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()-4-氨基-5-{[(1,5-二甲基-3-氧代-2-苯基-2,3-二氢-1-吡唑-4-基)亚氨基]-甲基}-1-甲基-2-苯基-2,3-二氢-1-吡唑-3-酮的结构:4-氨基安替比林在二甲基甲酰胺中的空气氧化反应

Structure of ()-4-amino-5-{[(1,5-dimethyl-3-oxo-2-phenyl-2,3-di-hydro-1-pyrazol-4-yl)imino]-meth-yl}-1-methyl-2-phenyl-2,3-di-hydro-1-pyrazol-3-one: aerial oxidation of 4-amino-anti-pyrine in di-methyl-formamide.

作者信息

Kumaravel R, Stoeckli-Evans Helen, Subashini A, Shankar M G, Kučeráková Monika, Dušek Michal, Crochet Aurélien, Ramamurthi K

机构信息

Department of Physics, Annapoorana Engineering College (Autonomous), Salem - 636308, Tamilnadu, India.

Institute of Physics, University of Neuchâtel, Rue Emile-Argand 11, CH-2000 Neuchâtel, Switzerland.

出版信息

Acta Crystallogr E Crystallogr Commun. 2025 Apr 29;81(Pt 5):438-443. doi: 10.1107/S2056989025003676. eCollection 2025 May 1.

Abstract

The title compound, CHNO (), is the result of the aerial oxidation of the 5-methyl group of 4-amino-anti-pyrine to an aldehyde group followed by Schiff base formation with a second mol-ecule of 4-amino-anti-pyrine. The reaction only takes place in the presence of di-methyl-formamide. The central unit of the mol-ecule is close to planar, the pyrazole rings being inclined to each other by 3.74 (15)°. There is an intra-molecular N-H⋯N hydrogen bond enclosing an (6) ring motif and there are two further (6) rings involving weak C-H⋯O=C hydrogen bonds. The mol-ecule has an configuration about the azomethine (-N=CH-) bond. In the crystal, inversion-related mol-ecules are linked by pairs of N-H⋯O hydrogen bonds, forming dimers enclosing (10) loops. The dimers are linked by C-H⋯O hydrogen bonds and C-H⋯π inter-actions, leading to the formation of a three-dimensional supra-molecular network.

摘要

标题化合物CHNO()是4-氨基安替比林的5-甲基在空气中氧化为醛基,然后与第二个4-氨基安替比林分子形成席夫碱的产物。该反应仅在二甲基甲酰胺存在下发生。分子的中心单元接近平面,吡唑环彼此倾斜3.74(15)°。存在一个包含(6)环 motif 的分子内N-H⋯N氢键,还有另外两个涉及弱C-H⋯O=C氢键的(6)环。分子围绕偶氮甲碱(-N=CH-)键具有构型。在晶体中,通过N-H⋯O氢键对连接的反演相关分子形成包含(10)环的二聚体。二聚体通过C-H⋯O氢键和C-H⋯π相互作用连接,导致形成三维超分子网络。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/8966/12054767/012e9eec9613/e-81-00438-fig1.jpg

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