Diaqua­bis­[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl-κN 3)nicotinato-κN]manganese(II)

Peng Gao; Ji-Zhong Liu; Zhong Zhang; Zhong-Jing Huang

doi:10.1107/S1600536810048506

. 2010 Nov 27;66(Pt 12):m1668. doi: 10.1107/S1600536810048506

Diaquabis[2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl-κN ³)nicotinato-κN]manganese(II)

Peng Gao ^a, Ji-Zhong Liu ^a, Zhong Zhang ^a, Zhong-Jing Huang ^a,^*

PMCID: PMC3011436 PMID: 21589328

Abstract

In the title compound, [Mn(C₁₃H₁₄N₃O₃)₂(H₂O)₂], the Mn^II ion is coordinated by four N atoms from two (±)-2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H-imidazol-2-yl)nicotinate ligands and two water molecules in a distorted octahedral environment. Intermolecular O—H⋯O hydrogen bonds lead to a chain along [010]. Intramolecular N—H⋯O and O—H⋯O hydrogen bonds are observed.

Related literature

For coordination compounds with pyridinecarboxylic acids, see: Chatterjee et al. (1998 ▶); Nathan & Mai (2000 ▶); Park et al. (2007 ▶); Yang et al. (2002 ▶). For the synthesis of compounds containing imidazolidinone derivatives, see: Erre et al. (1998 ▶).

Experimental

Crystal data

[Mn(C₁₃H₁₄N₃O₃)₂(H₂O)₂]
M _r = 611.52
Orthorhombic,
a = 12.620 (3) Å
b = 19.753 (4) Å
c = 23.017 (5) Å
V = 5738 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.52 mm⁻¹
T = 298 K
0.50 × 0.48 × 0.35 mm

Data collection

Bruker SMART 1000 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.782, T _max = 0.839
25491 measured reflections
5057 independent reflections
3208 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.057
wR(F ²) = 0.179
S = 1.06
5057 reflections
376 parameters
5 restraints
H-atom parameters constrained
Δρ_max = 1.08 e Å⁻³
Δρ_min = −0.47 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/S1600536810048506/hy2382sup1.cif

e-66-m1668-sup1.cif^{(27.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810048506/hy2382Isup2.hkl

e-66-m1668-Isup2.hkl^{(247.8KB, 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
N2—H2⋯O2	0.86	1.74	2.524 (5)	151
N5—H5⋯O5	0.86	1.76	2.535 (6)	149
O7—H7A⋯O3	0.85	2.09	2.838 (5)	147
O7—H7B⋯O1ⁱ	0.85	1.80	2.638 (5)	170
O8—H8A⋯O6	0.85	2.06	2.791 (5)	143
O8—H8B⋯O4ⁱⁱ	0.85	1.77	2.609 (5)	171

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

Acknowledgments

This work was supported by the Innovation Project of Guangxi University for Nationalities (gxun-chx2009080).

supplementary crystallographic information

Comment

(±)-2-(4-Isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl) nicotinic acid (imina) is a novel pyridylimidazolidinone ligand, which provides with efficient metal-chelating ability. The pyridine carboxylic acids have been extensively used in the design of coordination compounds, due to a variety of bonding modes and ability to form strong hydrogen bonds (Chatterjee et al., 1998; Nathan & Mai, 2000; Park et al., 2007; Yang et al., 2002). Imidazole group, which is one of the polydentate amine ligands, generally coordinates to metal ions using N atoms as donors. The synthesis of imina and its manganese(II) complex has been reported (Erre et al., 1998). Here we present the structure of a manganese(II) complex with 2-(5-isopropyl-5-methyl-4-oxo-4,5-dihydro-1H- imidazol-2-yl)nicotinate (L) ligand.

The molecular structure of the title complex is shown in Fig. 1. The asymmetric unit contains one Mn^II atom, two L ligands and two coordinated water molecules. The Mn^II atom exhibits a distorted octahedral geometry, defined by four N atoms from two L ligands and two O atoms from two water molecules. The dihedral angle between the two L planes in the complex is 61.58 (9)°. Intramolecular N—H···O and O—H···O hydrogen bonds are observed (Table 1). The complex molecules are connected via intermolecular O—H···O hydrogen bonds, forming a one-dimensional chain (Fig. 2).

Experimental

A mixture of Mn(CH₃CO₂)₂.4H₂O (0.122 g, 0.5 mmol), imina (0.392 g, 0.5 mmol), DMF (5 ml) and H₂O (15 ml) was heated in a Teflon-lined steel bomb at 423 K for 3 d. Yellow crystals were obtained by slow evaporation of the solution at room temperature (yield: 78% ). Analysis, calculated for C₂₆H₃₂MnN₆O₈: C 51.07, H 5.27, N 13.74%; found: C 51.02, H 5.23, N 13.70%.