supplementary materials


HTML versionpdf versioncif file3d viewstructure factorssupplementary materialsCIF check reportsimilar papers Open access

si2072 scheme

Acta Cryst. (2008). E64, m712-m713    [ doi:10.1107/S1600536808010805 ]

catena-Poly[[[bis[4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol-[kappa]2N7,N8]lead(II)]-[mu]-4,4'-oxydibenzoato-[kappa]3O,O':O''] dihydrate]

M.-L. Xu, R. Zhou, G.-Y. Wang and S. W. Ng

Abstract top

The carboxylate dianion in the title compound, [Pb(C14H8O5)(C19H12N4O)2]·2H2O, uses one carboxylate group to O,O'-chelate a bis[4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol]-chelated PbII atom and uses its other carboxylate group to bind to another PbII atom in an irregular monodentate manner. The PbII atom exists in an undefined seven-coordinate geometry in the chain structure; the lone pair is stereochemically active. Adjacent chains are linked by intermolecular O-H...N, N-H...O and O-H...O hydrogen bonds that involve the uncoordinated water molecules to form a three-dimensional network.

Comment top

The 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol N-heterocycle furnishes adducts with metal dicarboxylates (Xu et al., 2008).

The carboxylate dianion in the title chain compound uses one carboxyl –CO2 group to O,O'-chelate to the lead(II) atom and uses its other carboxyl end to bind to another lead atom in a unidentate manner. The lead atom exists in an undefined seven-coordinate geometry; the Pb—O distances range between 2.582 (5) and 2.824 (5) Å, and the Pb—N distances vary between 2.506 (6) and 2.672 (6) Å (Table 1). The lone-pair is stereochemically active. Adjacent chains are linked by intermolecular O—H···N, N—H···O and O—H···O hydrogen bonds (Table 2) that involve the lattice water molecules to form a three-dimensional network.

Related literature top

For transition metal dicarboxylate adducts of 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol, see: Xu et al. (2008).

Experimental top

Lead(II) nitrate (0.1 mmol), 1,4-oxobis(benzoic acid), 4-(1H-1,3,7,8-tetraazacyclopenta[l]phenanthren-2-yl)phenol (0.1 mmol) and water (14 ml) were heated in a 23 ml, Teflon-lined, stainless-steel Parr bomb at 458 K for 3 days. Crystals were obtained in 30% yield.

Refinement top

The carbon- and nitrogen-bound H atoms were placed in calculated positions [C—H 0.93, N—H 0.86, O—H 0.82 Å and Uiso(H)= 1.2Ueq(C, N, O)], and were included in the refinement in the riding-model approximation.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot of a portion of the chain structure of Pb(C19H12N4O)2(C14H8O5).2H2O; displacement ellipsoids are drawn at the 50% probability level, and H atoms as spheres of arbitrary radius. Symmetry codes are given in Table 1.
[Figure 2] Fig. 2. Seven-coordinate environment of lead.
catena-Poly[[[bis[4-(1H-1,3,7,8-tetraazacyclopenta[l] phenanthren-2-yl)phenol-κ2N7,N8]lead(II)]-µ-4,4'- oxydibenzoato-κ3O,O':O''] dihydrate] top
Crystal data top
[Pb(C14H8O5)(C19H12N4O)2]·2H2OF000 = 2232
Mr = 1124.08Dx = 1.709 Mg m−3
Monoclinic, P21/nMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 24960 reflections
a = 10.767 (4) Åθ = 3.0–27.5º
b = 29.916 (7) ŵ = 3.93 mm−1
c = 13.688 (4) ÅT = 295 (2) K
β = 97.70 (1)ºBlock, colorless
V = 4369 (2) Å30.33 × 0.24 × 0.21 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID
diffractometer		9977 independent reflections
Radiation source: fine-focus sealed tube6235 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.063
Detector resolution: 10 pixels mm-1θmax = 27.5º
T = 295(2) Kθmin = 3.0º
ω scansh = −13→13
Absorption correction: Multi-scan
(ABSCOR; Higashi, 1995)		k = −38→38
Tmin = 0.188, Tmax = 0.492l = −17→17
42355 measured reflections
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)] = 0.055H-atom parameters constrained
wR(F2) = 0.168  w = 1/[σ2(Fo2) + (0.0814P)2 + 9.1333P]
where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
9977 reflectionsΔρmax = 1.52 e Å−3
631 parametersΔρmin = −1.09 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
[Pb(C14H8O5)(C19H12N4O)2]·2H2OV = 4369 (2) Å3
Mr = 1124.08Z = 4
Monoclinic, P21/nMo Kα
a = 10.767 (4) ŵ = 3.93 mm−1
b = 29.916 (7) ÅT = 295 (2) K
c = 13.688 (4) Å0.33 × 0.24 × 0.21 mm
β = 97.70 (1)º
Data collection top
Rigaku R-AXIS RAPID
diffractometer		9977 independent reflections
Absorption correction: Multi-scan
(ABSCOR; Higashi, 1995)		6235 reflections with I > 2σ(I)
Tmin = 0.188, Tmax = 0.492Rint = 0.063
42355 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.055631 parameters
wR(F2) = 0.168H-atom parameters constrained
S = 1.02Δρmax = 1.52 e Å−3
9977 reflectionsΔρmin = −1.09 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Pb10.22221 (3)0.252248 (8)0.632884 (19)0.04982 (12)
O10.1768 (7)0.31678 (17)0.5080 (4)0.0838 (19)
O20.1246 (6)0.33913 (18)0.6496 (4)0.0704 (15)
O30.2197 (8)0.5257 (2)0.4374 (5)0.099 (2)
O40.4930 (7)0.6379 (2)0.7966 (5)0.094 (2)
O50.3496 (9)0.6846 (2)0.7428 (5)0.114 (3)
O61.0871 (7)0.0039 (2)0.2469 (5)0.092 (2)
H6O1.09940.00680.18940.138*
O70.9813 (8)0.5095 (3)1.2543 (5)0.124 (3)
H7O1.04420.52231.24080.186*
O1W0.8513 (7)0.0694 (2)0.6615 (5)0.097 (2)
H1W10.80470.07780.61270.145*
H1W20.81020.06430.70660.145*
O2W0.8223 (7)0.4435 (3)0.7773 (5)0.128 (3)
H2W10.77570.42590.80050.191*
H2W20.79580.44770.71910.191*
N10.3196 (6)0.2288 (2)0.4707 (4)0.0541 (15)
N20.4077 (6)0.19747 (19)0.6534 (4)0.0560 (15)
N30.6337 (6)0.13120 (19)0.3461 (4)0.0542 (15)
H3N0.62760.13560.28360.065*
N40.7003 (6)0.10439 (19)0.4949 (4)0.0554 (15)
N50.3031 (6)0.27173 (18)0.8164 (4)0.0491 (14)
N60.4143 (6)0.30027 (19)0.6616 (4)0.0512 (14)
N70.6079 (6)0.36530 (19)1.0242 (4)0.0516 (14)
H7N0.58990.36321.08340.062*
N80.7061 (6)0.38671 (19)0.8986 (4)0.0536 (15)
C10.1535 (8)0.3474 (3)0.5655 (6)0.065 (2)
C20.1686 (8)0.3954 (3)0.5314 (6)0.061 (2)
C30.1180 (8)0.4303 (2)0.5783 (6)0.066 (2)
H30.07160.42480.62970.079*
C40.1373 (9)0.4749 (3)0.5474 (6)0.069 (2)
H40.10440.49880.57880.082*
C50.2045 (9)0.4823 (3)0.4712 (7)0.072 (2)
C60.2548 (10)0.4470 (3)0.4242 (7)0.084 (3)
H60.29910.45280.37170.101*
C70.2405 (9)0.4042 (3)0.4532 (6)0.075 (3)
H70.27720.38080.42250.090*
C80.2650 (11)0.5560 (3)0.5087 (6)0.079 (3)
C90.3789 (11)0.5484 (3)0.5651 (7)0.098 (3)
H90.42520.52300.55480.117*
C100.4246 (11)0.5793 (3)0.6381 (7)0.096 (3)
H100.50000.57370.67790.115*
C110.3572 (9)0.6186 (3)0.6515 (6)0.070 (2)
C120.2442 (9)0.6260 (4)0.5880 (7)0.084 (3)
H120.19930.65230.59340.101*
C130.2011 (9)0.5948 (3)0.5191 (7)0.077 (2)
H130.12640.60010.47810.093*
C140.4078 (11)0.6516 (3)0.7334 (7)0.090 (3)
C150.2765 (9)0.2453 (2)0.3820 (6)0.065 (2)
H150.21130.26590.37680.078*
C160.3252 (10)0.2329 (3)0.2974 (5)0.072 (2)
H160.29460.24570.23710.086*
C170.4159 (8)0.2026 (3)0.3029 (5)0.061 (2)
H170.44840.19370.24630.073*
C180.4623 (7)0.1841 (2)0.3943 (5)0.0534 (18)
C190.4116 (7)0.1985 (2)0.4769 (5)0.0478 (16)
C200.5610 (7)0.1511 (2)0.4104 (5)0.0522 (17)
C210.7153 (8)0.1039 (2)0.3996 (6)0.0575 (19)
C220.8102 (8)0.0774 (3)0.3582 (6)0.060 (2)
C230.8326 (9)0.0832 (2)0.2636 (6)0.066 (2)
H230.78730.10440.22400.079*
C240.9235 (9)0.0574 (3)0.2253 (6)0.069 (2)
H240.93530.06030.15960.083*
C250.9933 (9)0.0285 (3)0.2840 (7)0.076 (2)
C260.9773 (12)0.0230 (4)0.3790 (7)0.116 (5)
H261.02650.00300.41940.139*
C270.8852 (12)0.0481 (4)0.4143 (8)0.110 (4)
H270.87390.04470.48010.132*
C280.6054 (7)0.1341 (2)0.5018 (5)0.0519 (17)
C290.5571 (8)0.1494 (2)0.5886 (5)0.0532 (18)
C300.4597 (7)0.1814 (2)0.5749 (5)0.0475 (16)
C310.5963 (9)0.1339 (3)0.6837 (6)0.075 (3)
H310.65770.11190.69440.090*
C320.5450 (10)0.1509 (3)0.7599 (6)0.088 (3)
H320.57330.14180.82400.106*
C330.4502 (9)0.1819 (3)0.7424 (6)0.072 (2)
H330.41390.19250.79580.087*
C340.2457 (8)0.2584 (2)0.8911 (6)0.0573 (19)
H340.17710.23940.87780.069*
C350.2824 (8)0.2712 (3)0.9875 (6)0.062 (2)
H350.23850.26101.03720.074*
C360.3824 (7)0.2986 (2)1.0100 (5)0.0542 (18)
H360.40860.30721.07490.065*
C370.4461 (6)0.3140 (2)0.9323 (5)0.0439 (15)
C380.4027 (7)0.2994 (2)0.8353 (5)0.0445 (15)
C390.5495 (7)0.3434 (2)0.9428 (5)0.0487 (16)
C400.6998 (7)0.3911 (2)0.9936 (5)0.0534 (18)
C410.7755 (7)0.4217 (3)1.0608 (6)0.0593 (19)
C420.7432 (11)0.4316 (4)1.1507 (8)0.116 (5)
H420.67390.41751.17070.140*
C430.8099 (13)0.4621 (5)1.2140 (9)0.133 (6)
H430.78260.46981.27330.160*
C440.9163 (9)0.4804 (3)1.1872 (7)0.083 (3)
C450.9535 (8)0.4709 (3)1.1008 (6)0.073 (2)
H451.02650.48341.08340.087*
C460.8813 (8)0.4416 (3)1.0360 (6)0.072 (2)
H460.90590.43560.97480.086*
C470.6115 (6)0.3568 (2)0.8667 (5)0.0493 (16)
C480.5710 (7)0.3414 (2)0.7678 (5)0.0496 (16)
C490.4643 (7)0.3140 (2)0.7525 (5)0.0477 (16)
C500.6268 (8)0.3542 (3)0.6863 (6)0.066 (2)
H500.69800.37220.69440.079*
C510.5767 (9)0.3404 (3)0.5946 (6)0.074 (2)
H510.61320.34860.53940.089*
C520.4692 (9)0.3134 (3)0.5850 (6)0.068 (2)
H520.43490.30430.52220.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Pb10.06011 (19)0.04550 (16)0.04314 (16)−0.00172 (12)0.00430 (12)−0.00412 (12)
O10.151 (6)0.047 (3)0.056 (3)0.019 (3)0.023 (4)0.001 (3)
O20.094 (4)0.069 (3)0.053 (3)0.002 (3)0.026 (3)0.002 (3)
O30.154 (7)0.065 (4)0.074 (4)−0.025 (4)0.000 (4)0.002 (3)
O40.112 (6)0.090 (5)0.074 (4)−0.002 (4)−0.007 (4)−0.011 (4)
O50.199 (9)0.065 (4)0.080 (5)0.022 (5)0.032 (5)−0.011 (4)
O60.108 (5)0.098 (5)0.077 (4)0.016 (4)0.039 (4)−0.020 (4)
O70.129 (7)0.160 (7)0.088 (5)−0.084 (6)0.031 (5)−0.058 (5)
O1W0.109 (5)0.111 (5)0.067 (4)0.035 (4)0.003 (4)−0.012 (4)
O2W0.120 (6)0.166 (8)0.087 (5)−0.080 (6)−0.021 (4)0.042 (5)
N10.075 (4)0.050 (3)0.036 (3)−0.001 (3)0.003 (3)−0.004 (3)
N20.077 (4)0.051 (3)0.042 (3)0.009 (3)0.013 (3)−0.001 (3)
N30.079 (4)0.052 (3)0.034 (3)0.000 (3)0.015 (3)−0.004 (3)
N40.071 (4)0.050 (3)0.046 (3)0.007 (3)0.013 (3)−0.007 (3)
N50.062 (4)0.042 (3)0.044 (3)−0.008 (3)0.012 (3)−0.007 (3)
N60.065 (4)0.052 (3)0.036 (3)−0.005 (3)0.005 (3)−0.007 (3)
N70.061 (4)0.051 (3)0.042 (3)−0.005 (3)0.004 (3)−0.006 (3)
N80.056 (4)0.052 (3)0.053 (4)−0.005 (3)0.006 (3)−0.002 (3)
C10.086 (6)0.054 (4)0.056 (5)0.011 (4)0.012 (4)0.000 (4)
C20.067 (5)0.058 (4)0.054 (5)−0.002 (4)0.000 (4)0.004 (4)
C30.084 (6)0.053 (4)0.060 (5)0.008 (4)0.004 (4)−0.004 (4)
C40.088 (6)0.057 (4)0.060 (5)0.005 (4)0.005 (5)−0.006 (4)
C50.088 (6)0.055 (4)0.072 (6)−0.009 (4)0.011 (5)−0.001 (4)
C60.115 (8)0.064 (5)0.078 (6)−0.008 (5)0.027 (6)0.006 (5)
C70.099 (7)0.067 (5)0.062 (5)−0.014 (5)0.027 (5)−0.001 (4)
C80.124 (9)0.062 (5)0.049 (5)−0.018 (5)0.006 (5)0.003 (4)
C90.135 (10)0.073 (6)0.076 (6)0.026 (6)−0.018 (6)0.001 (5)
C100.128 (9)0.074 (6)0.077 (6)0.021 (6)−0.015 (6)−0.018 (5)
C110.090 (7)0.060 (5)0.063 (5)0.001 (4)0.022 (5)0.004 (4)
C120.081 (7)0.091 (7)0.079 (6)0.008 (5)0.007 (5)0.002 (6)
C130.076 (6)0.080 (6)0.074 (6)−0.007 (5)0.003 (5)−0.002 (5)
C140.133 (9)0.078 (6)0.050 (5)0.044 (6)−0.021 (5)−0.011 (5)
C150.083 (6)0.062 (5)0.047 (4)0.009 (4)−0.001 (4)0.000 (4)
C160.109 (7)0.069 (5)0.032 (4)0.008 (5)−0.004 (4)−0.003 (4)
C170.080 (6)0.066 (5)0.036 (4)0.000 (4)0.009 (4)0.003 (3)
C180.073 (5)0.051 (4)0.039 (4)−0.010 (3)0.015 (4)−0.006 (3)
C190.064 (5)0.041 (3)0.036 (3)−0.004 (3)0.001 (3)−0.001 (3)
C200.073 (5)0.046 (3)0.039 (4)−0.002 (3)0.011 (3)0.001 (3)
C210.076 (5)0.051 (4)0.048 (4)0.004 (4)0.014 (4)−0.011 (3)
C220.077 (6)0.056 (4)0.049 (4)0.000 (4)0.017 (4)−0.010 (4)
C230.091 (6)0.051 (4)0.058 (5)−0.002 (4)0.018 (4)−0.012 (4)
C240.087 (6)0.069 (5)0.056 (5)0.002 (5)0.029 (5)−0.012 (4)
C250.094 (7)0.065 (5)0.074 (6)0.010 (5)0.030 (5)−0.015 (5)
C260.158 (12)0.124 (9)0.073 (7)0.084 (8)0.043 (7)0.016 (6)
C270.160 (12)0.112 (8)0.066 (6)0.057 (8)0.042 (7)0.001 (6)
C280.067 (5)0.049 (4)0.041 (4)0.001 (3)0.014 (3)−0.005 (3)
C290.075 (5)0.048 (4)0.038 (4)0.006 (3)0.010 (3)0.001 (3)
C300.065 (5)0.045 (3)0.033 (3)−0.005 (3)0.008 (3)−0.003 (3)
C310.098 (7)0.081 (6)0.048 (5)0.035 (5)0.020 (4)0.010 (4)
C320.117 (8)0.102 (7)0.045 (5)0.047 (6)0.013 (5)0.018 (5)
C330.099 (7)0.076 (5)0.043 (4)0.033 (5)0.013 (4)0.004 (4)
C340.062 (5)0.053 (4)0.058 (5)−0.012 (3)0.011 (4)−0.011 (4)
C350.083 (6)0.059 (4)0.046 (4)−0.005 (4)0.020 (4)0.002 (4)
C360.068 (5)0.058 (4)0.036 (4)−0.002 (4)0.004 (3)−0.003 (3)
C370.049 (4)0.044 (3)0.038 (3)0.004 (3)0.003 (3)0.003 (3)
C380.057 (4)0.038 (3)0.038 (3)0.002 (3)0.006 (3)−0.004 (3)
C390.060 (4)0.046 (3)0.040 (4)−0.003 (3)0.005 (3)−0.004 (3)
C400.059 (5)0.051 (4)0.048 (4)−0.005 (3)0.000 (3)−0.004 (3)
C410.060 (5)0.069 (5)0.048 (4)−0.011 (4)0.002 (4)−0.012 (4)
C420.128 (10)0.151 (11)0.077 (7)−0.090 (8)0.038 (7)−0.027 (7)
C430.151 (12)0.174 (12)0.084 (8)−0.102 (10)0.049 (8)−0.067 (8)
C440.076 (6)0.101 (7)0.070 (6)−0.040 (5)0.008 (5)−0.024 (5)
C450.072 (6)0.090 (6)0.056 (5)−0.027 (5)0.005 (4)−0.012 (5)
C460.083 (6)0.079 (5)0.052 (5)−0.019 (5)0.007 (4)−0.007 (4)
C470.048 (4)0.046 (3)0.053 (4)0.004 (3)0.002 (3)0.001 (3)
C480.061 (5)0.046 (4)0.043 (4)0.000 (3)0.011 (3)0.001 (3)
C490.054 (4)0.043 (3)0.046 (4)0.002 (3)0.009 (3)0.001 (3)
C500.073 (6)0.064 (5)0.059 (5)−0.018 (4)0.005 (4)−0.002 (4)
C510.096 (7)0.078 (6)0.051 (5)−0.023 (5)0.021 (5)0.000 (4)
C520.090 (6)0.070 (5)0.046 (4)−0.017 (5)0.014 (4)−0.003 (4)
Geometric parameters (Å, °) top
Pb1—O12.582 (5)C13—H130.9300
Pb1—O22.824 (5)C15—C161.384 (12)
Pb1—O5i2.818 (6)C15—H150.9300
Pb1—N12.672 (6)C16—C171.327 (11)
Pb1—N22.570 (6)C16—H160.9300
Pb1—N52.612 (6)C17—C181.398 (10)
Pb1—N62.506 (6)C17—H170.9300
O1—C11.255 (9)C18—C191.388 (9)
O2—C11.257 (9)C18—C201.446 (10)
O3—C81.371 (10)C19—C301.464 (9)
O3—C51.397 (9)C20—C281.376 (9)
O4—C141.243 (10)C21—C221.466 (11)
O5—C141.184 (10)C22—C271.357 (12)
O6—C251.398 (10)C22—C231.360 (10)
O6—H6O0.8200C23—C241.402 (11)
O7—C441.385 (10)C23—H230.9300
O7—H7O0.8201C24—C251.339 (12)
O1W—H1W10.8199C24—H240.9300
O1W—H1W20.8200C25—C261.344 (12)
O2W—H2W10.8199C26—C271.383 (13)
O2W—H2W20.8201C26—H260.9300
N1—C151.335 (10)C27—H270.9300
N1—C191.339 (9)C28—C291.434 (9)
N2—C331.327 (9)C29—C311.393 (10)
N2—C301.364 (9)C29—C301.413 (10)
N3—C211.343 (10)C31—C321.344 (11)
N3—C201.387 (9)C31—H310.9300
N3—H3N0.8600C32—C331.377 (11)
N4—C211.335 (9)C32—H320.9300
N4—C281.367 (9)C33—H330.9300
N5—C341.325 (10)C34—C351.381 (11)
N5—C381.353 (8)C34—H340.9300
N6—C521.330 (9)C35—C361.356 (10)
N6—C491.352 (8)C35—H350.9300
N7—C401.364 (9)C36—C371.417 (9)
N7—C391.371 (8)C36—H360.9300
N7—H7N0.8600C37—C391.410 (9)
N8—C401.318 (9)C37—C381.417 (9)
N8—C471.382 (9)C38—C491.454 (9)
C1—C21.524 (11)C39—C471.371 (10)
C2—C31.376 (11)C40—C411.466 (10)
C2—C71.427 (11)C41—C421.355 (12)
C3—C41.423 (11)C41—C461.368 (11)
C3—H30.9300C42—C431.390 (13)
C4—C51.364 (12)C42—H420.9300
C4—H40.9300C43—C441.363 (13)
C5—C61.383 (12)C43—H430.9300
C6—C71.357 (11)C44—C451.330 (12)
C6—H60.9300C45—C461.405 (11)
C7—H70.9300C45—H450.9300
C8—C131.369 (13)C46—H460.9300
C8—C91.378 (13)C47—C481.440 (9)
C9—C101.399 (13)C48—C501.390 (11)
C9—H90.9300C48—C491.404 (10)
C10—C111.407 (12)C50—C511.363 (11)
C10—H100.9300C50—H500.9300
C11—C121.415 (13)C51—C521.403 (12)
C11—C141.539 (12)C51—H510.9300
C12—C131.364 (13)C52—H520.9300
C12—H120.9300
N6—Pb1—N274.7 (2)N1—C19—C18121.8 (6)
N6—Pb1—O175.8 (2)N1—C19—C30117.6 (6)
N2—Pb1—O1128.6 (2)C18—C19—C30120.6 (7)
N6—Pb1—N563.86 (18)C28—C20—N3105.2 (6)
N2—Pb1—N583.28 (19)C28—C20—C18123.3 (6)
O1—Pb1—N5118.63 (18)N3—C20—C18131.4 (6)
N6—Pb1—N182.70 (18)N4—C21—N3111.7 (6)
N2—Pb1—N162.47 (18)N4—C21—C22124.4 (7)
O1—Pb1—N172.93 (18)N3—C21—C22123.9 (7)
N5—Pb1—N1137.72 (19)C27—C22—C23117.0 (8)
N6—Pb1—O5i127.2 (2)C27—C22—C21121.6 (8)
N2—Pb1—O5i75.4 (2)C23—C22—C21121.4 (8)
O1—Pb1—O5i153.4 (3)C22—C23—C24120.4 (8)
N5—Pb1—O5i70.28 (19)C22—C23—H23119.8
N1—Pb1—O5i118.9 (2)C24—C23—H23119.8
N6—Pb1—O276.57 (18)C25—C24—C23119.7 (8)
N2—Pb1—O2150.48 (19)C25—C24—H24120.1
O1—Pb1—O247.62 (16)C23—C24—H24120.1
N5—Pb1—O278.26 (17)C24—C25—C26121.6 (9)
N1—Pb1—O2120.01 (17)C24—C25—O6119.8 (8)
O5i—Pb1—O2118.49 (19)C26—C25—O6118.6 (9)
C1—O1—Pb199.6 (5)C25—C26—C27117.5 (10)
C1—O2—Pb188.1 (4)C25—C26—H26121.2
C8—O3—C5115.1 (7)C27—C26—H26121.2
C25—O6—H6O120.7C22—C27—C26123.6 (9)
C44—O7—H7O120.1C22—C27—H27118.2
H1W1—O1W—H1W2109.8C26—C27—H27118.2
H2W1—O2W—H2W2108.8N4—C28—C20110.4 (6)
C15—N1—C19118.1 (6)N4—C28—C29128.5 (7)
C15—N1—Pb1122.1 (5)C20—C28—C29121.0 (7)
C19—N1—Pb1119.7 (4)C31—C29—C30118.4 (7)
C33—N2—C30118.1 (6)C31—C29—C28124.7 (7)
C33—N2—Pb1119.4 (5)C30—C29—C28116.8 (6)
C30—N2—Pb1122.3 (5)N2—C30—C29120.7 (6)
C21—N3—C20107.3 (6)N2—C30—C19117.8 (6)
C21—N3—H3N126.3C29—C30—C19121.5 (6)
C20—N3—H3N126.3C32—C31—C29119.7 (8)
C21—N4—C28105.4 (6)C32—C31—H31120.1
C34—N5—C38118.5 (6)C29—C31—H31120.1
C34—N5—Pb1123.0 (5)C31—C32—C33119.4 (8)
C38—N5—Pb1118.3 (4)C31—C32—H32120.3
C52—N6—C49118.1 (7)C33—C32—H32120.3
C52—N6—Pb1119.4 (5)N2—C33—C32123.6 (8)
C49—N6—Pb1122.5 (5)N2—C33—H33118.2
C40—N7—C39107.1 (6)C32—C33—H33118.2
C40—N7—H7N126.5N5—C34—C35123.4 (7)
C39—N7—H7N126.5N5—C34—H34118.3
C40—N8—C47104.0 (6)C35—C34—H34118.3
O2—C1—O1121.6 (7)C36—C35—C34120.2 (7)
O2—C1—C2121.0 (7)C36—C35—H35119.9
O1—C1—C2117.3 (7)C34—C35—H35119.9
C3—C2—C7119.9 (8)C35—C36—C37118.4 (6)
C3—C2—C1120.5 (8)C35—C36—H36120.8
C7—C2—C1119.5 (8)C37—C36—H36120.8
C2—C3—C4119.3 (8)C39—C37—C38116.3 (6)
C2—C3—H3120.3C39—C37—C36125.5 (6)
C4—C3—H3120.3C38—C37—C36118.2 (6)
C5—C4—C3119.5 (8)N5—C38—C37121.4 (6)
C5—C4—H4120.2N5—C38—C49117.9 (6)
C3—C4—H4120.2C37—C38—C49120.8 (6)
C4—C5—C6120.9 (8)N7—C39—C47105.1 (6)
C4—C5—O3120.1 (8)N7—C39—C37130.6 (6)
C6—C5—O3119.0 (9)C47—C39—C37124.3 (6)
C7—C6—C5121.1 (9)N8—C40—N7112.5 (6)
C7—C6—H6119.4N8—C40—C41125.7 (7)
C5—C6—H6119.4N7—C40—C41121.7 (7)
C6—C7—C2119.2 (9)C42—C41—C46117.0 (8)
C6—C7—H7120.4C42—C41—C40121.2 (8)
C2—C7—H7120.4C46—C41—C40121.8 (7)
O3—C8—C13119.9 (10)C41—C42—C43122.4 (9)
O3—C8—C9119.8 (9)C41—C42—H42118.8
C13—C8—C9120.2 (9)C43—C42—H42118.8
C8—C9—C10119.6 (10)C44—C43—C42118.6 (10)
C8—C9—H9120.2C44—C43—H43120.7
C10—C9—H9120.2C42—C43—H43120.7
C9—C10—C11120.4 (10)C45—C44—C43121.1 (9)
C9—C10—H10119.8C45—C44—O7122.6 (8)
C11—C10—H10119.8C43—C44—O7116.3 (9)
C10—C11—C12117.9 (9)C44—C45—C46119.2 (8)
C10—C11—C14119.6 (9)C44—C45—H45120.4
C12—C11—C14122.5 (8)C46—C45—H45120.4
C13—C12—C11120.2 (9)C41—C46—C45121.6 (8)
C13—C12—H12119.9C41—C46—H46119.2
C11—C12—H12119.9C45—C46—H46119.2
C8—C13—C12121.6 (9)C39—C47—N8111.3 (6)
C8—C13—H13119.2C39—C47—C48120.2 (6)
C12—C13—H13119.2N8—C47—C48128.4 (7)
O5—C14—O4123.5 (9)C50—C48—C49118.3 (7)
O5—C14—C11118.2 (9)C50—C48—C47123.8 (7)
O4—C14—C11116.7 (8)C49—C48—C47117.8 (6)
N1—C15—C16122.5 (8)N6—C49—C48122.1 (6)
N1—C15—H15118.7N6—C49—C38117.4 (6)
C16—C15—H15118.7C48—C49—C38120.5 (6)
C17—C16—C15119.6 (8)C51—C50—C48119.7 (8)
C17—C16—H16120.2C51—C50—H50120.2
C15—C16—H16120.2C48—C50—H50120.2
C16—C17—C18119.5 (7)C50—C51—C52118.8 (8)
C16—C17—H17120.2C50—C51—H51120.6
C18—C17—H17120.2C52—C51—H51120.6
C19—C18—C17118.3 (7)N6—C52—C51123.0 (7)
C19—C18—C20116.7 (6)N6—C52—H52118.5
C17—C18—C20125.0 (7)C51—C52—H52118.5
N6—Pb1—O1—C1−75.1 (6)C19—C18—C20—N3−177.2 (7)
N2—Pb1—O1—C1−131.5 (6)C17—C18—C20—N32.1 (13)
N5—Pb1—O1—C1−26.1 (6)C28—N4—C21—N3−0.9 (9)
N1—Pb1—O1—C1−161.7 (6)C28—N4—C21—C22178.3 (7)
O5i—Pb1—O1—C177.3 (7)C20—N3—C21—N40.3 (9)
O2—Pb1—O1—C19.6 (5)C20—N3—C21—C22−178.8 (7)
N6—Pb1—O2—C173.4 (5)N4—C21—C22—C275.3 (14)
N2—Pb1—O2—C186.6 (6)N3—C21—C22—C27−175.7 (9)
O1—Pb1—O2—C1−9.4 (5)N4—C21—C22—C23−170.4 (8)
N5—Pb1—O2—C1139.0 (5)N3—C21—C22—C238.6 (13)
N1—Pb1—O2—C10.2 (6)C27—C22—C23—C244.4 (13)
O5i—Pb1—O2—C1−161.3 (5)C21—C22—C23—C24−179.8 (8)
N6—Pb1—N1—C15−102.2 (6)C22—C23—C24—C25−3.5 (13)
N2—Pb1—N1—C15−178.7 (6)C23—C24—C25—C261.0 (16)
O1—Pb1—N1—C15−24.9 (6)C23—C24—C25—O6−177.7 (8)
N5—Pb1—N1—C15−139.0 (6)C24—C25—C26—C270.5 (19)
O5i—Pb1—N1—C15129.1 (6)O6—C25—C26—C27179.1 (11)
O2—Pb1—N1—C15−32.3 (6)C23—C22—C27—C26−3.0 (18)
N6—Pb1—N1—C1980.2 (5)C21—C22—C27—C26−178.8 (11)
N2—Pb1—N1—C193.8 (5)C25—C26—C27—C221(2)
O1—Pb1—N1—C19157.5 (6)C21—N4—C28—C201.1 (9)
N5—Pb1—N1—C1943.4 (6)C21—N4—C28—C29−175.5 (8)
O5i—Pb1—N1—C19−48.5 (6)N3—C20—C28—N4−0.9 (8)
O2—Pb1—N1—C19150.1 (5)C18—C20—C28—N4−178.6 (6)
N6—Pb1—N2—C3390.8 (7)N3—C20—C28—C29176.0 (7)
O1—Pb1—N2—C33147.7 (6)C18—C20—C28—C29−1.7 (11)
N5—Pb1—N2—C3326.1 (6)N4—C28—C29—C31−4.0 (13)
N1—Pb1—N2—C33−179.5 (7)C20—C28—C29—C31179.7 (8)
O5i—Pb1—N2—C33−45.2 (6)N4—C28—C29—C30178.4 (7)
O2—Pb1—N2—C3377.5 (7)C20—C28—C29—C302.2 (11)
N6—Pb1—N2—C30−93.5 (6)C33—N2—C30—C29−0.8 (11)
O1—Pb1—N2—C30−36.6 (6)Pb1—N2—C30—C29−176.5 (5)
N5—Pb1—N2—C30−158.2 (6)C33—N2—C30—C19179.5 (7)
N1—Pb1—N2—C30−3.8 (5)Pb1—N2—C30—C193.8 (9)
O5i—Pb1—N2—C30130.5 (6)C31—C29—C30—N21.7 (11)
O2—Pb1—N2—C30−106.8 (6)C28—C29—C30—N2179.4 (7)
N6—Pb1—N5—C34178.3 (6)C31—C29—C30—C19−178.6 (7)
N2—Pb1—N5—C34−105.6 (6)C28—C29—C30—C19−0.9 (10)
O1—Pb1—N5—C34123.7 (6)N1—C19—C30—N20.0 (10)
N1—Pb1—N5—C34−140.3 (5)C18—C19—C30—N2178.7 (7)
O5i—Pb1—N5—C34−28.7 (6)N1—C19—C30—C29−179.7 (7)
O2—Pb1—N5—C3497.6 (6)C18—C19—C30—C29−1.0 (10)
N6—Pb1—N5—C383.3 (4)C30—C29—C31—C32−2.8 (14)
N2—Pb1—N5—C3879.5 (5)C28—C29—C31—C32179.6 (9)
O1—Pb1—N5—C38−51.2 (5)C29—C31—C32—C333.0 (16)
N1—Pb1—N5—C3844.7 (6)C30—N2—C33—C321.0 (14)
O5i—Pb1—N5—C38156.4 (5)Pb1—N2—C33—C32176.8 (8)
O2—Pb1—N5—C38−77.3 (5)C31—C32—C33—N2−2.1 (17)
N2—Pb1—N6—C5288.8 (6)C38—N5—C34—C35−0.2 (11)
O1—Pb1—N6—C52−48.7 (6)Pb1—N5—C34—C35−175.1 (6)
N5—Pb1—N6—C52178.8 (7)N5—C34—C35—C36−0.4 (13)
N1—Pb1—N6—C5225.4 (6)C34—C35—C36—C370.8 (11)
O5i—Pb1—N6—C52146.4 (6)C35—C36—C37—C39178.4 (7)
O2—Pb1—N6—C52−97.9 (6)C35—C36—C37—C38−0.7 (10)
N2—Pb1—N6—C49−91.9 (5)C34—N5—C38—C370.3 (10)
O1—Pb1—N6—C49130.5 (6)Pb1—N5—C38—C37175.4 (5)
N5—Pb1—N6—C49−1.9 (5)C34—N5—C38—C49−179.7 (6)
N1—Pb1—N6—C49−155.3 (5)Pb1—N5—C38—C49−4.5 (8)
O5i—Pb1—N6—C49−34.3 (6)C39—C37—C38—N5−179.1 (6)
O2—Pb1—N6—C4981.4 (5)C36—C37—C38—N50.2 (10)
Pb1—O2—C1—O117.0 (9)C39—C37—C38—C490.9 (9)
Pb1—O2—C1—C2−159.6 (8)C36—C37—C38—C49−179.9 (6)
Pb1—O1—C1—O2−18.9 (10)C40—N7—C39—C470.9 (8)
Pb1—O1—C1—C2157.8 (6)C40—N7—C39—C37−177.5 (7)
O2—C1—C2—C3−18.4 (13)C38—C37—C39—N7175.5 (7)
O1—C1—C2—C3164.8 (8)C36—C37—C39—N7−3.7 (12)
O2—C1—C2—C7158.8 (8)C38—C37—C39—C47−2.6 (10)
O1—C1—C2—C7−18.0 (12)C36—C37—C39—C47178.2 (7)
C7—C2—C3—C40.5 (13)C47—N8—C40—N70.8 (8)
C1—C2—C3—C4177.7 (7)C47—N8—C40—C41−175.6 (7)
C2—C3—C4—C50.7 (13)C39—N7—C40—N8−1.1 (9)
C3—C4—C5—C6−0.4 (14)C39—N7—C40—C41175.5 (7)
C3—C4—C5—O3177.3 (8)N8—C40—C41—C42164.3 (10)
C8—O3—C5—C452.7 (13)N7—C40—C41—C42−11.8 (13)
C8—O3—C5—C6−129.6 (10)N8—C40—C41—C46−15.6 (13)
C4—C5—C6—C7−1.1 (16)N7—C40—C41—C46168.3 (8)
O3—C5—C6—C7−178.8 (9)C46—C41—C42—C433.0 (19)
C5—C6—C7—C22.3 (15)C40—C41—C42—C43−177.0 (12)
C3—C2—C7—C6−2.0 (14)C41—C42—C43—C44−4(2)
C1—C2—C7—C6−179.2 (9)C42—C43—C44—C453(2)
C5—O3—C8—C13−126.1 (10)C42—C43—C44—O7−178.0 (12)
C5—O3—C8—C958.3 (13)C43—C44—C45—C460.4 (18)
O3—C8—C9—C10−179.7 (10)O7—C44—C45—C46−178.9 (10)
C13—C8—C9—C104.6 (16)C42—C41—C46—C450.2 (15)
C8—C9—C10—C11−2.4 (17)C40—C41—C46—C45−179.9 (8)
C9—C10—C11—C12−1.1 (16)C44—C45—C46—C41−1.9 (15)
C9—C10—C11—C14178.9 (10)N7—C39—C47—N8−0.4 (8)
C10—C11—C12—C132.5 (14)C37—C39—C47—N8178.1 (6)
C14—C11—C12—C13−177.5 (10)N7—C39—C47—C48−177.4 (6)
O3—C8—C13—C12−178.9 (9)C37—C39—C47—C481.0 (11)
C9—C8—C13—C12−3.3 (16)C40—N8—C47—C39−0.2 (8)
C11—C12—C13—C8−0.4 (15)C40—N8—C47—C48176.5 (7)
C10—C11—C14—O5179.6 (11)C39—C47—C48—C50178.5 (7)
C12—C11—C14—O5−0.4 (16)N8—C47—C48—C502.0 (12)
C10—C11—C14—O4−13.9 (15)C39—C47—C48—C492.3 (10)
C12—C11—C14—O4166.1 (10)N8—C47—C48—C49−174.1 (7)
C19—N1—C15—C16−1.5 (12)C52—N6—C49—C480.2 (11)
Pb1—N1—C15—C16−179.1 (7)Pb1—N6—C49—C48−179.1 (5)
N1—C15—C16—C171.9 (14)C52—N6—C49—C38179.8 (7)
C15—C16—C17—C18−1.0 (13)Pb1—N6—C49—C380.5 (8)
C16—C17—C18—C19−0.4 (12)C50—C48—C49—N6−0.7 (11)
C16—C17—C18—C20−179.6 (8)C47—C48—C49—N6175.6 (6)
C15—N1—C19—C180.1 (11)C50—C48—C49—C38179.7 (7)
Pb1—N1—C19—C18177.8 (5)C47—C48—C49—C38−4.0 (10)
C15—N1—C19—C30178.8 (7)N5—C38—C49—N62.7 (9)
Pb1—N1—C19—C30−3.5 (8)C37—C38—C49—N6−177.2 (6)
C17—C18—C19—N10.8 (11)N5—C38—C49—C48−177.6 (6)
C20—C18—C19—N1−179.8 (6)C37—C38—C49—C482.4 (10)
C17—C18—C19—C30−177.9 (7)C49—C48—C50—C510.5 (12)
C20—C18—C19—C301.5 (10)C47—C48—C50—C51−175.6 (8)
C21—N3—C20—C280.3 (8)C48—C50—C51—C520.1 (14)
C21—N3—C20—C18177.8 (8)C49—N6—C52—C510.5 (13)
C19—C18—C20—C28−0.2 (11)Pb1—N6—C52—C51179.8 (7)
C17—C18—C20—C28179.1 (7)C50—C51—C52—N6−0.7 (14)
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O2ii0.861.982.82 (1)166
N7—H7N···O4iii0.861.972.81 (1)166
O1W—H1W1···N40.822.002.82 (1)174
O1W—H1W2···O6iv0.822.372.57 (1)95
O2W—H2W1···N80.822.002.79 (1)160
O2W—H2W2···O3v0.822.273.06 (1)160
Symmetry codes: (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y, −z+1; (v) −x+1, −y+1, −z+1.
Table 1
Selected geometric parameters (Å) top
Pb1—O12.582 (5)Pb1—N22.570 (6)
Pb1—O22.824 (5)Pb1—N52.612 (6)
Pb1—O5i2.818 (6)Pb1—N62.506 (6)
Pb1—N12.672 (6)
Symmetry codes: (i) −x+1/2, y−1/2, −z+3/2.
Table 2
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N3—H3N···O2ii0.861.982.82 (1)166
N7—H7N···O4iii0.861.972.81 (1)166
O1W—H1W1···N40.822.002.82 (1)174
O1W—H1W2···O6iv0.822.372.57 (1)95
O2W—H2W1···N80.822.002.79 (1)160
O2W—H2W2···O3v0.822.273.06 (1)160
Symmetry codes: (ii) x+1/2, −y+1/2, z−1/2; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y, −z+1; (v) −x+1, −y+1, −z+1.
Acknowledgements top

We thank Xi'an Modern Chemistry Research Institute and the University of Malaya for supporting this work.

references
References top

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.

Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.

Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2008). publCIF. In preparation.

Xu, M.-L., Zhao, R., Wang, G.-Y. & Ng, S. W. (2008). Acta Cryst. E64, m710–m711.