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Cooperativity of Halogen- and Chalcogen-Bonding Interactions in the Self-Assembly of 4‑Iodoethynyl- and 4,7-Bis(iodoethynyl)benzo-2,1,3-chalcogenadiazoles: Crystal Structures, Hirshfeld Surface Analyses, and Crystal Lattice Energy Calculations
Abstrakt
Several new 4-iodoethynyl- and 4,7-bis- (iodoethynyl)benzo-2,1,3-chalcogenadiazoles were prepared, and a comprehensive analysis of the most prominent secondary bonding interactions responsible for the crystal self-assembly was performed using X-ray diffraction. The presence of both the iodoethynyl and chalcogenadiazole moieties allows an evaluation of the preference of these molecules to aggregate through either chalcogen- or halogen-bonding interactions in the solid state. The crystal structures of the compounds revealed that their solid-state arrangements are influenced by the nature of the chalcogen atom: for the crystals of the thiadiazoles studied, the C−I···N halogen bonds were preferred, whereas in the corresponding 2,1,3-selenadiazole derivatives, the self-complementary [Se···N]2 supramolecular synthons together with the C−I···N halogen-bonding interactions determined the molecular self-assembly. Furthermore, in the case of the bis(iodoethynyl) derivative the crystal structurewas additionally influenced by the C−I···π(ethynyl) halogen bond. Hirshfeld surface and 2D fingerprint plot analyses were used to demonstrate the intermolecular interactions and intercontact distributions. Also, the total lattice energies were calculated using the CRYSTAL09 and CrystalExplorer programs. They both indicated intermolecular π···π interactions as the forces of substantial contribution to the total lattice energies.
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- Wersja publikacji
- Accepted albo Published Version
- DOI:
- Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1021/acs.cgd.1c01266
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Informacje szczegółowe
- Kategoria:
- Publikacja w czasopiśmie
- Typ:
- artykuły w czasopismach
- Opublikowano w:
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CRYSTAL GROWTH & DESIGN
nr 22,
strony 1299 - 1311,
ISSN: 1528-7483 - Język:
- angielski
- Rok wydania:
- 2022
- Opis bibliograficzny:
- Alfuth J., Zadykowicz B., Wicher B., Kazimierczuk K., Połoński T., Olszewska T.: Cooperativity of Halogen- and Chalcogen-Bonding Interactions in the Self-Assembly of 4‑Iodoethynyl- and 4,7-Bis(iodoethynyl)benzo-2,1,3-chalcogenadiazoles: Crystal Structures, Hirshfeld Surface Analyses, and Crystal Lattice Energy Calculations// CRYSTAL GROWTH & DESIGN -Vol. 22,iss. 2 (2022), s.1299-1311
- DOI:
- Cyfrowy identyfikator dokumentu elektronicznego (otwiera się w nowej karcie) 10.1021/acs.cgd.1c01266
- Źródła finansowania:
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- Publikacja bezkosztowa
- Weryfikacja:
- Politechnika Gdańska
wyświetlono 211 razy