Acta Cryst. (2009). E65, m260 [ doi:10.1107/S1600536809003560 ]
-2-methylquinolin-8-olato)-
3N,O:O;
3O:N,O-bis[(acetato-
2O,O')lead(II)]Both independent PbII atoms in the title compound, [Pb2(C10H8NO)2(C2H3O2)2], are chelated by acetate and substituted quinolin-8-olate anions; the O atoms of the quinolin-8-olates also bridge to confer a five-coordinate status to each metal center. The geometry approximates a distorted
-fac octahedron in which one of the sites is occupied by a stereochemically active lone pair.
Lead acetate (0.38 g, 1 mmol) and 2-methyl-8-hydroxyquinoline (0.32 g, 2 mmol) were loaded into a convection tube; the tube was filled with dry methanol and kept at 333 K. Crystals were collected from the side arm after 1 day.
Carbon-bound H-atoms were placed in calculated positions (C—H 0.93 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C).
The quinolinyl ring was refined as a rigid group with C-C = 1.39 Å. The crystal diffracted strongly owing to two extremely heavy metal atoms. However, their presence introduced severe absorption problems that could not be corrected analytically as the crystal did not have regular faces. Although a sphere of reflections was measured, multi-scan treatment only marginally improved the quality. The final difference Fourier map had large peaks/deep holes near the lead atoms. The anisotropic displacement factors of the carbon, nitrogen and oxygen atoms had to be restrained to be nearly isotropic.
Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); 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).
| Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of Pb2(C2H3O2)2(C10H8NO)2 at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius. |
| [Pb2(C10H8NO)2(C2H3O2)2] | F(000) = 3136 |
| Mr = 848.82 | Dx = 2.440 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 6225 reflections |
| a = 13.7421 (2) Å | θ = 2.2–28.3° |
| b = 18.0682 (3) Å | µ = 14.60 mm−1 |
| c = 18.6113 (4) Å | T = 100 K |
| V = 4621.1 (1) Å3 | Block, yellow |
| Z = 8 | 0.20 × 0.10 × 0.08 mm |
| Bruker SMART APEX diffractometer | 4063 independent reflections |
| Radiation source: fine-focus sealed tube | 3133 reflections with I > 2σ(I) |
| graphite | Rint = 0.090 |
| ω scans | θmax = 25.0°, θmin = 2.2° |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
| Tmin = 0.158, Tmax = 0.388 | k = −21→21 |
| 33016 measured reflections | l = −22→21 |
| Refinement on F2 | Primary atom site location: structure-invariant direct methods |
| Least-squares matrix: full | Secondary atom site location: difference Fourier map |
| R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.115 | H-atom parameters constrained |
| S = 1.45 | w = 1/[σ2(Fo2) + (0.0388P)2 + 1P] where P = (Fo2 + 2Fc2)/3 |
| 4063 reflections | (Δ/σ)max = 0.001 |
| 264 parameters | Δρmax = 4.37 e Å−3 |
| 192 restraints | Δρmin = −2.70 e Å−3 |
| [Pb2(C10H8NO)2(C2H3O2)2] | V = 4621.1 (1) Å3 |
| Mr = 848.82 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 13.7421 (2) Å | µ = 14.60 mm−1 |
| b = 18.0682 (3) Å | T = 100 K |
| c = 18.6113 (4) Å | 0.20 × 0.10 × 0.08 mm |
| Bruker SMART APEX diffractometer | 4063 independent reflections |
| Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3133 reflections with I > 2σ(I) |
| Tmin = 0.158, Tmax = 0.388 | Rint = 0.090 |
| 33016 measured reflections | θmax = 25.0° |
| R[F2 > 2σ(F2)] = 0.046 | H-atom parameters constrained |
| wR(F2) = 0.115 | Δρmax = 4.37 e Å−3 |
| S = 1.45 | Δρmin = −2.70 e Å−3 |
| 4063 reflections | Absolute structure: ? |
| 264 parameters | Flack parameter: ? |
| 192 restraints | Rogers parameter: ? |
| x | y | z | Uiso*/Ueq | ||
| Pb1 | 0.28159 (3) | 0.37522 (2) | 0.52835 (2) | 0.01649 (15) | |
| Pb2 | 0.56385 (3) | 0.38486 (2) | 0.48211 (2) | 0.01580 (14) | |
| O1 | 0.3933 (6) | 0.4289 (4) | 0.4554 (4) | 0.0190 (18) | |
| O2 | 0.4542 (5) | 0.3401 (4) | 0.5634 (4) | 0.0193 (17) | |
| O3 | 0.3217 (6) | 0.4747 (4) | 0.6014 (5) | 0.029 (2) | |
| O4 | 0.1631 (6) | 0.4725 (4) | 0.5938 (5) | 0.027 (2) | |
| O5 | 0.5071 (6) | 0.2851 (4) | 0.4186 (4) | 0.027 (2) | |
| O6 | 0.6648 (6) | 0.2738 (4) | 0.3994 (5) | 0.030 (2) | |
| C1 | 0.3673 (3) | 0.4758 (3) | 0.4007 (3) | 0.017 (2) | |
| C2 | 0.4354 (3) | 0.5134 (3) | 0.3593 (3) | 0.021 (3) | |
| H2 | 0.5029 | 0.5076 | 0.3689 | 0.026* | |
| C3 | 0.4048 (3) | 0.5595 (3) | 0.3040 (3) | 0.020 (3) | |
| H3 | 0.4514 | 0.5852 | 0.2757 | 0.024* | |
| C4 | 0.3061 (4) | 0.5680 (3) | 0.2900 (3) | 0.019 (3) | |
| H4 | 0.2852 | 0.5996 | 0.2522 | 0.023* | |
| C5 | 0.2380 (3) | 0.53044 (19) | 0.3314 (2) | 0.021 (3) | |
| C6 | 0.2686 (3) | 0.48434 (18) | 0.3868 (2) | 0.015 (2) | |
| N1 | 0.2004 (3) | 0.4467 (2) | 0.4282 (2) | 0.016 (2) | |
| C9 | 0.1017 (3) | 0.4552 (3) | 0.4142 (3) | 0.017 (2) | |
| C8 | 0.0711 (3) | 0.5013 (3) | 0.3589 (3) | 0.022 (3) | |
| H8 | 0.0036 | 0.5072 | 0.3494 | 0.026* | |
| C7 | 0.1392 (3) | 0.5389 (3) | 0.3175 (3) | 0.019 (3) | |
| H7 | 0.1183 | 0.5705 | 0.2797 | 0.023* | |
| C10 | 0.0363 (9) | 0.4109 (6) | 0.4591 (7) | 0.025 (3) | |
| H10A | 0.0535 | 0.3585 | 0.4547 | 0.038* | |
| H10B | −0.0310 | 0.4183 | 0.4432 | 0.038* | |
| H10C | 0.0427 | 0.4264 | 0.5093 | 0.038* | |
| C11 | 0.4812 (3) | 0.2885 (3) | 0.6133 (3) | 0.017 (2) | |
| C12 | 0.4148 (3) | 0.2545 (3) | 0.6589 (3) | 0.024 (3) | |
| H12 | 0.3475 | 0.2659 | 0.6554 | 0.028* | |
| C13 | 0.4469 (3) | 0.2036 (3) | 0.7097 (3) | 0.018 (3) | |
| H13 | 0.4016 | 0.1803 | 0.7409 | 0.022* | |
| C14 | 0.5454 (4) | 0.1868 (3) | 0.7148 (3) | 0.022 (3) | |
| H14 | 0.5673 | 0.1521 | 0.7496 | 0.026* | |
| C15 | 0.6118 (3) | 0.22089 (19) | 0.6692 (2) | 0.018 (3) | |
| C16 | 0.5797 (3) | 0.27173 (19) | 0.6184 (2) | 0.013 (2) | |
| N2 | 0.6460 (3) | 0.3058 (2) | 0.5728 (2) | 0.015 (2) | |
| C19 | 0.7445 (3) | 0.2890 (3) | 0.5779 (3) | 0.017 (3) | |
| C18 | 0.7766 (3) | 0.2382 (3) | 0.6287 (3) | 0.021 (3) | |
| H18 | 0.8439 | 0.2267 | 0.6322 | 0.026* | |
| C17 | 0.7102 (3) | 0.2041 (3) | 0.6743 (3) | 0.017 (2) | |
| H17 | 0.7322 | 0.1694 | 0.7090 | 0.021* | |
| C20 | 0.8077 (9) | 0.3291 (6) | 0.5282 (7) | 0.024 (3) | |
| H20A | 0.8022 | 0.3824 | 0.5372 | 0.036* | |
| H20B | 0.7880 | 0.3184 | 0.4787 | 0.036* | |
| H20C | 0.8752 | 0.3134 | 0.5355 | 0.036* | |
| C21 | 0.2377 (9) | 0.5005 (6) | 0.6175 (6) | 0.019 (3) | |
| C22 | 0.2349 (10) | 0.5681 (6) | 0.6657 (7) | 0.031 (3) | |
| H22A | 0.2560 | 0.6116 | 0.6385 | 0.047* | |
| H22B | 0.2785 | 0.5605 | 0.7067 | 0.047* | |
| H22C | 0.1683 | 0.5757 | 0.6831 | 0.047* | |
| C23 | 0.5803 (8) | 0.2518 (6) | 0.3911 (6) | 0.017 (3) | |
| C24 | 0.5582 (9) | 0.1846 (6) | 0.3472 (6) | 0.023 (3) | |
| H24A | 0.5722 | 0.1948 | 0.2965 | 0.035* | |
| H24B | 0.4894 | 0.1717 | 0.3526 | 0.035* | |
| H24C | 0.5987 | 0.1432 | 0.3637 | 0.035* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Pb1 | 0.0121 (3) | 0.0160 (2) | 0.0214 (3) | −0.00051 (15) | 0.00086 (17) | 0.00142 (16) |
| Pb2 | 0.0108 (2) | 0.0164 (2) | 0.0201 (3) | 0.00012 (15) | 0.00039 (17) | 0.00064 (17) |
| O1 | 0.011 (4) | 0.024 (4) | 0.023 (4) | 0.004 (3) | 0.002 (3) | 0.008 (3) |
| O2 | 0.013 (4) | 0.021 (4) | 0.023 (4) | 0.003 (3) | 0.002 (3) | 0.004 (3) |
| O3 | 0.013 (5) | 0.027 (4) | 0.047 (5) | −0.002 (3) | 0.000 (4) | −0.013 (4) |
| O4 | 0.018 (5) | 0.031 (4) | 0.033 (5) | 0.003 (3) | −0.001 (4) | −0.008 (3) |
| O5 | 0.018 (4) | 0.027 (4) | 0.034 (5) | −0.005 (3) | −0.001 (4) | −0.012 (3) |
| O6 | 0.020 (5) | 0.034 (4) | 0.036 (5) | 0.001 (4) | 0.000 (4) | −0.004 (4) |
| C1 | 0.013 (6) | 0.018 (5) | 0.019 (6) | −0.004 (4) | 0.004 (4) | −0.001 (4) |
| C2 | 0.018 (6) | 0.018 (5) | 0.028 (6) | −0.003 (4) | 0.001 (5) | 0.002 (4) |
| C3 | 0.018 (6) | 0.022 (5) | 0.020 (6) | −0.005 (4) | 0.002 (5) | −0.001 (4) |
| C4 | 0.020 (6) | 0.018 (5) | 0.020 (6) | −0.002 (4) | −0.006 (5) | −0.001 (4) |
| C5 | 0.022 (6) | 0.014 (5) | 0.025 (6) | 0.003 (4) | 0.000 (5) | −0.002 (4) |
| C6 | 0.006 (5) | 0.018 (5) | 0.020 (6) | 0.003 (4) | 0.005 (4) | −0.002 (4) |
| N1 | 0.018 (5) | 0.012 (4) | 0.018 (5) | 0.010 (3) | −0.003 (4) | 0.002 (3) |
| C9 | 0.011 (5) | 0.017 (5) | 0.024 (6) | 0.001 (4) | 0.001 (4) | −0.007 (4) |
| C8 | 0.014 (6) | 0.024 (5) | 0.027 (6) | 0.003 (4) | −0.005 (5) | 0.001 (4) |
| C7 | 0.016 (6) | 0.018 (5) | 0.023 (6) | −0.001 (4) | −0.004 (5) | 0.004 (4) |
| C10 | 0.020 (6) | 0.027 (5) | 0.029 (6) | −0.002 (5) | 0.000 (5) | −0.002 (5) |
| C11 | 0.014 (6) | 0.024 (5) | 0.014 (5) | 0.003 (4) | 0.001 (4) | 0.000 (4) |
| C12 | 0.020 (6) | 0.027 (5) | 0.025 (6) | −0.001 (4) | 0.002 (5) | −0.002 (5) |
| C13 | 0.016 (6) | 0.019 (5) | 0.020 (6) | −0.007 (4) | 0.003 (5) | 0.000 (4) |
| C14 | 0.026 (6) | 0.023 (5) | 0.016 (6) | −0.004 (5) | 0.002 (5) | 0.001 (4) |
| C15 | 0.020 (6) | 0.014 (5) | 0.021 (6) | 0.002 (4) | −0.001 (5) | −0.005 (4) |
| C16 | 0.012 (6) | 0.016 (5) | 0.012 (5) | −0.003 (4) | −0.001 (4) | −0.005 (4) |
| N2 | 0.020 (5) | 0.013 (4) | 0.013 (5) | 0.005 (4) | −0.001 (4) | 0.001 (3) |
| C19 | 0.013 (6) | 0.019 (5) | 0.018 (6) | −0.001 (4) | 0.002 (4) | 0.000 (4) |
| C18 | 0.016 (6) | 0.025 (5) | 0.023 (6) | 0.005 (4) | −0.002 (5) | 0.000 (4) |
| C17 | 0.017 (6) | 0.016 (5) | 0.019 (6) | 0.003 (4) | −0.002 (5) | 0.004 (4) |
| C20 | 0.020 (6) | 0.021 (5) | 0.031 (6) | 0.002 (4) | −0.003 (5) | −0.001 (4) |
| C21 | 0.017 (6) | 0.017 (5) | 0.022 (6) | −0.002 (4) | −0.001 (5) | 0.006 (4) |
| C22 | 0.036 (7) | 0.022 (5) | 0.036 (7) | −0.002 (5) | 0.005 (6) | −0.003 (5) |
| C23 | 0.015 (6) | 0.018 (5) | 0.019 (5) | −0.003 (4) | 0.000 (5) | 0.003 (4) |
| C24 | 0.023 (6) | 0.023 (5) | 0.023 (6) | −0.001 (5) | −0.001 (5) | 0.000 (4) |
| Pb1—O1 | 2.267 (8) | C7—H7 | 0.9500 |
| Pb1—O3 | 2.321 (8) | C10—H10A | 0.9800 |
| Pb1—N1 | 2.527 (4) | C10—H10B | 0.9800 |
| Pb1—O2 | 2.541 (7) | C10—H10C | 0.9800 |
| Pb1—O4 | 2.688 (8) | C11—C12 | 1.3900 |
| Pb2—O2 | 2.283 (7) | C11—C16 | 1.3900 |
| Pb2—O5 | 2.292 (7) | C12—C13 | 1.3900 |
| Pb2—N2 | 2.482 (4) | C12—H12 | 0.9500 |
| Pb2—O1 | 2.525 (7) | C13—C14 | 1.3900 |
| Pb2—O4 | 6.095 (8) | C13—H13 | 0.9500 |
| O1—C1 | 1.372 (8) | C14—C15 | 1.3900 |
| O2—C11 | 1.366 (8) | C14—H14 | 0.9500 |
| O3—C21 | 1.280 (14) | C15—C16 | 1.3900 |
| O4—C21 | 1.226 (14) | C15—C17 | 1.3900 |
| O5—C23 | 1.279 (13) | C16—N2 | 1.3900 |
| O6—C23 | 1.237 (13) | N2—C19 | 1.3900 |
| C1—C2 | 1.3900 | C19—C18 | 1.3900 |
| C1—C6 | 1.3900 | C19—C20 | 1.460 (12) |
| C2—C3 | 1.3900 | C18—C17 | 1.3900 |
| C2—H2 | 0.9500 | C18—H18 | 0.9500 |
| C3—C4 | 1.3900 | C17—H17 | 0.9500 |
| C3—H3 | 0.9500 | C20—H20A | 0.9800 |
| C4—C5 | 1.3900 | C20—H20B | 0.9800 |
| C4—H4 | 0.9500 | C20—H20C | 0.9800 |
| C5—C6 | 1.3900 | C21—C22 | 1.515 (16) |
| C5—C7 | 1.3900 | C22—H22A | 0.9800 |
| C6—N1 | 1.3900 | C22—H22B | 0.9800 |
| N1—C9 | 1.3900 | C22—H22C | 0.9800 |
| C9—C8 | 1.3900 | C23—C24 | 1.494 (15) |
| C9—C10 | 1.465 (12) | C24—H24A | 0.9800 |
| C8—C7 | 1.3900 | C24—H24B | 0.9800 |
| C8—H8 | 0.9500 | C24—H24C | 0.9800 |
| O1—Pb1—O3 | 81.9 (3) | C9—C10—H10A | 109.5 |
| O1—Pb1—N1 | 68.8 (2) | C9—C10—H10B | 109.5 |
| O3—Pb1—N1 | 98.1 (2) | H10A—C10—H10B | 109.5 |
| O1—Pb1—O2 | 68.2 (2) | C9—C10—H10C | 109.5 |
| O3—Pb1—O2 | 79.7 (3) | H10A—C10—H10C | 109.5 |
| N1—Pb1—O2 | 136.80 (19) | H10B—C10—H10C | 109.5 |
| O1—Pb1—O4 | 113.7 (2) | O2—C11—C12 | 122.6 (4) |
| O3—Pb1—O4 | 51.1 (3) | O2—C11—C16 | 117.4 (4) |
| N1—Pb1—O4 | 74.5 (2) | C12—C11—C16 | 120.0 |
| O2—Pb1—O4 | 127.8 (2) | C11—C12—C13 | 120.0 |
| O2—Pb2—O5 | 80.7 (3) | C11—C12—H12 | 120.0 |
| O2—Pb2—N2 | 69.3 (2) | C13—C12—H12 | 120.0 |
| O5—Pb2—N2 | 93.0 (2) | C14—C13—C12 | 120.0 |
| O2—Pb2—O1 | 68.3 (2) | C14—C13—H13 | 120.0 |
| O5—Pb2—O1 | 80.3 (3) | C12—C13—H13 | 120.0 |
| N2—Pb2—O1 | 137.5 (2) | C13—C14—C15 | 120.0 |
| O2—Pb2—O4 | 43.12 (19) | C13—C14—H14 | 120.0 |
| O5—Pb2—O4 | 94.2 (2) | C15—C14—H14 | 120.0 |
| N2—Pb2—O4 | 109.19 (13) | C14—C15—C16 | 120.0 |
| O1—Pb2—O4 | 31.4 (2) | C14—C15—C17 | 120.0 |
| C1—O1—Pb1 | 122.2 (5) | C16—C15—C17 | 120.0 |
| C1—O1—Pb2 | 125.6 (5) | N2—C16—C15 | 120.0 |
| Pb1—O1—Pb2 | 112.1 (3) | N2—C16—C11 | 120.0 |
| C11—O2—Pb2 | 120.9 (5) | C15—C16—C11 | 120.0 |
| C11—O2—Pb1 | 126.7 (5) | C16—N2—C19 | 120.0 |
| Pb2—O2—Pb1 | 111.0 (3) | C16—N2—Pb2 | 111.83 (17) |
| C21—O3—Pb1 | 101.8 (7) | C19—N2—Pb2 | 127.96 (17) |
| C21—O4—Pb1 | 85.8 (7) | N2—C19—C18 | 120.0 |
| C21—O4—Pb2 | 58.3 (7) | N2—C19—C20 | 115.3 (6) |
| C23—O5—Pb2 | 108.0 (7) | C18—C19—C20 | 124.7 (6) |
| O1—C1—C2 | 122.5 (4) | C17—C18—C19 | 120.0 |
| O1—C1—C6 | 117.5 (4) | C17—C18—H18 | 120.0 |
| C2—C1—C6 | 120.0 | C19—C18—H18 | 120.0 |
| C3—C2—C1 | 120.0 | C18—C17—C15 | 120.0 |
| C3—C2—H2 | 120.0 | C18—C17—H17 | 120.0 |
| C1—C2—H2 | 120.0 | C15—C17—H17 | 120.0 |
| C2—C3—C4 | 120.0 | C19—C20—H20A | 109.5 |
| C2—C3—H3 | 120.0 | C19—C20—H20B | 109.5 |
| C4—C3—H3 | 120.0 | H20A—C20—H20B | 109.5 |
| C5—C4—C3 | 120.0 | C19—C20—H20C | 109.5 |
| C5—C4—H4 | 120.0 | H20A—C20—H20C | 109.5 |
| C3—C4—H4 | 120.0 | H20B—C20—H20C | 109.5 |
| C6—C5—C4 | 120.0 | O4—C21—O3 | 121.3 (10) |
| C6—C5—C7 | 120.0 | O4—C21—C22 | 121.6 (11) |
| C4—C5—C7 | 120.0 | O3—C21—C22 | 117.1 (11) |
| N1—C6—C5 | 120.0 | C21—C22—H22A | 109.5 |
| N1—C6—C1 | 120.0 | C21—C22—H22B | 109.5 |
| C5—C6—C1 | 120.0 | H22A—C22—H22B | 109.5 |
| C6—N1—C9 | 120.0 | C21—C22—H22C | 109.5 |
| C6—N1—Pb1 | 111.19 (17) | H22A—C22—H22C | 109.5 |
| C9—N1—Pb1 | 128.68 (17) | H22B—C22—H22C | 109.5 |
| C8—C9—N1 | 120.0 | O6—C23—O5 | 122.4 (10) |
| C8—C9—C10 | 124.4 (6) | O6—C23—C24 | 121.3 (11) |
| N1—C9—C10 | 115.6 (6) | O5—C23—C24 | 116.2 (10) |
| C9—C8—C7 | 120.0 | C23—C24—H24A | 109.5 |
| C9—C8—H8 | 120.0 | C23—C24—H24B | 109.5 |
| C7—C8—H8 | 120.0 | H24A—C24—H24B | 109.5 |
| C8—C7—C5 | 120.0 | C23—C24—H24C | 109.5 |
| C8—C7—H7 | 120.0 | H24A—C24—H24C | 109.5 |
| C5—C7—H7 | 120.0 | H24B—C24—H24C | 109.5 |
| O3—Pb1—O1—C1 | −96.4 (6) | C2—C1—C6—N1 | 180.0 |
| N1—Pb1—O1—C1 | 5.6 (5) | O1—C1—C6—C5 | −179.2 (6) |
| O2—Pb1—O1—C1 | −178.6 (7) | C2—C1—C6—C5 | 0.0 |
| O4—Pb1—O1—C1 | −55.5 (7) | C5—C6—N1—C9 | 0.0 |
| O3—Pb1—O1—Pb2 | 87.6 (3) | C1—C6—N1—C9 | 180.0 |
| N1—Pb1—O1—Pb2 | −170.4 (4) | C5—C6—N1—Pb1 | −176.3 (3) |
| O2—Pb1—O1—Pb2 | 5.5 (3) | C1—C6—N1—Pb1 | 3.7 (3) |
| O4—Pb1—O1—Pb2 | 128.5 (3) | O1—Pb1—N1—C6 | −4.6 (2) |
| O2—Pb2—O1—C1 | 178.1 (7) | O3—Pb1—N1—C6 | 73.3 (3) |
| O5—Pb2—O1—C1 | −98.1 (6) | O2—Pb1—N1—C6 | −10.3 (4) |
| N2—Pb2—O1—C1 | 178.1 (5) | O4—Pb1—N1—C6 | 119.1 (3) |
| O4—Pb2—O1—C1 | 146.9 (8) | O1—Pb1—N1—C9 | 179.5 (3) |
| O2—Pb2—O1—Pb1 | −6.1 (3) | O3—Pb1—N1—C9 | −102.5 (3) |
| O5—Pb2—O1—Pb1 | 77.7 (3) | O2—Pb1—N1—C9 | 173.9 (3) |
| N2—Pb2—O1—Pb1 | −6.1 (5) | O4—Pb1—N1—C9 | −56.8 (3) |
| O4—Pb2—O1—Pb1 | −37.3 (2) | C6—N1—C9—C8 | 0.0 |
| O5—Pb2—O2—C11 | 89.3 (6) | Pb1—N1—C9—C8 | 175.5 (3) |
| N2—Pb2—O2—C11 | −7.5 (5) | C6—N1—C9—C10 | 177.7 (6) |
| O1—Pb2—O2—C11 | 172.5 (6) | Pb1—N1—C9—C10 | −6.8 (6) |
| O4—Pb2—O2—C11 | −164.3 (7) | N1—C9—C8—C7 | 0.0 |
| O5—Pb2—O2—Pb1 | −77.7 (3) | C10—C9—C8—C7 | −177.4 (7) |
| N2—Pb2—O2—Pb1 | −174.6 (3) | C9—C8—C7—C5 | 0.0 |
| O1—Pb2—O2—Pb1 | 5.4 (2) | C6—C5—C7—C8 | 0.0 |
| O4—Pb2—O2—Pb1 | 28.68 (16) | C4—C5—C7—C8 | 180.0 |
| O1—Pb1—O2—C11 | −172.1 (7) | Pb2—O2—C11—C12 | −173.4 (2) |
| O3—Pb1—O2—C11 | 102.6 (6) | Pb1—O2—C11—C12 | −8.6 (7) |
| N1—Pb1—O2—C11 | −166.5 (5) | Pb2—O2—C11—C16 | 8.0 (7) |
| O4—Pb1—O2—C11 | 84.2 (6) | Pb1—O2—C11—C16 | 172.8 (3) |
| O1—Pb1—O2—Pb2 | −6.0 (3) | O2—C11—C12—C13 | −178.6 (6) |
| O3—Pb1—O2—Pb2 | −91.3 (3) | C16—C11—C12—C13 | 0.0 |
| N1—Pb1—O2—Pb2 | −0.4 (5) | C11—C12—C13—C14 | 0.0 |
| O4—Pb1—O2—Pb2 | −109.7 (3) | C12—C13—C14—C15 | 0.0 |
| O1—Pb1—O3—C21 | 130.1 (7) | C13—C14—C15—C16 | 0.0 |
| N1—Pb1—O3—C21 | 63.0 (7) | C13—C14—C15—C17 | 180.0 |
| O2—Pb1—O3—C21 | −160.8 (7) | C14—C15—C16—N2 | 180.0 |
| O4—Pb1—O3—C21 | 0.5 (6) | C17—C15—C16—N2 | 0.0 |
| O1—Pb1—O4—C21 | −57.0 (7) | C14—C15—C16—C11 | 0.0 |
| O3—Pb1—O4—C21 | −0.5 (7) | C17—C15—C16—C11 | 180.0 |
| N1—Pb1—O4—C21 | −114.9 (7) | O2—C11—C16—N2 | −1.4 (6) |
| O2—Pb1—O4—C21 | 23.0 (8) | C12—C11—C16—N2 | 180.0 |
| O1—Pb1—O4—Pb2 | −37.8 (2) | O2—C11—C16—C15 | 178.6 (6) |
| O3—Pb1—O4—Pb2 | 18.6 (4) | C12—C11—C16—C15 | 0.0 |
| N1—Pb1—O4—Pb2 | −95.7 (2) | C15—C16—N2—C19 | 0.0 |
| O2—Pb1—O4—Pb2 | 42.2 (2) | C11—C16—N2—C19 | 180.0 |
| O2—Pb2—O4—C21 | 97.5 (8) | C15—C16—N2—Pb2 | 175.1 (3) |
| O5—Pb2—O4—C21 | 169.2 (8) | C11—C16—N2—Pb2 | −4.9 (3) |
| N2—Pb2—O4—C21 | 74.5 (8) | O2—Pb2—N2—C16 | 6.2 (2) |
| O1—Pb2—O4—C21 | −127.3 (8) | O5—Pb2—N2—C16 | −72.7 (3) |
| O2—Pb2—O4—Pb1 | −59.9 (3) | O1—Pb2—N2—C16 | 6.2 (4) |
| O5—Pb2—O4—Pb1 | 11.8 (3) | O4—Pb2—N2—C16 | 22.8 (2) |
| N2—Pb2—O4—Pb1 | −82.9 (3) | O2—Pb2—N2—C19 | −179.2 (3) |
| O1—Pb2—O4—Pb1 | 75.4 (4) | O5—Pb2—N2—C19 | 101.9 (3) |
| O2—Pb2—O5—C23 | −135.3 (7) | O1—Pb2—N2—C19 | −179.2 (3) |
| N2—Pb2—O5—C23 | −66.8 (7) | O4—Pb2—N2—C19 | −162.6 (2) |
| O1—Pb2—O5—C23 | 155.4 (7) | C16—N2—C19—C18 | 0.0 |
| O4—Pb2—O5—C23 | −176.4 (7) | Pb2—N2—C19—C18 | −174.2 (3) |
| Pb1—O1—C1—C2 | 174.9 (3) | C16—N2—C19—C20 | −178.9 (6) |
| Pb2—O1—C1—C2 | −9.7 (7) | Pb2—N2—C19—C20 | 6.9 (6) |
| Pb1—O1—C1—C6 | −5.9 (7) | N2—C19—C18—C17 | 0.0 |
| Pb2—O1—C1—C6 | 169.5 (3) | C20—C19—C18—C17 | 178.8 (7) |
| O1—C1—C2—C3 | 179.2 (6) | C19—C18—C17—C15 | 0.0 |
| C6—C1—C2—C3 | 0.0 | C14—C15—C17—C18 | 180.0 |
| C1—C2—C3—C4 | 0.0 | C16—C15—C17—C18 | 0.0 |
| C2—C3—C4—C5 | 0.0 | Pb1—O4—C21—O3 | 0.9 (11) |
| C3—C4—C5—C6 | 0.0 | Pb2—O4—C21—O3 | −10.0 (8) |
| C3—C4—C5—C7 | 180.0 | Pb1—O4—C21—C22 | 179.5 (10) |
| C4—C5—C6—N1 | 180.0 | Pb2—O4—C21—C22 | 168.6 (13) |
| C7—C5—C6—N1 | 0.0 | Pb1—O3—C21—O4 | −1.0 (13) |
| C4—C5—C6—C1 | 0.0 | Pb1—O3—C21—C22 | −179.7 (8) |
| C7—C5—C6—C1 | 180.0 | Pb2—O5—C23—O6 | −0.7 (13) |
| O1—C1—C6—N1 | 0.8 (5) | Pb2—O5—C23—C24 | 180.0 (7) |
We thank Shahid Beheshti University and the University of Malaya for supporting this study.
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Shahverdizadeh, G. H., Soudi, A. A., Morsali, A. & Retailleau, P. (2008). Inorg. Chim. Acta, 361, 1875–1884.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Westrip, S. P. (2009). publCIF. In preparation.