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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
4-(4-Acetyl-5-methyl-1
Julio Zukerman-Schpector1, Cássio da S Dias2, Ricardo S Schwab2
1Laboratório de Cristalografia, Esterodinâmica e Modelagem Molecular, Departamento de Química, Universidade Federal de São Carlos, 13565-905 São Carlos, SP, Brazil.
Abstract:
The title compound, C12H10N4O, comprises a central 1,2,3-triazole ring (r.m.s. deviation = 0.0030 Å) flanked by N-bound 4-cyano-phenyl and C-bound acetyl groups, which make dihedral angles of 54.64 (5) and 6.8 (3)° with the five-membered ring, indicating a twisted mol-ecule. In the crystal, the three-dimensional architecture is sustained by carbonyl-C=O⋯π(triazo-yl), cyano-C≡N⋯π(triazo-yl) (these inter-actions are shown to be attractive based on non-covalent inter-action plots) and π-π stacking inter-actions [inter-centroid separation = 3.9242 (9) Å]. An analysis of the Hirshfeld surface shows the important contributions made by H⋯H (35.9%) and N⋯H (26.2%) contacts to the overall surface, as well as notable contributions by O⋯H (9.9%), C⋯H (8.7%), C⋯C (7.3%) and C⋯N (7.2%) contacts.
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