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

Yizhen Li; Pu Mao; Yongmei Xiao; Liangru Yang; Lingbo Qu

doi:10.1107/S1600536814008770

. 2014 Apr 30;70(Pt 5):o621. doi: 10.1107/S1600536814008770

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

Yizhen Li ^a, Pu Mao ^a, Yongmei Xiao ^a, Liangru Yang ^a, Lingbo Qu ^a,^*

PMCID: PMC4011293 PMID: 24860411

Abstract

In the title compound, C₃₀H₂₅N₃O₃, the central imidazole ring forms dihedral angles of 77.34 (6), 12.56 (6) and 87.04 (6)°, respectively, with the o-nitrobenzene ring and the phenyl substituents in the 5- and 4-positions. The molecular conformation is stabilized by weak intramolecular C—H⋯π interactions. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming chains running parallel to the b-axis direction.

Related literature

For the synthesis of imidazole derivatives, see: Ding et al. (2005 ▶); Heightman & Vasella (1999 ▶); Wasserscheid & Keim (2000 ▶). For related compounds synthesized by our group, see: Gao, Yang et al. (2013 ▶); Gao, Wang et al. (2013 ▶); Mao et al. (2010 ▶); Yang et al. (2012 ▶); Xiao et al. (2012 ▶).

Experimental

Crystal data

C₃₀H₂₅N₃O₃
M _r = 475.53
Orthorhombic,
a = 10.54812 (16) Å
b = 12.77836 (19) Å
c = 18.4800 (3) Å
V = 2490.87 (6) Å³
Z = 4
Cu Kα radiation
μ = 0.67 mm⁻¹
T = 291 K
0.25 × 0.22 × 0.20 mm

Data collection

Agilent Xcalibur (Eos, Gemini) diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.638, T _max = 1.000
23649 measured reflections
4460 independent reflections
4263 reflections with I > 2σ(I)
R _int = 0.054

Refinement

R[F ² > 2σ(F ²)] = 0.038
wR(F ²) = 0.111
S = 1.05
4460 reflections
330 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ▶); 1925 Friedel pairs
Absolute structure parameter: 0.2 (2)

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/S1600536814008770/rz5116sup1.cif

e-70-0o621-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008770/rz5116Isup2.hkl

e-70-0o621-Isup2.hkl^{(218.5KB, hkl)}

Click here for additional data file.^{(9.2KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814008770/rz5116Isup3.cml

CCDC reference: 997919

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 and Cg2 are the centroids of the C9–C14 and C22–C27 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯Cg1	0.93	2.84	3.715 (2)	157
C21—H21⋯Cg2	0.93	2.81	3.501 (2)	132
O3—H3⋯N1ⁱ	0.90 (3)	1.89 (3)	2.7935 (17)	179 (3)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Ms Y. Zhu for technical assistance. This research was supported by the National Natural Science Foundation of China (No. 21172055) and the Program for Innovative Research Team from Zhengzhou (131PCXTD605).

supplementary crystallographic information

1. Comment

Imidazole and its derivatives attracted research interest due to their important roles in the field of biology, medicine and chemistry. Imidazoles containing chiral N-substituent have high potentiality for application in coordination chemistry and transition metal catalysis (Ding et al., 2005; Heightman & Vasella, 1999; Wasserscheid & Keim, 2000). Our group is interested in the synthesis and application of chiral imidazolium compounds derived from natural amino acids (Gao, Yang et al., 2013; Gao, Wang et al., 2013; Mao et al., 2010; Yang et al., 2012; Xiao et al., 2012). Here we present the synthesis of a chiral nirtrophenyl-substituted imidazole derivative obtained from the condensation of a chiral aminoalcohol, nitrobenzaldehyde, ammonium acetate and benzyl. The synthetic procedure provides valuable information for the research and development of novel chiral catalysts.

The molecular structure of the title compound is shown in Figure 1. As expected, the imidazole core (C7/C8/N2/C15/N1) is essentially planar (r.m.s. deviation = 0.0056 Å). The dihedral angles it forms with the o-nitrobenzene ring and the two phenyl substituents (C1—C6, C9—C14) are 77.34 (6), 12.56 (6) and 87.04 (6)°, respectively. Two intramolecular C—H···π interactions stabilizing the molecular conformation are observed (Table 1). In the crystal, molecules are linked by O—H···N hydrogen bonds (Table 1), forming chains running parallel to the b axis.

2. Experimental

L-Phenylalaninol (15.1 g, 0.1 mol) was added to the solvent (CH₃OH, 200 mL) with ammonium acetate (7.7 g, 0.1 mol) and dibenzoyl (21.0 g, 0.1 mol) in a three-neck flask. The system was stirred until L-phenylalaninol was dissolved completely, affording a transparent dark yellow solution. The flask was then put into an ice bath and o-nitrobenzaldehyde (15.1 g, 0.1 mol) in MeOH (20 ml) was added dropwise to the solution. The mixture was heated to 65°C for 12 h. The solvent was eliminated by vacuum rotary evaporation and the crude product obtained purified using column chromatography (ethyl acetate/ethanol/triethylamine, 10:1:0.1 v/v/v). Crystallization of the product by slow evaporation of a methanol/diethyl ether solution (1:1 v/v) afforded crystals of the title compound suitable for X-ray analysis.