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

Lígia Maria da Silva Rebelo Gomes*, Herbert Früchtl*, John N. Low*, Tanja van Mourik, Alessandra C. Pinheiro, Marcus V. N. de Souza*, James L. Wardell

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

2 Citations (Scopus)
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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-NHis 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.
Original languageEnglish
Article numbere202200087
Number of pages9
JournalZeitschrift für Anorganische und Allgemeine Chemie
Volume648
Issue number17
Early online date3 Jun 2022
DOIs
Publication statusPublished - 13 Sept 2022

Keywords

  • Sulfonohydrazide
  • Benzotiazole
  • Iodobenzene
  • π- interactions
  • Intermolecular forces

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