Diaqua­bis(5-carb­oxy-2-propyl-1H-imidazole-4-carboxyl­ato-κ2 N 3,O 4)nickel(II) N,N-dimethyl­formamide disolvate

Shi-Jie Li; Jian-Bin Yan; Wen-Dong Song; Hao Wang; Dong-Liang Miao

doi:10.1107/S1600536810004691

. 2010 Feb 13;66(Pt 3):m280. doi: 10.1107/S1600536810004691

Diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato-κ² N ³,O ⁴)nickel(II) N,N-dimethylformamide disolvate

Shi-Jie Li ^a, Jian-Bin Yan ^a, Wen-Dong Song ^b,^*, Hao Wang ^a, Dong-Liang Miao ^a

PMCID: PMC2983735 PMID: 21580226

Abstract

In the title complex, [Ni(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO, the Ni^II atom is six-coordinated by two N,O-bidentate 5-carboxy-2-propyl-1H-imidazole-4-carboxylate ligands and two water molecules in a distorted octahedral environment. The methyl C and H atoms of the two ligands are disordered over two sets of sites in 0.74 (2):0.26 (2) and 0.57 (8):0.43 (8) ratios. A supramolecular network is stabilized by intra- and intermolecular N—H⋯O and O—H⋯O hydrogen bonds involving the ligands, coordinated water molecules and dimethylformamide solvent molecules.

Related literature

For the structures of related 2-propyl-1H-imidazole-4,5-dicarboxylate complexes, see: Song et al. (2010 ▶); Yan et al. (2010 ▶).

Experimental

Crystal data

[Ni(C₈H₉N₂O₄)₂(H₂O)₂]·2C₃H₇NO
M _r = 635.26
Orthorhombic,
a = 16.3574 (12) Å
b = 9.5246 (7) Å
c = 18.7700 (13) Å
V = 2924.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.73 mm⁻¹
T = 273 K
0.31 × 0.24 × 0.18 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T _min = 0.805, T _max = 0.880
14413 measured reflections
5064 independent reflections
3663 reflections with I > 2σ(I)
R _int = 0.063

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.133
S = 1.03
5064 reflections
403 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.36 e Å⁻³
Absolute structure: Flack (1983 ▶), 2344 Friedel pairs
Flack parameter: 0.01 (2)

Data collection: CrystalStructure (Rigaku/MSC, 2002 ▶); cell refinement: CrystalStructure; data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, 1R. DOI: 10.1107/S1600536810004691/hy2277sup1.cif

e-66-0m280-sup1.cif^{(24.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810004691/hy2277Isup2.hkl

e-66-0m280-Isup2.hkl^{(248KB, 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
O3—H1⋯O2	1.05 (6)	1.42 (6)	2.474 (6)	176 (5)
O7—H7⋯O6	0.82	1.67	2.479 (6)	169
N2—H2⋯O10ⁱ	0.86	1.93	2.780 (6)	171
N4—H4⋯O9	0.86	1.94	2.788 (6)	171
O1W—H1W⋯O8ⁱⁱ	0.85	1.96	2.782 (5)	162
O1W—H2W⋯O10ⁱⁱⁱ	0.85	1.92	2.757 (6)	168
O2W—H3W⋯O4^iv	0.85	1.96	2.794 (5)	166
O2W—H4W⋯O9^v	0.85	1.98	2.800 (6)	163

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

Acknowledgments

The authors acknowledge Guang Dong Ocean University for supporting this work.

supplementary crystallographic information

Comment

2-Propyl-1H-imidazole-4,5-dicarboxylate ligand with efficient N,O-donors has been used to obtain new metal–organic complexes, such as poly[diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ³N³,O⁴,O⁵)calcium(II)] (Song et al., 2010) and [diaquabis(5-carboxy-2-propyl-1H-imidazole-4-carboxylato- κ²N³,O⁴)manganese(II)] N,N-dimethylformamide (Yan et al., 2010). In this paper, we report the synthesis and structure of a new nickel(II) complex obtained under hydrothermal conditions.

As illustrated in Fig. 1, the title complex molecule is composed of one Ni^II ion, two mono-deprotonated 2-propyl-1H-imidazole-4,5-dicarboxylate ligands, two coordinated water molecules and two dimethylformamide solvent molecules. The Ni^II atom exhibits a slightly distorted octahedral coordination geometry, defined by two N,O-bidentate ligands and two water molecules. In the crystal structure, the complex molecules and dimethylformamide solvent molecules are linked by N—H···O and O—H···O hydrogen bonds (Table 1) into a two-dimensional supramolecular structure parallel to (0 0 1) (Fig. 2). The methyl C and H atoms of the two ligands are disordered over two sites in raios of 0.74 (2):0.26 (2) and 0.57 (8):0.43 (8).

Experimental

A mixture of Ni(CH₃CO₂)₂ (0.5 mmol, 0.06 g) and 2-propyl-1H-imidazole-4,5-dicarboxylic acid (0.5 mmol, 0.99 g) in 15 ml of dimethylformamide solution was sealed in an autoclave equipped with a Teflon liner (20 ml) and then heated at 433 K for 4 d. Crystals of the title compound were obtained by slow evaporation of the solvent at room temperature.