PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): m1583–m1584.
Published online 2010 November 17. doi:  10.1107/S1600536810046489
PMCID: PMC3011706

Bis(benzoato-κ2 O,O′)(2,2′-bipyridine-κ2 N,N′)lead(II) benzoic acid monosolvate

Abstract

The reaction of lead acetate, benzoic acid and 2,2′-bipyridine (bipy) in aqueous solution yielded the title complex, [Pb(C7H5O2)2(C10H8N2)]·C7H6O2. The asymmetric unit contains two independent complex mol­ecules as well as two independent benzoic acid solvent mol­ecules, one of which is disordered over two positions with almost equal occupancies [0.504 (5) and 0.496 (5)]. The two complex mol­ecules have similar configurations with the hexa­coordinated environment of the PbII atom formed by four carboxyl­ate O atoms of two chelate benzoate ligands and two N atoms of the bipy ligand. The Pb—O bonds involving one of the benzoate ligands are almost coplanar with Pb—N bonds to the bipy ligand [dihedral angles of 12.67 (11) and 14.73 (11)°] ; if the second benzoate ligand is treated as one coordination site, the overall coordination may be represented as a distorted pseudo-square pyramid. Weak inter­molecular Pb(...)O inter­actions [3.046 (3) and 3.359 (3) Å] link each of the complex mol­ecules into two symmetry-independent centrosymmetric dimers. Hydrogen bonds involving the carboxyl H atoms of solvent benzoic acid mol­ecules and metal-coordinated carboxyl­ate O atoms link complex mol­ecules and benzoic acid solvent mol­ecules into insular aggregates.

Related literature

For potential applications of Pb(II) complexes, see: Fan & Zhu (2006 [triangle]); Hamilton et al. (2004 [triangle]); Alvarado et al. (2005 [triangle]). For the use of aromatic carboxyl­ates and 2,2′-bipyridine-type ligands in the preparation of metal complexes, see: Wang et al. (2006 [triangle]); Masaoka et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-m1583-scheme1.jpg

Experimental

Crystal data

  • [Pb(C7H5O2)2(C10H8N2)]·C7H6O2
  • M r = 727.71
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-m1583-efi1.jpg
  • a = 9.6298 (2) Å
  • b = 10.4264 (2) Å
  • c = 28.7365 (5) Å
  • α = 84.843 (1)°
  • β = 88.128 (1)°
  • γ = 72.619 (1)°
  • V = 2742.32 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 6.2 mm−1
  • T = 296 K
  • 0.24 × 0.19 × 0.15 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2007 [triangle]) T min = 0.253, T max = 0.395
  • 49796 measured reflections
  • 14302 independent reflections
  • 10344 reflections with I > 2σ(I)
  • R int = 0.039

Refinement

  • R[F 2 > 2σ(F 2)] = 0.035
  • wR(F 2) = 0.081
  • S = 1.01
  • 14302 reflections
  • 773 parameters
  • H-atom parameters constrained
  • Δρmax = 1.17 e Å−3
  • Δρmin = −1.13 e Å−3

Data collection: APEX2 (Bruker, 2007 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810046489/ya2132sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810046489/ya2132Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

Complexes containing Pb(II) ion have recently attracted considerable interest not only because of the variety of their architectures, but also because of their potential applications, especially in environmental protection and in systems with different biological properties (Fan & Zhu, 2006; Hamilton et al., 2004; Alvarado et al., 2005). As an important family of bidentate O-donor ligands, aromatic carboxylates have been extensively employed in the preparation of metal complexes of various structural topologies (Wang et al., 2006; Masaoka et al., 2001).

The asymmetric unit of the crystal of the title complex, [Pb(C7H5O2)2(C10H8N2)].(C7H6O2), contains two molecules of complex, as well as two independent benzoic solvate molecules (Fig.1), one of which is disordered over two positions with almost equal occupancies. Each PbII atom is hexacoordinated and chelated by four carboxylate O atoms from two benzoic acid and two N atoms from 2,2'-bipyridine ligand. In both complex molecules the O atoms of one of the carboxylate ligands (O3 and O4 in the first molecule; O7 and O8 in the second molecule) are almost coplanar with the N atoms of the bipy-ligand (N1 and N2 in the first and N3 and N4 in the second molecule). Therefore, if we consider, that the second carboxylate ligand occupies just one coordination site, then coordination environments of Pb1 and Pb2 atoms may be described as pseudo-square-pyramidal.

The weak intermolecular interactions Pb1···O2i [3.359 (3) Å, i -x, 1 - y, 2 - z] and Pb2···O7ii [3.046 (3) Å, ii 1 - x, 1 - y,1 - z] link the molecules of complex into centrosymmetric dimers (Fig.2). The H-bonds involving carboxylic H atoms of solvate benzoic acid molecules and metal coordinated carboxylate O atoms (Table 1), link molecules of the complex and benzoic acid solvates into insular aggregates.

Experimental

A mixture of Pb(CH3COO)2.3H2O (0.199 g, 0.52 mmol), benzoic acid (0.102 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 393 K for 6 days to give the colorless crystals suitable for X-ray diffraction analysis.

Refinement

All H atoms bound to C atoms were placed in calculated positions and treated in a riding-model approximation, with C —H = 0.93 Å and Uiso (H) = 1.2 Ueq(C). The positions of carboxylic H atoms were located in the difference Fourier maps and included in the refinement in riding motion approximation with idealized distance of O—H = 0.85 Å and Uiso (H) = 1.2 Ueq(O). One of the the benzoic acid molecules [C56—C57—C58—C59—C60—C61—C62—O11—O12—H12] showed high thermal parameters and was subsequently represented as disordered over two sites, with refined occupancies of 0.496 (5) and 0.504 (5). The displacement parameters for the corresponding non-hydrogen atoms in the disordered phenyl rings were set equal (six EADP instructions; see, Sheldrick, 2008). The highest residual peak of 1.17 e Å-3 is located at the distance of 0.89 Å from Pb1; the deepest hole -1.13 e Å-3 is at 0.65 Å from the same atom.

Figures

Fig. 1.
The asymmetric unit of the title complex, showing displacement ellipsoids at the 30% probability level and the atom-labeling scheme. The H atoms and one of the components of the disordered benzoic acid molecule have been omitted for clarity.
Fig. 2.
The packing diagram viewed down the a axis; the H atoms not involved in H-bonding and the minor component of the disordered benzoic acid molecule are omitted for clarity. The H-bonds are shown as dashed lines in blue; the weak intermolecular Pb···O ...

Crystal data

[Pb(C7H5O2)2(C10H8N2)]·C7H6O2Z = 4
Mr = 727.71F(000) = 1416
Triclinic, P1Dx = 1.763 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.6298 (2) ÅCell parameters from 9902 reflections
b = 10.4264 (2) Åθ = 0.7–29.0°
c = 28.7365 (5) ŵ = 6.2 mm1
α = 84.843 (1)°T = 296 K
β = 88.128 (1)°Prism, colorless
γ = 72.619 (1)°0.24 × 0.19 × 0.15 mm
V = 2742.32 (9) Å3

Data collection

Bruker APEXII CCD area-detector diffractometer14302 independent reflections
Radiation source: fine-focus sealed tube10344 reflections with I > 2σ(I)
graphiteRint = 0.039
[var phi] and ω scansθmax = 29.0°, θmin = 0.7°
Absorption correction: multi-scan (SADABS; Bruker, 2007)h = −13→13
Tmin = 0.253, Tmax = 0.395k = −14→14
49796 measured reflectionsl = −39→38

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.081H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0359P)2 + 1.7335P] where P = (Fo2 + 2Fc2)/3
14302 reflections(Δ/σ)max = 0.001
773 parametersΔρmax = 1.17 e Å3
0 restraintsΔρmin = −1.13 e Å3

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

xyzUiso*/UeqOcc. (<1)
Pb10.277299 (17)0.440644 (16)0.990310 (6)0.04756 (5)
O10.2560 (3)0.3122 (3)0.92887 (10)0.0547 (8)
O20.0401 (4)0.4189 (4)0.95610 (12)0.0651 (9)
O30.4510 (4)0.5195 (4)0.93842 (13)0.0708 (10)
O40.2300 (4)0.6359 (4)0.91565 (12)0.0686 (9)
N10.5126 (4)0.2401 (4)1.00026 (13)0.0481 (8)
N20.2611 (4)0.2258 (4)1.04054 (13)0.0550 (9)
C10.1188 (5)0.3474 (5)0.92752 (15)0.0498 (10)
C20.0484 (4)0.2956 (5)0.88972 (14)0.0472 (10)
C3−0.0994 (5)0.3513 (6)0.8821 (2)0.0701 (15)
H3A−0.15410.41770.90040.084*
C4−0.1656 (6)0.3084 (7)0.8472 (2)0.0832 (18)
H4A−0.26490.34640.84220.100*
C5−0.0878 (6)0.2115 (6)0.8203 (2)0.0745 (15)
H5A−0.13290.18510.79630.089*
C60.0567 (6)0.1529 (6)0.82847 (18)0.0720 (15)
H6A0.10930.08280.81120.086*
C70.1257 (5)0.1975 (5)0.86266 (16)0.0588 (12)
H7A0.22530.16010.86710.071*
C80.3649 (5)0.6109 (5)0.91275 (16)0.0550 (11)
C90.3456 (6)0.7990 (6)0.85076 (19)0.0774 (17)
H9A0.24580.82980.85610.093*
C100.4109 (8)0.8652 (7)0.8160 (2)0.101 (2)
H10A0.35400.93970.79800.121*
C110.5556 (8)0.8217 (7)0.8087 (3)0.104 (2)
H11A0.59800.86500.78520.125*
C120.6389 (7)0.7157 (7)0.8353 (3)0.093 (2)
H12A0.73920.68760.83060.112*
C130.5777 (6)0.6490 (6)0.86907 (19)0.0689 (14)
H13A0.63670.57580.88710.083*
C140.4301 (5)0.6884 (5)0.87676 (15)0.0524 (11)
C150.1347 (6)0.2245 (6)1.0599 (2)0.0748 (15)
H15A0.05250.29601.05180.090*
C160.1199 (8)0.1232 (7)1.0910 (2)0.0899 (19)
H16A0.02920.12481.10360.108*
C170.2395 (9)0.0198 (7)1.1034 (2)0.098 (2)
H17A0.2321−0.05061.12470.118*
C180.3724 (7)0.0200 (6)1.08416 (19)0.0774 (16)
H18A0.4558−0.04991.09240.093*
C190.3799 (5)0.1252 (5)1.05259 (15)0.0522 (11)
C200.5193 (5)0.1345 (5)1.03072 (15)0.0492 (10)
C210.6504 (6)0.0360 (5)1.04115 (19)0.0673 (14)
H21A0.6527−0.04031.06090.081*
C220.7757 (6)0.0531 (7)1.0220 (2)0.0832 (18)
H22A0.8650−0.00831.03040.100*
C230.7700 (5)0.1604 (6)0.9904 (2)0.0806 (17)
H23A0.85420.17150.97610.097*
C240.6360 (5)0.2517 (5)0.98016 (19)0.0618 (13)
H24A0.63120.32450.95840.074*
Pb20.260139 (17)0.547049 (16)0.492170 (5)0.04398 (5)
O50.1638 (3)0.6596 (3)0.41827 (10)0.0517 (7)
O6−0.0072 (4)0.5925 (4)0.45613 (11)0.0684 (10)
O70.4867 (3)0.4786 (3)0.44324 (10)0.0539 (8)
O80.3453 (4)0.3496 (3)0.43410 (12)0.0654 (9)
N30.0919 (4)0.7500 (4)0.53414 (13)0.0516 (9)
N40.3238 (4)0.7697 (4)0.48246 (12)0.0496 (9)
C250.0347 (5)0.6481 (4)0.42089 (14)0.0462 (10)
C26−0.0617 (5)0.7019 (4)0.38005 (15)0.0468 (10)
C27−0.1856 (6)0.6646 (7)0.3762 (2)0.087 (2)
H27A−0.21020.60870.40000.105*
C28−0.2740 (7)0.7079 (8)0.3380 (3)0.109 (3)
H28A−0.35680.68030.33590.131*
C29−0.2417 (7)0.7903 (7)0.3033 (2)0.094 (2)
H29A−0.30130.81880.27720.113*
C30−0.1203 (6)0.8320 (6)0.30662 (18)0.0682 (14)
H30A−0.09870.89040.28310.082*
C31−0.0309 (5)0.7874 (5)0.34468 (16)0.0505 (10)
H31A0.05160.81550.34660.061*
C320.4552 (5)0.3858 (4)0.42343 (15)0.0476 (10)
C330.5526 (4)0.3229 (4)0.38502 (14)0.0443 (9)
C340.6673 (5)0.3672 (5)0.36900 (17)0.0588 (12)
H34A0.68750.43600.38340.071*
C350.7531 (6)0.3129 (6)0.3324 (2)0.0751 (16)
H35A0.82970.34550.32200.090*
C360.7259 (7)0.2110 (7)0.3112 (2)0.0877 (19)
H36A0.78370.17360.28640.105*
C370.6126 (8)0.1644 (7)0.3268 (2)0.096 (2)
H37A0.59440.09410.31270.116*
C380.5253 (6)0.2207 (5)0.3631 (2)0.0702 (15)
H38A0.44740.18950.37290.084*
C39−0.0144 (5)0.7296 (5)0.56216 (18)0.0634 (13)
H39A−0.04360.65350.55920.076*
C40−0.0815 (6)0.8135 (6)0.5945 (2)0.0759 (16)
H40A−0.15600.79630.61300.091*
C41−0.0370 (7)0.9251 (7)0.5994 (2)0.0896 (19)
H41A−0.08000.98420.62170.108*
C420.0709 (6)0.9484 (6)0.57104 (19)0.0719 (15)
H42A0.10081.02440.57360.086*
C430.1358 (5)0.8587 (4)0.53846 (15)0.0489 (10)
C440.2496 (5)0.8770 (4)0.50499 (15)0.0477 (10)
C450.2771 (6)0.9997 (5)0.49649 (19)0.0656 (14)
H45A0.22791.07180.51340.079*
C460.3775 (6)1.0149 (6)0.4629 (2)0.0761 (16)
H46A0.39481.09780.45620.091*
C470.4508 (6)0.9065 (6)0.43973 (19)0.0704 (15)
H47A0.52030.91430.41730.084*
C480.4218 (5)0.7836 (5)0.44951 (17)0.0595 (12)
H48A0.47080.71040.43300.071*
O90.3064 (6)0.8312 (6)0.32918 (16)0.1072 (16)
O100.3206 (4)0.6176 (4)0.33971 (12)0.0809 (11)
H100.27580.63640.36530.097*
C490.3429 (5)0.7208 (8)0.31470 (19)0.0713 (16)
C500.4195 (5)0.6882 (7)0.27012 (16)0.0645 (15)
C510.4360 (5)0.7919 (7)0.23990 (18)0.0747 (16)
H51A0.39780.88070.24720.090*
C520.5129 (6)0.7617 (9)0.1968 (2)0.088 (2)
H52A0.52510.83130.17600.105*
C530.5679 (7)0.6322 (10)0.1863 (2)0.098 (2)
H53A0.61740.61210.15830.117*
C540.5493 (7)0.5302 (9)0.2178 (2)0.095 (2)
H54A0.58900.44110.21090.113*
C550.4748 (6)0.5561 (7)0.25873 (19)0.0782 (18)
H55A0.46120.48570.27880.094*
O11A0.1002 (9)0.0133 (8)0.2570 (3)0.089 (3)0.496 (5)
O12A0.2529 (7)0.0710 (6)0.3016 (2)0.0624 (19)0.496 (5)
H12C0.2823−0.01200.31130.075*0.496 (5)
C56A0.1453 (11)0.0975 (10)0.2712 (4)0.054 (2)0.496 (5)
C57A0.0816 (7)0.2391 (6)0.24973 (19)0.081 (6)0.496 (5)
C58A−0.0179 (5)0.2866 (5)0.21357 (15)0.089 (6)0.496 (5)
H58A−0.04590.22620.19690.107*0.496 (5)
C59A−0.0754 (5)0.4246 (5)0.2023 (2)0.101 (5)0.496 (5)
H59A−0.14190.45640.17810.121*0.496 (5)
C60A−0.0334 (8)0.5150 (6)0.2273 (3)0.098 (5)0.496 (5)
H60A−0.07190.60730.21970.117*0.496 (5)
C61A0.0661 (9)0.4674 (8)0.2634 (2)0.097 (6)0.496 (5)
H61A0.09410.52790.28010.116*0.496 (5)
C62A0.1236 (8)0.3294 (9)0.2747 (2)0.088 (5)0.496 (5)
H62A0.19010.29760.29890.105*0.496 (5)
O11B−0.0444 (8)0.1612 (5)0.1905 (2)0.082 (2)0.504 (5)
O12B−0.0935 (6)0.3742 (6)0.16037 (18)0.066 (2)0.504 (5)
H12B−0.13360.34920.13840.079*0.504 (5)
C56B−0.0404 (13)0.2721 (13)0.1906 (4)0.057 (3)0.504 (5)
C57B0.0307 (7)0.3092 (8)0.2309 (2)0.045 (3)0.504 (5)
C58B0.0251 (9)0.4409 (7)0.2377 (3)0.066 (3)0.504 (5)
H58B−0.03260.51230.21860.079*0.504 (5)
C59B0.1058 (10)0.4660 (7)0.2732 (3)0.079 (5)0.504 (5)
H59B0.10200.55420.27780.095*0.504 (5)
C60B0.1921 (9)0.3594 (9)0.3018 (3)0.082 (4)0.504 (5)
H60B0.24610.37620.32550.098*0.504 (5)
C61B0.1977 (8)0.2276 (8)0.2950 (2)0.083 (4)0.504 (5)
H61B0.25550.15630.31410.099*0.504 (5)
C62B0.1171 (8)0.2025 (6)0.2595 (3)0.057 (4)0.504 (5)
H62B0.12080.11440.25490.068*0.504 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pb10.05027 (10)0.04123 (10)0.04718 (10)−0.00703 (7)−0.00101 (7)−0.00521 (7)
O10.0420 (16)0.064 (2)0.0543 (18)−0.0066 (14)−0.0052 (13)−0.0125 (16)
O20.0580 (19)0.072 (2)0.061 (2)−0.0073 (17)0.0029 (16)−0.0239 (18)
O30.070 (2)0.059 (2)0.071 (2)−0.0065 (18)0.0017 (18)0.0121 (19)
O40.059 (2)0.079 (3)0.063 (2)−0.0167 (18)0.0036 (16)0.0039 (19)
N10.0443 (19)0.042 (2)0.056 (2)−0.0074 (16)−0.0069 (16)−0.0083 (17)
N20.051 (2)0.051 (2)0.056 (2)−0.0076 (18)0.0036 (17)−0.0005 (18)
C10.051 (3)0.052 (3)0.045 (2)−0.012 (2)−0.0015 (19)0.000 (2)
C20.043 (2)0.055 (3)0.040 (2)−0.010 (2)−0.0002 (17)−0.002 (2)
C30.041 (2)0.084 (4)0.080 (4)−0.005 (2)−0.004 (2)−0.021 (3)
C40.049 (3)0.096 (5)0.102 (5)−0.012 (3)−0.021 (3)−0.020 (4)
C50.067 (3)0.089 (4)0.074 (4)−0.030 (3)−0.021 (3)−0.011 (3)
C60.077 (4)0.078 (4)0.053 (3)−0.006 (3)−0.005 (2)−0.021 (3)
C70.046 (2)0.071 (3)0.052 (3)−0.006 (2)−0.005 (2)−0.009 (2)
C80.065 (3)0.051 (3)0.043 (2)−0.006 (2)−0.001 (2)−0.009 (2)
C90.070 (3)0.067 (4)0.070 (3)0.010 (3)0.017 (3)0.010 (3)
C100.124 (6)0.071 (4)0.082 (4)0.000 (4)0.021 (4)0.022 (3)
C110.115 (6)0.077 (5)0.107 (5)−0.019 (4)0.056 (4)0.003 (4)
C120.076 (4)0.093 (5)0.112 (5)−0.029 (4)0.034 (4)−0.012 (4)
C130.063 (3)0.064 (3)0.073 (3)−0.010 (3)0.004 (3)−0.006 (3)
C140.058 (3)0.050 (3)0.045 (2)−0.010 (2)0.007 (2)−0.009 (2)
C150.069 (3)0.073 (4)0.076 (4)−0.016 (3)0.017 (3)−0.003 (3)
C160.094 (5)0.088 (5)0.090 (4)−0.035 (4)0.025 (4)0.002 (4)
C170.127 (6)0.081 (5)0.088 (5)−0.041 (4)0.010 (4)0.022 (4)
C180.094 (4)0.062 (4)0.070 (4)−0.018 (3)−0.010 (3)0.015 (3)
C190.065 (3)0.044 (3)0.045 (2)−0.011 (2)−0.006 (2)−0.006 (2)
C200.052 (2)0.044 (3)0.047 (2)−0.0047 (19)−0.0122 (19)−0.010 (2)
C210.065 (3)0.057 (3)0.067 (3)0.002 (2)−0.013 (3)0.003 (3)
C220.056 (3)0.082 (5)0.092 (4)0.010 (3)−0.018 (3)−0.007 (4)
C230.043 (3)0.078 (4)0.113 (5)−0.005 (3)−0.001 (3)−0.015 (4)
C240.047 (3)0.058 (3)0.080 (3)−0.014 (2)−0.001 (2)−0.010 (3)
Pb20.05568 (10)0.04077 (10)0.03725 (9)−0.01737 (7)−0.00074 (7)−0.00191 (7)
O50.0558 (18)0.061 (2)0.0414 (16)−0.0237 (15)−0.0062 (13)0.0025 (14)
O60.078 (2)0.088 (3)0.0513 (19)−0.048 (2)−0.0061 (16)0.0106 (18)
O70.0624 (19)0.052 (2)0.0499 (17)−0.0199 (15)0.0022 (14)−0.0101 (15)
O80.069 (2)0.066 (2)0.073 (2)−0.0363 (18)0.0264 (17)−0.0249 (18)
N30.056 (2)0.041 (2)0.060 (2)−0.0181 (17)0.0005 (18)−0.0059 (18)
N40.059 (2)0.048 (2)0.046 (2)−0.0217 (18)−0.0087 (17)0.0001 (17)
C250.056 (3)0.046 (3)0.039 (2)−0.020 (2)−0.0021 (18)−0.0071 (19)
C260.051 (2)0.046 (3)0.046 (2)−0.017 (2)−0.0032 (18)−0.008 (2)
C270.081 (4)0.114 (5)0.082 (4)−0.060 (4)−0.029 (3)0.028 (4)
C280.088 (4)0.140 (7)0.117 (6)−0.069 (5)−0.050 (4)0.030 (5)
C290.088 (4)0.101 (5)0.092 (5)−0.032 (4)−0.046 (4)0.016 (4)
C300.074 (3)0.065 (3)0.058 (3)−0.012 (3)−0.011 (3)0.010 (3)
C310.050 (2)0.046 (3)0.053 (3)−0.012 (2)−0.0044 (19)−0.004 (2)
C320.057 (3)0.039 (2)0.046 (2)−0.013 (2)−0.0019 (19)−0.002 (2)
C330.049 (2)0.038 (2)0.045 (2)−0.0111 (18)−0.0006 (18)0.0008 (18)
C340.055 (3)0.066 (3)0.059 (3)−0.024 (2)0.002 (2)−0.008 (2)
C350.061 (3)0.089 (4)0.075 (4)−0.025 (3)0.015 (3)−0.004 (3)
C360.083 (4)0.091 (5)0.084 (4)−0.017 (4)0.033 (3)−0.025 (4)
C370.114 (5)0.088 (5)0.101 (5)−0.042 (4)0.037 (4)−0.055 (4)
C380.074 (3)0.059 (3)0.087 (4)−0.031 (3)0.021 (3)−0.028 (3)
C390.061 (3)0.061 (3)0.070 (3)−0.022 (3)0.006 (2)−0.005 (3)
C400.067 (3)0.085 (4)0.078 (4)−0.026 (3)0.019 (3)−0.017 (3)
C410.095 (4)0.091 (5)0.088 (4)−0.028 (4)0.029 (4)−0.040 (4)
C420.094 (4)0.056 (3)0.072 (4)−0.027 (3)0.006 (3)−0.025 (3)
C430.054 (2)0.043 (3)0.049 (2)−0.013 (2)−0.0095 (19)−0.004 (2)
C440.057 (3)0.037 (2)0.051 (2)−0.018 (2)−0.019 (2)0.003 (2)
C450.078 (3)0.044 (3)0.078 (4)−0.023 (3)−0.008 (3)−0.004 (3)
C460.082 (4)0.048 (3)0.104 (5)−0.032 (3)−0.012 (3)0.010 (3)
C470.079 (4)0.071 (4)0.071 (3)−0.043 (3)−0.001 (3)0.012 (3)
C480.066 (3)0.063 (3)0.055 (3)−0.028 (3)0.000 (2)0.002 (2)
O90.135 (4)0.127 (4)0.089 (3)−0.079 (4)0.048 (3)−0.040 (3)
O100.079 (2)0.096 (3)0.054 (2)−0.010 (2)0.0122 (18)0.006 (2)
C490.050 (3)0.115 (5)0.054 (3)−0.033 (3)−0.001 (2)−0.011 (3)
C500.046 (3)0.110 (5)0.043 (3)−0.030 (3)−0.001 (2)−0.008 (3)
C510.056 (3)0.115 (5)0.060 (3)−0.037 (3)−0.002 (2)−0.003 (3)
C520.066 (4)0.144 (7)0.062 (4)−0.048 (4)−0.004 (3)0.002 (4)
C530.076 (4)0.169 (8)0.057 (4)−0.045 (5)0.006 (3)−0.025 (5)
C540.090 (5)0.129 (6)0.067 (4)−0.031 (4)0.008 (3)−0.033 (4)
C550.067 (4)0.104 (5)0.063 (4)−0.019 (3)0.004 (3)−0.026 (4)
O11A0.100 (6)0.061 (5)0.117 (7)−0.035 (5)−0.016 (5)−0.022 (5)
O12A0.074 (5)0.040 (4)0.070 (5)−0.013 (3)0.004 (4)−0.002 (3)
C56A0.055 (6)0.041 (6)0.064 (6)−0.013 (5)0.015 (5)−0.002 (5)
C57A0.096 (11)0.049 (8)0.113 (15)−0.042 (9)0.071 (11)−0.041 (10)
C58A0.060 (9)0.136 (17)0.081 (14)−0.040 (9)0.005 (9)−0.026 (12)
C59A0.066 (8)0.092 (11)0.121 (13)−0.002 (7)0.015 (8)0.033 (10)
C60A0.097 (11)0.051 (8)0.135 (14)−0.015 (7)0.026 (9)0.016 (9)
C61A0.080 (9)0.148 (19)0.076 (11)−0.053 (11)0.004 (9)−0.011 (11)
C62A0.067 (7)0.085 (10)0.076 (9)0.013 (7)0.021 (6)0.042 (8)
O11B0.098 (6)0.065 (5)0.090 (6)−0.032 (4)−0.020 (4)−0.008 (4)
O12B0.076 (5)0.063 (5)0.061 (4)−0.022 (4)−0.016 (3)−0.002 (4)
C56B0.055 (6)0.057 (7)0.064 (8)−0.019 (5)0.005 (5)−0.018 (6)
C57B0.055 (7)0.030 (5)0.041 (6)0.000 (4)0.007 (4)0.005 (4)
C58B0.068 (8)0.058 (8)0.061 (7)−0.009 (6)−0.001 (6)0.008 (6)
C59B0.099 (10)0.052 (8)0.103 (11)−0.038 (7)−0.012 (8)−0.031 (7)
C60B0.092 (9)0.088 (10)0.069 (8)−0.034 (8)−0.007 (6)−0.008 (7)
C61B0.068 (7)0.102 (11)0.066 (7)−0.010 (7)−0.002 (5)0.006 (7)
C62B0.054 (6)0.109 (13)0.022 (4)−0.048 (7)−0.005 (4)−0.002 (6)

Geometric parameters (Å, °)

Pb1—O12.359 (3)C29—H29A0.9300
Pb1—O22.594 (3)C30—C311.373 (6)
Pb1—O32.477 (4)C30—H30A0.9300
Pb1—O42.771 (4)C31—H31A0.9300
Pb1—N12.587 (3)C32—C331.491 (6)
Pb1—N22.596 (4)C33—C341.370 (6)
Pb1—O2i3.359 (3)C33—C381.378 (6)
O1—C11.262 (5)C34—C351.372 (7)
O2—C11.239 (5)C34—H34A0.9300
O3—C81.258 (5)C35—C361.365 (8)
O4—C81.247 (6)C35—H35A0.9300
N1—C201.331 (6)C36—C371.368 (8)
N1—C241.338 (6)C36—H36A0.9300
N2—C151.325 (6)C37—C381.379 (7)
N2—C191.331 (5)C37—H37A0.9300
C1—C21.518 (6)C38—H38A0.9300
C2—C71.362 (6)C39—C401.347 (7)
C2—C31.384 (6)C39—H39A0.9300
C3—C41.379 (7)C40—C411.374 (8)
C3—H3A0.9300C40—H40A0.9300
C4—C51.353 (8)C41—C421.365 (8)
C4—H4A0.9300C41—H41A0.9300
C5—C61.361 (7)C42—C431.383 (7)
C5—H5A0.9300C42—H42A0.9300
C6—C71.390 (7)C43—C441.478 (6)
C6—H6A0.9300C44—C451.381 (6)
C7—H7A0.9300C45—C461.377 (8)
C8—C141.493 (6)C45—H45A0.9300
C9—C141.369 (7)C46—C471.359 (8)
C9—C101.401 (8)C46—H46A0.9300
C9—H9A0.9300C47—C481.394 (7)
C10—C111.346 (9)C47—H47A0.9300
C10—H10A0.9300C48—H48A0.9300
C11—C121.344 (9)O9—C491.208 (7)
C11—H11A0.9300O10—C491.307 (7)
C12—C131.364 (8)O10—H100.8500
C12—H12A0.9300C49—C501.472 (7)
C13—C141.373 (7)C50—C511.368 (8)
C13—H13A0.9300C50—C551.385 (8)
C15—C161.360 (8)C51—C521.432 (8)
C15—H15A0.9300C51—H51A0.9300
C16—C171.353 (9)C52—C531.353 (10)
C16—H16A0.9300C52—H52A0.9300
C17—C181.377 (9)C53—C541.384 (10)
C17—H17A0.9300C53—H53A0.9300
C18—C191.377 (7)C54—C551.363 (8)
C18—H18A0.9300C54—H54A0.9300
C19—C201.489 (6)C55—H55A0.9300
C20—C211.391 (6)O11A—C56A1.197 (12)
C21—C221.364 (8)O12A—C56A1.325 (12)
C21—H21A0.9300O12A—H12C0.8500
C22—C231.364 (8)C56A—C57A1.501 (11)
C22—H22A0.9300C57A—C58A1.3900
C23—C241.377 (7)C57A—C62A1.3900
C23—H23A0.9300C58A—C59A1.3900
C24—H24A0.9300C58A—H58A0.9300
Pb2—O52.404 (3)C59A—C60A1.3900
Pb2—O62.698 (3)C59A—H59A0.9300
Pb2—O72.509 (3)C60A—C61A1.3900
Pb2—O82.686 (3)C60A—H60A0.9300
Pb2—N32.615 (4)C61A—C62A1.3900
Pb2—N42.562 (4)C61A—H61A0.9300
Pb2—O7ii3.046 (3)C62A—H62A0.9300
O5—C251.283 (5)O11B—C56B1.169 (13)
O6—C251.238 (5)O12B—C56B1.299 (13)
O7—C321.279 (5)O12B—H12B0.8500
O8—C321.247 (5)C56B—C57B1.499 (13)
N3—C391.336 (6)C57B—C58B1.3900
N3—C431.339 (5)C57B—C62B1.3900
N4—C441.343 (6)C58B—C59B1.3900
N4—C481.344 (6)C58B—H58B0.9300
C25—C261.482 (6)C59B—C60B1.3900
C26—C271.372 (6)C59B—H59B0.9300
C26—C311.375 (6)C60B—C61B1.3900
C27—C281.370 (8)C60B—H60B0.9300
C27—H27A0.9300C61B—C62B1.3900
C28—C291.346 (9)C61B—H61B0.9300
C28—H28A0.9300C62B—H62B0.9300
C29—C301.372 (8)
O1—Pb1—O385.77 (12)O6—C25—C26121.2 (4)
O1—Pb1—N178.51 (10)O5—C25—C26117.7 (4)
O3—Pb1—N177.71 (11)C27—C26—C31117.6 (4)
O1—Pb1—O252.47 (10)C27—C26—C25119.9 (4)
O3—Pb1—O2119.86 (12)C31—C26—C25122.5 (4)
N1—Pb1—O2122.69 (11)C28—C27—C26121.4 (5)
O1—Pb1—N281.89 (12)C28—C27—H27A119.3
O3—Pb1—N2139.91 (11)C26—C27—H27A119.3
N1—Pb1—N262.50 (12)C29—C28—C27120.4 (5)
O2—Pb1—N281.03 (12)C29—C28—H28A119.8
O1—Pb1—C126.42 (11)C27—C28—H28A119.8
O3—Pb1—C1102.85 (13)C28—C29—C30119.6 (5)
N1—Pb1—C1101.75 (12)C28—C29—H29A120.2
O2—Pb1—C126.10 (11)C30—C29—H29A120.2
N2—Pb1—C181.72 (13)C29—C30—C31120.0 (5)
O1—Pb1—O2i113.58 (9)C29—C30—H30A120.0
O3—Pb1—O2i136.89 (10)C31—C30—H30A120.0
N1—Pb1—O2i141.64 (11)C30—C31—C26120.9 (4)
O2—Pb1—O2i61.44 (11)C30—C31—H31A119.5
N2—Pb1—O2i82.59 (10)C26—C31—H31A119.5
C1—Pb1—O2i87.48 (11)O8—C32—O7122.7 (4)
C1—O1—Pb197.3 (3)O8—C32—C33119.5 (4)
C1—O2—Pb186.8 (3)O7—C32—C33117.8 (4)
C8—O3—Pb1100.9 (3)C34—C33—C38117.8 (4)
C20—N1—C24118.6 (4)C34—C33—C32122.0 (4)
C20—N1—Pb1121.2 (3)C38—C33—C32120.2 (4)
C24—N1—Pb1119.3 (3)C33—C34—C35121.9 (5)
C15—N2—C19119.0 (4)C33—C34—H34A119.0
C15—N2—Pb1118.9 (3)C35—C34—H34A119.0
C19—N2—Pb1121.4 (3)C36—C35—C34119.8 (5)
O2—C1—O1123.2 (4)C36—C35—H35A120.1
O2—C1—C2119.1 (4)C34—C35—H35A120.1
O1—C1—C2117.8 (4)C35—C36—C37119.3 (5)
O2—C1—Pb167.1 (3)C35—C36—H36A120.3
O1—C1—Pb156.3 (2)C37—C36—H36A120.3
C2—C1—Pb1173.2 (3)C36—C37—C38120.5 (6)
C7—C2—C3118.8 (4)C36—C37—H37A119.7
C7—C2—C1122.4 (4)C38—C37—H37A119.7
C3—C2—C1118.8 (4)C33—C38—C37120.6 (5)
C4—C3—C2120.0 (5)C33—C38—H38A119.7
C4—C3—H3A120.0C37—C38—H38A119.7
C2—C3—H3A120.0N3—C39—C40123.6 (5)
C5—C4—C3120.8 (5)N3—C39—H39A118.2
C5—C4—H4A119.6C40—C39—H39A118.2
C3—C4—H4A119.6C39—C40—C41118.2 (5)
C4—C5—C6119.8 (5)C39—C40—H40A120.9
C4—C5—H5A120.1C41—C40—H40A120.9
C6—C5—H5A120.1C42—C41—C40119.3 (5)
C5—C6—C7120.1 (5)C42—C41—H41A120.3
C5—C6—H6A120.0C40—C41—H41A120.3
C7—C6—H6A120.0C41—C42—C43119.8 (5)
C2—C7—C6120.5 (4)C41—C42—H42A120.1
C2—C7—H7A119.8C43—C42—H42A120.1
C6—C7—H7A119.8N3—C43—C42120.3 (4)
O4—C8—O3122.7 (5)N3—C43—C44115.5 (4)
O4—C8—C14119.9 (4)C42—C43—C44124.2 (4)
O3—C8—C14117.3 (4)N4—C44—C45121.2 (4)
C14—C9—C10119.3 (5)N4—C44—C43117.2 (4)
C14—C9—H9A120.3C45—C44—C43121.6 (4)
C10—C9—H9A120.3C46—C45—C44119.9 (5)
C11—C10—C9120.4 (6)C46—C45—H45A120.1
C11—C10—H10A119.8C44—C45—H45A120.1
C9—C10—H10A119.8C47—C46—C45118.7 (5)
C12—C11—C10120.1 (6)C47—C46—H46A120.7
C12—C11—H11A119.9C45—C46—H46A120.7
C10—C11—H11A119.9C46—C47—C48120.1 (5)
C11—C12—C13120.5 (6)C46—C47—H47A120.0
C11—C12—H12A119.7C48—C47—H47A120.0
C13—C12—H12A119.7N4—C48—C47120.8 (5)
C12—C13—C14120.9 (6)N4—C48—H48A119.6
C12—C13—H13A119.5C47—C48—H48A119.6
C14—C13—H13A119.5C49—O10—H10114.6
C9—C14—C13118.7 (5)O9—C49—O10120.6 (5)
C9—C14—C8121.4 (4)O9—C49—C50124.8 (6)
C13—C14—C8120.0 (4)O10—C49—C50114.6 (6)
N2—C15—C16122.8 (6)C51—C50—C55120.2 (5)
N2—C15—H15A118.6C51—C50—C49118.4 (6)
C16—C15—H15A118.6C55—C50—C49121.3 (6)
C17—C16—C15118.8 (6)C50—C51—C52119.1 (6)
C17—C16—H16A120.6C50—C51—H51A120.4
C15—C16—H16A120.6C52—C51—H51A120.4
C16—C17—C18119.2 (6)C53—C52—C51120.2 (7)
C16—C17—H17A120.4C53—C52—H52A119.9
C18—C17—H17A120.4C51—C52—H52A119.9
C19—C18—C17119.1 (6)C52—C53—C54119.0 (6)
C19—C18—H18A120.4C52—C53—H53A120.5
C17—C18—H18A120.4C54—C53—H53A120.5
N2—C19—C18120.9 (5)C55—C54—C53122.1 (7)
N2—C19—C20116.5 (4)C55—C54—H54A119.0
C18—C19—C20122.6 (5)C53—C54—H54A119.0
N1—C20—C21121.4 (5)C54—C55—C50119.4 (7)
N1—C20—C19117.1 (4)C54—C55—H55A120.3
C21—C20—C19121.4 (5)C50—C55—H55A120.3
C22—C21—C20118.9 (5)C56A—O12A—H12C112.4
C22—C21—H21A120.5O11A—C56A—O12A123.9 (10)
C20—C21—H21A120.5O11A—C56A—C57A116.3 (10)
C21—C22—C23120.0 (5)O12A—C56A—C57A119.6 (8)
C21—C22—H22A120.0C58A—C57A—C62A120.0
C23—C22—H22A120.0C58A—C57A—C56A129.3 (5)
C22—C23—C24118.2 (5)C62A—C57A—C56A110.4 (5)
C22—C23—H23A120.9C59A—C58A—C57A120.0
C24—C23—H23A120.9C59A—C58A—H58A120.0
N1—C24—C23122.8 (5)C57A—C58A—H58A120.0
N1—C24—H24A118.6C60A—C59A—C58A120.0
C23—C24—H24A118.6C60A—C59A—H59A120.0
O5—Pb2—O780.77 (10)C58A—C59A—H59A120.0
O5—Pb2—N472.88 (10)C59A—C60A—C61A120.0
O7—Pb2—N479.87 (11)C59A—C60A—H60A120.0
O5—Pb2—N389.37 (11)C61A—C60A—H60A120.0
O7—Pb2—N3142.43 (11)C62A—C61A—C60A120.0
N4—Pb2—N362.61 (12)C62A—C61A—H61A120.0
O5—Pb2—O877.15 (11)C60A—C61A—H61A120.0
O7—Pb2—O850.36 (10)C61A—C62A—C57A120.0
N4—Pb2—O8125.09 (11)C61A—C62A—H62A120.0
N3—Pb2—O8160.03 (11)C57A—C62A—H62A120.0
O5—Pb2—O650.57 (9)C56B—O12B—H12B109.5
O7—Pb2—O6122.01 (10)O11B—C56B—O12B128.9 (10)
N4—Pb2—O6107.79 (11)O11B—C56B—C57B118.7 (11)
N3—Pb2—O674.58 (11)O12B—C56B—C57B112.5 (10)
O8—Pb2—O685.46 (11)C58B—C57B—C62B120.0
O5—Pb2—O7ii139.48 (9)C58B—C57B—C56B123.4 (8)
O7—Pb2—O7ii73.74 (10)C62B—C57B—C56B116.3 (8)
N4—Pb2—O7ii72.03 (10)C57B—C58B—C59B120.0
N3—Pb2—O7ii92.05 (10)C57B—C58B—H58B120.0
O8—Pb2—O7ii107.79 (10)C59B—C58B—H58B120.0
O6—Pb2—O7ii164.22 (10)C60B—C59B—C58B120.0
C25—O5—Pb2100.5 (2)C60B—C59B—H59B120.0
C25—O6—Pb287.8 (3)C58B—C59B—H59B120.0
C32—O7—Pb297.1 (3)C61B—C60B—C59B120.0
C32—O8—Pb289.6 (3)C61B—C60B—H60B120.0
C39—N3—C43118.7 (4)C59B—C60B—H60B120.0
C39—N3—Pb2118.8 (3)C62B—C61B—C60B120.0
C43—N3—Pb2119.7 (3)C62B—C61B—H61B120.0
C44—N4—C48119.4 (4)C60B—C61B—H61B120.0
C44—N4—Pb2121.8 (3)C61B—C62B—C57B120.0
C48—N4—Pb2118.3 (3)C61B—C62B—H62B120.0
O6—C25—O5121.1 (4)C57B—C62B—H62B120.0

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O10—H10···O50.851.832.670 (5)171
O12A—H12C···O9iii0.851.622.459 (9)169
O12B—H12B···O4iv0.851.812.612 (6)158

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YA2132).

References

  • Alvarado, R. J., Rosenberg, J. M., Andreu, A., Bryan, J. C., Chen, W.-Z., Ren, T. & Kavallieratos, K. (2005). Inorg. Chem.44, 7951–7959. [PubMed]
  • Bruker (2007). APEX2, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fan, S. R. & Zhu, L. G. (2006). Inorg. Chem.45, 7935–7942. [PubMed]
  • Hamilton, B. H., Kelley, K. A., Wagler, T. A., Espe, M. P. & Ziegler, C. J. (2004). Inorg. Chem.43, 50–56. [PubMed]
  • Masaoka, S., Furukawa, S., Chang, H. C., Mizutani, T. & Kitagawa, S. (2001). Angew. Chem. Int. Ed.40, 3817–3819. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, X. L., Qin, C. & Wang, E. B. (2006). Cryst. Growth Des.6, 439–443.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography