A1 Alkuperäisartikkeli tieteellisessä aikakauslehdessä
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-tekijät tai -toimittajat

Julkaisun tiedot

Julkaisun kaikki tekijät tai toimittajat: Boraei, Ahmed T. A.; Eltamany, Elsayed H.; Haukka, Matti; Soliman, Saied M.; Barakat, Assem; Sopaih, Manar

Lehti tai sarja: Crystals

eISSN: 2073-4352

Julkaisuvuosi: 2023

Ilmestymispäivä: 29.06.2023

Volyymi: 13

Lehden numero: 7

Artikkelinumero: 1036

Kustantaja: MDPI AG

Julkaisumaa: Sveitsi

Julkaisun kieli: englanti

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

Julkaisun avoin saatavuus: Avoimesti saatavilla

Julkaisukanavan avoin saatavuus: Kokonaan avoin julkaisukanava

Julkaisu on rinnakkaistallennettu (JYX): https://jyx.jyu.fi/handle/123456789/88220

Tiivistelmä

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.

YSO-asiasanat: röntgenkristallografia; kidetiede; kiteet; pintakemia

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

Liittyvät organisaatiot

OKM-raportointi: Kyllä

Raportointivuosi: 2023

JUFO-taso: 1