Bis(1-methyl-4-oxoimidazolidin-2-iminium) diaqua­bis­(pyridine-2,4-dicarboxyl­ato-κ2 N,O 2)zincate(II) dihydrate

Hossein Aghabozorg; Fatemeh Jafarbak; Masoud Mirzaei; Behrouz Notash

doi:10.1107/S1600536811008452

. 2011 Mar 12;67(Pt 4):m435–m436. doi: 10.1107/S1600536811008452

Bis(1-methyl-4-oxoimidazolidin-2-iminium) diaquabis(pyridine-2,4-dicarboxylato-κ² N,O ²)zincate(II) dihydrate

Hossein Aghabozorg ^a,^*, Fatemeh Jafarbak ^a, Masoud Mirzaei ^b, Behrouz Notash ^c

PMCID: PMC3099900 PMID: 21753959

Abstract

In the title compound, (C₄H₈N₃O)₂[Zn(C₇H₃NO₄)₂(H₂O)₂]·2H₂O, the Zn^II ion is six-coordinated in a distorted octahedral geometry by two pyridine-2,4-dicarboxylate (pydc) ligands in the equatorial plane and two water molecules in the axial positions. The pydc ligands act as bidentate chelating ligands through one carboxylate O atom and the pyridine N atom. Intermolecular N—H⋯O, O—H⋯O and weak C—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For a review article on proton-transfer compounds, see: Aghabozorg et al. (2008b ▶). For related structures, see: Aghabozorg et al. (2008a ▶,c ▶); Attar Gharamaleki et al. (2009 ▶); Moghimi et al. (2004 ▶, 2005 ▶).

Experimental

Crystal data

(C₄H₈N₃O)₂[Zn(C₇H₃NO₄)₂(H₂O)₂]·2H₂O
M _r = 695.93
Triclinic,
a = 5.3209 (11) Å
b = 8.3893 (17) Å
c = 16.621 (3) Å
α = 81.58 (3)°
β = 85.26 (3)°
γ = 74.09 (3)°
V = 705.1 (3) Å³
Z = 1
Mo Kα radiation
μ = 0.96 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.15 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T _min = 0.793, T _max = 0.862
7743 measured reflections
3787 independent reflections
3206 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.033
wR(F ²) = 0.090
S = 1.05
3787 reflections
226 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.48 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008452/hy2411sup1.cif

e-67-0m435-sup1.cif^{(18.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008452/hy2411Isup2.hkl

e-67-0m435-Isup2.hkl^{(185.6KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3ⁱ	0.91 (3)	1.87 (3)	2.764 (2)	165 (3)
N4—H4A⋯O4ⁱ	0.86	1.86	2.706 (2)	168
N4—H4B⋯O2ⁱⁱ	0.86	1.92	2.771 (2)	169
O5—H5A⋯O4ⁱ	0.79 (2)	1.95 (3)	2.729 (2)	171 (3)
O5—H5B⋯O1ⁱⁱ	0.85 (3)	1.98 (3)	2.8088 (17)	165 (2)
O7—H7A⋯O3	0.73 (4)	2.32 (4)	2.968 (3)	148 (4)
O7—H7B⋯O6ⁱⁱⁱ	0.82 (4)	2.26 (4)	2.993 (3)	149 (4)
C5—H5⋯O5^iv	0.93	2.46	3.308 (2)	152
C11—H11A⋯O2ⁱⁱ	0.96	2.48	3.425 (3)	167

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) .

Acknowledgments

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

supplementary crystallographic information

Comment

Many organic aromatic ligands and metal ions may aggregate into supramolecular networks using coordination and hydrogen bonds and π–π stacking interactions (Aghabozorg et al., 2008b). Metal complexes of pyridine-(di)carboxylates possess versatile structural motifs, which finally aggregate to various supramolecular architectures with interesting properties. We have previously reported several compounds containing creatinine (creat), pyridine-2,6-dicarboxylic acid (pydcH₂) and various metals, such as (creatH)(pydcH).H₂O (Moghimi et al., 2004), (creatH)₂[Bi(pydc)₂]₂.4H₂O (Moghimi et al., 2005), (creatH)[Zn(pydc)(pydcH)].4H₂O (Aghabozorg et al., 2008c), (creatH)[Cr(pydc)₂](pydcH₂).6H₂O (Aghabozorg et al., 2008a) and (H₃O)(creatH)[Ni(pydc)₂].3H₂O (Attar Gharamaleki et al., 2009). For more details and related literature see our recent review article on proton-transfer compounds (Aghabozorg et al., 2008b).

We describe here the crystal structure of the title compound. The compound contains a [Zn(pydc)₂(H₂O)₂]^2- anion, two (creatH)⁺ cations and two uncoordinated water molecules (Fig. 1). In the anion, the Zn^II atom is six-coordinated by two N atoms and two O atoms from two pydc ligands and two water molecules, with the bond length range of 2.0819 (14)–2.1957 (15) Å. The coordination environment around Zn^II is distorted octahedral. Intermolecular N—H···O, O—H···O, and weak C—H···O hydrogen bonds play an important role in the stabilization of the crystal structure (Fig. 2 and Table 1).

Experimental

The reaction of pyridine-2,4-dicarboxylic acid (83 mg, 0.5 mmol) in 10 ml distilled water, creatinine (56 mg, 0.5 mmol) in 5 ml distilled water and Zn(NO₃)₂.4H₂O (65 mg, 0.25 mmol) in 10 ml distilled water in a 2:2:1 molar ratio gave colorless block crystals of the title compound after slow evaporation of the solvent at the room temperature. The crystals obtained were stable in air.