Bis(μ-3-hydroxy­benzoato-κ3O,O′:O)bis­[aqua­(3-hydroxy­benzoato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)lead(II)] monohydrate

Xuan, X.-P.; Zhao, P.-Z.; Zhang, S.-X.

doi:10.1107/S1600536807065075

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Pages m152-m153

https://doi.org/10.1107/S1600536807065075

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Bis(μ-3-hydroxybenzoato-κ³O,O′:O)bis[aqua(3-hydroxybenzoato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)lead(II)] monohydrate

Xiao-Peng Xuan,^a ^* Pei-Zheng Zhao ^a and Shu-Xia Zhang ^a

^aDepartment of Chemistry, Henan Normal University, Xinxiang 453007, People's Republic of China
^*Correspondence e-mail: xpxuan@henannu.edu.cn

(Received 2 November 2007; accepted 2 December 2007; online 12 December 2007)

In the centrosymmetric binuclear title complex, [Pb₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂(H₂O)₂]·H₂O, each Pb atom is eight-coordinated in a PbO₆N₂ environment by two N atoms from the 1,10-phenanthroline (phen) ligand, five carboxylate O atoms from four 3-hydroxybenzoate anions and one O atom from the coordinated water molecule in a distorted bicapped trigonal-prismatic geometry. The benzoate groups coordinate each Pb^II atom in two different ways. Two benzoate ions behave as bidentate ligands to the Pb atom, and another benzoate ion bridges the Pb atoms, forming a binuclear structure. The dimeric units are packed via O—H⋯O hydrogen bonds and π–π interactions between the aromatic rings of neighboring molecules, with centroid–centroid distances of 3.552 (2) and 3.641 (2) Å.

Related literature

For related structures, see: Li & Yang (2004 ); Mahjoub & Morsali (2002 ); Xuan et al. (2007 ); Zhu et al. (2004 ); For information on the coordination chemistry of lead, see: Shimoni-Livny et al. (1998 ).

Experimental

Crystal data

[Pb₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂(H₂O)₂]·H₂O
M_r = 1377.30
Triclinic, $[P \overline 1]$
a = 8.5639 (16) Å
b = 12.152 (2) Å
c = 12.979 (3) Å
α = 62.652 (1)°
β = 82.762 (2)°
γ = 84.701 (2)°
V = 1189.2 (4) Å³
Z = 1
Mo Kα radiation
μ = 7.15 mm⁻¹
T = 293 (2) K
0.17 × 0.15 × 0.11 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ) T_min = 0.369, T_max = 0.512 (expected range = 0.328–0.456)
8820 measured reflections
4352 independent reflections
4009 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.050
S = 1.04
4352 reflections
333 parameters
12 restraints
H-atom parameters constrained
Δρ_max = 1.06 e Å⁻³
Δρ_min = −0.72 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—O1	2.472 (2)
Pb1—N1	2.551 (2)
Pb1—N2	2.585 (3)
Pb1—O2	2.630 (2)
Pb1—O5	2.720 (2)
Pb1—O6	2.815 (2)
Pb1—O6ⁱ	2.880 (2)
Pb1—O7	2.914 (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
O3—H3⋯O5ⁱⁱ	0.82	1.84	2.658 (3)	176
O4—H4⋯O1ⁱⁱⁱ	0.82	1.93	2.738 (3)	167
O7—H2W⋯O8^iv	0.83	2.24	2.932 (6)	141
O7—H1W⋯O3^v	0.83	2.18	2.911 (5)	146
O8—H3W⋯O2^vi	0.83	2.06	2.840 (4)	157
O8—H4W⋯O2^vii	0.83	2.04	2.788 (4)	150
C15—H15⋯O8^vi	0.93	2.42	3.339 (5)	169
Symmetry codes: (ii) -x+1, -y, -z; (iii) -x+1, -y, -z+1; (iv) x-1, y-1, z; (v) -x, -y, -z; (vi) -x+1, -y+1, -z; (vii) x+1, y+1, z.

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807065075/si2047sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807065075/si2047Isup2.hkl

checkCIF report

Comment top

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) and oxygen donor ligands have been structurally characterized (Li & Yang, 2004, Mahjoub & Morsali 2002, Zhu et al. 2004). Recently, we obtained the title lead(II) complex, by reaction of lead acetate, 3-hydroxybenzoate acid, sodium hydroxide and in ethanol/water mixtures. The resulting complex is different to the polymeric chain-structure we previously reported using 2-hydroxybenzoate acid instead of 3-hydroxybenzoate acid (Xuan et al. 2007).

The crystal structure of the title compound consists of dimeric units of [Pb(C₇H₅O₃)₂(C₁₂H₈N₂)(H₂O)], related by a crystallographic inversion centre (Fig. 1), and an uncoordinated (disordered) water molecule. Each lead atom is chelated by the two N atoms of 1,10-phenanthroline (phen) with Pb—N distances of 2.551 (2), and 2.583 (3) Å, and five carbonyl O atoms of 3-hydroxyl-benzoate anions, and is coordinated by the O atom of one water molecule. The shortest Pb—O distance is 2.472 (2) Å, and the longest is 2.914 (4) Å. The weak Pb—O bridging interactions form a four-membered Pb₂O₂ quadrilateral with a Pb—Pb separation of 4.1712 (8) Å. The uncoordinated water molecule is disordered over two sites close to a crystallographic inversion centre.

In the presented structure, the crystal is stabilized by intermolecular O—H···O and C—H···O hydrogen bonding contacts (Table 1 and Figure 2) and by two kinds of π-π stacking interactions in the sequence of benzoate - phen - phen - benzoate. The centroid-centroid distances between Cg1(N1/C1—C4/C12) and Cg2 (C21—C26)[symmetry code: -x, -y, 1 - z] and between Cg1 and Cg3 (N1/C1—C4/C12) [symmetry code: -x, 1 - y, -z] are 3.552 (2) and 3.641 (2) Å, respectively.

Related literature top

For related structures, see: Li & Yang (2004); Mahjoub & Morsali (2002); Xuan et al. (2007); Zhu et al. (2004); For information on the coordination chemistry of lead, see: Shimoni-Livny et al. (1998).

Experimental top

To a solution of 1,10-phenanthroline (0.0906 g, 0.5 mmol), 3-hydroxybenzoate acid(0.1394 g, 1 mmol) and sodium hydroxide (0.0185 g,0.5 mmol) in ethanol/water (v:v=1:1,20 ml) was added a solution of Pb(CH₃COO)₂.3H₂O (0.1903 g, 0.5 mmol) in distilled water (5 ml). The resulting solution was stirred for 5 h at 323 K and then a white precipitate was filtered. Block single crystals were obtained by slow evaporation of the filtrate after 2 d, one of which was selected for the X-ray experiment.

Structure description top

For related structures, see: Li & Yang (2004); Mahjoub & Morsali (2002); Xuan et al. (2007); Zhu et al. (2004); For information on the coordination chemistry of lead, see: Shimoni-Livny et al. (1998).

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL (Bruker, 1997).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms. [Symmetry codes for atoms labelled a: -x, -y, 1 - z].
	Fig. 2. The π-π interactions between the aromatic rings of the title compound.

Bis(µ-3-hydroxybenzoato-κ³O,O':O)bis[aqua(3-hydroxybenzoato- κ²O,O')(1,10-phenanthroline-κ²N,N')lead(II)] monohydrate top

Crystal data top

[Pb₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂(H₂O)₂]·H₂O	Z = 1
M_r = 1377.30	F(000) = 666
Triclinic, P1	D_x = 1.923 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5639 (16) Å	Cell parameters from 5362 reflections
b = 12.152 (2) Å	θ = 2.4–27.5°
c = 12.979 (3) Å	µ = 7.15 mm⁻¹
α = 62.652 (1)°	T = 293 K
β = 82.762 (2)°	Block, yellow
γ = 84.701 (2)°	0.17 × 0.15 × 0.11 mm
V = 1189.2 (4) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4352 independent reflections
Radiation source: fine-focus sealed tube	4009 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
phi and ω scans	θ_max = 25.5°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −10→10
T_min = 0.369, T_max = 0.512	k = −14→14
8820 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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.050	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0263P)²] where P = (F_o² + 2F_c²)/3
4352 reflections	(Δ/σ)_max < 0.001
333 parameters	Δρ_max = 1.06 e Å⁻³
12 restraints	Δρ_min = −0.72 e Å⁻³

Crystal data top

[Pb₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂(H₂O)₂]·H₂O	γ = 84.701 (2)°
M_r = 1377.30	V = 1189.2 (4) Å³
Triclinic, P1	Z = 1
a = 8.5639 (16) Å	Mo Kα radiation
b = 12.152 (2) Å	µ = 7.15 mm⁻¹
c = 12.979 (3) Å	T = 293 K
α = 62.652 (1)°	0.17 × 0.15 × 0.11 mm
β = 82.762 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4352 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1997)	4009 reflections with I > 2σ(I)
T_min = 0.369, T_max = 0.512	R_int = 0.022
8820 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	12 restraints
wR(F²) = 0.050	H-atom parameters constrained
S = 1.04	Δρ_max = 1.06 e Å⁻³
4352 reflections	Δρ_min = −0.72 e Å⁻³
333 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	Occ. (<1)
Pb1	0.062168 (13)	0.070072 (10)	0.321211 (9)	0.02816 (4)
O1	0.3051 (3)	0.1587 (2)	0.19470 (18)	0.0387 (6)
O2	0.1526 (3)	0.0939 (2)	0.1109 (2)	0.0450 (6)
O3	0.4628 (3)	0.1416 (3)	−0.2612 (2)	0.0520 (7)
H3	0.5442	0.1402	−0.3015	0.078*
O4	0.5876 (3)	−0.3747 (2)	0.8277 (2)	0.0480 (7)
H4	0.6085	−0.3047	0.8146	0.072*
O5	0.2736 (3)	−0.1258 (2)	0.38683 (19)	0.0522 (7)
O6	0.2135 (3)	−0.0679 (2)	0.5260 (2)	0.0434 (6)
O7	−0.1913 (5)	−0.0008 (4)	0.2362 (4)	0.1267 (16)
H2W	−0.1381	−0.0498	0.2158	0.190*
H1W	−0.2871	−0.0133	0.2430	0.190*
N1	−0.0483 (3)	0.2875 (2)	0.1953 (2)	0.0306 (6)
N2	0.1144 (3)	0.2374 (2)	0.3819 (2)	0.0307 (6)
C1	−0.1321 (4)	0.3108 (3)	0.1076 (3)	0.0361 (8)
H1	−0.1418	0.2470	0.0884	0.043*
C2	−0.2063 (4)	0.4251 (3)	0.0427 (3)	0.0441 (9)
H2	−0.2649	0.4371	−0.0175	0.053*
C3	−0.1904 (4)	0.5195 (3)	0.0703 (3)	0.0459 (10)
H3A	−0.2386	0.5968	0.0283	0.055*
C4	−0.1018 (4)	0.5004 (3)	0.1615 (3)	0.0374 (8)
C5	−0.0782 (5)	0.5954 (3)	0.1930 (3)	0.0483 (10)
H5	−0.1212	0.6747	0.1508	0.058*
C6	0.0051 (5)	0.5725 (3)	0.2824 (3)	0.0478 (9)
H6	0.0203	0.6366	0.2999	0.057*
C7	0.0717 (4)	0.4497 (3)	0.3521 (3)	0.0378 (8)
C8	0.1538 (4)	0.4193 (3)	0.4492 (3)	0.0441 (9)
H8A	0.1677	0.4799	0.4718	0.053*
C9	0.2131 (4)	0.3020 (3)	0.5105 (3)	0.0448 (9)
H9	0.2658	0.2813	0.5758	0.054*
C10	0.1931 (4)	0.2129 (3)	0.4735 (3)	0.0380 (8)
H10	0.2364	0.1334	0.5143	0.046*
C11	0.0534 (4)	0.3546 (3)	0.3214 (3)	0.0289 (7)
C12	−0.0336 (4)	0.3809 (3)	0.2236 (3)	0.0295 (7)
C13	0.2813 (4)	0.1357 (3)	0.1119 (3)	0.0308 (7)
C14	0.4093 (4)	0.1573 (3)	0.0144 (2)	0.0280 (7)
C15	0.3806 (4)	0.1410 (3)	−0.0805 (3)	0.0334 (7)
H15	0.2814	0.1187	−0.0845	0.040*
C16	0.4984 (4)	0.1575 (3)	−0.1691 (3)	0.0327 (8)
C17	0.6472 (4)	0.1886 (3)	−0.1626 (3)	0.0358 (8)
H17	0.7273	0.1990	−0.2215	0.043*
C18	0.6748 (4)	0.2039 (3)	−0.0677 (3)	0.0418 (9)
H18	0.7747	0.2245	−0.0630	0.050*
C19	0.5578 (4)	0.1895 (3)	0.0204 (3)	0.0377 (8)
H19	0.5784	0.2013	0.0833	0.045*
C20	0.2779 (4)	−0.1430 (3)	0.4891 (3)	0.0322 (7)
C21	0.3627 (4)	−0.2582 (3)	0.5717 (3)	0.0287 (7)
C22	0.3647 (4)	−0.3663 (3)	0.5590 (3)	0.0362 (8)
H22	0.3189	−0.3653	0.4972	0.043*
C23	0.4342 (4)	−0.4746 (3)	0.6377 (3)	0.0407 (9)
H23	0.4334	−0.5467	0.6297	0.049*
C24	0.5050 (4)	−0.4762 (3)	0.7280 (3)	0.0380 (8)
H24	0.5493	−0.5500	0.7819	0.046*
C25	0.5104 (4)	−0.3681 (3)	0.7388 (3)	0.0328 (7)
C26	0.4352 (3)	−0.2600 (3)	0.6630 (2)	0.0314 (7)
H26	0.4332	−0.1888	0.6729	0.038*
O8	0.9880 (3)	0.9421 (3)	0.0575 (2)	0.103 (2)	0.50
H4W	1.0384	1.0024	0.0467	0.154*	0.50
H3W	0.9574	0.9510	−0.0041	0.154*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.03033 (7)	0.03078 (6)	0.02384 (6)	0.00001 (5)	−0.00074 (4)	−0.01346 (4)
O1	0.0418 (13)	0.0503 (12)	0.0318 (11)	−0.0092 (11)	0.0047 (10)	−0.0258 (10)
O2	0.0358 (13)	0.0690 (15)	0.0427 (12)	−0.0154 (12)	0.0085 (10)	−0.0365 (11)
O3	0.0463 (14)	0.0861 (17)	0.0366 (12)	0.0002 (14)	−0.0001 (11)	−0.0404 (12)
O4	0.0576 (15)	0.0449 (13)	0.0401 (13)	−0.0025 (12)	−0.0190 (12)	−0.0144 (11)
O5	0.0574 (16)	0.0655 (16)	0.0298 (12)	0.0260 (13)	−0.0087 (11)	−0.0221 (11)
O6	0.0515 (14)	0.0408 (12)	0.0395 (12)	0.0126 (11)	−0.0056 (11)	−0.0218 (10)
O7	0.131 (3)	0.131 (3)	0.103 (3)	−0.056 (3)	−0.046 (2)	−0.022 (2)
N1	0.0349 (14)	0.0329 (13)	0.0244 (12)	−0.0006 (11)	−0.0032 (11)	−0.0134 (10)
N2	0.0330 (14)	0.0342 (13)	0.0273 (12)	−0.0009 (11)	−0.0040 (11)	−0.0159 (11)
C1	0.0363 (18)	0.0417 (17)	0.0321 (16)	−0.0016 (15)	−0.0064 (14)	−0.0174 (14)
C2	0.0355 (18)	0.056 (2)	0.0338 (17)	0.0024 (16)	−0.0093 (15)	−0.0136 (16)
C3	0.042 (2)	0.0385 (19)	0.0391 (19)	0.0104 (16)	−0.0059 (16)	−0.0042 (16)
C4	0.0339 (17)	0.0318 (16)	0.0377 (18)	0.0040 (14)	0.0045 (14)	−0.0110 (14)
C5	0.053 (2)	0.0311 (17)	0.056 (2)	0.0018 (16)	0.0011 (18)	−0.0178 (16)
C6	0.053 (2)	0.0379 (17)	0.062 (2)	−0.0040 (16)	0.0052 (19)	−0.0321 (16)
C7	0.0340 (18)	0.0421 (17)	0.0423 (18)	−0.0092 (14)	0.0076 (14)	−0.0248 (15)
C8	0.044 (2)	0.0540 (19)	0.0528 (19)	−0.0092 (16)	0.0033 (16)	−0.0403 (16)
C9	0.0399 (19)	0.066 (2)	0.0413 (18)	−0.0040 (17)	−0.0087 (15)	−0.0332 (17)
C10	0.0393 (18)	0.0449 (18)	0.0315 (16)	−0.0023 (15)	−0.0077 (14)	−0.0175 (14)
C11	0.0262 (15)	0.0340 (15)	0.0259 (14)	−0.0047 (13)	0.0056 (12)	−0.0143 (12)
C12	0.0252 (15)	0.0335 (15)	0.0272 (14)	−0.0019 (13)	0.0043 (12)	−0.0132 (13)
C13	0.0339 (17)	0.0332 (15)	0.0280 (15)	0.0006 (13)	−0.0014 (13)	−0.0169 (13)
C14	0.0308 (16)	0.0264 (14)	0.0255 (14)	−0.0002 (12)	0.0007 (12)	−0.0116 (12)
C15	0.0303 (16)	0.0347 (16)	0.0356 (16)	0.0043 (13)	−0.0066 (13)	−0.0164 (13)
C16	0.0411 (18)	0.0348 (16)	0.0232 (14)	0.0035 (14)	−0.0013 (13)	−0.0153 (13)
C17	0.0363 (18)	0.0410 (17)	0.0296 (15)	−0.0027 (14)	0.0079 (14)	−0.0180 (14)
C18	0.0264 (16)	0.058 (2)	0.0475 (19)	−0.0090 (15)	0.0015 (15)	−0.0297 (16)
C19	0.0385 (18)	0.0504 (18)	0.0347 (16)	−0.0089 (15)	0.0001 (14)	−0.0278 (14)
C20	0.0292 (16)	0.0397 (17)	0.0277 (15)	−0.0002 (14)	0.0016 (13)	−0.0166 (13)
C21	0.0268 (15)	0.0351 (15)	0.0258 (14)	−0.0024 (13)	0.0055 (12)	−0.0171 (12)
C22	0.0376 (18)	0.0427 (17)	0.0359 (16)	−0.0009 (15)	−0.0046 (14)	−0.0242 (14)
C23	0.049 (2)	0.0305 (16)	0.0469 (19)	−0.0009 (15)	−0.0002 (16)	−0.0221 (14)
C24	0.0401 (19)	0.0307 (16)	0.0395 (18)	0.0051 (14)	−0.0032 (15)	−0.0141 (14)
C25	0.0321 (16)	0.0363 (16)	0.0290 (15)	−0.0035 (14)	−0.0029 (13)	−0.0136 (13)
C26	0.0384 (18)	0.0300 (15)	0.0278 (15)	−0.0020 (13)	−0.0008 (13)	−0.0154 (12)
O8	0.086 (4)	0.127 (5)	0.137 (5)	−0.018 (4)	−0.024 (4)	−0.089 (4)

Geometric parameters (Å, º) top

Pb1—O1	2.472 (2)	C5—H5	0.9300
Pb1—N1	2.551 (2)	C6—C7	1.450 (5)
Pb1—N2	2.585 (3)	C6—H6	0.9300
Pb1—O2	2.630 (2)	C7—C8	1.402 (5)
Pb1—O5	2.720 (2)	C7—C11	1.411 (5)
Pb1—O6	2.815 (2)	C8—C9	1.360 (5)
Pb1—O6ⁱ	2.880 (2)	C8—H8A	0.9300
Pb1—O7	2.914 (4)	C9—C10	1.402 (5)
Pb1—C13	2.922 (3)	C9—H9	0.9300
Pb1—C20	3.133 (3)	C10—H10	0.9300
Pb1—Pb1ⁱ	4.1712 (8)	C11—C12	1.445 (4)
O1—C13	1.272 (4)	C13—C14	1.507 (4)
O2—C13	1.258 (4)	C14—C19	1.387 (4)
O3—C16	1.369 (4)	C14—C15	1.388 (5)
O3—H3	0.82	C15—C16	1.383 (4)
O4—C25	1.368 (4)	C15—H15	0.9300
O4—H4	0.82	C16—C17	1.386 (5)
O5—C20	1.250 (4)	C17—C18	1.378 (5)
O6—C20	1.268 (4)	C17—H17	0.9300
O6—Pb1ⁱ	2.880 (2)	C18—C19	1.379 (5)
O7—H2W	0.83	C18—H18	0.9300
O7—H1W	0.83	C19—H19	0.9300
N1—C1	1.327 (4)	C20—C21	1.505 (4)
N1—C12	1.365 (4)	C21—C22	1.396 (5)
N2—C10	1.341 (4)	C21—C26	1.396 (4)
N2—C11	1.362 (4)	C22—C23	1.380 (4)
C1—C2	1.393 (5)	C22—H22	0.9300
C1—H1	0.9300	C23—C24	1.377 (5)
C2—C3	1.372 (6)	C23—H23	0.9300
C2—H2	0.9300	C24—C25	1.390 (5)
C3—C4	1.405 (5)	C24—H24	0.9300
C3—H3A	0.9300	C25—C26	1.387 (4)
C4—C12	1.409 (4)	C26—H26	0.9300
C4—C5	1.427 (5)	O8—H4W	0.83
C5—C6	1.344 (6)	O8—H3W	0.83

O1—Pb1—N1	81.43 (8)	C2—C3—H3A	119.7
O1—Pb1—N2	78.87 (8)	C4—C3—H3A	119.7
N1—Pb1—N2	64.53 (8)	C3—C4—C12	117.3 (3)
O1—Pb1—O2	50.98 (7)	C3—C4—C5	123.2 (3)
N1—Pb1—O2	78.90 (8)	C12—C4—C5	119.4 (3)
N2—Pb1—O2	121.76 (8)	C6—C5—C4	121.3 (3)
O1—Pb1—O5	76.29 (8)	C6—C5—H5	119.4
N1—Pb1—O5	157.21 (8)	C4—C5—H5	119.4
N2—Pb1—O5	114.84 (8)	C5—C6—C7	121.3 (4)
O2—Pb1—O5	83.37 (7)	C5—C6—H6	119.3
O1—Pb1—O6	95.43 (7)	C7—C6—H6	119.3
N1—Pb1—O6	141.71 (8)	C8—C7—C11	117.6 (3)
N2—Pb1—O6	77.37 (7)	C8—C7—C6	123.7 (3)
O2—Pb1—O6	127.92 (7)	C11—C7—C6	118.7 (3)
O5—Pb1—O6	47.03 (7)	C9—C8—C7	120.5 (3)
O1—Pb1—O6ⁱ	154.52 (8)	C9—C8—H8A	119.8
N1—Pb1—O6ⁱ	81.97 (7)	C7—C8—H8A	119.8
N2—Pb1—O6ⁱ	76.57 (8)	C8—C9—C10	118.7 (3)
O2—Pb1—O6ⁱ	142.57 (7)	C8—C9—H9	120.6
O5—Pb1—O6ⁱ	120.61 (7)	C10—C9—H9	120.6
O6—Pb1—O6ⁱ	85.82 (7)	N2—C10—C9	122.8 (3)
O1—Pb1—O7	121.36 (10)	N2—C10—H10	118.6
N1—Pb1—O7	82.17 (10)	C9—C10—H10	118.6
N2—Pb1—O7	138.64 (12)	N2—C11—C7	122.0 (3)
O2—Pb1—O7	70.71 (11)	N2—C11—C12	118.5 (3)
O5—Pb1—O7	105.38 (11)	C7—C11—C12	119.5 (3)
O6—Pb1—O7	129.11 (9)	N1—C12—C4	122.0 (3)
O6ⁱ—Pb1—O7	75.04 (11)	N1—C12—C11	118.3 (3)
O1—Pb1—C13	25.58 (8)	C4—C12—C11	119.7 (3)
N1—Pb1—C13	80.73 (8)	O2—C13—O1	120.8 (3)
N2—Pb1—C13	101.53 (9)	O2—C13—C14	119.6 (3)
O2—Pb1—C13	25.51 (8)	O1—C13—C14	119.6 (3)
O5—Pb1—C13	77.12 (8)	O2—C13—Pb1	64.14 (16)
O6—Pb1—C13	111.91 (8)	O1—C13—Pb1	57.02 (15)
O6ⁱ—Pb1—C13	161.54 (8)	C14—C13—Pb1	172.4 (2)
O7—Pb1—C13	96.18 (11)	C19—C14—C15	119.5 (3)
O1—Pb1—C20	87.16 (8)	C19—C14—C13	120.5 (3)
N1—Pb1—C20	160.33 (9)	C15—C14—C13	120.0 (3)
N2—Pb1—C20	97.64 (8)	C16—C15—C14	120.6 (3)
O2—Pb1—C20	106.12 (8)	C16—C15—H15	119.7
O5—Pb1—C20	23.32 (8)	C14—C15—H15	119.7
O6—Pb1—C20	23.85 (8)	O3—C16—C15	118.0 (3)
O6ⁱ—Pb1—C20	102.71 (7)	O3—C16—C17	122.0 (3)
O7—Pb1—C20	117.50 (11)	C15—C16—C17	120.0 (3)
C13—Pb1—C20	95.75 (8)	C18—C17—C16	119.0 (3)
O1—Pb1—Pb1ⁱ	133.40 (5)	C18—C17—H17	120.5
N1—Pb1—Pb1ⁱ	115.68 (6)	C16—C17—H17	120.5
N2—Pb1—Pb1ⁱ	72.07 (5)	C17—C18—C19	121.6 (3)
O2—Pb1—Pb1ⁱ	164.35 (5)	C17—C18—H18	119.2
O5—Pb1—Pb1ⁱ	83.78 (5)	C19—C18—H18	119.2
O6—Pb1—Pb1ⁱ	43.51 (5)	C18—C19—C14	119.3 (3)
O6ⁱ—Pb1—Pb1ⁱ	42.31 (4)	C18—C19—H19	120.3
O7—Pb1—Pb1ⁱ	104.33 (9)	C14—C19—H19	120.3
C13—Pb1—Pb1ⁱ	155.04 (6)	O5—C20—O6	122.8 (3)
C20—Pb1—Pb1ⁱ	62.27 (6)	O5—C20—C21	118.3 (3)
C13—O1—Pb1	97.40 (19)	O6—C20—C21	118.9 (3)
C13—O2—Pb1	90.36 (19)	O5—C20—Pb1	59.49 (17)
C16—O3—H3	109.5	O6—C20—Pb1	63.89 (16)
C25—O4—H4	109.5	C21—C20—Pb1	171.4 (2)
C20—O5—Pb1	97.2 (2)	C22—C21—C26	119.4 (3)
C20—O6—Pb1	92.26 (18)	C22—C21—C20	119.4 (3)
C20—O6—Pb1ⁱ	134.9 (2)	C26—C21—C20	121.2 (3)
Pb1—O6—Pb1ⁱ	94.18 (7)	C23—C22—C21	120.2 (3)
Pb1—O7—H2W	97.5	C23—C22—H22	119.9
Pb1—O7—H1W	147.1	C21—C22—H22	119.9
H2W—O7—H1W	110.3	C24—C23—C22	120.3 (3)
C1—N1—C12	118.2 (3)	C24—C23—H23	119.9
C1—N1—Pb1	121.6 (2)	C22—C23—H23	119.9
C12—N1—Pb1	119.89 (19)	C23—C24—C25	120.2 (3)
C10—N2—C11	118.3 (3)	C23—C24—H24	119.9
C10—N2—Pb1	122.9 (2)	C25—C24—H24	119.9
C11—N2—Pb1	118.7 (2)	O4—C25—C26	122.7 (3)
N1—C1—C2	123.9 (3)	O4—C25—C24	117.5 (3)
N1—C1—H1	118.1	C26—C25—C24	119.9 (3)
C2—C1—H1	118.1	C25—C26—C21	119.9 (3)
C3—C2—C1	118.0 (3)	C25—C26—H26	120.0
C3—C2—H2	121.0	C21—C26—H26	120.0
C1—C2—H2	121.0	H4W—O8—H3W	111.2
C2—C3—C4	120.6 (3)

O2—Pb1—O1—C13	−3.8 (2)	O5—Pb1—O6ⁱ—Pb1ⁱ	33.16 (11)
O5—Pb1—O1—C13	88.8 (2)	O5—Pb1—O6ⁱ—C20ⁱ	130.5 (3)
O6—Pb1—O1—C13	132.1 (2)	O6—Pb1—O6ⁱ—Pb1ⁱ	0.00 (8)
O7—Pb1—O1—C13	−11.1 (3)	O6—Pb1—O6ⁱ—C20ⁱ	97.3 (3)
N1—Pb1—O1—C13	−86.4 (2)	O7—Pb1—O6ⁱ—Pb1ⁱ	132.41 (12)
N2—Pb1—O1—C13	−152.0 (2)	O7—Pb1—O6ⁱ—C20ⁱ	−130.3 (3)
O6ⁱ—Pb1—O1—C13	−136.3 (2)	N1—Pb1—O6ⁱ—Pb1ⁱ	−143.59 (9)
O1—Pb1—O2—C13	3.8 (2)	N1—Pb1—O6ⁱ—C20ⁱ	−46.3 (3)
O5—Pb1—O2—C13	−73.9 (2)	N2—Pb1—O6ⁱ—Pb1ⁱ	−77.99 (8)
O6—Pb1—O2—C13	−57.7 (2)	N2—Pb1—O6ⁱ—C20ⁱ	19.3 (3)
O7—Pb1—O2—C13	177.2 (2)	Pb1—O1—C13—O2	7.2 (4)
N1—Pb1—O2—C13	91.7 (2)	Pb1—O1—C13—C14	−172.1 (3)
N2—Pb1—O2—C13	41.3 (2)	Pb1—O2—C13—O1	−6.7 (4)
O6ⁱ—Pb1—O2—C13	152.4 (2)	Pb1—O2—C13—C14	172.6 (3)
O1—Pb1—O5—C20	115.9 (2)	Pb1—O5—C20—O6	−9.3 (4)
O2—Pb1—O5—C20	167.3 (2)	Pb1—O5—C20—C21	170.4 (3)
O6—Pb1—O5—C20	4.8 (2)	Pb1—O6—C20—O5	8.9 (4)
O7—Pb1—O5—C20	−124.9 (2)	Pb1—O6—C20—C21	−170.8 (3)
N1—Pb1—O5—C20	128.3 (2)	Pb1ⁱ—O6—C20—O5	107.1 (4)
N2—Pb1—O5—C20	45.3 (2)	Pb1ⁱ—O6—C20—C21	−72.7 (4)
C13—Pb1—O5—C20	142.2 (2)	Pb1—N1—C1—C2	174.3 (3)
O6ⁱ—Pb1—O5—C20	−43.4 (2)	C12—N1—C1—C2	−0.1 (5)
O1—Pb1—O6—C20	−70.3 (2)	Pb1—N1—C12—C4	−175.6 (2)
O1—Pb1—O6—Pb1ⁱ	154.47 (8)	Pb1—N1—C12—C11	3.6 (4)
O2—Pb1—O6—C20	−27.0 (2)	C1—N1—C12—C4	−1.2 (5)
O2—Pb1—O6—Pb1ⁱ	−162.22 (8)	C1—N1—C12—C11	178.1 (3)
O5—Pb1—O6—C20	−4.69 (19)	Pb1—N2—C10—C9	−176.0 (2)
O5—Pb1—O6—Pb1ⁱ	−139.97 (12)	C11—N2—C10—C9	1.0 (5)
O7—Pb1—O6—C20	68.4 (2)	Pb1—N2—C11—C7	177.5 (2)
O7—Pb1—O6—Pb1ⁱ	−66.84 (15)	Pb1—N2—C11—C12	−1.9 (4)
N1—Pb1—O6—C20	−153.3 (2)	C10—N2—C11—C7	0.4 (5)
N1—Pb1—O6—Pb1ⁱ	71.43 (13)	C10—N2—C11—C12	−179.1 (3)
N2—Pb1—O6—C20	−147.6 (2)	N1—C1—C2—C3	0.7 (5)
N2—Pb1—O6—Pb1ⁱ	77.17 (8)	C1—C2—C3—C4	−0.1 (5)
C13—Pb1—O6—C20	−50.1 (2)	C2—C3—C4—C5	178.7 (3)
C13—Pb1—O6—Pb1ⁱ	174.66 (9)	C2—C3—C4—C12	−1.1 (5)
O6ⁱ—Pb1—O6—C20	135.3 (2)	C3—C4—C5—C6	178.7 (4)
O6ⁱ—Pb1—O6—Pb1ⁱ	0.00 (8)	C12—C4—C5—C6	−1.4 (6)
O1—Pb1—N1—C1	100.8 (2)	C3—C4—C12—N1	1.8 (5)
O1—Pb1—N1—C12	−84.9 (2)	C3—C4—C12—C11	−177.5 (3)
O2—Pb1—N1—C1	49.1 (2)	C5—C4—C12—N1	−178.1 (3)
O2—Pb1—N1—C12	−136.6 (2)	C5—C4—C12—C11	2.7 (5)
O5—Pb1—N1—C1	88.7 (3)	C4—C5—C6—C7	−1.3 (6)
O5—Pb1—N1—C12	−97.1 (3)	C5—C6—C7—C8	−177.2 (4)
O6—Pb1—N1—C1	−171.3 (2)	C5—C6—C7—C11	2.7 (6)
O6—Pb1—N1—C12	3.0 (3)	C6—C7—C8—C9	−180.0 (3)
O7—Pb1—N1—C1	−22.7 (3)	C11—C7—C8—C9	0.1 (5)
O7—Pb1—N1—C12	151.6 (2)	C6—C7—C11—N2	179.2 (3)
N2—Pb1—N1—C1	−177.5 (3)	C6—C7—C11—C12	−1.4 (5)
N2—Pb1—N1—C12	−3.2 (2)	C8—C7—C11—N2	−0.9 (5)
C13—Pb1—N1—C1	75.0 (2)	C8—C7—C11—C12	178.6 (3)
C13—Pb1—N1—C12	−110.8 (2)	C7—C8—C9—C10	1.2 (5)
O6ⁱ—Pb1—N1—C1	−98.6 (2)	C8—C9—C10—N2	−1.8 (5)
O6ⁱ—Pb1—N1—C12	75.7 (2)	N2—C11—C12—N1	−1.1 (5)
O1—Pb1—N2—C10	−94.7 (2)	N2—C11—C12—C4	178.2 (3)
O1—Pb1—N2—C11	88.3 (2)	C7—C11—C12—N1	179.5 (3)
O2—Pb1—N2—C10	−123.5 (2)	C7—C11—C12—C4	−1.3 (5)
O2—Pb1—N2—C11	59.5 (2)	O1—C13—C14—C15	−175.4 (3)
O5—Pb1—N2—C10	−25.6 (3)	O1—C13—C14—C19	6.8 (5)
O5—Pb1—N2—C11	157.4 (2)	O2—C13—C14—C15	5.3 (5)
O6—Pb1—N2—C10	3.5 (2)	O2—C13—C14—C19	−172.5 (3)
O6—Pb1—N2—C11	−173.5 (2)	C13—C14—C15—C16	−178.4 (3)
O7—Pb1—N2—C10	139.9 (3)	C19—C14—C15—C16	−0.5 (6)
O7—Pb1—N2—C11	−37.1 (3)	C13—C14—C19—C18	177.4 (3)
N1—Pb1—N2—C10	179.6 (3)	C15—C14—C19—C18	−0.5 (6)
N1—Pb1—N2—C11	2.6 (2)	C14—C15—C16—O3	−179.2 (4)
C13—Pb1—N2—C10	−106.6 (2)	C14—C15—C16—C17	1.1 (6)
C13—Pb1—N2—C11	76.4 (2)	O3—C16—C17—C18	179.6 (4)
O6ⁱ—Pb1—N2—C10	92.2 (2)	C15—C16—C17—C18	−0.7 (6)
O6ⁱ—Pb1—N2—C11	−84.8 (2)	C16—C17—C18—C19	−0.3 (6)
O1—Pb1—C13—O2	−173.1 (4)	C17—C18—C19—C14	0.9 (6)
O2—Pb1—C13—O1	173.1 (4)	O5—C20—C21—C22	−31.7 (5)
O5—Pb1—C13—O1	−85.1 (2)	O5—C20—C21—C26	150.3 (3)
O5—Pb1—C13—O2	101.8 (2)	O6—C20—C21—C22	148.0 (3)
O6—Pb1—C13—O1	−52.8 (2)	O6—C20—C21—C26	−30.0 (5)
O6—Pb1—C13—O2	134.1 (2)	C20—C21—C22—C23	−176.4 (3)
O7—Pb1—C13—O1	170.5 (2)	C26—C21—C22—C23	1.6 (5)
O7—Pb1—C13—O2	−2.6 (2)	C20—C21—C26—C25	179.0 (3)
N1—Pb1—C13—O1	89.5 (2)	C22—C21—C26—C25	1.0 (5)
N1—Pb1—C13—O2	−83.6 (2)	C21—C22—C23—C24	−1.4 (5)
N2—Pb1—C13—O1	28.1 (2)	C22—C23—C24—C25	−1.6 (5)
N2—Pb1—C13—O2	−145.1 (2)	C23—C24—C25—O4	−177.6 (3)
O1—Pb1—O6ⁱ—Pb1ⁱ	−93.85 (17)	C23—C24—C25—C26	4.3 (5)
O1—Pb1—O6ⁱ—C20ⁱ	3.5 (4)	O4—C25—C26—C21	178.0 (3)
O2—Pb1—O6ⁱ—Pb1ⁱ	156.67 (10)	C24—C25—C26—C21	−4.0 (5)
O2—Pb1—O6ⁱ—C20ⁱ	−106.0 (3)

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
O3—H3···O5ⁱⁱ	0.82	1.84	2.658 (3)	176
O4—H4···O1ⁱⁱⁱ	0.82	1.93	2.738 (3)	167
O7—H2W···O8^iv	0.83	2.24	2.932 (6)	141
O7—H1W···O3^v	0.83	2.18	2.911 (5)	146
O8—H3W···O2^vi	0.83	2.06	2.840 (4)	157
O8—H4W···O2^vii	0.83	2.04	2.788 (4)	150
C15—H15···O8^vi	0.93	2.42	3.339 (5)	169

Symmetry codes: (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) x−1, y−1, z; (v) −x, −y, −z; (vi) −x+1, −y+1, −z; (vii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formula	[Pb₂(C₇H₅O₃)₄(C₁₂H₈N₂)₂(H₂O)₂]·H₂O
M_r	1377.30
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	8.5639 (16), 12.152 (2), 12.979 (3)
α, β, γ (°)	62.652 (1), 82.762 (2), 84.701 (2)
V (Å³)	1189.2 (4)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	7.15
Crystal size (mm)	0.17 × 0.15 × 0.11

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1997)
T_min, T_max	0.369, 0.512
No. of measured, independent and observed [I > 2σ(I)] reflections	8820, 4352, 4009
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.050, 1.04
No. of reflections	4352
No. of parameters	333
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.06, −0.72

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).

Selected bond lengths (Å) top

Pb1—O1	2.472 (2)	Pb1—O5	2.720 (2)
Pb1—N1	2.551 (2)	Pb1—O6	2.815 (2)
Pb1—N2	2.585 (3)	Pb1—O6ⁱ	2.880 (2)
Pb1—O2	2.630 (2)	Pb1—O7	2.914 (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
O3—H3···O5ⁱⁱ	0.82	1.84	2.658 (3)	176
O4—H4···O1ⁱⁱⁱ	0.82	1.93	2.738 (3)	167
O7—H2W···O8^iv	0.83	2.24	2.932 (6)	141
O7—H1W···O3^v	0.83	2.18	2.911 (5)	146
O8—H3W···O2^vi	0.83	2.06	2.840 (4)	157
O8—H4W···O2^vii	0.83	2.04	2.788 (4)	150
C15—H15···O8^vi	0.93	2.42	3.339 (5)	169

Symmetry codes: (ii) −x+1, −y, −z; (iii) −x+1, −y, −z+1; (iv) x−1, y−1, z; (v) −x, −y, −z; (vi) −x+1, −y+1, −z; (vii) x+1, y+1, z.

Acknowledgements

Financial support by the Science Fund of Henan Province for Distinguished Young Scholars (No. 074100510005) is gratefully acknowledged.

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