TY - JOUR

T1 - Crystal Structure of Halogenated N-Methylquinoline-2-Ones: Preparation and Study of Intermolecular Interactions in Crystals

AU - Verkhov, F. K.

AU - Bagryanskaya, I. Y.

AU - Krasnov, V. I.

AU - Shundrina, I. K.

AU - Selivanova, G. A.

N1 - This work was funded by the Ministry of Science and Higher Education of the Russian Federation.

PY - 2024/3

Y1 - 2024/3

N2 - 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.

AB - 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.

KW - XRD

KW - brominated N-methylquinoline-2-ones

KW - crystal structure

KW - fluorinated N-methylquinoline-2-ones

KW - intermolecular interactions

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85191889739&origin=inward&txGid=d16a3e724e0b0ea452d60f0fb2422057

UR - https://www.mendeley.com/catalogue/446ac94f-4fca-3400-942c-8c111324a0a6/

U2 - 10.1134/S0022476624030089

DO - 10.1134/S0022476624030089

M3 - Article

VL - 65

SP - 517

EP - 533

JO - Journal of Structural Chemistry

JF - Journal of Structural Chemistry

SN - 0022-4766

IS - 3

ER -