2-(3-Nitro­phen­yl)-4,5-diphenyl-1H-imidazol-3-ium chloride

Li-Jing Cui

doi:10.1107/S160053680803002X

. 2008 Sep 24;64(Pt 10):o1987. doi: 10.1107/S160053680803002X

2-(3-Nitrophenyl)-4,5-diphenyl-1H-imidazol-3-ium chloride

Li-Jing Cui ^a,^*

PMCID: PMC2959275 PMID: 21201186

Abstract

The title compound, C₂₁H₁₆N₃O₂ ⁺·Cl⁻, contains two organic cations with similar conformation and two chloride ions in the asymmetric unit. The imidazole and benzene rings are twisted with respect to each other [dihedral angles of 24.05 (16), 24.31 (16) and 50.38 (13) in one cation and 27.70 (15), 25.07 (16) and 45.86 (14)° in the other]. The crystal packing is stabilized by N—H⋯Cl hydrogen bonds, forming an infinite one-dimensional chain parallel to the c axis.

Related literature

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

Experimental

Crystal data

C₂₁H₁₆N₃O₂ ⁺·Cl⁻
M _r = 377.82
Triclinic,
a = 9.7265 (19) Å
b = 12.364 (3) Å
c = 15.511 (3) Å
α = 91.97 (3)°
β = 90.15 (3)°
γ = 95.84 (3)°
V = 1854.5 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.23 mm⁻¹
T = 298 (2) K
0.24 × 0.20 × 0.18 mm

Data collection

Rigaku Mercury2 diffractometer
Absorption correction: multi-scan (CrystalClear, Rigaku, 2005 ▶) T _min = 0.939, T _max = 0.957
18693 measured reflections
8132 independent reflections
5351 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.062
wR(F ²) = 0.153
S = 1.07
8132 reflections
487 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.27 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: ORTEP-3 for Windows (Farrugia, 1997 ▶) and SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680803002X/dn2374sup1.cif

e-64-o1987-sup1.cif^{(25.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680803002X/dn2374Isup2.hkl

e-64-o1987-Isup2.hkl^{(389.8KB, 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
N3—H3⋯Cl1	0.86	2.30	3.066 (2)	148
N5—H5A⋯Cl1	0.86	2.20	3.045 (2)	166
N6—H6⋯Cl2	0.86	2.31	3.061 (2)	146
N2—H2⋯Cl2ⁱ	0.86	2.21	3.048 (2)	163

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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, et al. 2008; Dai & Fu 2008). We report here the crystal structure of the title compound, di-2-(3'-nitrophenyl)-4,5-diphenyl-1H-imidazole-3-ium dichloride.

The title compound contains two organic cation with similar conformation and two Cl^- ions in the asymmetric unit (Fig. 1). In both molecules the N atom of the imidazole is protonated. The imidazole and the benzene rings are twisted from each other by a dihedral angle of 24.05 (0.16) °, 24.31 (0.16) ° and 50.38 (0.13) ° (27.70 (0.15) °, 25.07 (0.16) ° and 45.86 (0.14) °) . The crystal packing is stabilized by N—H···Cl hydrogen bonds to form an infinite one-dimensional chain parallel to the c axis. (Table 1, Fig. 2).

Experimental

Under nitrogen protection, benzil (20 mmol), 3-nitrobenzaldehyde (20 mmol) and amine acetate (50 mmol) were added in a flask. The mixture was stirred at 110 °C for 20 h in the solution of HAC (60 ml). The resulting solution was poured into ice water (200 ml), white solid was obtained after adding NaOH (6 mol/L) till PH=7, then filtered and washed with distilled water. The crude product was recrystallized with the solution of ethanol (150 ml) and hydrochloric acid (5 ml) to yield colorless block-like crystals, suitable for X-ray analysis.