Structure of (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: aerial oxidation of 4-aminoantipyrine in dimethylformamide
The title compound, C22H22N6O2 (I), is the result of the aerial oxidation of the 5-methyl group of 4-aminoantipyrine to an aldehyde group followed by Schiff base formation with a second molecule of 4-aminoantipyrine. The reaction only takes place in the presence of dimethylformamide. The central uni...
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International Union of Crystallography
2025-05-01
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| Series: | Acta Crystallographica Section E: Crystallographic Communications |
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| Online Access: | https://journals.iucr.org/paper?S2056989025003676 |
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| author | R. Kumaravel Helen Stoeckli-Evans A. Subashini M. G. Shankar Monika Kučeráková Michal Dušek Aurélien Crochet K. Ramamurthi |
| author_facet | R. Kumaravel Helen Stoeckli-Evans A. Subashini M. G. Shankar Monika Kučeráková Michal Dušek Aurélien Crochet K. Ramamurthi |
| author_sort | R. Kumaravel |
| collection | DOAJ |
| description | The title compound, C22H22N6O2 (I), is the result of the aerial oxidation of the 5-methyl group of 4-aminoantipyrine to an aldehyde group followed by Schiff base formation with a second molecule of 4-aminoantipyrine. The reaction only takes place in the presence of dimethylformamide. The central unit of the molecule is close to planar, the pyrazole rings being inclined to each other by 3.74 (15)°. There is an intramolecular N—H...N hydrogen bond enclosing an S(6) ring motif and there are two further S(6) rings involving weak C—H...O=C hydrogen bonds. The molecule has an E configuration about the azomethine (—N=CH—) bond. In the crystal, inversion-related molecules are linked by pairs of N—H...O hydrogen bonds, forming dimers enclosing R22(10) loops. The dimers are linked by C—H...O hydrogen bonds and C—H...π interactions, leading to the formation of a three-dimensional supramolecular network. |
| format | Article |
| id | doaj-art-804d6e357f384dfb9b2f0b3ec6aac286 |
| institution | OA Journals |
| issn | 2056-9890 |
| language | English |
| publishDate | 2025-05-01 |
| publisher | International Union of Crystallography |
| record_format | Article |
| series | Acta Crystallographica Section E: Crystallographic Communications |
| spelling | doaj-art-804d6e357f384dfb9b2f0b3ec6aac2862025-08-20T02:14:53ZengInternational Union of CrystallographyActa Crystallographica Section E: Crystallographic Communications2056-98902025-05-0181543844310.1107/S2056989025003676hb8135Structure of (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: aerial oxidation of 4-aminoantipyrine in dimethylformamideR. Kumaravel0Helen Stoeckli-Evans1A. Subashini2M. G. Shankar3Monika Kučeráková4Michal Dušek5Aurélien Crochet6K. Ramamurthi7Department of Physics, Annapoorana Engineering College (Autonomous), Salem - 636308, Tamilnadu, IndiaInstitute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2000 Neuchâtel, SwitzerlandPG and Research Department of Physics, Srimad Andavan Arts and Science College (Autonomous), Affiliated to Bharathidasan University, Tiruchirappalli - 620005, Tamilnadu, IndiaPG and Research Department of Physics, Srimad Andavan Arts and Science College (Autonomous), Affiliated to Bharathidasan University, Tiruchirappalli - 620005, Tamilnadu, IndiaInstitute of Physics ASCR, Na Slovance 2, 182 21 Praha 8, Czech RepublicInstitute of Physics ASCR, Na Slovance 2, 182 21 Praha 8, Czech RepublicChemistry Department, University of Fribourg, Chemin du Musée 9, CH-1700 Fribourg, SwitzerlandCrystal Growth and Thin Film Laboratory, Department of Physics, Bharathidasan University, Tiruchirappalli - 620024, Tamilnadu, IndiaThe title compound, C22H22N6O2 (I), is the result of the aerial oxidation of the 5-methyl group of 4-aminoantipyrine to an aldehyde group followed by Schiff base formation with a second molecule of 4-aminoantipyrine. The reaction only takes place in the presence of dimethylformamide. The central unit of the molecule is close to planar, the pyrazole rings being inclined to each other by 3.74 (15)°. There is an intramolecular N—H...N hydrogen bond enclosing an S(6) ring motif and there are two further S(6) rings involving weak C—H...O=C hydrogen bonds. The molecule has an E configuration about the azomethine (—N=CH—) bond. In the crystal, inversion-related molecules are linked by pairs of N—H...O hydrogen bonds, forming dimers enclosing R22(10) loops. The dimers are linked by C—H...O hydrogen bonds and C—H...π interactions, leading to the formation of a three-dimensional supramolecular network.https://journals.iucr.org/paper?S2056989025003676crystal structure4-aminoantipyrineaerial oxidationdimethylformamidehydrogen bondinghirshfeld surface |
| spellingShingle | R. Kumaravel Helen Stoeckli-Evans A. Subashini M. G. Shankar Monika Kučeráková Michal Dušek Aurélien Crochet K. Ramamurthi Structure of (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: aerial oxidation of 4-aminoantipyrine in dimethylformamide Acta Crystallographica Section E: Crystallographic Communications crystal structure 4-aminoantipyrine aerial oxidation dimethylformamide hydrogen bonding hirshfeld surface |
| title | Structure of (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: aerial oxidation of 4-aminoantipyrine in dimethylformamide |
| title_full | Structure of (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: aerial oxidation of 4-aminoantipyrine in dimethylformamide |
| title_fullStr | Structure of (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: aerial oxidation of 4-aminoantipyrine in dimethylformamide |
| title_full_unstemmed | Structure of (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: aerial oxidation of 4-aminoantipyrine in dimethylformamide |
| title_short | Structure of (E)-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino]methyl}-1-methyl-2-phenyl-2,3-dihydro-1H-pyrazol-3-one: aerial oxidation of 4-aminoantipyrine in dimethylformamide |
| title_sort | structure of e 4 amino 5 1 5 dimethyl 3 oxo 2 phenyl 2 3 dihydro 1h pyrazol 4 yl imino methyl 1 methyl 2 phenyl 2 3 dihydro 1h pyrazol 3 one aerial oxidation of 4 aminoantipyrine in dimethylformamide |
| topic | crystal structure 4-aminoantipyrine aerial oxidation dimethylformamide hydrogen bonding hirshfeld surface |
| url | https://journals.iucr.org/paper?S2056989025003676 |
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