4,5-Diphenyl-2-p-tolyl-1H-imidazol-3-ium nitrate

Li-Jing Cui

doi:10.1107/S1600536809018789

. 2009 May 23;65(Pt 6):o1361. doi: 10.1107/S1600536809018789

4,5-Diphenyl-2-p-tolyl-1H-imidazol-3-ium nitrate

Li-Jing Cui ^a,^*

PMCID: PMC2969798 PMID: 21583212

Abstract

In the cation of the title compound, C₂₂H₁₉N₂ ⁺·NO₃ ⁻, the N atom in the 3-position of the imidazole is protonated. The three pendant aromatic rings are twisted from the plane of the imadazolium ring by dihedral angles of 38.1 (1), 43.74 (9) and 20.4 (1)°. In the crystal structure, N—H⋯O and N—H⋯(O,O) hydrogen bonds link the molecules to form an infinite one-dimensional chain parallel to the c axis.

Related literature

For uses of imidazole derivatives, see: Dai & Fu (2008 ▶); Fu & Xiong (2008 ▶); Huang et al. (2008 ▶).

Experimental

Crystal data

C₂₂H₁₉N₂ ⁺·NO₃ ⁻
M _r = 373.40
Orthorhombic,
a = 8.442 (2) Å
b = 12.970 (3) Å
c = 17.098 (3) Å
V = 1872.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.40 × 0.35 × 0.25 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.955, T _max = 1.000 (expected range = 0.934–0.978)
19745 measured reflections
4278 independent reflections
2714 reflections with I > 2σ(I)
R _int = 0.089

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.143
S = 1.03
4278 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL/PC.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809018789/im2112sup1.cif

e-65-o1361-sup1.cif^{(18.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018789/im2112Isup2.hkl

e-65-o1361-Isup2.hkl^{(209.7KB, 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—H2A⋯O1ⁱ	0.86	2.05	2.905 (4)	176
N2—H2A⋯O2ⁱ	0.86	2.39	2.922 (3)	121
N1—H1A⋯O3	0.86	1.96	2.720 (3)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

This work was supported by a start-up grant from Southeast University to Professor Ren-Gen Xiong.

supplementary crystallographic information

Comment

Imidazole 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., 2008; Fu & Xiong, 2008; Dai & Fu, 2008). We report herein the crystal structure of the title compound, 4,5-diphenyl-2-p-tolyl-1H-imidazol-3-ium nitrate.

The title compound contains an organic cation and a nitrate ion in the asymmetric unit. The imidazole N atom in 3-position is protonated. Imidazole and benzene rings are twisted from each other by a dihedral angle of 38.1 (1)°, 43.74 (9)° and 20.4 (1)°. The crystal packing is stabilized by N—H···O hydrogen bonds to form an infinite one-dimensional chain parallel to c axis. (Table 1, Fig. 2).

Experimental

Under nitrogen protection, 1,2-diphenyl-ethane-1,2-dione (20 mmol), 4-methylbenzaldehyde (20 mmol) and amine acetate (50 mmol) were dissolved in 60 ml of HOAc. The mixture was stirred at 110 °C for 20 h. The resulting solution was poured into ice water (200 ml) and after neutralizing the mixture with NaOH (6 mol/l) a white solid was obtained. After filtration and washing with distilled water the crude product was recrystallized from an ethanolic solution (150 ml) to which nitric acid (5 ml) was added to yield colorless block-like crystals of the title compound, suitable for X-ray analysis.