catena-Poly[[[bis­(methanol-κO)lead(II)]-μ-N′-[1-(pyridin-2-yl-κN)ethyl­idene]isonicotinohydrazidato-κ³N′,O:N¹] perchlorate]

The Pb^II atom in the polymeric title compound, {[Pb(C₁₃H₁₁N₄O)(CH₃OH)₂]ClO₄}_n, is coordinated by an N′-[1-(pyridin-2-yl-κN)ethyl­idene]isonicotinohydrazidate ligand via O,N,N′-donors and simultaneously bridged by a neighbouring ligand via the isonicotinoyl N atom; two additional sites are occupied by methanol O atoms. The resultant supra­molecular chain is a zigzag along the c axis. The Pb^II atom is seven-coordinated within an N₃O₃ donor set and a lone pair of electrons, which defines a Ψ-pentagonal–bipyramidal coordination geometry with the pyridine N and lone pair in axial positions. The supra­molecular chains are linked into the two-dimensional array via inter­molecular Pb...N [3.020 (4) Å] inter­actions. Layers stack along the a axis, being connected by O—H...O hydrogen bonds formed between the coordinated methanol mol­ecules and perchlorate anions.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.024
• wR factor = 0.066
• Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...        5.3 Ratio

Author Response: The atoms comprising the coordinated methanol molecules (and anion) exhibit greater thermal motion and the other atoms comprising the structure. No evidence for resolvable disorder was found, however.

Alert level C
PLAT222_ALERT_3_C Large Non-Solvent    H    Uiso(max)/Uiso(min) ..        5.4 Ratio
PLAT342_ALERT_3_C Low Bond Precision on  C-C Bonds ...............     0.0085 Ang
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         16

Alert level G
PLAT004_ALERT_5_G Info: Polymeric Structure Found with Dimension .          1
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT Unusually Large.       6.18
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pb     --  O3      ..        5.3 su
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          61 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   1 ALERT level B = A potentially serious problem, consider carefully
   3 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   0 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
   4 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

---

S1. Comment

Structural studies of coordination complexes containing the N'-[1-(2-pyridyl)ethylidene]isonicotinohydrazide ligand are rare (Maurya et al., 2002; Abboud et al., 2007; Zhang & Liu, 2009; Hao et al., 2010). In each of these, the ligand coordinates in a tridentate mode with the terminal 4-pyridyl-N atom being non-coordinating. In a recently reported Pb^II structure, all four donor atoms were involved in coordination leading to a zigzag chain (Shahverdizadeh et al., 2011). A similar mode of coordination was found in the title lead(II) complex, (I), with complete details described herein.

The crystallographic asymmetric unit of (I), Fig. 1, comprises a Pb^II atom, an N'-1-(2-pyridyl)ethylidene]isonicotinohydrazide anion, a perchlorate anion, and two methanol molecules. The N'-[1-(2-pyridyl)ethylidene]isonicotinohydrazide ligand coordinates a lead atom in a tridentate mode, via the N1, N2 and O1 atoms, and simultaneously bridges a symmetry related lead atom via the 4-pyridyl-N4 atom., Table 1. Both methanol molecules are connected to the Pb^II atom. The resulting N₃O₃ donor set, along with a stereochemically active lone pair of electrons, define a pentagonal bipyramidal geometry with the pyridyl-N4 atom lone pair of electrons occupying axial positions. The µ₂-bridging mode of the tetradentate N'-[1-(2-pyridyl)ethylidene]isonicotinohydrazide ligand leads to a zigzag chain (glide symmetry) along the c axis, Fig. 2.

In the crystal packing, centrosymmetrically related supramolecular chains are linked into a two-dimensional array by Pb···N interactions [Pb···N3ⁱ = 3.020 (4) Å for i: 1 - x, 1 - y, 1 - z]. The layers thus formed in the bc plane are connected into a three-dimensional architecture via O—H···O hydrogen bonds involving the coordinated methanol molecules and the perchlorate anions, Fig. 4 and Table 2.

Related literature

For the structures of metal complexes containing the N'-[1-(2-pyridyl)ethylidene]isonicotinohydrazide ligand, see: Maurya et al. (2002); Abboud et al. (2007); Zhang & Liu (2009); Hao et al. (2010); Shahverdizadeh et al. (2011). For specialized crystallization techniques, see: Harrowfield et al. (1996).

S2. Experimental

A solution of methyl 2-pyridyl ketone (15 mmol) in MeOH (25 ml) was added drop-wise to a solution of 4-pyridinecarboxylic acid hydrazide (15 mmol) in MeOH (15 ml). The mixture was refluxed for 6 h. The white precipitate was removed by filtration and recrystallized from MeOH solution. Then the compound (1 mmol) was placed in one arm of a branched tube (Harrowfield et al., 1996) and a mixture of lead(II) acetate (1 mmol) and sodium perchlorate (1 mmol) in the other. Methanol was then added to fill both arms, the tube sealed and the ligand-containing arm immersed in a bath at 333 K, while the other was left at ambient temperature. After 2 weeks, crystals had deposited in the arm held at ambient temperature. They were filtered off, washed with acetone and ether, and air dried. Yield: 66%; M.pt.: 516 K.

S3. Refinement

The O– and C-bound H-atoms were placed in calculated positions [O—H = 0.84 Å; C—H = 0.95–0.98 Å, U_iso(H) = 1.2–1.5U_eq(parent atom)] and were included in the refinement in the riding model approximation. The atoms comprising the coordinated methanol molecules (and anion) exhibit greater thermal motion than the other atoms in the structure. No evidence for resolvable disorder was found, however.

Computing details

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures

	Fig. 1. The asymmetric unit of (I) showing the atom-labelling scheme and displacement ellipsoids at the 50% probability level. The molecular structure has been expanded to indicate the µ2-bridging mode of the tetradentate ligand. Symmetry operations i: x, 0.5 - y, -1/2 + z; ii: x, 1/2 + y, 0.5 - z.
	Fig. 2. A view of the supramolecular zigzag chain along the c axis in (I).
	Fig. 3. A view of the two-dimensional array in the bc plane in (I). The weaker Pb···N interactions (see text) are shown as blue dashed lines.
	Fig. 4. A view in projection down the c axis of the crystal packing in (I). The weaker Pb···N interactions (see text) are shown as blue dashed lines, and the O—H···O hydrogen bonds are shown as orange dashed lines.

catena-Poly[[[bis(methanol-κO)lead(II)]-µ- N'-[1-(pyridin-2-yl-κN)ethylidene]isonicotinohydrazidato- κ³N',O:N¹] perchlorate]

Crystal data

[Pb(C13H11N4O)(CH4O)2]ClO4	F(000) = 1168
Mr = 609.98	Dx = 2.045 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4546 reflections
a = 11.2122 (14) Å	θ = 2.2–25.0°
b = 13.4644 (17) Å	µ = 8.70 mm^−1
c = 14.1451 (18) Å	T = 173 K
β = 111.906 (2)°	Prism, yellow
V = 1981.2 (4) Å^3	0.46 × 0.43 × 0.37 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3492 independent reflections
Radiation source: fine-focus sealed tube	2641 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.027
φ and ω scans	θmax = 25.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→8
Tmin = 0.108, Tmax = 0.141	k = −16→15
10367 measured reflections	l = −12→16

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.066	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0282P)^2 + 6.1832P] where P = (Fo^2 + 2Fc^2)/3
3492 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.97 e Å^−3
0 restraints	Δρmin = −0.98 e Å^−3

Special details

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Pb	0.379666 (16)	0.502370 (14)	0.303341 (13)	0.01308 (8)
Cl1	−0.07646 (14)	0.25586 (11)	0.34029 (12)	0.0297 (3)
O1	0.3551 (3)	0.3685 (3)	0.4082 (3)	0.0160 (8)
O2	0.1391 (4)	0.4209 (3)	0.2361 (3)	0.0304 (10)
H2O	0.1367	0.3678	0.2666	0.037*
O3	0.2933 (5)	0.5804 (4)	0.0983 (3)	0.0449 (12)
H3O	0.2399	0.6262	0.0916	0.054*
O4	0.0480 (5)	0.2805 (5)	0.3505 (4)	0.080 (2)
O5	−0.0732 (6)	0.2110 (5)	0.4315 (4)	0.081 (2)
O6	−0.1531 (6)	0.3419 (5)	0.3194 (5)	0.088 (2)
O7	−0.1306 (6)	0.1904 (5)	0.2568 (4)	0.076 (2)
N1	0.6011 (4)	0.5630 (3)	0.2931 (3)	0.0171 (10)
N2	0.5835 (4)	0.4394 (3)	0.4342 (3)	0.0138 (9)
N3	0.5741 (4)	0.3751 (3)	0.5074 (3)	0.0138 (9)
N4	0.4129 (4)	0.1305 (3)	0.6945 (3)	0.0168 (10)
C1	0.7110 (5)	0.5362 (4)	0.3701 (4)	0.0136 (11)
C2	0.8302 (5)	0.5696 (4)	0.3747 (5)	0.0255 (13)
H2	0.9062	0.5498	0.4293	0.031*
C3	0.8377 (6)	0.6317 (5)	0.2996 (5)	0.0313 (15)
H3	0.9188	0.6541	0.3011	0.038*
C4	0.7259 (6)	0.6607 (4)	0.2223 (5)	0.0285 (14)
H4	0.7282	0.7047	0.1705	0.034*
C5	0.6108 (5)	0.6249 (4)	0.2216 (4)	0.0205 (12)
H5	0.5340	0.6448	0.1679	0.025*
C6	0.6980 (5)	0.4684 (4)	0.4476 (4)	0.0147 (11)
C7	0.8175 (5)	0.4367 (4)	0.5349 (4)	0.0195 (12)
H7A	0.7934	0.3963	0.5826	0.029*
H7B	0.8646	0.4956	0.5701	0.029*
H7C	0.8722	0.3975	0.5087	0.029*
C8	0.4546 (5)	0.3432 (4)	0.4834 (4)	0.0125 (11)
C9	0.4411 (5)	0.2683 (4)	0.5577 (4)	0.0120 (10)
C10	0.3203 (5)	0.2332 (4)	0.5473 (4)	0.0163 (11)
H10	0.2457	0.2561	0.4932	0.020*
C11	0.3101 (5)	0.1652 (4)	0.6160 (4)	0.0182 (12)
H11	0.2271	0.1414	0.6080	0.022*
C12	0.5287 (5)	0.1646 (4)	0.7041 (4)	0.0174 (12)
H12	0.6019	0.1410	0.7590	0.021*
C13	0.5467 (5)	0.2326 (4)	0.6377 (4)	0.0148 (11)
H13	0.6307	0.2546	0.6468	0.018*
C15	0.0171 (6)	0.4465 (6)	0.1622 (6)	0.0463 (19)
H15A	−0.0462	0.3962	0.1617	0.069*
H15B	0.0228	0.4497	0.0948	0.069*
H15C	−0.0094	0.5114	0.1791	0.069*
C16	0.3117 (8)	0.5665 (8)	0.0072 (6)	0.065 (3)
H16A	0.3963	0.5365	0.0213	0.098*
H16B	0.3071	0.6307	−0.0265	0.098*
H16C	0.2447	0.5224	−0.0373	0.098*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb	0.01177 (12)	0.01436 (11)	0.01108 (11)	0.00120 (9)	0.00192 (8)	−0.00026 (9)
Cl1	0.0206 (7)	0.0349 (8)	0.0335 (8)	−0.0006 (7)	0.0101 (6)	−0.0074 (7)
O1	0.013 (2)	0.020 (2)	0.0106 (18)	−0.0043 (15)	−0.0003 (15)	0.0014 (15)
O2	0.018 (2)	0.037 (2)	0.028 (2)	−0.0036 (18)	0.0004 (18)	0.002 (2)
O3	0.046 (3)	0.057 (3)	0.035 (3)	0.024 (2)	0.018 (2)	0.015 (2)
O4	0.028 (3)	0.143 (6)	0.057 (4)	−0.022 (3)	0.003 (3)	0.039 (4)
O5	0.099 (5)	0.097 (5)	0.048 (4)	−0.042 (4)	0.031 (3)	0.000 (3)
O6	0.078 (5)	0.084 (5)	0.098 (5)	0.040 (4)	0.027 (4)	−0.015 (4)
O7	0.078 (4)	0.075 (4)	0.050 (4)	0.013 (3)	−0.006 (3)	−0.032 (3)
N1	0.013 (2)	0.021 (2)	0.017 (2)	−0.0003 (19)	0.0044 (19)	0.0029 (19)
N2	0.018 (2)	0.011 (2)	0.013 (2)	0.0007 (18)	0.0071 (18)	0.0020 (17)
N3	0.010 (2)	0.019 (2)	0.011 (2)	−0.0015 (18)	0.0024 (18)	0.0029 (18)
N4	0.017 (2)	0.017 (2)	0.015 (2)	0.0003 (19)	0.0042 (19)	0.0030 (18)
C1	0.018 (3)	0.009 (2)	0.017 (3)	0.000 (2)	0.010 (2)	−0.003 (2)
C2	0.014 (3)	0.027 (3)	0.033 (3)	0.004 (2)	0.006 (3)	0.010 (3)
C3	0.021 (3)	0.033 (4)	0.043 (4)	0.000 (3)	0.015 (3)	0.017 (3)
C4	0.036 (4)	0.023 (3)	0.030 (4)	0.000 (3)	0.016 (3)	0.010 (3)
C5	0.023 (3)	0.020 (3)	0.017 (3)	0.000 (2)	0.005 (2)	0.005 (2)
C6	0.013 (3)	0.013 (2)	0.017 (3)	0.002 (2)	0.004 (2)	−0.001 (2)
C7	0.012 (3)	0.026 (3)	0.019 (3)	0.003 (2)	0.003 (2)	0.006 (2)
C8	0.013 (3)	0.012 (3)	0.012 (3)	0.000 (2)	0.003 (2)	−0.003 (2)
C9	0.015 (3)	0.012 (2)	0.010 (2)	−0.002 (2)	0.005 (2)	−0.003 (2)
C10	0.013 (3)	0.020 (3)	0.011 (3)	−0.002 (2)	0.000 (2)	0.000 (2)
C11	0.013 (3)	0.020 (3)	0.020 (3)	−0.005 (2)	0.004 (2)	0.000 (2)
C12	0.016 (3)	0.021 (3)	0.014 (3)	0.000 (2)	0.003 (2)	0.000 (2)
C13	0.013 (3)	0.014 (3)	0.017 (3)	0.000 (2)	0.005 (2)	0.001 (2)
C15	0.024 (4)	0.056 (5)	0.044 (4)	0.006 (3)	−0.004 (3)	−0.005 (4)
C16	0.043 (5)	0.116 (8)	0.031 (4)	0.004 (5)	0.007 (4)	0.005 (5)

Geometric parameters (Å, º)

Pb—O1	2.415 (3)	C2—H2	0.9500
Pb—O2	2.733 (4)	C3—C4	1.378 (8)
Pb—O3	2.891 (4)	C3—H3	0.9500
Pb—N1	2.669 (4)	C4—C5	1.374 (8)
Pb—N2	2.493 (4)	C4—H4	0.9500
Pb—N4^i	2.477 (4)	C5—H5	0.9500
Cl1—O4	1.389 (5)	C6—C7	1.505 (7)
Cl1—O6	1.406 (6)	C7—H7A	0.9800
Cl1—O5	1.412 (6)	C7—H7B	0.9800
Cl1—O7	1.417 (5)	C7—H7C	0.9800
O1—C8	1.268 (6)	C8—C9	1.505 (7)
O2—C15	1.420 (7)	C9—C13	1.384 (7)
O2—H2O	0.8400	C9—C10	1.389 (7)
O3—C16	1.392 (9)	C10—C11	1.371 (7)
O3—H3O	0.8400	C10—H10	0.9500
N1—C5	1.345 (7)	C11—H11	0.9500
N1—C1	1.354 (7)	C12—C13	1.379 (7)
N2—C6	1.286 (7)	C12—H12	0.9500
N2—N3	1.384 (6)	C13—H13	0.9500
N3—C8	1.325 (7)	C15—H15A	0.9800
N4—C12	1.335 (7)	C15—H15B	0.9800
N4—C11	1.351 (7)	C15—H15C	0.9800
N4—Pb^ii	2.477 (4)	C16—H16A	0.9800
C1—C2	1.389 (7)	C16—H16B	0.9800
C1—C6	1.475 (8)	C16—H16C	0.9800
C2—C3	1.379 (8)
O1—Pb—N4^i	85.45 (13)	C2—C3—H3	120.5
O1—Pb—N2	64.74 (12)	C5—C4—C3	118.7 (5)
N4^i—Pb—N2	84.66 (14)	C5—C4—H4	120.7
O1—Pb—N1	125.71 (12)	C3—C4—H4	120.7
N4^i—Pb—N1	80.14 (14)	N1—C5—C4	123.4 (5)
N2—Pb—N1	61.99 (13)	N1—C5—H5	118.3
O1—Pb—O2	65.79 (12)	C4—C5—H5	118.3
N4^i—Pb—O2	81.46 (14)	N2—C6—C1	116.6 (5)
N2—Pb—O2	129.38 (13)	N2—C6—C7	124.6 (5)
N1—Pb—O2	157.14 (13)	C1—C6—C7	118.8 (5)
O1—Pb—O3	144.62 (13)	C6—C7—H7A	109.5
N4^i—Pb—O3	73.20 (14)	C6—C7—H7B	109.5
N2—Pb—O3	137.72 (13)	H7A—C7—H7B	109.5
N1—Pb—O3	78.73 (13)	C6—C7—H7C	109.5
O2—Pb—O3	83.06 (14)	H7A—C7—H7C	109.5
O4—Cl1—O6	109.6 (5)	H7B—C7—H7C	109.5
O4—Cl1—O5	108.9 (4)	O1—C8—N3	128.2 (5)
O6—Cl1—O5	110.5 (4)	O1—C8—C9	118.6 (5)
O4—Cl1—O7	109.7 (4)	N3—C8—C9	113.2 (4)
O6—Cl1—O7	107.4 (4)	C13—C9—C10	118.1 (5)
O5—Cl1—O7	110.6 (4)	C13—C9—C8	121.7 (5)
C8—O1—Pb	116.7 (3)	C10—C9—C8	120.2 (5)
C15—O2—Pb	135.5 (4)	C11—C10—C9	119.2 (5)
C15—O2—H2O	112.3	C11—C10—H10	120.4
Pb—O2—H2O	112.3	C9—C10—H10	120.4
C16—O3—Pb	140.3 (5)	N4—C11—C10	122.8 (5)
C16—O3—H3O	109.8	N4—C11—H11	118.6
Pb—O3—H3O	109.8	C10—C11—H11	118.6
C5—N1—C1	117.8 (5)	N4—C12—C13	122.9 (5)
C5—N1—Pb	124.6 (3)	N4—C12—H12	118.6
C1—N1—Pb	117.4 (3)	C13—C12—H12	118.6
C6—N2—N3	115.5 (4)	C12—C13—C9	119.3 (5)
C6—N2—Pb	126.5 (3)	C12—C13—H13	120.3
N3—N2—Pb	117.6 (3)	C9—C13—H13	120.3
C8—N3—N2	111.3 (4)	O2—C15—H15A	109.5
C12—N4—C11	117.6 (4)	O2—C15—H15B	109.5
C12—N4—Pb^ii	123.4 (3)	H15A—C15—H15B	109.5
C11—N4—Pb^ii	118.7 (3)	O2—C15—H15C	109.5
N1—C1—C2	121.5 (5)	H15A—C15—H15C	109.5
N1—C1—C6	116.8 (5)	H15B—C15—H15C	109.5
C2—C1—C6	121.7 (5)	O3—C16—H16A	109.5
C3—C2—C1	119.6 (5)	O3—C16—H16B	109.5
C3—C2—H2	120.2	H16A—C16—H16B	109.5
C1—C2—H2	120.2	O3—C16—H16C	109.5
C4—C3—C2	119.0 (6)	H16A—C16—H16C	109.5
C4—C3—H3	120.5	H16B—C16—H16C	109.5
N4^i—Pb—O1—C8	94.7 (4)	C5—N1—C1—C2	−1.2 (8)
N2—Pb—O1—C8	8.5 (3)	Pb—N1—C1—C2	−175.8 (4)
N1—Pb—O1—C8	20.3 (4)	C5—N1—C1—C6	−180.0 (5)
O2—Pb—O1—C8	177.4 (4)	Pb—N1—C1—C6	5.4 (6)
O3—Pb—O1—C8	147.0 (3)	N1—C1—C2—C3	0.2 (9)
O1—Pb—O2—C15	168.6 (6)	C6—C1—C2—C3	178.9 (5)
N4^i—Pb—O2—C15	−102.5 (6)	C1—C2—C3—C4	1.2 (9)
N2—Pb—O2—C15	−178.4 (5)	C2—C3—C4—C5	−1.4 (10)
N1—Pb—O2—C15	−65.8 (7)	C1—N1—C5—C4	0.9 (8)
O3—Pb—O2—C15	−28.6 (6)	Pb—N1—C5—C4	175.1 (4)
O1—Pb—O3—C16	−79.2 (8)	C3—C4—C5—N1	0.4 (9)
N4^i—Pb—O3—C16	−23.8 (8)	N3—N2—C6—C1	179.5 (4)
N2—Pb—O3—C16	37.7 (9)	Pb—N2—C6—C1	−8.2 (6)
N1—Pb—O3—C16	59.1 (8)	N3—N2—C6—C7	0.4 (7)
O2—Pb—O3—C16	−107.0 (8)	Pb—N2—C6—C7	172.8 (4)
O1—Pb—N1—C5	167.4 (4)	N1—C1—C6—N2	1.1 (7)
N4^i—Pb—N1—C5	90.3 (4)	C2—C1—C6—N2	−177.7 (5)
N2—Pb—N1—C5	179.5 (5)	N1—C1—C6—C7	−179.8 (5)
O2—Pb—N1—C5	53.5 (6)	C2—C1—C6—C7	1.4 (8)
O3—Pb—N1—C5	15.6 (4)	Pb—O1—C8—N3	−6.4 (7)
O1—Pb—N1—C1	−18.5 (4)	Pb—O1—C8—C9	173.2 (3)
N4^i—Pb—N1—C1	−95.5 (4)	N2—N3—C8—O1	−3.9 (7)
N2—Pb—N1—C1	−6.3 (3)	N2—N3—C8—C9	176.6 (4)
O2—Pb—N1—C1	−132.3 (4)	O1—C8—C9—C13	175.8 (5)
O3—Pb—N1—C1	−170.2 (4)	N3—C8—C9—C13	−4.6 (7)
O1—Pb—N2—C6	177.0 (5)	O1—C8—C9—C10	−4.4 (7)
N4^i—Pb—N2—C6	89.5 (4)	N3—C8—C9—C10	175.2 (5)
N1—Pb—N2—C6	7.8 (4)	C13—C9—C10—C11	0.0 (7)
O2—Pb—N2—C6	163.8 (4)	C8—C9—C10—C11	−179.8 (5)
O3—Pb—N2—C6	31.8 (5)	C12—N4—C11—C10	−0.3 (8)
O1—Pb—N2—N3	−10.8 (3)	Pb^ii—N4—C11—C10	−175.1 (4)
N4^i—Pb—N2—N3	−98.3 (3)	C9—C10—C11—N4	0.4 (8)
N1—Pb—N2—N3	−180.0 (4)	C11—N4—C12—C13	−0.1 (8)
O2—Pb—N2—N3	−24.0 (4)	Pb^ii—N4—C12—C13	174.4 (4)
O3—Pb—N2—N3	−156.0 (3)	N4—C12—C13—C9	0.4 (8)
C6—N2—N3—C8	−175.1 (4)	C10—C9—C13—C12	−0.4 (7)
Pb—N2—N3—C8	11.8 (5)	C8—C9—C13—C12	179.4 (5)

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
O2—H2o···O4	0.84	2.16	2.909 (7)	149
O3—H3o···O5^iii	0.84	2.11	2.930 (7)	166

Symmetry code: (iii) −x, y+1/2, −z+1/2.