A one-dimensional lead(II) coordination polymer with terminal and bridging 5-carb­oxy-2-(pyridin-3-yl)-1H-imidazole-4-carboxyl­ate ligands

In the coordination polymer catena-poly[[[di­aqua­[5-carb­oxy-2-(pyridin-3-yl)-1H-imidazole-4-carboxyl­ato-κ²N³,O⁴]lead(II)]-μ-5-carb­oxy-2-(pyridin-3-yl)-1H-imidazole-4-car­boxyl­ato-κ³N³,O⁴:N²] dihydrate], {[Pb(C₁₀H₆N₃O₄)(H₂O)₂]·2H₂O}_n, the two 5-carb­oxy-2-(pyridin-3-yl)-1H-imid­azole-4-car­boxyl­ate ligands have different coordination modes, one being terminal and the other bridging. The bridging ligand links Pb^II cations into one-dimensional coordination polymer chains. The structure is also stabilized by intra- and interchain π–π stacking inter­actions between the pyridine rings, resulting in the formation of a two-dimensional network. Extensive hydrogen-bonding inter­actions lead to the formation of a three-dimensional supra­molecular network.

Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004); data reduction: APEX2 (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009).

catena-Poly[[[diaqua[5-carboxy-2-(pyridin-3-yl)-1H-imidazole-4-carboxylato-κ²N³,O⁴]lead(II)]-µ-5-carboxy-2-(pyridin-3-yl)-1H-imidazole-4-carboxylato-κ³N³,O⁴:N²] dihydrate]

Crystal data

[Pb(C10H6N3O4)(H2O)2]·2H2O	F(000) = 1440
Mr = 743.61	Dx = 2.098 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4388 reflections
a = 7.1384 (19) Å	θ = 1.6–25.5°
b = 18.424 (5) Å	µ = 7.25 mm^−1
c = 17.907 (5) Å	T = 296 K
β = 90.984 (3)°	Block, colourless
V = 2354.7 (11) Å^3	0.20 × 0.13 × 0.12 mm
Z = 4

Data collection

Bruker APEXII CCD area-detector diffractometer	4388 independent reflections
Radiation source: fine-focus sealed tube	3354 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
φ and ω scans	θmax = 25.5°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −8→8
Tmin = 0.336, Tmax = 0.419	k = −21→22
12273 measured reflections	l = −16→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.074	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.026P)^2] where P = (Fo^2 + 2Fc^2)/3
4388 reflections	(Δ/σ)max = 0.001
352 parameters	Δρmax = 0.69 e Å^−3
0 restraints	Δρmin = −0.76 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	−0.1116 (8)	0.2065 (3)	0.7557 (3)	0.0370 (15)
H1	−0.1490	0.1739	0.7922	0.044*
C2	−0.1344 (8)	0.1868 (3)	0.6830 (3)	0.0362 (15)
H2	−0.1841	0.1418	0.6700	0.043*
C3	−0.0816 (8)	0.2357 (3)	0.6290 (3)	0.0331 (14)
H3	−0.1003	0.2246	0.5787	0.040*
C4	−0.0007 (7)	0.3013 (3)	0.6492 (3)	0.0257 (13)
C5	0.0148 (8)	0.3162 (3)	0.7248 (3)	0.0330 (14)
H5	0.0650	0.3606	0.7395	0.040*
C6	0.0665 (7)	0.3512 (3)	0.5926 (3)	0.0276 (13)
C7	0.1822 (7)	0.4492 (3)	0.5405 (3)	0.0307 (13)
C8	0.1608 (7)	0.3948 (3)	0.4885 (3)	0.0277 (13)
C9	0.2551 (9)	0.5245 (4)	0.5371 (4)	0.0436 (16)
C10	0.1992 (8)	0.3951 (3)	0.4072 (3)	0.0323 (14)
C11	0.4941 (8)	0.3120 (4)	0.7001 (4)	0.0448 (17)
H11	0.5304	0.3537	0.7258	0.054*
C12	0.5061 (8)	0.3113 (3)	0.6237 (4)	0.0407 (16)
H12	0.5485	0.3520	0.5983	0.049*
C13	0.4545 (8)	0.2496 (4)	0.5851 (3)	0.0358 (14)
H13	0.4636	0.2476	0.5334	0.043*
C14	0.3883 (7)	0.1901 (3)	0.6252 (3)	0.0301 (13)
C15	0.3789 (7)	0.1961 (3)	0.7018 (3)	0.0312 (13)
H15	0.3330	0.1568	0.7285	0.037*
C16	0.3317 (7)	0.1245 (3)	0.5848 (3)	0.0280 (13)
C17	0.2367 (7)	0.0534 (3)	0.4959 (3)	0.0301 (13)
C18	0.2985 (8)	0.0096 (3)	0.5548 (3)	0.0304 (13)
C19	0.3181 (9)	−0.0700 (3)	0.5648 (4)	0.0425 (16)
C20	0.1596 (8)	0.0329 (4)	0.4217 (3)	0.0360 (14)
N1	−0.0390 (7)	0.2696 (2)	0.7780 (3)	0.0345 (12)
N2	0.1197 (6)	0.4209 (2)	0.6059 (3)	0.0316 (11)
H2N	0.1236	0.4397	0.6480	0.038*
N3	0.0905 (6)	0.3341 (2)	0.5216 (2)	0.0284 (11)
N4	0.4320 (7)	0.2549 (3)	0.7396 (3)	0.0390 (13)
N5	0.2556 (6)	0.1259 (2)	0.5162 (3)	0.0316 (11)
N6	0.3585 (6)	0.0560 (3)	0.6093 (3)	0.0340 (12)
H6N	0.4046	0.0437	0.6522	0.041*
O1	0.2592 (7)	0.5621 (2)	0.5944 (3)	0.0561 (13)
O2	0.3101 (6)	0.5489 (2)	0.4732 (3)	0.0538 (12)
H2O	0.2938	0.5177	0.4410	0.081*
O3	0.1665 (6)	0.3398 (2)	0.3699 (2)	0.0455 (11)
O4	0.2593 (6)	0.4542 (2)	0.3774 (2)	0.0501 (12)
O5	0.2567 (6)	−0.1103 (2)	0.5102 (3)	0.0538 (12)
H5O	0.2212	−0.0864	0.4731	0.081*
O6	0.3889 (7)	−0.0936 (2)	0.6220 (3)	0.0652 (14)
O7	0.1055 (6)	0.0812 (2)	0.3783 (2)	0.0426 (11)
O8	0.1547 (6)	−0.0346 (2)	0.4057 (2)	0.0484 (11)
O1W	0.3894 (6)	0.2166 (2)	0.3841 (2)	0.0434 (11)
H1W	0.3894	0.2253	0.3327	0.065*
H2W	0.4371	0.1769	0.3948	0.065*
O2W	−0.2769 (6)	0.2889 (2)	0.4319 (3)	0.0536 (12)
H3W	−0.3476	0.2767	0.3994	0.080*
H4W	−0.2614	0.3326	0.4278	0.080*
O3W	0.9418 (7)	0.4977 (3)	0.2633 (2)	0.0673 (15)
H5W	0.9615	0.5154	0.2237	0.101*
H6W	1.0274	0.4737	0.2752	0.101*
O4W	0.5229 (7)	0.4664 (3)	0.2536 (2)	0.0877 (19)
H7W	0.4656	0.5006	0.2754	0.105*
H8W	0.6344	0.4771	0.2494	0.132*
Pb1	0.05323 (3)	0.219656 (12)	0.419947 (12)	0.03447 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.052 (4)	0.031 (4)	0.028 (4)	−0.007 (3)	0.001 (3)	−0.003 (3)
C2	0.048 (4)	0.025 (3)	0.036 (4)	−0.007 (3)	0.004 (3)	−0.007 (3)
C3	0.038 (3)	0.037 (4)	0.024 (3)	−0.006 (3)	0.003 (3)	−0.007 (3)
C4	0.027 (3)	0.022 (3)	0.028 (3)	0.005 (2)	−0.003 (2)	0.001 (2)
C5	0.047 (4)	0.026 (3)	0.025 (3)	−0.010 (3)	−0.006 (3)	−0.004 (3)
C6	0.035 (3)	0.026 (3)	0.021 (3)	0.005 (3)	−0.003 (2)	−0.004 (3)
C7	0.032 (3)	0.026 (3)	0.033 (4)	0.005 (3)	−0.002 (3)	0.008 (3)
C8	0.029 (3)	0.026 (3)	0.028 (3)	−0.001 (2)	0.000 (2)	0.003 (3)
C9	0.045 (4)	0.040 (4)	0.046 (5)	−0.001 (3)	−0.001 (3)	0.005 (4)
C10	0.042 (3)	0.027 (3)	0.029 (4)	0.005 (3)	0.005 (3)	0.000 (3)
C11	0.039 (4)	0.042 (4)	0.054 (5)	−0.006 (3)	−0.002 (3)	−0.019 (4)
C12	0.038 (4)	0.030 (3)	0.054 (5)	−0.004 (3)	0.000 (3)	0.008 (3)
C13	0.035 (3)	0.043 (3)	0.029 (4)	0.001 (3)	−0.004 (3)	0.005 (3)
C14	0.029 (3)	0.035 (3)	0.027 (3)	0.001 (3)	0.000 (2)	−0.003 (3)
C15	0.038 (3)	0.033 (3)	0.023 (3)	0.000 (3)	0.000 (3)	−0.005 (3)
C16	0.033 (3)	0.032 (3)	0.020 (3)	0.005 (3)	0.003 (2)	−0.002 (3)
C17	0.030 (3)	0.035 (4)	0.024 (3)	0.003 (3)	0.002 (2)	−0.002 (3)
C18	0.037 (3)	0.030 (3)	0.025 (3)	0.002 (3)	0.007 (3)	0.000 (3)
C19	0.052 (4)	0.033 (4)	0.043 (4)	0.011 (3)	0.013 (3)	0.006 (3)
C20	0.033 (3)	0.043 (4)	0.032 (4)	−0.003 (3)	0.001 (3)	−0.007 (3)
N1	0.048 (3)	0.030 (3)	0.026 (3)	−0.006 (2)	−0.003 (2)	0.002 (2)
N2	0.045 (3)	0.032 (3)	0.018 (3)	−0.001 (2)	−0.006 (2)	0.001 (2)
N3	0.038 (3)	0.025 (3)	0.022 (3)	−0.003 (2)	−0.002 (2)	0.005 (2)
N4	0.043 (3)	0.042 (3)	0.033 (3)	0.001 (2)	0.001 (2)	−0.009 (3)
N5	0.037 (3)	0.026 (3)	0.032 (3)	−0.002 (2)	−0.004 (2)	0.000 (2)
N6	0.036 (3)	0.039 (3)	0.026 (3)	0.004 (2)	−0.006 (2)	0.005 (2)
O1	0.084 (4)	0.036 (3)	0.048 (3)	−0.012 (2)	−0.005 (3)	−0.002 (2)
O2	0.071 (3)	0.041 (3)	0.050 (3)	−0.015 (2)	0.006 (2)	0.012 (2)
O3	0.075 (3)	0.035 (3)	0.027 (2)	−0.003 (2)	0.009 (2)	0.000 (2)
O4	0.078 (3)	0.037 (3)	0.036 (3)	−0.003 (2)	0.012 (2)	0.013 (2)
O5	0.075 (3)	0.030 (3)	0.057 (3)	0.006 (2)	−0.006 (3)	−0.006 (2)
O6	0.099 (4)	0.040 (3)	0.057 (4)	0.021 (3)	−0.009 (3)	0.016 (3)
O7	0.062 (3)	0.039 (3)	0.027 (3)	0.005 (2)	−0.008 (2)	−0.005 (2)
O8	0.067 (3)	0.034 (3)	0.045 (3)	0.004 (2)	−0.004 (2)	−0.016 (2)
O1W	0.056 (3)	0.042 (3)	0.032 (3)	0.001 (2)	−0.005 (2)	0.013 (2)
O2W	0.056 (3)	0.044 (3)	0.060 (3)	−0.004 (2)	−0.001 (2)	−0.004 (2)
O3W	0.114 (4)	0.056 (3)	0.032 (3)	0.016 (3)	0.001 (3)	−0.010 (2)
O4W	0.105 (5)	0.118 (5)	0.039 (3)	−0.030 (4)	−0.016 (3)	0.002 (3)
Pb1	0.05346 (16)	0.02900 (14)	0.02090 (14)	0.00264 (12)	−0.00092 (9)	−0.00012 (11)

Geometric parameters (Å, º)

C1—N1	1.332 (7)	C15—H15	0.9300
C1—C2	1.360 (8)	C16—N5	1.336 (7)
C1—H1	0.9300	C16—N6	1.348 (7)
C2—C3	1.379 (8)	C17—N5	1.390 (7)
C2—H2	0.9300	C17—C18	1.393 (8)
C3—C4	1.385 (7)	C17—C20	1.479 (8)
C3—H3	0.9300	C18—N6	1.362 (7)
C4—C5	1.384 (7)	C18—C19	1.483 (8)
C4—C6	1.455 (7)	C19—O6	1.214 (8)
C5—N1	1.343 (7)	C19—O5	1.298 (8)
C5—H5	0.9300	C20—O7	1.238 (7)
C6—N3	1.325 (6)	C20—O8	1.276 (7)
C6—N2	1.358 (7)	N1—Pb1^i	2.622 (5)
C7—N2	1.364 (6)	N2—H2N	0.8292
C7—C8	1.375 (8)	N3—Pb1	2.796 (4)
C7—C9	1.484 (8)	N5—Pb1	2.820 (5)
C8—N3	1.365 (6)	N6—H6N	0.8601
C8—C10	1.486 (7)	O2—H2O	0.8201
C9—O1	1.237 (7)	O3—Pb1	2.526 (4)
C9—O2	1.296 (7)	O5—H5O	0.8336
C10—O3	1.238 (7)	O7—Pb1	2.686 (4)
C10—O4	1.288 (6)	O1W—Pb1	2.495 (4)
C11—N4	1.347 (8)	O1W—H1W	0.9343
C11—C12	1.372 (8)	O1W—H2W	0.8276
C11—H11	0.9300	O2W—Pb1	2.692 (4)
C12—C13	1.377 (9)	O2W—H3W	0.7972
C12—H12	0.9300	O2W—H4W	0.8164
C13—C14	1.397 (8)	O3W—H5W	0.7965
C13—H13	0.9300	O3W—H6W	0.7801
C14—C15	1.381 (7)	O4W—H7W	0.8500
C14—C16	1.461 (8)	O4W—H8W	0.8241
C15—N4	1.329 (7)	Pb1—N1^ii	2.622 (5)
N1—C1—C2	124.0 (6)	O6—C19—C18	119.6 (6)
N1—C1—H1	118.0	O5—C19—C18	116.4 (6)
C2—C1—H1	118.0	O7—C20—O8	123.5 (6)
C1—C2—C3	117.9 (5)	O7—C20—C17	119.2 (6)
C1—C2—H2	121.0	O8—C20—C17	117.3 (6)
C3—C2—H2	121.0	C1—N1—C5	117.4 (5)
C2—C3—C4	120.3 (5)	C1—N1—Pb1^i	116.5 (4)
C2—C3—H3	119.8	C5—N1—Pb1^i	124.7 (4)
C4—C3—H3	119.8	C6—N2—C7	107.8 (5)
C5—C4—C3	117.0 (5)	C6—N2—H2N	124.0
C5—C4—C6	122.3 (5)	C7—N2—H2N	127.8
C3—C4—C6	120.6 (5)	C6—N3—C8	106.1 (5)
N1—C5—C4	123.3 (5)	C6—N3—Pb1	142.3 (4)
N1—C5—H5	118.3	C8—N3—Pb1	111.5 (3)
C4—C5—H5	118.3	C15—N4—C11	117.6 (5)
N3—C6—N2	110.6 (5)	C16—N5—C17	104.9 (5)
N3—C6—C4	124.7 (5)	C16—N5—Pb1	140.4 (4)
N2—C6—C4	124.7 (5)	C17—N5—Pb1	112.5 (3)
N2—C7—C8	105.6 (5)	C16—N6—C18	108.3 (5)
N2—C7—C9	120.9 (6)	C16—N6—H6N	125.9
C8—C7—C9	133.5 (6)	C18—N6—H6N	125.8
N3—C8—C7	109.9 (5)	C9—O2—H2O	109.7
N3—C8—C10	120.2 (5)	C10—O3—Pb1	126.1 (4)
C7—C8—C10	129.9 (5)	C19—O5—H5O	113.1
O1—C9—O2	122.4 (6)	C20—O7—Pb1	123.5 (4)
O1—C9—C7	119.5 (6)	Pb1—O1W—H1W	105.4
O2—C9—C7	118.1 (6)	Pb1—O1W—H2W	110.8
O3—C10—O4	122.2 (5)	H1W—O1W—H2W	111.9
O3—C10—C8	119.3 (5)	Pb1—O2W—H3W	110.6
O4—C10—C8	118.4 (5)	Pb1—O2W—H4W	109.9
N4—C11—C12	122.8 (6)	H3W—O2W—H4W	107.3
N4—C11—H11	118.6	H5W—O3W—H6W	109.0
C12—C11—H11	118.6	H7W—O4W—H8W	109.8
C11—C12—C13	119.2 (6)	O1W—Pb1—O3	67.27 (13)
C11—C12—H12	120.4	O1W—Pb1—N1^ii	88.81 (14)
C13—C12—H12	120.4	O3—Pb1—N1^ii	70.53 (14)
C12—C13—C14	118.7 (6)	O1W—Pb1—O7	76.59 (13)
C12—C13—H13	120.7	O3—Pb1—O7	133.39 (13)
C14—C13—H13	120.7	N1^ii—Pb1—O7	80.58 (13)
C15—C14—C13	118.1 (5)	O1W—Pb1—O2W	151.47 (12)
C15—C14—C16	122.7 (5)	O3—Pb1—O2W	84.21 (13)
C13—C14—C16	119.3 (5)	N1^ii—Pb1—O2W	80.57 (14)
N4—C15—C14	123.6 (6)	O7—Pb1—O2W	126.77 (13)
N4—C15—H15	118.2	O1W—Pb1—N3	95.92 (13)
C14—C15—H15	118.2	O3—Pb1—N3	62.76 (13)
N5—C16—N6	111.7 (5)	N1^ii—Pb1—N3	126.42 (13)
N5—C16—C14	122.9 (5)	O7—Pb1—N3	152.28 (12)
N6—C16—C14	125.3 (5)	O2W—Pb1—N3	70.37 (13)
N5—C17—C18	109.4 (5)	O1W—Pb1—N5	70.02 (13)
N5—C17—C20	120.8 (5)	O3—Pb1—N5	126.13 (14)
C18—C17—C20	129.8 (6)	N1^ii—Pb1—N5	139.11 (14)
N6—C18—C17	105.6 (5)	O7—Pb1—N5	61.04 (13)
N6—C18—C19	120.4 (5)	O2W—Pb1—N5	132.95 (13)
C17—C18—C19	133.9 (6)	N3—Pb1—N5	91.27 (13)
O6—C19—O5	124.0 (6)
N1—C1—C2—C3	−1.0 (9)	C10—C8—N3—C6	−178.2 (5)
C1—C2—C3—C4	2.7 (8)	C7—C8—N3—Pb1	−178.3 (3)
C2—C3—C4—C5	−3.1 (8)	C10—C8—N3—Pb1	2.7 (6)
C2—C3—C4—C6	176.0 (5)	C14—C15—N4—C11	1.5 (8)
C3—C4—C5—N1	2.0 (8)	C12—C11—N4—C15	−0.7 (9)
C6—C4—C5—N1	−177.1 (5)	N6—C16—N5—C17	−1.1 (6)
C5—C4—C6—N3	165.5 (5)	C14—C16—N5—C17	175.3 (5)
C3—C4—C6—N3	−13.6 (8)	N6—C16—N5—Pb1	159.5 (4)
C5—C4—C6—N2	−11.9 (8)	C14—C16—N5—Pb1	−24.1 (9)
C3—C4—C6—N2	169.0 (5)	C18—C17—N5—C16	1.6 (6)
N2—C7—C8—N3	−1.2 (6)	C20—C17—N5—C16	−178.8 (5)
C9—C7—C8—N3	178.3 (6)	C18—C17—N5—Pb1	−165.1 (3)
N2—C7—C8—C10	177.7 (5)	C20—C17—N5—Pb1	14.5 (6)
C9—C7—C8—C10	−2.8 (11)	N5—C16—N6—C18	0.2 (6)
N2—C7—C9—O1	0.0 (9)	C14—C16—N6—C18	−176.1 (5)
C8—C7—C9—O1	−179.4 (6)	C17—C18—N6—C16	0.8 (6)
N2—C7—C9—O2	−179.1 (5)	C19—C18—N6—C16	177.4 (5)
C8—C7—C9—O2	1.5 (10)	O4—C10—O3—Pb1	179.0 (4)
N3—C8—C10—O3	0.1 (8)	C8—C10—O3—Pb1	−3.5 (7)
C7—C8—C10—O3	−178.7 (6)	O8—C20—O7—Pb1	167.8 (4)
N3—C8—C10—O4	177.6 (5)	C17—C20—O7—Pb1	−13.0 (7)
C7—C8—C10—O4	−1.2 (9)	C10—O3—Pb1—O1W	−106.5 (5)
N4—C11—C12—C13	−0.6 (9)	C10—O3—Pb1—N1^ii	156.4 (5)
C11—C12—C13—C14	1.1 (9)	C10—O3—Pb1—O7	−148.6 (4)
C12—C13—C14—C15	−0.4 (8)	C10—O3—Pb1—O2W	74.4 (5)
C12—C13—C14—C16	179.5 (5)	C10—O3—Pb1—N3	3.5 (4)
C13—C14—C15—N4	−1.0 (8)	C10—O3—Pb1—N5	−66.3 (5)
C16—C14—C15—N4	179.1 (5)	C20—O7—Pb1—O1W	88.7 (5)
C15—C14—C16—N5	147.3 (5)	C20—O7—Pb1—O3	128.2 (4)
C13—C14—C16—N5	−32.6 (8)	C20—O7—Pb1—N1^ii	179.7 (5)
C15—C14—C16—N6	−36.7 (8)	C20—O7—Pb1—O2W	−109.6 (5)
C13—C14—C16—N6	143.4 (6)	C20—O7—Pb1—N3	11.8 (6)
N5—C17—C18—N6	−1.5 (6)	C20—O7—Pb1—N5	14.3 (4)
C20—C17—C18—N6	178.9 (5)	C6—N3—Pb1—O1W	−120.9 (6)
N5—C17—C18—C19	−177.5 (6)	C8—N3—Pb1—O1W	57.8 (3)
C20—C17—C18—C19	3.0 (11)	C6—N3—Pb1—O3	178.5 (6)
N6—C18—C19—O6	−0.3 (9)	C8—N3—Pb1—O3	−2.8 (3)
C17—C18—C19—O6	175.2 (6)	C6—N3—Pb1—N1^ii	146.2 (5)
N6—C18—C19—O5	179.8 (5)	C8—N3—Pb1—N1^ii	−35.1 (4)
C17—C18—C19—O5	−4.7 (10)	C6—N3—Pb1—O7	−48.6 (7)
N5—C17—C20—O7	−2.5 (8)	C8—N3—Pb1—O7	130.1 (4)
C18—C17—C20—O7	177.0 (6)	C6—N3—Pb1—O2W	84.9 (6)
N5—C17—C20—O8	176.8 (5)	C8—N3—Pb1—O2W	−96.4 (3)
C18—C17—C20—O8	−3.7 (9)	C6—N3—Pb1—N5	−50.8 (6)
C2—C1—N1—C5	−0.1 (9)	C8—N3—Pb1—N5	127.9 (3)
C2—C1—N1—Pb1^i	−167.2 (5)	C16—N5—Pb1—O1W	101.7 (6)
C4—C5—N1—C1	−0.4 (8)	C17—N5—Pb1—O1W	−98.7 (4)
C4—C5—N1—Pb1^i	165.5 (4)	C16—N5—Pb1—O3	62.4 (6)
N3—C6—N2—C7	−0.6 (6)	C17—N5—Pb1—O3	−137.9 (3)
C4—C6—N2—C7	177.2 (5)	C16—N5—Pb1—N1^ii	164.7 (5)
C8—C7—N2—C6	1.1 (6)	C17—N5—Pb1—N1^ii	−35.6 (4)
C9—C7—N2—C6	−178.5 (5)	C16—N5—Pb1—O7	−172.9 (6)
N2—C6—N3—C8	−0.2 (6)	C17—N5—Pb1—O7	−13.3 (3)
C4—C6—N3—C8	−177.9 (5)	C16—N5—Pb1—O2W	−58.2 (6)
N2—C6—N3—Pb1	178.6 (4)	C17—N5—Pb1—O2W	101.5 (4)
C4—C6—N3—Pb1	0.8 (9)	C16—N5—Pb1—N3	5.8 (6)
C7—C8—N3—C6	0.9 (6)	C17—N5—Pb1—N3	165.5 (3)

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W···N4^ii	0.93	1.74	2.664 (6)	170
N2—H2N···O3W^iii	0.83	2.02	2.822 (6)	161
O2—H2O···O4	0.82	1.65	2.469 (6)	179
O1W—H2W···O6^iv	0.83	2.00	2.767 (6)	154
O2W—H3W···O1W^v	0.80	2.19	2.849 (6)	140
O2W—H4W···O1^vi	0.82	1.98	2.788 (6)	170
O5—H5O···O8	0.83	1.60	2.435 (6)	175
O3W—H5W···O7^vii	0.80	2.24	2.981 (6)	156
N6—H6N···O4W^i	0.86	2.00	2.850 (7)	170
O3W—H6W···O4^viii	0.78	2.47	3.129 (7)	143
O4W—H7W···O4	0.85	2.52	2.941 (6)	112
O4W—H8W···O3W	0.82	2.24	3.047 (7)	168
C2—H2···O8^ix	0.93	2.41	3.226 (7)	147
C12—H12···O2^iii	0.93	2.46	3.384 (7)	174

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