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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): m712–m713.
Published online 2008 April 23. doi:  10.1107/S1600536808010805
PMCID: PMC2961154

catena-Poly[[[bis­[4-(1H-1,3,7,8-tetra­azacyclo­penta­[l]phenanthren-2-yl)­phenol-κ2 N 7,N 8]lead(II)]-μ-4,4′-oxy­dibenzoato-κ3 O,O′:O′′] dihydrate]

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-64-0m712-scheme1.jpg

Experimental

Crystal data

  • [Pb(C14H8O5)(C19H12N4O)2]·2H2O
  • M r = 1124.08
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0m712-efi1.jpg
  • a = 10.767 (4) Å
  • b = 29.916 (7) Å
  • c = 13.688 (4) Å
  • β = 97.70 (1)°
  • V = 4369 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.93 mm−1
  • T = 295 (2) K
  • 0.33 × 0.24 × 0.21 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.188, T max = 0.492 (expected range = 0.167–0.438)
  • 42355 measured reflections
  • 9977 independent reflections
  • 6235 reflections with I > 2σ(I)
  • R int = 0.063

Refinement

  • R[F 2 > 2σ(F 2)] = 0.054
  • wR(F 2) = 0.168
  • S = 1.02
  • 9977 reflections
  • 631 parameters
  • H-atom parameters constrained
  • Δρmax = 1.51 e Å−3
  • Δρmin = −1.09 e Å−3

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

Table 1
Selected bond lengths (Å)
Table 2
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010805/si2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010805/si2072Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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

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.

Figures

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.
Fig. 2.
Seven-coordinate environment of lead.

Crystal data

[Pb(C14H8O5)(C19H12N4O)2]·2H2OF000 = 2232
Mr = 1124.08Dx = 1.709 Mg m3
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 mm1
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

Rigaku R-AXIS RAPID diffractometer9977 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

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 Å3
631 parametersΔρmin = −1.09 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SI2072).

References

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