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Different patterns of supra­molecular aggregation in three amides containing N-(benzo[d]thia­zol­yl) substituents

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Date
05/2021
Author
Mahesha, Ninganayaka
Yathirajan, Hemmige S.
Nagma Banu, Holalagudu A.
Kalluraya, Balakrishna
Foro, Sabine
Glidewell, Christopher
Keywords
Benzo[d]thia­zoles
Crystal structure
Disorder
Halogen bonding
Heterocyclic compounds
Hydrogen bonding
Mol­ecular conformation
QD Chemistry
DAS
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Abstract
Crystal structures are reported for three amides containing N-benzo[d]thia­zole substituents. In N-(benzo[d]thia­zol-6-yl)-3-bromo­benzamide, C14H9BrN2OS, where the two ring systems are nearly parallel to one another [dihedral angle = 5.8 (2)°], the mol­ecules are linked by N—H⋯O and C—H⋯N hydrogen bonds to form ribbons of R33(19) rings, which are linked into sheets by short Br⋯Br inter­actions [3.5812 (6) Å]. N-(6-Meth­oxy­benzo[d]thia­zol-2-yl)-2-nitro­benzamide, C15H11N3O4S, crystallizes with Z′ = 2 in space group Pna21: the dihedral angles between the ring systems [46.43 (15) and 66.35 (13)°] are significantly different in the independent mol­ecules and a combination of two N—H⋯N and five C—H⋯O hydrogen bonds links the mol­ecules into a three-dimensional network. The mol­ecules of 5-cyclo­propyl-N-(6-meth­oxy­ben­zo[d]thia­zol-2-yl)­isoxazole-3-carboxamide, C15H13N3O3S, exhibit two forms of disorder, in the meth­oxy group and in the cyclo­propyl­isoxazole unit; symmetry-related pairs of mol­ecules are linked into dimers by pairwise N—H⋯N hydrogen bonds. Comparisons are made with the structures of some related compounds.
Citation
Mahesha , N , Yathirajan , H S , Nagma Banu , H A , Kalluraya , B , Foro , S & Glidewell , C 2021 , ' Different patterns of supra­molecular aggregation in three amides containing N -(benzo[ d ]thia­zol­yl) substituents ' , Acta Crystallographica Section E Crystallographic Communications , vol. 77 , no. Part 5 , pp. 504-511 . https://doi.org/10.1107/S2056989021003637
Publication
Acta Crystallographica Section E Crystallographic Communications
Status
Peer reviewed
DOI
https://doi.org/10.1107/S2056989021003637
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 is grateful to the UGC, 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/10023/23261

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