Poly[[μ2-aqua-μ3-(4-carb­oxy-2-propyl-1H-imidazole-5-carboxyl­ato-κ4 N 3,O 4:O 4:O 5)-sodium] hemihydrate]

Zhong-Jing Huang; Jin-Niu Tang; Zhi-Rong Luo; Dai-Yin Wang; Huan Wei

doi:10.1107/S1600536811007732

. 2011 Mar 9;67(Pt 4):m408. doi: 10.1107/S1600536811007732

Poly[[μ₂-aqua-μ₃-(4-carboxy-2-propyl-1H-imidazole-5-carboxylato-κ⁴ N ³,O ⁴:O ⁴:O ⁵)-sodium] hemihydrate]

Zhong-Jing Huang ^a,^*, Jin-Niu Tang ^a, Zhi-Rong Luo ^a, Dai-Yin Wang ^a, Huan Wei ^a

PMCID: PMC3099890 PMID: 21753940

Abstract

In the title compound, {[Na(C₈H₉N₂O₄)(H₂O)]·0.5H₂O}_n, the Na⁺ ion is coordinated by two bridging water molecules, one N atom and three O atoms from three 4-carboxy-2-propyl-1H-imidazole-5-carboxylate (H₂pimdc) ligands. Adjacent Na⁺ ions are linked alternately by two water O atoms and two carboxy O atoms into a chain along [001]. These chains are connected through the coordination of the carboxylate O atoms to the Na⁺ ions, forming a three-dimensional structure. An intramolecular O—H⋯O hydrogen bond and intermolecular N—H⋯O and O—H⋯O hydrogen bonds are present in the crystal structure.

Related literature

For the properties and biological activity of imidazole-4,5-dicarboxylic acid and its derivatives, see: Baures (1999 ▶); Bogdanova et al. (1992 ▶); Borodkin et al. (1984 ▶); Reichardt et al. (1992 ▶); Su et al. (2001 ▶).

Experimental

Crystal data

[Na(C₈H₉N₂O₄)(H₂O)]·0.5H₂O
M _r = 247.18
Monoclinic,
a = 15.406 (4) Å
b = 15.478 (4) Å
c = 10.734 (3) Å
β = 118.364 (3)°
V = 2252.4 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.15 mm⁻¹
T = 296 K
0.52 × 0.47 × 0.44 mm

Data collection

Bruker APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.528, T _max = 0.562
5971 measured reflections
1986 independent reflections
1669 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.106
S = 1.10
1986 reflections
152 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811007732/hy2402sup1.cif

e-67-0m408-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811007732/hy2402Isup2.hkl

e-67-0m408-Isup2.hkl^{(97.8KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Na1—O1	2.3658 (15)
Na1—O1ⁱ	2.3644 (14)
Na1—O3ⁱⁱ	2.5550 (15)
Na1—O5	2.4011 (15)
Na1—O5ⁱⁱⁱ	2.3818 (16)
Na1—N1	2.4848 (16)

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

Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3^iv	0.86	2.00	2.8384 (18)	164
O2—H2⋯O4	0.82	1.64	2.4603 (18)	178
O5—H5B⋯O2ⁱ	0.91	2.07	2.9493 (18)	164
O5—H5A⋯O6	0.86	1.97	2.8234 (19)	169
O6—H6C⋯O4ⁱⁱ	0.88	2.03	2.8835 (16)	163

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

Acknowledgments

This work was supported by the Innovation Project of Guangxi University for Nationalities (gxun-chx2010083).

supplementary crystallographic information

Comment

1H-Imidazole and its derivatives are a kind of excellent supramolecular synthons. The N atoms of imidazole can coordinate to metal ions in monodentate or bidentate mode (Su et al., 2001). Imidazole-4,5-dicarboxylic acid and derivatives have been studied in terms of their physical properties as well as for their diverse biological activities (Bogdanova et al., 1992; Borodkin et al., 1984; Reichardt et al., 1992), including the use of imidazole-4,5-dicarboxylic acid amides in the development of human immunodeficiency virus (HIV-1) protease inhibitors (Baures, 1999). Here we present the synthesis and structure of the title complex derived from 2-propyl-1H-imidazole-4,5-dicarboxylic acid. The distinct binding modes of the ligands as well as the coordination preferences of the metal ion are discussed.

In the title compound, the 2-propyl-4-carboxy-1H-imidazole-5-carboxylate (H₂pimdc) ligand is bonded to Na ions in a µ₃-mode. The coordination of Na ion is achieved by two water molecules, one N atom and three O atoms from three H₂pimdc ligands (Fig .1, Table 1). Two O1 atoms of the H₂pimdc ligand bridge two Na atoms, forming a parallelogram and two O5 atoms of the water molecules form another parallelogram with two Na atoms, leading to a chain along [0 0 1]. The chains are connected through the coordination of the carboxylate O3 atoms to the Na ions, forming a three-dimensional structure (Fig. 2). The propyl group becomes an ornament in the coordination network. The crystal structure is stabilized by intramolecular O—H···O hydrogen bond and intermolecular N—H···O and O—H···O hydrogen bonds (Table 2).

Experimental

An ethanol solution (5 ml) containing 2-propyl-1H-imidazole-4,5-dicarboxylic acid (1 mmol, 0.198 g) was added dropwise to a water solution (10 ml) containing NaOH (0.5 mmol, 0.040 g). After stirring for 6 h, the solution was filtered. The filtered solution were evaporated for several days in air and colorless block-shaped crystals suitable for single-crystal X-ray diffraction were obtained (yield: 80% based on the ligand).