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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): m1544.
Published online 2009 November 7. doi:  10.1107/S1600536809046455
PMCID: PMC2971762

catena-Poly[[(1,10-phenanthroline-5,6-dione-κ2 N,N′)lead(II)]-μ-terephthalato-κ2 O 1:O 4]

Abstract

The PbII atom in the polymeric title compound, [Pb(C8H4O4)(C12H6N2O2)]n, is chelated by the N-heterocycle, and adjacent atoms are bridged by rigid terephthalate dianions into a linear chain. The PbII atom is stereochemically active in a ψ-square-pyramidal coordination geometry in which the lone-pair electrons occupy a basal site. When three other weaker Pb(...)O inter­actions are considered, the geometry is a ψ-dodeca­hedron.

Related literature

For the crystal structure of lead(II) terephthalate, see: Tan et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-m1544-scheme1.jpg

Experimental

Crystal data

  • [Pb(C8H4O4)(C12H6N2O2)]
  • M r = 581.49
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-m1544-efi3.jpg
  • a = 10.428 (1) Å
  • b = 15.187 (1) Å
  • c = 11.478 (3) Å
  • β = 114.444 (1)°
  • V = 1654.8 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 10.24 mm−1
  • T = 295 K
  • 0.24 × 0.22 × 0.20 mm

Data collection

  • Bruker APEXII area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.193, T max = 0.234
  • 8875 measured reflections
  • 3233 independent reflections
  • 2369 reflections with I > 2σ(I)
  • R int = 0.036

Refinement

  • R[F 2 > 2σ(F 2)] = 0.033
  • wR(F 2) = 0.086
  • S = 1.00
  • 3233 reflections
  • 262 parameters
  • H-atom parameters constrained
  • Δρmax = 1.94 e Å−3
  • Δρmin = −0.95 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: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2009 [triangle]).

Table 1
Selected bond lengths (Å)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046455/ci2964sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046455/ci2964Isup2.hkl

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

Acknowledgments

The authors thank Tianjin Agricultural University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

Lead nitrate (0.5 mmol, 0.166 g), terephthalic acid (0.5 mmol, 0.083 g) and phenanthrene-9,10-dione (0.5 mmol, 0.104 g) in water (12 ml) were heated at 443 K for 3 days in a Teflon-lined, stainless-steel Parr bomb. The bomb was slowly cooled to room temperature after which crystals were collected in 40% yield.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C-H = 0.93 Å) and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C). The final difference Fourier map had one peak in the vicinity of the lead atom (0.95 Å from Pb1) but was otherwise diffuse.

Figures

Fig. 1.
Displacement ellipsoid plot (Barbour, 2001) of a part of the polymeric Pb(C8H4O2)(C12H6N2O2) chain at the 70% probability level; H atoms are drawn as spheres of arbitrary radius. Symmetry code: (i) 2-x, 1/2+y, 3/2-z.
Fig. 2.
Detail of the polyhedron surrounding the lead atom. Symmetry codes: (i) 1-x, 1-y, 1-z; (ii) 2-x, 1/2+y, 3/2-z.

Crystal data

[Pb(C8H4O4)(C12H6N2O2)]F(000) = 1096
Mr = 581.49Dx = 2.334 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2807 reflections
a = 10.428 (1) Åθ = 2.4–25.4°
b = 15.187 (1) ŵ = 10.24 mm1
c = 11.478 (3) ÅT = 295 K
β = 114.444 (1)°Block, yellow
V = 1654.8 (5) Å30.24 × 0.22 × 0.20 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer3233 independent reflections
Radiation source: fine-focus sealed tube2369 reflections with I > 2σ(I)
graphiteRint = 0.036
[var phi] and ω scansθmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→7
Tmin = 0.193, Tmax = 0.234k = −18→18
8875 measured reflectionsl = −12→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)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.0491P)2] where P = (Fo2 + 2Fc2)/3
3233 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 1.94 e Å3
0 restraintsΔρmin = −0.95 e Å3

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

xyzUiso*/Ueq
Pb10.60601 (3)0.525108 (19)0.39442 (2)0.02978 (11)
O10.8123 (7)0.4460 (4)0.5353 (5)0.0548 (17)
O20.7155 (6)0.4344 (4)0.6715 (5)0.0489 (15)
O31.2513 (6)0.1473 (4)1.0397 (5)0.0434 (14)
O41.3459 (6)0.1510 (4)0.9005 (5)0.0414 (14)
O50.7884 (6)0.5551 (4)−0.1400 (5)0.0396 (14)
O60.5419 (6)0.6582 (4)−0.2269 (4)0.0401 (14)
N10.7358 (7)0.4976 (4)0.2537 (6)0.0313 (15)
N20.5139 (6)0.6109 (4)0.1764 (5)0.0273 (14)
C10.8093 (8)0.4176 (5)0.6363 (6)0.0274 (16)
C20.9298 (7)0.3592 (5)0.7180 (6)0.0269 (16)
C30.9398 (8)0.3284 (5)0.8348 (6)0.0328 (18)
H30.87320.34560.86470.039*
C41.0481 (8)0.2719 (5)0.9082 (6)0.0307 (17)
H41.05300.25140.98620.037*
C51.1492 (8)0.2459 (4)0.8653 (6)0.0250 (15)
C61.1423 (8)0.2799 (5)0.7518 (6)0.0266 (16)
H61.21070.26420.72340.032*
C71.0367 (8)0.3362 (4)0.6798 (6)0.0279 (17)
H71.03590.35950.60460.033*
C81.2578 (8)0.1772 (5)0.9386 (7)0.0274 (16)
C90.8489 (9)0.4464 (5)0.2881 (7)0.039 (2)
H90.88070.41980.36810.047*
C100.9226 (8)0.4296 (6)0.2157 (7)0.0373 (19)
H101.00070.39270.24600.045*
C110.8796 (8)0.4678 (5)0.0993 (7)0.0353 (18)
H110.92840.45760.04870.042*
C120.7620 (7)0.5226 (5)0.0555 (6)0.0253 (15)
C130.7110 (8)0.5659 (5)−0.0684 (6)0.0291 (17)
C140.5958 (8)0.6182 (5)−0.1084 (6)0.0294 (16)
C150.5252 (8)0.6348 (5)−0.0279 (6)0.0275 (16)
C160.4105 (8)0.6930 (5)−0.0603 (7)0.0371 (19)
H160.37450.7208−0.13970.044*
C170.3523 (9)0.7087 (5)0.0235 (7)0.041 (2)
H170.27780.74810.00270.049*
C180.4045 (8)0.6657 (5)0.1401 (7)0.0354 (19)
H180.36140.67540.19560.042*
C190.5741 (7)0.5947 (4)0.0952 (6)0.0230 (15)
C200.6907 (7)0.5364 (4)0.1342 (6)0.0237 (15)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pb10.02839 (17)0.03876 (18)0.02215 (15)−0.00225 (15)0.01043 (12)0.00065 (13)
O10.044 (4)0.090 (5)0.032 (3)0.022 (3)0.018 (3)0.020 (3)
O20.045 (4)0.067 (4)0.043 (3)0.017 (3)0.026 (3)0.012 (3)
O30.054 (4)0.050 (3)0.032 (3)0.017 (3)0.024 (3)0.012 (3)
O40.039 (3)0.055 (4)0.035 (3)0.011 (3)0.020 (3)0.009 (3)
O50.037 (3)0.060 (4)0.031 (3)0.000 (3)0.025 (3)0.000 (3)
O60.040 (3)0.058 (4)0.022 (3)0.007 (3)0.012 (3)0.012 (2)
N10.031 (4)0.031 (3)0.030 (3)0.007 (3)0.012 (3)0.007 (2)
N20.029 (4)0.030 (3)0.024 (3)0.000 (3)0.013 (3)−0.001 (2)
C10.030 (4)0.031 (4)0.020 (4)−0.003 (3)0.010 (3)−0.005 (3)
C20.023 (4)0.031 (4)0.020 (4)0.000 (3)0.002 (3)−0.001 (3)
C30.032 (4)0.048 (5)0.019 (4)0.006 (4)0.011 (3)0.002 (3)
C40.035 (4)0.038 (4)0.019 (4)0.001 (4)0.011 (3)0.007 (3)
C50.030 (4)0.023 (4)0.023 (4)−0.005 (3)0.012 (3)−0.004 (3)
C60.028 (4)0.036 (4)0.019 (3)0.001 (3)0.013 (3)0.001 (3)
C70.032 (4)0.030 (4)0.021 (4)0.000 (3)0.011 (3)0.004 (3)
C80.028 (4)0.029 (4)0.025 (4)−0.005 (3)0.012 (3)−0.004 (3)
C90.042 (5)0.044 (5)0.028 (4)0.013 (4)0.010 (4)0.005 (3)
C100.031 (4)0.049 (5)0.031 (4)0.007 (4)0.012 (4)0.006 (4)
C110.035 (5)0.038 (4)0.038 (4)0.001 (4)0.020 (4)−0.003 (4)
C120.024 (4)0.031 (4)0.022 (3)0.000 (4)0.011 (3)−0.007 (3)
C130.030 (4)0.035 (4)0.023 (4)−0.005 (4)0.012 (3)−0.010 (3)
C140.031 (4)0.035 (4)0.020 (3)−0.009 (4)0.009 (3)−0.002 (3)
C150.023 (4)0.034 (4)0.021 (4)−0.005 (3)0.005 (3)−0.001 (3)
C160.034 (5)0.043 (5)0.031 (4)0.008 (4)0.010 (4)0.008 (4)
C170.041 (5)0.042 (5)0.036 (5)0.011 (4)0.014 (4)0.012 (4)
C180.033 (5)0.038 (4)0.037 (5)0.002 (4)0.016 (4)−0.008 (3)
C190.024 (4)0.023 (3)0.020 (3)−0.007 (3)0.007 (3)−0.003 (3)
C200.020 (4)0.030 (4)0.017 (3)−0.005 (3)0.002 (3)−0.005 (3)

Geometric parameters (Å, °)

Pb1—O12.410 (6)C5—C61.375 (9)
Pb1—O23.211 (5)C5—C81.514 (10)
Pb1—O2i3.176 (6)C6—C71.369 (9)
Pb1—O3ii2.301 (5)C6—H60.93
Pb1—O4ii2.910 (5)C7—H70.93
Pb1—N12.535 (6)C9—C101.369 (11)
Pb1—N22.626 (6)C9—H90.93
O1—C11.249 (8)C10—C111.352 (10)
O2—C11.230 (9)C10—H100.93
O3—C81.273 (8)C11—C121.392 (10)
O4—C81.235 (9)C11—H110.93
O5—C131.380 (8)C12—C201.403 (9)
O6—C141.379 (8)C12—C131.453 (10)
N1—C91.329 (10)C13—C141.352 (10)
N1—C201.384 (9)C14—C151.423 (10)
N2—C181.332 (9)C15—C161.408 (10)
N2—C191.345 (8)C15—C191.425 (9)
C1—C21.507 (10)C16—C171.354 (10)
C2—C31.382 (9)C16—H160.93
C2—C71.401 (10)C17—C181.383 (10)
C3—C41.390 (10)C17—H170.93
C3—H30.93C18—H180.93
C4—C51.392 (10)C19—C201.419 (9)
C4—H40.93
O3ii—Pb1—O184.5 (2)C7—C6—C5121.3 (7)
O3ii—Pb1—N184.2 (2)C7—C6—H6119.3
O1—Pb1—N177.40 (19)C5—C6—H6119.3
O3ii—Pb1—N281.07 (18)C6—C7—C2120.8 (6)
O1—Pb1—N2139.46 (19)C6—C7—H7119.6
N1—Pb1—N263.61 (19)C2—C7—H7119.6
O3ii—Pb1—O4ii48.16 (16)O4—C8—O3122.4 (7)
O1—Pb1—O4ii88.69 (19)O4—C8—C5121.3 (6)
N1—Pb1—O4ii131.65 (18)O3—C8—C5116.3 (7)
N2—Pb1—O4ii108.50 (17)N1—C9—C10125.5 (7)
O3ii—Pb1—O2i113.41 (19)N1—C9—H9117.2
O1—Pb1—O2i144.83 (17)C10—C9—H9117.2
N1—Pb1—O2i132.01 (18)C11—C10—C9118.7 (8)
N2—Pb1—O2i75.11 (16)C11—C10—H10120.7
O4ii—Pb1—O2i82.96 (15)C9—C10—H10120.7
O3ii—Pb1—O295.96 (17)C10—C11—C12119.7 (7)
O1—Pb1—O243.00 (17)C10—C11—H11120.1
N1—Pb1—O2119.73 (17)C12—C11—H11120.1
N2—Pb1—O2175.42 (16)C11—C12—C20118.6 (6)
O4ii—Pb1—O266.98 (16)C11—C12—C13122.4 (6)
O2i—Pb1—O2103.09 (13)C20—C12—C13119.0 (6)
C1—O1—Pb1115.9 (5)C14—C13—O5121.6 (7)
C1—O2—Pb176.6 (4)C14—C13—C12120.9 (6)
C8—O3—Pb1iii108.4 (5)O5—C13—C12117.5 (6)
C9—N1—C20116.0 (7)C13—C14—O6122.4 (7)
C9—N1—Pb1123.3 (5)C13—C14—C15120.6 (7)
C20—N1—Pb1120.6 (5)O6—C14—C15117.0 (7)
C18—N2—C19118.9 (6)C16—C15—C14123.4 (7)
C18—N2—Pb1122.4 (5)C16—C15—C19116.6 (7)
C19—N2—Pb1118.6 (4)C14—C15—C19119.9 (7)
O2—C1—O1124.2 (7)C17—C16—C15120.3 (7)
O2—C1—C2119.3 (6)C17—C16—H16119.9
O1—C1—C2116.5 (7)C15—C16—H16119.9
C3—C2—C7117.9 (7)C16—C17—C18119.5 (8)
C3—C2—C1120.8 (7)C16—C17—H17120.3
C7—C2—C1121.2 (6)C18—C17—H17120.3
C2—C3—C4120.8 (7)N2—C18—C17122.7 (7)
C2—C3—H3119.6N2—C18—H18118.7
C4—C3—H3119.6C17—C18—H18118.7
C3—C4—C5120.4 (6)N2—C19—C20118.7 (6)
C3—C4—H4119.8N2—C19—C15122.0 (6)
C5—C4—H4119.8C20—C19—C15119.2 (6)
C6—C5—C4118.5 (7)N1—C20—C12121.4 (6)
C6—C5—C8121.3 (7)N1—C20—C19118.3 (6)
C4—C5—C8120.1 (6)C12—C20—C19120.2 (6)
O3ii—Pb1—O1—C1108.0 (6)Pb1iii—O3—C8—O4−10.9 (9)
N1—Pb1—O1—C1−166.8 (6)Pb1iii—O3—C8—C5167.9 (5)
N2—Pb1—O1—C1177.4 (5)C6—C5—C8—O41.9 (11)
O4ii—Pb1—O1—C159.9 (6)C4—C5—C8—O4177.7 (7)
O2i—Pb1—O1—C1−15.9 (8)C6—C5—C8—O3−177.0 (7)
O2—Pb1—O1—C13.2 (5)C4—C5—C8—O3−1.2 (10)
O3ii—Pb1—O2—C1−78.4 (5)C20—N1—C9—C100.1 (12)
O1—Pb1—O2—C1−3.0 (5)Pb1—N1—C9—C10−179.9 (7)
N1—Pb1—O2—C18.3 (5)N1—C9—C10—C110.4 (13)
O4ii—Pb1—O2—C1−117.8 (5)C9—C10—C11—C12−0.3 (12)
O2i—Pb1—O2—C1165.8 (5)C10—C11—C12—C20−0.2 (11)
O3ii—Pb1—N1—C993.9 (6)C10—C11—C12—C13179.7 (7)
O1—Pb1—N1—C98.2 (6)C11—C12—C13—C14179.5 (7)
N2—Pb1—N1—C9176.8 (7)C20—C12—C13—C14−0.6 (11)
O4ii—Pb1—N1—C984.9 (6)C11—C12—C13—O5−3.7 (10)
O2i—Pb1—N1—C9−149.6 (6)C20—C12—C13—O5176.2 (6)
O2—Pb1—N1—C90.3 (7)O5—C13—C14—O65.3 (11)
O3ii—Pb1—N1—C20−86.2 (5)C12—C13—C14—O6−178.0 (6)
O1—Pb1—N1—C20−171.9 (6)O5—C13—C14—C15−174.1 (6)
N2—Pb1—N1—C20−3.3 (5)C12—C13—C14—C152.6 (11)
O4ii—Pb1—N1—C20−95.2 (5)C13—C14—C15—C16175.8 (7)
O2i—Pb1—N1—C2030.3 (6)O6—C14—C15—C16−3.7 (11)
O2—Pb1—N1—C20−179.7 (5)C13—C14—C15—C19−1.4 (11)
O3ii—Pb1—N2—C18−92.5 (6)O6—C14—C15—C19179.2 (6)
O1—Pb1—N2—C18−163.1 (5)C14—C15—C16—C17−177.0 (8)
N1—Pb1—N2—C18179.6 (6)C19—C15—C16—C170.2 (11)
O4ii—Pb1—N2—C18−52.4 (6)C15—C16—C17—C18−1.4 (13)
O2i—Pb1—N2—C1824.8 (5)C19—N2—C18—C17−1.9 (11)
O3ii—Pb1—N2—C1991.7 (5)Pb1—N2—C18—C17−177.6 (6)
O1—Pb1—N2—C1921.1 (6)C16—C17—C18—N22.3 (13)
N1—Pb1—N2—C193.8 (5)C18—N2—C19—C20180.0 (6)
O4ii—Pb1—N2—C19131.8 (5)Pb1—N2—C19—C20−4.1 (8)
O2i—Pb1—N2—C19−151.0 (5)C18—N2—C19—C150.5 (10)
Pb1—O2—C1—O14.8 (7)Pb1—N2—C19—C15176.5 (5)
Pb1—O2—C1—C2−175.3 (6)C16—C15—C19—N20.3 (10)
Pb1—O1—C1—O2−6.9 (10)C14—C15—C19—N2177.6 (6)
Pb1—O1—C1—C2173.2 (5)C16—C15—C19—C20−179.1 (6)
O2—C1—C2—C3−3.5 (11)C14—C15—C19—C20−1.8 (10)
O1—C1—C2—C3176.5 (7)C9—N1—C20—C12−0.7 (10)
O2—C1—C2—C7178.1 (7)Pb1—N1—C20—C12179.4 (5)
O1—C1—C2—C7−1.9 (10)C9—N1—C20—C19−177.3 (7)
C7—C2—C3—C4−3.9 (11)Pb1—N1—C20—C192.7 (8)
C1—C2—C3—C4177.6 (7)C11—C12—C20—N10.7 (10)
C2—C3—C4—C50.5 (11)C13—C12—C20—N1−179.2 (6)
C3—C4—C5—C62.4 (10)C11—C12—C20—C19177.3 (6)
C3—C4—C5—C8−173.6 (7)C13—C12—C20—C19−2.6 (10)
C4—C5—C6—C7−1.7 (10)N2—C19—C20—N11.0 (9)
C8—C5—C6—C7174.2 (6)C15—C19—C20—N1−179.5 (6)
C5—C6—C7—C2−1.8 (11)N2—C19—C20—C12−175.7 (6)
C3—C2—C7—C64.6 (11)C15—C19—C20—C123.8 (9)
C1—C2—C7—C6−177.0 (6)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI2964).

References

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