Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole and Its Precursor
The hit compound 1,2,4-triazolo[4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole <b>3</b> was synthesized from the reflux of 4-amino-5-indolyl-1,2,4-triazole-3-thione <b>1</b> with 4′-bromoacetophenone <b>2</b> in methanol catalyzed by concentrated HCl and the...
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MDPI AG
2023-06-01
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| Series: | Crystals |
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| author | Ahmed T. A. Boraei Elsayed H. Eltamany Matti Haukka Saied M. Soliman Assem Barakat Manar Sopaih |
| author_facet | Ahmed T. A. Boraei Elsayed H. Eltamany Matti Haukka Saied M. Soliman Assem Barakat Manar Sopaih |
| author_sort | Ahmed T. A. Boraei |
| collection | DOAJ |
| description | The hit compound 1,2,4-triazolo[4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole <b>3</b> was synthesized from the reflux of 4-amino-5-indolyl-1,2,4-triazole-3-thione <b>1</b> with 4′-bromoacetophenone <b>2</b> in methanol catalyzed by concentrated HCl and the desired final molecule was obtained by recrystallization from methanol. The suggested structures of compounds <b>1</b> and <b>3</b> based on the spectral characterizations were confirmed by X-ray single crystal diffraction analysis. Compound <b>3</b> crystallized in the triclinic crystal system and <i>P-1</i> space group with <i>a</i> = 5.9308(2) Å, <i>b</i> = 10.9695(3) Å, <i>c</i> = 14.7966(4) Å, <i>α</i> = 100.5010(10)°, <i>β</i> = 98.6180(10)°, and <i>γ</i> = 103.8180(10)°. On the other hand, the crystal system of <b>1</b> is monoclinic, where <i>a</i> = 6.23510(10) Å, <i>b</i> = 26.0156(4) Å, <i>c</i> = 12.4864(2) Å, <i>β</i> = 93.243(2)° and the space group is <i>P2<b><sub>1</sub></b></i>. The triazole and indole rings are found twisted from each other in both compounds. The twist angle is higher in <b>3</b> (12.65°) than <b>1</b> (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. |
| first_indexed | 2024-03-11T01:10:39Z |
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| series | Crystals |
| spelling | doaj.art-5b5b6a0b4da54aa88dd3905d33b0130b2023-11-18T18:53:31ZengMDPI AGCrystals2073-43522023-06-01137103610.3390/cryst13071036Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole and Its PrecursorAhmed T. A. Boraei0Elsayed H. Eltamany1Matti Haukka2Saied M. Soliman3Assem Barakat4Manar Sopaih5Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, EgyptChemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, EgyptDepartment of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, FinlandChemistry Department, Faculty of Science, Alexandria University, P.O. Box 426, Alexandria 21321, EgyptDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaChemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, EgyptThe hit compound 1,2,4-triazolo[4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole <b>3</b> was synthesized from the reflux of 4-amino-5-indolyl-1,2,4-triazole-3-thione <b>1</b> with 4′-bromoacetophenone <b>2</b> in methanol catalyzed by concentrated HCl and the desired final molecule was obtained by recrystallization from methanol. The suggested structures of compounds <b>1</b> and <b>3</b> based on the spectral characterizations were confirmed by X-ray single crystal diffraction analysis. Compound <b>3</b> crystallized in the triclinic crystal system and <i>P-1</i> space group with <i>a</i> = 5.9308(2) Å, <i>b</i> = 10.9695(3) Å, <i>c</i> = 14.7966(4) Å, <i>α</i> = 100.5010(10)°, <i>β</i> = 98.6180(10)°, and <i>γ</i> = 103.8180(10)°. On the other hand, the crystal system of <b>1</b> is monoclinic, where <i>a</i> = 6.23510(10) Å, <i>b</i> = 26.0156(4) Å, <i>c</i> = 12.4864(2) Å, <i>β</i> = 93.243(2)° and the space group is <i>P2<b><sub>1</sub></b></i>. The triazole and indole rings are found twisted from each other in both compounds. The twist angle is higher in <b>3</b> (12.65°) than <b>1</b> (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.https://www.mdpi.com/2073-4352/13/7/1036pyridazino[4,5-<i>b</i>]indol-4-oneindolespyridazinesX-ray single crystalHirshfeld surface analysis |
| spellingShingle | Ahmed T. A. Boraei Elsayed H. Eltamany Matti Haukka Saied M. Soliman Assem Barakat Manar Sopaih Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole and Its Precursor Crystals pyridazino[4,5-<i>b</i>]indol-4-one indoles pyridazines X-ray single crystal Hirshfeld surface analysis |
| title | Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole and Its Precursor |
| title_full | Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole and Its Precursor |
| title_fullStr | Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole and Its Precursor |
| title_full_unstemmed | Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole and Its Precursor |
| title_short | Synthesis and X-ray Crystal Structure Analysis of Substituted 1,2,4-Triazolo [4’,3’:2,3]pyridazino[4,5-<i>b</i>]indole and Its Precursor |
| title_sort | synthesis and x ray crystal structure analysis of substituted 1 2 4 triazolo 4 3 2 3 pyridazino 4 5 i b i indole and its precursor |
| topic | pyridazino[4,5-<i>b</i>]indol-4-one indoles pyridazines X-ray single crystal Hirshfeld surface analysis |
| url | https://www.mdpi.com/2073-4352/13/7/1036 |
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