1,5-Dimethyl-2-phenyl-1H-pyrazol-3(2H)-one–4,4′-(propane-2,2-diyl)bis[1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] (1/1)

Abstract

The asymmetric unit of the title compound, C11H12N2O·C25H28N4O2, contains two different mol­ecules. The smaller is known as anti­pyrine [systematic name: 1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one] and the larger is built up from two antypirine mol­ecules which are connected through a C atom of the pyrazolone ring to a central propanyl part [systematic name: 4,4′-(propane-2,2-di­yl)bis­[1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one]. Intra­molecular C—H⋯O hydrogen bonds occur in the latter mol­ecule. In the crystal, C—H⋯O hydrogen bonds link the mol­ecules into a two-dimensional network parallel to (001).

Structural and Computational Insights into Cocrystal Interactions: A Case on Cocrystals of Antipyrine and Aminophenazone

“…Different studies have reported successful breakthroughs in synthesizing different cocrystals of AN and AM. According to the survey of existing crystal structures in the Cambridge Structural Database, five cocrystals of AN contain the coformers salicylic acid, sulfanilamide, and sulfaguanidine, 4-aminobenzoic acid, and 4,4′-propane-2,2′-diyldiantipyrine, − and three cocrystals of AM contain the coformers cyclobarbital, thiocarbamide, and barbital. − The association between the coformer and API is mostly achieved through an intermolecular hydrogen bond with the hydroxyl or amino group in the coformer as the proton donor and the carbanyl group of AN or AM as the acceptor. However, as a special example, no classical H bonds exist in AN and 4,4′-propane-2,2′-diyldiantipyrine cocrystal, which possibly maintain their 3D structure mainly by van der Waals interaction.…”

Design of Cocrystals for Molecules with Limited Hydrogen Bonding Functionalities: Propyphenazone as a Model System

“…The case study compound, PROPY, shows structural similarity to two other compounds, antipyrine and edaravone, which contain the same molecular skeleton (phenylpyrazole); however PROPY contains an isopropyl substituent which causes steric hindrance at the carbonyl (Figure ). A number of multicomponent systems − have been reported for antipyrine and edaravone, from which additional knowledge can be gained and can be used in the design and search for cocrystals of PROPY. An analysis of these systems indicates that most of the coformers feature CO 2 H donor groups.…”

Crystal engineering of a co-crystal of antipyrine and 2-chlorobenzoic acid: relative energetic contributions based on multipolar refinement

“…This drug, when consumed, acts on the central nervous system (CNS) leading to the non-selective inhibition of both isoforms of cyclooxygenase (COX-1, COX-2) enzymes which are involved in prostaglandin (PG) synthesis. 23,25,26 To date, several literature reviews focusing on antipyrine (API) co-crystals with suitable co-formers namely salicylic acid, 27 saccharin, fumaric acid, 28 4-aminobenzoic acid, 29 sulphanilamide, 30 4,4′-propane-2,2′-diyldiantipyrine 31 and sulfaguanidine 32,33 have been published. In addition, the literature also contains cocrystals of phenazone derivatives like propyphenazone–pyrithyldione, 34 propyphenazone–hydroquinone, 35 4-aminoantipyrine-fumaric acid, 28 4-aminoantipyrine-2-amino benzoic acid, 36 etc.…”