Crystal Structure of Halogenated N-Methylquinoline-2-Ones: Preparation and Study of Intermolecular Interactions in Crystals

Crystal Structure of Halogenated N-Methylquinoline-2-Ones: Preparation and Study of Intermolecular Interactions in Crystals Full article

Journal

Journal of Structural Chemistry
ISSN: 0022-4766 , E-ISSN: 1573-8779

Output data

Year: 2024, Number: 65, Pages: 517–533 Pages count : DOI: 10.1134/S0022476624030089

Tags

fluorinated N-methylquinoline-2-ones; brominated N-methylquinoline-2-ones; XRD; crystal structure; intermolecular interactions

Authors

Verkhov F.K. ^1,2 , Bagryanskaya I.Y. ¹ , Krasnov V.I. ¹ , Shundrina I.K. ¹ , Selivanova G.A. ¹

Affiliations

1	Vorozhtsov Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences
2	Novosibirsk State University

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.

Verkhov F.K. , Bagryanskaya I.Y. , Krasnov V.I. , Shundrina I.K. , Selivanova G.A.
Crystal Structure of Halogenated N-Methylquinoline-2-Ones: Preparation and Study of Intermolecular Interactions in Crystals
Journal of Structural Chemistry. 2024. N65. P.517–533. DOI: 10.1134/S0022476624030089

Верхов Ф.К. , Багрянская И.Ю. , Краснов В.И. , Шундрина И.К. , Селиванова Г.А.
КРИСТАЛЛИЧЕСКАЯ СТРУКТУРА ГАЛОГЕНИРОВАННЫХ N-МЕТИЛХИНОЛИН-2-ОНОВ: ПОЛУЧЕНИЕ И ИССЛЕДОВАНИЕ МЕЖМОЛЕКУЛЯРНЫХ ВЗАИМОДЕЙСТВИЙ В КРИСТАЛЛАХ
Журнал структурной химии (J STRUCT CHEM+). 2024. Т.65. №3. С.123874. DOI: 10.26902/jsc_id123874 РИНЦ

Submitted:	Oct 19, 2023
Accepted:	Nov 28, 2023
Published print:	Apr 30, 2024

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