catena-Poly[[[bis­(methanol-κO)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/S1600536811046769

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Pages m1729-m1730

https://doi.org/10.1107/S1600536811046769

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catena-Poly[[[bis(methanol-κO)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 4 November 2011; accepted 5 November 2011; online 9 November 2011)

The Pb^II atom in the polymeric title compound, {[Pb(C₁₃H₁₁N₄O)(CH₃OH)₂]ClO₄}_n, is coordinated by an N′-[1-(pyridin-2-yl-κN)ethylidene]isonicotinohydrazidate ligand via O,N,N′-donors and simultaneously bridged by a neighbouring ligand via the isonicotinoyl N atom; two additional sites are occupied by methanol O atoms. The resultant supramolecular chain is a zigzag along the c axis. The Pb^II atom is seven-coordinated within an N₃O₃ donor set and a lone pair of electrons, which defines a Ψ-pentagonal–bipyramidal coordination geometry with the pyridine N and lone pair in axial positions. The supramolecular chains are linked into the two-dimensional array via intermolecular Pb⋯N [3.020 (4) Å] interactions. Layers stack along the a axis, being connected by O—H⋯O hydrogen bonds formed between the coordinated methanol molecules and perchlorate anions.

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 ); Shahverdizadeh et al. (2011 ). For specialized crystallization techniques, see: Harrowfield et al. (1996 ).

Experimental

Crystal data

[Pb(C₁₃H₁₁N₄O)(CH₄O)₂]ClO₄
M_r = 609.98
Monoclinic, P 2₁ /c
a = 11.2122 (14) Å
b = 13.4644 (17) Å
c = 14.1451 (18) Å
β = 111.906 (2)°
V = 1981.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 8.70 mm⁻¹
T = 173 K
0.46 × 0.43 × 0.37 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.108, T_max = 0.141
10367 measured reflections
3492 independent reflections
2641 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.066
S = 1.05
3492 reflections
255 parameters
H-atom parameters constrained
Δρ_max = 0.97 e Å⁻³
Δρ_min = −0.98 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb—O1	2.415 (3)
Pb—O2	2.733 (4)
Pb—O3	2.891 (4)
Pb—N1	2.669 (4)
Pb—N2	2.493 (4)
Pb—N4ⁱ	2.477 (4)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2o⋯O4	0.84	2.16	2.909 (7)	149
O3—H3o⋯O5ⁱⁱ	0.84	2.11	2.930 (7)	166
Symmetry code: (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536811046769/hg5133sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046769/hg5133Isup2.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 a recently reported Pb^II structure, all four donor atoms were involved in coordination leading to a zigzag chain (Shahverdizadeh et al., 2011). A similar mode of coordination was found in the title lead(II) complex, (I), with complete details described herein.

The crystallographic asymmetric unit of (I), Fig. 1, comprises a Pb^II atom, an N'-1-(2-pyridyl)ethylidene]isonicotinohydrazide anion, a perchlorate anion, and two methanol molecules. 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. Both methanol molecules are connected to the Pb^II atom. The resulting N₃O₃ donor set, along with a stereochemically active lone pair of electrons, define a pentagonal bipyramidal geometry with the pyridyl-N4 atom lone pair of electrons occupying axial positions. The µ₂-bridging mode of the tetradentate N'-[1-(2-pyridyl)ethylidene]isonicotinohydrazide ligand leads to a zigzag chain (glide symmetry) along the c axis, Fig. 2.

In the crystal packing, centrosymmetrically related supramolecular chains are linked into a two-dimensional array by Pb···N interactions [Pb···N3ⁱ = 3.020 (4) Å for i: 1 - x, 1 - y, 1 - z]. The layers thus formed in the bc plane are connected into a three-dimensional architecture via O—H···O hydrogen bonds involving the coordinated methanol molecules and the perchlorate anions, Fig. 4 and Table 2.

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); Shahverdizadeh et al. (2011). For specialized crystallization techniques, see: Harrowfield et al. (1996).

Experimental top

A solution of methyl 2-pyridyl ketone (15 mmol) in MeOH (25 ml) was added drop-wise to a solution of 4-pyridinecarboxylic acid hydrazide (15 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 compound (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 2 weeks, crystals had deposited in the arm held at ambient temperature. They were filtered off, washed with acetone and ether, and air dried. Yield: 66%; M.pt.: 516 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 the atom-labelling scheme and displacement ellipsoids at the 50% probability level. The molecular structure has been expanded to indicate the µ₂-bridging mode of the tetradentate ligand. Symmetry operations i: x, 0.5 - y, -1/2 + z; ii: x, 1/2 + y, 0.5 - z.
	Fig. 2. A view of the supramolecular zigzag chain along the c axis in (I).
	Fig. 3. A view of the two-dimensional array in the bc plane in (I). The weaker Pb···N interactions (see text) are shown as blue dashed lines.
	Fig. 4. A view in projection down the c axis of the crystal packing in (I). The weaker Pb···N interactions (see text) are shown as blue dashed lines, and the O—H···O hydrogen bonds are shown as orange dashed lines.

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

Crystal data top

[Pb(C₁₃H₁₁N₄O)(CH₄O)₂]ClO₄	F(000) = 1168
M_r = 609.98	D_x = 2.045 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4546 reflections
a = 11.2122 (14) Å	θ = 2.2–25.0°
b = 13.4644 (17) Å	µ = 8.70 mm⁻¹
c = 14.1451 (18) Å	T = 173 K
β = 111.906 (2)°	Prism, yellow
V = 1981.2 (4) Å³	0.46 × 0.43 × 0.37 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3492 independent reflections
Radiation source: fine-focus sealed tube	2641 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→8
T_min = 0.108, T_max = 0.141	k = −16→15
10367 measured reflections	l = −12→16

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0282P)² + 6.1832P] where P = (F_o² + 2F_c²)/3
3492 reflections	(Δ/σ)_max = 0.001
255 parameters	Δρ_max = 0.97 e Å⁻³
0 restraints	Δρ_min = −0.98 e Å⁻³

Crystal data top

[Pb(C₁₃H₁₁N₄O)(CH₄O)₂]ClO₄	V = 1981.2 (4) Å³
M_r = 609.98	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2122 (14) Å	µ = 8.70 mm⁻¹
b = 13.4644 (17) Å	T = 173 K
c = 14.1451 (18) Å	0.46 × 0.43 × 0.37 mm
β = 111.906 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3492 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2641 reflections with I > 2σ(I)
T_min = 0.108, T_max = 0.141	R_int = 0.027
10367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.05	Δρ_max = 0.97 e Å⁻³
3492 reflections	Δρ_min = −0.98 e Å⁻³
255 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	0.379666 (16)	0.502370 (14)	0.303341 (13)	0.01308 (8)
Cl1	−0.07646 (14)	0.25586 (11)	0.34029 (12)	0.0297 (3)
O1	0.3551 (3)	0.3685 (3)	0.4082 (3)	0.0160 (8)
O2	0.1391 (4)	0.4209 (3)	0.2361 (3)	0.0304 (10)
H2O	0.1367	0.3678	0.2666	0.037*
O3	0.2933 (5)	0.5804 (4)	0.0983 (3)	0.0449 (12)
H3O	0.2399	0.6262	0.0916	0.054*
O4	0.0480 (5)	0.2805 (5)	0.3505 (4)	0.080 (2)
O5	−0.0732 (6)	0.2110 (5)	0.4315 (4)	0.081 (2)
O6	−0.1531 (6)	0.3419 (5)	0.3194 (5)	0.088 (2)
O7	−0.1306 (6)	0.1904 (5)	0.2568 (4)	0.076 (2)
N1	0.6011 (4)	0.5630 (3)	0.2931 (3)	0.0171 (10)
N2	0.5835 (4)	0.4394 (3)	0.4342 (3)	0.0138 (9)
N3	0.5741 (4)	0.3751 (3)	0.5074 (3)	0.0138 (9)
N4	0.4129 (4)	0.1305 (3)	0.6945 (3)	0.0168 (10)
C1	0.7110 (5)	0.5362 (4)	0.3701 (4)	0.0136 (11)
C2	0.8302 (5)	0.5696 (4)	0.3747 (5)	0.0255 (13)
H2	0.9062	0.5498	0.4293	0.031*
C3	0.8377 (6)	0.6317 (5)	0.2996 (5)	0.0313 (15)
H3	0.9188	0.6541	0.3011	0.038*
C4	0.7259 (6)	0.6607 (4)	0.2223 (5)	0.0285 (14)
H4	0.7282	0.7047	0.1705	0.034*
C5	0.6108 (5)	0.6249 (4)	0.2216 (4)	0.0205 (12)
H5	0.5340	0.6448	0.1679	0.025*
C6	0.6980 (5)	0.4684 (4)	0.4476 (4)	0.0147 (11)
C7	0.8175 (5)	0.4367 (4)	0.5349 (4)	0.0195 (12)
H7A	0.7934	0.3963	0.5826	0.029*
H7B	0.8646	0.4956	0.5701	0.029*
H7C	0.8722	0.3975	0.5087	0.029*
C8	0.4546 (5)	0.3432 (4)	0.4834 (4)	0.0125 (11)
C9	0.4411 (5)	0.2683 (4)	0.5577 (4)	0.0120 (10)
C10	0.3203 (5)	0.2332 (4)	0.5473 (4)	0.0163 (11)
H10	0.2457	0.2561	0.4932	0.020*
C11	0.3101 (5)	0.1652 (4)	0.6160 (4)	0.0182 (12)
H11	0.2271	0.1414	0.6080	0.022*
C12	0.5287 (5)	0.1646 (4)	0.7041 (4)	0.0174 (12)
H12	0.6019	0.1410	0.7590	0.021*
C13	0.5467 (5)	0.2326 (4)	0.6377 (4)	0.0148 (11)
H13	0.6307	0.2546	0.6468	0.018*
C15	0.0171 (6)	0.4465 (6)	0.1622 (6)	0.0463 (19)
H15A	−0.0462	0.3962	0.1617	0.069*
H15B	0.0228	0.4497	0.0948	0.069*
H15C	−0.0094	0.5114	0.1791	0.069*
C16	0.3117 (8)	0.5665 (8)	0.0072 (6)	0.065 (3)
H16A	0.3963	0.5365	0.0213	0.098*
H16B	0.3071	0.6307	−0.0265	0.098*
H16C	0.2447	0.5224	−0.0373	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb	0.01177 (12)	0.01436 (11)	0.01108 (11)	0.00120 (9)	0.00192 (8)	−0.00026 (9)
Cl1	0.0206 (7)	0.0349 (8)	0.0335 (8)	−0.0006 (7)	0.0101 (6)	−0.0074 (7)
O1	0.013 (2)	0.020 (2)	0.0106 (18)	−0.0043 (15)	−0.0003 (15)	0.0014 (15)
O2	0.018 (2)	0.037 (2)	0.028 (2)	−0.0036 (18)	0.0004 (18)	0.002 (2)
O3	0.046 (3)	0.057 (3)	0.035 (3)	0.024 (2)	0.018 (2)	0.015 (2)
O4	0.028 (3)	0.143 (6)	0.057 (4)	−0.022 (3)	0.003 (3)	0.039 (4)
O5	0.099 (5)	0.097 (5)	0.048 (4)	−0.042 (4)	0.031 (3)	0.000 (3)
O6	0.078 (5)	0.084 (5)	0.098 (5)	0.040 (4)	0.027 (4)	−0.015 (4)
O7	0.078 (4)	0.075 (4)	0.050 (4)	0.013 (3)	−0.006 (3)	−0.032 (3)
N1	0.013 (2)	0.021 (2)	0.017 (2)	−0.0003 (19)	0.0044 (19)	0.0029 (19)
N2	0.018 (2)	0.011 (2)	0.013 (2)	0.0007 (18)	0.0071 (18)	0.0020 (17)
N3	0.010 (2)	0.019 (2)	0.011 (2)	−0.0015 (18)	0.0024 (18)	0.0029 (18)
N4	0.017 (2)	0.017 (2)	0.015 (2)	0.0003 (19)	0.0042 (19)	0.0030 (18)
C1	0.018 (3)	0.009 (2)	0.017 (3)	0.000 (2)	0.010 (2)	−0.003 (2)
C2	0.014 (3)	0.027 (3)	0.033 (3)	0.004 (2)	0.006 (3)	0.010 (3)
C3	0.021 (3)	0.033 (4)	0.043 (4)	0.000 (3)	0.015 (3)	0.017 (3)
C4	0.036 (4)	0.023 (3)	0.030 (4)	0.000 (3)	0.016 (3)	0.010 (3)
C5	0.023 (3)	0.020 (3)	0.017 (3)	0.000 (2)	0.005 (2)	0.005 (2)
C6	0.013 (3)	0.013 (2)	0.017 (3)	0.002 (2)	0.004 (2)	−0.001 (2)
C7	0.012 (3)	0.026 (3)	0.019 (3)	0.003 (2)	0.003 (2)	0.006 (2)
C8	0.013 (3)	0.012 (3)	0.012 (3)	0.000 (2)	0.003 (2)	−0.003 (2)
C9	0.015 (3)	0.012 (2)	0.010 (2)	−0.002 (2)	0.005 (2)	−0.003 (2)
C10	0.013 (3)	0.020 (3)	0.011 (3)	−0.002 (2)	0.000 (2)	0.000 (2)
C11	0.013 (3)	0.020 (3)	0.020 (3)	−0.005 (2)	0.004 (2)	0.000 (2)
C12	0.016 (3)	0.021 (3)	0.014 (3)	0.000 (2)	0.003 (2)	0.000 (2)
C13	0.013 (3)	0.014 (3)	0.017 (3)	0.000 (2)	0.005 (2)	0.001 (2)
C15	0.024 (4)	0.056 (5)	0.044 (4)	0.006 (3)	−0.004 (3)	−0.005 (4)
C16	0.043 (5)	0.116 (8)	0.031 (4)	0.004 (5)	0.007 (4)	0.005 (5)

Geometric parameters (Å, º) top

Pb—O1	2.415 (3)	C2—H2	0.9500
Pb—O2	2.733 (4)	C3—C4	1.378 (8)
Pb—O3	2.891 (4)	C3—H3	0.9500
Pb—N1	2.669 (4)	C4—C5	1.374 (8)
Pb—N2	2.493 (4)	C4—H4	0.9500
Pb—N4ⁱ	2.477 (4)	C5—H5	0.9500
Cl1—O4	1.389 (5)	C6—C7	1.505 (7)
Cl1—O6	1.406 (6)	C7—H7A	0.9800
Cl1—O5	1.412 (6)	C7—H7B	0.9800
Cl1—O7	1.417 (5)	C7—H7C	0.9800
O1—C8	1.268 (6)	C8—C9	1.505 (7)
O2—C15	1.420 (7)	C9—C13	1.384 (7)
O2—H2O	0.8400	C9—C10	1.389 (7)
O3—C16	1.392 (9)	C10—C11	1.371 (7)
O3—H3O	0.8400	C10—H10	0.9500
N1—C5	1.345 (7)	C11—H11	0.9500
N1—C1	1.354 (7)	C12—C13	1.379 (7)
N2—C6	1.286 (7)	C12—H12	0.9500
N2—N3	1.384 (6)	C13—H13	0.9500
N3—C8	1.325 (7)	C15—H15A	0.9800
N4—C12	1.335 (7)	C15—H15B	0.9800
N4—C11	1.351 (7)	C15—H15C	0.9800
N4—Pbⁱⁱ	2.477 (4)	C16—H16A	0.9800
C1—C2	1.389 (7)	C16—H16B	0.9800
C1—C6	1.475 (8)	C16—H16C	0.9800
C2—C3	1.379 (8)

O1—Pb—N4ⁱ	85.45 (13)	C2—C3—H3	120.5
O1—Pb—N2	64.74 (12)	C5—C4—C3	118.7 (5)
N4ⁱ—Pb—N2	84.66 (14)	C5—C4—H4	120.7
O1—Pb—N1	125.71 (12)	C3—C4—H4	120.7
N4ⁱ—Pb—N1	80.14 (14)	N1—C5—C4	123.4 (5)
N2—Pb—N1	61.99 (13)	N1—C5—H5	118.3
O1—Pb—O2	65.79 (12)	C4—C5—H5	118.3
N4ⁱ—Pb—O2	81.46 (14)	N2—C6—C1	116.6 (5)
N2—Pb—O2	129.38 (13)	N2—C6—C7	124.6 (5)
N1—Pb—O2	157.14 (13)	C1—C6—C7	118.8 (5)
O1—Pb—O3	144.62 (13)	C6—C7—H7A	109.5
N4ⁱ—Pb—O3	73.20 (14)	C6—C7—H7B	109.5
N2—Pb—O3	137.72 (13)	H7A—C7—H7B	109.5
N1—Pb—O3	78.73 (13)	C6—C7—H7C	109.5
O2—Pb—O3	83.06 (14)	H7A—C7—H7C	109.5
O4—Cl1—O6	109.6 (5)	H7B—C7—H7C	109.5
O4—Cl1—O5	108.9 (4)	O1—C8—N3	128.2 (5)
O6—Cl1—O5	110.5 (4)	O1—C8—C9	118.6 (5)
O4—Cl1—O7	109.7 (4)	N3—C8—C9	113.2 (4)
O6—Cl1—O7	107.4 (4)	C13—C9—C10	118.1 (5)
O5—Cl1—O7	110.6 (4)	C13—C9—C8	121.7 (5)
C8—O1—Pb	116.7 (3)	C10—C9—C8	120.2 (5)
C15—O2—Pb	135.5 (4)	C11—C10—C9	119.2 (5)
C15—O2—H2O	112.3	C11—C10—H10	120.4
Pb—O2—H2O	112.3	C9—C10—H10	120.4
C16—O3—Pb	140.3 (5)	N4—C11—C10	122.8 (5)
C16—O3—H3O	109.8	N4—C11—H11	118.6
Pb—O3—H3O	109.8	C10—C11—H11	118.6
C5—N1—C1	117.8 (5)	N4—C12—C13	122.9 (5)
C5—N1—Pb	124.6 (3)	N4—C12—H12	118.6
C1—N1—Pb	117.4 (3)	C13—C12—H12	118.6
C6—N2—N3	115.5 (4)	C12—C13—C9	119.3 (5)
C6—N2—Pb	126.5 (3)	C12—C13—H13	120.3
N3—N2—Pb	117.6 (3)	C9—C13—H13	120.3
C8—N3—N2	111.3 (4)	O2—C15—H15A	109.5
C12—N4—C11	117.6 (4)	O2—C15—H15B	109.5
C12—N4—Pbⁱⁱ	123.4 (3)	H15A—C15—H15B	109.5
C11—N4—Pbⁱⁱ	118.7 (3)	O2—C15—H15C	109.5
N1—C1—C2	121.5 (5)	H15A—C15—H15C	109.5
N1—C1—C6	116.8 (5)	H15B—C15—H15C	109.5
C2—C1—C6	121.7 (5)	O3—C16—H16A	109.5
C3—C2—C1	119.6 (5)	O3—C16—H16B	109.5
C3—C2—H2	120.2	H16A—C16—H16B	109.5
C1—C2—H2	120.2	O3—C16—H16C	109.5
C4—C3—C2	119.0 (6)	H16A—C16—H16C	109.5
C4—C3—H3	120.5	H16B—C16—H16C	109.5

N4ⁱ—Pb—O1—C8	94.7 (4)	C5—N1—C1—C2	−1.2 (8)
N2—Pb—O1—C8	8.5 (3)	Pb—N1—C1—C2	−175.8 (4)
N1—Pb—O1—C8	20.3 (4)	C5—N1—C1—C6	−180.0 (5)
O2—Pb—O1—C8	177.4 (4)	Pb—N1—C1—C6	5.4 (6)
O3—Pb—O1—C8	147.0 (3)	N1—C1—C2—C3	0.2 (9)
O1—Pb—O2—C15	168.6 (6)	C6—C1—C2—C3	178.9 (5)
N4ⁱ—Pb—O2—C15	−102.5 (6)	C1—C2—C3—C4	1.2 (9)
N2—Pb—O2—C15	−178.4 (5)	C2—C3—C4—C5	−1.4 (10)
N1—Pb—O2—C15	−65.8 (7)	C1—N1—C5—C4	0.9 (8)
O3—Pb—O2—C15	−28.6 (6)	Pb—N1—C5—C4	175.1 (4)
O1—Pb—O3—C16	−79.2 (8)	C3—C4—C5—N1	0.4 (9)
N4ⁱ—Pb—O3—C16	−23.8 (8)	N3—N2—C6—C1	179.5 (4)
N2—Pb—O3—C16	37.7 (9)	Pb—N2—C6—C1	−8.2 (6)
N1—Pb—O3—C16	59.1 (8)	N3—N2—C6—C7	0.4 (7)
O2—Pb—O3—C16	−107.0 (8)	Pb—N2—C6—C7	172.8 (4)
O1—Pb—N1—C5	167.4 (4)	N1—C1—C6—N2	1.1 (7)
N4ⁱ—Pb—N1—C5	90.3 (4)	C2—C1—C6—N2	−177.7 (5)
N2—Pb—N1—C5	179.5 (5)	N1—C1—C6—C7	−179.8 (5)
O2—Pb—N1—C5	53.5 (6)	C2—C1—C6—C7	1.4 (8)
O3—Pb—N1—C5	15.6 (4)	Pb—O1—C8—N3	−6.4 (7)
O1—Pb—N1—C1	−18.5 (4)	Pb—O1—C8—C9	173.2 (3)
N4ⁱ—Pb—N1—C1	−95.5 (4)	N2—N3—C8—O1	−3.9 (7)
N2—Pb—N1—C1	−6.3 (3)	N2—N3—C8—C9	176.6 (4)
O2—Pb—N1—C1	−132.3 (4)	O1—C8—C9—C13	175.8 (5)
O3—Pb—N1—C1	−170.2 (4)	N3—C8—C9—C13	−4.6 (7)
O1—Pb—N2—C6	177.0 (5)	O1—C8—C9—C10	−4.4 (7)
N4ⁱ—Pb—N2—C6	89.5 (4)	N3—C8—C9—C10	175.2 (5)
N1—Pb—N2—C6	7.8 (4)	C13—C9—C10—C11	0.0 (7)
O2—Pb—N2—C6	163.8 (4)	C8—C9—C10—C11	−179.8 (5)
O3—Pb—N2—C6	31.8 (5)	C12—N4—C11—C10	−0.3 (8)
O1—Pb—N2—N3	−10.8 (3)	Pbⁱⁱ—N4—C11—C10	−175.1 (4)
N4ⁱ—Pb—N2—N3	−98.3 (3)	C9—C10—C11—N4	0.4 (8)
N1—Pb—N2—N3	−180.0 (4)	C11—N4—C12—C13	−0.1 (8)
O2—Pb—N2—N3	−24.0 (4)	Pbⁱⁱ—N4—C12—C13	174.4 (4)
O3—Pb—N2—N3	−156.0 (3)	N4—C12—C13—C9	0.4 (8)
C6—N2—N3—C8	−175.1 (4)	C10—C9—C13—C12	−0.4 (7)
Pb—N2—N3—C8	11.8 (5)	C8—C9—C13—C12	179.4 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O4	0.84	2.16	2.909 (7)	149
O3—H3o···O5ⁱⁱⁱ	0.84	2.11	2.930 (7)	166

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

Experimental details

Crystal data
Chemical formula	[Pb(C₁₃H₁₁N₄O)(CH₄O)₂]ClO₄
M_r	609.98
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	11.2122 (14), 13.4644 (17), 14.1451 (18)
β (°)	111.906 (2)
V (Å³)	1981.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	8.70
Crystal size (mm)	0.46 × 0.43 × 0.37

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.108, 0.141
No. of measured, independent and observed [I > 2σ(I)] reflections	10367, 3492, 2641
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.066, 1.05
No. of reflections	3492
No. of parameters	255
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.97, −0.98

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	2.415 (3)	Pb—N1	2.669 (4)
Pb—O2	2.733 (4)	Pb—N2	2.493 (4)
Pb—O3	2.891 (4)	Pb—N4ⁱ	2.477 (4)

Symmetry code: (i) x, −y+1/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2o···O4	0.84	2.16	2.909 (7)	149
O3—H3o···O5ⁱⁱ	0.84	2.11	2.930 (7)	166

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

Footnotes

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

Acknowledgements

The authors thank the Islamic Azad University for support.

References

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