Bis(μ-azido-κ2N1:N1)bis­{(acetato-κ2O,O′)[2,4,6-tris­(2-pyrid­yl)-1,3,5-triazine-κ3N2,N1,N6]lead(II)}

Dayani, M.; Ghaemi, A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536811038116

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page m1419

https://doi.org/10.1107/S1600536811038116

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Bis(μ-azido-κ²N¹:N¹)bis{(acetato-κ²O,O′)[2,4,6-tris(2-pyridyl)-1,3,5-triazine-κ³N²,N¹,N⁶]lead(II)}

Milad Dayani,^a Akbar Ghaemi,^b ‡ Seik Weng Ng ^c,^d and Edward R. T. Tiekink ^c ^*

^aYoung Researchers Club, Saveh Branch, Islamic Azad University, Saveh, Iran, ^bDepartment of Chemistry, Saveh Branch, Islamic Azad University, Saveh, Iran, ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of, Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 17 September 2011; accepted 18 September 2011; online 30 September 2011)

The complete dinuclear title complex, [Pb₂(C₂H₃O₂)₂(N₃)₂(C₁₈H₁₂N₆)₂], is generated by the application of a crystallographic centre of inversion. The Pb^II atom is coordinated by three N atoms of the tridentate ligand, two O atoms derived from an asymmetrically coordinating acetate ligand, and two azido-N atoms derived from two asymmetrically bridging azido ligands. The metal coordination geometry can be described as a square anti-prism with one position occupied by an unseen lone pair of electrons. In the ligand, the two coordinating pyridine rings are almost co-planar with the central pyrazine ring [dihedral angles = 0.47 (17) and 0.83 (18)°], but the terminal ring is twisted [dihedral angle = 19.76 (18)°]. In the crystal, the presence of π–π interactions [ring centroid distance between pyridyl rings = 3.581 (2) Å] leads to supramolecular chains along the a-axis direction.

Related literature

For related lead(II) complexes with the 2,4,6-tris(2-pyridyl)-1,3,5-triazine ligand, see: Harrowfield et al. (1996a ,b , 2002 ).

Experimental

Crystal data

[Pb₂(C₂H₃O₂)₂(N₃)₂(C₁₈H₁₂N₆)₂]
M_r = 1241.22
Triclinic, $[P \overline 1]$
a = 8.5529 (4) Å
b = 11.0080 (5) Å
c = 11.8617 (5) Å
α = 86.739 (4)°
β = 70.928 (4)°
γ = 70.100 (4)°
V = 990.60 (8) Å³
Z = 1
Mo Kα radiation
μ = 8.56 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ) T_min = 0.279, T_max = 0.482
7814 measured reflections
4358 independent reflections
4046 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.049
S = 0.97
4358 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 2.01 e Å⁻³
Δρ_min = −2.14 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb—O1	2.349 (3)
Pb—O2	2.550 (3)
Pb—N1	2.684 (3)
Pb—N2	2.698 (3)
Pb—N6	2.702 (3)
Pb—N7	2.586 (3)
Pb—N7ⁱ	2.874 (3)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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 general, I. DOI: https://doi.org/10.1107/S1600536811038116/hb6410sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811038116/hb6410Isup2.hkl

checkCIF report

Comment top

Lead(II) complexes of the 2,4,6-tris(2-pyridyl)-1,3,5-triazine ligand (tptz) have been reported in the literature (Harrowfield et al. 1996a; Harrowfield et al. 1996b; Harrowfield et al. 2002). In each of the nine known structures, the tptz ligand has been shown to function as a tridentate ligand as observed in the dinuclear structure of the title compound, (I).

The complete dinuclear molecule of (I) is generated by the application of a centre of inversion. The Pb^II atom is seven coordinate within a N₅O₂ donor set defined by three N atoms of the tptz ligand, two atoms derived from two µ-azido anions, and two O atoms derived from an asymmetrically chelating acetate, Table 1. The coordination geometry is based on a square anti-prism with one face defined by the O1, O2, N2 and N6 atoms, and the other by the N1, N7, N7ⁱ and the lone pair of electrons; symmetry operation i: 1 - x, 1 - y, -z. The µ-azido bridge is non-symmetric, Table 1, leading the Pb₂N₂ central ring to have the shape of a trapezium. Within the tptz ligand, the two coordinating pyridine rings are co-planar with the central pyrazine ring (r.m.s. deviation = 0.016 Å), forming dihedral angles of 0.47 (17) (N1-pyridine) and 0.83 (18)° (N6-pyridine) but, the N4-pyridine ring is twisted out of the plane of the central triazine [dihedral angle = 19.76 (18)°].

The most prominent feature of the crystal packing is the formation of π···π interactions. These occur between the translationally related N1- and N4-pyridine rings with the separation between the ring centroids being 3.581 (2) Å for symmetry operation x - 1, y, z. These lead to the formation of supramolecular chains along the a axis. Chains assemble into layers that stack along the b-direction Fig. 3.

Related literature top

For related lead(II) complexes with the 2,4,6-tris(2-pyridyl)-1,3,5-triazine ligand, see: Harrowfield et al. (1996a,b, 2002).

Experimental top

The title complex was synthesized by the addition of 2,4,6-tris(2-pyridyl)-1,3,5-triazine (tptz; 0.312 g, 1 mmol) to a solution of lead(II) acetate trihydrate (0.378 g, 1 mmol) in 10 ml of DMF, followed by the drop wise addition of sodium azide (0.065 g, 1 mmol) dissolved in a minimum volume of water. After stirring for 2 h, the reaction solution was filtered. The resulting clear yellow solution left to stand in air. After 4 days, yellow prisms were obtained; Yield: 70%; M.pt. 540–542 K.

Structure description top

For related lead(II) complexes with the 2,4,6-tris(2-pyridyl)-1,3,5-triazine ligand, see: Harrowfield et al. (1996a,b, 2002).

Computing details top

Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO (Agilent, 2010); data reduction: CrysAlis PRO (Agilent, 2010); 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 molecular structure of (I) showing displacement ellipsoids at the 50% probability level. Unlabelled atoms are generated by the symmetry operation 1 - x, 1 - y, 1 - z.
	Fig. 2. Supramolecular chains in (I) mediated by π···π interactions shown as purple dashed lines.
	Fig. 3. A view of the unit-cell contents of (I) in projection down the a axis. The π···π interactions are shown as purple dashed lines.

Bis(µ-azido-κ²N¹:N¹)bis{(acetato- κ²O,O')[2,4,6-tris(2-pyridyl)-1,3,5-triazine- κ³N²,N¹,N⁶]lead(II)} top

Crystal data top

[Pb₂(C₂H₃O₂)₂(N₃)₂(C₁₈H₁₂N₆)₂]	Z = 1
M_r = 1241.22	F(000) = 592
Triclinic, P1	D_x = 2.081 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.5529 (4) Å	Cell parameters from 5891 reflections
b = 11.0080 (5) Å	θ = 2.6–29.2°
c = 11.8617 (5) Å	µ = 8.56 mm⁻¹
α = 86.739 (4)°	T = 100 K
β = 70.928 (4)°	Prism, yellow
γ = 70.100 (4)°	0.20 × 0.15 × 0.10 mm
V = 990.60 (8) Å³

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4358 independent reflections
Radiation source: SuperNova (Mo) X-ray Source	4046 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.059
Detector resolution: 10.4041 pixels mm^-1	θ_max = 27.5°, θ_min = 2.6°
ω scan	h = −10→9
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −13→10
T_min = 0.279, T_max = 0.482	l = −13→14
7814 measured reflections

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) = 0.049	H-atom parameters constrained
S = 0.97	w = 1/[σ²(F_o²) + (0.0106P)²] where P = (F_o² + 2F_c²)/3
4358 reflections	(Δ/σ)_max = 0.002
290 parameters	Δρ_max = 2.01 e Å⁻³
0 restraints	Δρ_min = −2.14 e Å⁻³

Crystal data top

[Pb₂(C₂H₃O₂)₂(N₃)₂(C₁₈H₁₂N₆)₂]	γ = 70.100 (4)°
M_r = 1241.22	V = 990.60 (8) Å³
Triclinic, P1	Z = 1
a = 8.5529 (4) Å	Mo Kα radiation
b = 11.0080 (5) Å	µ = 8.56 mm⁻¹
c = 11.8617 (5) Å	T = 100 K
α = 86.739 (4)°	0.20 × 0.15 × 0.10 mm
β = 70.928 (4)°

Data collection top

Agilent SuperNova Dual diffractometer with Atlas detector	4358 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	4046 reflections with I > 2σ(I)
T_min = 0.279, T_max = 0.482	R_int = 0.059
7814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.049	H-atom parameters constrained
S = 0.97	Δρ_max = 2.01 e Å⁻³
4358 reflections	Δρ_min = −2.14 e Å⁻³
290 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Pb	0.612101 (15)	0.416726 (12)	0.347893 (11)	0.01042 (5)
O1	0.5120 (3)	0.5621 (2)	0.2132 (2)	0.0151 (6)
O2	0.5432 (3)	0.6610 (2)	0.3570 (2)	0.0167 (6)
N1	0.4835 (3)	0.2650 (3)	0.2624 (3)	0.0128 (7)
N2	0.7962 (3)	0.2875 (3)	0.1327 (3)	0.0103 (6)
N3	0.8279 (4)	0.1391 (3)	−0.0182 (3)	0.0119 (6)
N4	1.0363 (4)	−0.0059 (3)	−0.2293 (3)	0.0149 (7)
N5	1.0514 (4)	0.2285 (3)	−0.0385 (3)	0.0129 (7)
N6	0.9239 (3)	0.4423 (3)	0.2205 (3)	0.0111 (6)
N7	0.2803 (4)	0.5086 (3)	0.4691 (3)	0.0162 (7)
N8	0.1867 (4)	0.6149 (3)	0.4603 (3)	0.0153 (7)
N9	0.0947 (4)	0.7192 (4)	0.4520 (3)	0.0276 (9)
C1	0.3281 (5)	0.2554 (4)	0.3282 (3)	0.0159 (8)
H1	0.2676	0.3031	0.4032	0.019*
C2	0.2523 (4)	0.1794 (4)	0.2918 (3)	0.0156 (8)
H2	0.1421	0.1750	0.3414	0.019*
C3	0.3376 (4)	0.1098 (4)	0.1829 (3)	0.0157 (8)
H3	0.2860	0.0586	0.1554	0.019*
C4	0.5005 (4)	0.1162 (4)	0.1146 (3)	0.0132 (8)
H4	0.5642	0.0678	0.0401	0.016*
C5	0.5687 (4)	0.1949 (3)	0.1572 (3)	0.0103 (7)
C6	0.7406 (4)	0.2074 (3)	0.0872 (3)	0.0104 (7)
C7	0.9812 (4)	0.1554 (3)	−0.0777 (3)	0.0105 (7)
C8	0.9539 (4)	0.2935 (3)	0.0672 (3)	0.0106 (7)
C9	1.1213 (4)	−0.0594 (4)	−0.3404 (4)	0.0200 (9)
H9	1.0950	−0.1299	−0.3625	0.024*
C10	1.2461 (5)	−0.0187 (4)	−0.4259 (3)	0.0211 (9)
H10	1.3009	−0.0591	−0.5043	0.025*
C11	1.2887 (5)	0.0824 (4)	−0.3942 (3)	0.0199 (9)
H11	1.3734	0.1128	−0.4502	0.024*
C12	1.2045 (4)	0.1380 (4)	−0.2787 (3)	0.0148 (8)
H12	1.2320	0.2062	−0.2533	0.018*
C13	1.0793 (4)	0.0921 (4)	−0.2008 (3)	0.0135 (8)
C14	1.0237 (4)	0.3786 (3)	0.1128 (3)	0.0108 (7)
C15	1.1825 (4)	0.3928 (4)	0.0472 (3)	0.0127 (8)
H15	1.2490	0.3480	−0.0287	0.015*
C16	1.2428 (5)	0.4728 (4)	0.0937 (3)	0.0154 (8)
H16	1.3515	0.4840	0.0502	0.018*
C17	1.1433 (4)	0.5364 (4)	0.2043 (3)	0.0152 (8)
H17	1.1832	0.5910	0.2387	0.018*
C18	0.9848 (4)	0.5194 (4)	0.2640 (3)	0.0138 (8)
H18	0.9158	0.5646	0.3394	0.017*
C19	0.4957 (4)	0.6651 (4)	0.2671 (3)	0.0145 (8)
C20	0.4162 (5)	0.7942 (4)	0.2216 (4)	0.0216 (9)
H20A	0.3924	0.7807	0.1488	0.032*
H20B	0.4985	0.8421	0.2038	0.032*
H20C	0.3059	0.8439	0.2827	0.032*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb	0.00968 (8)	0.01033 (8)	0.01004 (8)	−0.00308 (5)	−0.00182 (5)	−0.00064 (6)
O1	0.0109 (12)	0.0159 (15)	0.0157 (14)	−0.0040 (10)	−0.0009 (10)	−0.0023 (11)
O2	0.0180 (13)	0.0141 (15)	0.0211 (15)	−0.0073 (11)	−0.0089 (11)	0.0025 (12)
N1	0.0102 (14)	0.0105 (17)	0.0141 (16)	−0.0015 (12)	−0.0011 (12)	−0.0009 (13)
N2	0.0092 (14)	0.0108 (16)	0.0097 (15)	−0.0031 (12)	−0.0019 (12)	0.0003 (13)
N3	0.0117 (15)	0.0092 (16)	0.0134 (16)	−0.0021 (12)	−0.0036 (12)	−0.0010 (13)
N4	0.0108 (15)	0.0140 (18)	0.0178 (17)	−0.0007 (12)	−0.0048 (13)	−0.0039 (14)
N5	0.0117 (15)	0.0122 (17)	0.0123 (16)	−0.0030 (12)	−0.0019 (12)	−0.0003 (13)
N6	0.0089 (14)	0.0087 (16)	0.0123 (16)	−0.0008 (12)	−0.0013 (12)	−0.0013 (13)
N7	0.0136 (15)	0.0168 (19)	0.0169 (17)	−0.0053 (13)	−0.0032 (13)	0.0007 (14)
N8	0.0118 (15)	0.023 (2)	0.0099 (16)	−0.0070 (14)	0.0002 (12)	−0.0050 (14)
N9	0.0220 (18)	0.024 (2)	0.026 (2)	0.0037 (15)	−0.0051 (15)	−0.0040 (17)
C1	0.0147 (18)	0.016 (2)	0.0143 (19)	−0.0052 (15)	−0.0012 (15)	−0.0007 (16)
C2	0.0100 (17)	0.012 (2)	0.022 (2)	−0.0060 (14)	0.0004 (15)	0.0020 (16)
C3	0.0136 (18)	0.014 (2)	0.021 (2)	−0.0081 (15)	−0.0048 (15)	0.0011 (17)
C4	0.0141 (18)	0.012 (2)	0.0122 (19)	−0.0044 (14)	−0.0033 (15)	−0.0001 (15)
C5	0.0090 (16)	0.0063 (18)	0.0130 (18)	−0.0001 (13)	−0.0027 (14)	−0.0002 (15)
C6	0.0075 (16)	0.0062 (18)	0.0148 (19)	−0.0004 (13)	−0.0024 (14)	0.0024 (15)
C7	0.0057 (16)	0.0087 (19)	0.0138 (19)	0.0017 (13)	−0.0033 (14)	0.0009 (15)
C8	0.0100 (17)	0.0076 (19)	0.0124 (18)	−0.0001 (13)	−0.0044 (14)	0.0013 (15)
C9	0.0124 (18)	0.023 (2)	0.023 (2)	−0.0042 (16)	−0.0041 (16)	−0.0084 (18)
C10	0.0152 (19)	0.029 (3)	0.012 (2)	−0.0018 (17)	0.0005 (15)	−0.0078 (18)
C11	0.0139 (18)	0.026 (2)	0.014 (2)	−0.0057 (16)	0.0010 (15)	0.0007 (18)
C12	0.0119 (17)	0.012 (2)	0.016 (2)	−0.0013 (14)	−0.0021 (15)	−0.0034 (16)
C13	0.0089 (17)	0.012 (2)	0.0154 (19)	0.0011 (14)	−0.0024 (14)	−0.0025 (16)
C14	0.0104 (16)	0.0072 (18)	0.0120 (18)	0.0010 (13)	−0.0045 (14)	0.0010 (15)
C15	0.0098 (17)	0.014 (2)	0.0107 (18)	−0.0008 (14)	−0.0015 (14)	−0.0012 (15)
C16	0.0128 (18)	0.015 (2)	0.019 (2)	−0.0075 (15)	−0.0051 (15)	0.0063 (17)
C17	0.0136 (18)	0.016 (2)	0.020 (2)	−0.0092 (15)	−0.0069 (15)	0.0014 (16)
C18	0.0157 (18)	0.012 (2)	0.0123 (19)	−0.0037 (15)	−0.0041 (15)	0.0003 (15)
C19	0.0066 (16)	0.013 (2)	0.021 (2)	−0.0048 (14)	−0.0007 (15)	0.0016 (16)
C20	0.019 (2)	0.018 (2)	0.028 (2)	−0.0049 (16)	−0.0121 (17)	0.0085 (18)

Geometric parameters (Å, º) top

Pb—O1	2.349 (3)	C3—C4	1.388 (5)
Pb—O2	2.550 (3)	C3—H3	0.9500
Pb—N1	2.684 (3)	C4—C5	1.390 (5)
Pb—N2	2.698 (3)	C4—H4	0.9500
Pb—N6	2.702 (3)	C5—C6	1.483 (5)
Pb—N7	2.586 (3)	C7—C13	1.495 (5)
Pb—N7ⁱ	2.874 (3)	C8—C14	1.475 (5)
O1—C19	1.277 (4)	C9—C10	1.391 (5)
O2—C19	1.252 (4)	C9—H9	0.9500
N1—C1	1.339 (4)	C10—C11	1.388 (6)
N1—C5	1.347 (4)	C10—H10	0.9500
N2—C8	1.341 (4)	C11—C12	1.386 (5)
N2—C6	1.342 (5)	C11—H11	0.9500
N3—C7	1.338 (4)	C12—C13	1.387 (5)
N3—C6	1.341 (4)	C12—H12	0.9500
N4—C9	1.335 (5)	C14—C15	1.384 (5)
N4—C13	1.345 (5)	C15—C16	1.377 (5)
N5—C7	1.334 (5)	C15—H15	0.9500
N5—C8	1.339 (4)	C16—C17	1.380 (5)
N6—C18	1.335 (5)	C16—H16	0.9500
N6—C14	1.354 (4)	C17—C18	1.381 (5)
N7—N8	1.193 (4)	C17—H17	0.9500
N8—N9	1.170 (5)	C18—H18	0.9500
C1—C2	1.379 (5)	C19—C20	1.506 (5)
C1—H1	0.9500	C20—H20A	0.9800
C2—C3	1.380 (5)	C20—H20B	0.9800
C2—H2	0.9500	C20—H20C	0.9800

O1—Pb—O2	53.37 (9)	N3—C6—N2	124.8 (3)
O1—Pb—N7	80.25 (9)	N3—C6—C5	117.3 (3)
O2—Pb—N7	76.00 (9)	N2—C6—C5	117.8 (3)
O1—Pb—N1	83.67 (9)	N5—C7—N3	125.3 (3)
O2—Pb—N1	132.61 (8)	N5—C7—C13	116.6 (3)
N7—Pb—N1	78.04 (9)	N3—C7—C13	118.1 (3)
O1—Pb—N2	76.16 (9)	N2—C8—N5	124.0 (3)
O2—Pb—N2	117.28 (9)	N2—C8—C14	118.3 (3)
N7—Pb—N2	133.65 (9)	N5—C8—C14	117.7 (3)
N1—Pb—N2	60.27 (8)	N4—C9—C10	124.2 (4)
O1—Pb—N6	82.58 (8)	N4—C9—H9	117.9
O2—Pb—N6	76.90 (8)	C10—C9—H9	117.9
N7—Pb—N6	152.86 (10)	C11—C10—C9	118.5 (3)
N1—Pb—N6	120.73 (8)	C11—C10—H10	120.7
N2—Pb—N6	60.46 (9)	C9—C10—H10	120.7
O1—Pb—C19	26.90 (10)	C12—C11—C10	118.3 (4)
O2—Pb—C19	26.52 (9)	C12—C11—H11	120.9
N7—Pb—C19	75.47 (10)	C10—C11—H11	120.9
N1—Pb—C19	108.20 (10)	C11—C12—C13	118.8 (4)
N2—Pb—C19	97.94 (10)	C11—C12—H12	120.6
N6—Pb—C19	79.70 (9)	C13—C12—H12	120.6
C19—O1—Pb	96.8 (2)	N4—C13—C12	124.0 (3)
C19—O2—Pb	88.1 (2)	N4—C13—C7	116.6 (3)
C1—N1—C5	117.7 (3)	C12—C13—C7	119.4 (3)
C1—N1—Pb	118.8 (2)	N6—C14—C15	122.3 (3)
C5—N1—Pb	123.5 (2)	N6—C14—C8	116.7 (3)
C8—N2—C6	115.6 (3)	C15—C14—C8	121.0 (3)
C8—N2—Pb	122.1 (2)	C16—C15—C14	119.0 (3)
C6—N2—Pb	122.2 (2)	C16—C15—H15	120.5
C7—N3—C6	114.6 (3)	C14—C15—H15	120.5
C9—N4—C13	116.2 (3)	C17—C16—C15	119.1 (3)
C7—N5—C8	115.6 (3)	C17—C16—H16	120.4
C18—N6—C14	117.7 (3)	C15—C16—H16	120.4
C18—N6—Pb	119.9 (2)	C16—C17—C18	118.8 (3)
C14—N6—Pb	122.4 (2)	C16—C17—H17	120.6
N8—N7—Pb	123.7 (2)	C18—C17—H17	120.6
N9—N8—N7	179.9 (5)	N6—C18—C17	123.0 (3)
N1—C1—C2	122.9 (3)	N6—C18—H18	118.5
N1—C1—H1	118.6	C17—C18—H18	118.5
C2—C1—H1	118.6	O2—C19—O1	121.5 (3)
C1—C2—C3	119.6 (3)	O2—C19—C20	119.5 (3)
C1—C2—H2	120.2	O1—C19—C20	119.0 (3)
C3—C2—H2	120.2	O2—C19—Pb	65.4 (2)
C2—C3—C4	118.4 (3)	O1—C19—Pb	56.31 (19)
C2—C3—H3	120.8	C20—C19—Pb	173.3 (3)
C4—C3—H3	120.8	C19—C20—H20A	109.5
C3—C4—C5	118.7 (3)	C19—C20—H20B	109.5
C3—C4—H4	120.6	H20A—C20—H20B	109.5
C5—C4—H4	120.6	C19—C20—H20C	109.5
N1—C5—C4	122.8 (3)	H20A—C20—H20C	109.5
N1—C5—C6	116.1 (3)	H20B—C20—H20C	109.5
C4—C5—C6	121.1 (3)

O2—Pb—O1—C19	−2.67 (18)	C3—C4—C5—C6	−178.9 (3)
N7—Pb—O1—C19	77.06 (19)	C7—N3—C6—N2	0.5 (5)
N1—Pb—O1—C19	155.96 (19)	C7—N3—C6—C5	179.3 (3)
N2—Pb—O1—C19	−143.2 (2)	C8—N2—C6—N3	−2.4 (5)
N6—Pb—O1—C19	−81.84 (19)	Pb—N2—C6—N3	−178.8 (3)
O1—Pb—O2—C19	2.71 (18)	C8—N2—C6—C5	178.8 (3)
N7—Pb—O2—C19	−85.5 (2)	Pb—N2—C6—C5	2.3 (4)
N1—Pb—O2—C19	−26.8 (2)	N1—C5—C6—N3	−179.7 (3)
N2—Pb—O2—C19	46.8 (2)	C4—C5—C6—N3	−0.5 (5)
N6—Pb—O2—C19	93.2 (2)	N1—C5—C6—N2	−0.7 (5)
O1—Pb—N1—C1	−102.3 (3)	C4—C5—C6—N2	178.5 (3)
O2—Pb—N1—C1	−78.9 (3)	C8—N5—C7—N3	−2.8 (5)
N7—Pb—N1—C1	−20.9 (3)	C8—N5—C7—C13	174.2 (3)
N2—Pb—N1—C1	−179.9 (3)	C6—N3—C7—N5	2.3 (5)
N6—Pb—N1—C1	−179.7 (2)	C6—N3—C7—C13	−174.7 (3)
C19—Pb—N1—C1	−91.1 (3)	C6—N2—C8—N5	1.8 (5)
O1—Pb—N1—C5	79.2 (3)	Pb—N2—C8—N5	178.3 (3)
O2—Pb—N1—C5	102.6 (3)	C6—N2—C8—C14	−179.3 (3)
N7—Pb—N1—C5	160.6 (3)	Pb—N2—C8—C14	−2.8 (4)
N2—Pb—N1—C5	1.6 (3)	C7—N5—C8—N2	0.6 (5)
N6—Pb—N1—C5	1.8 (3)	C7—N5—C8—C14	−178.3 (3)
C19—Pb—N1—C5	90.4 (3)	C13—N4—C9—C10	−1.1 (6)
O1—Pb—N2—C8	91.2 (3)	N4—C9—C10—C11	1.3 (6)
O2—Pb—N2—C8	56.1 (3)	C9—C10—C11—C12	−0.1 (6)
N7—Pb—N2—C8	152.8 (2)	C10—C11—C12—C13	−1.2 (6)
N1—Pb—N2—C8	−178.2 (3)	C9—N4—C13—C12	−0.3 (5)
N6—Pb—N2—C8	2.0 (2)	C9—N4—C13—C7	178.3 (3)
C19—Pb—N2—C8	75.3 (3)	C11—C12—C13—N4	1.5 (6)
O1—Pb—N2—C6	−92.5 (3)	C11—C12—C13—C7	−177.0 (3)
O2—Pb—N2—C6	−127.6 (3)	N5—C7—C13—N4	163.6 (3)
N7—Pb—N2—C6	−31.0 (3)	N3—C7—C13—N4	−19.2 (5)
N1—Pb—N2—C6	−2.0 (3)	N5—C7—C13—C12	−17.7 (5)
N6—Pb—N2—C6	178.2 (3)	N3—C7—C13—C12	159.5 (3)
C19—Pb—N2—C6	−108.4 (3)	C18—N6—C14—C15	−1.0 (5)
O1—Pb—N6—C18	101.2 (3)	Pb—N6—C14—C15	179.4 (3)
O2—Pb—N6—C18	47.2 (3)	C18—N6—C14—C8	179.7 (3)
N7—Pb—N6—C18	50.1 (4)	Pb—N6—C14—C8	0.1 (4)
N1—Pb—N6—C18	179.2 (2)	N2—C8—C14—N6	1.8 (5)
N2—Pb—N6—C18	179.4 (3)	N5—C8—C14—N6	−179.2 (3)
C19—Pb—N6—C18	74.1 (3)	N2—C8—C14—C15	−177.5 (3)
O1—Pb—N6—C14	−79.2 (3)	N5—C8—C14—C15	1.4 (5)
O2—Pb—N6—C14	−133.2 (3)	N6—C14—C15—C16	1.0 (5)
N7—Pb—N6—C14	−130.3 (3)	C8—C14—C15—C16	−179.7 (3)
N1—Pb—N6—C14	−1.2 (3)	C14—C15—C16—C17	0.0 (6)
N2—Pb—N6—C14	−1.0 (2)	C15—C16—C17—C18	−1.0 (6)
C19—Pb—N6—C14	−106.3 (3)	C14—N6—C18—C17	−0.1 (5)
O1—Pb—N7—N8	−28.8 (3)	Pb—N6—C18—C17	179.6 (3)
O2—Pb—N7—N8	25.6 (3)	C16—C17—C18—N6	1.1 (6)
N1—Pb—N7—N8	−114.4 (3)	Pb—O2—C19—O1	−4.7 (3)
N2—Pb—N7—N8	−88.9 (3)	Pb—O2—C19—C20	174.9 (3)
N6—Pb—N7—N8	22.7 (4)	Pb—O1—C19—O2	5.1 (3)
C19—Pb—N7—N8	−1.7 (3)	Pb—O1—C19—C20	−174.4 (3)
C5—N1—C1—C2	−1.1 (5)	O1—Pb—C19—O2	−175.2 (3)
Pb—N1—C1—C2	−179.7 (3)	N7—Pb—C19—O2	87.7 (2)
N1—C1—C2—C3	−0.3 (6)	N1—Pb—C19—O2	159.58 (18)
C1—C2—C3—C4	1.6 (6)	N2—Pb—C19—O2	−139.18 (19)
C2—C3—C4—C5	−1.6 (5)	N6—Pb—C19—O2	−81.28 (19)
C1—N1—C5—C4	1.1 (5)	O2—Pb—C19—O1	175.2 (3)
Pb—N1—C5—C4	179.6 (3)	N7—Pb—C19—O1	−97.13 (19)
C1—N1—C5—C6	−179.7 (3)	N1—Pb—C19—O1	−25.2 (2)
Pb—N1—C5—C6	−1.2 (4)	N2—Pb—C19—O1	36.01 (19)
C3—C4—C5—N1	0.2 (6)	N6—Pb—C19—O1	93.91 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Pb₂(C₂H₃O₂)₂(N₃)₂(C₁₈H₁₂N₆)₂]
M_r	1241.22
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	8.5529 (4), 11.0080 (5), 11.8617 (5)
α, β, γ (°)	86.739 (4), 70.928 (4), 70.100 (4)
V (Å³)	990.60 (8)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	8.56
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2010)
T_min, T_max	0.279, 0.482
No. of measured, independent and observed [I > 2σ(I)] reflections	7814, 4358, 4046
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.049, 0.97
No. of reflections	4358
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	2.01, −2.14

Computer programs: CrysAlis PRO (Agilent, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Pb—O1	2.349 (3)	Pb—N6	2.702 (3)
Pb—O2	2.550 (3)	Pb—N7	2.586 (3)
Pb—N1	2.684 (3)	Pb—N7ⁱ	2.874 (3)
Pb—N2	2.698 (3)

Symmetry code: (i) −x+1, −y+1, −z+1.

Footnotes

‡Additional correspondence author, e-mail: akbarghaemi@yahoo.com.

Acknowledgements

We acknowledge financial support of this work by the Islamic Azad University, Saveh Branch, and thank the University of Malaya for supporting the crystallographic facility.

References

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