A1 Journal article (refereed)
Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-b]indole and Its Precursor (2023)

Boraei, A. T. A., Eltamany, E. H., Haukka, M., Soliman, S. M., Barakat, A., & Sopaih, M. (2023). Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-b]indole and Its Precursor. Crystals, 13(7), Article 1036. https://doi.org/10.3390/cryst13071036

JYU authors or editors

Publication details

All authors or editors: Boraei, Ahmed T. A.; Eltamany, Elsayed H.; Haukka, Matti; Soliman, Saied M.; Barakat, Assem; Sopaih, Manar

Journal or series: Crystals

eISSN: 2073-4352

Publication year: 2023

Publication date: 29/06/2023

Volume: 13

Issue number: 7

Article number: 1036

Publisher: MDPI AG

Publication country: Switzerland

Publication language: English

DOI: https://doi.org/10.3390/cryst13071036

Publication open access: Openly available

Publication channel open access: Open Access channel

Publication is parallel published (JYX): https://jyx.jyu.fi/handle/123456789/88220

Abstract

The hit compound 1,2,4-triazolo[4’,3’:2,3]pyridazino[4,5-b]indole 3 was synthesized from the reflux of 4-amino-5-indolyl-1,2,4-triazole-3-thione 1 with 4′-bromoacetophenone 2 in methanol catalyzed by concentrated HCl and the desired final molecule was obtained by recrystallization from methanol. The suggested structures of compounds 1 and 3 based on the spectral characterizations were confirmed by X-ray single crystal diffraction analysis. Compound 3 crystallized in the triclinic crystal system and P-1 space group with a = 5.9308(2) Å, b = 10.9695(3) Å, c = 14.7966(4) Å, α = 100.5010(10)°, β = 98.6180(10)°, and γ = 103.8180(10)°. On the other hand, the crystal system of 1 is monoclinic, where a = 6.23510(10) Å, b = 26.0156(4) Å, c = 12.4864(2) Å, β = 93.243(2)° and the space group is P21. The triazole and indole rings are found twisted from each other in both compounds. The twist angle is higher in 3 (12.65°) than 1 (4.94–7.22°). In the case of the former, the H…H (39.6%), H…C (22.0%), N…H (12.8%) and Br…H (13.2%) contacts are the most dominant while the C…C, C…H, Br…H, N…H and S…S contacts have the characteristics of strong interactions. In the latter, the C…H, N…H, S…H, S…S, and C…C contacts are the most important. In this case, the percentages of the H…H, C…H, N…H and S…H contacts are in the range of 34.9–37.4, 20.5–24.0, 12.2–13.6, 14.0–15.8, respectively. In both systems, the shape index and curvedness of surfaces confirmed the presence of π–π stacking interactions.

Keywords: x-ray crystallography; crystallography; crystals; surface chemistry

Free keywords: pyridazino[4,5-b]indol-4-one; indoles; pyridazines; X-ray single crystal; Hirshfeld surface analysis

Contributing organizations

Ministry reporting: Yes

Reporting Year: 2023

JUFO rating: 1