6-Bromo-2-(4-chlorophenyl)-3-methyl-3H-imidazo[4,5-b]pyridine

Abstract

In the title compound, C 13 H 9 BrClN 3 , the imidazopyridine fused-ring system is almost planar, with r.m.s. deviation of 0.006 (19) Å , and makes a dihedral angle of 29.32 (8) with the mean plane of the 4-chlorophenyl group. In the crystal, C-HÁ Á ÁN hydrogen bonds link the molecules into chains propagating in the [100] direction. Weak intermolecular -interactions between the five-and sixmembered rings of the 3H-imidazo [4,5-b]pyridine moieties of neighbouring molecules [centroid-centroid distance = 3.8648 (12) Å ] further consolidate the packing into layers parallel to the ab plane.

4-Benzyl-6-bromo-2-(4-chlorophenyl)-4H-imidazo[4,5-b]pyridine

“…Imidazopyridine derivatives display anticancer (Lukasik et al, 2012), tuberculostatic (Bukowski & Janowiec, 1989) and antimitotic activities (Aridoss et al, 2006). This study is a continuation of our work (Bourichi et al, 2016;Ouzidan et al, 2010) on the syntheses and structures of new imidazopyridine derivatives.…”

Crystal structure, Hirshfeld surface analysis and DFT study of 6-bromo-3-(5-bromohexyl)-2-[4-(dimethylamino)phenyl]-3H-imidazo[4,5-b]pyridine

“…Of these, two had a -CH 2 CH 2 X-(X = O, NH) chain connecting a saturated nitrogen atom [corresponding to N2 in (I)] to an ortho position of the phenyl ring and so were considered less comparable to (I) than the remainder, which can be represented by the general structure (III) ( . For R = 4-ClC 6 H 4 and R" = Br there are two reports of the compound with R 0 = 1-octyl-1H-1,2,3-triazol-4-yl)methyl [XITLUK (Bourichi et al, 2019a) and XITLUK01 (Bourichi et al, 2019b)]. The dihedral angle between the plane of the 4dimethylaminophenyl group and the mean plane of the imidazopyridine unit is ca 19 in XITLUK and ca 49 in UCOXES.…”