Crystal structure of N-(1,3-benzothiazol-2-yl)-4-iodobenzene-1-sulfonohydrazide : the importance of unusual N-H···π and I···π interactions on the supramolecular arrangement
Abstract
The 2-hydrazinyl-1,3-benzothiazole derivatives are precursors for synthesis of several compounds of technological interest, including the Bt-NH-N=CHR1(R1= alkyl, aryl, heteroaryl), derivatives. Usually when Bt-NH-NH2 is allowed to react with a benzenesulfonyl chloride the substitution is observed in the terminal nitrogen of the arenehydrazine unit, but when 4-iodophenyl sulfonyl chloride (4-IC6H4SO2Cl) was used,the product isolated was the title compound as confirmed by Rx-analysis. The determination of the crystal structure revealed that the definition of the arrangement was driven by N-H···π,C-I···Π and S2—O21···π interactions instead of the classic O···H—N hydrogen bonds. The interactions were confirmed by HS analysis. Interaction energycalculations showedthat the π interactions-based motifs play an important role in the supramolecular arrangement ,contributing about 60% to the total energy of the lattice. DFT calculations showed thatthe energy of the C-I···π dimer is complemented with contributions of π···πstacking and N-H···π interaction between the primary amine and the thiazole aromatic ring.
Citation
da Silva Rebelo Gomes , L M , Früchtl , H , Low , J N , van Mourik , T , Pinheiro , A C , de Souza , M V N & Wardell , J L 2022 , ' Crystal structure of N-(1,3-benzothiazol-2-yl)-4-iodobenzene-1-sulfonohydrazide : the importance of unusual N-H···π and I···π interactions on the supramolecular arrangement ' , Zeitschrift für Anorganische und Allgemeine Chemie , vol. 648 , no. 17 , e202200087 . https://doi.org/10.1002/zaac.202200087
Publication
Zeitschrift für Anorganische und Allgemeine Chemie
Status
Peer reviewed
ISSN
0044-2313Type
Journal article
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