Open AccessSynthesis, Crystal Structure and Hirshfeld Surface Analysis of 3,14-Dimethyl-2,6,13,17-tetraazatricyclo(16.4.0.07,12)docosane-2-(nitric acid)
Author(s) -
Dohyun Moon,
Sunghwan Jeon,
Keon Sang Ryoo,
JongHa Choi
Publication year - 2020
Publication title -
asian journal of chemistry/asian journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.145
H-Index - 34
eISSN - 0975-427X
pISSN - 0970-7077
DOI - 10.14233/ajchem.2020.22506
Subject(s) - chemistry , nitric acid , hydrogen bond , monoclinic crystal system , molecule , crystal structure , crystallography , intermolecular force , crystal (programming language) , stereochemistry , bond length , inorganic chemistry , organic chemistry , computer science , programming language
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) to1.5367(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 intermolecularinteractions present in the crystal.