μ-Adipato-κ2O1:O4-bis­{[2,6-bis­(1H-benzimidazol-2-yl-κN3)pyridine-κN](nitrato-κO)lead(II)}

Wei, L.-Q.; Zeng, M.-H.; Ng, S.W.

doi:10.1107/S1600536809052647

metal-organic compounds

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Volume 66| Part 1| January 2010| Page m56

doi:10.1107/S1600536809052647

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μ-Adipato-κ²O¹:O⁴-bis{[2,6-bis(1H-benzimidazol-2-yl-κN³)pyridine-κN](nitrato-κO)lead(II)}

Lian-Qiang Wei,^a Ming-Hua Zeng ^a and Seik Weng Ng ^b ^*

^aSchool of Chemistry & Chemical Engineering, Guangxi Normal University, 541004 Guilin 541004, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 5 December 2009; accepted 7 December 2009; online 12 December 2009)

The dinuclear title compound, [Pb₂(C₆H₈O₄)(NO₃)₂(C₁₉H₁₃N₅)₂], lies with the mid-point of the butyl chain of the bridging adipate unit on a center of inversion. The Pb^II ion is covalently bonded to the nitrate anion and is bonded to a carboxylate group of the adipate unit by another covalent bond. The N-heterocycle functions in a chelating tridentate mode. The metal atom exists in a Ψ-octahedral coordination environment. When weaker Pb⋯O interactions are also considered, the geometry is a Ψ-tricapped trigonal prism in which the lone-pair electrons occupy one face of the trigonal prism. Adjacent molecules are linked into a layer structure by N—H⋯O hydrogen bonds.

Related literature

For the structure of a related Pb^II complex and its lone-pair sterechemistry, see: Meng et al. (2009 ).

Experimental

Crystal data

[Pb₂(C₆H₈O₄)(NO₃)₂(C₁₉H₁₃N₅)₂]
M_r = 1305.21
Triclinic, $[P \overline 1]$
a = 9.3470 (7) Å
b = 10.6433 (8) Å
c = 11.3776 (8) Å
α = 106.696 (1)°
β = 95.343 (1)°
γ = 99.117 (1)°
V = 1058.9 (1) Å³
Z = 1
Mo Kα radiation
μ = 8.02 mm⁻¹
T = 293 K
0.26 × 0.12 × 0.08 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.230, T_max = 0.566
8299 measured reflections
4561 independent reflections
3586 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.099
S = 1.02
4561 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 1.93 e Å⁻³
Δρ_min = −1.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1ⁱ	0.86	1.95	2.744 (8)	152
N5—H5⋯O3ⁱⁱ	0.86	2.10	2.891 (9)	153
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) -x+2, -y+2, -z+2.

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); 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, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809052647/bt5131sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809052647/bt5131Isup2.hkl

checkCIF report

Related literature top

For the structure of Pb₂(C₆H₈O₄)₂(C₁₉H₁₃N₅)₂ and lone-pair sterechemistry, see: Meng et al. (2009).

Experimental top

Lead nitrate (0.250 mmol), 2-(6-(1H-benzo[d]imidazol-2-yl)pyridin-2-yl)-1H-benzo[d]imidazole (0.250 mmol), adipic acid (0.125 mmol) and water (10 ml) were sealed in a 25 ml Teflon-lined, stainless-steel Parr bomb. The bomb was heated at 413 K for 4 days and cooled to room temperature. Brown block-shaped crystals were colleacted and washed in water; the yield was 25%.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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, 2009).

Figures top

	Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of Pb₂(NO₃)₂(C₆H₈O₄)(C₁₉H₁₃N₅)₂ at the 70% probability level; hydrogen atoms are drawn as sphere of arbitrary radius.
	Fig. 2. Detail of the coordination environment of the Pb^II centre.

µ-Adipato-κ²O¹:O⁴-bis{[2,6-bis(1H-benzimidazol-2- yl-κN³)pyridine-κN](nitrato-κO)lead(II)} top

Crystal data top

[Pb₂(C₆H₈O₄)(NO₃)₂(C₁₉H₁₃N₅)₂]	Z = 1
M_r = 1305.21	F(000) = 626
Triclinic, P1	D_x = 2.047 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3470 (7) Å	Cell parameters from 3150 reflections
b = 10.6433 (8) Å	θ = 2.2–24.8°
c = 11.3776 (8) Å	µ = 8.02 mm⁻¹
α = 106.696 (1)°	T = 293 K
β = 95.343 (1)°	Block, brown
γ = 99.117 (1)°	0.26 × 0.12 × 0.08 mm
V = 1058.9 (1) Å³

Data collection top

Bruker APEXII diffractometer	4561 independent reflections
Radiation source: fine-focus sealed tube	3586 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ϕ and ω scans	θ_max = 27.1°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.230, T_max = 0.566	k = −13→13
8299 measured reflections	l = −14→14

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0524P)²] where P = (F_o² + 2F_c²)/3
4561 reflections	(Δ/σ)_max = 0.001
307 parameters	Δρ_max = 1.93 e Å⁻³
0 restraints	Δρ_min = −1.17 e Å⁻³

Crystal data top

[Pb₂(C₆H₈O₄)(NO₃)₂(C₁₉H₁₃N₅)₂]	γ = 99.117 (1)°
M_r = 1305.21	V = 1058.9 (1) Å³
Triclinic, P1	Z = 1
a = 9.3470 (7) Å	Mo Kα radiation
b = 10.6433 (8) Å	µ = 8.02 mm⁻¹
c = 11.3776 (8) Å	T = 293 K
α = 106.696 (1)°	0.26 × 0.12 × 0.08 mm
β = 95.343 (1)°

Data collection top

Bruker APEXII diffractometer	4561 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3586 reflections with I > 2σ(I)
T_min = 0.230, T_max = 0.566	R_int = 0.036
8299 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.02	Δρ_max = 1.93 e Å⁻³
4561 reflections	Δρ_min = −1.17 e Å⁻³
307 parameters

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

	x	y	z	U_iso*/U_eq
Pb1	1.07669 (3)	0.71714 (3)	0.65491 (3)	0.02682 (11)
O1	0.8637 (6)	0.6980 (5)	0.5092 (5)	0.0341 (13)
O2	0.8304 (6)	0.4985 (5)	0.5330 (5)	0.0381 (13)
O3	1.2560 (7)	0.8902 (7)	0.8623 (6)	0.0579 (18)
O4	1.3952 (11)	0.7543 (10)	0.8022 (10)	0.126 (5)
O5	1.4055 (12)	0.8554 (14)	0.9916 (9)	0.141 (5)
N1	1.1854 (7)	0.8782 (6)	0.5449 (5)	0.0286 (14)
N2	1.2263 (6)	1.0797 (6)	0.5237 (5)	0.0274 (14)
H2	1.2215	1.1621	0.5343	0.033*
N3	1.0091 (7)	0.9473 (6)	0.7236 (5)	0.0251 (13)
N4	0.8962 (7)	0.7470 (6)	0.8149 (6)	0.0329 (15)
N5	0.7760 (7)	0.8747 (6)	0.9451 (6)	0.0352 (16)
H5	0.7435	0.9440	0.9839	0.042*
N6	1.3504 (9)	0.8307 (8)	0.8859 (7)	0.052 (2)
C1	1.2754 (8)	0.8763 (7)	0.4564 (7)	0.0262 (16)
C2	1.3328 (9)	0.7741 (8)	0.3826 (7)	0.0324 (18)
H2A	1.3132	0.6882	0.3893	0.039*
C3	1.4197 (9)	0.8036 (8)	0.2989 (7)	0.0349 (19)
H3	1.4600	0.7366	0.2490	0.042*
C4	1.4490 (9)	0.9331 (9)	0.2873 (7)	0.0369 (19)
H4	1.5085	0.9499	0.2303	0.044*
C5	1.3918 (8)	1.0343 (8)	0.3581 (7)	0.0350 (19)
H5A	1.4106	1.1200	0.3508	0.042*
C6	1.3046 (8)	1.0032 (7)	0.4412 (7)	0.0278 (16)
C7	1.1608 (8)	1.0009 (7)	0.5828 (6)	0.0258 (16)
C8	1.0701 (7)	1.0443 (7)	0.6764 (6)	0.0208 (14)
C9	1.0481 (8)	1.1737 (7)	0.7213 (8)	0.0344 (18)
H9	1.0887	1.2392	0.6882	0.041*
C10	0.9640 (9)	1.2052 (8)	0.8172 (7)	0.038 (2)
H10	0.9509	1.2926	0.8495	0.045*
C11	0.9004 (9)	1.1077 (8)	0.8642 (7)	0.0340 (18)
H11	0.8428	1.1276	0.9269	0.041*
C12	0.9248 (8)	0.9783 (7)	0.8148 (7)	0.0263 (16)
C13	0.8642 (8)	0.8677 (8)	0.8563 (7)	0.0299 (17)
C14	0.7477 (9)	0.7502 (8)	0.9616 (8)	0.0345 (18)
C15	0.6696 (9)	0.7026 (9)	1.0431 (8)	0.041 (2)
H15	0.6169	0.7550	1.0960	0.049*
C16	0.6744 (9)	0.5751 (10)	1.0410 (8)	0.046 (2)
H16	0.6258	0.5401	1.0958	0.056*
C17	0.7503 (11)	0.4942 (10)	0.9588 (9)	0.056 (3)
H17	0.7483	0.4066	0.9590	0.067*
C18	0.8266 (11)	0.5409 (9)	0.8793 (9)	0.050 (2)
H18	0.8782	0.4876	0.8261	0.060*
C19	0.8245 (9)	0.6720 (8)	0.8805 (7)	0.0333 (18)
C20	0.7885 (8)	0.5807 (7)	0.4878 (7)	0.0264 (16)
C21	0.6450 (8)	0.5467 (8)	0.4015 (8)	0.039 (2)
H21A	0.6606	0.4989	0.3187	0.047*
H21B	0.6159	0.6292	0.3982	0.047*
C22	0.5208 (9)	0.4628 (8)	0.4384 (7)	0.038 (2)
H22A	0.5500	0.3811	0.4443	0.045*
H22B	0.4361	0.4383	0.3746	0.045*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.02973 (17)	0.02289 (16)	0.03042 (16)	0.00981 (11)	0.00830 (11)	0.00846 (11)
O1	0.030 (3)	0.025 (3)	0.046 (3)	0.003 (2)	0.003 (3)	0.013 (2)
O2	0.041 (3)	0.027 (3)	0.051 (4)	0.009 (3)	0.010 (3)	0.016 (3)
O3	0.053 (4)	0.060 (4)	0.052 (4)	0.031 (4)	−0.009 (3)	−0.001 (3)
O4	0.127 (9)	0.126 (9)	0.097 (7)	0.085 (7)	−0.009 (6)	−0.034 (6)
O5	0.122 (9)	0.244 (14)	0.055 (6)	0.098 (9)	−0.008 (6)	0.017 (7)
N1	0.035 (4)	0.022 (3)	0.030 (3)	0.007 (3)	0.011 (3)	0.008 (3)
N2	0.030 (3)	0.022 (3)	0.031 (3)	0.006 (3)	0.007 (3)	0.008 (3)
N3	0.031 (3)	0.019 (3)	0.025 (3)	0.009 (3)	0.003 (3)	0.004 (2)
N4	0.038 (4)	0.029 (4)	0.036 (4)	0.011 (3)	0.016 (3)	0.010 (3)
N5	0.033 (4)	0.033 (4)	0.039 (4)	0.010 (3)	0.019 (3)	0.004 (3)
N6	0.057 (5)	0.062 (5)	0.037 (4)	0.029 (4)	0.006 (4)	0.005 (4)
C1	0.022 (4)	0.025 (4)	0.028 (4)	0.002 (3)	−0.002 (3)	0.007 (3)
C2	0.042 (5)	0.027 (4)	0.032 (4)	0.014 (4)	0.011 (4)	0.010 (3)
C3	0.036 (5)	0.042 (5)	0.027 (4)	0.014 (4)	0.010 (3)	0.006 (3)
C4	0.036 (5)	0.050 (5)	0.027 (4)	0.007 (4)	0.007 (4)	0.015 (4)
C5	0.033 (4)	0.033 (4)	0.040 (5)	−0.003 (4)	0.002 (4)	0.019 (4)
C6	0.022 (4)	0.030 (4)	0.028 (4)	0.004 (3)	0.000 (3)	0.005 (3)
C7	0.025 (4)	0.024 (4)	0.024 (4)	0.000 (3)	0.001 (3)	0.004 (3)
C8	0.009 (3)	0.027 (4)	0.020 (3)	0.002 (3)	−0.007 (3)	0.002 (3)
C9	0.032 (4)	0.022 (4)	0.045 (5)	0.000 (3)	−0.005 (4)	0.012 (3)
C10	0.050 (5)	0.023 (4)	0.039 (5)	0.018 (4)	0.011 (4)	−0.001 (3)
C11	0.034 (4)	0.034 (4)	0.031 (4)	0.009 (4)	0.013 (3)	0.001 (3)
C12	0.029 (4)	0.019 (4)	0.030 (4)	0.010 (3)	0.003 (3)	0.003 (3)
C13	0.028 (4)	0.029 (4)	0.029 (4)	0.005 (3)	0.002 (3)	0.005 (3)
C14	0.034 (5)	0.027 (4)	0.042 (5)	0.004 (3)	0.005 (4)	0.011 (4)
C15	0.027 (4)	0.049 (5)	0.048 (5)	0.003 (4)	0.018 (4)	0.015 (4)
C16	0.038 (5)	0.060 (6)	0.047 (5)	−0.003 (4)	0.012 (4)	0.029 (5)
C17	0.068 (7)	0.047 (6)	0.046 (6)	−0.006 (5)	0.008 (5)	0.013 (5)
C18	0.070 (7)	0.032 (5)	0.054 (6)	0.016 (5)	0.027 (5)	0.014 (4)
C19	0.033 (4)	0.032 (4)	0.035 (4)	0.009 (4)	0.012 (4)	0.007 (3)
C20	0.026 (4)	0.019 (4)	0.031 (4)	0.003 (3)	0.012 (3)	0.002 (3)
C21	0.036 (5)	0.036 (5)	0.041 (5)	−0.005 (4)	0.004 (4)	0.012 (4)
C22	0.032 (4)	0.035 (5)	0.036 (5)	0.000 (4)	0.006 (4)	−0.001 (4)

Geometric parameters (Å, º) top

Pb1—O1	2.411 (5)	C4—C5	1.364 (11)
Pb1—N1	2.541 (6)	C4—H4	0.9300
Pb1—N3	2.548 (6)	C5—C6	1.380 (11)
Pb1—N4	2.583 (6)	C5—H5A	0.9300
Pb1—O3	2.749 (6)	C7—C8	1.441 (10)
Pb1—O2	2.914 (6)	C8—C9	1.381 (10)
Pb1—O2ⁱ	2.958 (5)	C9—C10	1.397 (11)
Pb1—O4	3.185 (10)	C9—H9	0.9300
O1—C20	1.275 (9)	C10—C11	1.378 (11)
O2—C20	1.231 (9)	C10—H10	0.9300
O3—N6	1.217 (9)	C11—C12	1.393 (10)
O4—N6	1.216 (11)	C11—H11	0.9300
O5—N6	1.200 (11)	C12—C13	1.445 (11)
N1—C7	1.317 (9)	C14—C15	1.389 (11)
N1—C1	1.369 (9)	C14—C19	1.389 (11)
N2—C7	1.330 (9)	C15—C16	1.359 (12)
N2—C6	1.399 (9)	C15—H15	0.9300
N2—H2	0.8600	C16—C17	1.405 (13)
N3—C12	1.358 (9)	C16—H16	0.9300
N3—C8	1.367 (9)	C17—C18	1.356 (13)
N4—C13	1.327 (9)	C17—H17	0.9300
N4—C19	1.382 (10)	C18—C19	1.394 (12)
N5—C13	1.356 (9)	C18—H18	0.9300
N5—C14	1.379 (10)	C20—C21	1.513 (11)
N5—H5	0.8600	C21—C22	1.516 (11)
C1—C2	1.386 (10)	C21—H21A	0.9700
C1—C6	1.399 (10)	C21—H21B	0.9700
C2—C3	1.378 (11)	C22—C22ⁱⁱ	1.519 (14)
C2—H2A	0.9300	C22—H22A	0.9700
C3—C4	1.408 (11)	C22—H22B	0.9700
C3—H3	0.9300

O1—Pb1—N1	81.15 (19)	C3—C4—H4	119.3
O1—Pb1—N3	76.12 (18)	C4—C5—C6	116.6 (7)
N1—Pb1—N3	65.32 (19)	C4—C5—H5A	121.7
O1—Pb1—N4	83.9 (2)	C6—C5—H5A	121.7
N1—Pb1—N4	129.70 (19)	C5—C6—C1	123.5 (7)
N3—Pb1—N4	64.51 (19)	C5—C6—N2	131.7 (7)
O1—Pb1—O3	142.75 (18)	C1—C6—N2	104.8 (6)
N1—Pb1—O3	84.8 (2)	N1—C7—N2	112.8 (6)
N3—Pb1—O3	66.66 (19)	N1—C7—C8	123.6 (7)
N4—Pb1—O3	78.9 (2)	N2—C7—C8	123.6 (7)
O1—Pb1—O2	47.51 (16)	N3—C8—C9	120.6 (6)
N1—Pb1—O2	121.65 (18)	N3—C8—C7	114.8 (6)
N3—Pb1—O2	114.54 (17)	C9—C8—C7	124.5 (7)
N4—Pb1—O2	77.49 (18)	C8—C9—C10	119.2 (7)
O3—Pb1—O2	152.3 (2)	C8—C9—H9	120.4
O1—Pb1—O2ⁱ	89.14 (17)	C10—C9—H9	120.4
N1—Pb1—O2ⁱ	87.79 (17)	C11—C10—C9	120.6 (7)
N3—Pb1—O2ⁱ	150.76 (17)	C11—C10—H10	119.7
N4—Pb1—O2ⁱ	139.77 (18)	C9—C10—H10	119.7
O3—Pb1—O2ⁱ	124.72 (17)	C10—C11—C12	118.0 (7)
O2—Pb1—O2ⁱ	68.94 (18)	C10—C11—H11	121.0
O1—Pb1—O4	167.8 (3)	C12—C11—H11	121.0
N1—Pb1—O4	88.3 (3)	N3—C12—C11	121.9 (7)
N3—Pb1—O4	105.0 (2)	N3—C12—C13	114.9 (6)
N4—Pb1—O4	107.6 (2)	C11—C12—C13	123.2 (7)
O3—Pb1—O4	40.80 (19)	N4—C13—N5	111.9 (7)
O2—Pb1—O4	137.4 (2)	N4—C13—C12	122.8 (7)
O2ⁱ—Pb1—O4	84.36 (19)	N5—C13—C12	125.2 (7)
C20—O1—Pb1	106.6 (5)	N5—C14—C15	131.9 (8)
C20—O2—Pb1	83.5 (4)	N5—C14—C19	105.6 (7)
N6—O3—Pb1	105.7 (5)	C15—C14—C19	122.4 (8)
N6—O4—Pb1	84.3 (6)	C16—C15—C14	116.2 (8)
C7—N1—C1	106.2 (6)	C16—C15—H15	121.9
C7—N1—Pb1	116.8 (4)	C14—C15—H15	121.9
C1—N1—Pb1	136.9 (5)	C15—C16—C17	122.1 (8)
C7—N2—C6	107.1 (6)	C15—C16—H16	118.9
C7—N2—H2	126.5	C17—C16—H16	118.9
C6—N2—H2	126.5	C18—C17—C16	121.6 (9)
C12—N3—C8	119.6 (6)	C18—C17—H17	119.2
C12—N3—Pb1	120.8 (5)	C16—C17—H17	119.2
C8—N3—Pb1	119.3 (4)	C17—C18—C19	117.3 (9)
C13—N4—C19	105.6 (6)	C17—C18—H18	121.3
C13—N4—Pb1	116.7 (5)	C19—C18—H18	121.3
C19—N4—Pb1	137.6 (5)	N4—C19—C14	109.5 (7)
C13—N5—C14	107.4 (6)	N4—C19—C18	130.0 (7)
C13—N5—H5	126.3	C14—C19—C18	120.4 (8)
C14—N5—H5	126.3	O2—C20—O1	122.3 (7)
O5—N6—O4	120.5 (10)	O2—C20—C21	121.4 (7)
O5—N6—O3	119.2 (9)	O1—C20—C21	116.4 (7)
O4—N6—O3	120.1 (9)	C20—C21—C22	114.5 (7)
N1—C1—C2	131.7 (7)	C20—C21—H21A	108.6
N1—C1—C6	109.1 (6)	C22—C21—H21A	108.6
C2—C1—C6	119.2 (7)	C20—C21—H21B	108.6
C3—C2—C1	118.0 (8)	C22—C21—H21B	108.6
C3—C2—H2A	121.0	H21A—C21—H21B	107.6
C1—C2—H2A	121.0	C21—C22—C22ⁱⁱ	111.7 (8)
C2—C3—C4	121.4 (7)	C21—C22—H22A	109.3
C2—C3—H3	119.3	C22ⁱⁱ—C22—H22A	109.3
C4—C3—H3	119.3	C21—C22—H22B	109.3
C5—C4—C3	121.3 (7)	C22ⁱⁱ—C22—H22B	109.3
C5—C4—H4	119.3	H22A—C22—H22B	107.9

N1—Pb1—O1—C20	151.2 (5)	Pb1—N1—C1—C2	7.0 (13)
N3—Pb1—O1—C20	−142.2 (5)	C7—N1—C1—C6	−0.2 (8)
N4—Pb1—O1—C20	−77.0 (5)	Pb1—N1—C1—C6	−175.5 (5)
O3—Pb1—O1—C20	−139.6 (5)	N1—C1—C2—C3	178.9 (8)
O2—Pb1—O1—C20	1.6 (4)	C6—C1—C2—C3	1.6 (11)
O2ⁱ—Pb1—O1—C20	63.3 (5)	C1—C2—C3—C4	−0.5 (12)
O4—Pb1—O1—C20	120.9 (10)	C2—C3—C4—C5	−0.3 (13)
O1—Pb1—O2—C20	−1.6 (4)	C3—C4—C5—C6	0.1 (12)
N1—Pb1—O2—C20	−37.5 (5)	C4—C5—C6—C1	1.0 (12)
N3—Pb1—O2—C20	37.6 (5)	C4—C5—C6—N2	−177.8 (8)
N4—Pb1—O2—C20	91.7 (4)	N1—C1—C6—C5	−179.8 (7)
O3—Pb1—O2—C20	123.7 (5)	C2—C1—C6—C5	−1.9 (12)
O2ⁱ—Pb1—O2—C20	−110.9 (5)	N1—C1—C6—N2	−0.7 (8)
O4—Pb1—O2—C20	−165.8 (4)	C2—C1—C6—N2	177.2 (7)
O1—Pb1—O3—N6	−178.2 (5)	C7—N2—C6—C5	−179.7 (8)
N1—Pb1—O3—N6	−110.1 (6)	C7—N2—C6—C1	1.3 (8)
N3—Pb1—O3—N6	−175.4 (7)	C1—N1—C7—N2	1.1 (9)
N4—Pb1—O3—N6	117.7 (6)	Pb1—N1—C7—N2	177.5 (5)
O2—Pb1—O3—N6	85.9 (7)	C1—N1—C7—C8	179.9 (7)
O2ⁱ—Pb1—O3—N6	−26.4 (7)	Pb1—N1—C7—C8	−3.7 (9)
O4—Pb1—O3—N6	−16.7 (6)	C6—N2—C7—N1	−1.6 (9)
O1—Pb1—O4—N6	130.1 (9)	C6—N2—C7—C8	179.7 (6)
N1—Pb1—O4—N6	100.2 (8)	C12—N3—C8—C9	0.7 (10)
N3—Pb1—O4—N6	36.4 (8)	Pb1—N3—C8—C9	−173.1 (5)
N4—Pb1—O4—N6	−31.1 (8)	C12—N3—C8—C7	178.2 (6)
O3—Pb1—O4—N6	16.2 (6)	Pb1—N3—C8—C7	4.4 (8)
O2—Pb1—O4—N6	−121.7 (7)	N1—C7—C8—N3	−0.4 (10)
O2ⁱ—Pb1—O4—N6	−171.8 (8)	N2—C7—C8—N3	178.2 (6)
O1—Pb1—N1—C7	82.8 (5)	N1—C7—C8—C9	177.0 (7)
N3—Pb1—N1—C7	4.0 (5)	N2—C7—C8—C9	−4.4 (11)
N4—Pb1—N1—C7	8.3 (6)	N3—C8—C9—C10	0.8 (11)
O3—Pb1—N1—C7	−62.6 (5)	C7—C8—C9—C10	−176.4 (7)
O2—Pb1—N1—C7	108.7 (5)	C8—C9—C10—C11	−1.8 (12)
O2ⁱ—Pb1—N1—C7	172.2 (5)	C9—C10—C11—C12	1.2 (12)
O4—Pb1—N1—C7	−103.4 (5)	C8—N3—C12—C11	−1.3 (11)
O1—Pb1—N1—C1	−102.3 (7)	Pb1—N3—C12—C11	172.4 (6)
N3—Pb1—N1—C1	179.0 (8)	C8—N3—C12—C13	179.1 (6)
N4—Pb1—N1—C1	−176.8 (6)	Pb1—N3—C12—C13	−7.3 (9)
O3—Pb1—N1—C1	112.3 (7)	C10—C11—C12—N3	0.4 (12)
O2—Pb1—N1—C1	−76.3 (7)	C10—C11—C12—C13	180.0 (8)
O2ⁱ—Pb1—N1—C1	−12.8 (7)	C19—N4—C13—N5	0.0 (9)
O4—Pb1—N1—C1	71.6 (7)	Pb1—N4—C13—N5	−176.3 (5)
O1—Pb1—N3—C12	95.3 (6)	C19—N4—C13—C12	176.8 (7)
N1—Pb1—N3—C12	−178.2 (6)	Pb1—N4—C13—C12	0.5 (10)
N4—Pb1—N3—C12	5.5 (5)	C14—N5—C13—N4	−0.6 (9)
O3—Pb1—N3—C12	−83.0 (6)	C14—N5—C13—C12	−177.2 (7)
O2—Pb1—N3—C12	66.7 (6)	N3—C12—C13—N4	4.4 (11)
O2ⁱ—Pb1—N3—C12	157.1 (5)	C11—C12—C13—N4	−175.2 (8)
O4—Pb1—N3—C12	−97.2 (6)	N3—C12—C13—N5	−179.3 (7)
O1—Pb1—N3—C8	−91.0 (5)	C11—C12—C13—N5	1.1 (12)
N1—Pb1—N3—C8	−4.5 (5)	C13—N5—C14—C15	177.1 (9)
N4—Pb1—N3—C8	179.2 (5)	C13—N5—C14—C19	0.8 (9)
O3—Pb1—N3—C8	90.7 (5)	N5—C14—C15—C16	−174.5 (9)
O2—Pb1—N3—C8	−119.6 (5)	C19—C14—C15—C16	1.2 (13)
O2ⁱ—Pb1—N3—C8	−29.2 (7)	C14—C15—C16—C17	−1.8 (14)
O4—Pb1—N3—C8	76.5 (5)	C15—C16—C17—C18	1.9 (16)
O1—Pb1—N4—C13	−80.3 (6)	C16—C17—C18—C19	−1.2 (16)
N1—Pb1—N4—C13	−7.2 (7)	C13—N4—C19—C14	0.5 (9)
N3—Pb1—N4—C13	−2.9 (5)	Pb1—N4—C19—C14	175.6 (6)
O3—Pb1—N4—C13	66.4 (6)	C13—N4—C19—C18	−176.0 (9)
O2—Pb1—N4—C13	−128.1 (6)	Pb1—N4—C19—C18	−0.9 (15)
O2ⁱ—Pb1—N4—C13	−161.8 (5)	N5—C14—C19—N4	−0.8 (9)
O4—Pb1—N4—C13	95.7 (6)	C15—C14—C19—N4	−177.5 (8)
O1—Pb1—N4—C19	104.9 (8)	N5—C14—C19—C18	176.1 (8)
N1—Pb1—N4—C19	178.1 (7)	C15—C14—C19—C18	−0.6 (13)
N3—Pb1—N4—C19	−177.6 (9)	C17—C18—C19—N4	176.8 (9)
O3—Pb1—N4—C19	−108.3 (8)	C17—C18—C19—C14	0.6 (14)
O2—Pb1—N4—C19	57.2 (8)	Pb1—O2—C20—O1	2.6 (7)
O2ⁱ—Pb1—N4—C19	23.5 (9)	Pb1—O2—C20—C21	−178.5 (7)
O4—Pb1—N4—C19	−79.0 (8)	Pb1—O1—C20—O2	−3.2 (8)
Pb1—O4—N6—O5	156.9 (12)	Pb1—O1—C20—C21	177.8 (5)
Pb1—O4—N6—O3	−28.4 (10)	O2—C20—C21—C22	39.6 (10)
Pb1—O3—N6—O5	−150.5 (10)	O1—C20—C21—C22	−141.5 (7)
Pb1—O3—N6—O4	34.7 (12)	C20—C21—C22—C22ⁱⁱ	64.3 (12)
C7—N1—C1—C2	−177.7 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱⁱⁱ	0.86	1.95	2.744 (8)	152
N5—H5···O3^iv	0.86	2.10	2.891 (9)	153

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

Experimental details

Crystal data
Chemical formula	[Pb₂(C₆H₈O₄)(NO₃)₂(C₁₉H₁₃N₅)₂]
M_r	1305.21
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.3470 (7), 10.6433 (8), 11.3776 (8)
α, β, γ (°)	106.696 (1), 95.343 (1), 99.117 (1)
V (Å³)	1058.9 (1)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	8.02
Crystal size (mm)	0.26 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.230, 0.566
No. of measured, independent and observed [I > 2σ(I)] reflections	8299, 4561, 3586
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.641

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.099, 1.02
No. of reflections	4561
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.93, −1.17

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1ⁱ	0.86	1.95	2.744 (8)	152
N5—H5···O3ⁱⁱ	0.86	2.10	2.891 (9)	153

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

Acknowledgements

This work was supported by the Guangxi Graduate Education Innovation Program (2009106020703M44) and the University of Malaya.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Meng, F.-Y., Zhou, Y.-L., Zou, H.-H., Zeng, M.-H. & Liang, H. (2009). J. Mol. Struct. 920, 238–241. Web of Science CSD CrossRef CAS 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. (2009). publCIF. In preparation. Google Scholar

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