supplementary materials


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

ci2964 scheme

Acta Cryst. (2009). E65, m1544    [ doi:10.1107/S1600536809046455 ]

catena-Poly[[(1,10-phenanthroline-5,6-dione-[kappa]2N,N')lead(II)]-[mu]-terephthalato-[kappa]2O1:O4\]

F.-D. Cong, F.-Y. Yu, Z. Wei and S. W. Ng

Abstract top

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 [psi]-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 [psi]-dodecahedron.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 2009).

Figures top
[Figure 1] 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.
[Figure 2] 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.
catena-Poly[[(1,10-phenanthroline-5,6-dione- κ2N,N')lead(II)]-µ-terephthalato-κ2O1:O4] top
Crystal data top
[Pb(C8H4O4)(C12H6N2O2)]F(000) = 1096
Mr = 581.49Dx = 2.334 Mg m−3
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 mm−1
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 top
Bruker APEXII area-detector
diffractometer		3233 independent reflections
Radiation source: fine-focus sealed tube2369 reflections with I > 2σ(I)
graphiteRint = 0.036
φ 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 top
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 = 1.00 w = 1/[σ2(Fo2) + (0.0491P)2]
where P = (Fo2 + 2Fc2)/3
3233 reflections(Δ/σ)max = 0.001
262 parametersΔρmax = 1.94 e Å−3
0 restraintsΔρmin = −0.95 e Å−3
Crystal data top
[Pb(C8H4O4)(C12H6N2O2)]V = 1654.8 (5) Å3
Mr = 581.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.428 (1) ŵ = 10.24 mm−1
b = 15.187 (1) ÅT = 295 K
c = 11.478 (3) Å0.24 × 0.22 × 0.20 mm
β = 114.444 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer		3233 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		2369 reflections with I > 2σ(I)
Tmin = 0.193, Tmax = 0.234Rint = 0.036
8875 measured reflectionsθmax = 26.0°
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.086Δρmax = 1.94 e Å−3
S = 1.00Δρmin = −0.95 e Å−3
3233 reflectionsAbsolute structure: ?
262 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
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) top
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, °) top
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.
Table 1
Selected geometric parameters (Å) top
Pb1—O12.410 (6)Pb1—O4ii2.910 (5)
Pb1—O23.211 (5)Pb1—N12.535 (6)
Pb1—O2i3.176 (6)Pb1—N22.626 (6)
Pb1—O3ii2.301 (5)
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+2, y+1/2, −z+3/2.
Acknowledgements top

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

references
References top

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

Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

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

Tan, Y.-X., Meng, F.-Y., Wu, M.-C. & Zeng, M.-H. (2009). J. Mol. Struct. 928, 176–181.

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