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Exploring the structural landscape of 2‐(thiophen‐2‐yl)‐1,3‐benzothiazole: high‐ Z ′ packing polymorphism and cocrystallization with calix[4]tube
Author(s) -
Alvarenga Meiry E.,
Valdo Ana Karoline S. M.,
Ribeiro Leandro,
Do Nascimento Neto José Antonio,
De Araujo Debora P.,
Da Silva Cleiton Moreira,
De Fátima Ângelo,
Martins Felipe T.
Publication year - 2019
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.304
H-Index - 17
ISSN - 2053-2296
DOI - 10.1107/s2053229619005886
Subject(s) - benzothiazole , chemistry , deprotonation , crystallography , molecule , calixarene , stereochemistry , ion , organic chemistry
We report here for the first time a cocrystal of the so‐called neutral calix[4]tube, which is two tail‐to‐tail‐arranged and partially deprotonated tetrakis(carboxymethoxy)calix[4]arenes, including three sodium ions, with 2‐(thiophen‐2‐yl)‐1,3‐benzothiazole, namely trisodium bis(carboxymethoxy)bis(carboxylatomethoxy)calix[4]arene tris(carboxymethoxy)(carboxylatomethoxy)calix[4]arene–2‐(thiophen‐2‐yl)‐1,3‐benzothiazole–dimethyl sulfoxide–water (1/1/2/2), 3Na + ·C 36 H 30 O 12 2− ·C 36 H 31 O 12 − ·C 11 H 7 NS 2 ·2C 2 H 6 OS·2H 2 O, which provides a new approach into the host–guest chemistry of inclusion complexes. Three packing polymorphs of the same benzothiazole with high Z ′ (one with Z ′ = 8 and two with Z ′ = 4) were also discovered in the course of our desired cocrystallization. The inspection of these polymorphs and a previously known polymorph with Z ′ = 2 revealed that Z ′ increases as the strength of intermolecular contacts decreases. Also, these results expand the frontier of invoking calixarenes as a host for nonsolvent small molecules, besides providing knowledge on the rare formation of high‐ Z ′ packing polymorphs of simple molecules, such as the target benzothiazole.