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Acta Cryst. (2007). E63, m3042-m3043    [ doi:10.1107/S1600536807057868 ]

Bis([mu]-4-hydroxybenzoato-[kappa]2O:O')bis[(2,9-dimethyl-1,10-phenanthroline-[kappa]2N,N')(4-hydroxybenzoato-[kappa]2O,O')lead(II)]

P.-Z. Zhao, X.-P. Xuan and Q.-H. Tang

Abstract top

In the centrosymmetric binuclear title complex, [Pb2(C7H5O3)4(C14H12N2)2], each PbII ion is coordinated by two N atoms from a 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand and four O atoms from three 4-hydroxybenzoate anions in a distorted octahedral environment. The 4-hydroxybenzoate groups coordinate to each PbII atom in two different ways. Two 4-hydroxybenzoate ions behave as chelating ligands to a single Pb atom, and the other two form bridges between the two Pb atoms, forming a centrosymmetric eight-membered ring in the binuclear structure. Molecules are linked into a two-dimensional framework by O-H...O hydrogen bonds. The packing is further stabilized by [pi]-[pi] interactions between the dmphen rings of neighboring molecules, with a distance of 3.327 Å between the planes of the dmphen ligands.

Comment top

The coordination chemistry of lead(II) with N and O donor ligands has been investigated in the past decade and is frequently discussed as lead is an environmental pollutant with severe toxic effects (Shimoni-Livny et al., 2003). Because of its electronic configuration and size, Pb(II) exhibits various coordination numbers and geometries. A number of lead(II) complexes with different donor ligands have been synthesized and studied by X-ray crystallography (Mahjoub & Morsali, 2002; Morsali et al., 2003; Li et al., 2005; Zhang et al., 2005; Xuan & Zhao, 2007). The title complex, (I), was recently obtained from the reaction of lead acetate, sodium 4-hydroxybenzoate and dmphen in an ethanol/water mixture, and its crystal structure is reported here.

Each PbII ion is six-coordinated by the two N atoms from a dmphen ligand, and four carbonyl O atoms from three 4-hydroxybenzoate ligands (Fig.1). The four Pb—O bond lengths are significantly different, as are the two Pb—N bond lengths and each PbII cation lies at the center of a distorted octahedron. The Pb—O—C—O bridging interaction, forms a centrosymmetric eight-membered Pb2O4C2 ring with a Pb···Pb distance of 4.2639 (3) Å.

In the crystal structure, molecules are linked into a two dimensional framework by intermolecular O—H···O hydrogen (Fig.2). The packing is further stabilized by π-π interactions between the dmphen rings of neighboring molecules. The distance between the parallel planes (N1/C1—C10/ N2/C11/C12) [symmetry code: −x + 1, −y + 2, −z + 1] of neighboring molecules is 3.3272 Å. This combination of hydrogen bonds and π-π stacking interactions builds a three-dimensional network architecture.

Related literature top

For the background to lead coordination chemistry, see: Shimoni-Livny et al. (1998). For related structures, see: Li et al. (2005); Mahjoub & Morsali (2002); Morsali, Mahjoub et al. (2003); Morsali, Payeghader et al. (2003); Xuan & Zhao (2007); Zhang & Lu (2005).

Experimental top

4-hydroxybenzoic acid (0.0691 g, 0.5 mmol) and NaOH (0.0182 g, 0.5 > mmol) were dissolved in distilled water (10 ml) and Pb(CH3COOH)2.3H2O (0.1897 g, 0.5 mmol) was added. This solution was added to a solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C14H12N2.0.5H2O, 0.1090 g, 0.5 mmol) in ethanol (10 ml). The mixture was stirred at 323 K and then refluxed for 4 h, cooled to room temperature and filtered. Bright colorless single crystals of (I) appeared over a period of four days by slow evaporation at room temperature.

Refinement top

Methyl H and hydroxy H atoms were placed in calculated positions,with C—H = 0.96 and O—H = 0.82 Å, and refined with free torsion angles to fit the electron density; Uiso(H) = 1.5Ueq(carrier). Other H atoms were placed in calculated positions, with C—H=0.93 Å, and refined using the riding-model approximation with Uiso(H) = 1.2Ueq(C).

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
[Figure 1] Fig. 1. The molecular structure of the title complex(I), with atom labels and 30% probability displacement ellipsoids. [Symmetry codes:(A)-x + 1, −y + 2, −z + 1]
[Figure 2] Fig. 2. The hydrogen-bonding motifs in the crystal structure of (I). Dashed lines indicate the hydrogen bonds.
[Figure 3] Fig. 3. π-π interactions between the dmphen rings of neighboring molecules in the crystal structure of (I).
Bis(µ-4-hydroxybenzoato-κ2O:O')bis[(2,9-dimethyl-1,10- phenanthroline-κ2N,N')(4-hydroxybenzoato- κ2O,O')lead(II)] top
Crystal data top
[Pb2(C7H5O3)4(C14H12N2)2]F000 = 1336
Mr = 1379.35Dx = 1.793 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8418 reflections
a = 11.0539 (9) Åθ = 2.6–28.1º
b = 20.9060 (16) ŵ = 6.65 mm−1
c = 11.2905 (9) ÅT = 293 (2) K
β = 101.667 (1)ºBlock, colorless
V = 2555.2 (4) Å30.26 × 0.21 × 0.17 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		4760 independent reflections
Radiation source: fine-focus sealed tube4180 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 293(2) Kθmax = 25.5º
φ and ω scansθmin = 2.6º
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −13→13
Tmin = 0.277, Tmax = 0.396k = −25→25
17442 measured reflectionsl = −13→13
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.018H-atom parameters constrained
wR(F2) = 0.042  w = 1/[σ2(Fo2) + (0.0193P)2 + 1.4405P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.008
4760 reflectionsΔρmax = 0.49 e Å−3
338 parametersΔρmin = −0.56 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Pb2(C7H5O3)4(C14H12N2)2]V = 2555.2 (4) Å3
Mr = 1379.35Z = 2
Monoclinic, P21/cMo Kα
a = 11.0539 (9) ŵ = 6.65 mm−1
b = 20.9060 (16) ÅT = 293 (2) K
c = 11.2905 (9) Å0.26 × 0.21 × 0.17 mm
β = 101.667 (1)º
Data collection top
Bruker SMART CCD area-detector
diffractometer		4760 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		4180 reflections with I > 2σ(I)
Tmin = 0.277, Tmax = 0.396Rint = 0.021
17442 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.018338 parameters
wR(F2) = 0.042H-atom parameters constrained
S = 1.03Δρmax = 0.49 e Å−3
4760 reflectionsΔρmin = −0.56 e Å−3
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
xyzUiso*/Ueq
Pb10.348130 (9)1.006948 (4)0.350408 (8)0.03245 (3)
O10.20574 (17)1.10887 (8)0.32230 (17)0.0458 (5)
O20.32361 (17)1.09044 (8)0.19066 (16)0.0407 (4)
O30.1365 (2)1.37068 (9)0.03074 (19)0.0613 (6)
H30.16261.3744−0.03200.092*
O40.3130 (2)0.89345 (9)0.41329 (18)0.0572 (6)
O50.4729 (3)0.90298 (13)0.5611 (3)0.1133 (11)
O60.17088 (18)0.68062 (9)0.75700 (18)0.0509 (5)
H60.22280.66340.80950.076*
N10.16493 (18)0.96424 (9)0.20827 (18)0.0304 (5)
N20.40432 (19)0.95256 (10)0.17560 (19)0.0370 (5)
C10.0516 (2)0.96366 (12)0.2313 (2)0.0381 (6)
C2−0.0479 (3)0.94005 (15)0.1465 (3)0.0536 (8)
H2−0.12650.93980.16420.064*
C3−0.0309 (3)0.91738 (15)0.0379 (3)0.0554 (8)
H3A−0.09820.9029−0.01910.066*
C40.0881 (3)0.91577 (13)0.0120 (2)0.0427 (7)
C50.1137 (3)0.89075 (15)−0.0979 (3)0.0563 (9)
H50.04900.8762−0.15780.068*
C60.2297 (3)0.88786 (15)−0.1160 (3)0.0571 (9)
H6A0.24410.8722−0.18900.068*
C70.3317 (3)0.90852 (13)−0.0251 (2)0.0464 (7)
C80.4554 (3)0.90407 (16)−0.0384 (3)0.0640 (9)
H80.47400.8895−0.11040.077*
C90.5475 (3)0.92142 (18)0.0556 (3)0.0691 (10)
H90.62940.91740.04820.083*
C100.5203 (3)0.94512 (16)0.1627 (3)0.0547 (8)
C110.3103 (2)0.93440 (11)0.0837 (2)0.0349 (6)
C120.1850 (2)0.93923 (11)0.1022 (2)0.0334 (6)
C130.0322 (3)0.98732 (14)0.3514 (3)0.0518 (8)
H13A0.10850.98460.40960.078*
H13B−0.02920.96150.37770.078*
H13C0.00501.03100.34390.078*
C140.6209 (3)0.9627 (2)0.2687 (3)0.0871 (13)
H14A0.61861.00790.28300.131*
H14B0.69970.95140.25160.131*
H14C0.60850.94010.33930.131*
C150.2559 (2)1.12721 (11)0.2362 (2)0.0337 (6)
C160.2293 (2)1.19281 (11)0.1859 (2)0.0327 (6)
C170.1416 (2)1.23151 (12)0.2226 (2)0.0398 (7)
H170.10181.21710.28270.048*
C180.1123 (3)1.29088 (13)0.1716 (3)0.0471 (7)
H180.05331.31610.19730.057*
C190.1709 (3)1.31292 (12)0.0819 (2)0.0416 (7)
C200.2618 (3)1.27543 (13)0.0469 (3)0.0455 (7)
H200.30391.2905−0.01100.055*
C210.2892 (2)1.21626 (12)0.0979 (2)0.0406 (7)
H210.34911.19130.07300.049*
C220.3756 (3)0.87749 (13)0.5160 (3)0.0523 (8)
C230.3240 (2)0.82471 (12)0.5819 (2)0.0390 (6)
C240.3987 (3)0.78902 (14)0.6709 (3)0.0503 (8)
H240.48280.79790.69090.060*
C250.3509 (3)0.74027 (13)0.7308 (3)0.0495 (8)
H250.40270.71640.78970.059*
C260.2253 (3)0.72726 (12)0.7024 (2)0.0393 (6)
C270.1495 (3)0.76263 (13)0.6135 (3)0.0450 (7)
H270.06530.75390.59370.054*
C280.1986 (3)0.81074 (13)0.5542 (2)0.0439 (7)
H280.14680.83420.49460.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.03696 (5)0.03192 (5)0.02734 (5)−0.00627 (4)0.00379 (4)−0.00068 (4)
O10.0582 (12)0.0384 (10)0.0471 (11)−0.0025 (9)0.0258 (10)0.0015 (8)
O20.0481 (11)0.0396 (9)0.0362 (10)0.0098 (8)0.0129 (9)0.0037 (8)
O30.0839 (15)0.0490 (11)0.0582 (13)0.0280 (11)0.0313 (12)0.0177 (10)
O40.0853 (15)0.0409 (11)0.0417 (12)−0.0202 (10)0.0037 (11)0.0067 (9)
O50.0940 (18)0.1016 (19)0.119 (2)−0.0676 (16)−0.0374 (17)0.0441 (17)
O60.0571 (12)0.0458 (11)0.0524 (12)0.0004 (9)0.0171 (10)0.0133 (9)
N10.0313 (11)0.0301 (10)0.0303 (11)−0.0027 (8)0.0073 (9)−0.0012 (8)
N20.0334 (11)0.0411 (12)0.0372 (12)0.0016 (9)0.0088 (10)−0.0015 (9)
C10.0340 (14)0.0372 (14)0.0449 (16)−0.0034 (11)0.0121 (12)−0.0010 (11)
C20.0318 (15)0.0667 (19)0.063 (2)−0.0111 (14)0.0100 (14)−0.0072 (16)
C30.0367 (16)0.068 (2)0.0544 (19)−0.0132 (14)−0.0071 (14)−0.0123 (16)
C40.0445 (16)0.0451 (15)0.0353 (15)−0.0074 (13)0.0004 (13)−0.0056 (12)
C50.063 (2)0.0629 (19)0.0377 (17)−0.0111 (16)−0.0027 (15)−0.0139 (14)
C60.076 (2)0.0606 (19)0.0351 (16)−0.0031 (17)0.0124 (16)−0.0158 (14)
C70.0543 (17)0.0501 (16)0.0375 (16)0.0035 (13)0.0159 (14)−0.0070 (12)
C80.065 (2)0.076 (2)0.057 (2)0.0112 (18)0.0280 (17)−0.0155 (17)
C90.0449 (17)0.095 (3)0.073 (2)0.0104 (18)0.0258 (17)−0.017 (2)
C100.0366 (16)0.071 (2)0.057 (2)0.0050 (15)0.0116 (14)−0.0066 (16)
C110.0398 (14)0.0318 (12)0.0337 (14)0.0011 (11)0.0086 (12)−0.0012 (10)
C120.0376 (14)0.0294 (12)0.0324 (14)−0.0006 (10)0.0052 (11)−0.0025 (10)
C130.0436 (15)0.0598 (18)0.0589 (19)−0.0091 (14)0.0262 (14)−0.0120 (14)
C140.0338 (18)0.147 (4)0.079 (3)0.002 (2)0.0060 (18)−0.025 (3)
C150.0351 (14)0.0349 (13)0.0299 (14)−0.0031 (11)0.0039 (11)−0.0029 (10)
C160.0318 (13)0.0343 (13)0.0310 (14)−0.0007 (10)0.0041 (11)−0.0017 (10)
C170.0413 (15)0.0450 (15)0.0358 (15)0.0022 (12)0.0141 (12)0.0016 (11)
C180.0500 (16)0.0501 (16)0.0451 (17)0.0173 (13)0.0190 (14)0.0022 (13)
C190.0489 (16)0.0375 (14)0.0390 (16)0.0085 (12)0.0104 (13)0.0035 (11)
C200.0471 (16)0.0473 (15)0.0470 (17)0.0077 (13)0.0211 (13)0.0105 (12)
C210.0405 (15)0.0437 (14)0.0402 (16)0.0109 (12)0.0146 (13)0.0035 (12)
C220.061 (2)0.0396 (15)0.0538 (19)−0.0162 (14)0.0057 (16)−0.0010 (13)
C230.0444 (15)0.0355 (13)0.0347 (15)−0.0069 (12)0.0020 (12)−0.0004 (11)
C240.0398 (16)0.0552 (17)0.0509 (19)−0.0105 (13)−0.0027 (14)0.0063 (14)
C250.0502 (17)0.0466 (16)0.0474 (18)0.0056 (13)−0.0006 (14)0.0118 (13)
C260.0518 (16)0.0323 (13)0.0361 (15)0.0008 (12)0.0138 (13)0.0017 (11)
C270.0411 (15)0.0503 (16)0.0440 (17)−0.0035 (13)0.0099 (13)0.0066 (13)
C280.0457 (16)0.0446 (15)0.0385 (16)0.0038 (13)0.0017 (13)0.0074 (12)
Geometric parameters (Å, °) top
Pb1—N22.464 (2)C8—C91.363 (5)
Pb1—N12.4818 (19)C8—H80.9300
Pb1—O22.4851 (17)C9—C101.394 (4)
Pb1—O42.5291 (18)C9—H90.9300
Pb1—O12.6298 (18)C10—C141.506 (4)
Pb1—O5i2.767 (2)C11—C121.445 (3)
Pb1—C152.914 (2)C13—H13A0.9600
O1—C151.271 (3)C13—H13B0.9600
O2—C151.254 (3)C13—H13C0.9600
O3—C191.359 (3)C14—H14A0.9600
O3—H30.8200C14—H14B0.9600
O4—C221.269 (3)C14—H14C0.9600
O5—C221.216 (4)C15—C161.491 (3)
O5—Pb1i2.767 (2)C16—C171.389 (3)
O6—C261.357 (3)C16—C211.390 (3)
O6—H60.8200C17—C181.379 (4)
N1—C11.330 (3)C17—H170.9300
N1—C121.365 (3)C18—C191.386 (4)
N2—C101.329 (3)C18—H180.9300
N2—C111.365 (3)C19—C201.393 (4)
C1—C21.394 (4)C20—C211.372 (4)
C1—C131.499 (4)C20—H200.9300
C2—C31.363 (4)C21—H210.9300
C2—H20.9300C22—C231.506 (4)
C3—C41.405 (4)C23—C241.383 (4)
C3—H3A0.9300C23—C281.389 (4)
C4—C121.409 (3)C24—C251.386 (4)
C4—C51.427 (4)C24—H240.9300
C5—C61.340 (4)C25—C261.387 (4)
C5—H50.9300C25—H250.9300
C6—C71.430 (4)C26—C271.385 (4)
C6—H6A0.9300C27—C281.379 (4)
C7—C111.406 (4)C27—H270.9300
C7—C81.408 (4)C28—H280.9300
N2—Pb1—N167.72 (7)N2—C11—C7122.3 (2)
N2—Pb1—O275.58 (6)N2—C11—C12118.4 (2)
N1—Pb1—O280.12 (6)C7—C11—C12119.3 (2)
N2—Pb1—O482.52 (7)N1—C12—C4122.2 (2)
N1—Pb1—O472.09 (7)N1—C12—C11119.0 (2)
O2—Pb1—O4149.58 (6)C4—C12—C11118.8 (2)
N2—Pb1—O1121.26 (6)C1—C13—H13A109.5
N1—Pb1—O179.82 (6)C1—C13—H13B109.5
O2—Pb1—O150.84 (6)H13A—C13—H13B109.5
O4—Pb1—O1132.21 (7)C1—C13—H13C109.5
N2—Pb1—O5i109.00 (9)H13A—C13—H13C109.5
N1—Pb1—O5i155.30 (7)H13B—C13—H13C109.5
O2—Pb1—O5i75.47 (7)C10—C14—H14A109.5
O4—Pb1—O5i132.55 (7)C10—C14—H14B109.5
O1—Pb1—O5i81.89 (8)H14A—C14—H14B109.5
N2—Pb1—C1599.56 (7)C10—C14—H14C109.5
N1—Pb1—C1581.81 (6)H14A—C14—H14C109.5
O2—Pb1—C1525.29 (6)H14B—C14—H14C109.5
O4—Pb1—C15150.90 (7)O2—C15—O1121.2 (2)
O1—Pb1—C1525.87 (6)O2—C15—C16119.7 (2)
O5i—Pb1—C1574.53 (7)O1—C15—C16119.1 (2)
C15—O1—Pb189.65 (14)O2—C15—Pb157.86 (12)
C15—O2—Pb196.86 (15)O1—C15—Pb164.48 (13)
C19—O3—H3109.5C16—C15—Pb1170.63 (17)
C22—O4—Pb1114.65 (17)C17—C16—C21118.0 (2)
C22—O5—Pb1i163.1 (3)C17—C16—C15121.2 (2)
C26—O6—H6109.5C21—C16—C15120.8 (2)
C1—N1—C12119.6 (2)C18—C17—C16121.2 (3)
C1—N1—Pb1123.69 (16)C18—C17—H17119.4
C12—N1—Pb1116.66 (15)C16—C17—H17119.4
C10—N2—C11119.1 (2)C17—C18—C19120.0 (3)
C10—N2—Pb1123.19 (18)C17—C18—H18120.0
C11—N2—Pb1117.42 (16)C19—C18—H18120.0
N1—C1—C2120.8 (3)O3—C19—C18118.3 (2)
N1—C1—C13119.1 (2)O3—C19—C20122.4 (3)
C2—C1—C13120.1 (2)C18—C19—C20119.4 (2)
C3—C2—C1120.5 (3)C21—C20—C19119.9 (3)
C3—C2—H2119.8C21—C20—H20120.0
C1—C2—H2119.8C19—C20—H20120.0
C2—C3—C4120.1 (3)C20—C21—C16121.4 (2)
C2—C3—H3A119.9C20—C21—H21119.3
C4—C3—H3A119.9C16—C21—H21119.3
C3—C4—C12116.6 (3)O5—C22—O4122.7 (3)
C3—C4—C5123.3 (3)O5—C22—C23120.3 (3)
C12—C4—C5120.1 (3)O4—C22—C23117.0 (3)
C6—C5—C4120.9 (3)C24—C23—C28118.2 (2)
C6—C5—H5119.5C24—C23—C22121.6 (3)
C4—C5—H5119.5C28—C23—C22120.2 (2)
C5—C6—C7121.1 (3)C23—C24—C25121.4 (3)
C5—C6—H6A119.4C23—C24—H24119.3
C7—C6—H6A119.4C25—C24—H24119.3
C11—C7—C8117.2 (3)C24—C25—C26119.6 (3)
C11—C7—C6119.7 (3)C24—C25—H25120.2
C8—C7—C6123.0 (3)C26—C25—H25120.2
C9—C8—C7119.2 (3)O6—C26—C27117.0 (2)
C9—C8—H8120.4O6—C26—C25123.4 (2)
C7—C8—H8120.4C27—C26—C25119.6 (2)
C8—C9—C10120.8 (3)C28—C27—C26120.1 (3)
C8—C9—H9119.6C28—C27—H27119.9
C10—C9—H9119.6C26—C27—H27119.9
N2—C10—C9121.2 (3)C27—C28—C23121.1 (3)
N2—C10—C14117.2 (3)C27—C28—H28119.4
C9—C10—C14121.5 (3)C23—C28—H28119.4
N2—Pb1—O1—C15−36.24 (16)C10—N2—C11—C12176.3 (2)
N1—Pb1—O1—C15−92.21 (15)Pb1—N2—C11—C12−9.2 (3)
O2—Pb1—O1—C15−6.72 (13)C8—C7—C11—N2−2.4 (4)
O4—Pb1—O1—C15−146.43 (14)C6—C7—C11—N2177.3 (3)
O5i—Pb1—O1—C1571.10 (16)C8—C7—C11—C12−179.2 (3)
N2—Pb1—O2—C15161.08 (16)C6—C7—C11—C120.5 (4)
N1—Pb1—O2—C1591.73 (15)C1—N1—C12—C43.7 (4)
O4—Pb1—O2—C15115.79 (18)Pb1—N1—C12—C4−177.46 (19)
O1—Pb1—O2—C156.86 (14)C1—N1—C12—C11−173.9 (2)
O5i—Pb1—O2—C15−84.47 (16)Pb1—N1—C12—C114.9 (3)
N2—Pb1—O4—C22122.6 (2)C3—C4—C12—N1−2.0 (4)
N1—Pb1—O4—C22−168.4 (2)C5—C4—C12—N1179.3 (2)
O2—Pb1—O4—C22166.60 (19)C3—C4—C12—C11175.6 (2)
O1—Pb1—O4—C22−111.4 (2)C5—C4—C12—C11−3.1 (4)
O5i—Pb1—O4—C2213.7 (3)N2—C11—C12—N12.8 (3)
C15—Pb1—O4—C22−141.1 (2)C7—C11—C12—N1179.8 (2)
N2—Pb1—N1—C1172.1 (2)N2—C11—C12—C4−174.9 (2)
O2—Pb1—N1—C1−109.56 (19)C7—C11—C12—C42.1 (4)
O4—Pb1—N1—C182.97 (19)Pb1—O2—C15—O1−12.9 (3)
O1—Pb1—N1—C1−57.88 (19)Pb1—O2—C15—C16169.45 (19)
O5i—Pb1—N1—C1−100.7 (3)Pb1—O1—C15—O212.1 (2)
C15—Pb1—N1—C1−84.01 (19)Pb1—O1—C15—C16−170.2 (2)
N2—Pb1—N1—C12−6.72 (15)N2—Pb1—C15—O2−18.57 (15)
O2—Pb1—N1—C1271.63 (16)N1—Pb1—C15—O2−84.19 (15)
O4—Pb1—N1—C12−95.83 (17)O4—Pb1—C15—O2−110.36 (18)
O1—Pb1—N1—C12123.32 (17)O1—Pb1—C15—O2−167.7 (2)
O5i—Pb1—N1—C1280.5 (3)O5i—Pb1—C15—O288.64 (16)
C15—Pb1—N1—C1297.19 (17)N2—Pb1—C15—O1149.17 (14)
N1—Pb1—N2—C10−177.5 (2)N1—Pb1—C15—O183.54 (14)
O2—Pb1—N2—C1097.4 (2)O2—Pb1—C15—O1167.7 (2)
O4—Pb1—N2—C10−103.9 (2)O4—Pb1—C15—O157.4 (2)
O1—Pb1—N2—C10120.7 (2)O5i—Pb1—C15—O1−103.62 (16)
O5i—Pb1—N2—C1028.7 (2)O2—C15—C16—C17171.0 (2)
C15—Pb1—N2—C10105.5 (2)O1—C15—C16—C17−6.7 (4)
N1—Pb1—N2—C118.24 (16)O2—C15—C16—C21−7.0 (4)
O2—Pb1—N2—C11−76.82 (17)O1—C15—C16—C21175.3 (2)
O4—Pb1—N2—C1181.90 (18)C21—C16—C17—C181.5 (4)
O1—Pb1—N2—C11−53.58 (19)C15—C16—C17—C18−176.6 (2)
O5i—Pb1—N2—C11−145.56 (17)C16—C17—C18—C190.0 (4)
C15—Pb1—N2—C11−68.75 (18)C17—C18—C19—O3177.7 (3)
C12—N1—C1—C2−2.5 (4)C17—C18—C19—C20−1.9 (4)
Pb1—N1—C1—C2178.8 (2)O3—C19—C20—C21−177.2 (3)
C12—N1—C1—C13176.0 (2)C18—C19—C20—C212.4 (4)
Pb1—N1—C1—C13−2.7 (3)C19—C20—C21—C16−1.0 (4)
N1—C1—C2—C3−0.3 (4)C17—C16—C21—C20−0.9 (4)
C13—C1—C2—C3−178.8 (3)C15—C16—C21—C20177.1 (2)
C1—C2—C3—C42.0 (5)Pb1i—O5—C22—O452.9 (11)
C2—C3—C4—C12−0.8 (4)Pb1i—O5—C22—C23−127.0 (8)
C2—C3—C4—C5177.8 (3)Pb1—O4—C22—O5−25.3 (4)
C3—C4—C5—C6−177.1 (3)Pb1—O4—C22—C23154.6 (2)
C12—C4—C5—C61.4 (5)O5—C22—C23—C24−22.2 (5)
C4—C5—C6—C71.3 (5)O4—C22—C23—C24157.9 (3)
C5—C6—C7—C11−2.2 (5)O5—C22—C23—C28157.7 (3)
C5—C6—C7—C8177.5 (3)O4—C22—C23—C28−22.2 (4)
C11—C7—C8—C93.5 (5)C28—C23—C24—C250.4 (4)
C6—C7—C8—C9−176.2 (3)C22—C23—C24—C25−179.6 (3)
C7—C8—C9—C10−1.9 (5)C23—C24—C25—C26−0.8 (5)
C11—N2—C10—C92.4 (4)C24—C25—C26—O6−179.7 (3)
Pb1—N2—C10—C9−171.7 (2)C24—C25—C26—C270.8 (4)
C11—N2—C10—C14−177.0 (3)O6—C26—C27—C28−179.9 (3)
Pb1—N2—C10—C148.9 (4)C25—C26—C27—C28−0.4 (4)
C8—C9—C10—N2−1.2 (5)C26—C27—C28—C230.0 (4)
C8—C9—C10—C14178.2 (4)C24—C23—C28—C270.0 (4)
C10—N2—C11—C7−0.6 (4)C22—C23—C28—C27−180.0 (3)
Pb1—N2—C11—C7173.90 (19)
Symmetry codes: (i) −x+1, −y+2, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1ii0.821.842.652 (3)172
O6—H6···O4iii0.821.822.619 (3)165
Symmetry codes: (ii) x, −y+5/2, z−1/2; (iii) x, −y+3/2, z+1/2.
Table 1
Selected geometric parameters (Å) top
Pb1—N22.464 (2)Pb1—O42.5291 (18)
Pb1—N12.4818 (19)Pb1—O12.6298 (18)
Pb1—O22.4851 (17)Pb1—O5i2.767 (2)
Symmetry codes: (i) −x+1, −y+2, −z+1.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O3—H3···O1ii0.821.842.652 (3)172
O6—H6···O4iii0.821.822.619 (3)165
Symmetry codes: (ii) x, −y+5/2, z−1/2; (iii) x, −y+3/2, z+1/2.
Acknowledgements top

Financial support from the Science Fund of Henan Province for Distinguished Young Scholars (No. 07410051005) is gratefully acknowledged.

references
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