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

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dc.contributor.authorEter, Özge Soylu
dc.contributor.authorAtioglu, Zeliha
dc.contributor.authorAkkurt, Mehmet
dc.contributor.authorErsanli, Cem Cüneyt
dc.contributor.authorKarali, Nilgün
dc.date.accessioned2025-03-23T18:55:14Z
dc.date.available2025-03-23T18:55:14Z
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-
dc.description.abstract4-(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, 1H 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 1H 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···N, N—H···O and C—H···S hydrogen bonds provided isomer formation. Also, molecular packing was stabilized by intermolecular C—H···O hydrogen bonds, the p-p stacking interactions and weak CO···p (ring) contacts.
dc.identifier.endpage66
dc.identifier.issn2587-2087
dc.identifier.issue1
dc.identifier.startpage59
dc.identifier.urihttps://hdl.handle.net/11486/2487
dc.identifier.volume51
dc.language.isoen
dc.publisherIstanbul Üniversitesi
dc.relation.ispartofIstanbul Journal of Pharmacy
dc.relation.publicationcategoryMakale - Ulusal Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/openAccess
dc.snmzKA_DergiPark_20250323
dc.subjectSynthesis
dc.subjectmolecular structure
dc.subjectisomerism
dc.subjectcrystal structure
dc.subjecthydrogen bond
dc.subjectp-p 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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