2-[4,5-Diphenyl-2-(pyridin-2-yl)-1H-imidazol-1-yl]-3-phenyl­propan-1-ol

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

doi:10.1107/S1600536812018703

. 2012 May 12;68(Pt 6):o1670. doi: 10.1107/S1600536812018703

2-[4,5-Diphenyl-2-(pyridin-2-yl)-1H-imidazol-1-yl]-3-phenylpropan-1-ol

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

PMCID: PMC3379267 PMID: 22719465

Abstract

In the title compound, C₂₉H₂₅N₃O, the central imidazole ring forms dihedral angles of 64.7 (3), 33.5 (3) and 81.2 (2)° with the pyridyl and two phenyl substituents, respectively. An intramolecular C—H⋯N hydrogen bond is observed. In the crystal, O—H⋯N and C—H⋯O hydrogen bonds link the molecules into chains parallel to the a axis.

Related literature

For the synthesis and properties of chiral ionic liquids, see: Ding & Armstrong (2005 ▶); Bwambok et al. (2008 ▶); Mao et al. (2010 ▶). For a related structure, see: Xiao et al. (2012 ▶).

Experimental

Crystal data

C₂₉H₂₅N₃O
M _r = 431.52
Orthorhombic,
a = 9.2695 (4) Å
b = 15.8818 (6) Å
c = 16.0498 (6) Å
V = 2362.79 (16) Å³
Z = 4
Cu Kα radiation
μ = 0.58 mm⁻¹
T = 291 K
0.38 × 0.28 × 0.25 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.809, T _max = 0.868
9413 measured reflections
4442 independent reflections
3981 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.102
S = 1.04
4442 reflections
311 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 ▶), 1871 Friedel pairs
Flack parameter: 0.2 (4)

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/S1600536812018703/rz2739sup1.cif

e-68-o1670-sup1.cif^{(23.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018703/rz2739Isup2.hkl

e-68-o1670-Isup2.hkl^{(217.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812018703/rz2739Isup3.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
C27—H27A⋯N3	0.97	2.42	3.277 (2)	146
C22—H22⋯O1ⁱ	0.93	2.54	3.350 (3)	146
O1—H1⋯N1ⁱⁱ	0.85 (3)	1.94 (3)	2.789 (2)	174 (3)

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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 the People’s Republic of China (Nos. 20902017 and 21172055).

supplementary crystallographic information

Comment

Our group is interested in the synthesis of chiral imidazole derivatives from natural precursors through a convenient four component–one pot synthetic protocol using an aldehyde, glyoxal, ammonia, and an amine (Mao et al., 2010). During our studies we observed that by carefully choosing the four components, a number of different imidazole derivatives could be obtained easily (Xiao et al., 2012). The condensation of L-phenylalaninol, dibenzoyl, 2-formyl pyridine and ammonium acetate afforded the title compound. This compound may serve as a starting material for the research of imidazolium based chiral ionic liquids in catalysis, chiral recognization and separation (Ding & Armstrong, 2005; Bwambok et al., 2008).

The molecular structure of the title compound is shown in Figure 1. As expected, the imidazole core (N1, C7, C8, N2, C15) is essentially planar, featuring an average deviation smaller than 0.6 (2) Å. The dihedral angle between the pyridyl and imidazole rings is 64.7 (3) °, and the dihedral angles between the two phenyl substituents and the imidazole ring are 33.5 (3)° and 81.2 (2)°, respectively. The chiral C28 atom maintains the S configuration of the L-phenylalaninol. The molecular conformation is enforced by an intramolecular C—H···N hydrogen bond (Table 1). In the crystal structure, molecules are linked by intermolecular O–H···N and C—H···O hydrogen bonds 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, molar equivalents of dibenzoyl, 2-formyl pyridine 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 r.t. 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.