Crystal structure of ethyl 2-[2-(4-methyl-benzo-yl)-5-p-tolyl-1H-imidazol-1-yl]acetate.

E Arockia Jeya Yasmi Prabha,Qazi Naveed Ahmed,S Athimoolam,S Suresh Kumar,Anil K Padala

doi:10.1107/s2056989016002504

Abstract

In the title compound, C22H22N2O3, the plane of the five-membered ring is oriented at dihedral angles of 45.4 (1) and 52.5 (1)° to the phenyl rings. Furthermore, this ring makes an angle of 85.2 (2)° with the plane of the ethyl acetate substituent. The mol-ecular structure is affected by an intra-molecular C-H⋯O hydrogen bond between an H atom from the p-tolyl group and the carbonyl O atom of the acetate. The methyl group of the ethyl acetate residue is disordered over two sites with equal occupancies. The crystal structure features inter-molecular C-H⋯O and C-H⋯N inter-actions. One of the C-H⋯O hydrogen bonds forms a C(5) chain motif extending along the a axis. In addition, C-H⋯N contacts form inversion dimers with R 2 (2)(12) ring motifs, linking the imidazole ring system to the benzene ring of the p-tolyl substituent.

Highlights

C22H22N2O3, the plane of the five-membered ring is oriented at dihedral angles of 45.4 (1) and 52.5 (1) to the phenyl rings
We are interested in the synthesis of active pharmaceutical ingredients (APIs) based on imidazoles and we report here the synthesis and crystal structure of the title imidazole derivative
The phenyl rings and the plane of the imidazole ring are inclined at angles of 45.4 (1) and 52.5 (1)

Summary

Chemical context

Imidazole and its derivatives have numerous pharmaceutical applications including uses as antifungal (Shingalapur et al.2009), antimicrobial (Sharma et al 2009), anti-inflammatory (Puratchikody et al 2007), analgesic (Achar et al 2010), antitubercular (Pandey et al 2009), antidepressant (Hadizadeh et al 2008), antileishmanial (Bhandari et al 2009) and anticancer agents (Ozkay et al 2010). We are interested in the synthesis of active pharmaceutical ingredients (APIs) based on imidazoles and we report here the synthesis and crystal structure of the title imidazole derivative

Structural commentary

Database survey

Synthesis and crystallization

Refinement