Bis(μ-2-methyl­quinolin-8-olato)-κ3N,O:O;κ3O:N,O-bis­[(acetato-κ2O,O′)lead(II)]

Mohammadnezhad Sh., G.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536809003560

metal-organic compounds

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Volume 65| Part 3| March 2009| Page m260

doi:10.1107/S1600536809003560

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Bis(μ-2-methylquinolin-8-olato)-κ³N,O:O;κ³O:N,O-bis[(acetato-κ²O,O′)lead(II)]

Gholamhossein Mohammadnezhad Sh.,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 27 January 2009; accepted 29 January 2009; online 11 February 2009)

Both independent Pb^II 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 Ψ-fac octahedron in which one of the sites is occupied by a stereochemically active lone pair.

Related literature

The structural chemistry of lead(II) 8-hydroxyquinolinates has been reviewed, including bis(μ-acetato)diacetatotetrakis(μ-quinolin-8-olato)tetralead dihydrate (Shahverdizadeh et al., 2008 ).

Experimental

Crystal data

[Pb₂(C₁₀H₈NO)₂(C₂H₃O₂)₂]
M_r = 848.82
Orthorhombic, P b c a
a = 13.7421 (2) Å
b = 18.0682 (3) Å
c = 18.6113 (4) Å
V = 4621.1 (1) Å³
Z = 8
Mo Kα radiation
μ = 14.60 mm⁻¹
T = 100 (2) K
0.20 × 0.10 × 0.08 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.158, T_max = 0.388 (expected range = 0.127–0.311)
33016 measured reflections
4063 independent reflections
3133 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.115
S = 1.45
4063 reflections
264 parameters
192 restraints
H-atom parameters constrained
Δρ_max = 4.37 e Å⁻³
Δρ_min = −2.70 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809003560/tk2364sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809003560/tk2364Isup2.hkl

checkCIF report

Related literature top

The structural chemistry of lead(II) 8-hydroxyquinolinates has been reviewed; for bis(µ-acetato)diacetatotetrakis(µ-quinolin-8-olato)tetralead dihydrate in particular, see: Shahverdizadeh et al. (2008).

Experimental top

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.

Computing details top

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).

Figures top

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.

Bis(µ-2-methylquinolin-8-οlato)- κ³N,O:O;κ³O:N,O- bis[(acetato-κ²O,O')lead(II)] top

Crystal data top

[Pb₂(C₁₀H₈NO)₂(C₂H₃O₂)₂]	F(000) = 3136
M_r = 848.82	D_x = 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

Data collection top

Bruker SMART APEX diffractometer	4063 independent reflections
Radiation source: fine-focus sealed tube	3133 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
T_min = 0.158, T_max = 0.388	k = −21→21
33016 measured reflections	l = −22→21

Refinement top

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(F_o²) + (0.0388P)² + 1P] where P = (F_o² + 2F_c²)/3
4063 reflections	(Δ/σ)_max = 0.001
264 parameters	Δρ_max = 4.37 e Å⁻³
192 restraints	Δρ_min = −2.70 e Å⁻³

Crystal data top

[Pb₂(C₁₀H₈NO)₂(C₂H₃O₂)₂]	V = 4621.1 (1) Å³
M_r = 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

Data collection top

Bruker SMART APEX diffractometer	4063 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3133 reflections with I > 2σ(I)
T_min = 0.158, T_max = 0.388	R_int = 0.090
33016 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	192 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.45	Δρ_max = 4.37 e Å⁻³
4063 reflections	Δρ_min = −2.70 e Å⁻³
264 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	[Pb₂(C₁₀H₈NO)₂(C₂H₃O₂)₂]
M_r	848.82
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	100
a, b, c (Å)	13.7421 (2), 18.0682 (3), 18.6113 (4)
V (Å³)	4621.1 (1)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	14.60
Crystal size (mm)	0.20 × 0.10 × 0.08

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.158, 0.388
No. of measured, independent and observed [I > 2σ(I)] reflections	33016, 4063, 3133
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.115, 1.45
No. of reflections	4063
No. of parameters	264
No. of restraints	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	4.37, −2.70

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Shahverdizadeh, G. H., Soudi, A. A., Morsali, A. & Retailleau, P. (2008). Inorg. Chim. Acta, 361, 1875–1884. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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