Influence of halogen size on the supramolecular and energy landscape of the THF solvates of the halogen derivatives of dianthranilide

Bartosz Bieszczad; Sylwia Pawlȩdzio; Katarzyna Polak; Jerzy Antonowicz; Adam Mieczkowski; Damian Trzybiński

doi:10.1039/d0ce00525h

Influence of halogen size on the supramolecular and energy landscape of the THF solvates of the halogen derivatives of dianthranilide

Bartosz Bieszczad, Sylwia Pawlȩdzio, Katarzyna Polak, Jerzy Antonowicz, Adam Mieczkowski, Damian Trzybiński

Research output: Contribution to journal › Article › peer-review

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Abstract

The synthesis, crystallisation and detailed description of the crystal structure of the THF solvates of four halogen (F, Cl, Br and I) derivatives of dianthranilide (5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione) have been reported. The influence of the halogen size on the conformation of the halogen derivative, the overall supramolecular architecture including the existing scheme of intermolecular interactions and the selected energy issues have been discussed in detail. The solvates which are described in this paper exhibit an interesting arrangement of molecules in their crystals resembling a "honeycomb". The variety of interactions between the respective molecules, including hydrogen bonds, halogen-mediated noncovalent interactions and π-π contacts, makes them an attractive target for crystallographic studies. The results of our analysis may lead to a better understanding of the role of a halogen functional group in the rational design of specific multicomponent crystalline networks based on compounds consisting of two substituted phenyl rings separated by a fused heterocyclic moiety.

Original language	English
Pages (from-to)	5389-5399
Number of pages	11
Journal	CrystEngComm
Volume	22
Issue number	32
DOIs	https://doi.org/10.1039/d0ce00525h
State	Published - Aug 28 2020
Externally published	Yes

Funding

This study was carried out at the Biological and Chemical Research Centre, University of Warsaw, established within the project co-financed by the European Union from the European Regional Development Fund under the Operational Programme Innovative Economy, 2007–2013. This work was supported by the Polish Ministry of Science and Higher Education (MNiSW) “DIAMENTOWY GRANT V” (decision number 0072/DIA/2016/45). The equipment used (AM, BB) was sponsored in part by the Centre for Preclinical Research and Technology (CePT), a project cosponsored by the European Regional Development Fund and Innovative Economy, The National Cohesion Strategy of Poland. Theoretical calculations were performed at the Wrocław Centre for Networking and Supercomputing (grant no. 115) and using the PL-Grid infrastructure (grant gold2018). The X-ray diffraction data collection was accomplished at the Core Facility for Crystallographic and Biophysical research to support the development of medicinal products. The “Core facility for crystallographic and biophysical research to support the development of medicinal products” project is carried out within the TEAM-TECH Core Facility programme of the Foundation for Polish Science co-financed by the European Union under the European Regional Development Fund. We thank Jacek Olędzki for recording the ESI-MS spectra, Prof. Krzysztof Woźniak for providing the access to the crystallographic laboratory and Prof. Alexander A. Korlyukov for fruitful discussions.

Funders	Funder number
Centre for Preclinical Research and Technology
National Cohesion Strategy of Poland	115, gold2018
European Commission
Fundacja na rzecz Nauki Polskiej
Ministerstwo Nauki i Szkolnictwa Wyższego	0072/DIA/2016/45
European Regional Development Fund

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title = "Influence of halogen size on the supramolecular and energy landscape of the THF solvates of the halogen derivatives of dianthranilide",

abstract = "The synthesis, crystallisation and detailed description of the crystal structure of the THF solvates of four halogen (F, Cl, Br and I) derivatives of dianthranilide (5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione) have been reported. The influence of the halogen size on the conformation of the halogen derivative, the overall supramolecular architecture including the existing scheme of intermolecular interactions and the selected energy issues have been discussed in detail. The solvates which are described in this paper exhibit an interesting arrangement of molecules in their crystals resembling a {"}honeycomb{"}. The variety of interactions between the respective molecules, including hydrogen bonds, halogen-mediated noncovalent interactions and π-π contacts, makes them an attractive target for crystallographic studies. The results of our analysis may lead to a better understanding of the role of a halogen functional group in the rational design of specific multicomponent crystalline networks based on compounds consisting of two substituted phenyl rings separated by a fused heterocyclic moiety.",

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AU - Bieszczad, Bartosz

AU - Pawlȩdzio, Sylwia

AU - Polak, Katarzyna

AU - Antonowicz, Jerzy

AU - Mieczkowski, Adam

AU - Trzybiński, Damian

PY - 2020/8/28

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N2 - The synthesis, crystallisation and detailed description of the crystal structure of the THF solvates of four halogen (F, Cl, Br and I) derivatives of dianthranilide (5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione) have been reported. The influence of the halogen size on the conformation of the halogen derivative, the overall supramolecular architecture including the existing scheme of intermolecular interactions and the selected energy issues have been discussed in detail. The solvates which are described in this paper exhibit an interesting arrangement of molecules in their crystals resembling a "honeycomb". The variety of interactions between the respective molecules, including hydrogen bonds, halogen-mediated noncovalent interactions and π-π contacts, makes them an attractive target for crystallographic studies. The results of our analysis may lead to a better understanding of the role of a halogen functional group in the rational design of specific multicomponent crystalline networks based on compounds consisting of two substituted phenyl rings separated by a fused heterocyclic moiety.

AB - The synthesis, crystallisation and detailed description of the crystal structure of the THF solvates of four halogen (F, Cl, Br and I) derivatives of dianthranilide (5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione) have been reported. The influence of the halogen size on the conformation of the halogen derivative, the overall supramolecular architecture including the existing scheme of intermolecular interactions and the selected energy issues have been discussed in detail. The solvates which are described in this paper exhibit an interesting arrangement of molecules in their crystals resembling a "honeycomb". The variety of interactions between the respective molecules, including hydrogen bonds, halogen-mediated noncovalent interactions and π-π contacts, makes them an attractive target for crystallographic studies. The results of our analysis may lead to a better understanding of the role of a halogen functional group in the rational design of specific multicomponent crystalline networks based on compounds consisting of two substituted phenyl rings separated by a fused heterocyclic moiety.

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Influence of halogen size on the supramolecular and energy landscape of the THF solvates of the halogen derivatives of dianthranilide

Abstract

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