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Structural study of N-(1,3-Benzothiazol-2-yl)-4-Halobenzenesulfonylhydrazides: hirshfeld surface analysis and PIXEL calculations

2024Journal article Open access
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dc.contributor.authorGomes, Lígia Rebelo
dc.contributor.authorLow, John N.
dc.contributor.authorPinheiro, Alessandra C.
dc.contributor.authorWardell, James L.
dc.date.accessioned2024-04-04T12:07:17Z
dc.date.available2024-04-04T12:07:17Z
dc.date.issued2024
dc.description.abstractHydrazonylsulfones such as Bt-NHNHSO2R and their iminotautomers have been studied as optical materials and for their biological potential. In this work, a structural study has been carried out on N-(1,3-benzothiazol-2-yl)-4-(halogenobenzenesulfonyl)-hydrazides (1: X = F, Cl, Br). For (1: X = F), single-crystal X-ray diffraction, Hirshfeld surface analysis, and PIXEL calculations were conducted, while in (1: X = Cl) and (1: X = Br), only single-crystal X-ray diffraction studies were successfully conducted due to the disordering of the solvent. Each compound crystallises with two independent but similar amino tautomers in the asymmetric units: compound (1: X = F) crystallises in the monoclinic P21/c, and the isostructural pair (X: 1 = Cl and Br) crystallises in the tetragonal P-421c space group. In the most stable motif of the supramolecular arrangement, the molecules of the asymmetric unit are connected by classical N–H(hydrazinyl)•••N(thiazoyl) hydrogen bonds and several face-to-face, offset π•••π interactions. This motif has a very powerful influence on the crystal structure due to its direct links with the other weaker motifs. Other significant intermolecular interactions found in the structure include N–H(hydrazonyl)•••O(sulfonate) bonds. Analogous intermolecular interactions were found in similar compounds, leading to the conclusion that those interactions are the most important instabilizing the solid state of hydrazonylsulfones.pt_PT
dc.description.versioninfo:eu-repo/semantics/publishedVersionpt_PT
dc.identifier.citationGomes, L.R.; Low, J.N.; Pinheiro, A.C.; Wardell, J.L. Structural study of N-(1,3-Benzothiazol-2-yl)-4- Halobenzenesulfonylhydrazides: hirshfeld surface analysis and PIXEL calculations. Crystals 2024, 14, 330. https://doi.org/10.3390/ cryst14040330pt_PT
dc.identifier.doi10.3390/cryst14040330pt_PT
dc.identifier.issn2073-4352
dc.identifier.urihttp://hdl.handle.net/10284/12876
dc.language.isoengpt_PT
dc.peerreviewedyespt_PT
dc.publisherMDPIpt_PT
dc.subjectHydrazonylsulfonespt_PT
dc.subject1,3-benzothiazolpt_PT
dc.subjectX-raypt_PT
dc.subjectPIXEL calculationspt_PT
dc.subjectLattice energiespt_PT
dc.titleStructural study of N-(1,3-Benzothiazol-2-yl)-4-Halobenzenesulfonylhydrazides: hirshfeld surface analysis and PIXEL calculationspt_PT
dc.typejournal article
dspace.entity.typePublication
oaire.citation.issue4pt_PT
oaire.citation.startPage330pt_PT
oaire.citation.titleCrystalspt_PT
oaire.citation.volume14pt_PT
person.familyNameMaria da Silva Rebelo Gomes
person.givenNameLígia
person.identifier.ciencia-idA41A-22BE-18F0
person.identifier.orcid0000-0002-3496-6052
rcaap.rightsopenAccesspt_PT
rcaap.typearticlept_PT
relation.isAuthorOfPublication66614656-b892-46ad-93f3-7586580fd733
relation.isAuthorOfPublication.latestForDiscovery66614656-b892-46ad-93f3-7586580fd733

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