Abstract
The benzimidazole compounds and benzoannulated cyclic benzimidazole analogues, such as benzimidazo[1,2-a]quinolines, are a part of our wider investigation on biologically active compounds, potential antitumor drugs. Here, we present the synthesis of two compounds, [2-(1H-benzimidazol-2-yl)-3-(4-bromophenyl)-acrylonitrile, 5] and [2-bromo-benzimidazo[1,2-a]quinoline-6-carbonitrile, 7] and their crystal structures revealed by X-ray single crystal diffractometry. We also report the molecular and crystal structures of two additional compounds [2-(1H-benzimidazol-2-yl)-3-(4-cyanophenyl)-acrylonitrile, 4] and [benzimidazo[1,2-a]quinoline-2,6-dicarbonitrile, 6], whose synthesis and spectroscopic characterization have been published earlier by us too (Hranjec and Karminski-Zamola, Molecules 12:1817, 2007). The compounds 4 and 5 crystallize as monohydrates. The dihedral angles calculated between phenyl and benzimidazole ring reflect not significant deviation from molecular planarity in the crystalline state for 4 and 5, while benzoannulated cyclic benzimidazole derivatives 6 and 7 are essentially planar. The crystal structures of 4 and 5 are characterized by O–H···N and N–H···O hydrogen bonds between water molecule of crystallization and imidazole NH group as well as CN group, while in 6 and 7 only weak C–H···N intermolecular hydrogen bonds exist. Although, crystal packings are analogous in 4 and 5, the molecular conformations differ slightly. In 6 there is one C–H···N hydrogen bond that do not exist in 7.
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Acknowledgments
The Ministry of Science and Technology of the Republic of Croatia, Zagreb (grant Nos. 125-0982464-1356 and 098-1191344-2943), supported this work. G. P. wishes to thank to the principle investigator prof. D. Matković-Čalogović of the project No. 119-1193079-1084 under the framework of the scientific program “Ligands, complexes, proteins—synthesis and structure—properties relationship” for kindly yielding X-ray diffraction time for recording X-ray data for compounds 5 and 7. G.P. gratefully acknowledges Krešimir Molčanov, PhD (project No. 098-1191344-2943) for data collection of compounds 4 and 6 and for drawing of molecular overlapping.
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Hranjec, M., Pavlović, G. & Karminski-Zamola, G. Crystal structure and synthesis of benzimidazole substituted acrylonitriles and benzimidazo[1, 2-a]quinolines. Struct Chem 20, 91–99 (2009). https://doi.org/10.1007/s11224-008-9398-4
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DOI: https://doi.org/10.1007/s11224-008-9398-4