Crystal structure of 1-[2-(4-nitrophenyl)-4,5-diphenyl-1H-imidazol-1-yl]propan-2-ol

Abstract

The title compound, C 24 H 21 N 3 O 3 , crystallizes with two unique but closely r.m.s. overlay fit = 0.215 Å ) comparable molecules (1 and 2) in the asymmetric unit of the triclinic unit cell. In molecule 1, the dihedral angles between the central imidazlole ring and the benzene-ring substituents are 42.51 (9), 45.41 (9) and 56.92 (8) , respectively.Comparable data for molecule 2 are 39.36 (10), 34.45 (11) and 60.34 (8) , respectively. The rings at the 2-positions carry p-nitro substituents that subtend dihedral angles of 12.9 (4) in molecule 1 and 11.7 (4) in molecule 2 to their respective benzene ring planes. The imidazole rings also have propan-2-ol substituents on the 1-N atoms, which adopt extended conformations for the N-C-C-C chains. In the crystal, classical O-HÁ Á ÁN hydrogen bonds combine with C-HÁ Á ÁO, C-HÁ Á ÁN and C-HÁ Á Á (ring) hydrogen bonds and stack the molecules along the a-axis direction. Chemical contextImidazole compounds form the core of the structures of some well-known components of human organisms including the amino acid histidine, vitamin-B12, a component of the DNA base structure and the purines, histamine and biotin. It is also present in the structure of many natural or synthetic drug molecules, for example cimetidine, azomycin and metronidazole (Kleeman et al., 1999). Imidazole derivatives display an extensive range of biological activities and are thus used as antibacterial (Vijesh et al., 2011;Lu, et al., 2012) Structural commentaryThe title compound, (I), crystallizes with two unique molecules, 1 and 2, in the asymmetric unit. In the numbering scheme these molecules are differentiated by leading 1 and 2 digits, respectively, Fig. 1.The unique molecules form dimers in the asymmetric unit through O212-H210Á Á ÁN13 and C253-H253Á Á ÁO13 hydrogen bonds that enclose R 2 2 (18) rings, Fig. 1. The two (12) and 74.78 (12) . respectively. The benzene rings are inclined to the imidazole ring plane at angles of 42.51 (9) and 39.36 (10) for C121-C126 and C221-C226, 45.41 (9) and 34.45 (11) for C141-C146 and C241-C246 and 56.92 (8) and 60.34 (8) for C151-C156 and C251-C256, values that further attest to the close similarities between the structures of the two unique molecules. Bond lengths and angles in the two molecules are also similar and compare well with those found in comparable molecules with isopropanol substituents at the 1-position Mohamed et al., 2017;Akkurt et al., 2015).