F. K. Verkhov, I. Y. Bagryanskaya, V. I. Krasnov, I. K. Shundrina, G. A. Selivanova
{"title":"卤代 N-甲基喹啉-2-酮的晶体结构:晶体中分子间相互作用的制备与研究","authors":"F. K. Verkhov, I. Y. Bagryanskaya, V. I. Krasnov, I. K. Shundrina, G. A. Selivanova","doi":"10.1134/s0022476624030089","DOIUrl":null,"url":null,"abstract":"<h3 data-test=\"abstract-sub-heading\">Abstract</h3><p>A series of novel N-methylquinoline-2-ones with a fluorinated benzene ring (with and without Br atoms) is prepared by the interaction of halogenated quinoline-2-ones with CH<sub>3</sub>I in methanol in the presence of KOH. The molecular and crystal structures of these compounds are determined by XRD. It is shown that the main structure-forming interaction in the crystals of these compounds is π-staking, while the main supramolecular motif is formed by the π-stacks of molecules resulting from the expected π–π-interaction between the electron-deficient haloarene species and a more electron-donating pyridinone ring (fluoroarene–fluoroarene interactions are also present). In all cases, the intra-stack molecular packing changes noticeably upon the transition from fluorinated N-methylfluoroquinoline-2-ones to their bromine-containing derivatives: the lateral shift increases, the Br…π interactions appear. The Br atoms form Br…F or Br…Br intermolecular interactions.</p>","PeriodicalId":668,"journal":{"name":"Journal of Structural Chemistry","volume":null,"pages":null},"PeriodicalIF":1.2000,"publicationDate":"2024-04-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Crystal Structure of Halogenated N-Methylquinoline-2-Ones: Preparation and Study of Intermolecular Interactions in Crystals\",\"authors\":\"F. K. Verkhov, I. Y. Bagryanskaya, V. I. Krasnov, I. K. Shundrina, G. A. Selivanova\",\"doi\":\"10.1134/s0022476624030089\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<h3 data-test=\\\"abstract-sub-heading\\\">Abstract</h3><p>A series of novel N-methylquinoline-2-ones with a fluorinated benzene ring (with and without Br atoms) is prepared by the interaction of halogenated quinoline-2-ones with CH<sub>3</sub>I in methanol in the presence of KOH. The molecular and crystal structures of these compounds are determined by XRD. It is shown that the main structure-forming interaction in the crystals of these compounds is π-staking, while the main supramolecular motif is formed by the π-stacks of molecules resulting from the expected π–π-interaction between the electron-deficient haloarene species and a more electron-donating pyridinone ring (fluoroarene–fluoroarene interactions are also present). In all cases, the intra-stack molecular packing changes noticeably upon the transition from fluorinated N-methylfluoroquinoline-2-ones to their bromine-containing derivatives: the lateral shift increases, the Br…π interactions appear. The Br atoms form Br…F or Br…Br intermolecular interactions.</p>\",\"PeriodicalId\":668,\"journal\":{\"name\":\"Journal of Structural Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":1.2000,\"publicationDate\":\"2024-04-30\",\"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://doi.org/10.1134/s0022476624030089\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"CHEMISTRY, INORGANIC & NUCLEAR\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Structural Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1134/s0022476624030089","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, INORGANIC & NUCLEAR","Score":null,"Total":0}
Crystal Structure of Halogenated N-Methylquinoline-2-Ones: Preparation and Study of Intermolecular Interactions in Crystals
Abstract
A series of novel N-methylquinoline-2-ones with a fluorinated benzene ring (with and without Br atoms) is prepared by the interaction of halogenated quinoline-2-ones with CH3I in methanol in the presence of KOH. The molecular and crystal structures of these compounds are determined by XRD. It is shown that the main structure-forming interaction in the crystals of these compounds is π-staking, while the main supramolecular motif is formed by the π-stacks of molecules resulting from the expected π–π-interaction between the electron-deficient haloarene species and a more electron-donating pyridinone ring (fluoroarene–fluoroarene interactions are also present). In all cases, the intra-stack molecular packing changes noticeably upon the transition from fluorinated N-methylfluoroquinoline-2-ones to their bromine-containing derivatives: the lateral shift increases, the Br…π interactions appear. The Br atoms form Br…F or Br…Br intermolecular interactions.
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.