3-{[5-(4-Bromophenyl)imidazo[2,1-b][1,3,4]thiadiazol-2-yl]methyl}-1,2-benzoxazole

Abstract

In the title compound, C18H11BrN4OS, the imidazothia­diazole and benzisoxazole rings are individually planar with maximum deviations of 0.025 (3) 0.015 (4) Å, respectively, and are inclined at an angle of 23.51 (7)° with respect to each other. The planes of the imidazothia­diazole and bromo­phenyl rings are inclined at an angle of 27.34 (3)°. In the crystal, inter­molecular C—H⋯N inter­actions result in chains of mol­ecules along the b and c axes. Moreover, C—H⋯O inter­actions result in centrosymmetric head-to-head dimers with R 2 2(24) graph-set motifs. The mol­ecular packing is further stabilized by π–π stacking inter­actions between the imidazole rings with a shortest centroid–centroid distance of 3.492 (3) Å. In addition, C—H⋯π inter­actions are observed in the crystal structure.

Crystal structures of three 6-aryl-2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazoles

“…The reported structures for analogues of the products (I)-(III) carrying heterocyclic substituents at position 5 are few, but they include 5-(morpholin-4-ylmethyl)-2-(phenoxymethyl)-6-phenylimidazo [2,1-b][1,3,4]thiadiazole (Da et al, 2012) and 2-(4-fluorobenzyl)-6-(4-methoxyphenyl)-5-(morpholin-4-ylmethyl)imidazo [2,1-b][1,3,4]thiadiazole (Banu et al, 2013). Finally, we note an isostructural pair of compounds carrying 1,2-benzoxazole substituents at position 2 (Banu, Ziaulla et al, 2011b) and its 6-(4-bromophenyl) analogue (Banu, Ziaulla et al, 2011a).…”

“…The structures of a number of analogues of the intermediates, (Banu, Ziaulla et al, 2011b) and its 6-(4-bromophenyl) analogue (Banu, Ziaulla et al, 2011a).…”