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The crystal structures of three disordered 2-substituted benzimidazole esters

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Date
05/2021
Author
Chinthal, Chayanna Harish
Yathirajan, Hemmige S.
Manju, Nagaraja
Kalluraya, Balakrishna
Foro, Sabine
Glidewell, Christopher
Keywords
Benzimidazoles
Crystal structure
Disorder
Heterocyclic compounds
Hydrogen bonding
Supra­molecular assembly
QD Chemistry
DAS
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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.
Citation
Chinthal , C H , Yathirajan , H S , Manju , N , Kalluraya , B , Foro , S & Glidewell , C 2021 , ' The crystal structures of three disordered 2-substituted benzimidazole esters ' , Acta Crystallographica Section E Crystallographic Communications , vol. 77 , no. Part 5 , pp. 473-479 . https://doi.org/10.1107/S2056989021003364
Publication
Acta Crystallographica Section E Crystallographic Communications
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2056989021003364
ISSN
2056-9890
Type
Journal article
Rights
Copyright © 2020 The Author(s). This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Description
HSY thanks the University Grants Commission, New Delhi, for the award of a BSR Faculty Fellowship for three years.
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  • University of St Andrews Research
URI
http://hdl.handle.net/10023/23262

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