Molecular and crystal structure of 1-methyl-5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]

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dc.authoridSOYLU ETER, OZGE/0000-0001-8875-3522
dc.authoridERSANLI, CEM CUNEYT/0000-0002-8113-5091
dc.contributor.authorEter, Ozge Soylu
dc.contributor.authorAtioglu, Zeliha
dc.contributor.authorAkkurt, Mehmet
dc.contributor.authorErsanli, Cem Cuneyt
dc.contributor.authorKarali, Nilgun
dc.date.accessioned2025-03-23T19:26:57Z
dc.date.available2025-03-23T19:26:57Z
dc.date.issued2021
dc.departmentSinop Üniversitesi
dc.description.abstractBackground and Aims: The main purpose of this study is to determine the molecular structure and isomers of the new 1-methyl-5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone] (5) and to prove the 3Z-conformer of the compound 5. Methods: The molecular structure of E- and Z-isomer mixture 5 was confirmed by analytical and spectral data (UV, IR, H-1 NMR, HSQC-2D and MS). The Z-conformer of compound 5 was characterized by NMR spectroscopy and X-ray single crystal diffraction analysis method (SC-XRD). Results: The compound 5 was synthesized by condensation of 1-methyl-5-trifluoromethoxy-1H-indole-2,3-dione (2) with 4-(4-methoxyphenyl)thiosemicarbazide (4). The compound 5 was obtained in two separate forms, crystal and amorphous. It was proved by NMR data and X-ray diffraction findings that the crystal form is the Z-isomer and the amorphous form is a mixture of the E- and Z-isomers. The E- and Z-isomer ratios were determined by H-1 NMR spectroscopy. The crystal structure and molecular interactions of the Z-conformer were determined by X-ray single crystal diffraction analysis. Conclusion: In the crystal, three intramolecular N-H center dot center dot center dot N, N-H center dot center dot center dot O and C-H center dot center dot center dot S hydrogen bonds provided isomer formation. Also, molecular packing was stabilized by intermolecular C-H center dot center dot center dot O hydrogen bonds, the pi-pi stacking interactions and weak CO center dot center dot center dot pi (ring) contacts.
dc.description.sponsorshipScientific and Technological Research Council of Turkey (TUBITAK) [1003-215S011]
dc.description.sponsorshipThis work was supported by The Scientific and Technological Research Council of Turkey (TUBITAK) [grant number 1003-215S011].
dc.identifier.doi10.26650/IstanbulJPharm.2020.0080
dc.identifier.endpage66
dc.identifier.issn2587-2087
dc.identifier.issue1
dc.identifier.scopusqualityN/A
dc.identifier.startpage59
dc.identifier.trdizinid456146
dc.identifier.urihttps://doi.org/10.26650/IstanbulJPharm.2020.0080
dc.identifier.urihttps://search.trdizin.gov.tr/tr/yayin/detay/456146
dc.identifier.urihttps://hdl.handle.net/11486/4795
dc.identifier.volume51
dc.identifier.wosWOS:000655270400008
dc.identifier.wosqualityN/A
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakTR-Dizin
dc.language.isoen
dc.publisherIstanbul Univ, Fac Pharmacy
dc.relation.ispartofIstanbul Journal of Pharmacy
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_WOS_20250323
dc.subjectSynthesis
dc.subjectmolecular structure
dc.subjectisomerism
dc.subjectcrystal structure
dc.subjecthydrogen bond
dc.subjectpi-pi stacking interaction
dc.titleMolecular and crystal structure of 1-methyl-5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]
dc.typeArticle

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