Naslov
Synthesis and structure of a halogen-bonded donepezil cocrystal

Autori
Vitasović, Toni ; Nemec, Vinko ; Cinčić, Dominik

Vrsta, podvrsta i kategorija rada
Sažeci sa skupova, sažetak, znanstveni

Izvornik
The Twenty-fourth Croatian-Slovenian Crystallographic Meeting - Book of Abstracts / Bijelić, Mirjana ; Cetina, Mario ; Čobić, Andrea ; Matković-Čalogović, Dubravka ; Popović, Stanko ; Štefanić, Zoran ; Tonejc, Antun ; Višnjevac Aleksandar - Zagreb : Hrvatska akademija znanosti i umjetnosti (HAZU) ; Hrvatska kristalografska zajednica HAZU, 2016, 76-76

Skup
The Twenty-fourth Croatian-Slovenian Crystallographic Meeting

Mjesto i datum
Bol, Hrvatska, 22.09.2016. - 24.09.2016

Vrsta sudjelovanja
Predavanje

Vrsta recenzije
Nije recenziran

Ključne riječi
1, 4-diiodotetrafluorobenzene ; cocrystals ; donepezil ; halogen bond ; hydrogen bond

Sažetak
Donepezil (dpz) is an active pharmaceutical ingredient (API) that belongs to the acetylcholinesterase inhibitor class of medications (Christodoulou et al., 2006). From a crystal engineering standpoint, dpz is interesting due to the presence of several functional groups which can act as hydrogen and halogen bond acceptors: the oxygen atoms in two methoxy and one carbonyl group, the piperidinyl fragment nitrogen atom, as well as the two benzene ring pi-systems. Analogously to the formation of dpz salts, cocrystallization could benefit us by providing a material with significantly more manageable physical and/or chemical properties (Schultheiss & Newman, 2009). Screening experiments have been performed by liquid-assisted grinding of reactant mixtures of dpz and 1, 4-tetrafluorodiiodobenzene (tfib) in molar ratios of 1:1, 1:1.5 and 1:2. Single crystals of the product, (dpz)(tfib)2, have been obtained by evaporation of an acetone solution of dpz and tfib in a molar ratio of 1:1. In the (dpz)(tfib)2 crystal structure, dpz molecules form R24(12) dimers via bifurcated C–H∙∙∙O hydrogen bonds. These dimers are connected into chains via I∙∙∙O halogen bonds (d(I∙∙∙O) = 3.24 Å, angle(C–I∙∙∙O) = 175 °) formed between one tfib molecule and two carbonyl oxygen atoms in two dpz molecules. The chains also contain strongly bound non-bridging tfib molecules attached as second halogen bond donors to the carbonyl oxgen atoms (d(I∙∙∙O) = 2.99 Å, angle(C–I∙∙∙O) = 178 °), that also fill up the space emptied by the conformational changes in dpz. The formed chains are linked in 3D via tfib molecules that bridge two piperidinyl nitrogen atoms (d(I∙∙∙N) = 2.91 Å, angle(C–I∙∙∙N) = 175 °).

Izvorni jezik
Engleski

Znanstvena područja
Kemija

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