Bis(μ-N-nitroso-N-phenyl­hydroxy­laminato)-κ3O,O′:O′;κ3O′:O,O′-bis­[(N-nitroso-N-phenyl­hydroxy­laminato-κ2O,O′)lead(II)]

Najafi, E.; Amini, M.M.; Ng, S.W.

doi:10.1107/S1600536811006775

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m377

doi:10.1107/S1600536811006775

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Bis(μ-N-nitroso-N-phenylhydroxylaminato)-κ³O,O′:O′;κ³O′:O,O′-bis[(N-nitroso-N-phenylhydroxylaminato-κ²O,O′)lead(II)]

Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 February 2011; accepted 22 February 2011; online 26 February 2011)

The four cupferronate ions in the dinuclear title compound, [Pb₂(C₆H₅N₂O₂)₄], O,O′-chelate to the two Pb^II atoms; two of the four nitroso O atoms are also involved in bridging. The geometry of both five-coordinate Pb^IIatoms is distorted Ψ-octahedral; if another two longer intermolecular Pb⋯O interactions [at 2.955 (1) and 3.099 (1) Å] are considered, the geometry is a distorted Ψ-square antiprism.

Related literature

For the spectrospic assigment of the structure of the lead derivative, see: Bottei & Schneggenburger (1970 ). For the structure of the organic ligand, see: Hickmann et al. (1979 ).

Experimental

Crystal data

[Pb₂(C₆H₅N₂O₂)₄]
M_r = 962.86
Triclinic, $[P \overline 1]$
a = 9.6149 (5) Å
b = 11.5340 (6) Å
c = 13.2724 (7) Å
α = 82.459 (1)°
β = 79.280 (1)°
γ = 67.369 (1)°
V = 1331.95 (12) Å³
Z = 2
Mo Kα radiation
μ = 12.69 mm⁻¹
T = 100 K
0.30 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.115, T_max = 0.252
16878 measured reflections
6094 independent reflections
5444 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.026
wR(F²) = 0.071
S = 1.06
6094 reflections
379 parameters
H-atom parameters constrained
Δρ_max = 1.74 e Å⁻³
Δρ_min = −2.24 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811006775/bt5480sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006775/bt5480Isup2.hkl

checkCIF report

Comment top

The cupferronate ion is a common ion used for the complexation of metals; the crystal structure of the chelate has been reported (Hickmann et al., 1979). The synthesis of the lead(II) derivative has been known for a long time (Bottei & Schneggenburger, 1970), and the compound was assumed to exist as a mononuclear compound. The compound is, in fact, a dinuclear compound (Scheme I). The four cupferronate ions in dinuclear [Pb(C₆H₅N₂O₂)₂]₂ O,O'-chelate to the lead(II) atom; two of the four nitroso O atoms are also involved in bridging (Fig. 1). The geometry of both five-coordinate lead atoms is Ψ-octahedral; if another longer intermolecular Pb···O interactions (approx. 3.0 Å) are considered, the geometry is a Ψ-square-antiprism (Fig. 2).

Related literature top

For the spectrospic assigment of the structure of the lead derivative, see: Bottei & Schneggenburger (1970). For the structure of the organic ligand, see: Hickmann et al. (1979).

Experimental top

Lead(II) nitrate (0.33 g, 1 mmol) dissolved in ethanol (20 ml) was added to the cupferron ligand (0.31 g, 2 mmol) dissolved in ethanol (20 ml). The mixture was stirred and then set aside for the growth of brown colored crystals.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of Pb₂(C₆H₅N₂O₂)₄ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.
	Fig. 2. Detail of geometry of the lead atoms when intermolecular longer interactions are considered. Symmetry codes: (i) 1 - x, 1 - y, 1 - z; (ii) 2 - x, 1 - y, 1 - z.

Bis(µ-N-nitroso-N-phenylhydroxylaminato)- κ³O,O':O';κ³O':O,O'- bis[(N-nitroso-N-phenylhydroxylaminato- κ²O,O')lead(II)] top

Crystal data top

[Pb₂(C₆H₅N₂O₂)₄]	Z = 2
M_r = 962.86	F(000) = 896
Triclinic, P1	D_x = 2.401 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.6149 (5) Å	Cell parameters from 9907 reflections
b = 11.5340 (6) Å	θ = 2.4–28.3°
c = 13.2724 (7) Å	µ = 12.69 mm⁻¹
α = 82.459 (1)°	T = 100 K
β = 79.280 (1)°	Prism, brown
γ = 67.369 (1)°	0.30 × 0.15 × 0.15 mm
V = 1331.95 (12) Å³

Data collection top

Bruker SMART APEX diffractometer	6094 independent reflections
Radiation source: fine-focus sealed tube	5444 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.5°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.115, T_max = 0.252	k = −14→14
16878 measured reflections	l = −17→17

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)] = 0.026	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.071	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0339P)² + 2.8506P] where P = (F_o² + 2F_c²)/3
6094 reflections	(Δ/σ)_max = 0.001
379 parameters	Δρ_max = 1.74 e Å⁻³
0 restraints	Δρ_min = −2.24 e Å⁻³

Crystal data top

[Pb₂(C₆H₅N₂O₂)₄]	γ = 67.369 (1)°
M_r = 962.86	V = 1331.95 (12) Å³
Triclinic, P1	Z = 2
a = 9.6149 (5) Å	Mo Kα radiation
b = 11.5340 (6) Å	µ = 12.69 mm⁻¹
c = 13.2724 (7) Å	T = 100 K
α = 82.459 (1)°	0.30 × 0.15 × 0.15 mm
β = 79.280 (1)°

Data collection top

Bruker SMART APEX diffractometer	6094 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5444 reflections with I > 2σ(I)
T_min = 0.115, T_max = 0.252	R_int = 0.036
16878 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.026	0 restraints
wR(F²) = 0.071	H-atom parameters constrained
S = 1.06	Δρ_max = 1.74 e Å⁻³
6094 reflections	Δρ_min = −2.24 e Å⁻³
379 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Pb1	0.634932 (18)	0.462439 (15)	0.364998 (12)	0.00867 (6)
Pb2	0.819969 (18)	0.523384 (15)	0.612158 (13)	0.01006 (6)
O1	0.6060 (4)	0.6161 (3)	0.4843 (2)	0.0123 (7)
O2	0.5388 (4)	0.6773 (3)	0.3020 (2)	0.0121 (7)
O3	0.8865 (4)	0.4622 (3)	0.3460 (3)	0.0151 (7)
O4	0.7942 (4)	0.3974 (3)	0.2021 (3)	0.0120 (7)
O5	0.7358 (4)	0.3785 (3)	0.5523 (3)	0.0143 (7)
O6	1.0141 (4)	0.3240 (3)	0.5670 (3)	0.0134 (7)
O7	0.5918 (4)	0.5665 (3)	0.7423 (3)	0.0163 (7)
O8	0.8387 (4)	0.3773 (3)	0.7572 (3)	0.0131 (7)
N1	0.5102 (4)	0.7608 (4)	0.3685 (3)	0.0105 (8)
N2	0.5430 (5)	0.7366 (4)	0.4610 (3)	0.0135 (8)
N3	0.9326 (4)	0.3966 (4)	0.1922 (3)	0.0083 (7)
N4	0.9843 (5)	0.4281 (4)	0.2626 (3)	0.0125 (8)
N5	0.9547 (5)	0.2375 (4)	0.5810 (3)	0.0113 (8)
N6	0.8147 (4)	0.2585 (4)	0.5742 (3)	0.0124 (8)
N7	0.7129 (4)	0.3892 (4)	0.8210 (3)	0.0108 (8)
N8	0.5862 (5)	0.4818 (4)	0.8174 (3)	0.0160 (9)
C1	0.4389 (5)	0.8924 (4)	0.3363 (4)	0.0100 (9)
C2	0.3808 (5)	0.9821 (5)	0.4097 (4)	0.0135 (9)
H2	0.3868	0.9575	0.4804	0.016*
C3	0.3142 (6)	1.1081 (5)	0.3774 (4)	0.0155 (10)
H3	0.2736	1.1703	0.4264	0.019*
C4	0.3064 (6)	1.1439 (5)	0.2730 (4)	0.0160 (10)
H4	0.2630	1.2304	0.2509	0.019*
C5	0.3626 (6)	1.0524 (5)	0.2020 (4)	0.0154 (10)
H5	0.3563	1.0766	0.1313	0.018*
C6	0.4280 (5)	0.9255 (4)	0.2332 (4)	0.0116 (9)
H6	0.4644	0.8630	0.1846	0.014*
C7	1.0322 (5)	0.3611 (4)	0.0962 (3)	0.0093 (9)
C8	1.1523 (5)	0.4028 (5)	0.0675 (4)	0.0142 (10)
H8	1.1735	0.4506	0.1116	0.017*
C9	1.2405 (6)	0.3726 (5)	−0.0276 (4)	0.0208 (11)
H9	1.3242	0.3991	−0.0488	0.025*
C10	1.2081 (6)	0.3047 (5)	−0.0917 (4)	0.0173 (10)
H10	1.2680	0.2866	−0.1573	0.021*
C11	1.0883 (6)	0.2625 (5)	−0.0609 (4)	0.0179 (10)
H11	1.0678	0.2140	−0.1047	0.021*
C12	0.9989 (5)	0.2915 (4)	0.0341 (4)	0.0130 (9)
H12	0.9163	0.2638	0.0558	0.016*
C13	1.0454 (5)	0.1123 (4)	0.6183 (4)	0.0114 (9)
C14	0.9955 (6)	0.0140 (5)	0.6234 (4)	0.0156 (10)
H14	0.9035	0.0261	0.5994	0.019*
C15	1.0836 (6)	−0.1037 (5)	0.6649 (4)	0.0160 (10)
H15	1.0517	−0.1728	0.6689	0.019*
C16	1.2180 (6)	−0.1200 (5)	0.7002 (4)	0.0164 (10)
H16	1.2769	−0.2001	0.7287	0.020*
C17	1.2661 (6)	−0.0205 (5)	0.6942 (4)	0.0147 (10)
H17	1.3585	−0.0326	0.7179	0.018*
C18	1.1794 (5)	0.0983 (5)	0.6533 (4)	0.0123 (9)
H18	1.2110	0.1675	0.6495	0.015*
C19	0.7167 (5)	0.2865 (4)	0.8969 (4)	0.0102 (9)
C20	0.6247 (6)	0.3103 (5)	0.9917 (4)	0.0151 (10)
H20	0.5615	0.3939	1.0083	0.018*
C21	0.6273 (6)	0.2085 (5)	1.0620 (4)	0.0191 (11)
H21	0.5645	0.2225	1.1270	0.023*
C22	0.7215 (6)	0.0868 (5)	1.0372 (4)	0.0217 (11)
H22	0.7216	0.0175	1.0847	0.026*
C23	0.8148 (6)	0.0666 (5)	0.9434 (4)	0.0180 (10)
H23	0.8806	−0.0166	0.9275	0.022*
C24	0.8139 (6)	0.1657 (5)	0.8724 (4)	0.0151 (10)
H24	0.8785	0.1515	0.8081	0.018*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.00879 (9)	0.01181 (9)	0.00641 (9)	−0.00508 (7)	−0.00091 (6)	−0.00028 (6)
Pb2	0.01043 (9)	0.01290 (10)	0.00908 (10)	−0.00683 (7)	−0.00345 (7)	0.00231 (7)
O1	0.0151 (17)	0.0133 (16)	0.0089 (16)	−0.0059 (14)	−0.0030 (13)	0.0017 (13)
O2	0.0169 (17)	0.0132 (16)	0.0069 (15)	−0.0060 (13)	−0.0007 (13)	−0.0032 (13)
O3	0.0140 (17)	0.0257 (19)	0.0091 (16)	−0.0100 (15)	−0.0017 (13)	−0.0051 (14)
O4	0.0080 (15)	0.0203 (17)	0.0103 (16)	−0.0077 (13)	−0.0027 (12)	−0.0005 (13)
O5	0.0142 (17)	0.0167 (17)	0.0143 (17)	−0.0077 (14)	−0.0058 (14)	0.0022 (14)
O6	0.0122 (16)	0.0150 (16)	0.0155 (17)	−0.0084 (13)	−0.0013 (13)	0.0009 (13)
O7	0.0172 (18)	0.0186 (18)	0.0096 (17)	−0.0051 (14)	0.0011 (14)	0.0016 (14)
O8	0.0081 (15)	0.0190 (17)	0.0104 (16)	−0.0053 (13)	0.0017 (12)	0.0015 (13)
N1	0.0095 (18)	0.0153 (19)	0.0080 (19)	−0.0064 (16)	−0.0009 (15)	−0.0004 (15)
N2	0.013 (2)	0.014 (2)	0.013 (2)	−0.0046 (16)	−0.0042 (16)	0.0004 (16)
N3	0.0049 (17)	0.0130 (18)	0.0070 (18)	−0.0045 (15)	0.0010 (14)	0.0004 (15)
N4	0.0120 (19)	0.022 (2)	0.0062 (19)	−0.0099 (17)	−0.0033 (15)	0.0020 (16)
N5	0.0138 (19)	0.016 (2)	0.0060 (18)	−0.0087 (16)	−0.0020 (15)	0.0022 (15)
N6	0.0101 (19)	0.015 (2)	0.014 (2)	−0.0058 (16)	−0.0024 (15)	−0.0025 (16)
N7	0.0113 (19)	0.0161 (19)	0.0047 (18)	−0.0047 (16)	−0.0021 (14)	0.0000 (15)
N8	0.019 (2)	0.019 (2)	0.0083 (19)	−0.0047 (17)	−0.0031 (16)	0.0006 (16)
C1	0.007 (2)	0.013 (2)	0.011 (2)	−0.0056 (17)	−0.0005 (17)	0.0002 (17)
C2	0.012 (2)	0.019 (2)	0.010 (2)	−0.0079 (19)	0.0031 (18)	−0.0032 (18)
C3	0.014 (2)	0.017 (2)	0.016 (2)	−0.0059 (19)	−0.0004 (19)	−0.006 (2)
C4	0.014 (2)	0.015 (2)	0.022 (3)	−0.0094 (19)	−0.008 (2)	0.006 (2)
C5	0.017 (2)	0.022 (3)	0.009 (2)	−0.008 (2)	−0.0055 (18)	0.0035 (19)
C6	0.011 (2)	0.013 (2)	0.012 (2)	−0.0057 (18)	−0.0021 (18)	−0.0023 (18)
C7	0.010 (2)	0.008 (2)	0.007 (2)	−0.0012 (17)	0.0019 (17)	−0.0004 (16)
C8	0.010 (2)	0.018 (2)	0.016 (2)	−0.0072 (19)	−0.0045 (18)	0.0034 (19)
C9	0.010 (2)	0.027 (3)	0.024 (3)	−0.008 (2)	−0.004 (2)	0.008 (2)
C10	0.015 (2)	0.018 (2)	0.014 (2)	−0.003 (2)	0.0000 (19)	0.001 (2)
C11	0.013 (2)	0.022 (3)	0.017 (3)	−0.003 (2)	−0.0014 (19)	−0.004 (2)
C12	0.010 (2)	0.016 (2)	0.014 (2)	−0.0075 (18)	0.0027 (18)	0.0010 (18)
C13	0.011 (2)	0.013 (2)	0.008 (2)	−0.0029 (18)	0.0016 (17)	−0.0024 (17)
C14	0.015 (2)	0.022 (3)	0.012 (2)	−0.008 (2)	−0.0017 (19)	−0.0048 (19)
C15	0.019 (2)	0.017 (2)	0.017 (2)	−0.011 (2)	−0.003 (2)	−0.0024 (19)
C16	0.014 (2)	0.021 (3)	0.015 (2)	−0.008 (2)	−0.0030 (19)	0.001 (2)
C17	0.013 (2)	0.024 (3)	0.010 (2)	−0.010 (2)	−0.0018 (18)	0.0005 (19)
C18	0.010 (2)	0.019 (2)	0.012 (2)	−0.0111 (19)	0.0003 (18)	−0.0008 (19)
C19	0.011 (2)	0.016 (2)	0.008 (2)	−0.0091 (18)	−0.0026 (17)	−0.0006 (18)
C20	0.015 (2)	0.022 (3)	0.009 (2)	−0.008 (2)	−0.0026 (18)	−0.0011 (19)
C21	0.013 (2)	0.029 (3)	0.015 (3)	−0.010 (2)	0.0030 (19)	0.003 (2)
C22	0.028 (3)	0.019 (3)	0.021 (3)	−0.015 (2)	−0.006 (2)	0.008 (2)
C23	0.024 (3)	0.014 (2)	0.017 (3)	−0.007 (2)	−0.003 (2)	−0.0024 (19)
C24	0.017 (2)	0.021 (2)	0.010 (2)	−0.010 (2)	−0.0013 (19)	−0.0040 (19)

Geometric parameters (Å, º) top

Pb1—O2	2.382 (3)	C5—H5	0.9500
Pb1—O3	2.384 (3)	C6—H6	0.9500
Pb1—O4	2.427 (3)	C7—C12	1.378 (7)
Pb1—O1	2.433 (3)	C7—C8	1.388 (7)
Pb1—O5	2.757 (3)	C8—C9	1.387 (7)
Pb2—O8	2.371 (3)	C8—H8	0.9500
Pb2—O5	2.389 (3)	C9—C10	1.376 (8)
Pb2—O6	2.403 (3)	C9—H9	0.9500
Pb2—O7	2.453 (3)	C10—C11	1.392 (7)
Pb2—O1	2.718 (3)	C10—H10	0.9500
O1—N2	1.305 (5)	C11—C12	1.387 (7)
O2—N1	1.309 (5)	C11—H11	0.9500
O3—N4	1.307 (5)	C12—H12	0.9500
O4—N3	1.310 (5)	C13—C14	1.380 (7)
O5—N6	1.320 (5)	C13—C18	1.394 (7)
O6—N5	1.307 (5)	C14—C15	1.399 (7)
O7—N8	1.311 (5)	C14—H14	0.9500
O8—N7	1.312 (5)	C15—C16	1.393 (7)
N1—N2	1.293 (6)	C15—H15	0.9500
N1—C1	1.447 (6)	C16—C17	1.382 (7)
N3—N4	1.286 (6)	C16—H16	0.9500
N3—C7	1.445 (6)	C17—C18	1.400 (7)
N5—N6	1.291 (6)	C17—H17	0.9500
N5—C13	1.447 (6)	C18—H18	0.9500
N7—N8	1.278 (6)	C19—C24	1.387 (7)
N7—C19	1.444 (6)	C19—C20	1.390 (7)
C1—C6	1.383 (7)	C20—C21	1.396 (7)
C1—C2	1.396 (7)	C20—H20	0.9500
C2—C3	1.388 (7)	C21—C22	1.390 (8)
C2—H2	0.9500	C21—H21	0.9500
C3—C4	1.400 (7)	C22—C23	1.382 (8)
C3—H3	0.9500	C22—H22	0.9500
C4—C5	1.388 (7)	C23—C24	1.381 (7)
C4—H4	0.9500	C23—H23	0.9500
C5—C6	1.392 (7)	C24—H24	0.9500

O2—Pb1—O3	91.40 (12)	C4—C5—C6	120.8 (4)
O2—Pb1—O4	92.26 (11)	C4—C5—H5	119.6
O3—Pb1—O4	64.06 (11)	C6—C5—H5	119.6
O2—Pb1—O1	64.21 (11)	C1—C6—C5	118.7 (4)
O3—Pb1—O1	77.66 (11)	C1—C6—H6	120.6
O4—Pb1—O1	134.66 (11)	C5—C6—H6	120.6
O2—Pb1—O5	125.02 (11)	C12—C7—C8	122.4 (4)
O3—Pb1—O5	72.98 (11)	C12—C7—N3	118.0 (4)
O4—Pb1—O5	123.21 (10)	C8—C7—N3	119.5 (4)
O1—Pb1—O5	61.03 (10)	C9—C8—C7	117.9 (5)
O8—Pb2—O5	79.95 (12)	C9—C8—H8	121.0
O8—Pb2—O6	70.65 (11)	C7—C8—H8	121.0
O5—Pb2—O6	64.08 (11)	C10—C9—C8	120.8 (5)
O8—Pb2—O7	63.85 (11)	C10—C9—H9	119.6
O5—Pb2—O7	85.48 (12)	C8—C9—H9	119.6
O6—Pb2—O7	128.79 (11)	C9—C10—C11	120.4 (5)
O8—Pb2—O1	130.44 (11)	C9—C10—H10	119.8
O5—Pb2—O1	62.13 (11)	C11—C10—H10	119.8
O6—Pb2—O1	113.71 (11)	C12—C11—C10	119.7 (5)
O7—Pb2—O1	81.54 (11)	C12—C11—H11	120.1
N2—O1—Pb1	121.0 (3)	C10—C11—H11	120.1
N2—O1—Pb2	121.7 (3)	C7—C12—C11	118.8 (4)
Pb1—O1—Pb2	111.54 (12)	C7—C12—H12	120.6
N1—O2—Pb1	116.1 (3)	C11—C12—H12	120.6
N4—O3—Pb1	122.2 (3)	C14—C13—C18	122.3 (5)
N3—O4—Pb1	115.8 (3)	C14—C13—N5	120.7 (4)
N6—O5—Pb2	115.1 (3)	C18—C13—N5	116.9 (4)
N6—O5—Pb1	121.7 (3)	C13—C14—C15	118.5 (5)
Pb2—O5—Pb1	111.59 (12)	C13—C14—H14	120.8
N5—O6—Pb2	109.6 (3)	C15—C14—H14	120.8
N8—O7—Pb2	119.6 (3)	C16—C15—C14	120.2 (5)
N7—O8—Pb2	117.1 (3)	C16—C15—H15	119.9
N2—N1—O2	125.6 (4)	C14—C15—H15	119.9
N2—N1—C1	116.3 (4)	C17—C16—C15	120.4 (5)
O2—N1—C1	118.0 (4)	C17—C16—H16	119.8
N1—N2—O1	112.5 (4)	C15—C16—H16	119.8
N4—N3—O4	123.6 (4)	C16—C17—C18	120.2 (5)
N4—N3—C7	117.9 (4)	C16—C17—H17	119.9
O4—N3—C7	118.5 (4)	C18—C17—H17	119.9
N3—N4—O3	114.4 (4)	C13—C18—C17	118.3 (5)
N6—N5—O6	124.4 (4)	C13—C18—H18	120.9
N6—N5—C13	116.9 (4)	C17—C18—H18	120.9
O6—N5—C13	118.3 (4)	C24—C19—C20	121.8 (5)
N5—N6—O5	112.6 (4)	C24—C19—N7	118.3 (4)
N8—N7—O8	124.7 (4)	C20—C19—N7	119.9 (4)
N8—N7—C19	118.0 (4)	C19—C20—C21	118.5 (5)
O8—N7—C19	117.1 (4)	C19—C20—H20	120.8
N7—N8—O7	113.5 (4)	C21—C20—H20	120.8
C6—C1—C2	121.7 (4)	C22—C21—C20	120.2 (5)
C6—C1—N1	118.8 (4)	C22—C21—H21	119.9
C2—C1—N1	119.5 (4)	C20—C21—H21	119.9
C3—C2—C1	118.8 (5)	C23—C22—C21	119.9 (5)
C3—C2—H2	120.6	C23—C22—H22	120.0
C1—C2—H2	120.6	C21—C22—H22	120.0
C2—C3—C4	120.4 (5)	C24—C23—C22	121.0 (5)
C2—C3—H3	119.8	C24—C23—H23	119.5
C4—C3—H3	119.8	C22—C23—H23	119.5
C5—C4—C3	119.6 (5)	C23—C24—C19	118.6 (5)
C5—C4—H4	120.2	C23—C24—H24	120.7
C3—C4—H4	120.2	C19—C24—H24	120.7

O2—Pb1—O1—N2	5.5 (3)	Pb1—O4—N3—C7	−178.8 (3)
O3—Pb1—O1—N2	103.2 (3)	O4—N3—N4—O3	−0.4 (6)
O4—Pb1—O1—N2	71.0 (4)	C7—N3—N4—O3	178.2 (4)
O5—Pb1—O1—N2	−179.6 (3)	Pb1—O3—N4—N3	0.8 (5)
O2—Pb1—O1—Pb2	−148.12 (16)	Pb2—O6—N5—N6	28.7 (5)
O3—Pb1—O1—Pb2	−50.45 (13)	Pb2—O6—N5—C13	−143.8 (3)
O4—Pb1—O1—Pb2	−82.70 (17)	O6—N5—N6—O5	−0.8 (6)
O5—Pb1—O1—Pb2	26.76 (11)	C13—N5—N6—O5	171.8 (4)
O8—Pb2—O1—N2	130.8 (3)	Pb2—O5—N6—N5	−29.0 (4)
O5—Pb2—O1—N2	175.6 (3)	Pb1—O5—N6—N5	111.0 (4)
O6—Pb2—O1—N2	−145.0 (3)	Pb2—O8—N7—N8	−8.9 (6)
O7—Pb2—O1—N2	86.3 (3)	Pb2—O8—N7—C19	167.6 (3)
O8—Pb2—O1—Pb1	−75.71 (17)	O8—N7—N8—O7	0.3 (7)
O5—Pb2—O1—Pb1	−30.95 (12)	C19—N7—N8—O7	−176.1 (4)
O6—Pb2—O1—Pb1	8.49 (16)	Pb2—O7—N8—N7	8.3 (5)
O7—Pb2—O1—Pb1	−120.29 (14)	N2—N1—C1—C6	167.7 (4)
O3—Pb1—O2—N1	−81.4 (3)	O2—N1—C1—C6	−11.0 (6)
O4—Pb1—O2—N1	−145.5 (3)	N2—N1—C1—C2	−13.4 (6)
O1—Pb1—O2—N1	−5.8 (3)	O2—N1—C1—C2	168.0 (4)
O5—Pb1—O2—N1	−11.3 (3)	C6—C1—C2—C3	−1.7 (7)
O2—Pb1—O3—N4	−92.5 (3)	N1—C1—C2—C3	179.3 (4)
O4—Pb1—O3—N4	−0.7 (3)	C1—C2—C3—C4	−0.4 (7)
O1—Pb1—O3—N4	−155.7 (3)	C2—C3—C4—C5	1.6 (7)
O5—Pb1—O3—N4	141.1 (4)	C3—C4—C5—C6	−0.7 (7)
O2—Pb1—O4—N3	90.9 (3)	C2—C1—C6—C5	2.6 (7)
O3—Pb1—O4—N3	0.4 (3)	N1—C1—C6—C5	−178.5 (4)
O1—Pb1—O4—N3	35.8 (3)	C4—C5—C6—C1	−1.3 (7)
O5—Pb1—O4—N3	−44.6 (3)	N4—N3—C7—C12	160.2 (4)
O8—Pb2—O5—N6	−42.0 (3)	O4—N3—C7—C12	−21.1 (6)
O6—Pb2—O5—N6	31.3 (3)	N4—N3—C7—C8	−22.9 (6)
O7—Pb2—O5—N6	−106.2 (3)	O4—N3—C7—C8	155.8 (4)
O1—Pb2—O5—N6	171.0 (3)	C12—C7—C8—C9	0.2 (7)
O8—Pb2—O5—Pb1	174.02 (15)	N3—C7—C8—C9	−176.6 (4)
O6—Pb2—O5—Pb1	−112.72 (16)	C7—C8—C9—C10	0.8 (7)
O7—Pb2—O5—Pb1	109.80 (14)	C8—C9—C10—C11	−1.6 (8)
O1—Pb2—O5—Pb1	26.99 (11)	C9—C10—C11—C12	1.4 (8)
O2—Pb1—O5—N6	−166.4 (3)	C8—C7—C12—C11	−0.3 (7)
O3—Pb1—O5—N6	−87.0 (3)	N3—C7—C12—C11	176.5 (4)
O4—Pb1—O5—N6	−45.4 (3)	C10—C11—C12—C7	−0.5 (7)
O1—Pb1—O5—N6	−172.1 (3)	N6—N5—C13—C14	14.3 (6)
O2—Pb1—O5—Pb2	−25.19 (19)	O6—N5—C13—C14	−172.6 (4)
O3—Pb1—O5—Pb2	54.25 (14)	N6—N5—C13—C18	−162.4 (4)
O4—Pb1—O5—Pb2	95.90 (15)	O6—N5—C13—C18	10.7 (6)
O1—Pb1—O5—Pb2	−30.82 (12)	C18—C13—C14—C15	−0.3 (7)
O8—Pb2—O6—N5	59.4 (3)	N5—C13—C14—C15	−176.8 (4)
O5—Pb2—O6—N5	−28.6 (3)	C13—C14—C15—C16	0.2 (7)
O7—Pb2—O6—N5	31.2 (3)	C14—C15—C16—C17	−0.4 (8)
O1—Pb2—O6—N5	−67.2 (3)	C15—C16—C17—C18	0.6 (7)
O8—Pb2—O7—N8	−9.1 (3)	C14—C13—C18—C17	0.5 (7)
O5—Pb2—O7—N8	71.9 (3)	N5—C13—C18—C17	177.1 (4)
O6—Pb2—O7—N8	20.7 (4)	C16—C17—C18—C13	−0.7 (7)
O1—Pb2—O7—N8	134.4 (3)	N8—N7—C19—C24	146.6 (5)
O5—Pb2—O8—N7	−81.3 (3)	O8—N7—C19—C24	−30.1 (6)
O6—Pb2—O8—N7	−147.2 (3)	N8—N7—C19—C20	−33.5 (6)
O7—Pb2—O8—N7	8.6 (3)	O8—N7—C19—C20	149.8 (4)
O1—Pb2—O8—N7	−42.1 (3)	C24—C19—C20—C21	−2.3 (7)
Pb1—O2—N1—N2	6.9 (5)	N7—C19—C20—C21	177.8 (4)
Pb1—O2—N1—C1	−174.5 (3)	C19—C20—C21—C22	0.6 (8)
O2—N1—N2—O1	−1.9 (6)	C20—C21—C22—C23	1.2 (8)
C1—N1—N2—O1	179.6 (4)	C21—C22—C23—C24	−1.4 (8)
Pb1—O1—N2—N1	−4.3 (5)	C22—C23—C24—C19	−0.2 (8)
Pb2—O1—N2—N1	146.7 (3)	C20—C19—C24—C23	2.1 (7)
Pb1—O4—N3—N4	−0.2 (5)	N7—C19—C24—C23	−178.1 (4)

Experimental details

Crystal data
Chemical formula	[Pb₂(C₆H₅N₂O₂)₄]
M_r	962.86
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.6149 (5), 11.5340 (6), 13.2724 (7)
α, β, γ (°)	82.459 (1), 79.280 (1), 67.369 (1)
V (Å³)	1331.95 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	12.69
Crystal size (mm)	0.30 × 0.15 × 0.15

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.115, 0.252
No. of measured, independent and observed [I > 2σ(I)] reflections	16878, 6094, 5444
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.026, 0.071, 1.06
No. of reflections	6094
No. of parameters	379
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.74, −2.24

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

References

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