Different patterns of supra­molecular aggregation in three amides containing N-(benzo[d]thia­zol­yl) substituents

Abstract

Crystal structures are reported for three amides containing N-benzo[d]thia­zole substituents. In N-(benzo[d]thia­zol-6-yl)-3-bromo­benzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the mol­ecules are linked by N—H⋯O and C—H⋯N hydrogen bonds to form ribbons of R33(19) rings, which are linked into sheets by short Br⋯Br inter­actions [3.5812 (6) Å]. N-(6-Meth­oxy­benzo[d]thia­zol-2-yl)-2-nitro­benzamide, C15H11N3O4S, crystallizes with Z′ = 2 in space group Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent mol­ecules and a combination of two N—H⋯N and five C—H⋯O hydrogen bonds links the mol­ecules into a three-dimensional network. The mol­ecules of 5-cyclo­propyl-N-(6-meth­oxy­ben­zo[d]thia­zol-2-yl)­isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the meth­oxy group and in the cyclo­propyl­isoxazole unit; symmetry-related pairs of mol­ecules are linked into dimers by pairwise N—H⋯N hydrogen bonds. Comparisons are made with the structures of some related compounds.