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

Li Zhang

doi:10.1107/S1600536809024325

. 2009 Jul 4;65(Pt 8):o1766. doi: 10.1107/S1600536809024325

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

Li Zhang ^a,^*

PMCID: PMC2977243 PMID: 21583476

Abstract

In the title compound, C₂₂H₁₉N₂ ⁺·ClO₄ ⁻, the three pendant aromatic rings are twisted from the plane of the imidazolium ring by dihedral angles of 17.3 (2), 65.7 (2) and 3.4 (2)°. In the crystal structure, N—H⋯O and N—H⋯(O,O) hydrogen bonds link the ions, forming a ribbon-like structure along the a axis.

Related literature

For general background to imidazole derivatives, see: Fu & Xiong (2008 ▶); Huang et al. (2008 ▶). For applications of metal-organic coordination compounds, see: Fu et al. (2007 ▶, 2008 ▶); Huang et al. (1999 ▶); Liu et al. (1999 ▶); Xie et al. (2003 ▶); Zhang et al. (2000 ▶, 2001 ▶).

Experimental

Crystal data

C₂₂H₁₉N₂ ⁺·ClO₄ ⁻
M _r = 410.84
Monoclinic,
a = 9.1964 (18) Å
b = 9.921 (2) Å
c = 21.489 (4) Å
β = 94.16 (3)°
V = 1955.4 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 K
0.45 × 0.40 × 0.25 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T _min = 0.945, T _max = 1.000 (expected range = 0.893–0.945)
19242 measured reflections
4474 independent reflections
2602 reflections with I > 2σ(I)
R _int = 0.070

Refinement

R[F ² > 2σ(F ²)] = 0.072
wR(F ²) = 0.214
S = 1.04
4474 reflections
271 parameters
24 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.35 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 (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024325/ci2832sup1.cif

e-65-o1766-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809024325/ci2832Isup2.hkl

e-65-o1766-Isup2.hkl^{(219.2KB, 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
N1—H1⋯O3ⁱ	0.89 (4)	2.05 (4)	2.943 (4)	175 (3)
N2—H2⋯O1ⁱⁱ	0.81 (4)	2.33 (4)	3.037 (5)	146 (3)
N2—H2⋯O1ⁱⁱⁱ	0.81 (4)	2.50 (4)	3.196 (5)	145 (3)

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

Acknowledgments

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

supplementary crystallographic information

Comment

The construction of metal-organic coordination compounds has attracted much attention owing to potential functions such as permittivity, fluorescence, magnetism and optical properties (Fu et al., 2007, 2008; Huang et al., 1999; Liu et al., 1999; Xie et al., 2003; Zhang et al., 2000, 2001). Imidazole derivatives are a class of excellent ligands 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). We report here the crystal structure of the title compound, 4,5-diphenyl-2-p-tolyl-1H-imidazolium perchlorate.

The title compound contains an organic cation and a ClO₄^- anion in the asymmetric unit. The imidazole N atom in the 3-position is protonated. The C1-C6, C9-C14 and C17-C22 benzene rings form dihedral angles of 17.3 (2)°, 65.7 (2)° and 3.4 (2)°, respectively, with the imidazolium ring.

The crystal packing is stabilized by N—H···O hydrogen bonds which form a ribbon-like structure extending along the a axis (Table 1 and Fig. 2).

Experimental

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 under nitrogen protection. The mixture was stirred at 383 K 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. The crude product was filtered and washed with distilled water. The crude product was dissolved in ethanol (150 ml)-perchloric acid (1 ml) and recrystallized to yield colourless block-shaped crystals of the title compound.