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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): m963.
Published online 2010 July 17. doi:  10.1107/S1600536810027777
PMCID: PMC3007209

Bis(μ-quinoline-2-carboxyl­ato)-κ3 N,O:O3 O:N,O-bis­[(acetato-κ2 O,O′)(methanol-κO)lead(II)]

Abstract

The dinuclear title compound, [Pb2(C10H6NO2)2(CH3COO)2(CH3OH)2], lies across an inversion center. The methanol-coordinated PbII atom is chelated by the acetate anion as well as by the quinoline-2-carboxyl­ate anion. One O atom of the quinoline-2-carboxyl­ate anion bridges two symmetry-related PbII atoms, forming the dinuclear compound. Aside from the six atoms connected to the PbII atom by regular coordination bonds, the structure features a long Pb(...)O inter­action [3.145 (3) Å] that gives rise to a distorted Ψ-square-anti­prismatic geometry at the metal center. The H atom of the methanol is hydrogen bonded to an O atom of the acetate.

Related literature

For a related structure, see: Mohammadnezhad et al. (2010 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m963-scheme1.jpg

Experimental

Crystal data

  • [Pb2(C10H6NO2)2(C2H3O2)2(CH4O)2]
  • M r = 940.87
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m963-efi1.jpg
  • a = 7.3197 (3) Å
  • b = 8.3065 (4) Å
  • c = 23.3247 (10) Å
  • β = 90.397 (1)°
  • V = 1418.13 (11) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 11.91 mm−1
  • T = 100 K
  • 0.25 × 0.15 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.155, T max = 0.382
  • 13298 measured reflections
  • 3267 independent reflections
  • 3055 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.019
  • wR(F 2) = 0.049
  • S = 1.06
  • 3267 reflections
  • 186 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 1.65 e Å−3
  • Δρmin = −1.43 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [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, 2010 [triangle]).

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810027777/xu2798sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810027777/xu2798Isup2.hkl

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

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The lead(II) atom in Pb(C10H6NO2)2 is N,O-chelated by the carboxylate anions in a Ψ-trigonal bipyramidal environment; four atoms are connected to the lead atom by regular coordination bonds (Mohammadnezhad et al., 2010). This compound was synthesized by the reaction of lead acetate and quinoline-2-carboxylic acid in the presence of potassium nitrite. With potassium nitrate in place of potassium nitrite, the synthesized yielded instead dinuclear [Pb(CH4O)2(C2H3O2)2(C10H6NO2)2]2 (Scheme I, Fig. 1) in which only one of the acetate groups is replaced by the quinoline-2-carboxylate group. The methanol-coordinated lead(II) atom is chelated by the acetate anion as well as by the quinoline-2-carboxylate anion; the oxygen atom involved in chelation is also datively coordinated to the symmetry-related lead atom. When a long Pb···O2ii (ii = x - 1, y, z) interaction of 3.145 (3) Å is considered to be a bond, the geometry is a Ψ-antiprism (Fig. 2).

Experimental

Lead(II) acetate (1 mmol, 0.38 g), quinoline-2-carboxylic acid (1 mmol, 0.17 g) and potassium nitrate (1 mmol, 0.10 g) were loaded into one arm of a convection tube and both of the arms were filled slowly by methanol. The chemical-bearing arm was immersed in an oil bath kept at 333 K. Crystals were formed on the inside surface of the arm kept at ambient temperature after a weekfew days.

Refinement

Hydrogen atoms were placed in calculated positions (C–H 0.95–0.98 Å) and included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5Ueq(C).

The hydroxy H-atom was located in a difference Fourier map, and was refined with a distance restraint of O–H 0.84±0.01 Å; its temperature factor was refined.

The final difference Fourier map had a peak/hole in the vicinity of Pb1.

Figures

Fig. 1.
Thermal ellipsoid plot (Barbour, 2001) of [Pb(CH4O)2(C2H3O2)2(C10H6NO2)2]2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. The dinuclear molecule lies on a center-of-inversion.
Fig. 2.
Ψ-Square antiprismatic geometry of lead. Symmetry codes are given in Table 1.

Crystal data

[Pb2(C10H6NO2)2(C2H3O2)2(CH4O)2]F(000) = 880
Mr = 940.87Dx = 2.203 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 8885 reflections
a = 7.3197 (3) Åθ = 2.6–28.3°
b = 8.3065 (4) ŵ = 11.91 mm1
c = 23.3247 (10) ÅT = 100 K
β = 90.397 (1)°Block, colorless
V = 1418.13 (11) Å30.25 × 0.15 × 0.10 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer3267 independent reflections
Radiation source: fine-focus sealed tube3055 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.155, Tmax = 0.382k = −10→10
13298 measured reflectionsl = −30→29

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)] = 0.019Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.049H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0252P)2 + 2.8416P] where P = (Fo2 + 2Fc2)/3
3267 reflections(Δ/σ)max = 0.001
186 parametersΔρmax = 1.65 e Å3
1 restraintΔρmin = −1.43 e Å3

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

xyzUiso*/Ueq
Pb10.271223 (16)0.534286 (15)0.449130 (5)0.01353 (5)
O10.5946 (3)0.5505 (3)0.45723 (11)0.0199 (5)
O20.8654 (3)0.6518 (3)0.43362 (11)0.0240 (6)
O30.3648 (4)0.2628 (4)0.43453 (12)0.0313 (7)
O40.1736 (4)0.3174 (3)0.36464 (12)0.0294 (6)
O50.3561 (4)0.8211 (4)0.49639 (12)0.0284 (6)
H50.454 (4)0.818 (7)0.515 (2)0.043*
N10.4435 (4)0.6512 (3)0.35907 (12)0.0142 (5)
C10.7022 (4)0.6278 (4)0.42410 (14)0.0158 (7)
C20.6171 (4)0.6881 (4)0.36843 (14)0.0154 (6)
C30.7256 (5)0.7731 (5)0.32939 (16)0.0212 (7)
H30.84770.80200.33890.025*
C40.6514 (5)0.8138 (5)0.27705 (17)0.0247 (8)
H40.72300.86890.24950.030*
C50.4697 (5)0.7735 (4)0.26467 (15)0.0185 (7)
C60.3834 (5)0.8108 (5)0.21153 (16)0.0252 (8)
H60.45120.86280.18230.030*
C70.2051 (6)0.7731 (5)0.20205 (15)0.0251 (8)
H70.14890.80010.16650.030*
C80.1033 (5)0.6945 (5)0.24449 (15)0.0238 (8)
H8−0.02070.66720.23710.029*
C90.1807 (5)0.6563 (5)0.29670 (15)0.0200 (7)
H90.10990.60460.32530.024*
C100.3661 (5)0.6944 (4)0.30758 (14)0.0152 (6)
C110.2681 (5)0.2208 (5)0.39130 (15)0.0213 (7)
C120.2797 (8)0.0481 (5)0.3721 (2)0.0366 (11)
H12A0.17870.02460.34560.055*
H12B0.2717−0.02290.40560.055*
H12C0.39620.03020.35270.055*
C130.2189 (7)0.8980 (7)0.5289 (2)0.0478 (13)
H13A0.09840.86080.51600.072*
H13B0.22761.01480.52370.072*
H13C0.23560.87170.56960.072*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Pb10.00951 (7)0.01915 (8)0.01191 (7)0.00240 (5)−0.00103 (4)0.00037 (5)
O10.0138 (12)0.0310 (15)0.0148 (12)0.0017 (10)−0.0010 (9)0.0060 (10)
O20.0141 (12)0.0336 (15)0.0244 (13)−0.0003 (11)−0.0035 (10)0.0041 (11)
O30.0334 (16)0.0291 (15)0.0313 (15)0.0141 (13)−0.0169 (12)−0.0117 (12)
O40.0368 (16)0.0248 (14)0.0264 (14)0.0051 (13)−0.0145 (12)−0.0018 (12)
O50.0276 (15)0.0275 (14)0.0300 (15)0.0107 (12)−0.0137 (12)−0.0051 (12)
N10.0136 (13)0.0167 (14)0.0123 (13)0.0012 (11)−0.0002 (10)0.0004 (11)
C10.0140 (15)0.0187 (17)0.0147 (15)0.0024 (13)−0.0004 (12)−0.0010 (13)
C20.0140 (15)0.0158 (16)0.0164 (16)0.0025 (13)0.0001 (12)−0.0024 (13)
C30.0126 (16)0.0240 (18)0.0270 (19)−0.0014 (14)0.0025 (14)0.0049 (15)
C40.0204 (18)0.0270 (19)0.0269 (19)0.0012 (16)0.0050 (15)0.0112 (16)
C50.0208 (17)0.0197 (17)0.0151 (16)0.0040 (14)0.0011 (13)0.0045 (13)
C60.029 (2)0.030 (2)0.0169 (17)0.0070 (17)0.0022 (15)0.0094 (15)
C70.028 (2)0.034 (2)0.0130 (17)0.0087 (17)−0.0044 (14)0.0041 (15)
C80.0205 (18)0.033 (2)0.0176 (17)0.0043 (16)−0.0045 (14)−0.0012 (15)
C90.0181 (17)0.0249 (18)0.0171 (16)0.0017 (14)−0.0004 (13)0.0005 (14)
C100.0163 (16)0.0159 (16)0.0135 (15)0.0049 (13)0.0007 (12)−0.0016 (12)
C110.0220 (18)0.0237 (19)0.0182 (17)0.0009 (15)−0.0047 (14)0.0001 (14)
C120.055 (3)0.023 (2)0.032 (2)0.0088 (19)−0.012 (2)−0.0055 (17)
C130.047 (3)0.047 (3)0.049 (3)0.022 (3)−0.006 (2)−0.013 (3)

Geometric parameters (Å, °)

Pb1—O12.377 (3)C4—C51.400 (5)
Pb1—O1i2.490 (2)C4—H40.9500
Pb1—O2ii3.145 (3)C5—C101.421 (5)
Pb1—O32.382 (3)C5—C61.422 (5)
Pb1—O42.761 (3)C6—C71.359 (6)
Pb1—O52.696 (3)C6—H60.9500
Pb1—N12.643 (3)C7—C81.404 (5)
O1—C11.280 (4)C7—H70.9500
O2—C11.230 (4)C8—C91.376 (5)
O3—C111.276 (4)C8—H80.9500
O4—C111.226 (4)C9—C101.415 (5)
O5—C131.416 (6)C9—H90.9500
O5—H50.84 (4)C11—C121.505 (5)
N1—C21.324 (4)C12—H12A0.9800
N1—C101.372 (4)C12—H12B0.9800
C1—C21.521 (5)C12—H12C0.9800
C2—C31.403 (5)C13—H13A0.9800
C3—C41.375 (5)C13—H13B0.9800
C3—H30.9500C13—H13C0.9800
O1—Pb1—O377.17 (10)C4—C3—H3120.7
O1—Pb1—O1i63.88 (10)C2—C3—H3120.7
O3—Pb1—O1i75.27 (9)C3—C4—C5119.6 (3)
O1—Pb1—N164.02 (8)C3—C4—H4120.2
O3—Pb1—N195.46 (10)C5—C4—H4120.2
O1i—Pb1—N1127.85 (8)C4—C5—C10118.4 (3)
O1—Pb1—O571.99 (9)C4—C5—C6122.9 (3)
O3—Pb1—O5146.04 (8)C10—C5—C6118.6 (3)
O1i—Pb1—O578.63 (8)C7—C6—C5120.8 (4)
N1—Pb1—O583.70 (9)C7—C6—H6119.6
O1—Pb1—O4110.27 (9)C5—C6—H6119.6
O3—Pb1—O449.71 (8)C6—C7—C8120.4 (3)
O1i—Pb1—O4122.70 (8)C6—C7—H7119.8
N1—Pb1—O478.17 (9)C8—C7—H7119.8
O5—Pb1—O4157.89 (8)C9—C8—C7120.9 (4)
O1—Pb1—O2i105.53 (7)C9—C8—H8119.5
O3—Pb1—O2i76.37 (9)C7—C8—H8119.5
O1i—Pb1—O2i42.37 (7)C8—C9—C10119.7 (3)
N1—Pb1—O2i168.31 (8)C8—C9—H9120.2
O5—Pb1—O2i98.35 (8)C10—C9—H9120.2
O4—Pb1—O2i101.97 (8)N1—C10—C9119.2 (3)
C1—O1—Pb1126.7 (2)N1—C10—C5121.2 (3)
C1—O1—Pb1i115.5 (2)C9—C10—C5119.5 (3)
Pb1—O1—Pb1i116.12 (10)O4—C11—O3122.0 (4)
C11—O3—Pb1102.3 (2)O4—C11—C12120.4 (3)
C11—O4—Pb185.6 (2)O3—C11—C12117.6 (3)
C13—O5—Pb1117.1 (3)C11—C12—H12A109.5
C13—O5—H5110 (4)C11—C12—H12B109.5
Pb1—O5—H5112 (4)H12A—C12—H12B109.5
C2—N1—C10118.3 (3)C11—C12—H12C109.5
C2—N1—Pb1114.6 (2)H12A—C12—H12C109.5
C10—N1—Pb1126.5 (2)H12B—C12—H12C109.5
O2—C1—O1125.0 (3)O5—C13—H13A109.5
O2—C1—C2119.5 (3)O5—C13—H13B109.5
O1—C1—C2115.5 (3)H13A—C13—H13B109.5
N1—C2—C3123.8 (3)O5—C13—H13C109.5
N1—C2—C1116.9 (3)H13A—C13—H13C109.5
C3—C2—C1119.3 (3)H13B—C13—H13C109.5
C4—C3—C2118.6 (3)
O3—Pb1—O1—C1116.0 (3)O5—Pb1—N1—C10−110.9 (3)
O1i—Pb1—O1—C1−164.3 (3)O4—Pb1—N1—C1056.4 (3)
N1—Pb1—O1—C113.3 (3)O2i—Pb1—N1—C10148.3 (3)
O5—Pb1—O1—C1−78.4 (3)Pb1—O1—C1—O2169.7 (3)
O4—Pb1—O1—C178.3 (3)Pb1i—O1—C1—O25.3 (4)
O2i—Pb1—O1—C1−172.3 (3)Pb1—O1—C1—C2−12.1 (4)
O3—Pb1—O1—Pb1i−79.70 (12)Pb1i—O1—C1—C2−176.6 (2)
O1i—Pb1—O1—Pb1i0.0C10—N1—C2—C32.0 (5)
N1—Pb1—O1—Pb1i177.62 (15)Pb1—N1—C2—C3−170.2 (3)
O5—Pb1—O1—Pb1i85.90 (12)C10—N1—C2—C1−175.7 (3)
O4—Pb1—O1—Pb1i−117.41 (11)Pb1—N1—C2—C112.1 (4)
O2i—Pb1—O1—Pb1i−8.01 (13)O2—C1—C2—N1176.4 (3)
O1—Pb1—O3—C11−134.9 (3)O1—C1—C2—N1−1.8 (5)
O1i—Pb1—O3—C11159.2 (3)O2—C1—C2—C3−1.3 (5)
N1—Pb1—O3—C11−73.1 (3)O1—C1—C2—C3−179.6 (3)
O5—Pb1—O3—C11−159.9 (2)N1—C2—C3—C4−3.5 (6)
O4—Pb1—O3—C11−3.6 (2)C1—C2—C3—C4174.1 (3)
O2i—Pb1—O3—C11115.4 (3)C2—C3—C4—C51.7 (6)
O1—Pb1—O4—C1155.1 (2)C3—C4—C5—C101.4 (6)
O3—Pb1—O4—C113.7 (2)C3—C4—C5—C6−179.8 (4)
O1i—Pb1—O4—C11−16.2 (3)C4—C5—C6—C7−178.2 (4)
N1—Pb1—O4—C11111.5 (2)C10—C5—C6—C70.6 (6)
O5—Pb1—O4—C11147.1 (3)C5—C6—C7—C8−0.8 (6)
O2i—Pb1—O4—C11−56.6 (2)C6—C7—C8—C91.0 (6)
O1—Pb1—O5—C13−157.6 (3)C7—C8—C9—C10−1.0 (6)
O3—Pb1—O5—C13−131.9 (3)C2—N1—C10—C9−180.0 (3)
O1i—Pb1—O5—C13−91.6 (3)Pb1—N1—C10—C9−8.8 (4)
N1—Pb1—O5—C13137.7 (3)C2—N1—C10—C51.4 (5)
O4—Pb1—O5—C13102.7 (4)Pb1—N1—C10—C5172.5 (2)
O2i—Pb1—O5—C13−53.9 (3)C8—C9—C10—N1−177.9 (3)
O1—Pb1—N1—C2−12.5 (2)C8—C9—C10—C50.8 (5)
O3—Pb1—N1—C2−85.3 (2)C4—C5—C10—N1−3.0 (5)
O1i—Pb1—N1—C2−9.8 (3)C6—C5—C10—N1178.1 (3)
O5—Pb1—N1—C260.5 (2)C4—C5—C10—C9178.3 (3)
O4—Pb1—N1—C2−132.2 (2)C6—C5—C10—C9−0.6 (5)
O2i—Pb1—N1—C2−40.3 (5)Pb1—O4—C11—O3−6.2 (4)
O1—Pb1—N1—C10176.1 (3)Pb1—O4—C11—C12176.4 (4)
O3—Pb1—N1—C10103.2 (3)Pb1—O3—C11—O47.4 (5)
O1i—Pb1—N1—C10178.8 (2)Pb1—O3—C11—C12−175.2 (3)

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

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O5—H5···O3i0.84 (4)1.89 (4)2.685 (4)158 (5)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2798).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2009). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mohammadnezhad, G., Ghanbarpour, A. R., Amini, M. M. & Ng, S. W. (2010). Acta Cryst. E66, m946. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography