 (2)	0.030 (2)	−0.0064 (19)	0.019 (2)	−0.0011 (18)
C6	0.035 (2)	0.059 (3)	0.038 (3)	−0.013 (2)	0.015 (2)	0.000 (2)
C7	0.029 (2)	0.058 (3)	0.046 (3)	−0.001 (2)	0.020 (2)	0.006 (2)
C8	0.031 (2)	0.046 (2)	0.030 (2)	−0.0001 (18)	0.019 (2)	0.0050 (19)
C9	0.036 (2)	0.048 (2)	0.041 (3)	0.011 (2)	0.025 (2)	0.007 (2)
C10	0.052 (3)	0.038 (2)	0.044 (3)	0.007 (2)	0.029 (2)	0.001 (2)
C11	0.043 (2)	0.036 (2)	0.042 (3)	−0.0034 (18)	0.027 (2)	−0.0052 (18)
C12	0.030 (2)	0.0354 (19)	0.026 (2)	−0.0014 (16)	0.0170 (19)	0.0008 (16)
C13	0.045 (3)	0.042 (2)	0.038 (3)	−0.003 (2)	0.026 (2)	−0.0020 (19)
C14	0.046 (3)	0.057 (3)	0.048 (3)	0.000 (2)	0.025 (3)	−0.008 (2)
C15	0.065 (3)	0.075 (3)	0.057 (3)	0.000 (3)	0.041 (3)	−0.014 (3)
C16	0.125 (6)	0.081 (4)	0.051 (4)	−0.016 (4)	0.060 (4)	−0.013 (3)
C17	0.139 (7)	0.075 (4)	0.045 (4)	0.038 (4)	0.051 (5)	0.013 (3)
C18	0.101 (5)	0.069 (3)	0.047 (3)	0.042 (3)	0.043 (4)	0.016 (3)
C19	0.032 (2)	0.0352 (19)	0.033 (2)	−0.0062 (18)	0.018 (2)	−0.0020 (18)
O6	0.059 (2)	0.069 (2)	0.071 (3)	0.0027 (18)	0.036 (2)	0.0086 (19)

Geometric parameters (Å, º) top

Pb1—O1	2.406 (3)	C6—C7	1.347 (6)
Pb1—O2	2.552 (3)	C6—H6	0.9300
Pb1—N1	2.560 (3)	C7—C8	1.443 (6)
Pb1—N2	2.565 (3)	C7—H7	0.9300
Pb1—O3	2.635 (3)	C8—C9	1.398 (6)
Pb1—O6	2.989 (3)	C8—C12	1.413 (5)
Pb1—O2ⁱ	2.913 (3)	C9—C10	1.366 (6)
Pb1—C19	2.837 (4)	C9—H9	0.9300
O1—C19	1.264 (5)	C10—C11	1.391 (6)
O2—C19	1.253 (5)	C10—H10	0.9300
O3—N3	1.255 (5)	C11—H11	0.9300
O4—N3	1.249 (5)	C13—C18	1.364 (7)
O5—N3	1.210 (5)	C13—C14	1.393 (6)
N1—C2	1.328 (5)	C13—C19	1.495 (6)
N1—C1	1.361 (5)	C14—C15	1.375 (7)
N2—C11	1.322 (5)	C14—H14	0.9300
N2—C12	1.364 (5)	C15—C16	1.366 (9)
C1—C5	1.398 (6)	C15—H15	0.9300
C1—C12	1.446 (5)	C16—C17	1.363 (9)
C2—C3	1.400 (6)	C16—H16	0.9300
C2—H2	0.9300	C17—C18	1.393 (7)
C3—C4	1.352 (6)	C17—H17	0.9300
C3—H3	0.9300	C18—H18	0.9300
C4—C5	1.407 (6)	O6—H6A	0.8500
C4—H4A	0.9300	O6—H6B	0.8501
C5—C6	1.435 (6)

O1—Pb1—O2	52.46 (9)	C5—C6—H6	119.5
O1—Pb1—N1	74.22 (10)	C6—C7—C8	120.9 (4)
O2—Pb1—N1	79.07 (9)	C6—C7—H7	119.5
O1—Pb1—N2	76.72 (10)	C8—C7—H7	119.5
O2—Pb1—N2	124.16 (10)	C9—C8—C12	118.1 (4)
N1—Pb1—N2	64.77 (9)	C9—C8—C7	122.7 (4)
O1—Pb1—O3	69.88 (10)	C12—C8—C7	119.2 (4)
O2—Pb1—O3	95.94 (10)	C10—C9—C8	119.4 (4)
N1—Pb1—O3	137.55 (10)	C10—C9—H9	120.3
N2—Pb1—O3	85.27 (10)	C8—C9—H9	120.3
O1—Pb1—C19	26.28 (10)	C9—C10—C11	119.1 (4)
O2—Pb1—C19	26.20 (10)	C9—C10—H10	120.4
N1—Pb1—C19	75.79 (10)	C11—C10—H10	120.4
N2—Pb1—C19	100.98 (11)	N2—C11—C10	123.5 (4)
O3—Pb1—C19	81.72 (11)	N2—C11—H11	118.2
C19—O1—Pb1	96.3 (2)	C10—C11—H11	118.2
C19—O2—Pb1	89.7 (2)	N2—C12—C8	121.7 (3)
N3—O3—Pb1	110.3 (3)	N2—C12—C1	118.9 (3)
C2—N1—C1	118.0 (4)	C8—C12—C1	119.4 (3)
C2—N1—Pb1	122.5 (3)	C18—C13—C14	118.8 (4)
C1—N1—Pb1	119.5 (2)	C18—C13—C19	121.4 (4)
C11—N2—C12	118.1 (3)	C14—C13—C19	119.9 (4)
C11—N2—Pb1	123.1 (3)	C15—C14—C13	120.0 (5)
C12—N2—Pb1	118.8 (2)	C15—C14—H14	120.0
O5—N3—O4	121.1 (5)	C13—C14—H14	120.0
O5—N3—O3	121.1 (5)	C16—C15—C14	120.2 (5)
O4—N3—O3	117.9 (4)	C16—C15—H15	119.9
N1—C1—C5	122.5 (4)	C14—C15—H15	119.9
N1—C1—C12	118.0 (3)	C15—C16—C17	121.0 (5)
C5—C1—C12	119.5 (4)	C15—C16—H16	119.5
N1—C2—C3	122.8 (4)	C17—C16—H16	119.5
N1—C2—H2	118.6	C16—C17—C18	118.7 (6)
C3—C2—H2	118.6	C16—C17—H17	120.6
C4—C3—C2	119.3 (4)	C18—C17—H17	120.6
C4—C3—H3	120.4	C13—C18—C17	121.3 (5)
C2—C3—H3	120.4	C13—C18—H18	119.3
C3—C4—C5	119.8 (4)	C17—C18—H18	119.3
C3—C4—H4A	120.1	O2—C19—O1	121.4 (4)
C5—C4—H4A	120.1	O2—C19—C13	120.4 (4)
C1—C5—C4	117.5 (4)	O1—C19—C13	118.2 (4)
C1—C5—C6	120.0 (4)	O2—C19—Pb1	64.1 (2)
C4—C5—C6	122.5 (4)	O1—C19—Pb1	57.4 (2)
C7—C6—C5	121.0 (4)	C13—C19—Pb1	174.8 (3)
C7—C6—H6	119.5	H6A—O6—H6B	117.0

O2—Pb1—O1—C19	−1.6 (2)	C6—C7—C8—C9	179.7 (4)
N1—Pb1—O1—C19	−89.8 (2)	C6—C7—C8—C12	0.5 (6)
N2—Pb1—O1—C19	−156.9 (3)	C12—C8—C9—C10	−1.1 (6)
O3—Pb1—O1—C19	113.3 (3)	C7—C8—C9—C10	179.6 (4)
O1—Pb1—O2—C19	1.6 (2)	C8—C9—C10—C11	0.7 (6)
N1—Pb1—O2—C19	80.0 (2)	C12—N2—C11—C10	−0.5 (6)
N2—Pb1—O2—C19	31.0 (3)	Pb1—N2—C11—C10	177.9 (3)
O3—Pb1—O2—C19	−57.4 (2)	C9—C10—C11—N2	0.2 (7)
O1—Pb1—O3—N3	174.1 (3)	C11—N2—C12—C8	0.0 (6)
O2—Pb1—O3—N3	−139.6 (3)	Pb1—N2—C12—C8	−178.5 (3)
N1—Pb1—O3—N3	140.1 (3)	C11—N2—C12—C1	−179.6 (3)
N2—Pb1—O3—N3	96.5 (3)	Pb1—N2—C12—C1	1.9 (4)
C19—Pb1—O3—N3	−161.6 (3)	C9—C8—C12—N2	0.8 (6)
O1—Pb1—N1—C2	97.8 (3)	C7—C8—C12—N2	−180.0 (4)
O2—Pb1—N1—C2	44.0 (3)	C9—C8—C12—C1	−179.6 (4)
N2—Pb1—N1—C2	−179.7 (3)	C7—C8—C12—C1	−0.4 (6)
O3—Pb1—N1—C2	130.9 (3)	N1—C1—C12—N2	0.2 (5)
C19—Pb1—N1—C2	70.7 (3)	C5—C1—C12—N2	−180.0 (4)
O1—Pb1—N1—C1	−80.3 (3)	N1—C1—C12—C8	−179.4 (4)
O2—Pb1—N1—C1	−134.1 (3)	C5—C1—C12—C8	0.4 (6)
N2—Pb1—N1—C1	2.2 (3)	C18—C13—C14—C15	2.8 (8)
O3—Pb1—N1—C1	−47.3 (3)	C19—C13—C14—C15	−177.4 (4)
C19—Pb1—N1—C1	−107.5 (3)	C13—C14—C15—C16	−1.7 (8)
O1—Pb1—N2—C11	−101.9 (3)	C14—C15—C16—C17	0.5 (10)
O2—Pb1—N2—C11	−125.5 (3)	C15—C16—C17—C18	−0.4 (11)
N1—Pb1—N2—C11	179.5 (3)	C14—C13—C18—C17	−2.7 (9)
O3—Pb1—N2—C11	−31.5 (3)	C19—C13—C18—C17	177.5 (5)
C19—Pb1—N2—C11	−112.1 (3)	C16—C17—C18—C13	1.5 (11)
O1—Pb1—N2—C12	76.5 (3)	Pb1—O2—C19—O1	−2.8 (4)
O2—Pb1—N2—C12	53.0 (3)	Pb1—O2—C19—C13	177.0 (3)
N1—Pb1—N2—C12	−2.1 (2)	Pb1—O1—C19—O2	3.0 (4)
O3—Pb1—N2—C12	147.0 (3)	Pb1—O1—C19—C13	−176.8 (3)
C19—Pb1—N2—C12	66.4 (3)	C18—C13—C19—O2	−179.6 (5)
Pb1—O3—N3—O5	143.7 (4)	C14—C13—C19—O2	0.6 (6)
Pb1—O3—N3—O4	−34.4 (5)	C18—C13—C19—O1	0.2 (7)
C2—N1—C1—C5	−0.2 (6)	C14—C13—C19—O1	−179.6 (4)
Pb1—N1—C1—C5	178.0 (3)	C18—C13—C19—Pb1	−31 (3)
C2—N1—C1—C12	179.6 (4)	C14—C13—C19—Pb1	149 (3)
Pb1—N1—C1—C12	−2.2 (5)	O1—Pb1—C19—O2	−177.2 (4)
C1—N1—C2—C3	1.3 (6)	N1—Pb1—C19—O2	−94.1 (2)
Pb1—N1—C2—C3	−176.8 (3)	N2—Pb1—C19—O2	−154.3 (2)
N1—C2—C3—C4	−1.4 (7)	O3—Pb1—C19—O2	122.2 (2)
C2—C3—C4—C5	0.3 (7)	O2—Pb1—C19—O1	177.2 (4)
N1—C1—C5—C4	−0.8 (6)	N1—Pb1—C19—O1	83.1 (2)
C12—C1—C5—C4	179.4 (4)	N2—Pb1—C19—O1	22.9 (3)
N1—C1—C5—C6	179.3 (4)	O3—Pb1—C19—O1	−60.6 (2)
C12—C1—C5—C6	−0.5 (6)	O1—Pb1—C19—C13	33 (3)
C3—C4—C5—C1	0.7 (6)	O2—Pb1—C19—C13	−150 (3)
C3—C4—C5—C6	−179.4 (4)	N1—Pb1—C19—C13	116 (3)
C1—C5—C6—C7	0.6 (7)	N2—Pb1—C19—C13	56 (3)
C4—C5—C6—C7	−179.3 (4)	O3—Pb1—C19—C13	−28 (3)
C5—C6—C7—C8	−0.6 (7)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O4ⁱⁱ	0.85	2.29	3.116 (5)	164
O6—H6B···O3ⁱ	0.85	2.20	2.971 (7)	150

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

Experimental details

Crystal data
Chemical formula	[Pb₂(C₇H₅O₂)₂(NO₃)₂(C₁₂H₈N₂)₂(H₂O)₂]
M_r	1177.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.7112 (13), 13.5403 (15), 14.1328 (11)
β (°)	124.483 (6)
V (Å³)	1847.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	9.18
Crystal size (mm)	0.22 × 0.18 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.150, 0.230
No. of measured, independent and observed [I > 2σ(I)] reflections	9109, 3209, 2788
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.051, 1.04
No. of reflections	3209
No. of parameters	262
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.03, −0.83

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Pb1—O1	2.406 (3)	Pb1—O3	2.635 (3)
Pb1—O2	2.552 (3)	Pb1—O6	2.989 (3)
Pb1—N1	2.560 (3)	Pb1—O2ⁱ	2.913 (3)
Pb1—N2	2.565 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O4ⁱⁱ	0.8500	2.2900	3.116 (5)	164.00
O6—H6B···O3ⁱ	0.8500	2.2000	2.971 (7)	150.00

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

Acknowledgements

The authors gratefully acknowledge financial support from Shandong Provincial Education Department (grant No. J09LB57)

References

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