Bis(N-nitroso-N-phenyl­hydroxy­laminato-κ2O,O′)(1,10-phenanthroline-κ2N,N′)lead(II)

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

doi:10.1107/S1600536811006787

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page m378

doi:10.1107/S1600536811006787

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Bis(N-nitroso-N-phenylhydroxylaminato-κ²O,O′)(1,10-phenanthroline-κ²N,N′)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 two cupferronate ions and the N-heterocycle in the mononuclear title compound, [Pb(C₆H₅N₂O₂)₂(C₁₂H₈N₂)], O,O′- and N,N′-chelate to the Pb^II atom, the geometry of which is a distorted Ψ-pentagonal bipyramid.

Related literature

For the structure of dinuclear [Pb(C₆H₅N₂O₂)₂]₂, see: Najafi et al. (2011 ).

Experimental

Crystal data

[Pb(C₆H₅N₂O₂)₂(C₁₂H₈N₂)]
M_r = 661.63
Monoclinic, P 2₁ /c
a = 7.7033 (4) Å
b = 15.9948 (8) Å
c = 18.8929 (10) Å
β = 100.919 (1)°
V = 2285.7 (2) Å³
Z = 4
Mo Kα radiation
μ = 7.43 mm⁻¹
T = 100 K
0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.318, T_max = 0.524
21418 measured reflections
5233 independent reflections
4676 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.018
wR(F²) = 0.047
S = 0.91
5233 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.53 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/S1600536811006787/bt5481sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811006787/bt5481Isup2.hkl

checkCIF report

Comment top

The cupferronate ion is a common ion used for the complexation of metals; the lead(II) derivative exists as a dinuclear compound, the four cupferronate ions in dinuclear [Pb(C₆H₅N₂O₂)₂]₂ O,O'-chelate to the lead(II) atom, and two of the four nitroso O atoms are also involved in bridging. 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 (Najafi et al., 2011). The 1,10-phenanthroline adduct is monomeric (Scheme I, Fig. 1). The two cupferronate ions and the N-heterocycle in mononuclear Pb(C₁₂H₈N₂)(C₆H₅N₂O₂)₂ chelate to the lead(II) atom; the geometry of the lead atom is a Ψ-pentagonal bipyramid.

Related literature top

For the structure of dinuclear [Pb(C₆H₅N₂O₂)₂]₂, see: Najafi et al. (2011).

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) and 1,10-phenanthroline hydrate (0.40, 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 Pb(C₁₂H₈N₂)(C₆H₅N₂O₂)₂ at the 70% probability level. Hydrogen atoms are drawn as spheres of arbitrary radius.

Bis(N-nitroso-N-phenylhydroxylaminato- κ²O,O')(1,10-phenanthroline-κ²N,N')lead(II) top

Crystal data top

[Pb(C₆H₅N₂O₂)₂(C₁₂H₈N₂)]	F(000) = 1272
M_r = 661.63	D_x = 1.923 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9896 reflections
a = 7.7033 (4) Å	θ = 2.2–28.3°
b = 15.9948 (8) Å	µ = 7.43 mm⁻¹
c = 18.8929 (10) Å	T = 100 K
β = 100.919 (1)°	Prism, brown
V = 2285.7 (2) Å³	0.20 × 0.10 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX diffractometer	5233 independent reflections
Radiation source: fine-focus sealed tube	4676 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→10
T_min = 0.318, T_max = 0.524	k = −20→18
21418 measured reflections	l = −24→24

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)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.047	H-atom parameters constrained
S = 0.91	w = 1/[σ²(F_o²) + (0.0315P)² + 1.0382P] where P = (F_o² + 2F_c²)/3
5233 reflections	(Δ/σ)_max = 0.001
316 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.53 e Å⁻³

Crystal data top

[Pb(C₆H₅N₂O₂)₂(C₁₂H₈N₂)]	V = 2285.7 (2) Å³
M_r = 661.63	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 7.7033 (4) Å	µ = 7.43 mm⁻¹
b = 15.9948 (8) Å	T = 100 K
c = 18.8929 (10) Å	0.20 × 0.10 × 0.10 mm
β = 100.919 (1)°

Data collection top

Bruker SMART APEX diffractometer	5233 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4676 reflections with I > 2σ(I)
T_min = 0.318, T_max = 0.524	R_int = 0.028
21418 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.018	0 restraints
wR(F²) = 0.047	H-atom parameters constrained
S = 0.91	Δρ_max = 0.74 e Å⁻³
5233 reflections	Δρ_min = −0.53 e Å⁻³
316 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	0.545412 (12)	0.564925 (6)	0.707994 (5)	0.01407 (4)
O1	0.6518 (3)	0.57008 (11)	0.83910 (10)	0.0215 (4)
O2	0.6004 (3)	0.43217 (11)	0.77043 (10)	0.0221 (4)
O3	0.3666 (2)	0.67625 (11)	0.74664 (10)	0.0171 (4)
O4	0.2682 (2)	0.52341 (11)	0.72411 (10)	0.0168 (4)
N1	0.6651 (3)	0.49786 (14)	0.87218 (11)	0.0167 (4)
N2	0.6420 (3)	0.42654 (14)	0.84043 (12)	0.0207 (5)
N3	0.2048 (3)	0.65180 (13)	0.74731 (10)	0.0123 (4)
N4	0.1479 (3)	0.57674 (12)	0.73517 (11)	0.0139 (4)
N5	0.4379 (3)	0.44824 (13)	0.60458 (12)	0.0156 (4)
N6	0.3223 (3)	0.61102 (14)	0.58176 (11)	0.0160 (4)
C1	0.7119 (4)	0.49851 (17)	0.94969 (14)	0.0189 (5)
C2	0.6692 (4)	0.43069 (17)	0.98924 (15)	0.0228 (6)
H2	0.6111	0.3831	0.9657	0.027*
C3	0.7135 (5)	0.43430 (18)	1.06373 (16)	0.0298 (7)
H3	0.6877	0.3882	1.0917	0.036*
C4	0.7955 (5)	0.5050 (2)	1.09786 (15)	0.0355 (8)
H4	0.8229	0.5075	1.1490	0.043*
C5	0.8371 (5)	0.57181 (19)	1.05735 (16)	0.0345 (8)
H5	0.8947	0.6196	1.0808	0.041*
C6	0.7950 (4)	0.56902 (18)	0.98277 (15)	0.0254 (6)
H6	0.8225	0.6147	0.9548	0.031*
C7	0.0758 (3)	0.71352 (15)	0.75744 (13)	0.0132 (5)
C8	−0.0737 (3)	0.68857 (16)	0.78329 (13)	0.0159 (5)
H8	−0.0865	0.6325	0.7980	0.019*
C9	−0.2042 (4)	0.74779 (17)	0.78711 (14)	0.0193 (5)
H9	−0.3089	0.7319	0.8034	0.023*
C10	−0.1817 (4)	0.83009 (17)	0.76720 (14)	0.0211 (6)
H10	−0.2722	0.8701	0.7686	0.025*
C11	−0.0270 (4)	0.85391 (16)	0.74523 (14)	0.0187 (5)
H11	−0.0099	0.9108	0.7338	0.022*
C12	0.1030 (3)	0.79543 (15)	0.73976 (13)	0.0156 (5)
H12	0.2084	0.8115	0.7242	0.019*
C13	0.4890 (4)	0.36929 (17)	0.61474 (14)	0.0195 (6)
H13	0.5640	0.3550	0.6590	0.023*
C14	0.4390 (4)	0.30593 (17)	0.56419 (14)	0.0213 (6)
H14	0.4786	0.2502	0.5743	0.026*
C15	0.3320 (4)	0.32538 (17)	0.49995 (14)	0.0202 (6)
H15	0.2974	0.2832	0.4647	0.024*
C16	0.2737 (3)	0.40803 (17)	0.48634 (14)	0.0174 (5)
C17	0.3300 (3)	0.46863 (17)	0.54094 (13)	0.0153 (5)
C18	0.1582 (4)	0.43202 (17)	0.42116 (14)	0.0204 (6)
H18	0.1205	0.3912	0.3850	0.024*
C19	0.1015 (4)	0.51195 (18)	0.41007 (14)	0.0198 (6)
H19	0.0243	0.5263	0.3664	0.024*
C20	0.1563 (4)	0.57524 (16)	0.46329 (14)	0.0177 (5)
C21	0.2698 (3)	0.55380 (16)	0.52921 (13)	0.0156 (5)
C22	0.0991 (4)	0.65833 (18)	0.45407 (14)	0.0210 (6)
H22	0.0237	0.6750	0.4106	0.025*
C23	0.1520 (4)	0.71536 (18)	0.50770 (14)	0.0217 (6)
H23	0.1136	0.7718	0.5021	0.026*
C24	0.2643 (3)	0.68889 (17)	0.57130 (14)	0.0194 (5)
H24	0.3002	0.7287	0.6085	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.01178 (6)	0.01599 (6)	0.01461 (5)	−0.00027 (4)	0.00298 (4)	−0.00125 (3)
O1	0.0316 (12)	0.0155 (10)	0.0164 (9)	−0.0056 (8)	0.0021 (8)	0.0018 (7)
O2	0.0287 (12)	0.0188 (10)	0.0172 (9)	0.0091 (8)	0.0003 (8)	−0.0034 (7)
O3	0.0097 (8)	0.0152 (9)	0.0267 (9)	−0.0040 (7)	0.0043 (7)	−0.0032 (7)
O4	0.0155 (9)	0.0112 (9)	0.0250 (9)	0.0015 (7)	0.0073 (7)	−0.0010 (7)
N1	0.0163 (11)	0.0166 (11)	0.0173 (10)	0.0003 (9)	0.0031 (8)	0.0008 (9)
N2	0.0243 (13)	0.0184 (12)	0.0181 (11)	0.0058 (9)	0.0008 (9)	−0.0022 (9)
N3	0.0109 (10)	0.0117 (10)	0.0137 (9)	0.0006 (8)	0.0006 (8)	0.0003 (8)
N4	0.0140 (11)	0.0102 (10)	0.0175 (10)	−0.0011 (8)	0.0033 (8)	0.0001 (8)
N5	0.0143 (11)	0.0172 (11)	0.0162 (10)	0.0009 (9)	0.0049 (9)	0.0002 (8)
N6	0.0139 (11)	0.0187 (11)	0.0160 (10)	0.0012 (9)	0.0047 (8)	0.0001 (9)
C1	0.0192 (14)	0.0211 (14)	0.0157 (12)	0.0002 (11)	0.0015 (10)	0.0006 (10)
C2	0.0258 (16)	0.0186 (14)	0.0225 (14)	−0.0020 (11)	0.0004 (11)	0.0013 (11)
C3	0.043 (2)	0.0256 (16)	0.0197 (14)	−0.0043 (14)	0.0019 (13)	0.0061 (11)
C4	0.058 (2)	0.0329 (18)	0.0131 (13)	−0.0125 (16)	−0.0011 (13)	0.0020 (12)
C5	0.053 (2)	0.0283 (17)	0.0179 (14)	−0.0126 (15)	−0.0028 (14)	−0.0020 (12)
C6	0.0319 (17)	0.0239 (16)	0.0197 (13)	−0.0081 (12)	0.0031 (12)	0.0041 (11)
C7	0.0126 (12)	0.0131 (12)	0.0128 (11)	0.0004 (9)	−0.0002 (9)	−0.0021 (9)
C8	0.0152 (13)	0.0117 (12)	0.0204 (12)	−0.0026 (10)	0.0025 (10)	−0.0019 (10)
C9	0.0158 (13)	0.0186 (14)	0.0237 (13)	−0.0008 (11)	0.0041 (11)	−0.0066 (10)
C10	0.0202 (14)	0.0175 (13)	0.0249 (13)	0.0068 (11)	0.0023 (11)	−0.0047 (11)
C11	0.0245 (15)	0.0108 (12)	0.0193 (12)	0.0002 (11)	0.0007 (11)	−0.0009 (10)
C12	0.0167 (13)	0.0130 (12)	0.0163 (11)	−0.0010 (10)	0.0010 (10)	−0.0005 (10)
C13	0.0178 (14)	0.0215 (14)	0.0202 (13)	0.0035 (11)	0.0059 (11)	−0.0002 (11)
C14	0.0225 (14)	0.0148 (13)	0.0288 (14)	0.0008 (11)	0.0100 (11)	−0.0006 (11)
C15	0.0197 (14)	0.0196 (14)	0.0230 (13)	−0.0040 (11)	0.0082 (11)	−0.0043 (11)
C16	0.0140 (13)	0.0218 (13)	0.0186 (12)	−0.0045 (11)	0.0085 (10)	−0.0022 (10)
C17	0.0101 (12)	0.0196 (13)	0.0175 (12)	−0.0046 (10)	0.0059 (10)	−0.0019 (10)
C18	0.0192 (14)	0.0249 (15)	0.0180 (12)	−0.0082 (11)	0.0060 (11)	−0.0036 (11)
C19	0.0163 (13)	0.0294 (15)	0.0135 (12)	−0.0051 (11)	0.0020 (10)	0.0003 (10)
C20	0.0145 (13)	0.0254 (15)	0.0146 (12)	−0.0024 (11)	0.0062 (10)	0.0024 (10)
C21	0.0127 (13)	0.0206 (14)	0.0152 (12)	−0.0025 (10)	0.0068 (10)	−0.0008 (10)
C22	0.0143 (13)	0.0293 (15)	0.0188 (12)	0.0008 (11)	0.0018 (10)	0.0078 (11)
C23	0.0207 (14)	0.0219 (15)	0.0238 (13)	0.0004 (11)	0.0073 (11)	0.0044 (11)
C24	0.0198 (13)	0.0187 (13)	0.0212 (12)	0.0003 (11)	0.0080 (10)	−0.0002 (10)

Geometric parameters (Å, º) top

Pb1—O4	2.3106 (18)	C7—C8	1.392 (3)
Pb1—O2	2.4270 (18)	C8—C9	1.393 (4)
Pb1—O3	2.4457 (17)	C8—H8	0.9500
Pb1—O1	2.4586 (19)	C9—C10	1.389 (4)
Pb1—N5	2.715 (2)	C9—H9	0.9500
Pb1—N6	2.763 (2)	C10—C11	1.387 (4)
O1—N1	1.308 (3)	C10—H10	0.9500
O2—N2	1.304 (3)	C11—C12	1.389 (4)
O3—N3	1.309 (3)	C11—H11	0.9500
O4—N4	1.305 (3)	C12—H12	0.9500
N1—N2	1.285 (3)	C13—C14	1.396 (4)
N1—C1	1.440 (3)	C13—H13	0.9500
N3—N4	1.284 (3)	C14—C15	1.367 (4)
N3—C7	1.439 (3)	C14—H14	0.9500
N5—C13	1.326 (3)	C15—C16	1.404 (4)
N5—C17	1.365 (3)	C15—H15	0.9500
N6—C24	1.325 (3)	C16—C17	1.422 (4)
N6—C21	1.354 (3)	C16—C18	1.428 (4)
C1—C6	1.386 (4)	C17—C21	1.443 (4)
C1—C2	1.392 (4)	C18—C19	1.354 (4)
C2—C3	1.385 (4)	C18—H18	0.9500
C2—H2	0.9500	C19—C20	1.433 (4)
C3—C4	1.392 (4)	C19—H19	0.9500
C3—H3	0.9500	C20—C22	1.401 (4)
C4—C5	1.387 (4)	C20—C21	1.421 (4)
C4—H4	0.9500	C22—C23	1.367 (4)
C5—C6	1.385 (4)	C22—H22	0.9500
C5—H5	0.9500	C23—C24	1.406 (4)
C6—H6	0.9500	C23—H23	0.9500
C7—C12	1.378 (3)	C24—H24	0.9500

O4—Pb1—O2	76.42 (7)	C8—C7—N3	119.2 (2)
O4—Pb1—O3	65.37 (6)	C7—C8—C9	118.5 (2)
O2—Pb1—O3	123.25 (6)	C7—C8—H8	120.8
O4—Pb1—O1	90.97 (7)	C9—C8—H8	120.8
O2—Pb1—O1	62.97 (6)	C10—C9—C8	120.1 (2)
O3—Pb1—O1	76.93 (6)	C10—C9—H9	119.9
O4—Pb1—N5	74.56 (6)	C8—C9—H9	119.9
O2—Pb1—N5	75.51 (6)	C11—C10—C9	120.0 (2)
O3—Pb1—N5	127.08 (6)	C11—C10—H10	120.0
O1—Pb1—N5	138.25 (6)	C9—C10—H10	120.0
O4—Pb1—N6	75.59 (6)	C10—C11—C12	120.7 (2)
O2—Pb1—N6	132.52 (7)	C10—C11—H11	119.7
O3—Pb1—N6	76.70 (6)	C12—C11—H11	119.7
O1—Pb1—N6	153.50 (7)	C7—C12—C11	118.5 (2)
N5—Pb1—N6	60.47 (6)	C7—C12—H12	120.8
N1—O1—Pb1	115.64 (14)	C11—C12—H12	120.8
N2—O2—Pb1	122.70 (14)	N5—C13—C14	123.8 (3)
N3—O3—Pb1	112.12 (13)	N5—C13—H13	118.1
N4—O4—Pb1	122.37 (14)	C14—C13—H13	118.1
N2—N1—O1	124.7 (2)	C15—C14—C13	118.9 (3)
N2—N1—C1	117.8 (2)	C15—C14—H14	120.5
O1—N1—C1	117.5 (2)	C13—C14—H14	120.5
N1—N2—O2	113.4 (2)	C14—C15—C16	119.7 (2)
N4—N3—O3	124.9 (2)	C14—C15—H15	120.2
N4—N3—C7	116.4 (2)	C16—C15—H15	120.2
O3—N3—C7	118.64 (19)	C15—C16—C17	117.8 (2)
N3—N4—O4	114.2 (2)	C15—C16—C18	122.4 (2)
C13—N5—C17	118.0 (2)	C17—C16—C18	119.8 (3)
C13—N5—Pb1	120.57 (17)	N5—C17—C16	121.8 (2)
C17—N5—Pb1	121.42 (16)	N5—C17—C21	119.0 (2)
C24—N6—C21	118.7 (2)	C16—C17—C21	119.2 (2)
C24—N6—Pb1	121.10 (17)	C19—C18—C16	121.1 (2)
C21—N6—Pb1	120.19 (16)	C19—C18—H18	119.4
C6—C1—C2	121.9 (2)	C16—C18—H18	119.4
C6—C1—N1	118.0 (2)	C18—C19—C20	121.0 (2)
C2—C1—N1	120.1 (2)	C18—C19—H19	119.5
C3—C2—C1	118.4 (3)	C20—C19—H19	119.5
C3—C2—H2	120.8	C22—C20—C21	117.7 (2)
C1—C2—H2	120.8	C22—C20—C19	122.6 (2)
C2—C3—C4	120.5 (3)	C21—C20—C19	119.7 (2)
C2—C3—H3	119.8	N6—C21—C20	121.9 (2)
C4—C3—H3	119.8	N6—C21—C17	118.9 (2)
C5—C4—C3	120.2 (3)	C20—C21—C17	119.3 (2)
C5—C4—H4	119.9	C23—C22—C20	119.9 (3)
C3—C4—H4	119.9	C23—C22—H22	120.0
C6—C5—C4	120.1 (3)	C20—C22—H22	120.0
C6—C5—H5	119.9	C22—C23—C24	118.8 (3)
C4—C5—H5	119.9	C22—C23—H23	120.6
C1—C6—C5	119.0 (3)	C24—C23—H23	120.6
C1—C6—H6	120.5	N6—C24—C23	123.1 (3)
C5—C6—H6	120.5	N6—C24—H24	118.5
C12—C7—C8	122.1 (2)	C23—C24—H24	118.5
C12—C7—N3	118.6 (2)

O4—Pb1—O1—N1	68.29 (18)	C1—C2—C3—C4	1.3 (5)
O2—Pb1—O1—N1	−5.91 (16)	C2—C3—C4—C5	−1.4 (6)
O3—Pb1—O1—N1	132.71 (18)	C3—C4—C5—C6	1.0 (6)
N5—Pb1—O1—N1	0.7 (2)	C2—C1—C6—C5	0.3 (5)
N6—Pb1—O1—N1	126.70 (18)	N1—C1—C6—C5	178.4 (3)
O4—Pb1—O2—N2	−92.0 (2)	C4—C5—C6—C1	−0.4 (5)
O3—Pb1—O2—N2	−44.2 (2)	N4—N3—C7—C12	−152.2 (2)
O1—Pb1—O2—N2	6.17 (19)	O3—N3—C7—C12	23.7 (3)
N5—Pb1—O2—N2	−169.3 (2)	N4—N3—C7—C8	26.5 (3)
N6—Pb1—O2—N2	−147.37 (18)	O3—N3—C7—C8	−157.6 (2)
O4—Pb1—O3—N3	−7.02 (13)	C12—C7—C8—C9	3.9 (4)
O2—Pb1—O3—N3	−59.47 (16)	N3—C7—C8—C9	−174.7 (2)
O1—Pb1—O3—N3	−104.23 (15)	C7—C8—C9—C10	−1.7 (4)
N5—Pb1—O3—N3	37.44 (17)	C8—C9—C10—C11	−1.7 (4)
N6—Pb1—O3—N3	73.02 (14)	C9—C10—C11—C12	2.9 (4)
O2—Pb1—O4—N4	146.36 (18)	C8—C7—C12—C11	−2.7 (4)
O3—Pb1—O4—N4	9.37 (16)	N3—C7—C12—C11	176.0 (2)
O1—Pb1—O4—N4	84.50 (17)	C10—C11—C12—C7	−0.8 (4)
N5—Pb1—O4—N4	−135.20 (18)	C17—N5—C13—C14	0.0 (4)
N6—Pb1—O4—N4	−72.39 (17)	Pb1—N5—C13—C14	179.90 (19)
Pb1—O1—N1—N2	6.5 (3)	N5—C13—C14—C15	0.5 (4)
Pb1—O1—N1—C1	−174.66 (17)	C13—C14—C15—C16	−0.5 (4)
O1—N1—N2—O2	−1.0 (4)	C14—C15—C16—C17	0.2 (4)
C1—N1—N2—O2	−179.9 (2)	C14—C15—C16—C18	−178.3 (2)
Pb1—O2—N2—N1	−5.4 (3)	C13—N5—C17—C16	−0.4 (4)
Pb1—O3—N3—N4	5.5 (3)	Pb1—N5—C17—C16	179.72 (17)
Pb1—O3—N3—C7	−170.04 (15)	C13—N5—C17—C21	178.8 (2)
O3—N3—N4—O4	2.4 (3)	Pb1—N5—C17—C21	−1.1 (3)
C7—N3—N4—O4	177.98 (19)	C15—C16—C17—N5	0.3 (4)
Pb1—O4—N4—N3	−10.2 (3)	C18—C16—C17—N5	178.9 (2)
O4—Pb1—N5—C13	−96.9 (2)	C15—C16—C17—C21	−178.9 (2)
O2—Pb1—N5—C13	−17.25 (19)	C18—C16—C17—C21	−0.3 (4)
O3—Pb1—N5—C13	−138.21 (18)	C15—C16—C18—C19	178.8 (3)
O1—Pb1—N5—C13	−23.3 (2)	C17—C16—C18—C19	0.3 (4)
N6—Pb1—N5—C13	−178.8 (2)	C16—C18—C19—C20	0.3 (4)
O4—Pb1—N5—C17	83.03 (18)	C18—C19—C20—C22	−179.3 (3)
O2—Pb1—N5—C17	162.6 (2)	C18—C19—C20—C21	−0.9 (4)
O3—Pb1—N5—C17	41.7 (2)	C24—N6—C21—C20	0.6 (4)
O1—Pb1—N5—C17	156.59 (17)	Pb1—N6—C21—C20	−179.48 (18)
N6—Pb1—N5—C17	1.10 (17)	C24—N6—C21—C17	−178.8 (2)
O4—Pb1—N6—C24	98.62 (19)	Pb1—N6—C21—C17	1.0 (3)
O2—Pb1—N6—C24	154.25 (17)	C22—C20—C21—N6	−0.1 (4)
O3—Pb1—N6—C24	31.04 (18)	C19—C20—C21—N6	−178.6 (2)
O1—Pb1—N6—C24	37.1 (3)	C22—C20—C21—C17	179.4 (2)
N5—Pb1—N6—C24	178.8 (2)	C19—C20—C21—C17	0.9 (4)
O4—Pb1—N6—C21	−81.27 (18)	N5—C17—C21—N6	0.0 (3)
O2—Pb1—N6—C21	−25.6 (2)	C16—C17—C21—N6	179.2 (2)
O3—Pb1—N6—C21	−148.84 (19)	N5—C17—C21—C20	−179.5 (2)
O1—Pb1—N6—C21	−142.83 (17)	C16—C17—C21—C20	−0.3 (4)
N5—Pb1—N6—C21	−1.08 (17)	C21—C20—C22—C23	−0.4 (4)
N2—N1—C1—C6	158.2 (3)	C19—C20—C22—C23	178.1 (2)
O1—N1—C1—C6	−20.8 (4)	C20—C22—C23—C24	0.3 (4)
N2—N1—C1—C2	−23.7 (4)	C21—N6—C24—C23	−0.7 (4)
O1—N1—C1—C2	157.4 (3)	Pb1—N6—C24—C23	179.37 (18)
C6—C1—C2—C3	−0.7 (5)	C22—C23—C24—N6	0.3 (4)
N1—C1—C2—C3	−178.8 (3)

Experimental details

Crystal data
Chemical formula	[Pb(C₆H₅N₂O₂)₂(C₁₂H₈N₂)]
M_r	661.63
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.7033 (4), 15.9948 (8), 18.8929 (10)
β (°)	100.919 (1)
V (Å³)	2285.7 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	7.43
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.318, 0.524
No. of measured, independent and observed [I > 2σ(I)] reflections	21418, 5233, 4676
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.018, 0.047, 0.91
No. of reflections	5233
No. of parameters	316
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.74, −0.53

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

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Najafi, E., Amini, M. M. & Ng, S. W. (2011). Acta Cryst. E67, m377. CSD CrossRef IUCr Journals 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

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