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Acta Crystallogr Sect E Struct Rep Online. 2010 January 1; 66(Pt 1): m56.
Published online 2009 December 12. doi:  10.1107/S1600536809052647
PMCID: PMC2980214

μ-Adipato-κ2 O 1:O 4-bis­{[2,6-bis­(1H-benzimidazol-2-yl-κN 3)pyridine-κN](nitrato-κO)lead(II)}

Abstract

The dinuclear title compound, [Pb2(C6H8O4)(NO3)2(C19H13N5)2], lies with the mid-point of the butyl chain of the bridging adipate unit on a center of inversion. The PbII ion is covalently bonded to the nitrate anion and is bonded to a carboxyl­ate group of the adipate unit by another covalent bond. The N-heterocycle functions in a chelating tridentate mode. The metal atom exists in a Ψ-octa­hedral coordination environment. When weaker Pb(...)O inter­actions are also considered, the geometry is a Ψ-tricapped trigonal prism in which the lone-pair electrons occupy one face of the trigonal prism. Adjacent mol­ecules are linked into a layer structure by N—H(...)O hydrogen bonds.

Related literature

For the structure of a related PbII complex and its lone-pair sterechemistry, see: Meng et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-00m56-scheme1.jpg

Experimental

Crystal data

  • [Pb2(C6H8O4)(NO3)2(C19H13N5)2]
  • M r = 1305.21
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-00m56-efi1.jpg
  • a = 9.3470 (7) Å
  • b = 10.6433 (8) Å
  • c = 11.3776 (8) Å
  • α = 106.696 (1)°
  • β = 95.343 (1)°
  • γ = 99.117 (1)°
  • V = 1058.9 (1) Å3
  • Z = 1
  • Mo Kα radiation
  • μ = 8.02 mm−1
  • T = 293 K
  • 0.26 × 0.12 × 0.08 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.230, T max = 0.566
  • 8299 measured reflections
  • 4561 independent reflections
  • 3586 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.099
  • S = 1.02
  • 4561 reflections
  • 307 parameters
  • H-atom parameters constrained
  • Δρmax = 1.93 e Å−3
  • Δρmin = −1.17 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052647/bt5131sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809052647/bt5131Isup2.hkl

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

Acknowledgments

This work was supported by the Guangxi Graduate Education Innovation Program (2009106020703M44) and the University of Malaya.

supplementary crystallographic information

Experimental

Lead nitrate (0.250 mmol), 2-(6-(1H-benzo[d]imidazol-2-yl)pyridin-2-yl)-1H-benzo[d]imidazole (0.250 mmol), adipic acid (0.125 mmol) and water (10 ml) were sealed in a 25 ml Teflon-lined, stainless-steel Parr bomb. The bomb was heated at 413 K for 4 days and cooled to room temperature. Brown block-shaped crystals were colleacted and washed in water; the yield was 25%.

Refinement

Hydrogen atoms were generated geometrically and were constrained to ride on their parent atoms [C–H = 0.93, N–H 0.86 Å; Uiso(H) =1.2Ueq(C,N)].

The final difference Fourier map had a peak near C14 and a hole near H2a.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of Pb2(NO3)2(C6H8O4)(C19H13N5)2 at the 70% probability level; hydrogen atoms are drawn as sphere of arbitrary radius.
Fig. 2.
Detail of the coordination environment of the PbII centre.

Crystal data

[Pb2(C6H8O4)(NO3)2(C19H13N5)2]Z = 1
Mr = 1305.21F(000) = 626
Triclinic, P1Dx = 2.047 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3470 (7) ÅCell parameters from 3150 reflections
b = 10.6433 (8) Åθ = 2.2–24.8°
c = 11.3776 (8) ŵ = 8.02 mm1
α = 106.696 (1)°T = 293 K
β = 95.343 (1)°Block, brown
γ = 99.117 (1)°0.26 × 0.12 × 0.08 mm
V = 1058.9 (1) Å3

Data collection

Bruker APEXII diffractometer4561 independent reflections
Radiation source: fine-focus sealed tube3586 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 27.1°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.230, Tmax = 0.566k = −13→13
8299 measured reflectionsl = −14→14

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)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0524P)2] where P = (Fo2 + 2Fc2)/3
4561 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 1.93 e Å3
0 restraintsΔρmin = −1.17 e Å3

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

xyzUiso*/Ueq
Pb11.07669 (3)0.71714 (3)0.65491 (3)0.02682 (11)
O10.8637 (6)0.6980 (5)0.5092 (5)0.0341 (13)
O20.8304 (6)0.4985 (5)0.5330 (5)0.0381 (13)
O31.2560 (7)0.8902 (7)0.8623 (6)0.0579 (18)
O41.3952 (11)0.7543 (10)0.8022 (10)0.126 (5)
O51.4055 (12)0.8554 (14)0.9916 (9)0.141 (5)
N11.1854 (7)0.8782 (6)0.5449 (5)0.0286 (14)
N21.2263 (6)1.0797 (6)0.5237 (5)0.0274 (14)
H21.22151.16210.53430.033*
N31.0091 (7)0.9473 (6)0.7236 (5)0.0251 (13)
N40.8962 (7)0.7470 (6)0.8149 (6)0.0329 (15)
N50.7760 (7)0.8747 (6)0.9451 (6)0.0352 (16)
H50.74350.94400.98390.042*
N61.3504 (9)0.8307 (8)0.8859 (7)0.052 (2)
C11.2754 (8)0.8763 (7)0.4564 (7)0.0262 (16)
C21.3328 (9)0.7741 (8)0.3826 (7)0.0324 (18)
H2A1.31320.68820.38930.039*
C31.4197 (9)0.8036 (8)0.2989 (7)0.0349 (19)
H31.46000.73660.24900.042*
C41.4490 (9)0.9331 (9)0.2873 (7)0.0369 (19)
H41.50850.94990.23030.044*
C51.3918 (8)1.0343 (8)0.3581 (7)0.0350 (19)
H5A1.41061.12000.35080.042*
C61.3046 (8)1.0032 (7)0.4412 (7)0.0278 (16)
C71.1608 (8)1.0009 (7)0.5828 (6)0.0258 (16)
C81.0701 (7)1.0443 (7)0.6764 (6)0.0208 (14)
C91.0481 (8)1.1737 (7)0.7213 (8)0.0344 (18)
H91.08871.23920.68820.041*
C100.9640 (9)1.2052 (8)0.8172 (7)0.038 (2)
H100.95091.29260.84950.045*
C110.9004 (9)1.1077 (8)0.8642 (7)0.0340 (18)
H110.84281.12760.92690.041*
C120.9248 (8)0.9783 (7)0.8148 (7)0.0263 (16)
C130.8642 (8)0.8677 (8)0.8563 (7)0.0299 (17)
C140.7477 (9)0.7502 (8)0.9616 (8)0.0345 (18)
C150.6696 (9)0.7026 (9)1.0431 (8)0.041 (2)
H150.61690.75501.09600.049*
C160.6744 (9)0.5751 (10)1.0410 (8)0.046 (2)
H160.62580.54011.09580.056*
C170.7503 (11)0.4942 (10)0.9588 (9)0.056 (3)
H170.74830.40660.95900.067*
C180.8266 (11)0.5409 (9)0.8793 (9)0.050 (2)
H180.87820.48760.82610.060*
C190.8245 (9)0.6720 (8)0.8805 (7)0.0333 (18)
C200.7885 (8)0.5807 (7)0.4878 (7)0.0264 (16)
C210.6450 (8)0.5467 (8)0.4015 (8)0.039 (2)
H21A0.66060.49890.31870.047*
H21B0.61590.62920.39820.047*
C220.5208 (9)0.4628 (8)0.4384 (7)0.038 (2)
H22A0.55000.38110.44430.045*
H22B0.43610.43830.37460.045*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pb10.02973 (17)0.02289 (16)0.03042 (16)0.00981 (11)0.00830 (11)0.00846 (11)
O10.030 (3)0.025 (3)0.046 (3)0.003 (2)0.003 (3)0.013 (2)
O20.041 (3)0.027 (3)0.051 (4)0.009 (3)0.010 (3)0.016 (3)
O30.053 (4)0.060 (4)0.052 (4)0.031 (4)−0.009 (3)−0.001 (3)
O40.127 (9)0.126 (9)0.097 (7)0.085 (7)−0.009 (6)−0.034 (6)
O50.122 (9)0.244 (14)0.055 (6)0.098 (9)−0.008 (6)0.017 (7)
N10.035 (4)0.022 (3)0.030 (3)0.007 (3)0.011 (3)0.008 (3)
N20.030 (3)0.022 (3)0.031 (3)0.006 (3)0.007 (3)0.008 (3)
N30.031 (3)0.019 (3)0.025 (3)0.009 (3)0.003 (3)0.004 (2)
N40.038 (4)0.029 (4)0.036 (4)0.011 (3)0.016 (3)0.010 (3)
N50.033 (4)0.033 (4)0.039 (4)0.010 (3)0.019 (3)0.004 (3)
N60.057 (5)0.062 (5)0.037 (4)0.029 (4)0.006 (4)0.005 (4)
C10.022 (4)0.025 (4)0.028 (4)0.002 (3)−0.002 (3)0.007 (3)
C20.042 (5)0.027 (4)0.032 (4)0.014 (4)0.011 (4)0.010 (3)
C30.036 (5)0.042 (5)0.027 (4)0.014 (4)0.010 (3)0.006 (3)
C40.036 (5)0.050 (5)0.027 (4)0.007 (4)0.007 (4)0.015 (4)
C50.033 (4)0.033 (4)0.040 (5)−0.003 (4)0.002 (4)0.019 (4)
C60.022 (4)0.030 (4)0.028 (4)0.004 (3)0.000 (3)0.005 (3)
C70.025 (4)0.024 (4)0.024 (4)0.000 (3)0.001 (3)0.004 (3)
C80.009 (3)0.027 (4)0.020 (3)0.002 (3)−0.007 (3)0.002 (3)
C90.032 (4)0.022 (4)0.045 (5)0.000 (3)−0.005 (4)0.012 (3)
C100.050 (5)0.023 (4)0.039 (5)0.018 (4)0.011 (4)−0.001 (3)
C110.034 (4)0.034 (4)0.031 (4)0.009 (4)0.013 (3)0.001 (3)
C120.029 (4)0.019 (4)0.030 (4)0.010 (3)0.003 (3)0.003 (3)
C130.028 (4)0.029 (4)0.029 (4)0.005 (3)0.002 (3)0.005 (3)
C140.034 (5)0.027 (4)0.042 (5)0.004 (3)0.005 (4)0.011 (4)
C150.027 (4)0.049 (5)0.048 (5)0.003 (4)0.018 (4)0.015 (4)
C160.038 (5)0.060 (6)0.047 (5)−0.003 (4)0.012 (4)0.029 (5)
C170.068 (7)0.047 (6)0.046 (6)−0.006 (5)0.008 (5)0.013 (5)
C180.070 (7)0.032 (5)0.054 (6)0.016 (5)0.027 (5)0.014 (4)
C190.033 (4)0.032 (4)0.035 (4)0.009 (4)0.012 (4)0.007 (3)
C200.026 (4)0.019 (4)0.031 (4)0.003 (3)0.012 (3)0.002 (3)
C210.036 (5)0.036 (5)0.041 (5)−0.005 (4)0.004 (4)0.012 (4)
C220.032 (4)0.035 (5)0.036 (5)0.000 (4)0.006 (4)−0.001 (4)

Geometric parameters (Å, °)

Pb1—O12.411 (5)C4—C51.364 (11)
Pb1—N12.541 (6)C4—H40.9300
Pb1—N32.548 (6)C5—C61.380 (11)
Pb1—N42.583 (6)C5—H5A0.9300
Pb1—O32.749 (6)C7—C81.441 (10)
Pb1—O22.914 (6)C8—C91.381 (10)
Pb1—O2i2.958 (5)C9—C101.397 (11)
Pb1—O43.185 (10)C9—H90.9300
O1—C201.275 (9)C10—C111.378 (11)
O2—C201.231 (9)C10—H100.9300
O3—N61.217 (9)C11—C121.393 (10)
O4—N61.216 (11)C11—H110.9300
O5—N61.200 (11)C12—C131.445 (11)
N1—C71.317 (9)C14—C151.389 (11)
N1—C11.369 (9)C14—C191.389 (11)
N2—C71.330 (9)C15—C161.359 (12)
N2—C61.399 (9)C15—H150.9300
N2—H20.8600C16—C171.405 (13)
N3—C121.358 (9)C16—H160.9300
N3—C81.367 (9)C17—C181.356 (13)
N4—C131.327 (9)C17—H170.9300
N4—C191.382 (10)C18—C191.394 (12)
N5—C131.356 (9)C18—H180.9300
N5—C141.379 (10)C20—C211.513 (11)
N5—H50.8600C21—C221.516 (11)
C1—C21.386 (10)C21—H21A0.9700
C1—C61.399 (10)C21—H21B0.9700
C2—C31.378 (11)C22—C22ii1.519 (14)
C2—H2A0.9300C22—H22A0.9700
C3—C41.408 (11)C22—H22B0.9700
C3—H30.9300
O1—Pb1—N181.15 (19)C3—C4—H4119.3
O1—Pb1—N376.12 (18)C4—C5—C6116.6 (7)
N1—Pb1—N365.32 (19)C4—C5—H5A121.7
O1—Pb1—N483.9 (2)C6—C5—H5A121.7
N1—Pb1—N4129.70 (19)C5—C6—C1123.5 (7)
N3—Pb1—N464.51 (19)C5—C6—N2131.7 (7)
O1—Pb1—O3142.75 (18)C1—C6—N2104.8 (6)
N1—Pb1—O384.8 (2)N1—C7—N2112.8 (6)
N3—Pb1—O366.66 (19)N1—C7—C8123.6 (7)
N4—Pb1—O378.9 (2)N2—C7—C8123.6 (7)
O1—Pb1—O247.51 (16)N3—C8—C9120.6 (6)
N1—Pb1—O2121.65 (18)N3—C8—C7114.8 (6)
N3—Pb1—O2114.54 (17)C9—C8—C7124.5 (7)
N4—Pb1—O277.49 (18)C8—C9—C10119.2 (7)
O3—Pb1—O2152.3 (2)C8—C9—H9120.4
O1—Pb1—O2i89.14 (17)C10—C9—H9120.4
N1—Pb1—O2i87.79 (17)C11—C10—C9120.6 (7)
N3—Pb1—O2i150.76 (17)C11—C10—H10119.7
N4—Pb1—O2i139.77 (18)C9—C10—H10119.7
O3—Pb1—O2i124.72 (17)C10—C11—C12118.0 (7)
O2—Pb1—O2i68.94 (18)C10—C11—H11121.0
O1—Pb1—O4167.8 (3)C12—C11—H11121.0
N1—Pb1—O488.3 (3)N3—C12—C11121.9 (7)
N3—Pb1—O4105.0 (2)N3—C12—C13114.9 (6)
N4—Pb1—O4107.6 (2)C11—C12—C13123.2 (7)
O3—Pb1—O440.80 (19)N4—C13—N5111.9 (7)
O2—Pb1—O4137.4 (2)N4—C13—C12122.8 (7)
O2i—Pb1—O484.36 (19)N5—C13—C12125.2 (7)
C20—O1—Pb1106.6 (5)N5—C14—C15131.9 (8)
C20—O2—Pb183.5 (4)N5—C14—C19105.6 (7)
N6—O3—Pb1105.7 (5)C15—C14—C19122.4 (8)
N6—O4—Pb184.3 (6)C16—C15—C14116.2 (8)
C7—N1—C1106.2 (6)C16—C15—H15121.9
C7—N1—Pb1116.8 (4)C14—C15—H15121.9
C1—N1—Pb1136.9 (5)C15—C16—C17122.1 (8)
C7—N2—C6107.1 (6)C15—C16—H16118.9
C7—N2—H2126.5C17—C16—H16118.9
C6—N2—H2126.5C18—C17—C16121.6 (9)
C12—N3—C8119.6 (6)C18—C17—H17119.2
C12—N3—Pb1120.8 (5)C16—C17—H17119.2
C8—N3—Pb1119.3 (4)C17—C18—C19117.3 (9)
C13—N4—C19105.6 (6)C17—C18—H18121.3
C13—N4—Pb1116.7 (5)C19—C18—H18121.3
C19—N4—Pb1137.6 (5)N4—C19—C14109.5 (7)
C13—N5—C14107.4 (6)N4—C19—C18130.0 (7)
C13—N5—H5126.3C14—C19—C18120.4 (8)
C14—N5—H5126.3O2—C20—O1122.3 (7)
O5—N6—O4120.5 (10)O2—C20—C21121.4 (7)
O5—N6—O3119.2 (9)O1—C20—C21116.4 (7)
O4—N6—O3120.1 (9)C20—C21—C22114.5 (7)
N1—C1—C2131.7 (7)C20—C21—H21A108.6
N1—C1—C6109.1 (6)C22—C21—H21A108.6
C2—C1—C6119.2 (7)C20—C21—H21B108.6
C3—C2—C1118.0 (8)C22—C21—H21B108.6
C3—C2—H2A121.0H21A—C21—H21B107.6
C1—C2—H2A121.0C21—C22—C22ii111.7 (8)
C2—C3—C4121.4 (7)C21—C22—H22A109.3
C2—C3—H3119.3C22ii—C22—H22A109.3
C4—C3—H3119.3C21—C22—H22B109.3
C5—C4—C3121.3 (7)C22ii—C22—H22B109.3
C5—C4—H4119.3H22A—C22—H22B107.9
N1—Pb1—O1—C20151.2 (5)Pb1—N1—C1—C27.0 (13)
N3—Pb1—O1—C20−142.2 (5)C7—N1—C1—C6−0.2 (8)
N4—Pb1—O1—C20−77.0 (5)Pb1—N1—C1—C6−175.5 (5)
O3—Pb1—O1—C20−139.6 (5)N1—C1—C2—C3178.9 (8)
O2—Pb1—O1—C201.6 (4)C6—C1—C2—C31.6 (11)
O2i—Pb1—O1—C2063.3 (5)C1—C2—C3—C4−0.5 (12)
O4—Pb1—O1—C20120.9 (10)C2—C3—C4—C5−0.3 (13)
O1—Pb1—O2—C20−1.6 (4)C3—C4—C5—C60.1 (12)
N1—Pb1—O2—C20−37.5 (5)C4—C5—C6—C11.0 (12)
N3—Pb1—O2—C2037.6 (5)C4—C5—C6—N2−177.8 (8)
N4—Pb1—O2—C2091.7 (4)N1—C1—C6—C5−179.8 (7)
O3—Pb1—O2—C20123.7 (5)C2—C1—C6—C5−1.9 (12)
O2i—Pb1—O2—C20−110.9 (5)N1—C1—C6—N2−0.7 (8)
O4—Pb1—O2—C20−165.8 (4)C2—C1—C6—N2177.2 (7)
O1—Pb1—O3—N6−178.2 (5)C7—N2—C6—C5−179.7 (8)
N1—Pb1—O3—N6−110.1 (6)C7—N2—C6—C11.3 (8)
N3—Pb1—O3—N6−175.4 (7)C1—N1—C7—N21.1 (9)
N4—Pb1—O3—N6117.7 (6)Pb1—N1—C7—N2177.5 (5)
O2—Pb1—O3—N685.9 (7)C1—N1—C7—C8179.9 (7)
O2i—Pb1—O3—N6−26.4 (7)Pb1—N1—C7—C8−3.7 (9)
O4—Pb1—O3—N6−16.7 (6)C6—N2—C7—N1−1.6 (9)
O1—Pb1—O4—N6130.1 (9)C6—N2—C7—C8179.7 (6)
N1—Pb1—O4—N6100.2 (8)C12—N3—C8—C90.7 (10)
N3—Pb1—O4—N636.4 (8)Pb1—N3—C8—C9−173.1 (5)
N4—Pb1—O4—N6−31.1 (8)C12—N3—C8—C7178.2 (6)
O3—Pb1—O4—N616.2 (6)Pb1—N3—C8—C74.4 (8)
O2—Pb1—O4—N6−121.7 (7)N1—C7—C8—N3−0.4 (10)
O2i—Pb1—O4—N6−171.8 (8)N2—C7—C8—N3178.2 (6)
O1—Pb1—N1—C782.8 (5)N1—C7—C8—C9177.0 (7)
N3—Pb1—N1—C74.0 (5)N2—C7—C8—C9−4.4 (11)
N4—Pb1—N1—C78.3 (6)N3—C8—C9—C100.8 (11)
O3—Pb1—N1—C7−62.6 (5)C7—C8—C9—C10−176.4 (7)
O2—Pb1—N1—C7108.7 (5)C8—C9—C10—C11−1.8 (12)
O2i—Pb1—N1—C7172.2 (5)C9—C10—C11—C121.2 (12)
O4—Pb1—N1—C7−103.4 (5)C8—N3—C12—C11−1.3 (11)
O1—Pb1—N1—C1−102.3 (7)Pb1—N3—C12—C11172.4 (6)
N3—Pb1—N1—C1179.0 (8)C8—N3—C12—C13179.1 (6)
N4—Pb1—N1—C1−176.8 (6)Pb1—N3—C12—C13−7.3 (9)
O3—Pb1—N1—C1112.3 (7)C10—C11—C12—N30.4 (12)
O2—Pb1—N1—C1−76.3 (7)C10—C11—C12—C13180.0 (8)
O2i—Pb1—N1—C1−12.8 (7)C19—N4—C13—N50.0 (9)
O4—Pb1—N1—C171.6 (7)Pb1—N4—C13—N5−176.3 (5)
O1—Pb1—N3—C1295.3 (6)C19—N4—C13—C12176.8 (7)
N1—Pb1—N3—C12−178.2 (6)Pb1—N4—C13—C120.5 (10)
N4—Pb1—N3—C125.5 (5)C14—N5—C13—N4−0.6 (9)
O3—Pb1—N3—C12−83.0 (6)C14—N5—C13—C12−177.2 (7)
O2—Pb1—N3—C1266.7 (6)N3—C12—C13—N44.4 (11)
O2i—Pb1—N3—C12157.1 (5)C11—C12—C13—N4−175.2 (8)
O4—Pb1—N3—C12−97.2 (6)N3—C12—C13—N5−179.3 (7)
O1—Pb1—N3—C8−91.0 (5)C11—C12—C13—N51.1 (12)
N1—Pb1—N3—C8−4.5 (5)C13—N5—C14—C15177.1 (9)
N4—Pb1—N3—C8179.2 (5)C13—N5—C14—C190.8 (9)
O3—Pb1—N3—C890.7 (5)N5—C14—C15—C16−174.5 (9)
O2—Pb1—N3—C8−119.6 (5)C19—C14—C15—C161.2 (13)
O2i—Pb1—N3—C8−29.2 (7)C14—C15—C16—C17−1.8 (14)
O4—Pb1—N3—C876.5 (5)C15—C16—C17—C181.9 (16)
O1—Pb1—N4—C13−80.3 (6)C16—C17—C18—C19−1.2 (16)
N1—Pb1—N4—C13−7.2 (7)C13—N4—C19—C140.5 (9)
N3—Pb1—N4—C13−2.9 (5)Pb1—N4—C19—C14175.6 (6)
O3—Pb1—N4—C1366.4 (6)C13—N4—C19—C18−176.0 (9)
O2—Pb1—N4—C13−128.1 (6)Pb1—N4—C19—C18−0.9 (15)
O2i—Pb1—N4—C13−161.8 (5)N5—C14—C19—N4−0.8 (9)
O4—Pb1—N4—C1395.7 (6)C15—C14—C19—N4−177.5 (8)
O1—Pb1—N4—C19104.9 (8)N5—C14—C19—C18176.1 (8)
N1—Pb1—N4—C19178.1 (7)C15—C14—C19—C18−0.6 (13)
N3—Pb1—N4—C19−177.6 (9)C17—C18—C19—N4176.8 (9)
O3—Pb1—N4—C19−108.3 (8)C17—C18—C19—C140.6 (14)
O2—Pb1—N4—C1957.2 (8)Pb1—O2—C20—O12.6 (7)
O2i—Pb1—N4—C1923.5 (9)Pb1—O2—C20—C21−178.5 (7)
O4—Pb1—N4—C19−79.0 (8)Pb1—O1—C20—O2−3.2 (8)
Pb1—O4—N6—O5156.9 (12)Pb1—O1—C20—C21177.8 (5)
Pb1—O4—N6—O3−28.4 (10)O2—C20—C21—C2239.6 (10)
Pb1—O3—N6—O5−150.5 (10)O1—C20—C21—C22−141.5 (7)
Pb1—O3—N6—O434.7 (12)C20—C21—C22—C22ii64.3 (12)
C7—N1—C1—C2−177.7 (8)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N2—H2···O1iii0.861.952.744 (8)152
N5—H5···O3iv0.862.102.891 (9)153

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5131).

References

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  • Westrip, S. P. (2009). publCIF In preparation.

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