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Vol. 33 No. 8 (2021): Vol 33 Issue 8, 2021

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Synthesis, Spectroscopic Properties and Hirshfeld Surface Analysis of 3,14-Dimethyl-2,6,13,17-tetraazoniatricyclo(16.4.0.07,12)docosane Tetrachloride Tetrahydrate

https://doi.org/10.14233/ajchem.2021.23258
Sunghwan Jeon
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea
Jan Moncol
Department of Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovakia
Milan Mazur
Department of Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovakia
Marian Valko
Department of Chemistry, Faculty of Chemical and Food Technology, Slovak University of Technology, SK-81237 Bratislava, Slovakia
Keon Sang Ryoo
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea
Jong-Ha Choi
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea

Corresponding Author(s) : Keon Sang Ryoo

ksr@anu.ac.kr

Asian Journal of Chemistry, Vol. 33 No. 8 (2021): Vol 33 Issue 8, 2021

Abstract

Single crystals of 3,14-dimethyl-2,6,13,17-tetraazoniatricyclo(16.4.0.07,12)docosane tetrachloride tetrahydrate compound, [C20H44N4]Cl4·4H2O (1), were obtained by a novel synthetic route and characterized by elemental analysis and X-ray diffraction. The synthesized compound crystallized in the monoclinic space group P21/n with two molecules of compound 1 in the unit cell [a = 7.5548(3) Å, b = 23.1838(8) Å, c = 8.3101(4) Å; β = 103.390(3)º]. The asymmetric unit contains half a centrosymmetric macrocyclic cation, two chloride anions and two water molecules. The organic [C20H44N4]4+ fragment of 1 adopts an exodentate [3,4,3,4]-D conformation. The C–C and N–C bond lengths of the macrocyclic tetracation range 1.525(3)-1.540(3) Å and 1.505(3)-1.519(3) Å, respectively. A three-dimensional hydrogen bonding network provides crystal cohesion through O–H···Cl, N–H···Cl and N–H···O interactions between organic cations, chloride anions and water molecules. The functional groups present in the crystal were studied by Fourier-transform infrared spectroscopy and Raman spectroscopy. The Hirshfeld surface analysis and 2D fingerprint plots revealed that the crystal packing in 1 is dominated by H···H, Cl···H/H···Cl and O···H/H···O contacts.

Keywords

Characterization Macrocycle Endodentate Tetrachloride Spectral properties Hirshfeld surface analysis
Jeon, S., Moncol, J., Mazur, M., Valko, M., Sang Ryoo, K., & Choi, J.-H. (2021). Synthesis, Spectroscopic Properties and Hirshfeld Surface Analysis of 3,14-Dimethyl-2,6,13,17-tetraazoniatricyclo(16.4.0.07,12)docosane Tetrachloride Tetrahydrate. Asian Journal of Chemistry, 33(8), 1861–1867. https://doi.org/10.14233/ajchem.2021.23258
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