Poly[1H-imidazol-3-ium [di-μ-nitrato-sodium]]

Chahrazed Trifa; Amira Bouhali; Sofiane Bouacida; Chaouki Boudaren; Thierry Bataille

doi:10.1107/S1600536813011951

. 2013 May 11;69(Pt 6):m303–m304. doi: 10.1107/S1600536813011951

Poly[1H-imidazol-3-ium [di-μ-nitrato-sodium]]

Chahrazed Trifa ^a, Amira Bouhali ^a, Sofiane Bouacida ^a,^b,^*, Chaouki Boudaren ^a, Thierry Bataille ^c

PMCID: PMC3684872 PMID: 23794974

Abstract

In the title compound {(C₃H₅N₂)[Na(NO₃)₂]}_n, the Na^I ion is coordinated by eight O atoms from three bidentate nitrate anions and two O atoms from two monodentate nitrate anions, displaying a bicapped trigonal–prismatic geometry. The imidazolium cation is essentially planar (r.m.s. deviation for all non-H atoms = 0.0018 Å). In the crystal, the Na^I ions are connected by bridging nitrate ligands, forming layers parallel to (010). The imidazolium cations are sandwiched between these layers. Weak C—H⋯O hydrogen bonds link the layers into a three-dimensional network. In addtion, π–π interactions between the imidazolium rings [centroid–centroid distance = 3.588 (3) Å] are observed.

Related literature

For applications of imidazole and its derivatives, see: Huang et al. (2008 ▶, 2011 ▶). For the preparation and characterization of some metal complexes of imidazolium, see: Gao et al. (2009 ▶); Zhang et al. (2011 ▶); Zhu (2012 ▶); Han et al. (2007 ▶); Wenyan et al. (2011 ▶).

Experimental

Crystal data

(C₃H₅N₂)[Na(NO₃)₂]
M _r = 216.1
Monoclinic,
a = 3.5875 (3) Å
b = 24.8548 (17) Å
c = 8.819 (6) Å
β = 95.546 (4)°
V = 782.7 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 150 K
0.52 × 0.15 × 0.13 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2002 ▶) T _min = 0.884, T _max = 0.972
9892 measured reflections
1778 independent reflections
1541 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.084
S = 1.10
1778 reflections
127 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and CRYSCAL (T. Roisnel, local program).

Supplementary Material

Click here for additional data file.^{(27KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813011951/lh5609sup1.cif

e-69-0m303-sup1.cif^{(27KB, cif)}

Click here for additional data file.^{(85.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813011951/lh5609Isup2.hkl

e-69-0m303-Isup2.hkl^{(85.8KB, hkl)}

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

Table 1. Selected bond lengths (Å).

Na1—O12	2.4321 (16)
Na1—O21	2.4639 (14)
Na1—O13ⁱ	2.5106 (13)
Na1—O23	2.5338 (13)
Na1—O13ⁱⁱ	2.5730 (14)
Na1—O11ⁱⁱ	2.5910 (19)
Na1—O11	2.6239 (17)
Na1—O21ⁱⁱⁱ	2.6776 (14)

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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
C1—H1⋯O23^iv	0.95	2.50	3.438 (3)	168
C4—H4⋯O11^v	0.95	2.41	3.355 (3)	173

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Symmetry codes: (iv) Inline graphic ; (v) .

Acknowledgments

The authors thank MESRS and ATRST (Algérie) for financial support. They also thank Dr Thierry Roisnel, Centre de Diffractométrie X (CDIFX) de Rennes, Université de Rennes 1, France, for his technical assistance with the data collection.

supplementary crystallographic information

Comment

Knowledge of the detailed coordination behavior of imidazoles and their limitation in the possible use in complexes with specific catalytic activity is of great current importance. Imidazole, namely 1,3-diazacyclopenta-2,4-diene and its derivatives have found wide range of applications in coordination chemistry because of their multiple coordination modes as ligands to metal ions and for the construction of novel metal–organic frameworks (Huang et al. 2011; Huang et al. 2008). Recently, several complexes based on the imidazolium cation were reported (Gao et al. 2009; Zhang et al. 2011; Zhu 2012; Han et al. 2007; Wenyan et al. 2011). This paper describes the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound (I) (Fig. 1) contains one Na^I ion, one protonated imidazole molecule and two coordinated nitrate anions. The Na centre is coordinated by eight O atoms from three bidentate nitrate anions and two O atoms from two monodentate nitrate anions, displaying a bicapped trigonal-prismatic geometry (Fig. 2). The Na—O bond distances range from 2.4321 (16) to 2.6239 (17) Å. The C—N distances lie in the range 1.328 (2)- 1.376 (2) A°. The imidazolium cation is essentially planar giving an r.m.s. deviation for all non-H atoms of 0.0018 A°, with a maximum deviation from the mean plane of -0.0028 (1)Å for the C4 atom. The crystal packing can be described by alterning two-dimensional polymecric layers and double layers of imidazolium ions. A two-dimensional layer structure is thus constructed parallel to (010) (Fig. 3). Weak hydrogen bonds are formed between imidazolium cation and the nitrate O atoms of adjacent layers (Fig. 3) further connect the two-dimensional layers into a three-dimensional network. In addition, π···π contacts between the imidazolium rings, [centroid-centroid distance = 3.588 (3) Å with ca 1.382 Å slippage] are also observed.

Experimental

All chemicals used (reagent grade) were commercially available. The compound was obtained by using hydrothermal method in Teflon-lined autoclave. The mixture of barium nitrate, imidazole, sodium hydroxide and deionized water in the molar ratio 1:1:3:264 was stirred for half an hour, and transferred in a Teflon-lined autoclave, then treated at 423 K for 4 d. After the mixture was slowly cooled to room temperature, colorless needles suitable for X-ray diffraction analysis were collected from the final reaction system by filtration, washed several times with distilled water and dried in air at ambient temperature.