Poly[bis­(μ3-benzene-1,4-dicarboxyl­ato-κ4O:O′:O′′,O′′′)bis­(1-methyl­pyrrolidin-2-one-κO)dilead(II)]

Du, C.; Yang, S.-Y.; Huang, R.-B.

doi:10.1107/S1600536807037981

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Poly[bis(μ₃-benzene-1,4-dicarboxylato-κ⁴O:O′:O′′,O′′′)bis(1-methylpyrrolidin-2-one-κO)dilead(II)]

C. Du, S.-Y. Yang and R.-B. Huang

A new coordination polymer, [Pb₂(C₈H₄O₄)₂(C₅H₉NO)₂]_n, has been prepared by the reaction of Pb(NO₃)₂ with benzene-1,4-dicarboxylic acid (H₂bdc) in 1-methylpyrrolidin-2-one (nmp). There are two types of Pb ions in the crystal structure, one coordinated by five O atoms and the other by six O atoms, with severely distorted pyramidal and severely distorted octahedral coordination geometries, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807037981/ww2082sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807037981/ww2082Isup2.hkl Contains datablock I

CCDC reference: 663563

checkCIF report

Key indicators

Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.009 Å
R factor = 0.033
wR factor = 0.079
Data-to-parameter ratio = 17.0

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.97
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        300 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.47 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.58 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O9
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          9

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C8     = ...          R
PLAT794_ALERT_5_G Check Predicted Bond Valency for Pb1         (2)       2.12
PLAT794_ALERT_5_G Check Predicted Bond Valency for Pb2         (2)       2.00

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

The three-dimensional coordination polymers have received much attention in recent years. However, most of the reported structures are transition metal compounds (Li et al., 1999; Rosi et al., 2005); compounds with main group metals such as Pb are seldom reported (Schuy & Ruschewitz, 2005; Zhou et al., 2006). Herein the crystal structure of a three-dimensional lead coordination polymer [Pb₂(C₈H₄O₄)₂(C₅H₉NO)₂]_n, is reported.

In the title compound, [Pb₂(C₈H₄O₄)₂(C₅H₉NO)₂]_n, the two Pb atoms in the structure exist in different coordination geometries (Fig. 1). The Pb1 ion is coordinated by five O atoms, four of which are from three carboxyl groups and one is from a nmp molecule, with 'stereo-chemically active' electron lone pair, and the coordination sphere is hemi-directed (Hancock et al., 1988). [Pb1—O2 2.381 (4) Å; Pb1—O5 2.410 (4) Å; Pb1—O6 2.461 (4) Å; Pb1—O3ⁱ 2.486 (4) Å; Pb1—O9 2.633 (5) Å]. The Pb2 ion is coordinated by six O atoms, five of which are from three carboxyl groups and one is from a nmp molecule. [Pb2—O7 2.434 (4) Å; Pb2—O8 2.456 (4) Å; Pb2—O4ⁱⁱ 2.494 (4) Å; Pb2—O1 2.552 (4) Å; Pb2—O10 2.657 (5) Å; Pb2—O3ⁱⁱ 2.660 (4) Å]. There are three coordination modes between Pb ions and carboxyl groups: (a) chelating/bridging bidentate, (b) chelating bidentate, (c) bidentate. The Pb ions are connected by carboxyl groups to form metal chains along a axis. Furthermore the bdc dianions connect each chain to four neighboring chains, resulting in a three-dimensional network with channels in which nmp molecules reside as coordinated ligands (Fig. 2).

Related literature top

For related literature, see: Hancock et al. (1988); Li et al. (1999); Rosi et al. (2005); Schuy & Ruschewitz (2005); Zhou et al. (2006).

Experimental top

The title compound was synthesized with lead nitrate (0.331 g, 1 mmol) and H₂bdc (0.166 g, 1 mmol) in nmp (15 ml). The mixture was placed in a 25 ml conical flask, which was heated at 363 K for 3 days. The product was isolated in 55% yield. The elemental analysis for the title compound is almost in agreement with the theoretical values. (Found wt%: C, 32.88; H, 2.74; N, 2.99; calculated wt%: C, 33.19; H, 2.78; N, 2.98).

Structure description top

For related literature, see: Hancock et al. (1988); Li et al. (1999); Rosi et al. (2005); Schuy & Ruschewitz (2005); Zhou et al. (2006).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Figures top

	Fig. 1. The molecular structure of the title compound, shown with 50% probability displacement ellipsoids. [Symmetry codes: (i) x, y + 1, z; (ii) x - 1, y + 1, z, (v) 2 - x, 1 - y, 1 - z, (vi) 1 - x, 2 - y, -z.]
	Fig. 2. Perspective view down the a axis showing the three-dimensional structrue of the title compound.

Poly[bis(µ₃-benzene-1,4-dicarboxylato-κ⁴O:O':O'',O''')bis(1- methylpyrrolidin-2-one-κO)dilead(II)] top

Crystal data top

[Pb₂(C₈H₄O₄)₂(C₅H₉NO)₂]	Z = 2
M_r = 940.87	F(000) = 880
Triclinic, P1	D_x = 2.370 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.7327 (11) Å	Cell parameters from 7207 reflections
b = 10.1503 (17) Å	θ = 2.5–28.6°
c = 20.249 (3) Å	µ = 12.82 mm⁻¹
α = 78.521 (3)°	T = 223 K
β = 83.357 (3)°	Plate, light-yellow
γ = 77.113 (3)°	0.18 × 0.10 × 0.03 mm
V = 1318.3 (4) Å³

Data collection top

Bruker APEX area-detector diffractometer	6153 independent reflections
Radiation source: fine-focus sealed tube	5400 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
φ and ω scans	θ_max = 28.6°, θ_min = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −8→8
T_min = 0.206, T_max = 0.700	k = −13→13
15362 measured reflections	l = −26→26

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0336P)² + 2.0349P] where P = (F_o² + 2F_c²)/3
6153 reflections	(Δ/σ)_max = 0.001
361 parameters	Δρ_max = 2.38 e Å⁻³
0 restraints	Δρ_min = −1.53 e Å⁻³

Crystal data top

[Pb₂(C₈H₄O₄)₂(C₅H₉NO)₂]	γ = 77.113 (3)°
M_r = 940.87	V = 1318.3 (4) Å³
Triclinic, P1	Z = 2
a = 6.7327 (11) Å	Mo Kα radiation
b = 10.1503 (17) Å	µ = 12.82 mm⁻¹
c = 20.249 (3) Å	T = 223 K
α = 78.521 (3)°	0.18 × 0.10 × 0.03 mm
β = 83.357 (3)°

Data collection top

Bruker APEX area-detector diffractometer	6153 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	5400 reflections with I > 2σ(I)
T_min = 0.206, T_max = 0.700	R_int = 0.038
15362 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	0 restraints
wR(F²) = 0.079	H-atom parameters constrained
S = 1.04	Δρ_max = 2.38 e Å⁻³
6153 reflections	Δρ_min = −1.53 e Å⁻³
361 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Pb1	0.49390 (3)	0.79973 (2)	0.293309 (10)	0.01922 (7)
Pb2	0.07338 (3)	0.681658 (19)	0.205959 (10)	0.01888 (7)
O1	0.3686 (6)	0.5548 (4)	0.2779 (2)	0.0249 (9)
O2	0.6821 (6)	0.5951 (4)	0.2572 (2)	0.0245 (9)
O3	0.7606 (6)	−0.1078 (4)	0.2138 (2)	0.0220 (8)
O4	1.0651 (6)	−0.0907 (4)	0.2364 (2)	0.0294 (10)
O5	0.8092 (6)	0.7332 (4)	0.3482 (2)	0.0248 (9)
O6	0.5560 (6)	0.6398 (5)	0.4009 (2)	0.0306 (10)
O7	0.3786 (6)	0.7598 (4)	0.1514 (2)	0.0282 (9)
O8	0.1058 (6)	0.8232 (4)	0.0934 (2)	0.0294 (10)
O9	0.4368 (8)	0.9887 (5)	0.3696 (3)	0.0462 (13)
O10	0.1395 (8)	0.4857 (5)	0.1317 (3)	0.0397 (12)
C1	0.6404 (8)	0.3726 (5)	0.2533 (3)	0.0211 (12)
C2	0.8410 (9)	0.3127 (6)	0.2657 (3)	0.0257 (13)
H2A	0.9255	0.3641	0.2786	0.031*
C3	0.9179 (9)	0.1773 (6)	0.2592 (3)	0.0251 (13)
H3A	1.0531	0.1354	0.2690	0.030*
C4	0.7941 (8)	0.1038 (5)	0.2381 (3)	0.0191 (11)
C5	0.5969 (9)	0.1660 (6)	0.2233 (3)	0.0237 (12)
H5A	0.5155	0.1169	0.2072	0.028*
C6	0.5179 (9)	0.2987 (6)	0.2316 (3)	0.0241 (12)
H6A	0.3817	0.3394	0.2227	0.029*
C7	0.5572 (9)	0.5174 (5)	0.2632 (3)	0.0206 (11)
C8	0.8810 (9)	−0.0405 (6)	0.2293 (3)	0.0206 (11)
C9	0.8759 (9)	0.5726 (6)	0.4494 (3)	0.0211 (11)
C10	1.0735 (9)	0.5929 (6)	0.4484 (3)	0.0270 (13)
H10A	1.1236	0.6555	0.4133	0.032*
C11	0.7381 (9)	0.6534 (6)	0.3962 (3)	0.0231 (12)
C12	0.8054 (9)	0.4786 (6)	0.5013 (3)	0.0238 (12)
H12A	0.6722	0.4640	0.5018	0.029*
C13	0.2876 (9)	0.8267 (6)	0.1006 (3)	0.0228 (12)
C14	0.3981 (8)	0.9159 (5)	0.0480 (3)	0.0205 (11)
C15	0.5835 (8)	0.9424 (6)	0.0614 (3)	0.0216 (12)
H15A	0.6399	0.9026	0.1029	0.026*
C16	0.3171 (8)	0.9733 (6)	−0.0138 (3)	0.0226 (12)
H16A	0.1938	0.9544	−0.0230	0.027*
C17	0.5294 (12)	1.0507 (7)	0.3975 (3)	0.0365 (16)
C18	0.7348 (12)	0.9995 (7)	0.4256 (4)	0.0421 (17)
H18A	0.7333	0.9176	0.4605	0.050*
H18B	0.8398	0.9759	0.3897	0.050*
C19	0.7776 (14)	1.1124 (10)	0.4549 (5)	0.065 (3)
H19A	0.9021	1.1409	0.4325	0.079*
H19B	0.7954	1.0826	0.5033	0.079*
C20	0.5956 (13)	1.2285 (8)	0.4433 (4)	0.0471 (19)
H20A	0.5307	1.2525	0.4864	0.057*
H20B	0.6363	1.3099	0.4152	0.057*
C21	0.2615 (12)	1.2598 (8)	0.3909 (4)	0.0442 (18)
H21A	0.1928	1.2076	0.3691	0.066*
H21B	0.2799	1.3432	0.3600	0.066*
H21C	0.1795	1.2834	0.4311	0.066*
C22	−0.0052 (11)	0.4676 (7)	0.1046 (3)	0.0350 (15)
C23	−0.1965 (10)	0.5733 (7)	0.0896 (4)	0.0381 (16)
H23A	−0.2691	0.5997	0.1313	0.046*
H23B	−0.1648	0.6556	0.0595	0.046*
C24	−0.3207 (14)	0.5057 (10)	0.0563 (4)	0.060 (2)
H24A	−0.3416	0.5545	0.0099	0.072*
H24B	−0.4545	0.5058	0.0811	0.072*
C25	−0.2025 (14)	0.3580 (10)	0.0561 (4)	0.057 (2)
H25A	−0.2762	0.2916	0.0844	0.068*
H25B	−0.1780	0.3379	0.0101	0.068*
C26	0.1454 (15)	0.2341 (8)	0.0906 (5)	0.062 (3)
H26A	0.2605	0.2524	0.1094	0.093*
H26B	0.1886	0.2087	0.0466	0.093*
H26C	0.0950	0.1595	0.1205	0.093*
N1	0.4575 (9)	1.1788 (6)	0.4093 (3)	0.0355 (13)
N2	−0.0156 (11)	0.3562 (6)	0.0834 (3)	0.0448 (15)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.01844 (12)	0.01974 (11)	0.01939 (12)	−0.00224 (8)	−0.00335 (8)	−0.00412 (8)
Pb2	0.01798 (12)	0.01763 (11)	0.02114 (12)	−0.00417 (8)	−0.00126 (8)	−0.00327 (8)
O1	0.019 (2)	0.024 (2)	0.028 (2)	0.0010 (16)	−0.0018 (17)	−0.0013 (17)
O2	0.023 (2)	0.0189 (19)	0.032 (2)	−0.0030 (16)	−0.0017 (17)	−0.0068 (17)
O3	0.024 (2)	0.0224 (19)	0.023 (2)	−0.0090 (17)	−0.0032 (16)	−0.0054 (16)
O4	0.024 (2)	0.022 (2)	0.043 (3)	−0.0011 (18)	−0.0036 (19)	−0.0104 (19)
O5	0.025 (2)	0.028 (2)	0.018 (2)	−0.0050 (17)	−0.0075 (16)	0.0043 (17)
O6	0.023 (2)	0.045 (3)	0.022 (2)	−0.010 (2)	−0.0072 (17)	0.0041 (19)
O7	0.025 (2)	0.033 (2)	0.021 (2)	−0.0061 (18)	−0.0024 (17)	0.0083 (18)
O8	0.025 (2)	0.038 (2)	0.025 (2)	−0.0110 (19)	−0.0041 (17)	0.0025 (19)
O9	0.056 (3)	0.043 (3)	0.050 (3)	−0.018 (3)	−0.002 (3)	−0.025 (3)
O10	0.042 (3)	0.047 (3)	0.035 (3)	−0.006 (2)	−0.010 (2)	−0.019 (2)
C1	0.020 (3)	0.019 (3)	0.022 (3)	0.000 (2)	0.000 (2)	−0.005 (2)
C2	0.023 (3)	0.024 (3)	0.032 (3)	−0.007 (2)	−0.004 (2)	−0.006 (3)
C3	0.020 (3)	0.026 (3)	0.029 (3)	−0.001 (2)	0.001 (2)	−0.008 (2)
C4	0.022 (3)	0.019 (3)	0.015 (3)	−0.004 (2)	−0.003 (2)	0.000 (2)
C5	0.025 (3)	0.025 (3)	0.025 (3)	−0.010 (2)	−0.005 (2)	−0.004 (2)
C6	0.026 (3)	0.023 (3)	0.023 (3)	−0.003 (2)	−0.006 (2)	−0.004 (2)
C7	0.024 (3)	0.019 (3)	0.017 (3)	−0.002 (2)	−0.003 (2)	−0.001 (2)
C8	0.022 (3)	0.022 (3)	0.016 (3)	−0.003 (2)	0.001 (2)	−0.003 (2)
C9	0.021 (3)	0.025 (3)	0.017 (3)	−0.005 (2)	−0.002 (2)	−0.005 (2)
C10	0.029 (3)	0.031 (3)	0.021 (3)	−0.011 (3)	−0.003 (2)	0.003 (2)
C11	0.026 (3)	0.029 (3)	0.016 (3)	−0.007 (2)	−0.002 (2)	−0.008 (2)
C12	0.019 (3)	0.031 (3)	0.022 (3)	−0.008 (2)	−0.006 (2)	0.000 (2)
C13	0.024 (3)	0.021 (3)	0.021 (3)	−0.001 (2)	0.002 (2)	−0.003 (2)
C14	0.020 (3)	0.019 (3)	0.020 (3)	−0.001 (2)	0.001 (2)	−0.001 (2)
C15	0.019 (3)	0.027 (3)	0.016 (3)	−0.001 (2)	−0.004 (2)	0.000 (2)
C16	0.016 (3)	0.028 (3)	0.024 (3)	−0.002 (2)	−0.005 (2)	−0.008 (2)
C17	0.056 (5)	0.036 (4)	0.021 (3)	−0.019 (3)	0.005 (3)	−0.006 (3)
C18	0.052 (5)	0.040 (4)	0.032 (4)	−0.005 (3)	0.004 (3)	−0.010 (3)
C19	0.049 (5)	0.086 (7)	0.076 (7)	−0.024 (5)	−0.003 (5)	−0.036 (6)
C20	0.063 (5)	0.052 (4)	0.039 (4)	−0.027 (4)	0.002 (4)	−0.023 (4)
C21	0.053 (5)	0.048 (4)	0.036 (4)	−0.017 (4)	0.008 (3)	−0.015 (3)
C22	0.046 (4)	0.038 (4)	0.023 (3)	−0.015 (3)	0.006 (3)	−0.007 (3)
C23	0.033 (4)	0.047 (4)	0.030 (4)	−0.001 (3)	−0.003 (3)	−0.004 (3)
C24	0.059 (6)	0.090 (7)	0.040 (5)	−0.023 (5)	−0.009 (4)	−0.024 (5)
C25	0.073 (6)	0.086 (7)	0.030 (4)	−0.050 (5)	0.005 (4)	−0.021 (4)
C26	0.089 (7)	0.036 (4)	0.050 (5)	0.004 (4)	0.005 (5)	−0.008 (4)
N1	0.045 (4)	0.036 (3)	0.032 (3)	−0.019 (3)	0.003 (3)	−0.014 (3)
N2	0.067 (4)	0.040 (3)	0.031 (3)	−0.016 (3)	0.000 (3)	−0.010 (3)

Geometric parameters (Å, º) top

Pb1—O2	2.381 (4)	C10—C12^v	1.365 (8)
Pb1—O5	2.410 (4)	C10—H10A	0.9400
Pb1—O6	2.461 (4)	C12—C10^v	1.365 (8)
Pb1—O3ⁱ	2.486 (4)	C12—H12A	0.9400
Pb1—O9	2.633 (5)	C13—C14	1.496 (8)
Pb1—C11	2.779 (6)	C14—C16	1.388 (8)
Pb2—O7	2.434 (4)	C14—C15	1.400 (8)
Pb2—O8	2.456 (4)	C15—C16^vi	1.374 (8)
Pb2—O4ⁱⁱ	2.494 (4)	C15—H15A	0.9400
Pb2—O1	2.552 (4)	C16—C15^vi	1.374 (8)
Pb2—O10	2.657 (5)	C16—H16A	0.9400
Pb2—O3ⁱⁱ	2.660 (4)	C17—N1	1.341 (8)
Pb2—C13	2.791 (6)	C17—C18	1.500 (10)
O1—C7	1.260 (7)	C18—C19	1.485 (11)
O2—C7	1.256 (7)	C18—H18A	0.9800
O3—C8	1.271 (7)	C18—H18B	0.9800
O3—Pb1ⁱⁱⁱ	2.486 (4)	C19—C20	1.503 (12)
O3—Pb2^iv	2.660 (4)	C19—H19A	0.9800
O4—C8	1.243 (7)	C19—H19B	0.9800
O4—Pb2^iv	2.494 (4)	C20—N1	1.445 (9)
O5—C11	1.257 (7)	C20—H20A	0.9800
O6—C11	1.255 (7)	C20—H20B	0.9800
O7—C13	1.256 (7)	C21—N1	1.437 (10)
O8—C13	1.259 (7)	C21—H21A	0.9700
O9—C17	1.224 (8)	C21—H21B	0.9700
O10—C22	1.236 (8)	C21—H21C	0.9700
C1—C2	1.381 (8)	C22—N2	1.306 (9)
C1—C6	1.388 (8)	C22—C23	1.499 (9)
C1—C7	1.496 (7)	C23—C24	1.482 (10)
C2—C3	1.384 (8)	C23—H23A	0.9800
C2—H2A	0.9400	C23—H23B	0.9800
C3—C4	1.386 (8)	C24—C25	1.533 (13)
C3—H3A	0.9400	C24—H24A	0.9800
C4—C5	1.377 (8)	C24—H24B	0.9800
C4—C8	1.488 (7)	C25—N2	1.427 (10)
C5—C6	1.369 (8)	C25—H25A	0.9800
C5—H5A	0.9400	C25—H25B	0.9800
C6—H6A	0.9400	C26—N2	1.448 (10)
C9—C10	1.388 (8)	C26—H26A	0.9700
C9—C12	1.388 (8)	C26—H26B	0.9700
C9—C11	1.495 (8)	C26—H26C	0.9700

O2—Pb1—O5	72.48 (14)	O6—C11—Pb1	62.3 (3)
O2—Pb1—O6	77.41 (15)	O5—C11—Pb1	60.0 (3)
O5—Pb1—O6	53.70 (13)	C9—C11—Pb1	177.6 (4)
O2—Pb1—O3ⁱ	79.52 (13)	C10^v—C12—C9	121.0 (5)
O5—Pb1—O3ⁱ	72.31 (13)	C10^v—C12—H12A	119.5
O6—Pb1—O3ⁱ	125.39 (13)	C9—C12—H12A	119.5
O2—Pb1—O9	152.10 (16)	O7—C13—O8	122.0 (5)
O5—Pb1—O9	79.82 (16)	O7—C13—C14	118.7 (5)
O6—Pb1—O9	83.63 (16)	O8—C13—C14	119.3 (5)
O3ⁱ—Pb1—O9	95.47 (15)	O7—C13—Pb2	60.6 (3)
O2—Pb1—C11	72.56 (15)	O8—C13—Pb2	61.6 (3)
O5—Pb1—C11	26.86 (15)	C14—C13—Pb2	174.3 (4)
O6—Pb1—C11	26.85 (15)	C16—C14—C15	119.8 (5)
O3ⁱ—Pb1—C11	98.80 (15)	C16—C14—C13	120.4 (5)
O9—Pb1—C11	81.26 (17)	C15—C14—C13	119.8 (5)
O7—Pb2—O8	53.45 (13)	C16^vi—C15—C14	119.9 (5)
O7—Pb2—O4ⁱⁱ	72.48 (14)	C16^vi—C15—H15A	120.1
O8—Pb2—O4ⁱⁱ	79.12 (15)	C14—C15—H15A	120.1
O7—Pb2—O1	72.97 (13)	C15^vi—C16—C14	120.3 (5)
O8—Pb2—O1	125.62 (13)	C15^vi—C16—H16A	119.8
O4ⁱⁱ—Pb2—O1	94.54 (13)	C14—C16—H16A	119.8
O7—Pb2—O10	90.42 (15)	O9—C17—N1	124.3 (7)
O8—Pb2—O10	80.92 (15)	O9—C17—C18	127.7 (7)
O4ⁱⁱ—Pb2—O10	159.02 (16)	N1—C17—C18	108.0 (6)
O1—Pb2—O10	91.84 (14)	C19—C18—C17	106.8 (6)
O7—Pb2—O3ⁱⁱ	111.17 (13)	C19—C18—H18A	110.4
O8—Pb2—O3ⁱⁱ	78.39 (13)	C17—C18—H18A	110.4
O4ⁱⁱ—Pb2—O3ⁱⁱ	50.44 (12)	C19—C18—H18B	110.4
O1—Pb2—O3ⁱⁱ	136.11 (13)	C17—C18—H18B	110.4
O10—Pb2—O3ⁱⁱ	130.70 (13)	H18A—C18—H18B	108.6
O7—Pb2—C13	26.71 (15)	C18—C19—C20	106.0 (7)
O8—Pb2—C13	26.80 (15)	C18—C19—H19A	110.5
O4ⁱⁱ—Pb2—C13	72.88 (16)	C20—C19—H19A	110.5
O1—Pb2—C13	99.48 (15)	C18—C19—H19B	110.5
O10—Pb2—C13	86.36 (16)	C20—C19—H19B	110.5
O3ⁱⁱ—Pb2—C13	94.22 (14)	H19A—C19—H19B	108.7
C7—O1—Pb2	132.2 (4)	N1—C20—C19	105.6 (6)
C7—O2—Pb1	105.6 (3)	N1—C20—H20A	110.6
C8—O3—Pb1ⁱⁱⁱ	124.5 (4)	C19—C20—H20A	110.6
C8—O3—Pb2^iv	89.4 (3)	N1—C20—H20B	110.6
Pb1ⁱⁱⁱ—O3—Pb2^iv	106.20 (13)	C19—C20—H20B	110.6
C8—O4—Pb2^iv	97.9 (3)	H20A—C20—H20B	108.7
C11—O5—Pb1	93.2 (3)	N1—C21—H21A	109.5
C11—O6—Pb1	90.9 (3)	N1—C21—H21B	109.5
C13—O7—Pb2	92.7 (3)	H21A—C21—H21B	109.5
C13—O8—Pb2	91.6 (3)	N1—C21—H21C	109.5
C17—O9—Pb1	142.2 (5)	H21A—C21—H21C	109.5
C22—O10—Pb2	118.8 (4)	H21B—C21—H21C	109.5
C2—C1—C6	120.0 (5)	O10—C22—N2	126.1 (7)
C2—C1—C7	119.5 (5)	O10—C22—C23	124.7 (6)
C6—C1—C7	120.5 (5)	N2—C22—C23	109.2 (6)
C1—C2—C3	120.1 (5)	C24—C23—C22	104.9 (7)
C1—C2—H2A	119.9	C24—C23—H23A	110.8
C3—C2—H2A	119.9	C22—C23—H23A	110.8
C2—C3—C4	119.5 (5)	C24—C23—H23B	110.8
C2—C3—H3A	120.3	C22—C23—H23B	110.8
C4—C3—H3A	120.3	H23A—C23—H23B	108.8
C5—C4—C3	120.0 (5)	C23—C24—C25	107.0 (7)
C5—C4—C8	121.2 (5)	C23—C24—H24A	110.3
C3—C4—C8	118.8 (5)	C25—C24—H24A	110.3
C6—C5—C4	120.9 (5)	C23—C24—H24B	110.3
C6—C5—H5A	119.6	C25—C24—H24B	110.3
C4—C5—H5A	119.6	H24A—C24—H24B	108.6
C5—C6—C1	119.5 (5)	N2—C25—C24	102.9 (6)
C5—C6—H6A	120.3	N2—C25—H25A	111.2
C1—C6—H6A	120.3	C24—C25—H25A	111.2
O2—C7—O1	123.4 (5)	N2—C25—H25B	111.2
O2—C7—C1	117.4 (5)	C24—C25—H25B	111.2
O1—C7—C1	119.2 (5)	H25A—C25—H25B	109.1
O4—C8—O3	122.3 (5)	N2—C26—H26A	109.5
O4—C8—C4	120.4 (5)	N2—C26—H26B	109.5
O3—C8—C4	117.4 (5)	H26A—C26—H26B	109.5
C10—C9—C12	119.3 (5)	N2—C26—H26C	109.5
C10—C9—C11	120.5 (5)	H26A—C26—H26C	109.5
C12—C9—C11	120.1 (5)	H26B—C26—H26C	109.5
C12^v—C10—C9	119.6 (6)	C17—N1—C21	123.9 (6)
C12^v—C10—H10A	120.2	C17—N1—C20	113.6 (6)
C9—C10—H10A	120.2	C21—N1—C20	122.5 (6)
O6—C11—O5	122.3 (5)	C22—N2—C25	115.8 (7)
O6—C11—C9	119.2 (5)	C22—N2—C26	122.9 (7)
O5—C11—C9	118.6 (5)	C25—N2—C26	121.2 (7)

O7—Pb2—O1—C7	−29.7 (5)	C3—C4—C8—O3	176.0 (5)
O8—Pb2—O1—C7	−20.0 (5)	C12—C9—C10—C12^v	−0.7 (10)
O4ⁱⁱ—Pb2—O1—C7	−99.9 (5)	C11—C9—C10—C12^v	177.8 (5)
O10—Pb2—O1—C7	60.1 (5)	Pb1—O6—C11—O5	2.2 (6)
O3ⁱⁱ—Pb2—O1—C7	−132.8 (4)	Pb1—O6—C11—C9	−177.9 (5)
C13—Pb2—O1—C7	−26.5 (5)	Pb1—O5—C11—O6	−2.2 (6)
O5—Pb1—O2—C7	132.5 (4)	Pb1—O5—C11—C9	177.9 (4)
O6—Pb1—O2—C7	76.9 (4)	C10—C9—C11—O6	−175.2 (6)
O3ⁱ—Pb1—O2—C7	−153.0 (4)	C12—C9—C11—O6	3.2 (8)
O9—Pb1—O2—C7	125.2 (4)	C10—C9—C11—O5	4.7 (8)
C11—Pb1—O2—C7	104.3 (4)	C12—C9—C11—O5	−176.8 (5)
O2—Pb1—O5—C11	−85.8 (3)	O2—Pb1—C11—O6	−96.6 (4)
O6—Pb1—O5—C11	1.2 (3)	O5—Pb1—C11—O6	177.9 (6)
O3ⁱ—Pb1—O5—C11	−170.1 (4)	O3ⁱ—Pb1—C11—O6	−172.6 (3)
O9—Pb1—O5—C11	90.7 (4)	O9—Pb1—C11—O6	93.2 (4)
O2—Pb1—O6—C11	76.2 (3)	O2—Pb1—C11—O5	85.5 (3)
O5—Pb1—O6—C11	−1.2 (3)	O6—Pb1—C11—O5	−177.9 (6)
O3ⁱ—Pb1—O6—C11	9.0 (4)	O3ⁱ—Pb1—C11—O5	9.5 (3)
O9—Pb1—O6—C11	−83.2 (4)	O9—Pb1—C11—O5	−84.7 (3)
O8—Pb2—O7—C13	2.7 (3)	C10—C9—C12—C10^v	0.7 (10)
O4ⁱⁱ—Pb2—O7—C13	−86.6 (3)	C11—C9—C12—C10^v	−177.8 (6)
O1—Pb2—O7—C13	172.8 (4)	Pb2—O7—C13—O8	−5.0 (6)
O10—Pb2—O7—C13	81.0 (3)	Pb2—O7—C13—C14	173.6 (4)
O3ⁱⁱ—Pb2—O7—C13	−53.6 (4)	Pb2—O8—C13—O7	4.9 (6)
O7—Pb2—O8—C13	−2.7 (3)	Pb2—O8—C13—C14	−173.6 (5)
O4ⁱⁱ—Pb2—O8—C13	73.5 (3)	O8—Pb2—C13—O7	−175.2 (6)
O1—Pb2—O8—C13	−14.3 (4)	O4ⁱⁱ—Pb2—C13—O7	84.9 (3)
O10—Pb2—O8—C13	−100.0 (4)	O1—Pb2—C13—O7	−6.9 (4)
O3ⁱⁱ—Pb2—O8—C13	125.0 (4)	O10—Pb2—C13—O7	−98.2 (3)
O2—Pb1—O9—C17	33.1 (10)	O3ⁱⁱ—Pb2—C13—O7	131.2 (3)
O5—Pb1—O9—C17	26.1 (8)	O7—Pb2—C13—O8	175.2 (6)
O6—Pb1—O9—C17	80.3 (8)	O4ⁱⁱ—Pb2—C13—O8	−99.9 (4)
O3ⁱ—Pb1—O9—C17	−44.8 (8)	O1—Pb2—C13—O8	168.3 (3)
C11—Pb1—O9—C17	53.3 (8)	O10—Pb2—C13—O8	77.0 (3)
O7—Pb2—O10—C22	−134.2 (5)	O3ⁱⁱ—Pb2—C13—O8	−53.6 (3)
O8—Pb2—O10—C22	−81.4 (5)	O7—C13—C14—C16	169.3 (5)
O4ⁱⁱ—Pb2—O10—C22	−99.5 (6)	O8—C13—C14—C16	−12.2 (8)
O1—Pb2—O10—C22	152.8 (5)	O7—C13—C14—C15	−11.3 (8)
O3ⁱⁱ—Pb2—O10—C22	−15.4 (6)	O8—C13—C14—C15	167.3 (5)
C13—Pb2—O10—C22	−107.8 (5)	C16—C14—C15—C16^vi	1.0 (9)
C6—C1—C2—C3	−2.6 (9)	C13—C14—C15—C16^vi	−178.5 (5)
C7—C1—C2—C3	177.5 (5)	C15—C14—C16—C15^vi	−1.0 (9)
C1—C2—C3—C4	2.0 (9)	C13—C14—C16—C15^vi	178.5 (5)
C2—C3—C4—C5	0.6 (9)	Pb1—O9—C17—N1	150.4 (6)
C2—C3—C4—C8	178.1 (5)	Pb1—O9—C17—C18	−31.4 (12)
C3—C4—C5—C6	−2.6 (9)	O9—C17—C18—C19	−179.1 (8)
C8—C4—C5—C6	179.9 (5)	N1—C17—C18—C19	−0.6 (8)
C4—C5—C6—C1	2.0 (9)	C17—C18—C19—C20	0.0 (9)
C2—C1—C6—C5	0.6 (9)	C18—C19—C20—N1	0.6 (9)
C7—C1—C6—C5	−179.6 (5)	Pb2—O10—C22—N2	−159.4 (6)
Pb1—O2—C7—O1	7.5 (7)	Pb2—O10—C22—C23	22.1 (9)
Pb1—O2—C7—C1	−171.6 (4)	O10—C22—C23—C24	178.9 (7)
Pb2—O1—C7—O2	83.5 (7)	N2—C22—C23—C24	0.1 (8)
Pb2—O1—C7—C1	−97.5 (6)	C22—C23—C24—C25	3.0 (9)
C2—C1—C7—O2	26.5 (8)	C23—C24—C25—N2	−4.8 (9)
C6—C1—C7—O2	−153.3 (6)	O9—C17—N1—C21	0.0 (11)
C2—C1—C7—O1	−152.6 (6)	C18—C17—N1—C21	−178.5 (6)
C6—C1—C7—O1	27.6 (8)	O9—C17—N1—C20	179.6 (7)
Pb2^iv—O4—C8—O3	2.6 (6)	C18—C17—N1—C20	1.1 (8)
Pb2^iv—O4—C8—C4	−176.6 (4)	C19—C20—N1—C17	−1.1 (9)
Pb1ⁱⁱⁱ—O3—C8—O4	106.9 (6)	C19—C20—N1—C21	178.5 (7)
Pb2^iv—O3—C8—O4	−2.4 (6)	O10—C22—N2—C25	177.7 (7)
Pb1ⁱⁱⁱ—O3—C8—C4	−73.9 (6)	C23—C22—N2—C25	−3.6 (9)
Pb2^iv—O3—C8—C4	176.8 (4)	O10—C22—N2—C26	1.5 (12)
C5—C4—C8—O4	172.7 (6)	C23—C22—N2—C26	−179.8 (7)
C3—C4—C8—O4	−4.8 (8)	C24—C25—N2—C22	5.3 (9)
C5—C4—C8—O3	−6.5 (8)	C24—C25—N2—C26	−178.4 (7)

Symmetry codes: (i) x, y+1, z; (ii) x−1, y+1, z; (iii) x, y−1, z; (iv) x+1, y−1, z; (v) −x+2, −y+1, −z+1; (vi) −x+1, −y+2, −z.

Experimental details

Crystal data
Chemical formula	[Pb₂(C₈H₄O₄)₂(C₅H₉NO)₂]
M_r	940.87
Crystal system, space group	Triclinic, P1
Temperature (K)	223
a, b, c (Å)	6.7327 (11), 10.1503 (17), 20.249 (3)
α, β, γ (°)	78.521 (3), 83.357 (3), 77.113 (3)
V (Å³)	1318.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	12.82
Crystal size (mm)	0.18 × 0.10 × 0.03

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.206, 0.700
No. of measured, independent and observed [I > 2σ(I)] reflections	15362, 6153, 5400
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.674

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.079, 1.04
No. of reflections	6153
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.38, −1.53

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97.

Selected geometric parameters (Å, º) top

Pb1—O2	2.381 (4)	Pb2—O4ⁱⁱ	2.494 (4)
Pb1—O5	2.410 (4)	Pb2—O1	2.552 (4)
Pb1—O6	2.461 (4)	Pb2—O10	2.657 (5)
Pb1—O3ⁱ	2.486 (4)	Pb2—O3ⁱⁱ	2.660 (4)
Pb1—O9	2.633 (5)	O3—Pb1ⁱⁱⁱ	2.486 (4)
Pb2—O7	2.434 (4)	O3—Pb2^iv	2.660 (4)
Pb2—O8	2.456 (4)	O4—Pb2^iv	2.494 (4)

O2—Pb1—O5	72.48 (14)	O7—Pb2—O1	72.97 (13)
O2—Pb1—O6	77.41 (15)	O8—Pb2—O1	125.62 (13)
O5—Pb1—O6	53.70 (13)	O4ⁱⁱ—Pb2—O1	94.54 (13)
O2—Pb1—O3ⁱ	79.52 (13)	O7—Pb2—O10	90.42 (15)
O5—Pb1—O3ⁱ	72.31 (13)	O8—Pb2—O10	80.92 (15)
O6—Pb1—O3ⁱ	125.39 (13)	O4ⁱⁱ—Pb2—O10	159.02 (16)
O2—Pb1—O9	152.10 (16)	O1—Pb2—O10	91.84 (14)
O5—Pb1—O9	79.82 (16)	O7—Pb2—O3ⁱⁱ	111.17 (13)
O6—Pb1—O9	83.63 (16)	O8—Pb2—O3ⁱⁱ	78.39 (13)
O3ⁱ—Pb1—O9	95.47 (15)	O4ⁱⁱ—Pb2—O3ⁱⁱ	50.44 (12)
O7—Pb2—O8	53.45 (13)	O1—Pb2—O3ⁱⁱ	136.11 (13)
O7—Pb2—O4ⁱⁱ	72.48 (14)	O10—Pb2—O3ⁱⁱ	130.70 (13)
O8—Pb2—O4ⁱⁱ	79.12 (15)

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

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