Bis(μ-4-hydroxy­benzoato-κ²O:O′)bis­[(2,9-dimethyl-1,10-phenanthroline-κ²N,N′)(4-hydroxy­benzoato-κ²O,O′)lead(II)]

In the centrosymmetric binuclear title complex, [Pb₂(C₇H₅O₃)₄(C₁₄H₁₂N₂)₂], each Pb^II ion is coordinated by two N atoms from a 2,9-dimethyl-1,10-phenanthroline (dmphen) ligand and four O atoms from three 4-hydroxy­benzoate anions in a distorted octa­hedral environment. The 4-hydroxy­benzoate groups coordinate to each Pb^II atom in two different ways. Two 4-hydroxy­benzoate ions behave as chelating ligands to a single Pb atom, and the other two form bridges between the two Pb atoms, forming a centrosymmetric eight-membered ring in the binuclear structure. Mol­ecules are linked into a two-dimensional framework by O—H...O hydrogen bonds. The packing is further stabilized by π–π inter­actions between the dmphen rings of neighboring mol­ecules, with a distance of 3.327 Å between the planes of the dmphen ligands.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.018
• wR factor = 0.042
• Data-to-parameter ratio = 14.1

checkCIF/PLATON results

No syntax errors found



Alert level C
ABSTM02_ALERT_3_C  The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
            Tmin and Tmax reported:      0.277     0.396
            Tmin and Tmax expected:      0.201     0.323
            RR =      1.125
            Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large .......       1.11
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.82
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       2.78 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Pb1    -   O1      ..       7.24 su
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.816
            Tmax scaled      0.323 Tmin scaled      0.226
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Pb1         (2)       2.07

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

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

---

S1. Comment

The coordination chemistry of lead(II) with N and O donor ligands has been investigated in the past decade and is frequently discussed as lead is an environmental pollutant with severe toxic effects (Shimoni-Livny et al., 2003). Because of its electronic configuration and size, Pb(II) exhibits various coordination numbers and geometries. A number of lead(II) complexes with different donor ligands have been synthesized and studied by X-ray crystallography (Mahjoub & Morsali, 2002; Morsali et al., 2003; Li et al., 2005; Zhang et al., 2005; Xuan & Zhao, 2007). The title complex, (I), was recently obtained from the reaction of lead acetate, sodium 4-hydroxybenzoate and dmphen in an ethanol/water mixture, and its crystal structure is reported here.

Each Pb^II ion is six-coordinated by the two N atoms from a dmphen ligand, and four carbonyl O atoms from three 4-hydroxybenzoate ligands (Fig.1). The four Pb—O bond lengths are significantly different, as are the two Pb—N bond lengths and each Pb^II cation lies at the center of a distorted octahedron. The Pb—O—C—O bridging interaction, forms a centrosymmetric eight-membered Pb₂O₄C₂ ring with a Pb···Pb distance of 4.2639 (3) Å.

In the crystal structure, molecules are linked into a two dimensional framework by intermolecular O—H···O hydrogen (Fig.2). The packing is further stabilized by π-π interactions between the dmphen rings of neighboring molecules. The distance between the parallel planes (N1/C1—C10/ N2/C11/C12) [symmetry code: -x + 1, -y + 2, -z + 1] of neighboring molecules is 3.3272 Å. This combination of hydrogen bonds and π-π stacking interactions builds a three-dimensional network architecture.

Related literature

For the background to lead coordination chemistry, see: Shimoni-Livny et al. (1998). For related structures, see: Li et al. (2005); Mahjoub & Morsali (2002); Morsali, Mahjoub et al. (2003); Morsali, Payeghader et al. (2003); Xuan & Zhao (2007); Zhang & Lu (2005).

S2. Experimental

4-hydroxybenzoic acid (0.0691 g, 0.5 mmol) and NaOH (0.0182 g, 0.5 > mmol) were dissolved in distilled water (10 ml) and Pb(CH₃COOH)₂^.3H₂O (0.1897 g, 0.5 mmol) was added. This solution was added to a solution of 2,9-dimethyl-1,10-phenanthroline hemihydrate (C₁₄H₁₂N₂^.0.5H₂O, 0.1090 g, 0.5 mmol) in ethanol (10 ml). The mixture was stirred at 323 K and then refluxed for 4 h, cooled to room temperature and filtered. Bright colorless single crystals of (I) appeared over a period of four days by slow evaporation at room temperature.

S3. Refinement

Methyl H and hydroxy H atoms were placed in calculated positions,with C—H = 0.96 and O—H = 0.82 Å, and refined with free torsion angles to fit the electron density; U_iso(H) = 1.5U_eq(carrier). Other H atoms were placed in calculated positions, with C—H=0.93 Å, and refined using the riding-model approximation with U_iso(H) = 1.2U_eq(C).

Computing details

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

Figures

	Fig. 1. The molecular structure of the title complex(I), with atom labels and 30% probability displacement ellipsoids. [Symmetry codes:(A)-x + 1, -y + 2, -z + 1]
	Fig. 2. The hydrogen-bonding motifs in the crystal structure of (I). Dashed lines indicate the hydrogen bonds.
	Fig. 3. π-π interactions between the dmphen rings of neighboring molecules in the crystal structure of (I).

Bis(µ-4-hydroxybenzoato-κ²O:O')bis[(2,9-dimethyl-1,10- phenanthroline-κ²N,N')(4-hydroxybenzoato- κ²O,O')lead(II)]

Crystal data

[Pb2(C7H5O3)4(C14H12N2)2]	F(000) = 1336
Mr = 1379.35	Dx = 1.793 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8418 reflections
a = 11.0539 (9) Å	θ = 2.6–28.1°
b = 20.9060 (16) Å	µ = 6.65 mm^−1
c = 11.2905 (9) Å	T = 293 K
β = 101.667 (1)°	Block, colorless
V = 2555.2 (4) Å^3	0.26 × 0.21 × 0.17 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	4760 independent reflections
Radiation source: fine-focus sealed tube	4180 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.021
ϕ and ω scans	θmax = 25.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −13→13
Tmin = 0.277, Tmax = 0.396	k = −25→25
17442 measured reflections	l = −13→13

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.042	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.0193P)^2 + 1.4405P] where P = (Fo^2 + 2Fc^2)/3
4760 reflections	(Δ/σ)max = 0.008
338 parameters	Δρmax = 0.49 e Å^−3
0 restraints	Δρmin = −0.56 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
Pb1	0.348130 (9)	1.006948 (4)	0.350408 (8)	0.03245 (3)
O1	0.20574 (17)	1.10887 (8)	0.32230 (17)	0.0458 (5)
O2	0.32361 (17)	1.09044 (8)	0.19066 (16)	0.0407 (4)
O3	0.1365 (2)	1.37068 (9)	0.03074 (19)	0.0613 (6)
H3	0.1626	1.3744	−0.0320	0.092*
O4	0.3130 (2)	0.89345 (9)	0.41329 (18)	0.0572 (6)
O5	0.4729 (3)	0.90298 (13)	0.5611 (3)	0.1133 (11)
O6	0.17088 (18)	0.68062 (9)	0.75700 (18)	0.0509 (5)
H6	0.2228	0.6634	0.8095	0.076*
N1	0.16493 (18)	0.96424 (9)	0.20827 (18)	0.0304 (5)
N2	0.40432 (19)	0.95256 (10)	0.17560 (19)	0.0370 (5)
C1	0.0516 (2)	0.96366 (12)	0.2313 (2)	0.0381 (6)
C2	−0.0479 (3)	0.94005 (15)	0.1465 (3)	0.0536 (8)
H2	−0.1265	0.9398	0.1642	0.064*
C3	−0.0309 (3)	0.91738 (15)	0.0379 (3)	0.0554 (8)
H3A	−0.0982	0.9029	−0.0191	0.066*
C4	0.0881 (3)	0.91577 (13)	0.0120 (2)	0.0427 (7)
C5	0.1137 (3)	0.89075 (15)	−0.0979 (3)	0.0563 (9)
H5	0.0490	0.8762	−0.1578	0.068*
C6	0.2297 (3)	0.88786 (15)	−0.1160 (3)	0.0571 (9)
H6A	0.2441	0.8722	−0.1890	0.068*
C7	0.3317 (3)	0.90852 (13)	−0.0251 (2)	0.0464 (7)
C8	0.4554 (3)	0.90407 (16)	−0.0384 (3)	0.0640 (9)
H8	0.4740	0.8895	−0.1104	0.077*
C9	0.5475 (3)	0.92142 (18)	0.0556 (3)	0.0691 (10)
H9	0.6294	0.9174	0.0482	0.083*
C10	0.5203 (3)	0.94512 (16)	0.1627 (3)	0.0547 (8)
C11	0.3103 (2)	0.93440 (11)	0.0837 (2)	0.0349 (6)
C12	0.1850 (2)	0.93923 (11)	0.1022 (2)	0.0334 (6)
C13	0.0322 (3)	0.98732 (14)	0.3514 (3)	0.0518 (8)
H13A	0.1085	0.9846	0.4096	0.078*
H13B	−0.0292	0.9615	0.3777	0.078*
H13C	0.0050	1.0310	0.3439	0.078*
C14	0.6209 (3)	0.9627 (2)	0.2687 (3)	0.0871 (13)
H14A	0.6186	1.0079	0.2830	0.131*
H14B	0.6997	0.9514	0.2516	0.131*
H14C	0.6085	0.9401	0.3393	0.131*
C15	0.2559 (2)	1.12721 (11)	0.2362 (2)	0.0337 (6)
C16	0.2293 (2)	1.19281 (11)	0.1859 (2)	0.0327 (6)
C17	0.1416 (2)	1.23151 (12)	0.2226 (2)	0.0398 (7)
H17	0.1018	1.2171	0.2827	0.048*
C18	0.1123 (3)	1.29088 (13)	0.1716 (3)	0.0471 (7)
H18	0.0533	1.3161	0.1973	0.057*
C19	0.1709 (3)	1.31292 (12)	0.0819 (2)	0.0416 (7)
C20	0.2618 (3)	1.27543 (13)	0.0469 (3)	0.0455 (7)
H20	0.3039	1.2905	−0.0110	0.055*
C21	0.2892 (2)	1.21626 (12)	0.0979 (2)	0.0406 (7)
H21	0.3491	1.1913	0.0730	0.049*
C22	0.3756 (3)	0.87749 (13)	0.5160 (3)	0.0523 (8)
C23	0.3240 (2)	0.82471 (12)	0.5819 (2)	0.0390 (6)
C24	0.3987 (3)	0.78902 (14)	0.6709 (3)	0.0503 (8)
H24	0.4828	0.7979	0.6909	0.060*
C25	0.3509 (3)	0.74027 (13)	0.7308 (3)	0.0495 (8)
H25	0.4027	0.7164	0.7897	0.059*
C26	0.2253 (3)	0.72726 (12)	0.7024 (2)	0.0393 (6)
C27	0.1495 (3)	0.76263 (13)	0.6135 (3)	0.0450 (7)
H27	0.0653	0.7539	0.5937	0.054*
C28	0.1986 (3)	0.81074 (13)	0.5542 (2)	0.0439 (7)
H28	0.1468	0.8342	0.4946	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Pb1	0.03696 (5)	0.03192 (5)	0.02734 (5)	−0.00627 (4)	0.00379 (4)	−0.00068 (4)
O1	0.0582 (12)	0.0384 (10)	0.0471 (11)	−0.0025 (9)	0.0258 (10)	0.0015 (8)
O2	0.0481 (11)	0.0396 (9)	0.0362 (10)	0.0098 (8)	0.0129 (9)	0.0037 (8)
O3	0.0839 (15)	0.0490 (11)	0.0582 (13)	0.0280 (11)	0.0313 (12)	0.0177 (10)
O4	0.0853 (15)	0.0409 (11)	0.0417 (12)	−0.0202 (10)	0.0037 (11)	0.0067 (9)
O5	0.0940 (18)	0.1016 (19)	0.119 (2)	−0.0676 (16)	−0.0374 (17)	0.0441 (17)
O6	0.0571 (12)	0.0458 (11)	0.0524 (12)	0.0004 (9)	0.0171 (10)	0.0133 (9)
N1	0.0313 (11)	0.0301 (10)	0.0303 (11)	−0.0027 (8)	0.0073 (9)	−0.0012 (8)
N2	0.0334 (11)	0.0411 (12)	0.0372 (12)	0.0016 (9)	0.0088 (10)	−0.0015 (9)
C1	0.0340 (14)	0.0372 (14)	0.0449 (16)	−0.0034 (11)	0.0121 (12)	−0.0010 (11)
C2	0.0318 (15)	0.0667 (19)	0.063 (2)	−0.0111 (14)	0.0100 (14)	−0.0072 (16)
C3	0.0367 (16)	0.068 (2)	0.0544 (19)	−0.0132 (14)	−0.0071 (14)	−0.0123 (16)
C4	0.0445 (16)	0.0451 (15)	0.0353 (15)	−0.0074 (13)	0.0004 (13)	−0.0056 (12)
C5	0.063 (2)	0.0629 (19)	0.0377 (17)	−0.0111 (16)	−0.0027 (15)	−0.0139 (14)
C6	0.076 (2)	0.0606 (19)	0.0351 (16)	−0.0031 (17)	0.0124 (16)	−0.0158 (14)
C7	0.0543 (17)	0.0501 (16)	0.0375 (16)	0.0035 (13)	0.0159 (14)	−0.0070 (12)
C8	0.065 (2)	0.076 (2)	0.057 (2)	0.0112 (18)	0.0280 (17)	−0.0155 (17)
C9	0.0449 (17)	0.095 (3)	0.073 (2)	0.0104 (18)	0.0258 (17)	−0.017 (2)
C10	0.0366 (16)	0.071 (2)	0.057 (2)	0.0050 (15)	0.0116 (14)	−0.0066 (16)
C11	0.0398 (14)	0.0318 (12)	0.0337 (14)	0.0011 (11)	0.0086 (12)	−0.0012 (10)
C12	0.0376 (14)	0.0294 (12)	0.0324 (14)	−0.0006 (10)	0.0052 (11)	−0.0025 (10)
C13	0.0436 (15)	0.0598 (18)	0.0589 (19)	−0.0091 (14)	0.0262 (14)	−0.0120 (14)
C14	0.0338 (18)	0.147 (4)	0.079 (3)	0.002 (2)	0.0060 (18)	−0.025 (3)
C15	0.0351 (14)	0.0349 (13)	0.0299 (14)	−0.0031 (11)	0.0039 (11)	−0.0029 (10)
C16	0.0318 (13)	0.0343 (13)	0.0310 (14)	−0.0007 (10)	0.0041 (11)	−0.0017 (10)
C17	0.0413 (15)	0.0450 (15)	0.0358 (15)	0.0022 (12)	0.0141 (12)	0.0016 (11)
C18	0.0500 (16)	0.0501 (16)	0.0451 (17)	0.0173 (13)	0.0190 (14)	0.0022 (13)
C19	0.0489 (16)	0.0375 (14)	0.0390 (16)	0.0085 (12)	0.0104 (13)	0.0035 (11)
C20	0.0471 (16)	0.0473 (15)	0.0470 (17)	0.0077 (13)	0.0211 (13)	0.0105 (12)
C21	0.0405 (15)	0.0437 (14)	0.0402 (16)	0.0109 (12)	0.0146 (13)	0.0035 (12)
C22	0.061 (2)	0.0396 (15)	0.0538 (19)	−0.0162 (14)	0.0057 (16)	−0.0010 (13)
C23	0.0444 (15)	0.0355 (13)	0.0347 (15)	−0.0069 (12)	0.0020 (12)	−0.0004 (11)
C24	0.0398 (16)	0.0552 (17)	0.0509 (19)	−0.0105 (13)	−0.0027 (14)	0.0063 (14)
C25	0.0502 (17)	0.0466 (16)	0.0474 (18)	0.0056 (13)	−0.0006 (14)	0.0118 (13)
C26	0.0518 (16)	0.0323 (13)	0.0361 (15)	0.0008 (12)	0.0138 (13)	0.0017 (11)
C27	0.0411 (15)	0.0503 (16)	0.0440 (17)	−0.0035 (13)	0.0099 (13)	0.0066 (13)
C28	0.0457 (16)	0.0446 (15)	0.0385 (16)	0.0038 (13)	0.0017 (13)	0.0074 (12)

Geometric parameters (Å, º)

Pb1—N2	2.464 (2)	C8—C9	1.363 (5)
Pb1—N1	2.4818 (19)	C8—H8	0.9300
Pb1—O2	2.4851 (17)	C9—C10	1.394 (4)
Pb1—O4	2.5291 (18)	C9—H9	0.9300
Pb1—O1	2.6298 (18)	C10—C14	1.506 (4)
Pb1—O5^i	2.767 (2)	C11—C12	1.445 (3)
Pb1—C15	2.914 (2)	C13—H13A	0.9600
O1—C15	1.271 (3)	C13—H13B	0.9600
O2—C15	1.254 (3)	C13—H13C	0.9600
O3—C19	1.359 (3)	C14—H14A	0.9600
O3—H3	0.8200	C14—H14B	0.9600
O4—C22	1.269 (3)	C14—H14C	0.9600
O5—C22	1.216 (4)	C15—C16	1.491 (3)
O5—Pb1^i	2.767 (2)	C16—C17	1.389 (3)
O6—C26	1.357 (3)	C16—C21	1.390 (3)
O6—H6	0.8200	C17—C18	1.379 (4)
N1—C1	1.330 (3)	C17—H17	0.9300
N1—C12	1.365 (3)	C18—C19	1.386 (4)
N2—C10	1.329 (3)	C18—H18	0.9300
N2—C11	1.365 (3)	C19—C20	1.393 (4)
C1—C2	1.394 (4)	C20—C21	1.372 (4)
C1—C13	1.499 (4)	C20—H20	0.9300
C2—C3	1.363 (4)	C21—H21	0.9300
C2—H2	0.9300	C22—C23	1.506 (4)
C3—C4	1.405 (4)	C23—C24	1.383 (4)
C3—H3A	0.9300	C23—C28	1.389 (4)
C4—C12	1.409 (3)	C24—C25	1.386 (4)
C4—C5	1.427 (4)	C24—H24	0.9300
C5—C6	1.340 (4)	C25—C26	1.387 (4)
C5—H5	0.9300	C25—H25	0.9300
C6—C7	1.430 (4)	C26—C27	1.385 (4)
C6—H6A	0.9300	C27—C28	1.379 (4)
C7—C11	1.406 (4)	C27—H27	0.9300
C7—C8	1.408 (4)	C28—H28	0.9300
N2—Pb1—N1	67.72 (7)	N2—C11—C7	122.3 (2)
N2—Pb1—O2	75.58 (6)	N2—C11—C12	118.4 (2)
N1—Pb1—O2	80.12 (6)	C7—C11—C12	119.3 (2)
N2—Pb1—O4	82.52 (7)	N1—C12—C4	122.2 (2)
N1—Pb1—O4	72.09 (7)	N1—C12—C11	119.0 (2)
O2—Pb1—O4	149.58 (6)	C4—C12—C11	118.8 (2)
N2—Pb1—O1	121.26 (6)	C1—C13—H13A	109.5
N1—Pb1—O1	79.82 (6)	C1—C13—H13B	109.5
O2—Pb1—O1	50.84 (6)	H13A—C13—H13B	109.5
O4—Pb1—O1	132.21 (7)	C1—C13—H13C	109.5
N2—Pb1—O5^i	109.00 (9)	H13A—C13—H13C	109.5
N1—Pb1—O5^i	155.30 (7)	H13B—C13—H13C	109.5
O2—Pb1—O5^i	75.47 (7)	C10—C14—H14A	109.5
O4—Pb1—O5^i	132.55 (7)	C10—C14—H14B	109.5
O1—Pb1—O5^i	81.89 (8)	H14A—C14—H14B	109.5
N2—Pb1—C15	99.56 (7)	C10—C14—H14C	109.5
N1—Pb1—C15	81.81 (6)	H14A—C14—H14C	109.5
O2—Pb1—C15	25.29 (6)	H14B—C14—H14C	109.5
O4—Pb1—C15	150.90 (7)	O2—C15—O1	121.2 (2)
O1—Pb1—C15	25.87 (6)	O2—C15—C16	119.7 (2)
O5^i—Pb1—C15	74.53 (7)	O1—C15—C16	119.1 (2)
C15—O1—Pb1	89.65 (14)	O2—C15—Pb1	57.86 (12)
C15—O2—Pb1	96.86 (15)	O1—C15—Pb1	64.48 (13)
C19—O3—H3	109.5	C16—C15—Pb1	170.63 (17)
C22—O4—Pb1	114.65 (17)	C17—C16—C21	118.0 (2)
C22—O5—Pb1^i	163.1 (3)	C17—C16—C15	121.2 (2)
C26—O6—H6	109.5	C21—C16—C15	120.8 (2)
C1—N1—C12	119.6 (2)	C18—C17—C16	121.2 (3)
C1—N1—Pb1	123.69 (16)	C18—C17—H17	119.4
C12—N1—Pb1	116.66 (15)	C16—C17—H17	119.4
C10—N2—C11	119.1 (2)	C17—C18—C19	120.0 (3)
C10—N2—Pb1	123.19 (18)	C17—C18—H18	120.0
C11—N2—Pb1	117.42 (16)	C19—C18—H18	120.0
N1—C1—C2	120.8 (3)	O3—C19—C18	118.3 (2)
N1—C1—C13	119.1 (2)	O3—C19—C20	122.4 (3)
C2—C1—C13	120.1 (2)	C18—C19—C20	119.4 (2)
C3—C2—C1	120.5 (3)	C21—C20—C19	119.9 (3)
C3—C2—H2	119.8	C21—C20—H20	120.0
C1—C2—H2	119.8	C19—C20—H20	120.0
C2—C3—C4	120.1 (3)	C20—C21—C16	121.4 (2)
C2—C3—H3A	119.9	C20—C21—H21	119.3
C4—C3—H3A	119.9	C16—C21—H21	119.3
C3—C4—C12	116.6 (3)	O5—C22—O4	122.7 (3)
C3—C4—C5	123.3 (3)	O5—C22—C23	120.3 (3)
C12—C4—C5	120.1 (3)	O4—C22—C23	117.0 (3)
C6—C5—C4	120.9 (3)	C24—C23—C28	118.2 (2)
C6—C5—H5	119.5	C24—C23—C22	121.6 (3)
C4—C5—H5	119.5	C28—C23—C22	120.2 (2)
C5—C6—C7	121.1 (3)	C23—C24—C25	121.4 (3)
C5—C6—H6A	119.4	C23—C24—H24	119.3
C7—C6—H6A	119.4	C25—C24—H24	119.3
C11—C7—C8	117.2 (3)	C24—C25—C26	119.6 (3)
C11—C7—C6	119.7 (3)	C24—C25—H25	120.2
C8—C7—C6	123.0 (3)	C26—C25—H25	120.2
C9—C8—C7	119.2 (3)	O6—C26—C27	117.0 (2)
C9—C8—H8	120.4	O6—C26—C25	123.4 (2)
C7—C8—H8	120.4	C27—C26—C25	119.6 (2)
C8—C9—C10	120.8 (3)	C28—C27—C26	120.1 (3)
C8—C9—H9	119.6	C28—C27—H27	119.9
C10—C9—H9	119.6	C26—C27—H27	119.9
N2—C10—C9	121.2 (3)	C27—C28—C23	121.1 (3)
N2—C10—C14	117.2 (3)	C27—C28—H28	119.4
C9—C10—C14	121.5 (3)	C23—C28—H28	119.4
N2—Pb1—O1—C15	−36.24 (16)	C10—N2—C11—C12	176.3 (2)
N1—Pb1—O1—C15	−92.21 (15)	Pb1—N2—C11—C12	−9.2 (3)
O2—Pb1—O1—C15	−6.72 (13)	C8—C7—C11—N2	−2.4 (4)
O4—Pb1—O1—C15	−146.43 (14)	C6—C7—C11—N2	177.3 (3)
O5^i—Pb1—O1—C15	71.10 (16)	C8—C7—C11—C12	−179.2 (3)
N2—Pb1—O2—C15	161.08 (16)	C6—C7—C11—C12	0.5 (4)
N1—Pb1—O2—C15	91.73 (15)	C1—N1—C12—C4	3.7 (4)
O4—Pb1—O2—C15	115.79 (18)	Pb1—N1—C12—C4	−177.46 (19)
O1—Pb1—O2—C15	6.86 (14)	C1—N1—C12—C11	−173.9 (2)
O5^i—Pb1—O2—C15	−84.47 (16)	Pb1—N1—C12—C11	4.9 (3)
N2—Pb1—O4—C22	122.6 (2)	C3—C4—C12—N1	−2.0 (4)
N1—Pb1—O4—C22	−168.4 (2)	C5—C4—C12—N1	179.3 (2)
O2—Pb1—O4—C22	166.60 (19)	C3—C4—C12—C11	175.6 (2)
O1—Pb1—O4—C22	−111.4 (2)	C5—C4—C12—C11	−3.1 (4)
O5^i—Pb1—O4—C22	13.7 (3)	N2—C11—C12—N1	2.8 (3)
C15—Pb1—O4—C22	−141.1 (2)	C7—C11—C12—N1	179.8 (2)
N2—Pb1—N1—C1	172.1 (2)	N2—C11—C12—C4	−174.9 (2)
O2—Pb1—N1—C1	−109.56 (19)	C7—C11—C12—C4	2.1 (4)
O4—Pb1—N1—C1	82.97 (19)	Pb1—O2—C15—O1	−12.9 (3)
O1—Pb1—N1—C1	−57.88 (19)	Pb1—O2—C15—C16	169.45 (19)
O5^i—Pb1—N1—C1	−100.7 (3)	Pb1—O1—C15—O2	12.1 (2)
C15—Pb1—N1—C1	−84.01 (19)	Pb1—O1—C15—C16	−170.2 (2)
N2—Pb1—N1—C12	−6.72 (15)	N2—Pb1—C15—O2	−18.57 (15)
O2—Pb1—N1—C12	71.63 (16)	N1—Pb1—C15—O2	−84.19 (15)
O4—Pb1—N1—C12	−95.83 (17)	O4—Pb1—C15—O2	−110.36 (18)
O1—Pb1—N1—C12	123.32 (17)	O1—Pb1—C15—O2	−167.7 (2)
O5^i—Pb1—N1—C12	80.5 (3)	O5^i—Pb1—C15—O2	88.64 (16)
C15—Pb1—N1—C12	97.19 (17)	N2—Pb1—C15—O1	149.17 (14)
N1—Pb1—N2—C10	−177.5 (2)	N1—Pb1—C15—O1	83.54 (14)
O2—Pb1—N2—C10	97.4 (2)	O2—Pb1—C15—O1	167.7 (2)
O4—Pb1—N2—C10	−103.9 (2)	O4—Pb1—C15—O1	57.4 (2)
O1—Pb1—N2—C10	120.7 (2)	O5^i—Pb1—C15—O1	−103.62 (16)
O5^i—Pb1—N2—C10	28.7 (2)	O2—C15—C16—C17	171.0 (2)
C15—Pb1—N2—C10	105.5 (2)	O1—C15—C16—C17	−6.7 (4)
N1—Pb1—N2—C11	8.24 (16)	O2—C15—C16—C21	−7.0 (4)
O2—Pb1—N2—C11	−76.82 (17)	O1—C15—C16—C21	175.3 (2)
O4—Pb1—N2—C11	81.90 (18)	C21—C16—C17—C18	1.5 (4)
O1—Pb1—N2—C11	−53.58 (19)	C15—C16—C17—C18	−176.6 (2)
O5^i—Pb1—N2—C11	−145.56 (17)	C16—C17—C18—C19	0.0 (4)
C15—Pb1—N2—C11	−68.75 (18)	C17—C18—C19—O3	177.7 (3)
C12—N1—C1—C2	−2.5 (4)	C17—C18—C19—C20	−1.9 (4)
Pb1—N1—C1—C2	178.8 (2)	O3—C19—C20—C21	−177.2 (3)
C12—N1—C1—C13	176.0 (2)	C18—C19—C20—C21	2.4 (4)
Pb1—N1—C1—C13	−2.7 (3)	C19—C20—C21—C16	−1.0 (4)
N1—C1—C2—C3	−0.3 (4)	C17—C16—C21—C20	−0.9 (4)
C13—C1—C2—C3	−178.8 (3)	C15—C16—C21—C20	177.1 (2)
C1—C2—C3—C4	2.0 (5)	Pb1^i—O5—C22—O4	52.9 (11)
C2—C3—C4—C12	−0.8 (4)	Pb1^i—O5—C22—C23	−127.0 (8)
C2—C3—C4—C5	177.8 (3)	Pb1—O4—C22—O5	−25.3 (4)
C3—C4—C5—C6	−177.1 (3)	Pb1—O4—C22—C23	154.6 (2)
C12—C4—C5—C6	1.4 (5)	O5—C22—C23—C24	−22.2 (5)
C4—C5—C6—C7	1.3 (5)	O4—C22—C23—C24	157.9 (3)
C5—C6—C7—C11	−2.2 (5)	O5—C22—C23—C28	157.7 (3)
C5—C6—C7—C8	177.5 (3)	O4—C22—C23—C28	−22.2 (4)
C11—C7—C8—C9	3.5 (5)	C28—C23—C24—C25	0.4 (4)
C6—C7—C8—C9	−176.2 (3)	C22—C23—C24—C25	−179.6 (3)
C7—C8—C9—C10	−1.9 (5)	C23—C24—C25—C26	−0.8 (5)
C11—N2—C10—C9	2.4 (4)	C24—C25—C26—O6	−179.7 (3)
Pb1—N2—C10—C9	−171.7 (2)	C24—C25—C26—C27	0.8 (4)
C11—N2—C10—C14	−177.0 (3)	O6—C26—C27—C28	−179.9 (3)
Pb1—N2—C10—C14	8.9 (4)	C25—C26—C27—C28	−0.4 (4)
C8—C9—C10—N2	−1.2 (5)	C26—C27—C28—C23	0.0 (4)
C8—C9—C10—C14	178.2 (4)	C24—C23—C28—C27	0.0 (4)
C10—N2—C11—C7	−0.6 (4)	C22—C23—C28—C27	−180.0 (3)
Pb1—N2—C11—C7	173.90 (19)

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O1^ii	0.82	1.84	2.652 (3)	172
O6—H6···O4^iii	0.82	1.82	2.619 (3)	165

Symmetry codes: (ii) x, −y+5/2, z−1/2; (iii) x, −y+3/2, z+1/2.