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

Özge Soylu Eter; Zeliha Atioğlu; Mehmet Akkurt; Cem Cüneyt Ersanlı; Nilgün Karalı

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

Abstract

Background 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, 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 π-π stacking interactions and weak CO···π (ring) contacts.

Keywords

References

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Details

Primary Language

English

Subjects

Pharmacology and Pharmaceutical Sciences, Health Care Administration

Journal Section

Research Article

Authors

Özge Soylu Eter ^* This is me
0000-0001-8875-3522
Türkiye

Zeliha Atioğlu This is me
0000-0002-1141-5151
Türkiye

Mehmet Akkurt This is me
0000-0003-2421-0929
Türkiye

Cem Cüneyt Ersanlı This is me
0000-0002-8113-5091
Türkiye

Nilgün Karalı This is me
0000-0002-6916-122X
Türkiye

Publication Date

April 30, 2021

Submission Date

August 12, 2020

Acceptance Date

December 4, 2020

Published in Issue

Year 2021 Volume: 51 Number: 1

IZ

https://izlik.org/JA74FD57BX

Cite

RIS / Bibtex

APA

Soylu Eter, Ö., Atioğlu, Z., Akkurt, M., Ersanlı, C. C., & Karalı, N. (2021). Molecular and crystal structure of 1-methyl- 5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]. İstanbul Journal of Pharmacy, 51(1), 59-66. https://izlik.org/JA74FD57BX

AMA

1.Soylu Eter Ö, Atioğlu Z, Akkurt M, Ersanlı CC, Karalı N. Molecular and crystal structure of 1-methyl- 5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]. iujp. 2021;51(1):59-66. https://izlik.org/JA74FD57BX

Chicago

Soylu Eter, Özge, Zeliha Atioğlu, Mehmet Akkurt, Cem Cüneyt Ersanlı, and Nilgün Karalı. 2021. “Molecular and Crystal Structure of 1-Methyl- 5-Trifluoromethoxy-1H-Indole-2,3-Dione 3-[4-(4-Methoxyphenyl)thiosemicarbazone]”. İstanbul Journal of Pharmacy 51 (1): 59-66. https://izlik.org/JA74FD57BX.

EndNote

Soylu Eter Ö, Atioğlu Z, Akkurt M, Ersanlı CC, Karalı N (April 1, 2021) Molecular and crystal structure of 1-methyl- 5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]. İstanbul Journal of Pharmacy 51 1 59–66.

IEEE

[1]Ö. Soylu Eter, Z. Atioğlu, M. Akkurt, C. C. Ersanlı, and N. Karalı, “Molecular and crystal structure of 1-methyl- 5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]”, iujp, vol. 51, no. 1, pp. 59–66, Apr. 2021, [Online]. Available: https://izlik.org/JA74FD57BX

ISNAD

Soylu Eter, Özge - Atioğlu, Zeliha - Akkurt, Mehmet - Ersanlı, Cem Cüneyt - Karalı, Nilgün. “Molecular and Crystal Structure of 1-Methyl- 5-Trifluoromethoxy-1H-Indole-2,3-Dione 3-[4-(4-Methoxyphenyl)thiosemicarbazone]”. İstanbul Journal of Pharmacy 51/1 (April 1, 2021): 59-66. https://izlik.org/JA74FD57BX.

JAMA

1.Soylu Eter Ö, Atioğlu Z, Akkurt M, Ersanlı CC, Karalı N. Molecular and crystal structure of 1-methyl- 5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]. iujp. 2021;51:59–66.

MLA

Soylu Eter, Özge, et al. “Molecular and Crystal Structure of 1-Methyl- 5-Trifluoromethoxy-1H-Indole-2,3-Dione 3-[4-(4-Methoxyphenyl)thiosemicarbazone]”. İstanbul Journal of Pharmacy, vol. 51, no. 1, Apr. 2021, pp. 59-66, https://izlik.org/JA74FD57BX.

Vancouver

1.Özge Soylu Eter, Zeliha Atioğlu, Mehmet Akkurt, Cem Cüneyt Ersanlı, Nilgün Karalı. Molecular and crystal structure of 1-methyl- 5-trifluoromethoxy-1H-indole-2,3-dione 3-[4-(4-methoxyphenyl)thiosemicarbazone]. iujp [Internet]. 2021 Apr. 1;51(1):59-66. Available from: https://izlik.org/JA74FD57BX