Platinum precursor of anticancer drug: a structure fixed by long intermolecular N–H···I and C–H···I hydrogen bonds
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The title compound 1, cis-[diiodo(1R,2R)-1,2-diaminocyclohexane-κN,κN′]platinum(II), a precursor of a novel platinum-based anticancer complex, was synthesized. High purity (>99%) was determined by HPLC–UV/VIS and its structure was characterized by LC–ESI–MS, FT-IR and X-ray single-crystal diffraction. The molecules of the title compound interact via N–H···I and C–H···I intermolecular (ultra)-long hydrogen–iodine (acceptor) bonds (distances up to 3.1 Å). The crystal structure of the title compound 1 was compared to the structure calculated on the basis of density function theory (DFT). The calculated and measured data varied by a maximum of 0.09 Å in bond lengths and the maximum deviation between the compared angles were less than 2°. Experimentally measured bond lengths in the crystal were observed to be reduced when compared to the theoretical calculation. This was caused by both steric requirements of individual structural units and the presence of hydrogen bonds in real sample, which were confirmed by FT-IR (new bands as well as the band shifts to lower wavelengths).
KeywordsCytostatics DFT Intermolecular long hydrogen bond Platinum-based anticancer complex Single crystal/structure
The authors would like to thank to Miroslava Novotná for IR interpretation and to Jana Cibulková for database search. This study was supported by the grant MSM 6046137301 of the Ministry of Education, Youths and Sports of the Czech Republic, by the research program 2B08021 of the Ministry of Education, Youth and Sports of the Czech Republic and by the grant MPO 2 A-2TP1/O49 of the Ministry of Industry and Trade of the Czech Republic. We also acknowledge the institutional research plan No. AVOZ10100521 of the Institute of Physics of the Czech Academy of Sciences.
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