Bis[[(6-carb­oxy­pyridazine-3-carboxyl­ato-κ2N2,O3)lithium]-μ-penta­hydrogen­dioxy­gen(1+)]

Starosta, W.; Leciejewicz, J.

doi:10.1107/S1600536810039176

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Pages m1362-m1363

https://doi.org/10.1107/S1600536810039176

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Bis[[(6-carboxypyridazine-3-carboxylato-κ²N²,O³)lithium]-μ-pentahydrogendioxygen(1+)]

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 3 September 2010; accepted 30 September 2010; online 9 October 2010)

The structure of the title compound, [Li(C₆H₃N₂O₄)₂(H₅O₂)], is composed of centrosymmetric monomers in which an Li^I ion is chelated by two N,O-bonding groups donated by two ligands. The Li^I ion and both ligand molecules are coplanar [r.m.s. deviation 0.0047 (2) Å] and water O atoms are in the axial positions. The second carboxyl group of each ligand remains protonated. An additional H atom, located between adjacent coordinated water molecules and observed on Fourier maps, maintains the charge balance within the monomers and bridges them by short symmetric hydrogen bonds of 2.518 (3) Å to form catenated ribbons. The monomers also interact via hydrogen bonds in which water and carboxyl O atoms act as donors.

Related literature

For the crystal structures of 3d metal complexes with pyridazine-3,6-dicarboxylate and water ligands, see: El Gueddi et al. (1996 ); Escuer et al. (1997 ); Gryz et al. (2006 ); Sun et al. (2007 , 2008 ). For the structures of complexes with Mg^II, see: Gryz et al. (2004 ). For the structures of complexes with Pb^II, see: Sobanska et al. (1999 ). For the structures of both modifications of pyridazine-3,6-dicarboxylic acid, see: Suecur et al. (1987 ); Starosta & Leciejewicz (2004 ).

Experimental

Crystal data

[Li(C₆H₃N₂O₄)₂(H₅O₂)]
M_r = 378.19
Monoclinic, P 2₁ /n
a = 4.903 (1) Å
b = 24.640 (5) Å
c = 6.6020 (13) Å
β = 111.60 (3)°
V = 741.6 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 295 K
0.42 × 0.39 × 0.07 mm

Data collection

Kuma KM-4 four-circle diffractometer
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.961, T_max = 0.999
4355 measured reflections
2181 independent reflections
1207 reflections with I > 2σ(I)
R_int = 0.160
3 standard reflections every 200 reflections intensity decay: 0.8%

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.117
S = 1.01
2181 reflections
135 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H63⋯O6ⁱ	1.26	1.26	2.518 (3)	180
O6—H61⋯O1ⁱⁱ	0.84 (2)	1.82 (2)	2.608 (2)	157 (3)
O3—H31⋯O2ⁱⁱⁱ	0.96 (4)	1.56 (4)	2.525 (2)	176 (2)
O6—H62⋯O3^iv	0.82 (2)	2.42 (2)	2.9957 (19)	128 (3)
O6—H62⋯N2^iv	0.82 (2)	1.93 (2)	2.712 (2)	159 (3)
Symmetry codes: (i) -x+1, -y, -z+2; (ii) x+1, y, z; (iii) x+1, y, z-1; (iv) -x+1, -y, -z+1.

Data collection: KM-4 (Kuma, 1996 $[Kuma (1996). KM-4. Kuma Diffraction Ltd, Wrocław, Poland.]$ ); cell refinement: KM-4; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810039176/rk2232sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039176/rk2232Isup2.hkl

checkCIF report

Comment top

Studies of 3d metal complexes with pyridazine-3,6-dicarboxylate and water ligands revealed a variety of structures: from a monomeric anion in an ionic complex [Mg{C₆H₂N₂O₄)₂(H₂O)₂}]^2-(N₂H₆)²⁺ (Gryz et al., 2004) and dimeric molecules as in Ni, Co and Zn complexes (Escuer et al., 1997; Gryz et al., 2006; Sun et al., 2008) to coordination polymers as in Mn^II complexes (El Gueddi et al., 1996; Sun et al., 2007, 2008). The structure of a Pb^II complex shows also a polymeric pattern (Sobanska et al., 1999). The structure of the title compound is composed of monomers in which a Li^I ion located in a centre of symmetry is chelated by two N,O bonding groups donated by two symmetry related ligand molecules and by two symmetry related aqua O atoms in axial positions. The coordination is slightly distorted octahedral. The ligand molecules and a Li^I ion are coplanar [r.m.s. 0.0047 (2) Å]. The second carboxylic group of each ligand remains protonated and makes an angle of 5.9 (1)° with the pyridazine plane. Bond lengths and angles within the ligand ring are close to those reported earlier for both structures of the parent acid (Suecur et al., 1987; Starosta & Leciejewicz, 2004). An additional proton in a special position located between coordinated water molecules is clearly observed on Fourier maps. It maintains the charge balance within monomers and bridges them by short symmetric hydrogen bonds of 2.518 (3) Å with O6—H63—O6⁽ⁱⁱ⁾ angle of 180° to form catenated ribbons. Symmetry code: (ii) -x + 1, -y, -z + 2. The latter are held together via hydrogen bonds in which water and protonated carboxylate O atoms act as donors and carboxylate O atoms and hetero-N atoms in adjacent ribbons as acceptors.

Related literature top

For the crystal structures of 3d metal complexes with pyridazine-3,6-dicarboxylate and water ligands, see: El Gueddi et al. (1996); Escuer et al. (1997); Gryz et al. (2006); Sun et al. (2007, 2008). For the structures of complexes with Mg^II, see: Gryz et al. (2004). For the structures of complexes with Pb^II, see: Sobanska et al. (1999). For the structures of both modifications of pyridazine-3,6-dicarboxylic acid, see: Suecur et al. (1987); Starosta & Leciejewicz (2004).

Experimental top

The title compound was synthesized by mixing of boiling aqueous solutions, one containing 1 mmol of pyridazine-3,6-dicarboxylic acid, the other - 1 mmol of lithium hydroxide (Aldrich). The mixture was boiled under reflux for 3 h and after cooling to room temperature, filtered and left to crystallize. Few days later, colourless single crystals in the form of thin plates were found after evaporation to dryness. They were extracted, washed with cold ethanol and dried in the air.

Structure description top

For the crystal structures of 3d metal complexes with pyridazine-3,6-dicarboxylate and water ligands, see: El Gueddi et al. (1996); Escuer et al. (1997); Gryz et al. (2006); Sun et al. (2007, 2008). For the structures of complexes with Mg^II, see: Gryz et al. (2004). For the structures of complexes with Pb^II, see: Sobanska et al. (1999). For the structures of both modifications of pyridazine-3,6-dicarboxylic acid, see: Suecur et al. (1987); Starosta & Leciejewicz (2004).

Computing details top

Data collection: KM-4 (Kuma, 1996); cell refinement: KM-4 (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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. A structural unit of title compound with atom labelling scheme. Displacement ellipsoids are drawn at 50% probability level. Symmetry codes: (i) -x, -y, -z + 1; (ii) -x + 1, -y, -z + 2.
	Fig. 2. Packing diagram of the structure.

Bis[[(6-carboxypyridazine-3-carboxylato- κ²N²,O³)lithium]-µ-pentahydrogendioxygen(1+)] top

Crystal data top

[Li(C₆H₃N₂O₄)₂(H₅O₂)]	F(000) = 388
M_r = 378.19	D_x = 1.694 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 4.903 (1) Å	Cell parameters from 25 reflections
b = 24.640 (5) Å	θ = 6–15°
c = 6.6020 (13) Å	µ = 0.15 mm⁻¹
β = 111.60 (3)°	T = 295 K
V = 741.6 (3) Å³	Plate, colourless
Z = 2	0.42 × 0.39 × 0.07 mm

Data collection top

Kuma KM-4 four-circle diffractometer	1207 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.160
Graphite monochromator	θ_max = 30.1°, θ_min = 1.7°
profile data from ω/2θ–scans	h = −6→6
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	k = 0→34
T_min = 0.961, T_max = 0.999	l = −9→9
4355 measured reflections	3 standard reflections every 200 reflections
2181 independent reflections	intensity decay: 0.8%

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.0251P)² + 0.0008P] where P = (F_o² + 2F_c²)/3
2181 reflections	(Δ/σ)_max < 0.001
135 parameters	Δρ_max = 0.40 e Å⁻³
3 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

[Li(C₆H₃N₂O₄)₂(H₅O₂)]	V = 741.6 (3) Å³
M_r = 378.19	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 4.903 (1) Å	µ = 0.15 mm⁻¹
b = 24.640 (5) Å	T = 295 K
c = 6.6020 (13) Å	0.42 × 0.39 × 0.07 mm
β = 111.60 (3)°

Data collection top

Kuma KM-4 four-circle diffractometer	1207 reflections with I > 2σ(I)
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)	R_int = 0.160
T_min = 0.961, T_max = 0.999	3 standard reflections every 200 reflections
4355 measured reflections	intensity decay: 0.8%
2181 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	3 restraints
wR(F²) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.40 e Å⁻³
2181 reflections	Δρ_min = −0.31 e Å⁻³
135 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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
N1	0.1189 (4)	0.08134 (5)	0.4137 (2)	0.0216 (3)
O1	−0.1491 (4)	0.04967 (4)	0.6760 (2)	0.0308 (3)
O3	0.5111 (3)	0.11620 (5)	0.0040 (2)	0.0288 (3)
O2	−0.2209 (3)	0.13593 (5)	0.7509 (2)	0.0297 (3)
C5	0.2683 (4)	0.14735 (6)	0.2292 (3)	0.0208 (4)
N2	0.2452 (4)	0.09550 (5)	0.2750 (2)	0.0215 (3)
C2	0.0209 (4)	0.11977 (6)	0.5110 (2)	0.0196 (3)
C7	−0.1279 (4)	0.10016 (6)	0.6606 (2)	0.0208 (4)
C8	0.4088 (4)	0.15946 (6)	0.0675 (3)	0.0226 (4)
O4	0.4208 (4)	0.20499 (4)	0.0057 (2)	0.0405 (4)
C4	0.1727 (5)	0.18911 (6)	0.3287 (3)	0.0264 (4)
H4	0.1930	0.2253	0.2965	0.032*
C3	0.0479 (5)	0.17513 (6)	0.4753 (3)	0.0253 (4)
H3	−0.0165	0.2014	0.5486	0.030*
Li1	0.0000	0.0000	0.5000	0.0588 (19)
O6	0.4949 (4)	−0.00562 (5)	0.8091 (2)	0.0415 (4)
H61	0.606 (6)	0.0181 (8)	0.792 (4)	0.062*
H62	0.558 (6)	−0.0364 (7)	0.807 (4)	0.062*
H31	0.617 (7)	0.1250 (8)	−0.089 (4)	0.042 (7)*
H63	0.5000	0.0000	1.0000	0.080 (14)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0282 (8)	0.0198 (6)	0.0270 (7)	0.0007 (5)	0.0221 (6)	0.0017 (5)
O1	0.0433 (9)	0.0227 (5)	0.0420 (7)	−0.0012 (5)	0.0339 (6)	0.0023 (5)
O3	0.0415 (9)	0.0237 (5)	0.0362 (7)	0.0014 (5)	0.0319 (6)	0.0020 (5)
O2	0.0401 (9)	0.0289 (6)	0.0350 (7)	0.0004 (5)	0.0311 (5)	−0.0016 (4)
C5	0.0247 (9)	0.0204 (6)	0.0235 (7)	−0.0007 (7)	0.0160 (6)	0.0004 (5)
N2	0.0295 (9)	0.0200 (5)	0.0245 (7)	0.0004 (6)	0.0211 (6)	0.0018 (5)
C2	0.0234 (9)	0.0205 (6)	0.0215 (7)	−0.0009 (6)	0.0162 (6)	0.0000 (5)
C7	0.0215 (9)	0.0260 (7)	0.0221 (7)	−0.0010 (6)	0.0162 (6)	0.0000 (5)
C8	0.0289 (10)	0.0216 (7)	0.0243 (7)	−0.0016 (6)	0.0182 (7)	−0.0013 (5)
O4	0.0689 (11)	0.0230 (6)	0.0506 (8)	−0.0029 (7)	0.0465 (7)	0.0046 (5)
C4	0.0384 (12)	0.0187 (6)	0.0308 (9)	0.0008 (7)	0.0229 (8)	0.0013 (6)
C3	0.0352 (11)	0.0195 (7)	0.0312 (9)	0.0001 (7)	0.0239 (7)	−0.0029 (6)
Li1	0.108 (6)	0.0194 (19)	0.095 (4)	−0.006 (3)	0.091 (4)	−0.001 (2)
O6	0.0709 (13)	0.0209 (6)	0.0542 (9)	−0.0033 (6)	0.0484 (8)	0.0009 (5)

Geometric parameters (Å, º) top

N1—N2	1.327 (2)	C2—C7	1.507 (3)
N1—C2	1.330 (2)	C8—O4	1.2024 (19)
N1—Li1	2.2194 (14)	C4—C3	1.366 (3)
O1—C7	1.2558 (18)	C4—H4	0.9300
O1—Li1	2.0019 (15)	C3—H3	0.9300
O3—C8	1.311 (2)	Li1—O1ⁱ	2.0020 (15)
O3—H31	0.96 (4)	Li1—N1ⁱ	2.2195 (14)
O2—C7	1.241 (2)	Li1—O6	2.535 (2)
C5—N2	1.3274 (19)	Li1—O6ⁱ	2.535 (2)
C5—C4	1.392 (2)	O6—H61	0.836 (18)
C5—C8	1.498 (3)	O6—H62	0.822 (16)
C2—C3	1.399 (2)	O6—H63	1.2600

N2—N1—C2	119.32 (13)	C2—C3—H3	121.3
N2—N1—Li1	130.38 (11)	O1—Li1—O1ⁱ	180.0
C2—N1—Li1	110.08 (12)	O1—Li1—N1	77.50 (6)
C7—O1—Li1	119.98 (14)	O1ⁱ—Li1—N1	102.50 (6)
C8—O3—H31	112.3 (14)	O1—Li1—N1ⁱ	102.50 (6)
N2—C5—C4	122.17 (19)	O1ⁱ—Li1—N1ⁱ	77.50 (6)
N2—C5—C8	117.00 (16)	N1—Li1—N1ⁱ	180.0
C4—C5—C8	120.82 (14)	O1—Li1—O6	90.68 (6)
C5—N2—N1	120.70 (16)	O1ⁱ—Li1—O6	89.32 (6)
N1—C2—C3	122.66 (18)	N1—Li1—O6	89.54 (5)
N1—C2—C7	115.88 (13)	N1ⁱ—Li1—O6	90.46 (5)
C3—C2—C7	121.45 (17)	O1—Li1—O6ⁱ	89.32 (6)
O2—C7—O1	127.48 (19)	O1ⁱ—Li1—O6ⁱ	90.68 (6)
O2—C7—C2	116.05 (14)	N1—Li1—O6ⁱ	90.46 (5)
O1—C7—C2	116.45 (16)	N1ⁱ—Li1—O6ⁱ	89.54 (5)
O4—C8—O3	125.3 (2)	O6—Li1—O6ⁱ	180.0
O4—C8—C5	121.33 (18)	Li1—O6—H61	109.5 (17)
O3—C8—C5	113.34 (14)	Li1—O6—H62	106.8 (17)
C3—C4—C5	117.69 (15)	H61—O6—H62	112 (3)
C3—C4—H4	121.2	Li1—O6—H63	117.00
C5—C4—H4	121.2	H61—O6—H63	107.00
C4—C3—C2	117.40 (17)	H62—O6—H63	104.00
C4—C3—H3	121.3

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H63···O6ⁱⁱ	1.26	1.26	2.518 (3)	180
O6—H61···O1ⁱⁱⁱ	0.84 (2)	1.82 (2)	2.608 (2)	157 (3)
O3—H31···O2^iv	0.96 (4)	1.56 (4)	2.525 (2)	176 (2)
O6—H62···O3^v	0.82 (2)	2.42 (2)	2.9957 (19)	128 (3)
O6—H62···N2^v	0.82 (2)	1.93 (2)	2.712 (2)	159 (3)

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

Experimental details

Crystal data
Chemical formula	[Li(C₆H₃N₂O₄)₂(H₅O₂)]
M_r	378.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	4.903 (1), 24.640 (5), 6.6020 (13)
β (°)	111.60 (3)
V (Å³)	741.6 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.42 × 0.39 × 0.07

Data collection
Diffractometer	Kuma KM-4 four-circle
Absorption correction	Analytical (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.961, 0.999
No. of measured, independent and observed [I > 2σ(I)] reflections	4355, 2181, 1207
R_int	0.160
(sin θ/λ)_max (Å⁻¹)	0.705

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.117, 1.01
No. of reflections	2181
No. of parameters	135
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.31

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H63···O6ⁱ	1.2600	1.2600	2.518 (3)	180.0
O6—H61···O1ⁱⁱ	0.836 (18)	1.82 (2)	2.608 (2)	157 (3)
O3—H31···O2ⁱⁱⁱ	0.96 (4)	1.56 (4)	2.525 (2)	176 (2)
O6—H62···O3^iv	0.822 (16)	2.42 (2)	2.9957 (19)	128 (3)
O6—H62···N2^iv	0.822 (16)	1.93 (2)	2.712 (2)	159 (3)

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

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