Influence of Halogen Substituent on the Self-Assembly and Crystal Packing of Multicomponent Crystals Formed from Ethacridine and Meta-Halobenzoic Acids
by
Artur Mirocki * and Artur Sikorski *
Artur Mirocki * and Artur Sikorski *
University of Gdańsk, Faculty of Chemistry, W. Stwosza 63, 80-308 Gdańsk, Poland
*
Authors to whom correspondence should be addressed.
Crystals 2020, 10(2), 79; https://doi.org/10.3390/cryst10020079
Received: 10 December 2019 / Revised: 25 January 2020 / Accepted: 27 January 2020 / Published: 31 January 2020
(This article belongs to the Special Issue Halogen Bonding in Supramolecular Self-Assembly)
In order to determine the influence of halogen substituent on the self-assembly of the 6,9-diamino-2-ethoxyacridinium cations and 3-halobenzoate anions in the crystals formed from ethacridine and halobenzoic acids, the series of ethacridinium meta-halobenzoates dihydrates: ethacridinium 3-chlorobenzoate dihydrate (1), ethacridinium 3-bromobenzoate dihydrate (2), and ethacridinium 3-iodobenzoate dihydrate (3), were synthesized and structurally characterized. Single-crystal X-ray diffraction measurements showed that the title compounds crystallized in the monoclinic P21/c space group and are isostructural. In the crystals of title compounds, the ions and water molecules interact via N–H⋯O, O–H⋯O and C–H⋯O hydrogen bonds and π–π stacking interactions to produce blocks. The relationship between the distance X⋯O between the halogen atom (X=Cl, Br, I) of meta-halobenzoate anion and the O-atom from the ethoxy group of cation from neighbouring blocks and crystal packing is observed in the crystals of the title compounds.
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Keywords:
ethacridine; halobenzoic acids; intermolecular interactions; hydrogen bonds; π–π stacking interactions; X⋯O halogen bond; crystal packing
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MDPI and ACS Style
Mirocki, A.; Sikorski, A. Influence of Halogen Substituent on the Self-Assembly and Crystal Packing of Multicomponent Crystals Formed from Ethacridine and Meta-Halobenzoic Acids. Crystals 2020, 10, 79.
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