Bis(2,9-dimethyl-1,10-phenanthroline-κ2N,N′)bis­(nitrato-κ2O,O′)lead(II)

Shen, F.M.; Lush, S.F.

doi:10.1107/S1600536810022312

Bis(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)bis(nitrato-κ²O,O′)lead(II)

In the title complex, [Pb(NO₃)₂(C₁₄H₁₂N₂)₂], the lead ion is chelated by two 2,9-dimethyl-1,10-phenanthroline (dmphen) ligands and two nitrate anions in a slightly distorted square-antiprismatic geometry. Intra- and intermolecular π–π stacking is present in the crystal structure, and the centroid–centroid distances between the benzene and pyridine rings of adjacent dmphen ligands are 3.492 (3) and 3.592 (3) Å, respectively. Intermolecular C—H

O hydrogen bonds and C—H

π interactions help to stabilize the crystal structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810022312/xu2779sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810022312/xu2779Isup2.hkl Contains datablock I

CCDC reference: 786450

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.007 Å
R factor = 0.021
wR factor = 0.040
Data-to-parameter ratio = 13.6

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT724_ALERT_2_A Contact Calc    16.75000, Rep     2.66000 Dev...      14.09 Ang.
              O1   -H16     1.555   4.485
PLAT724_ALERT_2_A Contact Calc    16.81000, Rep     2.91000 Dev...      13.90 Ang.
              O1   -H15     1.555   4.485
PLAT724_ALERT_2_A Contact Calc    18.35000, Rep     2.74000 Dev...      15.61 Ang.
              O3   -H15     1.555   4.485
PLAT724_ALERT_2_A Contact Calc    14.88000, Rep     2.53000 Dev...      12.35 Ang.
              O3   -H5      1.555   4.475
PLAT724_ALERT_2_A Contact Calc    15.34000, Rep     2.69000 Dev...      12.65 Ang.
              O3   -H4      1.555   4.475
PLAT724_ALERT_2_A Contact Calc    16.05000, Rep     2.77000 Dev...      13.28 Ang.
              O5   -H6      1.555   2.784
PLAT724_ALERT_2_A Contact Calc    17.80000, Rep     2.42000 Dev...      15.38 Ang.
              O6   -H17     1.555   2.794
PLAT724_ALERT_2_A Contact Calc    14.24000, Rep     2.54000 Dev...      11.70 Ang.
              O6   -H6      1.555   2.784
PLAT724_ALERT_2_A Contact Calc    17.93000, Rep     2.59000 Dev...      15.34 Ang.
              H3   -H7      1.555   2.784
PLAT724_ALERT_2_A Contact Calc    15.34000, Rep     2.69000 Dev...      12.65 Ang.
              H4   -O3      1.555   4.575
PLAT724_ALERT_2_A Contact Calc    14.88000, Rep     2.53000 Dev...      12.35 Ang.
              H5   -O3      1.555   4.575
PLAT724_ALERT_2_A Contact Calc    16.05000, Rep     2.77000 Dev...      13.28 Ang.
              H6   -O5      1.555   2.785
PLAT724_ALERT_2_A Contact Calc    14.24000, Rep     2.54000 Dev...      11.70 Ang.
              H6   -O6      1.555   2.785
PLAT724_ALERT_2_A Contact Calc    17.93000, Rep     2.59000 Dev...      15.34 Ang.
              H7   -H3      1.555   2.785
PLAT724_ALERT_2_A Contact Calc    16.81000, Rep     2.91000 Dev...      13.90 Ang.
              H15  -O1      1.555   4.585
PLAT724_ALERT_2_A Contact Calc    18.35000, Rep     2.74000 Dev...      15.61 Ang.
              H15  -O3      1.555   4.585
PLAT724_ALERT_2_A Contact Calc    16.75000, Rep     2.66000 Dev...      14.09 Ang.
              H16  -O1      1.555   4.585
PLAT724_ALERT_2_A Contact Calc    17.80000, Rep     2.42000 Dev...      15.38 Ang.
              H17  -O6      1.555   2.795
PLAT726_ALERT_2_A H...A   Calc    14.88000, Rep     2.53000 Dev...      12.35 Ang.
              H5   -O3      1.555   4.575
PLAT726_ALERT_2_A H...A   Calc    14.24000, Rep     2.54000 Dev...      11.70 Ang.
              H6   -O6      1.555   2.785
PLAT726_ALERT_2_A H...A   Calc    17.80000, Rep     2.42000 Dev...      15.38 Ang.
              H17  -O6      1.555   2.795
PLAT704_ALERT_1_A Contact Calc   16.569(5), Rep    3.401(7), Dev..    2633.60 Sigma
              O1   -C25     1.555   4.485
PLAT704_ALERT_1_A Contact Calc   14.835(5), Rep    3.266(5), Dev..    2313.80 Sigma
              O3   -C11     1.555   4.475
PLAT704_ALERT_1_A Contact Calc   14.578(5), Rep    3.192(5), Dev..    2277.20 Sigma
              O3   -C10     1.555   4.475
PLAT704_ALERT_1_A Contact Calc   13.990(5), Rep    3.376(5), Dev..    2122.80 Sigma
              O6   -C8      1.555   2.784
PLAT704_ALERT_1_A Contact Calc   17.974(5), Rep    3.158(5), Dev..    2963.20 Sigma
              O6   -C24     1.555   2.794
PLAT704_ALERT_1_A Contact Calc   13.990(5), Rep    3.376(5), Dev..    2122.80 Sigma
              C8   -O6      1.555   2.785
PLAT704_ALERT_1_A Contact Calc   14.578(5), Rep    3.192(5), Dev..    2277.20 Sigma
              C10  -O3      1.555   4.575
PLAT704_ALERT_1_A Contact Calc   14.835(5), Rep    3.266(5), Dev..    2313.80 Sigma
              C11  -O3      1.555   4.575
PLAT704_ALERT_1_A Contact Calc   17.974(5), Rep    3.158(5), Dev..    2963.20 Sigma
              C24  -O6      1.555   2.795
PLAT704_ALERT_1_A Contact Calc   16.569(5), Rep    3.401(7), Dev..    2633.60 Sigma
              C25  -O1      1.555   4.585
PLAT707_ALERT_1_A D...A   Calc   14.578(5), Rep    3.192(5), Dev..    2277.20 Sigma
              C10  -O3      1.555   4.575
PLAT707_ALERT_1_A D...A   Calc   13.990(5), Rep    3.376(5), Dev..    2122.80 Sigma
              C8   -O6      1.555   2.785
PLAT707_ALERT_1_A D...A   Calc   17.974(5), Rep    3.158(5), Dev..    2963.20 Sigma
              C24  -O6      1.555   2.795
PLAT728_ALERT_1_A D-H..A  Calc       70.00, Rep      127.00 Dev...      57.00 Deg.
              C10  -H5   -O3      1.555   1.555   4.575
PLAT728_ALERT_1_A D-H..A  Calc       73.00, Rep      147.00 Dev...      74.00 Deg.
              C8   -H6   -O6      1.555   1.555   2.785
PLAT728_ALERT_1_A D-H..A  Calc       99.00, Rep      135.00 Dev...      36.00 Deg.
              C24  -H17  -O6      1.555   1.555   2.795

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.33
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N1
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          1
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600          2
PLAT915_ALERT_3_C Low Friedel Pair Coverage ......................      52.94 Perc.
PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L=  0.600        320

Alert level G
REFLT03_ALERT_4_G  WARNING: Large fraction of Friedel related reflns may
                     be needed to determine absolute structure
           From the CIF: _diffrn_reflns_theta_max           29.11
           From the CIF: _reflns_number_total               5091
           Count of symmetry unique reflns         3622
           Completeness (_total/calc)            140.56%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1469
           Fraction of Friedel pairs measured     0.406
           Are heavy atom types Z>Si present        yes
PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X)  Pb1    --  O1      ..       5.39 su
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         13
PLAT033_ALERT_4_G Flack x Parameter Value Deviates from Zero .....       0.01

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

  16 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  26 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
   3 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

2,9-Dimethyl-1,10-phenanthroline ligand and its substituted derivates play an important role in the development of coordination chemistry (Kaes et al.,2000). There are several reports on coordination of 2,9-dimethyl-1,10-phenanthroline to metals, such as [Co(NO₃)₂(C₁₄H₁₂N₂)(H₂O)] (Ding et al., 2006), [Pb(C₁₄H₁₂N₂)(C₇H₅O₃)₂].C₁₄H₁₂N₂.H₂O (Zhao & Xuan, 2007), [Mn(C₇H₅O₃)₂(C₁₄H₁₂N₂)(H₂O)](C₁₄H₁₂N₂.C₂H₆O.H₂O) (Xuan & Zhao, 2007) and [Hg(C₂H₃O₂)₂(C₁₄H₁₂N₂)] (Harvey et al., 2004).

In the structure of the title compound the lead ion is eight-coordinated by four N atoms of two dmphen ligands, four O atoms of two nitrate anions. The resulting coordination is a square antiprismatic geometry, as shown in Fig 1. The Pb—O and Pb—N bond lengths are listed in Table 1. In the crystal structure, there are several C—H···O hydrogen bonds (full details and symmetry codes are given in Table 2 and Fig 2. On the other hand, π-π stacking interactions are between neighboring heteraromatic ring with centroid-centroid distance in the range 3.492 (3)~3.917 (2) Å, the shortest is between Cg3 (N5/C15,C23—C26)··· Cg5 (C1,C2,C6—C9) is 3.492 (3) Å and dihedral angle between two rings is 7.8 (2)°. In additional, C—H···π interactions [C14 —H11··· Cg4 (N6/C16—C20) and C27—H14··· Cg1 (N2/C1,C9—C12); full details and symmetry codes are given in Table 2)] are also present.

Related literature top

The 2,9-dimethyl-1,10-phenanthroline ligand and its substituted derivatives play an important role in the development of coordination chemistry (see Kaes et al., 2000). For related structures of 2,9-dimethyl-1,10-phenanthroline complexes, see: Ding et al. (2006); Harvey et al. (2004); Kaes et al. (2000); Xuan & Zhao (2007); Zhao & Xuan (2007).

Experimental top

The mixture of Pb(NO₃)₂ (165.5 mg, 0.50 mmole) with dmphen (108.1 mg, 0.50 mmole) in 10 ml H₂O was seal in a 25 ml stainless-steel reactor with a Teflon linear, heat to 180 °C for 72 hr, and then slowly cooled to room temperature. The pale yellow crystals of the title compound were obtained in 65.85% yield (based on Pb).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. The molecular packing for the title compound, viewed along the b axis. Hydrogen-bonding associations are shown as dotted lines.

Bis(2,9-dimethyl-1,10-phenanthroline-κ²N,N')bis(nitrato- κ²O,O')lead(II) top

Crystal data top

[Pb(NO₃)₂(C₁₄H₁₂N₂)₂]	F(000) = 1456
M_r = 747.73	D_x = 1.902 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 8515 reflections
a = 19.9164 (4) Å	θ = 2.4–29.0°
b = 8.0173 (1) Å	µ = 6.52 mm⁻¹
c = 16.3575 (3) Å	T = 100 K
V = 2611.90 (8) Å³	Block, pale yellow
Z = 4	0.32 × 0.18 × 0.12 mm

Data collection top

Oxford Diffraction Gemini-S CCD diffractometer	5091 independent reflections
Radiation source: fine-focus sealed tube	4126 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω–scan	θ_max = 29.1°, θ_min = 2.4°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −26→26
T_min = 0.286, T_max = 0.458	k = −10→10
13236 measured reflections	l = −15→22

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.040	w = 1/[σ²(F_o²) + (0.020P)²] where P = (F_o² + 2F_c²)/3
S = 0.91	(Δ/σ)_max = 0.020
5091 reflections	Δρ_max = 1.66 e Å⁻³
375 parameters	Δρ_min = −0.71 e Å⁻³
13 restraints	Absolute structure: Flack (1983), 1469 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.011 (5)

Crystal data top

[Pb(NO₃)₂(C₁₄H₁₂N₂)₂]	V = 2611.90 (8) Å³
M_r = 747.73	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 19.9164 (4) Å	µ = 6.52 mm⁻¹
b = 8.0173 (1) Å	T = 100 K
c = 16.3575 (3) Å	0.32 × 0.18 × 0.12 mm

Data collection top

Oxford Diffraction Gemini-S CCD diffractometer	5091 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	4126 reflections with I > 2σ(I)
T_min = 0.286, T_max = 0.458	R_int = 0.030
13236 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.021	H-atom parameters constrained
wR(F²) = 0.040	Δρ_max = 1.66 e Å⁻³
S = 0.91	Δρ_min = −0.71 e Å⁻³
5091 reflections	Absolute structure: Flack (1983), 1469 Friedel pairs
375 parameters	Absolute structure parameter: 0.011 (5)
13 restraints

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.81279 (1)	0.68918 (1)	0.27495 (2)	0.0123 (1)
O1	0.67839 (13)	0.6637 (3)	0.2709 (6)	0.0430 (12)
O2	0.72791 (16)	0.4501 (5)	0.2212 (3)	0.0459 (13)
O3	0.61990 (14)	0.4502 (4)	0.2321 (2)	0.0248 (10)
O4	0.80174 (17)	0.8914 (4)	0.1445 (2)	0.0298 (11)
O5	0.86851 (17)	0.6812 (4)	0.12537 (19)	0.0270 (11)
O6	0.87017 (17)	0.8896 (4)	0.0410 (2)	0.0289 (11)
N1	0.67479 (17)	0.5206 (4)	0.2413 (2)	0.0202 (11)
N2	0.84797 (18)	0.8229 (5)	0.1027 (2)	0.0190 (12)
N3	0.88824 (16)	0.4171 (4)	0.3076 (2)	0.0127 (10)
N4	0.82737 (17)	0.5960 (4)	0.4306 (2)	0.0134 (11)
N5	0.92384 (17)	0.8515 (4)	0.3302 (2)	0.0129 (10)
N6	0.79763 (16)	0.9939 (4)	0.3445 (2)	0.0132 (11)
C1	0.9218 (2)	0.4374 (5)	0.3792 (3)	0.0136 (11)
C2	0.8902 (2)	0.5331 (5)	0.4438 (3)	0.0147 (12)
C3	0.7958 (2)	0.6729 (5)	0.4913 (3)	0.0170 (14)
C4	0.8267 (2)	0.6970 (5)	0.5682 (3)	0.0213 (14)
C5	0.8905 (2)	0.6395 (5)	0.5801 (3)	0.0230 (14)
C6	0.9239 (2)	0.5531 (5)	0.5186 (3)	0.0173 (12)
C7	0.9892 (3)	0.4878 (9)	0.5286 (5)	0.0233 (18)
C8	1.0189 (2)	0.3935 (5)	0.4696 (3)	0.0210 (14)
C9	0.9856 (2)	0.3655 (5)	0.3941 (3)	0.0160 (12)
C10	1.0119 (2)	0.2629 (5)	0.3315 (3)	0.0197 (14)
C11	0.9761 (2)	0.2353 (4)	0.2627 (4)	0.0169 (19)
C12	0.9135 (2)	0.3154 (5)	0.2516 (2)	0.0168 (11)
C13	0.8733 (3)	0.2845 (5)	0.1756 (3)	0.0227 (17)
C14	0.7256 (2)	0.7309 (5)	0.4779 (3)	0.0210 (16)
C15	0.9087 (2)	0.9389 (5)	0.3990 (3)	0.0132 (11)
C16	0.8436 (2)	1.0192 (5)	0.4054 (3)	0.0140 (11)
C17	0.7408 (2)	1.0801 (5)	0.3454 (3)	0.0170 (12)
C18	0.7262 (2)	1.1946 (6)	0.4074 (3)	0.0233 (14)
C19	0.7695 (2)	1.2141 (5)	0.4706 (3)	0.0220 (16)
C20	0.8303 (2)	1.1234 (5)	0.4725 (3)	0.0197 (16)
C21	0.8778 (3)	1.1361 (5)	0.5382 (3)	0.0220 (14)
C22	0.9370 (3)	1.0579 (5)	0.5340 (3)	0.0240 (14)
C23	0.9550 (2)	0.9622 (5)	0.4634 (3)	0.0190 (14)
C24	1.0187 (2)	0.8927 (5)	0.4539 (3)	0.0220 (16)
C25	1.0347 (2)	0.8135 (5)	0.3827 (3)	0.0210 (14)
C26	0.9861 (2)	0.7931 (5)	0.3218 (3)	0.0147 (12)
C27	1.0043 (2)	0.7101 (5)	0.2427 (3)	0.0173 (12)
C28	0.69100 (18)	1.0494 (4)	0.2774 (7)	0.0222 (10)
H1	0.84510	0.38190	0.16410	0.0340*
H2	0.84480	0.18630	0.18350	0.0340*
H3	0.90380	0.26520	0.12950	0.0340*
H4	0.99300	0.16230	0.22180	0.0200*
H5	1.05490	0.21320	0.33790	0.0230*
H6	1.06200	0.34620	0.47900	0.0250*
H7	1.01310	0.51040	0.57770	0.0280*
H8	0.91240	0.65860	0.63090	0.0270*
H9	0.80340	0.75240	0.61100	0.0260*
H10	0.71350	0.71560	0.42030	0.0310*
H11	0.72210	0.84920	0.49220	0.0310*
H12	0.69500	0.66590	0.51230	0.0310*
H13	0.96550	0.71240	0.20580	0.0260*
H14	1.01730	0.59420	0.25320	0.0260*
H15	1.04190	0.76950	0.21740	0.0260*
H16	1.07890	0.77200	0.37450	0.0250*
H17	1.05080	0.90050	0.49670	0.0270*
H18	0.96750	1.06590	0.57850	0.0290*
H19	0.86700	1.20060	0.58510	0.0260*
H20	0.75900	1.28900	0.51370	0.0270*
H21	0.68610	1.25850	0.40520	0.0280*
H22	0.71420	1.00010	0.23040	0.0330*
H23	0.67040	1.15530	0.26110	0.0330*
H24	0.65600	0.97270	0.29650	0.0330*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.0120 (1)	0.0136 (1)	0.0112 (1)	−0.0004 (1)	−0.0004 (2)	−0.0012 (2)
O1	0.0227 (15)	0.0283 (15)	0.078 (3)	−0.0031 (12)	0.010 (3)	−0.026 (3)
O2	0.0156 (18)	0.041 (2)	0.081 (3)	−0.0035 (16)	0.0004 (19)	−0.036 (2)
O3	0.0145 (16)	0.0271 (17)	0.0329 (18)	−0.0074 (13)	0.0005 (15)	−0.0012 (15)
O4	0.036 (2)	0.0275 (19)	0.026 (2)	0.0107 (15)	0.0072 (17)	0.0043 (16)
O5	0.035 (2)	0.0249 (18)	0.0212 (18)	0.0146 (17)	0.0073 (16)	0.0059 (16)
O6	0.036 (2)	0.0262 (18)	0.0245 (19)	−0.0001 (15)	0.0157 (17)	0.0075 (16)
N1	0.015 (2)	0.0205 (18)	0.025 (2)	0.0011 (14)	−0.0044 (16)	−0.0020 (15)
N2	0.019 (2)	0.022 (2)	0.016 (2)	−0.0018 (18)	0.0026 (17)	−0.0026 (19)
N3	0.0139 (18)	0.0095 (17)	0.0148 (18)	−0.0008 (14)	0.0024 (14)	−0.0023 (14)
N4	0.014 (2)	0.0145 (19)	0.0117 (19)	−0.0053 (15)	0.0022 (16)	0.0006 (16)
N5	0.0123 (18)	0.0112 (17)	0.0152 (19)	−0.0040 (13)	0.0022 (16)	0.0021 (14)
N6	0.0154 (19)	0.0103 (17)	0.0140 (19)	−0.0031 (13)	0.0055 (16)	−0.0010 (14)
C1	0.013 (2)	0.0107 (19)	0.017 (2)	−0.0035 (16)	−0.0004 (18)	0.0052 (18)
C2	0.018 (2)	0.009 (2)	0.017 (2)	−0.0054 (16)	0.001 (2)	0.0047 (17)
C3	0.026 (3)	0.010 (2)	0.015 (2)	−0.0037 (17)	0.0009 (19)	0.0038 (18)
C4	0.030 (3)	0.018 (2)	0.016 (2)	−0.006 (2)	0.006 (2)	−0.005 (2)
C5	0.036 (3)	0.018 (2)	0.015 (2)	−0.006 (2)	−0.004 (2)	−0.0011 (19)
C6	0.024 (2)	0.014 (2)	0.014 (2)	−0.0049 (18)	−0.001 (2)	0.0050 (18)
C7	0.017 (4)	0.028 (3)	0.025 (2)	−0.004 (3)	−0.016 (3)	0.004 (2)
C8	0.018 (2)	0.018 (2)	0.027 (3)	0.0011 (18)	−0.007 (2)	0.011 (2)
C9	0.014 (2)	0.013 (2)	0.021 (2)	−0.0027 (16)	0.004 (2)	0.0091 (18)
C10	0.015 (2)	0.013 (2)	0.031 (3)	0.0048 (16)	0.005 (2)	0.0071 (19)
C11	0.018 (2)	0.0147 (18)	0.018 (5)	0.0016 (14)	0.008 (2)	0.0014 (19)
C12	0.020 (2)	0.0125 (18)	0.018 (2)	−0.0080 (18)	0.0029 (17)	0.0019 (19)
C13	0.031 (3)	0.018 (3)	0.019 (3)	−0.002 (2)	0.002 (2)	−0.005 (2)
C14	0.026 (3)	0.019 (2)	0.018 (3)	−0.0002 (18)	0.011 (2)	−0.0016 (19)
C15	0.015 (2)	0.0085 (19)	0.016 (2)	−0.0037 (16)	0.0011 (19)	0.0079 (18)
C16	0.020 (2)	0.0061 (19)	0.016 (2)	−0.0048 (16)	0.005 (2)	0.0034 (17)
C17	0.017 (2)	0.014 (2)	0.020 (2)	−0.0009 (18)	0.006 (2)	0.0031 (19)
C18	0.021 (2)	0.019 (2)	0.030 (3)	0.003 (2)	0.007 (2)	−0.001 (2)
C19	0.031 (3)	0.016 (2)	0.019 (3)	−0.0051 (19)	0.013 (2)	−0.0041 (19)
C20	0.025 (3)	0.013 (2)	0.021 (3)	−0.0071 (17)	0.008 (2)	−0.0013 (19)
C21	0.036 (3)	0.017 (2)	0.013 (2)	−0.010 (2)	0.000 (2)	−0.0008 (18)
C22	0.035 (3)	0.022 (2)	0.015 (2)	−0.013 (2)	−0.009 (2)	0.002 (2)
C23	0.025 (3)	0.016 (2)	0.016 (2)	−0.0101 (18)	−0.003 (2)	0.0034 (18)
C24	0.020 (3)	0.022 (2)	0.024 (3)	−0.0088 (19)	−0.008 (2)	0.006 (2)
C25	0.015 (2)	0.025 (2)	0.023 (3)	−0.003 (2)	−0.002 (2)	0.008 (2)
C26	0.015 (2)	0.008 (2)	0.021 (2)	−0.0051 (18)	0.003 (2)	0.003 (2)
C27	0.012 (2)	0.019 (2)	0.021 (2)	−0.0039 (19)	0.0028 (19)	0.000 (2)
C28	0.0195 (17)	0.0201 (16)	0.0269 (19)	0.0059 (15)	−0.003 (4)	0.004 (5)

Geometric parameters (Å, º) top

Pb1—O1	2.685 (3)	C15—C23	1.412 (6)
Pb1—O2	2.703 (4)	C16—C20	1.405 (6)
Pb1—O4	2.689 (3)	C17—C18	1.399 (7)
Pb1—O5	2.687 (3)	C17—C28	1.511 (10)
Pb1—N3	2.702 (3)	C18—C19	1.355 (6)
Pb1—N4	2.669 (3)	C19—C20	1.413 (6)
Pb1—N5	2.721 (3)	C20—C21	1.435 (7)
Pb1—N6	2.712 (3)	C21—C22	1.337 (8)
O1—N1	1.247 (5)	C22—C23	1.432 (7)
O2—N1	1.244 (5)	C23—C24	1.394 (6)
O3—N1	1.240 (4)	C24—C25	1.364 (7)
O4—N2	1.272 (5)	C25—C26	1.399 (6)
O5—N2	1.263 (5)	C26—C27	1.499 (7)
O6—N2	1.225 (5)	C4—H9	0.9500
N3—C1	1.358 (6)	C5—H8	0.9500
N3—C12	1.326 (5)	C7—H7	0.9500
N4—C2	1.366 (5)	C8—H6	0.9500
N4—C3	1.327 (6)	C10—H5	0.9500
N5—C15	1.360 (6)	C11—H4	0.9500
N5—C26	1.333 (5)	C13—H1	0.9800
N6—C16	1.368 (6)	C13—H2	0.9800
N6—C17	1.326 (5)	C13—H3	0.9800
C1—C2	1.450 (6)	C14—H10	0.9800
C1—C9	1.416 (6)	C14—H11	0.9800
C2—C6	1.405 (7)	C14—H12	0.9800
C3—C4	1.414 (7)	C18—H21	0.9500
C3—C14	1.490 (6)	C19—H20	0.9500
C4—C5	1.366 (6)	C21—H19	0.9500
C5—C6	1.391 (6)	C22—H18	0.9500
C6—C7	1.412 (7)	C24—H17	0.9500
C7—C8	1.361 (9)	C25—H16	0.9500
C8—C9	1.420 (7)	C27—H13	0.9800
C9—C10	1.414 (6)	C27—H14	0.9800
C10—C11	1.351 (7)	C27—H15	0.9800
C11—C12	1.414 (6)	C28—H22	0.9800
C12—C13	1.499 (6)	C28—H23	0.9800
C15—C16	1.451 (6)	C28—H24	0.9800

Pb1···H1	3.1300	C14···C16	3.503 (6)
Pb1···H10	3.1000	C15···C11^vii	3.524 (7)
Pb1···H13	3.2500	C15···C10^vii	3.492 (6)
Pb1···H22	3.2600	C15···C3	3.447 (6)
O1···O2	2.137 (6)	C15···C2	3.355 (6)
O1···C28	3.104 (4)	C16···C3	3.254 (6)
O1···C25ⁱ	3.401 (7)	C16···C14	3.503 (6)
O2···C4ⁱⁱ	3.401 (6)	C17···C14	3.554 (6)
O2···C13	3.272 (7)	C18···O6^ix	3.302 (6)
O2···O1	2.137 (6)	C19···N2^ix	3.302 (6)
O3···C11ⁱⁱⁱ	3.266 (5)	C19···O6^ix	3.323 (5)
O3···C10ⁱⁱⁱ	3.192 (5)	C19···N4^vii	3.336 (5)
O4···O5	2.169 (5)	C19···C2^vii	3.537 (6)
O4···C28	3.346 (9)	C20···C2^vii	3.526 (6)
O5···C13	3.286 (5)	C20···C1^vii	3.462 (6)
O5···C27	3.324 (5)	C21···C6^vii	3.482 (6)
O5···O4	2.169 (5)	C21···C7^vii	3.591 (8)
O6···C19ⁱⁱ	3.323 (5)	C21···C2^vii	3.546 (6)
O6···C8^iv	3.376 (5)	C22···C8^vii	3.318 (6)
O6···C18ⁱⁱ	3.302 (6)	C22···C9^vii	3.501 (6)
O6···C24^v	3.158 (5)	C22···C5	3.561 (6)
O1···H16ⁱ	2.6600	C23···C10^vii	3.428 (6)
O1···H24	2.5500	C23···C6	3.458 (6)
O1···H15ⁱ	2.9100	C23···C5	3.462 (6)
O1···H22	2.8700	C23···C9^vii	3.480 (6)
O1···H10	2.5800	C24···C6	3.478 (6)
O2···H23^vi	2.7100	C24···C10^vii	3.583 (6)
O2···H1	2.5700	C24···C7	3.518 (8)
O2···H9ⁱⁱ	2.4800	C24···O6^xii	3.158 (5)
O3···H15ⁱ	2.7400	C25···O1^xiii	3.401 (7)
O3···H5ⁱⁱⁱ	2.5300	C26···C1	3.264 (6)
O3···H4ⁱⁱⁱ	2.6900	C26···C2	3.461 (6)
O3···H23^vi	2.6100	C27···O5	3.324 (5)
O4···H22	2.4000	C27···C1	3.531 (6)
O4···H20ⁱⁱ	2.5900	C28···O1	3.104 (4)
O4···H2^vii	2.5900	C28···O4	3.346 (9)
O5···H6^iv	2.7700	C1···H14	3.0700
O5···H13	2.3500	C9···H14	3.0100
O5···H1	2.5300	C10···H14	2.9500
O6···H17^v	2.4200	C11···H14	3.0000
O6···H6^iv	2.5400	C12···H14	3.0400
O6···H12^viii	2.6100	C17···H11	3.0500
O6···H20ⁱⁱ	2.7300	C18···H11	3.1000
O6···H21ⁱⁱ	2.7000	C19···H11	3.0900
N2···C19ⁱⁱ	3.302 (6)	C20···H11	3.1000
N3···N4	2.752 (5)	H1···Pb1	3.1300
N3···C2	2.415 (6)	H1···O2	2.5700
N4···C16	3.433 (5)	H1···O5	2.5300
N4···C1	2.421 (5)	H2···O4^vi	2.5900
N4···N3	2.752 (5)	H3···H4	2.4700
N4···N5	3.253 (5)	H3···H7^iv	2.5900
N4···C19^vi	3.336 (5)	H4···H3	2.4700
N4···C15	3.232 (5)	H4···O3^xi	2.6900
N5···C16	2.424 (5)	H5···H6	2.5500
N5···C11^vii	3.431 (5)	H5···O3^xi	2.5300
N5···N4	3.253 (5)	H6···H5	2.5500
N5···N6	2.771 (5)	H6···O5^x	2.7700
N5···C1	3.416 (5)	H6···O6^x	2.5400
N5···C2	3.228 (5)	H7···H8	2.4900
N6···C14	3.356 (5)	H7···H3^x	2.5900
N6···N5	2.771 (5)	H8···H7	2.4900
N6···C15	2.425 (5)	H9···O2^ix	2.4800
N1···H23^vi	2.9500	H10···Pb1	3.1000
N2···H20ⁱⁱ	2.5900	H10···O1	2.5800
C1···C20^vi	3.462 (6)	H11···C17	3.0500
C1···C26	3.264 (6)	H11···C18	3.1000
C1···C27	3.531 (6)	H11···C19	3.0900
C2···C20^vi	3.526 (6)	H11···C20	3.1000
C2···C15	3.355 (6)	H12···O6^xiv	2.6100
C2···C19^vi	3.537 (6)	H13···Pb1	3.2500
C2···C21^vi	3.546 (6)	H13···O5	2.3500
C2···C26	3.461 (6)	H14···C1	3.0700
C3···C16	3.254 (6)	H14···C9	3.0100
C3···C15	3.447 (6)	H14···C10	2.9500
C4···O2^ix	3.401 (6)	H14···C11	3.0000
C5···C23	3.462 (6)	H14···C12	3.0400
C5···C22	3.561 (6)	H15···O1^xiii	2.9100
C6···C24	3.478 (6)	H15···O3^xiii	2.7400
C6···C21^vi	3.482 (6)	H16···O1^xiii	2.6600
C6···C23	3.458 (6)	H17···H18	2.5100
C7···C24	3.518 (8)	H17···O6^xii	2.4200
C7···C21^vi	3.591 (8)	H18···H17	2.5100
C8···C22^vi	3.318 (6)	H19···H20	2.5500
C8···O6^x	3.376 (5)	H20···H19	2.5500
C9···C22^vi	3.501 (6)	H20···O4^ix	2.5900
C9···C23^vi	3.480 (6)	H20···O6^ix	2.7300
C10···C23^vi	3.428 (6)	H20···N2^ix	2.5900
C10···C24^vi	3.583 (6)	H21···H23	2.5200
C10···C15^vi	3.492 (6)	H21···O6^ix	2.7000
C10···O3^xi	3.192 (5)	H22···Pb1	3.2600
C11···C15^vi	3.524 (7)	H22···O1	2.8700
C11···O3^xi	3.266 (5)	H22···O4	2.4000
C11···N5^vi	3.431 (5)	H23···O2^vii	2.7100
C13···O2	3.272 (7)	H23···O3^vii	2.6100
C13···O5	3.286 (5)	H23···N1^vii	2.9500
C14···C17	3.554 (6)	H23···H21	2.5200
C14···N6	3.356 (5)	H24···O1	2.5500

O1—Pb1—O2	46.73 (13)	C11—C12—C13	120.2 (4)
O1—Pb1—O4	86.83 (18)	N5—C15—C16	119.1 (4)
O1—Pb1—O5	112.8 (2)	N5—C15—C23	122.7 (4)
O1—Pb1—N3	119.85 (10)	C16—C15—C23	118.1 (4)
O1—Pb1—N4	96.4 (2)	N6—C16—C15	118.7 (4)
O1—Pb1—N5	148.75 (15)	N6—C16—C20	122.1 (4)
O1—Pb1—N6	88.16 (12)	C15—C16—C20	119.3 (4)
O2—Pb1—O4	96.79 (12)	N6—C17—C18	121.8 (4)
O2—Pb1—O5	86.86 (12)	N6—C17—C28	117.9 (4)
O2—Pb1—N3	80.77 (10)	C18—C17—C28	120.3 (4)
O2—Pb1—N4	100.36 (12)	C17—C18—C19	119.8 (4)
O2—Pb1—N5	162.89 (10)	C18—C19—C20	120.2 (4)
O2—Pb1—N6	134.89 (10)	C16—C20—C19	116.8 (4)
O4—Pb1—O5	47.60 (10)	C16—C20—C21	120.2 (4)
O4—Pb1—N3	133.56 (10)	C19—C20—C21	123.0 (4)
O4—Pb1—N4	159.17 (10)	C20—C21—C22	120.6 (4)
O4—Pb1—N5	92.39 (10)	C21—C22—C23	120.9 (5)
O4—Pb1—N6	77.33 (10)	C15—C23—C22	120.6 (4)
O5—Pb1—N3	86.05 (10)	C15—C23—C24	117.3 (4)
O5—Pb1—N4	144.77 (10)	C22—C23—C24	122.1 (4)
O5—Pb1—N5	88.75 (10)	C23—C24—C25	119.6 (4)
O5—Pb1—N6	116.70 (10)	C24—C25—C26	120.1 (4)
N3—Pb1—N4	61.64 (10)	N5—C26—C25	122.0 (4)
N3—Pb1—N5	82.44 (10)	N5—C26—C27	118.0 (4)
N3—Pb1—N6	134.93 (10)	C25—C26—C27	120.0 (4)
N4—Pb1—N5	74.25 (10)	C3—C4—H9	120.00
N4—Pb1—N6	82.19 (10)	C5—C4—H9	120.00
N5—Pb1—N6	61.33 (10)	C4—C5—H8	120.00
Pb1—O1—N1	97.9 (2)	C6—C5—H8	120.00
Pb1—O2—N1	97.1 (3)	C6—C7—H7	119.00
Pb1—O4—N2	96.1 (2)	C8—C7—H7	119.00
Pb1—O5—N2	96.4 (2)	C7—C8—H6	120.00
O1—N1—O2	118.2 (3)	C9—C8—H6	120.00
O1—N1—O3	121.1 (3)	C9—C10—H5	120.00
O2—N1—O3	120.7 (3)	C11—C10—H5	120.00
O4—N2—O5	117.7 (3)	C10—C11—H4	120.00
O4—N2—O6	121.1 (4)	C12—C11—H4	120.00
O5—N2—O6	121.2 (4)	C12—C13—H1	109.00
Pb1—N3—C1	110.3 (2)	C12—C13—H2	109.00
Pb1—N3—C12	124.8 (2)	C12—C13—H3	109.00
C1—N3—C12	118.9 (3)	H1—C13—H2	109.00
Pb1—N4—C2	110.7 (3)	H1—C13—H3	109.00
Pb1—N4—C3	122.2 (3)	H2—C13—H3	109.00
C2—N4—C3	119.2 (4)	C3—C14—H10	109.00
Pb1—N5—C15	110.0 (2)	C3—C14—H11	110.00
Pb1—N5—C26	123.7 (3)	C3—C14—H12	109.00
C15—N5—C26	118.2 (4)	H10—C14—H11	109.00
Pb1—N6—C16	111.4 (2)	H10—C14—H12	109.00
Pb1—N6—C17	124.7 (3)	H11—C14—H12	109.00
C16—N6—C17	119.1 (4)	C17—C18—H21	120.00
N3—C1—C2	118.6 (4)	C19—C18—H21	120.00
N3—C1—C9	122.8 (4)	C18—C19—H20	120.00
C2—C1—C9	118.7 (4)	C20—C19—H20	120.00
N4—C2—C1	118.5 (4)	C20—C21—H19	120.00
N4—C2—C6	122.2 (4)	C22—C21—H19	120.00
C1—C2—C6	119.2 (4)	C21—C22—H18	120.00
N4—C3—C4	121.5 (4)	C23—C22—H18	120.00
N4—C3—C14	118.7 (4)	C23—C24—H17	120.00
C4—C3—C14	119.8 (4)	C25—C24—H17	120.00
C3—C4—C5	119.1 (4)	C24—C25—H16	120.00
C4—C5—C6	120.7 (4)	C26—C25—H16	120.00
C2—C6—C5	117.3 (4)	C26—C27—H13	109.00
C2—C6—C7	119.9 (5)	C26—C27—H14	109.00
C5—C6—C7	122.8 (5)	C26—C27—H15	109.00
C6—C7—C8	121.6 (6)	H13—C27—H14	110.00
C7—C8—C9	120.1 (4)	H13—C27—H15	109.00
C1—C9—C8	120.3 (4)	H14—C27—H15	109.00
C1—C9—C10	116.4 (4)	C17—C28—H22	109.00
C8—C9—C10	123.3 (4)	C17—C28—H23	110.00
C9—C10—C11	120.2 (4)	C17—C28—H24	110.00
C10—C11—C12	119.9 (4)	H22—C28—H23	109.00
N3—C12—C11	121.7 (4)	H22—C28—H24	109.00
N3—C12—C13	118.2 (4)	H23—C28—H24	109.00

O2—Pb1—O1—N1	2.2 (3)	Pb1—O5—N2—O6	167.8 (3)
O4—Pb1—O1—N1	104.6 (5)	Pb1—N3—C1—C2	33.0 (4)
O5—Pb1—O1—N1	63.7 (5)	Pb1—N3—C1—C9	−148.7 (3)
N3—Pb1—O1—N1	−35.2 (6)	C12—N3—C1—C2	−172.9 (4)
N4—Pb1—O1—N1	−96.1 (5)	C12—N3—C1—C9	5.5 (6)
N5—Pb1—O1—N1	−166.0 (3)	Pb1—N3—C12—C11	146.5 (3)
N6—Pb1—O1—N1	−178.0 (5)	Pb1—N3—C12—C13	−34.4 (5)
O1—Pb1—O2—N1	−2.2 (3)	C1—N3—C12—C11	−3.6 (6)
O4—Pb1—O2—N1	−81.3 (3)	C1—N3—C12—C13	175.5 (4)
O5—Pb1—O2—N1	−128.0 (3)	Pb1—N4—C2—C1	−35.5 (4)
N3—Pb1—O2—N1	145.5 (3)	Pb1—N4—C2—C6	146.8 (3)
N4—Pb1—O2—N1	86.8 (3)	C3—N4—C2—C1	174.9 (4)
N6—Pb1—O2—N1	−2.5 (4)	C3—N4—C2—C6	−2.8 (6)
O1—Pb1—O4—N2	−133.4 (3)	Pb1—N4—C3—C4	−143.4 (3)
O2—Pb1—O4—N2	−87.6 (2)	Pb1—N4—C3—C14	38.1 (5)
O5—Pb1—O4—N2	−8.2 (2)	C2—N4—C3—C4	2.6 (6)
N3—Pb1—O4—N2	−3.9 (3)	C2—N4—C3—C14	−176.0 (4)
N4—Pb1—O4—N2	127.1 (3)	Pb1—N5—C15—C16	−37.0 (4)
N5—Pb1—O4—N2	77.9 (2)	Pb1—N5—C15—C23	146.2 (3)
N6—Pb1—O4—N2	137.8 (2)	C26—N5—C15—C16	173.3 (4)
O1—Pb1—O5—N2	70.6 (2)	C26—N5—C15—C23	−3.5 (6)
O2—Pb1—O5—N2	110.4 (2)	Pb1—N5—C26—C25	−142.7 (3)
O4—Pb1—O5—N2	8.3 (2)	Pb1—N5—C26—C27	40.0 (5)
N3—Pb1—O5—N2	−168.6 (2)	C15—N5—C26—C25	2.6 (6)
N4—Pb1—O5—N2	−146.0 (2)	C15—N5—C26—C27	−174.7 (4)
N5—Pb1—O5—N2	−86.1 (2)	Pb1—N6—C16—C15	30.5 (4)
N6—Pb1—O5—N2	−29.4 (3)	Pb1—N6—C16—C20	−151.2 (3)
O1—Pb1—N3—C1	−115.3 (3)	C17—N6—C16—C15	−173.1 (4)
O1—Pb1—N3—C12	92.4 (4)	C17—N6—C16—C20	5.3 (6)
O2—Pb1—N3—C1	−142.0 (3)	Pb1—N6—C17—C18	152.3 (3)
O2—Pb1—N3—C12	65.8 (3)	Pb1—N6—C17—C28	−26.9 (6)
O4—Pb1—N3—C1	127.4 (3)	C16—N6—C17—C18	−0.8 (6)
O4—Pb1—N3—C12	−24.8 (4)	C16—N6—C17—C28	−180.0 (4)
O5—Pb1—N3—C1	130.6 (3)	N3—C1—C2—N4	1.3 (6)
O5—Pb1—N3—C12	−21.7 (3)	N3—C1—C2—C6	179.1 (4)
N4—Pb1—N3—C1	−34.8 (3)	C9—C1—C2—N4	−177.1 (4)
N4—Pb1—N3—C12	173.0 (3)	C9—C1—C2—C6	0.7 (6)
N5—Pb1—N3—C1	41.3 (3)	N3—C1—C9—C8	178.8 (4)
N5—Pb1—N3—C12	−110.9 (3)	N3—C1—C9—C10	−3.1 (6)
N6—Pb1—N3—C1	6.0 (3)	C2—C1—C9—C8	−2.8 (6)
N6—Pb1—N3—C12	−146.2 (3)	C2—C1—C9—C10	175.3 (4)
O1—Pb1—N4—C2	156.1 (3)	N4—C2—C6—C5	0.5 (6)
O1—Pb1—N4—C3	−55.4 (3)	N4—C2—C6—C7	−179.0 (5)
O2—Pb1—N4—C2	109.0 (3)	C1—C2—C6—C5	−177.2 (4)
O2—Pb1—N4—C3	−102.5 (3)	C1—C2—C6—C7	3.3 (7)
O4—Pb1—N4—C2	−106.1 (3)	N4—C3—C4—C5	−0.1 (6)
O4—Pb1—N4—C3	42.4 (5)	C14—C3—C4—C5	178.4 (4)
O5—Pb1—N4—C2	9.6 (3)	C3—C4—C5—C6	−2.3 (6)
O5—Pb1—N4—C3	158.1 (3)	C4—C5—C6—C2	2.1 (6)
N3—Pb1—N4—C2	35.5 (2)	C4—C5—C6—C7	−178.5 (5)
N3—Pb1—N4—C3	−176.0 (3)	C2—C6—C7—C8	−5.3 (9)
N5—Pb1—N4—C2	−54.4 (3)	C5—C6—C7—C8	175.2 (5)
N5—Pb1—N4—C3	94.1 (3)	C6—C7—C8—C9	3.2 (9)
N6—Pb1—N4—C2	−116.7 (3)	C7—C8—C9—C1	0.9 (7)
N6—Pb1—N4—C3	31.8 (3)	C7—C8—C9—C10	−177.0 (5)
O1—Pb1—N5—C15	21.7 (5)	C1—C9—C10—C11	−1.2 (6)
O1—Pb1—N5—C26	169.5 (4)	C8—C9—C10—C11	176.9 (4)
O4—Pb1—N5—C15	109.5 (3)	C9—C10—C11—C12	2.9 (6)
O4—Pb1—N5—C26	−102.7 (3)	C10—C11—C12—N3	−0.5 (6)
O5—Pb1—N5—C15	157.0 (3)	C10—C11—C12—C13	−179.6 (4)
O5—Pb1—N5—C26	−55.3 (3)	N5—C15—C16—N6	4.8 (6)
N3—Pb1—N5—C15	−116.8 (3)	N5—C15—C16—C20	−173.6 (4)
N3—Pb1—N5—C26	30.9 (3)	C23—C15—C16—N6	−178.2 (4)
N4—Pb1—N5—C15	−54.3 (3)	C23—C15—C16—C20	3.4 (6)
N4—Pb1—N5—C26	93.5 (3)	N5—C15—C23—C22	178.9 (4)
N6—Pb1—N5—C15	35.4 (3)	N5—C15—C23—C24	0.7 (6)
N6—Pb1—N5—C26	−176.9 (4)	C16—C15—C23—C22	2.0 (6)
O1—Pb1—N6—C16	139.5 (3)	C16—C15—C23—C24	−176.2 (4)
O1—Pb1—N6—C17	−15.4 (4)	N6—C16—C20—C19	−5.9 (6)
O2—Pb1—N6—C16	139.7 (3)	N6—C16—C20—C21	175.1 (4)
O2—Pb1—N6—C17	−15.2 (4)	C15—C16—C20—C19	172.5 (4)
O4—Pb1—N6—C16	−133.3 (3)	C15—C16—C20—C21	−6.6 (6)
O4—Pb1—N6—C17	71.8 (3)	N6—C17—C18—C19	−2.9 (7)
O5—Pb1—N6—C16	−105.8 (3)	C28—C17—C18—C19	176.2 (5)
O5—Pb1—N6—C17	99.3 (3)	C17—C18—C19—C20	2.2 (7)
N3—Pb1—N6—C16	7.4 (3)	C18—C19—C20—C16	2.0 (6)
N3—Pb1—N6—C17	−147.5 (3)	C18—C19—C20—C21	−178.9 (4)
N4—Pb1—N6—C16	42.9 (3)	C16—C20—C21—C22	4.4 (7)
N4—Pb1—N6—C17	−112.0 (3)	C19—C20—C21—C22	−174.6 (4)
N5—Pb1—N6—C16	−33.4 (3)	C20—C21—C22—C23	1.2 (7)
N5—Pb1—N6—C17	171.7 (4)	C21—C22—C23—C15	−4.4 (7)
Pb1—O1—N1—O2	−4.0 (6)	C21—C22—C23—C24	173.7 (4)
Pb1—O1—N1—O3	176.0 (3)	C15—C23—C24—C25	3.1 (6)
Pb1—O2—N1—O1	3.9 (6)	C22—C23—C24—C25	−175.1 (4)
Pb1—O2—N1—O3	−176.1 (3)	C23—C24—C25—C26	−4.0 (6)
Pb1—O4—N2—O5	14.7 (4)	C24—C25—C26—N5	1.1 (6)
Pb1—O4—N2—O6	−167.8 (3)	C24—C25—C26—C27	178.4 (4)
Pb1—O5—N2—O4	−14.7 (4)

Symmetry codes: (i) x−1/2, −y+7/2, z; (ii) −x+3/2, y−1/2, z−1/2; (iii) x−1/2, −y+5/2, z; (iv) −x+2, −y+3, z−1/2; (v) −x+2, −y+4, z−1/2; (vi) x, y−1, z; (vii) x, y+1, z; (viii) −x+3/2, y+1/2, z−1/2; (ix) −x+3/2, y+1/2, z+1/2; (x) −x+2, −y+3, z+1/2; (xi) x+1/2, −y+5/2, z; (xii) −x+2, −y+4, z+1/2; (xiii) x+1/2, −y+7/2, z; (xiv) −x+3/2, y−1/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H1···O2	0.98	2.57	3.272 (7)	128
C13—H1···O5	0.98	2.53	3.286 (5)	134
C13—H2···O4^vi	0.98	2.59	3.496 (5)	153
C10—H5···O3^xi	0.95	2.53	3.192 (5)	127
C8—H6···O6^x	0.95	2.54	3.376 (5)	147
C4—H9···O2^ix	0.95	2.48	3.401 (6)	163
C14—H10···O1	0.98	2.58	3.555 (11)	177
C27—H13···O5	0.98	2.35	3.324 (5)	172
C24—H17···O6^xii	0.95	2.42	3.158 (5)	135
C19—H20···O4^ix	0.95	2.59	3.482 (6)	156
C28—H22···O4	0.98	2.40	3.346 (9)	161
C28—H24···O1	0.98	2.55	3.104 (4)	116
C14—H11···Cg4	0.98	2.77	3.415 (4)	124
C27—H14···Cg1	0.98	2.69	3.419 (4)	131

Symmetry codes: (vi) x, y−1, z; (ix) −x+3/2, y+1/2, z+1/2; (x) −x+2, −y+3, z+1/2; (xi) x+1/2, −y+5/2, z; (xii) −x+2, −y+4, z+1/2.

Experimental details

Crystal data
Chemical formula	[Pb(NO₃)₂(C₁₄H₁₂N₂)₂]
M_r	747.73
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	100
a, b, c (Å)	19.9164 (4), 8.0173 (1), 16.3575 (3)
V (Å³)	2611.90 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	6.52
Crystal size (mm)	0.32 × 0.18 × 0.12

Data collection
Diffractometer	Oxford Diffraction Gemini-S CCD diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.286, 0.458
No. of measured, independent and observed [I > 2σ(I)] reflections	13236, 5091, 4126
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.684

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.021, 0.040, 0.91
No. of reflections	5091
No. of parameters	375
No. of restraints	13
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.66, −0.71
Absolute structure	Flack (1983), 1469 Friedel pairs
Absolute structure parameter	0.011 (5)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected bond lengths (Å) top

Pb1—O1	2.685 (3)	Pb1—N3	2.702 (3)
Pb1—O2	2.703 (4)	Pb1—N4	2.669 (3)
Pb1—O4	2.689 (3)	Pb1—N5	2.721 (3)
Pb1—O5	2.687 (3)	Pb1—N6	2.712 (3)