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Vol. 32 No. 3 (2020): Vol 32 Issue 3

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Submitted
Aug 10, 2020
Published
Jan 31, 2020

Synthesis, Crystal Structure and Hirshfeld Surface Analysis of 3,14-Dimethyl-2,6,13,17-tetraazatricyclo(16.4.0.07,12)docosane-2-(nitric acid)

Dohyun Moon
Beamline Department, Pohang Accelerator Laboratory, Pohang 37673, Republic of Korea
Sunghwan Jeon
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea
Keon Sang Ryoo
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea
Jong-Ha Choi
jhchoi@anu.ac.kr
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea

Corresponding Author(s) : Jong-Ha Choi

jhchoi@anu.ac.kr

Asian Journal of Chemistry, Vol. 32 No. 3 (2020): Vol 32 Issue 3 page 697-702

Abstract

The crystal structure of 3,14-dimethyl-2,6,13,17-tetraazatricyclo(16.4.0.07,12)docosane-2-(nitric acid), C20H40N4·2(NO2OH) had been determined using synchrotron radiation at 220 K. The compound crystallized in the space group P21/n of the monoclinic system with two mononuclear formula units in a cell of dimensions a = 9.1930(18), b = 10.120(2), c = 12.979(3) Å and β = 101.06(3)º. The asymmetric unit contains half a centrosymmetric macrocycle and one nitric acid molecule. There were two molecules in the unit cell. In structure of macrocycle, C-C and N-C bond lengths were in the range 1.5198(19) to 1.5367(18) Å and 1.4744(16) to 1.4986 (16) Å, respectively. The NO2OH group has one longer N-O bond of 1.3441(18) Å and two shorter N-O bond of 1.2509(19) Å and 1.2510(19) Å, and O-N-O angles of 126.31(14)º, 117.98(14)º and 115.71(14)º. The N-H···O and N-H···N hydrogen bonds interconnect macrocycle (C20H40N4) with nitric acid molecules while two O-H···O hydrogen bonds link the nitric acid molecule to neighboring nitric acid molecule each other. The molecule was stabilized by forming intermolecular N-H···O, N-H−N and O-H···O hydrogen bonds. Hirshfeld surface analysis by 3D molecular surface contours and 2D fingerprint plots have been used to analyze intermolecular interactions present in the crystal.

Keywords

Crystal structure Macrocycle Nitric acid Hydrogen bonds Synchrotron radiation Hirshfeld surface analysis
MoonD., JeonS., RyooK. S., & ChoiJ.-H. (2020). Synthesis, Crystal Structure and Hirshfeld Surface Analysis of 3,14-Dimethyl-2,6,13,17-tetraazatricyclo(16.4.0.07,12)docosane-2-(nitric acid). Asian Journal of Chemistry, 32(3), 697-702. Retrieved from https://asianpubs.org/index.php/ajchem/article/view/2508
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