catena-Poly[[lead(II)-μ-N'-[1-(pyridin-2-yl-κN)ethyl-idene]isonicotino-hydrazidato-κN',O:N] perchlorate].

The Pb(II) atom in the polymeric title compound, {[Pb(C(13)H(11)N(4)O)]ClO(4)}(n), is coordinated by the N'-[1-(pyridin-2-yl-κN)ethyl-idene]isonicotinohydrazidate ligand via its O,N,N'-donors and simultaneously bridged by a neighbouring ligand via the pyridin-2-yl N atom. The resultant supra-molecular chain is a zigzag along the a axis. The stereochemistry of the Pb(II) atom is defined by an N(3)OE donor set (E = lone pair of electrons), which results in a Ψ-trigonal-bipyramidal coordination with the O and pyridin-2-yl N atoms in axial positions. The dihedral angle between the pyridine rings of the ligand is 6.3 (3)°. The supra-molecular cationic chains are linked into a three-dimensional array via secondary Pb⋯O [3.133 (6) and 3.28 (7) Å] and Pb⋯N [3.028 (4) Å] inter-actions. Weak C-H⋯O inter-actions and aromatic π-π stacking [centroid-centroid separation = 3.693 (2) Å] also occur in the crystal.

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 ▶). For specialized crystallization techniques, see: Harrowfield et al. (1996 ▶).

Experimental

Crystal data

[Pb(C13H11N4O)]ClO4

M = 545.90

Monoclinic,

a = 10.0620 (6) Å

b = 14.4431 (8) Å

c = 11.1456 (7) Å

β = 99.174 (1)°

V = 1599.03 (16) Å3

Z = 4

Mo Kα radiation

μ = 10.75 mm−1

T = 293 K

0.29 × 0.11 × 0.10 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.691, T max = 1.000

8396 measured reflections

2811 independent reflections

2392 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.022

wR(F 2) = 0.056

S = 1.07

2811 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.55 e Å−3

Δρmin = −0.45 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811046691/hb6465sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811046691/hb6465Isup2.hkl

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

[Pb(C13H11N4O)]ClO4	F(000) = 1024
Mr = 545.90	Dx = 2.268 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4195 reflections
a = 10.0620 (6) Å	θ = 2.3–25.0°
b = 14.4431 (8) Å	µ = 10.75 mm−1
c = 11.1456 (7) Å	T = 293 K
β = 99.174 (1)°	Needle, yellow
V = 1599.03 (16) Å3	0.29 × 0.11 × 0.10 mm
Z = 4

Bruker SMART CCD diffractometer	2811 independent reflections
Radiation source: fine-focus sealed tube	2392 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
Tmin = 0.691, Tmax = 1.000	k = −11→17
8396 measured reflections	l = −13→13

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.056	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0241P)2 + 1.6546P] where P = (Fo2 + 2Fc2)/3
2811 reflections	(Δ/σ)max = 0.001
218 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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.

	x	y	z	Uiso*/Ueq
Pb	0.260829 (17)	0.509355 (12)	0.899845 (16)	0.03242 (8)
O1	0.3478 (3)	0.6440 (2)	1.0129 (3)	0.0444 (9)
N1	0.3495 (4)	0.4394 (3)	0.7130 (4)	0.0376 (10)
N2	0.4858 (4)	0.5592 (3)	0.8673 (3)	0.0308 (9)
N3	0.5527 (4)	0.6241 (3)	0.9458 (4)	0.0350 (10)
N4	0.6569 (4)	0.8756 (3)	1.2492 (4)	0.0388 (10)
C1	0.4775 (5)	0.4584 (3)	0.7001 (4)	0.0341 (11)
C2	0.5405 (6)	0.4140 (4)	0.6142 (5)	0.0435 (13)
H2	0.6291	0.4280	0.6070	0.052*
C3	0.4696 (7)	0.3487 (4)	0.5400 (5)	0.0528 (15)
H3	0.5103	0.3183	0.4818	0.063*
C4	0.3396 (6)	0.3285 (4)	0.5516 (5)	0.0511 (15)
H4	0.2907	0.2843	0.5021	0.061*
C5	0.2827 (6)	0.3754 (4)	0.6388 (5)	0.0465 (13)
H5	0.1940	0.3621	0.6466	0.056*
C6	0.5476 (5)	0.5291 (3)	0.7823 (4)	0.0303 (10)
C7	0.6833 (5)	0.5647 (4)	0.7653 (5)	0.0457 (13)
H7A	0.6929	0.6278	0.7926	0.068*
H7B	0.6918	0.5617	0.6808	0.068*
H7C	0.7521	0.5275	0.8117	0.068*
C8	0.4712 (5)	0.6637 (3)	1.0126 (4)	0.0310 (11)
C9	0.5353 (5)	0.7392 (3)	1.0933 (4)	0.0328 (11)
C10	0.4698 (5)	0.7752 (3)	1.1837 (5)	0.0367 (11)
H10	0.3848	0.7541	1.1932	0.044*
C11	0.5342 (5)	0.8432 (3)	1.2592 (5)	0.0389 (12)
H11	0.4903	0.8675	1.3196	0.047*
C12	0.7181 (6)	0.8406 (4)	1.1623 (6)	0.0511 (15)
H12	0.8036	0.8621	1.1550	0.061*
C13	0.6599 (5)	0.7735 (4)	1.0819 (5)	0.0492 (14)
H13	0.7048	0.7518	1.0207	0.059*
Cl1	0.95237 (15)	0.36424 (10)	0.81424 (16)	0.0580 (4)
O2	0.8284 (6)	0.3288 (5)	0.7644 (6)	0.123 (2)
O3	1.0468 (7)	0.2953 (5)	0.8172 (8)	0.166 (4)
O4	0.9936 (6)	0.4365 (4)	0.7458 (5)	0.1034 (19)
O5	0.9435 (7)	0.3990 (5)	0.9303 (6)	0.136 (3)

	U11	U22	U33	U12	U13	U23
Pb	0.02641 (11)	0.03361 (12)	0.03622 (12)	−0.00167 (8)	0.00186 (8)	0.00472 (8)
O1	0.024 (2)	0.051 (2)	0.058 (2)	−0.0028 (16)	0.0077 (17)	−0.0170 (18)
N1	0.038 (2)	0.035 (2)	0.039 (2)	−0.0048 (18)	0.0035 (19)	−0.0047 (18)
N2	0.026 (2)	0.028 (2)	0.037 (2)	0.0003 (16)	−0.0002 (18)	−0.0026 (17)
N3	0.032 (2)	0.031 (2)	0.040 (2)	−0.0021 (17)	0.0030 (19)	−0.0055 (18)
N4	0.033 (2)	0.034 (2)	0.048 (3)	−0.0015 (18)	0.002 (2)	−0.0085 (19)
C1	0.042 (3)	0.026 (2)	0.033 (3)	0.000 (2)	0.004 (2)	0.003 (2)
C2	0.050 (3)	0.039 (3)	0.044 (3)	−0.005 (2)	0.016 (3)	−0.008 (2)
C3	0.071 (4)	0.043 (3)	0.047 (3)	−0.005 (3)	0.018 (3)	−0.011 (3)
C4	0.069 (4)	0.043 (3)	0.038 (3)	−0.017 (3)	0.001 (3)	−0.013 (3)
C5	0.038 (3)	0.044 (3)	0.055 (3)	−0.012 (2)	0.000 (3)	−0.006 (3)
C6	0.029 (3)	0.029 (2)	0.033 (3)	0.001 (2)	0.003 (2)	0.002 (2)
C7	0.041 (3)	0.052 (3)	0.046 (3)	−0.010 (3)	0.015 (3)	−0.008 (3)
C8	0.030 (3)	0.028 (2)	0.033 (3)	0.0022 (19)	−0.002 (2)	0.0010 (19)
C9	0.033 (3)	0.029 (3)	0.034 (3)	0.000 (2)	−0.001 (2)	−0.004 (2)
C10	0.030 (3)	0.037 (3)	0.043 (3)	0.000 (2)	0.005 (2)	−0.004 (2)
C11	0.037 (3)	0.040 (3)	0.040 (3)	0.001 (2)	0.008 (2)	−0.007 (2)
C12	0.036 (3)	0.051 (3)	0.070 (4)	−0.011 (3)	0.018 (3)	−0.023 (3)
C13	0.040 (3)	0.052 (3)	0.059 (4)	−0.011 (3)	0.019 (3)	−0.020 (3)
Cl1	0.0411 (8)	0.0515 (9)	0.0836 (12)	−0.0050 (7)	0.0165 (8)	0.0117 (8)
O2	0.070 (4)	0.162 (6)	0.140 (5)	−0.055 (4)	0.026 (4)	−0.042 (5)
O3	0.128 (6)	0.143 (6)	0.246 (9)	0.083 (5)	0.084 (6)	0.103 (6)
O4	0.114 (5)	0.073 (3)	0.132 (5)	−0.007 (3)	0.046 (4)	0.040 (3)
O5	0.134 (6)	0.191 (7)	0.090 (4)	−0.061 (5)	0.035 (4)	−0.037 (5)

Pb—O1	2.405 (3)	C4—H4	0.9300
Pb—N1	2.597 (4)	C5—H5	0.9300
Pb—N2	2.456 (4)	C6—C7	1.499 (6)
Pb—N4i	2.472 (4)	C7—H7A	0.9600
O1—C8	1.274 (5)	C7—H7B	0.9600
N1—C1	1.347 (6)	C7—H7C	0.9600
N1—C5	1.347 (6)	C8—C9	1.494 (6)
N2—C6	1.289 (6)	C9—C13	1.372 (7)
N2—N3	1.383 (5)	C9—C10	1.389 (7)
N3—C8	1.322 (6)	C10—C11	1.385 (7)
N4—C12	1.329 (6)	C10—H10	0.9300
N4—C11	1.341 (6)	C11—H11	0.9300
N4—Pbii	2.472 (4)	C12—C13	1.385 (7)
C1—C2	1.387 (7)	C12—H12	0.9300
C1—C6	1.475 (7)	C13—H13	0.9300
C2—C3	1.376 (7)	Cl1—O3	1.372 (6)
C2—H2	0.9300	Cl1—O2	1.380 (5)
C3—C4	1.367 (8)	Cl1—O4	1.394 (5)
C3—H3	0.9300	Cl1—O5	1.404 (6)
C4—C5	1.381 (7)
O1—Pb—N2	64.75 (12)	N2—C6—C7	122.3 (4)
O1—Pb—N4i	83.77 (14)	C1—C6—C7	120.9 (4)
N2—Pb—N4i	90.17 (13)	C6—C7—H7A	109.5
O1—Pb—N1	126.27 (12)	C6—C7—H7B	109.5
N2—Pb—N1	63.45 (12)	H7A—C7—H7B	109.5
N4i—Pb—N1	83.07 (13)	C6—C7—H7C	109.5
C8—O1—Pb	116.9 (3)	H7A—C7—H7C	109.5
C1—N1—C5	117.8 (4)	H7B—C7—H7C	109.5
C1—N1—Pb	117.6 (3)	O1—C8—N3	126.7 (4)
C5—N1—Pb	123.9 (3)	O1—C8—C9	119.3 (4)
C6—N2—N3	116.7 (4)	N3—C8—C9	114.1 (4)
C6—N2—Pb	125.0 (3)	C13—C9—C10	118.6 (4)
N3—N2—Pb	118.2 (3)	C13—C9—C8	121.4 (4)
C8—N3—N2	111.5 (4)	C10—C9—C8	120.0 (4)
C12—N4—C11	117.9 (4)	C11—C10—C9	118.4 (5)
C12—N4—Pbii	123.8 (3)	C11—C10—H10	120.8
C11—N4—Pbii	118.3 (3)	C9—C10—H10	120.8
N1—C1—C2	122.0 (5)	N4—C11—C10	123.0 (5)
N1—C1—C6	116.5 (4)	N4—C11—H11	118.5
C2—C1—C6	121.6 (5)	C10—C11—H11	118.5
C3—C2—C1	118.8 (5)	N4—C12—C13	122.8 (5)
C3—C2—H2	120.6	N4—C12—H12	118.6
C1—C2—H2	120.6	C13—C12—H12	118.6
C2—C3—C4	120.2 (5)	C9—C13—C12	119.4 (5)
C2—C3—H3	119.9	C9—C13—H13	120.3
C4—C3—H3	119.9	C12—C13—H13	120.3
C3—C4—C5	118.2 (5)	O3—Cl1—O2	108.6 (5)
C3—C4—H4	120.9	O3—Cl1—O4	106.9 (4)
C5—C4—H4	120.9	O2—Cl1—O4	112.7 (4)
N1—C5—C4	123.1 (5)	O3—Cl1—O5	112.5 (5)
N1—C5—H5	118.5	O2—Cl1—O5	108.5 (4)
C4—C5—H5	118.5	O4—Cl1—O5	107.7 (4)
N2—C6—C1	116.8 (4)
N2—Pb—O1—C8	−10.2 (3)	C3—C4—C5—N1	−0.4 (9)
N4i—Pb—O1—C8	−103.3 (4)	N3—N2—C6—C1	178.8 (4)
N1—Pb—O1—C8	−26.7 (4)	Pb—N2—C6—C1	−0.9 (6)
O1—Pb—N1—C1	23.1 (4)	N3—N2—C6—C7	−2.2 (7)
N2—Pb—N1—C1	6.4 (3)	Pb—N2—C6—C7	178.1 (3)
N4i—Pb—N1—C1	100.1 (3)	N1—C1—C6—N2	7.1 (7)
O1—Pb—N1—C5	−166.7 (4)	C2—C1—C6—N2	−172.7 (4)
N2—Pb—N1—C5	176.6 (4)	N1—C1—C6—C7	−171.9 (4)
N4i—Pb—N1—C5	−89.7 (4)	C2—C1—C6—C7	8.2 (7)
O1—Pb—N2—C6	−167.9 (4)	Pb—O1—C8—N3	8.1 (6)
N4i—Pb—N2—C6	−84.9 (4)	Pb—O1—C8—C9	−172.5 (3)
N1—Pb—N2—C6	−2.7 (3)	N2—N3—C8—O1	3.4 (7)
O1—Pb—N2—N3	12.4 (3)	N2—N3—C8—C9	−176.0 (4)
N4i—Pb—N2—N3	95.4 (3)	O1—C8—C9—C13	−169.0 (5)
N1—Pb—N2—N3	177.6 (3)	N3—C8—C9—C13	10.5 (7)
C6—N2—N3—C8	167.1 (4)	O1—C8—C9—C10	12.2 (7)
Pb—N2—N3—C8	−13.1 (5)	N3—C8—C9—C10	−168.3 (4)
C5—N1—C1—C2	−0.4 (7)	C13—C9—C10—C11	−0.8 (8)
Pb—N1—C1—C2	170.4 (4)	C8—C9—C10—C11	178.0 (4)
C5—N1—C1—C6	179.8 (5)	C12—N4—C11—C10	0.3 (8)
Pb—N1—C1—C6	−9.5 (5)	Pbii—N4—C11—C10	−176.6 (4)
N1—C1—C2—C3	0.2 (8)	C9—C10—C11—N4	−0.2 (8)
C6—C1—C2—C3	−179.9 (5)	C11—N4—C12—C13	0.7 (9)
C1—C2—C3—C4	−0.2 (9)	Pbii—N4—C12—C13	177.4 (4)
C2—C3—C4—C5	0.2 (9)	C10—C9—C13—C12	1.7 (8)
C1—N1—C5—C4	0.5 (8)	C8—C9—C13—C12	−177.1 (5)
Pb—N1—C5—C4	−169.7 (4)	N4—C12—C13—C9	−1.7 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3iii	0.93	2.53	3.422 (10)	160
C4—H4···O1iv	0.93	2.45	3.277 (7)	148
C10—H10···O2v	0.93	2.57	3.485 (8)	170

Table 1

Selected bond lengths (Å)

Pb—O1	2.405 (3)
Pb—N1	2.597 (4)
Pb—N2	2.456 (4)
Pb—N4i	2.472 (4)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ii	0.93	2.53	3.422 (10)	160
C4—H4⋯O1iii	0.93	2.45	3.277 (7)	148
C10—H10⋯O2iv	0.93	2.57	3.485 (8)	170

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