2-(4,5-Diphenyl-2-p-tolyl-1H-imidazol-1-yl)-3-phenyl­propan-1-ol

Yongmei Xiao; Liangru Yang; Kun He; Jinwei Yuan; Pu Mao

doi:10.1107/S1600536811054766

. 2012 Jan 7;68(Pt 2):o264. doi: 10.1107/S1600536811054766

2-(4,5-Diphenyl-2-p-tolyl-1H-imidazol-1-yl)-3-phenylpropan-1-ol

Yongmei Xiao ^a, Liangru Yang ^a, Kun He ^a, Jinwei Yuan ^a, Pu Mao ^a,^*

PMCID: PMC3274963 PMID: 22346908

Abstract

In the title compound, C₃₁H₂₈N₂O, the dihedral angles formed by the imidazole ring with the three aryl substituents are 18.52 (8) and 85.56 (7) and 85.57 (7)°, respectively. In the crystal, molecules are linked by O—H⋯N and C—H⋯O hydrogen bonds into chains parallel to the a axis.

Related literature

For the synthesis and properties of chiral ionic liquids, see: Olivier-Bourbigou et al. (2010 ▶); Chen et al. (2008 ▶); Mao et al. (2010 ▶).

Experimental

Crystal data

C₃₁H₂₈N₂O
M _r = 444.55
Orthorhombic,
a = 9.3413 (7) Å
b = 13.7402 (11) Å
c = 19.6296 (14) Å
V = 2519.5 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.55 mm⁻¹
T = 291 K
0.25 × 0.20 × 0.20 mm

Data collection

Agilent Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.866, T _max = 1.000
9302 measured reflections
4441 independent reflections
4007 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.098
S = 1.03
4441 reflections
313 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ▶); 1887 Friedel pairs
Flack parameter: −0.1 (3)

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: OLEX2.

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811054766/rz2683sup1.cif

e-68-0o264-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811054766/rz2683Isup2.hkl

e-68-0o264-Isup2.hkl^{(217.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811054766/rz2683Isup3.cml

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
O1—H1⋯N1ⁱ	0.82 (3)	2.01 (3)	2.825 (2)	174 (3)
C16—H16⋯O1ⁱⁱ	0.93	2.56	3.272 (3)	133

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

Acknowledgments

The authors thank Ms Y. Zhu for technical assistance. This research was supported by the National Natural Science Foundation of P. R. China (Nos. 20902017 and 21172055).

supplementary crystallographic information

Comment

Ionic liquids (ILs) have received considerable interest in the fields of synthesis, analysis and catalysis due to their unique properties (Olivier-Bourbigou et al., 2010). Chiral ionic liquids (CILs) derived from naturally abundant precursors have also attracted much interest (Chen et al., 2008). Our group is interested in the preparation and application of imidazole derived CILs (Mao et al., 2010), and we observed that the condensation reaction between L-phenylalaninol (easily available from L-phenylalanine), dibenzoyl, 4-methylbenzaldehyde and ammonium acetate afforded the title compound, a multi-aryl substituted imidazole derivative containing an appended chiral functionality. The chiral C22 carbon atom maintains the S configuration observed in L-phenylalaninol.

The molecular structure of the title compound is shown in Figure 1. As expected, the imidazole core (N1/C7/C8/N2/C24) is essentially planar. The dihedral angles formed by the imidazole ring with the three aryl substituents are 18.52 (8) (C1–C6), 85.56 (7) (C9–C14) and 85.57 (7)° (C25–C30), respectively. In the crystal structure, molecules are linked by O—H···N and C—H···O hydrogen bonds (Table 1) into chains parallel to the a axis.

Experimental

To a solution of L-phenylalaninol (15.1 g, 0.1 mol) in MeOH (50 ml) in an ice-bath, a molar equivalent of dibenzoyl, 4-methylbenzaldehyde and ammonium acetate were added. The mixture was kept stirring in the ice-bath until all the solids were dissolved before being heated to 60°C for 5 h. The mixture was then cooled to room temperature and the solvent was removed by evaporation. The residue was washed with H₂O to obtain the crude product. Crystallization of the crude product in EtOH afforded colourless crystals of the title compound.