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The title complex, [CuCl2(C21H22N4O)], contains a bis­(benzimidazole) unit with a chiral bridgehead C atom that forms part of a tetra­hydro­pyrrole ring fused to one of the benzimidazoles. The chelate angle is 90.45 (9)° and the dihedral angle between the essentially planar benzimidazole fragments is 26.68 (9)°. The CuII coordination geometry lies approximately midway between tetra­hedral and square planar. Overall, each chiral mol­ecule contains six fused rings, and a racemic mixture is formed with symmetry-related enanti­omers. In the crystal, C—H...π and C—H...Cl inter­actions link mol­ecules into a supra­molecular chain along the a-axis direction.

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The structure of the title tri­fluoro­acetic acid adduct, C17H12N2O3·C2HF3O2, contains a tri­fluoro­acetic acid mol­ecule hydrogen bonded to the imine N atom of the imidazole ring of a nearly planar four-fused-ring system (r.m.s. deviatiation = 0.013 Å). The carb­oxy­lic acid group of the triflouro­acetic acid mol­ecule is twisted with respect to the mean plane of the four-fused-ring sytem by 75.9 (2)°. A short intra­molecular C—H...O hydrogen bond occurs. In the crystal, the adduct mol­ecules are arranged into stacks along the b axis via π–π inter­actions between imidazole rings and between imidazole and one of the benzene rings [centroid–centroid distances 3.352 (2) and 3.485 (2) Å, respectively]. Molecules are linked via C—H...O hydrogen bonds, forming an alternating polymeric head-to-head/tail-to-tail stepped chain approximately along the a-axis direction and tilted on an axis bisecting the b and c axes.
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