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

Shahverdizadeh, G.H.; Tiekink, E.R.T.; Mirtamizdoust, B.

doi:10.1107/S1600536811046691

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1727-m1728

https://doi.org/10.1107/S1600536811046691

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

Gholam Hossein Shahverdizadeh,^a ‡ Edward R. T. Tiekink ^b ^* and Babak Mirtamizdoust ^c

^aDepartment of Chemistry, Faculty of Science, Tabriz Branch, Islamic Azad University, PO Box 1655, Tabriz, Iran, ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cDepartment of Inorganic Chemistry, Faculty of Chemistry, University of Tabriz, PO Box 5166616471, Tabriz, Iran
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 19 October 2011; accepted 5 November 2011; online 9 November 2011)

The Pb^II atom in the polymeric title compound, {[Pb(C₁₃H₁₁N₄O)]ClO₄}_n, is coordinated by the N′-[1-(pyridin-2-yl-κN)ethylidene]isonicotinohydrazidate ligand via its O,N,N′-donors and simultaneously bridged by a neighbouring ligand via the pyridin-2-yl N atom. The resultant supramolecular chain is a zigzag along the a axis. The stereochemistry of the Pb^II atom is defined by an N₃OE 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 supramolecular 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] interactions. Weak C—H⋯O interactions 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_r = 545.90
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.022
wR(F²) = 0.056
S = 1.07
2811 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.55 e Å⁻³
Δρ_min = −0.45 e Å⁻³

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) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

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⋯O2^iv	0.93	2.57	3.485 (8)	170
Symmetry codes: (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) -x+1, -y+1, -z+2.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046691/hb6465sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046691/hb6465Isup2.hkl

checkCIF report

Comment top

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 the title lead(II) complex, (I), all four donor atoms participate in coordination of the Pb atom.

The asymmetric unit of (I), Fig. 1, comprises a Pb atom, a N'-[1-(2-pyridyl)ethylidene]isonicotinohydrazide anion and a perchlorate anion. 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.

The resultant N₃O donor set plus the lone pair of electrons is based on a trigonal bipyramid with the O1 and N1 atoms in axial positions [O1—Pb—N1 = 126.27 (12)°] and the remaining N atoms [N2—Pb—N4ⁱ = 90.17 (13)°] and lone pair in equatorial positions; symmetry operation i: -1/2 + x, 1.5 - y, -1/2 + z. The µ₂-bridging mode of the tetradentate N'-[1-(2-pyridyl)ethylidene]isonicotinohydrazide ligand leads to a zigzag chain along the a axis, Fig. 2. The considerable distortions from the ideal geometry arise from the acute chelate angles (O1—Pb—N2 = 64.75 (12)° and N1—Pb—N2 = 63.45 (12)°) as well as the close approach of other donor atoms. Most notable amongst the latter are Pb···O(perchlorate) interactions with the two shortest contacts being Pb···O4ⁱⁱ of 3.133 (6) Å and Pb···O5ⁱⁱⁱ = 3.287 (7) Å for i: -1 + x, y, z and ii: 1 - x, 1 - y, 2 - z. These interactions along with Pb···N3ⁱⁱⁱ contacts of 3.028 (4) Å [iii: 1 - x, 1 - y, 2 - z] generate a three-dimensional architecture, Fig. 3.

Related literature top

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 top

A solution of methyl 2-pyridyl ketone (10 mmol) in MeOH (25 ml) was added drop wise to a solution of 4-pyridinecarboxylic acid hydrazide (10 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 ligand (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 1 week, yellow needles of (I) had deposited in the arm held at ambient temperature. They were then filtered off, washed with acetone and ether, and air dried. Yield: 75%. M.pt.: 506 K

Structure description top

Computing details top

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 top

	Fig. 1. The asymmetric unit of (I) showing displacement ellipsoids at the 35% probability level. The molecular structure has been expanded to indicate the µ₂-bridging mode of the tetradentate ligand. Symmetry operation i: -1/2 + x, 1.5 - y, -1/2 + z; ii: 1/2 + x, 1.5 - y, 1/2 + z.
	Fig. 2. A view of the zigzag chain along the a axis in (I).
	Fig. 3. A view in projection down the a axis of the crystal packing in (I). The weaker Pb···O and Pb···N interactions (see text) are shown as black and blue dashed lines, respectively.

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

Crystal data top

[Pb(C₁₃H₁₁N₄O)]ClO₄	F(000) = 1024
M_r = 545.90	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0241P)² + 1.6546P] where P = (F_o² + 2F_c²)/3
2811 reflections	(Δ/σ)_max = 0.001
218 parameters	Δρ_max = 0.55 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Pb(C₁₃H₁₁N₄O)]ClO₄	V = 1599.03 (16) Å³
M_r = 545.90	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0620 (6) Å	µ = 10.75 mm⁻¹
b = 14.4431 (8) Å	T = 293 K
c = 11.1456 (7) Å	0.29 × 0.11 × 0.10 mm
β = 99.174 (1)°

Data collection top

Bruker SMART CCD diffractometer	2811 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2392 reflections with I > 2σ(I)
T_min = 0.691, T_max = 1.000	R_int = 0.026
8396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.056	H-atom parameters constrained
S = 1.07	Δρ_max = 0.55 e Å⁻³
2811 reflections	Δρ_min = −0.45 e Å⁻³
218 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

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

Hydrogen-bond geometry (Å, º) top

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···O1^iv	0.93	2.45	3.277 (7)	148
C10—H10···O2^v	0.93	2.57	3.485 (8)	170

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

Experimental details

Crystal data
Chemical formula	[Pb(C₁₃H₁₁N₄O)]ClO₄
M_r	545.90
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.0620 (6), 14.4431 (8), 11.1456 (7)
β (°)	99.174 (1)
V (Å³)	1599.03 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.75
Crystal size (mm)	0.29 × 0.11 × 0.10

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.691, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	8396, 2811, 2392
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.056, 1.07
No. of reflections	2811
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.55, −0.45

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

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

Symmetry code: (i) x−1/2, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

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···O2^iv	0.93	2.57	3.485 (8)	170

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

Footnotes

‡Additional correspondence author, e-mail: shahverdizadeh@iaut.ac.ir.

Acknowledgements

The authors thank the Islamic Azad University for support.

References

Abboud, K. A., Palenik, R. C., Palenik, G. J. & Wood, R. M. (2007). Inorg. Chim. Acta, 360, 3642–3646. Web of Science CSD CrossRef CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hao, Z.-Y., Liu, Q.-W., Xu, J., Jia, L. & Li, S.-B. (2010). Chem. Pharm. Bull. 58, 1306–1312. CSD CrossRef CAS PubMed Google Scholar
Harrowfield, J. M., Miyamae, H., Skelton, B. W., Soudi, A. A. & White, A. H. (1996). Aust. J. Chem. 49, 1165–1169. CSD CrossRef Web of Science Google Scholar
Maurya, M. R., Khurana, S., Zhang, W. & Rehder, D. J. (2002). J. Chem. Soc. Dalton Trans. pp. 3015–3023. Web of Science CSD CrossRef Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, Y.-Y. & Liu, S.-X. (2009). Acta Cryst. C65, m269–m272. Web of Science CSD CrossRef IUCr Journals Google Scholar

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