catena-Poly[lead(II)-bis­(μ2-pyridazine-3-carboxyl­ato-κ3N2,O:O)]

Starosta, W.; Leciejewicz, J.

doi:10.1107/S1600536810002199

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m192

https://doi.org/10.1107/S1600536810002199

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catena-Poly[lead(II)-bis(μ₂-pyridazine-3-carboxylato-κ³N²,O:O)]

Wojciech Starosta ^a and Janusz Leciejewicz ^a ^*

^aInstitute of Nuclear Chemistry and Technology, ul.Dorodna 16, 03-195 Warszawa, Poland
^*Correspondence e-mail: j.leciejewicz@ichtj.waw.pl

(Received 14 January 2010; accepted 18 January 2010; online 23 January 2010)

In the title structure, [Pb(C₅H₃N₂O₂)₂]_n, the Pb^II ion is six-coordinated by two pyridazine-3-carboxylate ligands via N and O atoms, with the carboxylato O atoms acting as bidentate and bridging adjacent Pb^II ions, giving rise to catenated molecular ribbons propagating along the a-axis direction. The ribbons are connected by C—H⋯O hydrogen bonds and van der Waals interactions.

Related literature

For the structures of 3d-metal and Mg(II) complexes with pyridazine-3-carboxylate and water ligands containing monomeric molecules with an octahedral enviroment for the metal ion, see: Ardiwinata et al. (1989 ), Gryz et al. (2003 , 2004 , 2006 ). Centrosymmetric dimeric molecules, each with a different bridging mode, have been reported in the structure of a calcium(II) complex (Starosta & Leciejewicz, 2007 ), a uranyl complex (Leciejewicz & Starosta, 2009 ) as well as in the structure of a lead(II) complex with pyridazine-4-carboxylate ligands (Starosta & Leciejewicz, 2009 ). For the structure of pyridazine-3-carboxylic acid hydrochloride, see: Gryz et al. (2003).

Experimental

Crystal data

[Pb(C₅H₃N₂O₂)₂]
M_r = 453.38
Monoclinic, P 2₁ /n
a = 8.0336 (16) Å
b = 10.386 (2) Å
c = 13.766 (3) Å
β = 93.72 (3)°
V = 1146.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 14.74 mm⁻¹
T = 293 K
0.33 × 0.09 × 0.08 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.284, T_max = 0.379
3587 measured reflections
3365 independent reflections
2119 reflections with I > 2σ(I)
R_int = 0.040
3 standard reflections every 200 reflections intensity decay: 1.3%

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.137
S = 1.05
3365 reflections
172 parameters
H-atom parameters constrained
Δρ_max = 6.57 e Å⁻³
Δρ_min = −4.30 e Å⁻³

Table 1
Selected bond lengths (Å)

Pb1—O21	2.492 (7)
Pb1—O11	2.569 (6)
Pb1—N12	2.645 (7)
Pb1—O21ⁱ	2.662 (7)
Pb1—O11ⁱⁱ	2.669 (6)
Pb1—N22	2.672 (6)
Symmetry codes: (i) -x+1, -y+2, -z+2; (ii) -x, -y+2, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16⋯O12ⁱⁱⁱ	0.93	2.35	3.182 (12)	149
C14—H14⋯O21^iv	0.93	2.76	3.489 (10)	136
C26—H26⋯O22^v	0.93	2.42	3.201 (12)	142
C15—H15⋯O11^vi	0.93	2.40	3.266 (10)	155
C25—H25⋯O12^vii	0.93	2.42	3.328 (12)	165
Symmetry codes: (iii) x+1, y, z; (iv) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) x-1, y, z; (vi) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vii) -x, -y+1, -z+2.

Data collection: KM-4 Software (Kuma, 1996 $[Kuma (1996). KM-4 Software. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); cell refinement: KM-4 Software; data reduction: DATAPROC (Kuma, 2001 $[Kuma (2001). DATAPROC. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810002199/kp2247sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002199/kp2247Isup2.hkl

checkCIF report

Comment top

In the structure of the title compound (I) each Pb^II ion is coordinated by two symmetry independent ligand molecules via N,O atoms; their O atoms act as bidentate and bridging to adjacent metal ions (Fig. 1) to form molecular ribbons extending in the a direction (Fig.2). The second O atom of each carboxylato group does not participate in coordination. The coordination environment of a Pb^II ion involving O11,N12, O21, N22 and two bridging carboxylate O11^(I) and O21^(II) atoms (Table 1) is highly distorted. Both pyridazine rings are planar with r.m.s. of 0.0037 (2)Å and 0.0120((2)Å. The dihedral angle between the rings is 45.2 (1)°. Carboxylato planes make dihedral angles with the respective rings of 9.7 (1)° (C13/O11/O12) and of 8.8 (2)° (C23/O21/22). Bond distances and bond angles within both ligand molecules are in fair agreement with those reported for pyridazine-3-carboxylic acid chloride and other metal complexes with this ligand. The ribbons are held together by weak interactions between ring carbon atoms and carboxylato O atoms belonging to adjacent ribbons (Table 2).

Related literature top

For the structures of 3d-metal and Mg(II) complexes with pyridazine-3-carboxylate and water ligands containing monomeric molecules with an octahedral enviroment for the metal ion, see: Ardiwinata et al. (1989), Gryz et al. (2003, 2004, 2006). Centrosymmetric dimeric molecules, each with a different bridging mode, have been reported in the structure of a calcium(II) complex (Starosta & Leciejewicz, 2007), a uranyl complex Leciejewicz & Starosta (2009) as well as in the structure of a lead(II) complex with pyridazine-4-carboxylate ligands (Starosta & Leciejewicz, 2009). For the structure of pyridazine-3-carboxylic acid hydrochloride, see: Gryz et al. (2003).

Experimental top

2 mmols of pyridazine-3-carboxylic acid dissolved in 50 ml of hot water were boiled under reflux for three hours with small excess of lead hydroxide. After cooling to room temperature the mixture was filtered and left for crystallization. After evaporation to dryness, colourless single crystals were found on the bottom of the reaction vessel. They were separated, washed with cold ethanol and dried in air.

Structure description top

For the structures of 3d-metal and Mg(II) complexes with pyridazine-3-carboxylate and water ligands containing monomeric molecules with an octahedral enviroment for the metal ion, see: Ardiwinata et al. (1989), Gryz et al. (2003, 2004, 2006). Centrosymmetric dimeric molecules, each with a different bridging mode, have been reported in the structure of a calcium(II) complex (Starosta & Leciejewicz, 2007), a uranyl complex Leciejewicz & Starosta (2009) as well as in the structure of a lead(II) complex with pyridazine-4-carboxylate ligands (Starosta & Leciejewicz, 2009). For the structure of pyridazine-3-carboxylic acid hydrochloride, see: Gryz et al. (2003).

Computing details top

Data collection: KM-4 Software (Kuma, 1996); cell refinement: KM-4 Software (Kuma, 1996); data reduction: DATAPROC (Kuma, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. A structural unit of (1) with atom labelling scheme and 50% probability displacement ellipsoids.
	Fig. 2. The alignement of two ribbons in the structure.

catena-Poly[lead(II)-bis(µ₂-pyridazine-3-carboxylato- κ³N²,O:O)] top

Crystal data top

[Pb(C₅H₃N₂O₂)₂]	F(000) = 832
M_r = 453.38	D_x = 2.627 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 8.0336 (16) Å	Cell parameters from 25 reflections
b = 10.386 (2) Å	θ = 6–15°
c = 13.766 (3) Å	µ = 14.74 mm⁻¹
β = 93.72 (3)°	T = 293 K
V = 1146.2 (4) Å³	Blocks, colourless
Z = 4	0.33 × 0.09 × 0.08 mm

Data collection top

Kuma KM-4 four-circle diffractometer	2119 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.040
Graphite monochromator	θ_max = 30.1°, θ_min = 2.5°
profile data from ω/2θ scans	h = 0→11
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = 0→14
T_min = 0.284, T_max = 0.379	l = −19→19
3587 measured reflections	3 standard reflections every 200 reflections
3365 independent reflections	intensity decay: 1.3%

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0903P)²] where P = (F_o² + 2F_c²)/3
3365 reflections	(Δ/σ)_max = 0.002
172 parameters	Δρ_max = 6.57 e Å⁻³
0 restraints	Δρ_min = −4.30 e Å⁻³

Crystal data top

[Pb(C₅H₃N₂O₂)₂]	V = 1146.2 (4) Å³
M_r = 453.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0336 (16) Å	µ = 14.74 mm⁻¹
b = 10.386 (2) Å	T = 293 K
c = 13.766 (3) Å	0.33 × 0.09 × 0.08 mm
β = 93.72 (3)°

Data collection top

Kuma KM-4 four-circle diffractometer	2119 reflections with I > 2σ(I)
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	R_int = 0.040
T_min = 0.284, T_max = 0.379	3 standard reflections every 200 reflections
3587 measured reflections	intensity decay: 1.3%
3365 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.137	H-atom parameters constrained
S = 1.05	Δρ_max = 6.57 e Å⁻³
3365 reflections	Δρ_min = −4.30 e Å⁻³
172 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
Pb1	0.25237 (3)	1.03613 (3)	1.006155 (19)	0.02242 (12)
O11	0.0180 (7)	0.9406 (6)	0.8924 (4)	0.0250 (12)
N12	0.3296 (8)	0.8553 (6)	0.8814 (5)	0.0224 (13)
N22	0.1664 (8)	0.8074 (6)	1.0764 (5)	0.0214 (13)
O21	0.4781 (8)	0.9011 (6)	1.0862 (5)	0.0301 (13)
N21	0.0078 (8)	0.7670 (7)	1.0745 (5)	0.0259 (15)
O12	−0.0827 (8)	0.7546 (6)	0.8339 (6)	0.0388 (17)
O22	0.5838 (9)	0.7035 (7)	1.1022 (7)	0.052 (2)
N11	0.4876 (9)	0.8212 (8)	0.8732 (6)	0.0291 (16)
C16	0.5237 (12)	0.7161 (9)	0.8257 (7)	0.033 (2)
H16	0.6349	0.6937	0.8203	0.039*
C14	0.2380 (10)	0.6694 (8)	0.7923 (6)	0.0257 (16)
H14	0.1517	0.6183	0.7656	0.031*
C26	−0.0251 (11)	0.6477 (9)	1.0961 (7)	0.0311 (19)
H26	−0.1358	0.6214	1.0959	0.037*
C17	0.0322 (10)	0.8273 (8)	0.8564 (6)	0.0207 (15)
C13	0.2049 (9)	0.7810 (7)	0.8424 (5)	0.0182 (14)
C23	0.2885 (10)	0.7262 (8)	1.0976 (6)	0.0260 (17)
C15	0.3974 (11)	0.6369 (9)	0.7831 (6)	0.0316 (19)
H15	0.4240	0.5631	0.7492	0.038*
C27	0.4639 (10)	0.7783 (8)	1.0958 (6)	0.0256 (17)
C24	0.2584 (14)	0.5976 (9)	1.1172 (9)	0.047 (3)
H24	0.3460	0.5399	1.1286	0.056*
C25	0.1003 (13)	0.5593 (10)	1.1192 (9)	0.045 (3)
H25	0.0747	0.4751	1.1357	0.055*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Pb1	0.01425 (17)	0.01657 (17)	0.03658 (19)	−0.00057 (14)	0.00282 (11)	−0.00095 (13)
O11	0.016 (3)	0.019 (3)	0.041 (3)	0.004 (2)	0.008 (2)	0.000 (2)
N12	0.013 (3)	0.018 (3)	0.037 (3)	0.001 (3)	0.004 (3)	−0.005 (3)
N22	0.018 (3)	0.014 (3)	0.032 (3)	0.000 (3)	0.005 (2)	0.007 (2)
O21	0.025 (3)	0.018 (3)	0.048 (3)	−0.008 (3)	0.004 (3)	0.004 (3)
N21	0.006 (3)	0.027 (4)	0.045 (4)	−0.005 (3)	0.003 (3)	0.008 (3)
O12	0.011 (3)	0.027 (3)	0.078 (5)	−0.006 (3)	0.004 (3)	−0.010 (3)
O22	0.024 (4)	0.030 (4)	0.101 (6)	0.012 (3)	0.002 (4)	0.001 (4)
N11	0.017 (4)	0.030 (4)	0.040 (4)	−0.004 (3)	0.003 (3)	−0.012 (3)
C16	0.022 (4)	0.028 (5)	0.048 (5)	0.012 (4)	−0.001 (4)	−0.007 (4)
C14	0.017 (4)	0.020 (4)	0.040 (4)	0.000 (3)	0.002 (3)	−0.007 (3)
C26	0.019 (4)	0.022 (4)	0.051 (5)	−0.009 (4)	0.000 (4)	0.008 (4)
C17	0.017 (4)	0.016 (4)	0.030 (4)	0.005 (3)	0.002 (3)	−0.002 (3)
C13	0.013 (3)	0.014 (3)	0.027 (3)	−0.002 (3)	0.000 (3)	−0.001 (3)
C23	0.017 (4)	0.017 (4)	0.045 (4)	−0.004 (3)	0.005 (3)	0.007 (3)
C15	0.022 (4)	0.033 (5)	0.040 (4)	0.004 (4)	0.009 (3)	−0.016 (4)
C27	0.010 (4)	0.024 (4)	0.044 (4)	0.001 (3)	0.004 (3)	−0.002 (3)
C24	0.031 (5)	0.014 (4)	0.093 (8)	0.005 (4)	−0.008 (5)	0.017 (5)
C25	0.028 (6)	0.017 (5)	0.092 (8)	0.001 (4)	0.010 (5)	0.012 (5)

Geometric parameters (Å, º) top

Pb1—O21	2.492 (7)	O22—C27	1.237 (10)
Pb1—O11	2.569 (6)	N11—C16	1.315 (12)
Pb1—N12	2.645 (7)	C16—C15	1.405 (12)
Pb1—O21ⁱ	2.662 (7)	C16—H16	0.9300
Pb1—O11ⁱⁱ	2.669 (6)	C14—C15	1.338 (12)
Pb1—N22	2.672 (6)	C14—C13	1.384 (11)
O11—C17	1.285 (10)	C14—H14	0.9300
O11—Pb1ⁱⁱ	2.669 (6)	C26—C25	1.385 (13)
N12—N11	1.330 (10)	C26—H26	0.9300
N12—C13	1.348 (9)	C17—C13	1.493 (11)
N22—C23	1.312 (10)	C23—C24	1.386 (12)
N22—N21	1.340 (9)	C23—C27	1.511 (12)
O21—C27	1.289 (10)	C15—H15	0.9300
O21—Pb1ⁱ	2.662 (7)	C24—C25	1.334 (14)
N21—C26	1.305 (11)	C24—H24	0.9300
O12—C17	1.217 (10)	C25—H25	0.9300

O21—Pb1—O11	122.4 (2)	N11—C16—H16	119.4
O21—Pb1—N12	72.1 (2)	C15—C16—H16	119.4
O11—Pb1—N12	61.55 (19)	C15—C14—C13	118.4 (8)
O21—Pb1—O21ⁱ	76.0 (2)	C15—C14—H14	120.8
O11—Pb1—O21ⁱ	112.9 (2)	C13—C14—H14	120.8
N12—Pb1—O21ⁱ	68.4 (2)	N21—C26—C25	121.8 (9)
O21—Pb1—O11ⁱⁱ	114.4 (2)	N21—C26—H26	119.1
O11—Pb1—O11ⁱⁱ	76.4 (2)	C25—C26—H26	119.1
N12—Pb1—O11ⁱⁱ	129.6 (2)	O12—C17—O11	125.6 (8)
O21ⁱ—Pb1—O11ⁱⁱ	160.5 (2)	O12—C17—C13	117.6 (7)
O21—Pb1—N22	62.5 (2)	O11—C17—C13	116.8 (7)
O11—Pb1—N22	71.4 (2)	N12—C13—C14	121.1 (7)
N12—Pb1—N22	71.4 (2)	N12—C13—C17	115.9 (6)
O21ⁱ—Pb1—N22	128.9 (2)	C14—C13—C17	123.0 (7)
O11ⁱⁱ—Pb1—N22	69.7 (2)	N22—C23—C24	121.7 (8)
C17—O11—Pb1	120.6 (5)	N22—C23—C27	116.8 (7)
C17—O11—Pb1ⁱⁱ	112.3 (5)	C24—C23—C27	121.5 (8)
Pb1—O11—Pb1ⁱⁱ	103.6 (2)	C14—C15—C16	118.9 (8)
N11—N12—C13	120.1 (7)	C14—C15—H15	120.6
N11—N12—Pb1	120.6 (5)	C16—C15—H15	120.6
C13—N12—Pb1	117.8 (5)	O22—C27—O21	123.7 (8)
C23—N22—N21	119.9 (7)	O22—C27—C23	119.8 (8)
C23—N22—Pb1	116.4 (5)	O21—C27—C23	116.5 (7)
N21—N22—Pb1	122.6 (5)	C25—C24—C23	118.0 (9)
C27—O21—Pb1	122.4 (5)	C25—C24—H24	121.0
C27—O21—Pb1ⁱ	111.8 (6)	C23—C24—H24	121.0
Pb1—O21—Pb1ⁱ	104.0 (2)	C24—C25—C26	118.5 (9)
C26—N21—N22	120.0 (8)	C24—C25—H25	120.8
C16—N11—N12	120.4 (7)	C26—C25—H25	120.8
N11—C16—C15	121.1 (8)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O12ⁱⁱⁱ	0.93	2.35	3.182 (12)	149
C14—H14···O21^iv	0.93	2.76	3.489 (10)	136
C26—H26···O22^v	0.93	2.42	3.201 (12)	142
C15—H15···O11^vi	0.93	2.40	3.266 (10)	155
C25—H25···O12^vii	0.93	2.42	3.328 (12)	165

Symmetry codes: (iii) x+1, y, z; (iv) x−1/2, −y+3/2, z−1/2; (v) x−1, y, z; (vi) −x+1/2, y−1/2, −z+3/2; (vii) −x, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	[Pb(C₅H₃N₂O₂)₂]
M_r	453.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	8.0336 (16), 10.386 (2), 13.766 (3)
β (°)	93.72 (3)
V (Å³)	1146.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	14.74
Crystal size (mm)	0.33 × 0.09 × 0.08

Data collection
Diffractometer	Kuma KM-4 four-circle diffractometer
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.284, 0.379
No. of measured, independent and observed [I > 2σ(I)] reflections	3587, 3365, 2119
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.137, 1.05
No. of reflections	3365
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	6.57, −4.30

Computer programs: KM-4 Software (Kuma, 1996), DATAPROC (Kuma, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Pb1—O21	2.492 (7)	Pb1—O21ⁱ	2.662 (7)
Pb1—O11	2.569 (6)	Pb1—O11ⁱⁱ	2.669 (6)
Pb1—N12	2.645 (7)	Pb1—N22	2.672 (6)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C16—H16···O12ⁱⁱⁱ	0.93	2.35	3.182 (12)	148.5
C14—H14···O21^iv	0.93	2.76	3.489 (10)	135.6
C26—H26···O22^v	0.93	2.42	3.201 (12)	142.2
C15—H15···O11^vi	0.93	2.40	3.266 (10)	155.4
C25—H25···O12^vii	0.93	2.42	3.328 (12)	164.8

Symmetry codes: (iii) x+1, y, z; (iv) x−1/2, −y+3/2, z−1/2; (v) x−1, y, z; (vi) −x+1/2, y−1/2, −z+3/2; (vii) −x, −y+1, −z+2.

References

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