catena-Poly[[[bis-(4-ethyl-benzoato-κO,O')lead(II)]-μ-nicotinamide-κN:O] monohydrate].

In the crystal structure of the polymeric title compound, {[Pb(C(9)H(9)O(2))(2)(C(6)H(6)N(2)O)]·H(2)O}(n), the six-coordinate Pb(II) ion is chelated by two 4-ethyl-benzoate (PEB) anions and is bridged by two nicotinamide (NA) ligands, forming a polymeric chain running along the b axis. The carboxyl-ate groups of the PEB ions are twisted away from the attached benzene rings by 4.0 (6) and 13.3 (5)°. The two benzene rings of the PEB ions bonded to the same metal ion are oriented at a dihedral angle of 87.4 (3)°. In the polymeric chain, the NA ligand is linked to one of the carboxyl-ate groups via N-H⋯O hydrogen bonding. In the crystal, adjacent polymeric chains inter-act via N-H⋯O and weak C-H⋯O hydrogen bonds; and the lattice water mol-ecule links with the polymeric chains via N-H⋯O and O-H⋯O hydrogen bonding. π-π stacking between the benzene and the pyridine rings [centroid-centroid distance = 3.805 (5) Å] and weak C-H⋯π inter-actions are also observed in the crystal structure.

Related literature

For niacin, see: Krishnamachari (1974 ▶). For N,N-diethyl­nicotinamide, see: Bigoli et al. (1972 ▶). For related structures, see: Greenaway et al. (1984 ▶); Hökelek & Necefoğlu (1996 ▶); Hökelek et al. (2009a ▶,b ▶,c ▶,d ▶, 2010 ▶).

Experimental

Crystal data

[Pb(C9H9O2)2(C6H6N2O)]·H2O

M = 645.67

Triclinic,

a = 7.8093 (2) Å

b = 9.7950 (3) Å

c = 16.9380 (5) Å

α = 90.772 (2)°

β = 91.256 (2)°

γ = 106.916 (4)°

V = 1239.00 (7) Å3

Z = 2

Mo Kα radiation

μ = 6.85 mm−1

T = 294 K

0.25 × 0.20 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.211, T max = 0.358

26925 measured reflections

5076 independent reflections

4208 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.099

S = 1.06

5076 reflections

314 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.11 e Å−3

Δρmin = −0.96 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026535/xu5254sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026535/xu5254Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Pb(C9H9O2)2(C6H6N2O)]·H2O	Z = 2
Mr = 645.67	F(000) = 628
Triclinic, P1	Dx = 1.731 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.8093 (2) Å	Cell parameters from 6051 reflections
b = 9.7950 (3) Å	θ = 2.2–26.4°
c = 16.9380 (5) Å	µ = 6.85 mm−1
α = 90.772 (2)°	T = 294 K
β = 91.256 (2)°	Block, colorless
γ = 106.916 (4)°	0.25 × 0.20 × 0.15 mm
V = 1239.00 (7) Å3

Rigaku R-AXIS RAPID-S diffractometer	5076 independent reflections
Radiation source: fine-focus sealed tube	4208 reflections with I > 2σ(I)
graphite	Rint = 0.081
ω scans	θmax = 26.4°, θmin = 2.2°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→9
Tmin = 0.211, Tmax = 0.358	k = −12→10
26925 measured reflections	l = −21→21

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0277P)2 + 1.8361P] where P = (Fo2 + 2Fc2)/3
5076 reflections	(Δ/σ)max < 0.001
314 parameters	Δρmax = 1.11 e Å−3
5 restraints	Δρmin = −0.96 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
Pb1	0.08609 (4)	0.15890 (3)	0.394120 (15)	0.05863 (12)
O1	0.2512 (8)	0.2967 (5)	0.5057 (3)	0.0772 (15)
O2	0.2289 (7)	0.0686 (5)	0.5205 (3)	0.0700 (13)
O3	0.3813 (6)	0.2084 (5)	0.3496 (3)	0.0666 (12)
O4	0.1966 (7)	0.1944 (5)	0.2477 (3)	0.0664 (12)
O5	0.0783 (8)	0.4092 (5)	0.3616 (3)	0.0789 (15)
O6	0.3512 (9)	0.8292 (6)	0.5453 (4)	0.0839 (17)
H61	0.347 (11)	0.919 (4)	0.550 (5)	0.09 (3)*
H62	0.425 (11)	0.808 (11)	0.582 (5)	0.14 (4)*
N1	0.0879 (8)	−0.1057 (6)	0.3322 (3)	0.0626 (15)
N2	0.2113 (10)	0.5633 (7)	0.4600 (4)	0.0671 (17)
H2A	0.24 (2)	0.509 (17)	0.482 (10)	0.211*
H2B	0.26 (2)	0.640 (16)	0.482 (9)	0.211*
C1	0.2776 (9)	0.1960 (8)	0.5468 (4)	0.0588 (17)
C2	0.3632 (9)	0.2337 (7)	0.6261 (4)	0.0572 (16)
C3	0.3884 (10)	0.1280 (8)	0.6761 (4)	0.0676 (19)
H3	0.3562	0.0336	0.6581	0.081*
C4	0.4593 (11)	0.1614 (8)	0.7507 (4)	0.072 (2)
H4	0.4733	0.0893	0.7832	0.087*
C5	0.5101 (11)	0.2995 (9)	0.7782 (5)	0.075 (2)
C6	0.4914 (12)	0.4041 (9)	0.7300 (5)	0.086 (3)
H6	0.5287	0.4983	0.7483	0.103*
C7	0.4179 (10)	0.3741 (7)	0.6538 (4)	0.0678 (19)
H7	0.4055	0.4473	0.6219	0.081*
C8	0.5923 (15)	0.3367 (12)	0.8615 (6)	0.114 (4)
H8A	0.6335	0.2584	0.8804	0.137*
H8B	0.6954	0.4205	0.8593	0.137*
C9	0.465 (2)	0.364 (2)	0.9167 (8)	0.226 (10)
H9A	0.5276	0.4072	0.9644	0.339*
H9B	0.3777	0.2761	0.9287	0.339*
H9C	0.4062	0.4280	0.8934	0.339*
C10	0.3483 (10)	0.2031 (7)	0.2747 (4)	0.0613 (17)
C11	0.4949 (9)	0.2061 (7)	0.2208 (4)	0.0578 (16)
C12	0.6732 (10)	0.2396 (8)	0.2472 (4)	0.0664 (19)
H12	0.7031	0.2632	0.3001	0.080*
C13	0.8050 (11)	0.2375 (9)	0.1947 (5)	0.077 (2)
H13	0.9236	0.2624	0.2128	0.092*
C14	0.7663 (13)	0.1999 (12)	0.1170 (6)	0.094 (3)
C15	0.5895 (13)	0.1637 (11)	0.0916 (5)	0.095 (3)
H15	0.5603	0.1349	0.0392	0.114*
C16	0.4540 (11)	0.1691 (9)	0.1423 (5)	0.078 (2)
H16	0.3363	0.1479	0.1234	0.094*
C17	0.9025 (19)	0.166 (2)	0.0606 (8)	0.193 (9)
H17A	0.9823	0.1221	0.0880	0.289*
H17B	0.8430	0.1051	0.0166	0.289*
C18	0.997 (3)	0.309 (3)	0.0350 (13)	0.328 (18)
H18A	1.0379	0.3035	−0.0177	0.491*
H18B	1.0975	0.3498	0.0700	0.491*
H18C	0.9172	0.3673	0.0356	0.491*
C19	0.1215 (9)	−0.2116 (7)	0.3749 (4)	0.0593 (17)
H19	0.1658	−0.1909	0.4264	0.071*
C20	0.0926 (9)	0.6504 (7)	0.3452 (4)	0.0573 (16)
C21	0.0247 (11)	0.6222 (8)	0.2695 (4)	0.071 (2)
H21	0.0012	0.5307	0.2478	0.086*
C22	−0.0087 (12)	−0.2704 (8)	0.2257 (5)	0.079 (2)
H22	−0.0530	−0.2880	0.1740	0.094*
C23	0.0241 (10)	−0.1386 (8)	0.2593 (4)	0.0654 (19)
H23	0.0003	−0.0671	0.2293	0.079*
C24	0.1279 (9)	0.5335 (7)	0.3905 (4)	0.0567 (16)

	U11	U22	U33	U12	U13	U23
Pb1	0.0721 (2)	0.04518 (17)	0.05984 (18)	0.01901 (13)	−0.00048 (12)	0.00349 (11)
O1	0.113 (4)	0.062 (3)	0.062 (3)	0.034 (3)	−0.010 (3)	0.005 (2)
O2	0.093 (4)	0.055 (3)	0.063 (3)	0.025 (3)	−0.010 (3)	−0.001 (2)
O3	0.069 (3)	0.068 (3)	0.063 (3)	0.020 (3)	−0.006 (2)	0.003 (2)
O4	0.065 (3)	0.069 (3)	0.068 (3)	0.024 (2)	−0.005 (2)	0.011 (2)
O5	0.113 (4)	0.040 (3)	0.083 (4)	0.023 (3)	−0.015 (3)	0.003 (2)
O6	0.110 (5)	0.062 (4)	0.088 (4)	0.043 (3)	−0.043 (3)	−0.020 (3)
N1	0.081 (4)	0.046 (3)	0.062 (4)	0.022 (3)	−0.012 (3)	−0.001 (3)
N2	0.080 (4)	0.054 (4)	0.067 (4)	0.019 (3)	−0.006 (3)	0.000 (3)
C1	0.065 (4)	0.053 (4)	0.058 (4)	0.017 (3)	0.001 (3)	0.006 (3)
C2	0.074 (5)	0.044 (4)	0.056 (4)	0.020 (3)	0.007 (3)	0.009 (3)
C3	0.079 (5)	0.065 (5)	0.061 (4)	0.025 (4)	−0.006 (4)	−0.003 (4)
C4	0.099 (6)	0.059 (5)	0.065 (5)	0.032 (4)	−0.010 (4)	0.011 (4)
C5	0.095 (6)	0.063 (5)	0.070 (5)	0.030 (4)	−0.018 (4)	−0.004 (4)
C6	0.106 (7)	0.053 (5)	0.090 (6)	0.012 (4)	−0.004 (5)	−0.018 (4)
C7	0.092 (6)	0.044 (4)	0.066 (5)	0.019 (4)	−0.007 (4)	0.007 (3)
C8	0.139 (10)	0.119 (9)	0.085 (7)	0.042 (7)	−0.032 (6)	−0.025 (6)
C9	0.30 (2)	0.36 (3)	0.091 (10)	0.21 (2)	−0.035 (12)	−0.051 (13)
C10	0.067 (5)	0.052 (4)	0.064 (5)	0.016 (3)	−0.006 (4)	−0.001 (3)
C11	0.064 (4)	0.056 (4)	0.053 (4)	0.018 (3)	−0.007 (3)	−0.002 (3)
C12	0.074 (5)	0.064 (5)	0.063 (4)	0.022 (4)	−0.005 (4)	0.001 (3)
C13	0.062 (5)	0.094 (6)	0.079 (6)	0.031 (4)	−0.002 (4)	0.000 (4)
C14	0.079 (6)	0.126 (8)	0.086 (6)	0.042 (6)	0.008 (5)	0.000 (6)
C15	0.088 (7)	0.148 (9)	0.057 (5)	0.046 (6)	−0.003 (4)	−0.004 (5)
C16	0.069 (5)	0.099 (6)	0.070 (5)	0.030 (5)	−0.009 (4)	0.009 (4)
C17	0.106 (11)	0.36 (3)	0.114 (11)	0.072 (14)	0.043 (8)	0.046 (13)
C18	0.21 (3)	0.60 (6)	0.19 (2)	0.14 (3)	0.084 (18)	0.05 (3)
C19	0.066 (4)	0.047 (4)	0.066 (4)	0.020 (3)	−0.007 (3)	−0.006 (3)
C20	0.062 (4)	0.048 (4)	0.062 (4)	0.016 (3)	0.005 (3)	−0.001 (3)
C21	0.101 (6)	0.048 (4)	0.067 (5)	0.025 (4)	−0.012 (4)	−0.007 (3)
C22	0.111 (7)	0.060 (5)	0.063 (5)	0.024 (4)	−0.022 (4)	−0.004 (4)
C23	0.078 (5)	0.056 (4)	0.065 (5)	0.025 (4)	−0.008 (4)	0.008 (3)
C24	0.070 (5)	0.034 (4)	0.065 (4)	0.014 (3)	0.000 (3)	0.010 (3)

Pb1—O1	2.423 (5)	C9—H9A	0.9600
Pb1—O2	2.670 (5)	C9—H9B	0.9600
Pb1—O3	2.356 (5)	C9—H9C	0.9600
Pb1—O4	2.638 (5)	C11—C10	1.474 (10)
Pb1—O5	2.537 (5)	C11—C12	1.397 (10)
Pb1—N1	2.787 (5)	C11—C16	1.379 (10)
Pb1—C1	2.924 (7)	C12—C13	1.378 (10)
Pb1—C10	2.856 (8)	C12—H12	0.9300
O1—C1	1.277 (8)	C13—C14	1.365 (12)
O2—C1	1.266 (8)	C13—H13	0.9300
O3—C10	1.286 (8)	C14—C15	1.379 (12)
O4—C10	1.240 (8)	C15—H15	0.9300
O5—C24	1.254 (8)	C16—C15	1.390 (11)
O6—H61	0.89 (2)	C16—H16	0.9300
O6—H62	0.90 (2)	C17—C18	1.454 (17)
N1—C19	1.356 (8)	C17—C14	1.547 (12)
N1—C23	1.320 (8)	C17—H17A	0.9700
N2—H2A	0.72 (15)	C17—H17B	0.9700
N2—H2B	0.82 (15)	C18—H18A	0.9600
C1—C2	1.479 (9)	C18—H18B	0.9600
C2—C3	1.400 (9)	C18—H18C	0.9600
C2—C7	1.388 (9)	C19—C20i	1.389 (9)
C3—C4	1.366 (10)	C19—H19	0.9300
C3—H3	0.9300	C20—C21	1.369 (10)
C4—C5	1.367 (10)	C20—C19ii	1.389 (9)
C4—H4	0.9300	C21—C22ii	1.377 (10)
C5—C6	1.358 (11)	C21—H21	0.9300
C5—C8	1.530 (11)	C22—C21i	1.377 (10)
C6—H6	0.9300	C22—H22	0.9300
C7—C6	1.393 (11)	C23—C22	1.356 (10)
C7—H7	0.9300	C23—H23	0.9300
C8—H8A	0.9700	C24—N2	1.320 (9)
C8—H8B	0.9700	C24—C20	1.474 (9)
C9—C8	1.458 (13)
O1—Pb1—O2	51.10 (15)	C5—C8—H8B	109.2
O1—Pb1—O4	123.27 (17)	C9—C8—C5	112.2 (10)
O1—Pb1—O5	78.18 (17)	C9—C8—H8A	109.2
O1—Pb1—N1	130.47 (17)	C9—C8—H8B	109.2
O1—Pb1—C1	25.49 (17)	H8A—C8—H8B	107.9
O1—Pb1—C10	103.1 (2)	C8—C9—H9A	109.5
O2—Pb1—N1	82.33 (16)	C8—C9—H9B	109.5
O2—Pb1—C1	25.64 (16)	C8—C9—H9C	109.5
O2—Pb1—C10	106.17 (19)	H9A—C9—H9B	109.5
O3—Pb1—O1	79.48 (18)	H9A—C9—H9C	109.5
O3—Pb1—O2	82.21 (16)	H9B—C9—H9C	109.5
O3—Pb1—O4	51.95 (16)	O3—C10—Pb1	54.6 (4)
O3—Pb1—O5	91.12 (18)	O3—C10—C11	118.7 (6)
O3—Pb1—N1	78.26 (17)	O4—C10—Pb1	67.3 (4)
O3—Pb1—C1	80.81 (18)	O4—C10—O3	121.3 (7)
O3—Pb1—C10	26.41 (18)	O4—C10—C11	120.0 (7)
O4—Pb1—O2	130.39 (15)	C11—C10—Pb1	169.6 (5)
O4—Pb1—N1	71.75 (16)	C12—C11—C10	122.1 (6)
O4—Pb1—C1	132.48 (17)	C16—C11—C10	119.0 (7)
O4—Pb1—C10	25.69 (17)	C16—C11—C12	118.8 (7)
O5—Pb1—O2	129.25 (16)	C11—C12—H12	120.0
O5—Pb1—O4	75.76 (16)	C13—C12—C11	119.9 (7)
O5—Pb1—N1	145.37 (17)	C13—C12—H12	120.0
O5—Pb1—C1	103.61 (18)	C12—C13—H13	119.1
O5—Pb1—C10	84.56 (19)	C14—C13—C12	121.9 (8)
N1—Pb1—C1	106.98 (18)	C14—C13—H13	119.1
N1—Pb1—C10	71.28 (19)	C13—C14—C15	118.0 (8)
C10—Pb1—C1	107.2 (2)	C13—C14—C17	123.2 (10)
C1—O1—Pb1	99.8 (4)	C15—C14—C17	117.5 (10)
C1—O2—Pb1	88.4 (4)	C14—C15—C16	121.6 (8)
C10—O3—Pb1	99.0 (4)	C14—C15—H15	119.2
C10—O4—Pb1	87.0 (4)	C16—C15—H15	119.2
C24—O5—Pb1	140.0 (5)	C11—C16—C15	119.7 (8)
H61—O6—H62	113 (9)	C11—C16—H16	120.2
C19—N1—Pb1	124.7 (4)	C15—C16—H16	120.2
C23—N1—Pb1	117.3 (4)	C14—C17—H17A	111.6
C23—N1—C19	117.0 (6)	C14—C17—H17B	111.6
C24—N2—H2A	121 (10)	C18—C17—C14	100.7 (15)
C24—N2—H2B	131 (10)	C18—C17—H17A	111.6
H2B—N2—H2A	107 (10)	C18—C17—H17B	111.6
O1—C1—Pb1	54.8 (3)	H17A—C17—H17B	109.4
O1—C1—C2	117.6 (6)	C17—C18—H18A	109.5
O2—C1—Pb1	65.9 (4)	C17—C18—H18B	109.5
O2—C1—O1	120.6 (6)	C17—C18—H18C	109.5
O2—C1—C2	121.8 (6)	H18A—C18—H18B	109.5
C2—C1—Pb1	171.1 (5)	H18A—C18—H18C	109.5
C3—C2—C1	120.9 (6)	H18B—C18—H18C	109.5
C7—C2—C1	121.2 (6)	N1—C19—C20i	123.0 (6)
C7—C2—C3	117.9 (6)	N1—C19—H19	118.5
C2—C3—H3	119.4	C20i—C19—H19	118.5
C4—C3—C2	121.1 (7)	C19ii—C20—C24	124.0 (6)
C4—C3—H3	119.4	C21—C20—C19ii	117.3 (6)
C3—C4—C5	120.7 (7)	C21—C20—C24	118.6 (6)
C3—C4—H4	119.7	C20—C21—C22ii	119.9 (7)
C5—C4—H4	119.7	C20—C21—H21	120.1
C4—C5—C8	120.5 (8)	C22ii—C21—H21	120.1
C6—C5—C4	119.2 (7)	C21i—C22—H22	120.6
C6—C5—C8	120.3 (8)	C23—C22—C21i	118.8 (7)
C5—C6—C7	121.8 (7)	C23—C22—H22	120.6
C5—C6—H6	119.1	N1—C23—C22	123.9 (7)
C7—C6—H6	119.1	N1—C23—H23	118.1
C2—C7—C6	119.3 (7)	C22—C23—H23	118.1
C2—C7—H7	120.4	O5—C24—N2	122.2 (6)
C6—C7—H7	120.4	O5—C24—C20	119.0 (6)
C5—C8—H8A	109.2	N2—C24—C20	118.9 (6)
O2—Pb1—O1—C1	−2.2 (4)	O4—Pb1—C10—C11	−136 (3)
O3—Pb1—O1—C1	−90.7 (5)	O5—Pb1—C10—O3	103.7 (4)
O4—Pb1—O1—C1	−120.0 (4)	O5—Pb1—C10—O4	−68.2 (4)
O5—Pb1—O1—C1	175.9 (5)	O5—Pb1—C10—C11	156 (3)
N1—Pb1—O1—C1	−26.2 (5)	N1—Pb1—C10—O3	−101.5 (4)
C10—Pb1—O1—C1	−102.6 (5)	N1—Pb1—C10—O4	86.7 (4)
O1—Pb1—O2—C1	2.2 (4)	N1—Pb1—C10—C11	−49 (3)
O3—Pb1—O2—C1	85.0 (4)	C1—Pb1—C10—O3	1.1 (4)
O4—Pb1—O2—C1	106.1 (4)	C1—Pb1—C10—O4	−170.8 (4)
O5—Pb1—O2—C1	−0.1 (5)	C1—Pb1—C10—C11	53 (3)
N1—Pb1—O2—C1	164.1 (4)	Pb1—O1—C1—O2	4.3 (8)
C10—Pb1—O2—C1	96.2 (4)	Pb1—O1—C1—C2	−174.6 (5)
O1—Pb1—O3—C10	−153.1 (4)	Pb1—O2—C1—O1	−3.8 (7)
O2—Pb1—O3—C10	155.1 (4)	Pb1—O2—C1—C2	175.0 (6)
O4—Pb1—O3—C10	−4.5 (4)	Pb1—O3—C10—O4	8.8 (7)
O5—Pb1—O3—C10	−75.4 (4)	Pb1—O3—C10—C11	−170.6 (5)
N1—Pb1—O3—C10	71.4 (4)	Pb1—O4—C10—O3	−7.8 (6)
C1—Pb1—O3—C10	−179.0 (4)	Pb1—O4—C10—C11	171.6 (6)
O1—Pb1—O4—C10	42.4 (5)	Pb1—O5—C24—N2	−1.0 (13)
O2—Pb1—O4—C10	−22.3 (5)	Pb1—O5—C24—C20	178.7 (5)
O3—Pb1—O4—C10	4.6 (4)	Pb1—N1—C19—C20i	169.0 (5)
O5—Pb1—O4—C10	107.6 (4)	C23—N1—C19—C20i	0.4 (11)
N1—Pb1—O4—C10	−84.6 (4)	Pb1—N1—C23—C22	−169.6 (6)
C1—Pb1—O4—C10	12.0 (5)	C19—N1—C23—C22	−0.1 (12)
O1—Pb1—O5—C24	−2.5 (8)	O1—C1—C2—C3	176.8 (7)
O2—Pb1—O5—C24	−0.7 (9)	O1—C1—C2—C7	−1.9 (11)
O3—Pb1—O5—C24	−81.5 (8)	O2—C1—C2—C3	−2.1 (11)
O4—Pb1—O5—C24	−131.7 (8)	O2—C1—C2—C7	179.2 (7)
N1—Pb1—O5—C24	−152.3 (7)	C1—C2—C3—C4	−176.8 (7)
C1—Pb1—O5—C24	−0.7 (8)	C7—C2—C3—C4	2.0 (11)
C10—Pb1—O5—C24	−107.2 (8)	C1—C2—C7—C6	177.4 (7)
O1—Pb1—N1—C19	29.5 (7)	C3—C2—C7—C6	−1.3 (11)
O1—Pb1—N1—C23	−161.8 (5)	C2—C3—C4—C5	−0.9 (13)
O2—Pb1—N1—C19	10.9 (5)	C3—C4—C5—C6	−0.9 (14)
O2—Pb1—N1—C23	179.6 (6)	C3—C4—C5—C8	−179.0 (9)
O3—Pb1—N1—C19	94.5 (6)	C4—C5—C6—C7	1.6 (14)
O3—Pb1—N1—C23	−96.8 (5)	C8—C5—C6—C7	179.7 (9)
O4—Pb1—N1—C19	148.1 (6)	C4—C5—C8—C9	−103.5 (14)
O4—Pb1—N1—C23	−43.3 (5)	C6—C5—C8—C9	78.5 (15)
O5—Pb1—N1—C19	169.1 (5)	C2—C7—C6—C5	−0.5 (13)
O5—Pb1—N1—C23	−22.2 (7)	C12—C11—C10—Pb1	−59 (3)
C1—Pb1—N1—C19	18.1 (6)	C12—C11—C10—O3	−11.5 (10)
C1—Pb1—N1—C23	−173.3 (5)	C12—C11—C10—O4	169.0 (7)
C10—Pb1—N1—C19	121.0 (6)	C16—C11—C10—Pb1	119 (3)
C10—Pb1—N1—C23	−70.4 (5)	C16—C11—C10—O3	165.8 (7)
O1—Pb1—C1—O2	−176.0 (7)	C16—C11—C10—O4	−13.6 (10)
O2—Pb1—C1—O1	176.0 (7)	C16—C11—C12—C13	1.1 (11)
O3—Pb1—C1—O1	84.8 (5)	C10—C11—C12—C13	178.4 (7)
O3—Pb1—C1—O2	−91.1 (4)	C12—C11—C16—C15	1.0 (12)
O4—Pb1—C1—O1	78.9 (5)	C10—C11—C16—C15	−176.4 (8)
O4—Pb1—C1—O2	−97.0 (4)	C11—C12—C13—C14	−1.6 (13)
O5—Pb1—C1—O1	−4.1 (5)	C12—C13—C14—C15	0.1 (15)
O5—Pb1—C1—O2	179.9 (4)	C12—C13—C14—C17	−167.0 (11)
N1—Pb1—C1—O1	159.5 (4)	C13—C14—C15—C16	2.0 (16)
N1—Pb1—C1—O2	−16.5 (4)	C17—C14—C15—C16	169.9 (11)
C10—Pb1—C1—O1	84.3 (5)	C11—C16—C15—C14	−2.6 (15)
C10—Pb1—C1—O2	−91.6 (4)	C18—C17—C14—C13	−85.6 (17)
O1—Pb1—C10—O3	27.2 (4)	C18—C17—C14—C15	107.2 (17)
O1—Pb1—C10—O4	−144.7 (4)	C19ii—C20—C21—C22ii	1.3 (12)
O1—Pb1—C10—C11	79 (3)	C24—C20—C21—C22ii	−179.7 (7)
O2—Pb1—C10—O3	−25.7 (4)	N1—C23—C22—C21i	0.4 (13)
O2—Pb1—C10—O4	162.5 (4)	O5—C24—C20—C19ii	171.9 (7)
O2—Pb1—C10—C11	26 (3)	O5—C24—C20—C21	−7.1 (10)
O3—Pb1—C10—O4	−171.8 (7)	N2—C24—C20—C19ii	−8.4 (11)
O3—Pb1—C10—C11	52 (3)	N2—C24—C20—C21	172.7 (7)
O4—Pb1—C10—O3	171.8 (7)

Cg is the centroid of the C11–C16 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O1	0.74 (17)	2.15 (16)	2.834 (8)	155 (19)
N2—H2B···O6	0.82 (16)	2.06 (15)	2.871 (9)	172 (15)
O6—H61···O2ii	0.89 (5)	2.01 (7)	2.811 (8)	149 (7)
O6—H62···O3iii	0.90 (9)	1.93 (9)	2.822 (9)	169 (10)
C13—H13···O4iv	0.93	2.47	3.313 (11)	150
C19—H19···O6i	0.93	2.43	3.323 (10)	162
C4—H4···Cgv	0.93	2.87	3.712 (8)	151

Table 1

Selected bond lengths (Å)

Pb1—O1	2.423 (5)
Pb1—O2	2.670 (5)
Pb1—O3	2.356 (5)
Pb1—O4	2.638 (5)
Pb1—O5	2.537 (5)
Pb1—N1	2.787 (5)

Table 2

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O1	0.74 (17)	2.15 (16)	2.834 (8)	155 (19)
N2—H2B⋯O6	0.82 (16)	2.06 (15)	2.871 (9)	172 (15)
O6—H61⋯O2i	0.89 (5)	2.01 (7)	2.811 (8)	149 (7)
O6—H62⋯O3ii	0.90 (9)	1.93 (9)	2.822 (9)	169 (10)
C13—H13⋯O4iii	0.93	2.47	3.313 (11)	150
C19—H19⋯O6iv	0.93	2.43	3.323 (10)	162
C4—H4⋯Cgv	0.93	2.87	3.712 (8)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .