{"title":"Self-Assembled Supramolecular Frameworks and Interaction Energy Studies of Acridine and Dihydroxynaphthalene Based Cocrystals","authors":"R. Jagan","doi":"10.1134/S0022476624040085","DOIUrl":null,"url":null,"abstract":"<p>Three cocrystals of acridine with 2,7-dihydroxynaphthalene (<b>Ia</b> and <b>Ib</b>) in two different polymorphs and 1,5-dihydroxynaphthalene (<b>II</b>) have been synthesized and characterized by single crystal X-ray diffraction method. Two polymorphs of acridine, 2,7-dihydroxynaphthalene cocrystal crystallizes in same space group <span>\\(P\\bar{1}\\)</span> with different unit-cell parameters. In (<b>Ia</b>) the O–H group form a <i>syn-anti</i> conformation whereas in (<b>Ib</b>) the O–H group form an <i>anti-anti</i> conformation leads to the polymorphic structure of acridine, 2,7-dihydroxynaphthalene. This study reveals that the influence of π⋯π and C–H⋯π interactions in the formation of one-, two-, and three-dimensional supramolecular frameworks when the classical hydrogen bonds such as O–H⋯N and C–H⋯O are limited to discrete motifs. The acridine molecules form continuous π⋯π stacking in the crystal structure of <b>(Ia)</b> and discrete π⋯π stacking in the crystal structure of (<b>Ib</b>) and (<b>II</b>). The conformational flexibility of the substituted hydroxy group has an influence in the supramolecular frameworks of the three-dimensional crystal structure. The intermolecular interaction energy calculation between the molecular pairs has been carried out to study the strength of the interaction and its dependence on the geometrical parameters.</p>","PeriodicalId":668,"journal":{"name":"Journal of Structural Chemistry","volume":"65 4","pages":"709 - 724"},"PeriodicalIF":1.2000,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Structural Chemistry","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1134/S0022476624040085","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
引用次数: 0
Abstract
Three cocrystals of acridine with 2,7-dihydroxynaphthalene (Ia and Ib) in two different polymorphs and 1,5-dihydroxynaphthalene (II) have been synthesized and characterized by single crystal X-ray diffraction method. Two polymorphs of acridine, 2,7-dihydroxynaphthalene cocrystal crystallizes in same space group \(P\bar{1}\) with different unit-cell parameters. In (Ia) the O–H group form a syn-anti conformation whereas in (Ib) the O–H group form an anti-anti conformation leads to the polymorphic structure of acridine, 2,7-dihydroxynaphthalene. This study reveals that the influence of π⋯π and C–H⋯π interactions in the formation of one-, two-, and three-dimensional supramolecular frameworks when the classical hydrogen bonds such as O–H⋯N and C–H⋯O are limited to discrete motifs. The acridine molecules form continuous π⋯π stacking in the crystal structure of (Ia) and discrete π⋯π stacking in the crystal structure of (Ib) and (II). The conformational flexibility of the substituted hydroxy group has an influence in the supramolecular frameworks of the three-dimensional crystal structure. The intermolecular interaction energy calculation between the molecular pairs has been carried out to study the strength of the interaction and its dependence on the geometrical parameters.
期刊介绍:
Journal is an interdisciplinary publication covering all aspects of structural chemistry, including the theory of molecular structure and chemical bond; the use of physical methods to study the electronic and spatial structure of chemical species; structural features of liquids, solutions, surfaces, supramolecular systems, nano- and solid materials; and the crystal structure of solids.