(2,2′-Bipyridine-κ2N,N′)bis­(4-hydroxy­benzoato-κ2O,O′)lead(II) monohydrate

Dai, J.; Yang, J.

doi:10.1107/S1600536810002941

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m237

https://doi.org/10.1107/S1600536810002941

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(2,2′-Bipyridine-κ²N,N′)bis(4-hydroxybenzoato-κ²O,O′)lead(II) monohydrate

Jun Dai ^a and Juan Yang ^b ^*

^aInstitute of Safety Science and Engineering, Henan Polytechnic University, Jiaozuo 454003, People's Republic of China, and ^bDepartment of Physical Chemistry, Henan Polytechnic University, Jiaozuo 454003, People's Republic of China
^*Correspondence e-mail: yangjuan0302@yahoo.cn

(Received 27 December 2009; accepted 24 January 2010; online 30 January 2010)

The reaction of lead acetate, 4-hydroxybenzoic acid and 2,2′-bipyridine in aqueous solution gave the title complex, [Pb(C₇H₅O₃)₂(C₁₀H₈N₂)]·H₂O. The asymmetric unit contains one Pb^II atom, two 4-hydroxybenzoate ligands, one 2,2′-bipyridine ligand and one uncoordinated water molecule. The Pb^II atom is hexacoordinated in a distorted tetragonal-bipyramidal geometry and is chelated by four carboxylate O atoms and two N atoms. O—H⋯O hydrogen-bonding interactions, involving the uncoordinated water, the carboxylate O atoms and hydroxy O atoms, produce a three-dimensional supramolecular structure.

Related literature

For general background to the potential applications of lead compounds, see: Fan & Zhu (2006 ); Hamilton et al. (2004 ); Shi et al. (2007 ). For the use of aromatic carboxylate ligands in the preparation of metal-organic complexes, see: Wang et al. (2006 ); Masaoka et al. (2001 ). For related lead structures, see: Shi et al. (2007).

Experimental

Crystal data

[Pb(C₇H₅O₃)₂(C₁₀H₈N₂)]·H₂O
M_r = 655.61
Monoclinic, P 2₁ /c
a = 10.9483 (4) Å
b = 17.5194 (6) Å
c = 12.0479 (4) Å
β = 100.334 (2)°
V = 2273.39 (14) Å³
Z = 4
Mo Kα radiation
μ = 7.47 mm⁻¹
T = 296 K
0.35 × 0.26 × 0.21 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007 ) T_min = 0.180, T_max = 0.303
18618 measured reflections
4067 independent reflections
3579 reflections with I > σ(I)
R_int = 0.037

Refinement

R[F² > 2σ(F²)] = 0.025
wR(F²) = 0.072
S = 1.01
4067 reflections
315 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 1.05 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O1ⁱ	0.82	1.90	2.671 (4)	157
O3—H3A⋯O1W	0.82	1.89	2.695 (5)	166
O1W—H1A⋯O5ⁱⁱ	0.90 (3)	2.04 (3)	2.849 (4)	148 (5)
O1W—H1B⋯O4ⁱⁱⁱ	0.83 (3)	2.00 (3)	2.789 (4)	158 (5)
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810002941/pk2224sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002941/pk2224Isup2.hkl

checkCIF report

Comment top

Recently, lead compounds have been increasingly studied owing to their possible applications in different fields (Fan & Zhu 2006; Hamilton et al. 2004; Shi et al. 2007), such as ion-exchange, non-linear optics and catalysis. Environmental and biological concerns are due to the toxicity of lead and its diverse interactions with biological systems. As an important family of multidentate O-donor ligands, aromatic carboxylate ligands have been extensively employed in the preparation of metal-organic complexes because of their potential properties and intriguing structural topologies (Wang et al. 2006; Masaoka et al. 2001). Herein, we report the structure of the title complex.

The asymmetric unit of the title complex, [Pb(C₂₄H₁₈O₆N₂)(H₂O)], contains a Pb^II cation, two 4-hydroxybenzonic acid ligands, one 2,2'-bipyridine and one free water molecule, as illustrated in Fig. 1. The Pb^II atom is hexacoordinate and chelated by four carboxylate O atoms from two 4-hydroxybenzoic acid and two N atoms from one 2,2'-bipyridine. The Pb—O bond lengths are in the range of 2.477 (3) to 2.625 (3) Å. The Pb—N bond lengths are 2.463 (3) to 2.562 (3) Å. The Pb^II atom has a distorted tetragonal bipyramidal geometry. The free water molecule, carboxylate O atoms and hydroxy O atoms are involved in extensive O—H···O hydrogen-bonding interactions (Table 1).

Related literature top

For general background to the potential applications of lead compounds, see: Fan & Zhu (2006); Hamilton et al. (2004); Shi et al. (2007). For the use of aromatic carboxylate ligands in the preparation of metal-organic complexes, see: Wang et al. (2006); Masaoka et al. (2001). For related lead structures, see: Shi et al. (2007).

Experimental top

A mixture of Pb(CH₃COO)₂ 3H₂O (0.199 g, 0.52 mmol), 4-hydroxybenzoic acid (0.116 g, 0.84 mmol), 2,2'-bipyridine (0.033 g, 0.21 mmol) and distilled water (10 ml) was sealed in a 25 ml Teflon-lined stainless autoclave. The mixture was heated at 403 K for 5 days to give colorless crystals suitable for X-ray diffraction analysis.

Structure description top

For general background to the potential applications of lead compounds, see: Fan & Zhu (2006); Hamilton et al. (2004); Shi et al. (2007). For the use of aromatic carboxylate ligands in the preparation of metal-organic complexes, see: Wang et al. (2006); Masaoka et al. (2001). For related lead structures, see: Shi et al. (2007).

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: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The coordination environment around Pb^II in the title complex with the atom-labeling scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 30% probability level.

(2,2'-Bipyridine-κ²N,N')bis(4-hydroxybenzoato- κ²O,O')lead(II) monohydrate top

Crystal data top

[Pb(C₇H₅O₃)₂(C₁₀H₈N₂)]·H₂O	F(000) = 1264
M_r = 655.61	D_x = 1.915 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9368 reflections
a = 10.9483 (4) Å	θ = 2.2–26.9°
b = 17.5194 (6) Å	µ = 7.47 mm⁻¹
c = 12.0479 (4) Å	T = 296 K
β = 100.334 (2)°	Block, colorless
V = 2273.39 (14) Å³	0.35 × 0.26 × 0.21 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector diffractometer	4067 independent reflections
Radiation source: fine-focus sealed tube	3579 reflections with I > σ(I)
Graphite monochromator	R_int = 0.037
φ and ω scans	θ_max = 25.1°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −13→13
T_min = 0.180, T_max = 0.303	k = −19→20
18618 measured reflections	l = −14→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)] = 0.025	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0468P)² + 0.280P] where P = (F_o² + 2F_c²)/3
4067 reflections	(Δ/σ)_max = 0.001
315 parameters	Δρ_max = 1.05 e Å⁻³
3 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Pb(C₇H₅O₃)₂(C₁₀H₈N₂)]·H₂O	V = 2273.39 (14) Å³
M_r = 655.61	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.9483 (4) Å	µ = 7.47 mm⁻¹
b = 17.5194 (6) Å	T = 296 K
c = 12.0479 (4) Å	0.35 × 0.26 × 0.21 mm
β = 100.334 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4067 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	3579 reflections with I > σ(I)
T_min = 0.180, T_max = 0.303	R_int = 0.037
18618 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.025	3 restraints
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 1.05 e Å⁻³
4067 reflections	Δρ_min = −0.61 e Å⁻³
315 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	0.261796 (15)	0.580074 (8)	0.261115 (12)	0.03852 (9)
O5	0.0806 (3)	0.64137 (15)	0.1348 (2)	0.0475 (7)
C7	0.4017 (5)	0.4162 (2)	−0.0512 (4)	0.0420 (11)
H7	0.3423	0.4505	−0.0863	0.050*
C20	0.1550 (3)	0.4657 (2)	0.4545 (3)	0.0320 (8)
O2	0.2797 (3)	0.50785 (17)	0.0880 (2)	0.0483 (7)
N2	0.2459 (3)	0.51668 (19)	0.4497 (3)	0.0404 (8)
O1	0.3906 (3)	0.45881 (15)	0.2420 (2)	0.0432 (7)
C19	0.0708 (4)	0.4488 (2)	0.3465 (3)	0.0315 (8)
C9	−0.0879 (4)	0.7114 (2)	0.1842 (3)	0.0356 (9)
C2	0.4263 (4)	0.4108 (2)	0.0654 (4)	0.0375 (9)
N1	0.0957 (3)	0.48437 (18)	0.2536 (2)	0.0380 (8)
O6	−0.3930 (3)	0.85265 (16)	0.0985 (2)	0.0482 (7)
H6A	−0.4058	0.8767	0.1536	0.072*
C21	0.1424 (5)	0.4314 (2)	0.5547 (4)	0.0408 (10)
H21	0.0775	0.3976	0.5575	0.049*
C1	0.3605 (4)	0.4621 (2)	0.1352 (3)	0.0409 (10)
C13	−0.2517 (4)	0.7641 (2)	0.0452 (3)	0.0419 (10)
H13	−0.2914	0.7679	−0.0296	0.050*
C14	−0.1501 (4)	0.7182 (2)	0.0728 (3)	0.0393 (9)
H14	−0.1217	0.6909	0.0163	0.047*
C3	0.5150 (4)	0.3590 (2)	0.1156 (3)	0.0462 (10)
H3	0.5318	0.3543	0.1937	0.055*
C10	−0.1360 (4)	0.7505 (2)	0.2682 (3)	0.0420 (10)
H10	−0.0986	0.7452	0.3435	0.050*
C12	−0.2965 (4)	0.8055 (2)	0.1294 (3)	0.0376 (9)
O4	0.0747 (3)	0.65607 (16)	0.3160 (2)	0.0503 (8)
C18	−0.0272 (4)	0.3996 (2)	0.3390 (4)	0.0424 (10)
H18	−0.0429	0.3752	0.4035	0.051*
C5	0.5550 (4)	0.3211 (2)	−0.0643 (3)	0.0399 (9)
C16	−0.0779 (5)	0.4215 (2)	0.1430 (4)	0.0555 (13)
H16	−0.1275	0.4132	0.0729	0.067*
O3	0.6169 (3)	0.2796 (2)	−0.1324 (2)	0.0587 (8)
H3A	0.6778	0.2594	−0.0940	0.088*
C17	−0.1021 (4)	0.3859 (2)	0.2378 (4)	0.0504 (11)
H17	−0.1691	0.3527	0.2332	0.061*
C4	0.5782 (4)	0.3146 (2)	0.0512 (3)	0.0461 (10)
H4	0.6371	0.2798	0.0859	0.055*
C8	0.0289 (4)	0.6673 (2)	0.2142 (3)	0.0389 (9)
C15	0.0219 (5)	0.4700 (2)	0.1548 (3)	0.0521 (12)
H15	0.0393	0.4941	0.0907	0.063*
C6	0.4647 (4)	0.3710 (2)	−0.1153 (3)	0.0466 (10)
H6	0.4462	0.3740	−0.1936	0.056*
C11	−0.2373 (4)	0.7962 (3)	0.2403 (3)	0.0447 (11)
H11	−0.2677	0.8219	0.2971	0.054*
C24	0.3265 (4)	0.5317 (2)	0.5439 (3)	0.0517 (11)
H24	0.3901	0.5662	0.5400	0.062*
C22	0.2272 (5)	0.4478 (2)	0.6510 (3)	0.0499 (11)
H22	0.2208	0.4242	0.7188	0.060*
C23	0.3208 (4)	0.4987 (3)	0.6463 (3)	0.0545 (12)
H23	0.3786	0.5107	0.7104	0.065*
O1W	0.8383 (3)	0.23234 (19)	−0.0179 (3)	0.0588 (8)
H1A	0.885 (5)	0.273 (2)	−0.030 (4)	0.088*
H1B	0.867 (5)	0.222 (3)	0.049 (3)	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.03782 (13)	0.03792 (13)	0.04067 (12)	−0.00251 (6)	0.00932 (8)	0.00471 (6)
O5	0.0479 (19)	0.0526 (17)	0.0440 (15)	0.0115 (14)	0.0139 (14)	0.0043 (13)
C7	0.034 (3)	0.048 (3)	0.044 (2)	−0.0059 (18)	0.005 (2)	0.0071 (17)
C20	0.025 (2)	0.036 (2)	0.0352 (19)	0.0043 (16)	0.0062 (17)	0.0005 (15)
O2	0.0394 (18)	0.0588 (18)	0.0450 (15)	0.0114 (15)	0.0032 (14)	0.0044 (13)
N2	0.035 (2)	0.0451 (19)	0.0393 (17)	−0.0048 (16)	0.0027 (16)	0.0004 (14)
O1	0.0461 (19)	0.0453 (17)	0.0382 (15)	−0.0017 (14)	0.0077 (13)	0.0033 (12)
C19	0.031 (2)	0.0262 (18)	0.038 (2)	0.0034 (16)	0.0068 (17)	−0.0005 (15)
C9	0.042 (2)	0.031 (2)	0.0369 (19)	−0.0055 (17)	0.0141 (19)	0.0000 (15)
C2	0.037 (3)	0.037 (2)	0.039 (2)	−0.0053 (17)	0.0064 (19)	0.0038 (15)
N1	0.039 (2)	0.0410 (19)	0.0329 (16)	−0.0028 (15)	0.0029 (15)	0.0047 (13)
O6	0.0435 (19)	0.0505 (17)	0.0480 (16)	0.0107 (14)	0.0009 (14)	−0.0065 (13)
C21	0.042 (3)	0.041 (2)	0.039 (2)	−0.0018 (19)	0.007 (2)	0.0018 (17)
C1	0.035 (3)	0.043 (2)	0.045 (2)	−0.008 (2)	0.008 (2)	0.0026 (18)
C13	0.045 (3)	0.044 (2)	0.037 (2)	−0.004 (2)	0.0056 (19)	−0.0038 (17)
C14	0.045 (3)	0.037 (2)	0.037 (2)	−0.0042 (19)	0.0129 (19)	−0.0047 (16)
C3	0.050 (3)	0.047 (2)	0.040 (2)	−0.002 (2)	0.006 (2)	0.0025 (18)
C10	0.053 (3)	0.045 (2)	0.0287 (18)	0.006 (2)	0.0087 (19)	0.0018 (16)
C12	0.037 (2)	0.033 (2)	0.043 (2)	−0.0050 (18)	0.0082 (19)	−0.0024 (16)
O4	0.059 (2)	0.0521 (17)	0.0410 (16)	0.0137 (15)	0.0124 (15)	0.0015 (13)
C18	0.039 (3)	0.040 (2)	0.047 (2)	−0.0064 (19)	0.006 (2)	−0.0003 (18)
C5	0.031 (2)	0.051 (2)	0.0372 (19)	−0.0068 (19)	0.0069 (18)	−0.0010 (17)
C16	0.060 (4)	0.056 (3)	0.044 (3)	−0.010 (2)	−0.008 (2)	−0.0073 (19)
O3	0.055 (2)	0.076 (2)	0.0473 (16)	0.0091 (17)	0.0158 (16)	0.0009 (16)
C17	0.046 (3)	0.047 (3)	0.056 (3)	−0.010 (2)	0.001 (2)	−0.004 (2)
C4	0.041 (3)	0.046 (2)	0.050 (2)	0.009 (2)	0.006 (2)	0.0039 (19)
C8	0.051 (3)	0.036 (2)	0.0320 (19)	−0.0002 (19)	0.013 (2)	0.0014 (15)
C15	0.065 (3)	0.054 (3)	0.034 (2)	−0.014 (2)	−0.001 (2)	0.0032 (18)
C6	0.042 (3)	0.059 (3)	0.039 (2)	−0.006 (2)	0.009 (2)	0.0073 (19)
C11	0.049 (3)	0.047 (3)	0.043 (2)	0.006 (2)	0.019 (2)	−0.0029 (17)
C24	0.041 (3)	0.060 (3)	0.051 (2)	−0.010 (2)	−0.003 (2)	0.000 (2)
C22	0.060 (3)	0.055 (3)	0.033 (2)	0.001 (2)	0.003 (2)	0.0090 (19)
C23	0.047 (3)	0.068 (3)	0.040 (2)	−0.002 (2)	−0.013 (2)	0.001 (2)
O1W	0.060 (2)	0.060 (2)	0.0592 (19)	0.0064 (17)	0.0169 (18)	0.0124 (16)

Geometric parameters (Å, º) top

Pb1—N1	2.463 (3)	C13—H13	0.9300
Pb1—O2	2.477 (3)	C14—H14	0.9300
Pb1—O5	2.514 (3)	C3—C4	1.370 (6)
Pb1—N2	2.563 (3)	C3—H3	0.9300
Pb1—O1	2.583 (3)	C10—C11	1.359 (6)
Pb1—O4	2.625 (3)	C10—H10	0.9300
O5—C8	1.279 (4)	C12—C11	1.386 (5)
C7—C6	1.374 (6)	O4—C8	1.254 (4)
C7—C2	1.385 (6)	C18—C17	1.363 (6)
C7—H7	0.9300	C18—H18	0.9300
C20—N2	1.346 (5)	C5—O3	1.364 (5)
C20—C21	1.378 (5)	C5—C4	1.374 (5)
C20—C19	1.484 (5)	C5—C6	1.379 (6)
O2—C1	1.252 (5)	C16—C17	1.368 (6)
N2—C24	1.332 (5)	C16—C15	1.371 (6)
O1—C1	1.271 (5)	C16—H16	0.9300
C19—N1	1.351 (5)	O3—H3A	0.8200
C19—C18	1.366 (6)	C17—H17	0.9300
C9—C14	1.397 (5)	C4—H4	0.9300
C9—C10	1.402 (5)	C15—H15	0.9300
C9—C8	1.482 (6)	C6—H6	0.9300
C2—C3	1.387 (6)	C11—H11	0.9300
C2—C1	1.501 (6)	C24—C23	1.374 (6)
N1—C15	1.337 (5)	C24—H24	0.9300
O6—C12	1.341 (5)	C22—C23	1.368 (6)
O6—H6A	0.8200	C22—H22	0.9300
C21—C22	1.379 (6)	C23—H23	0.9300
C21—H21	0.9300	O1W—H1A	0.90 (3)
C13—C14	1.364 (6)	O1W—H1B	0.83 (3)
C13—C12	1.405 (5)

N1—Pb1—O2	77.93 (10)	C13—C14—H14	119.3
N1—Pb1—O5	76.79 (10)	C9—C14—H14	119.3
O2—Pb1—O5	83.20 (9)	C4—C3—C2	120.7 (4)
N1—Pb1—N2	64.57 (10)	C4—C3—H3	119.7
O2—Pb1—N2	123.60 (11)	C2—C3—H3	119.7
O5—Pb1—N2	123.38 (10)	C11—C10—C9	120.3 (4)
N1—Pb1—O1	81.27 (11)	C11—C10—H10	119.9
O2—Pb1—O1	51.53 (9)	C9—C10—H10	119.9
O5—Pb1—O1	132.96 (8)	O6—C12—C11	123.3 (3)
N2—Pb1—O1	81.23 (9)	O6—C12—C13	118.6 (3)
N1—Pb1—O4	75.54 (10)	C11—C12—C13	118.2 (4)
O2—Pb1—O4	130.87 (9)	C8—O4—Pb1	91.5 (2)
O5—Pb1—O4	50.89 (8)	C17—C18—C19	120.6 (4)
N2—Pb1—O4	79.42 (10)	C17—C18—H18	119.7
O1—Pb1—O4	154.53 (9)	C19—C18—H18	119.7
C8—O5—Pb1	96.1 (2)	O3—C5—C4	122.9 (4)
C6—C7—C2	120.3 (4)	O3—C5—C6	117.6 (3)
C6—C7—H7	119.9	C4—C5—C6	119.5 (4)
C2—C7—H7	119.9	C17—C16—C15	117.7 (4)
N2—C20—C21	121.2 (4)	C17—C16—H16	121.1
N2—C20—C19	116.3 (3)	C15—C16—H16	121.1
C21—C20—C19	122.5 (4)	C5—O3—H3A	109.5
C1—O2—Pb1	95.8 (2)	C18—C17—C16	119.4 (4)
C24—N2—C20	118.4 (3)	C18—C17—H17	120.3
C24—N2—Pb1	122.0 (3)	C16—C17—H17	120.3
C20—N2—Pb1	119.6 (2)	C3—C4—C5	120.3 (4)
C1—O1—Pb1	90.4 (2)	C3—C4—H4	119.8
N1—C19—C18	120.6 (4)	C5—C4—H4	119.8
N1—C19—C20	116.6 (3)	O4—C8—O5	121.5 (4)
C18—C19—C20	122.7 (3)	O4—C8—C9	119.8 (3)
C14—C9—C10	118.1 (4)	O5—C8—C9	118.7 (3)
C14—C9—C8	122.0 (3)	N1—C15—C16	123.6 (4)
C10—C9—C8	119.9 (3)	N1—C15—H15	118.2
C7—C2—C3	118.7 (4)	C16—C15—H15	118.2
C7—C2—C1	120.2 (4)	C7—C6—C5	120.5 (4)
C3—C2—C1	121.1 (4)	C7—C6—H6	119.8
C15—N1—C19	118.1 (3)	C5—C6—H6	119.8
C15—N1—Pb1	119.0 (3)	C10—C11—C12	121.8 (4)
C19—N1—Pb1	122.8 (2)	C10—C11—H11	119.1
C12—O6—H6A	109.5	C12—C11—H11	119.1
C20—C21—C22	119.2 (4)	N2—C24—C23	123.5 (4)
C20—C21—H21	120.4	N2—C24—H24	118.2
C22—C21—H21	120.4	C23—C24—H24	118.2
O2—C1—O1	121.6 (4)	C23—C22—C21	119.9 (4)
O2—C1—C2	119.9 (4)	C23—C22—H22	120.1
O1—C1—C2	118.5 (4)	C21—C22—H22	120.1
C14—C13—C12	120.2 (4)	C22—C23—C24	117.8 (4)
C14—C13—H13	119.9	C22—C23—H23	121.1
C12—C13—H13	119.9	C24—C23—H23	121.1
C13—C14—C9	121.3 (4)	H1A—O1W—H1B	102 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1ⁱ	0.82	1.90	2.671 (4)	157
O3—H3A···O1W	0.82	1.89	2.695 (5)	166
O1W—H1A···O5ⁱⁱ	0.90 (3)	2.04 (3)	2.849 (4)	148 (5)
O1W—H1B···O4ⁱⁱⁱ	0.83 (3)	2.00 (3)	2.789 (4)	158 (5)

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

Experimental details

Crystal data
Chemical formula	[Pb(C₇H₅O₃)₂(C₁₀H₈N₂)]·H₂O
M_r	655.61
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	10.9483 (4), 17.5194 (6), 12.0479 (4)
β (°)	100.334 (2)
V (Å³)	2273.39 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.47
Crystal size (mm)	0.35 × 0.26 × 0.21

Data collection
Diffractometer	Bruker APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2007)
T_min, T_max	0.180, 0.303
No. of measured, independent and observed [I > σ(I)] reflections	18618, 4067, 3579
R_int	0.037
(sin θ/λ)_max (Å⁻¹)	0.598

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.025, 0.072, 1.01
No. of reflections	4067
No. of parameters	315
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.05, −0.61

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O1ⁱ	0.82	1.90	2.671 (4)	156.8
O3—H3A···O1W	0.82	1.89	2.695 (5)	166.4
O1W—H1A···O5ⁱⁱ	0.90 (3)	2.04 (3)	2.849 (4)	148 (5)
O1W—H1B···O4ⁱⁱⁱ	0.83 (3)	2.00 (3)	2.789 (4)	158 (5)

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

Acknowledgements

The authors acknowledge the Doctoral Foundation of Henan Polytechnic University (B2008–58 648265).

References

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