The crystal structures of three disordered 2-substituted benzimidazole esters

Chayanna Harish Chinthal, Hemmige S. Yathirajan, Nagaraja Manju, Balakrishna Kalluraya, Sabine Foro, Christopher Glidewell

Research output: Contribution to journalArticlepeer-review

Abstract

The crystal structures of three benzimidazole esters containing aryl or heterocyclic substituents at position 2 are reported, and all three exhibit disorder of mol­ecular entities. In ethyl 1-methyl-2-[4-(prop-2-yn­oxy)phen­yl]-1H-benzimidazole-5-carboxyl­ate, C20H18N2O3, (I), the prop-2-yn-1-oxyphenyl unit is disordered over two sets of atomic sites having effectively equal occupancies, 0.506 (5) and 0.494 (5). The propyl substituent in ethyl 1-propyl-2-(pyren-1-yl)-1H-benzimidazole-5-carboxyl­ate, C29H24N2O2, (II), is disordered over two sets of atomic sites having occupancies 0.601 (8) and 0.399 (8), and the ester unit in ethyl 1-methyl-2-(5-chloro-3-methyl-1-phenyl-1H-pyrazol-4-yl)-1H-benzimidazole-5-carboxyl­ate, C21H19ClN4O2 (III), is disordered over two sets of atomic sites having occupancies 0.645 (7) and 0.355 (7). In each of the C—H⋯π(arene) hydrogen bonds in (I), the donor and acceptor form parts of different disorder components, so that no continuous aggregation is possible. The mol­ecules of (II) are linked by a single C—H⋯O hydrogen bond into C(10) chains, which are linked into sheets by a π–π stacking inter­action, whereas those of (III) are just linked into C(13) chains, again by a single C—H⋯O hydrogen bond. Comparisons are made with the structures of some related compounds.
Original languageEnglish
Pages (from-to)473-479
Number of pages7
JournalActa Crystallographica Section E Crystallographic Communications
Volume77
Issue numberPart 5
Early online date9 Apr 2021
DOIs
Publication statusPublished - May 2021

Keywords

  • Benzimidazoles
  • Crystal structure
  • Disorder
  • Heterocyclic compounds
  • Hydrogen bonding
  • Supra­molecular assembly

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