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 language | English |
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Pages (from-to) | 473-479 |
Number of pages | 7 |
Journal | Acta Crystallographica Section E Crystallographic Communications |
Volume | 77 |
Issue number | Part 5 |
Early online date | 9 Apr 2021 |
DOIs | |
Publication status | Published - May 2021 |
Keywords
- Benzimidazoles
- Crystal structure
- Disorder
- Heterocyclic compounds
- Hydrogen bonding
- Supramolecular assembly
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The crystal structures of three disordered 2-substituted benzimidazole esters (dataset)
Chinthal, C. H. (Creator), Yathirajan, H. S. (Creator), Manju, N. (Creator), Kalluraya, B. (Creator), Foro, S. (Creator) & Glidewell, C. (Creator), Cambridge Crystallographic Data Centre, 29 Mar 2021
DOI: 10.5517/ccdc.csd.cc27m8fl, https://dx.doi.org/10.5517/ccdc.csd.cc27m8gm and one more link, https://dx.doi.org/10.5517/ccdc.csd.cc27m8hn (show fewer)
Dataset