Open AccessSynthesis, Crystal Structure, Hirshfeld Surface, Energy Framework and Molecular Docking Analysis of Two Novel Carbazole Derivatives
Author(s) -
G. Dhanalakshmi,
Velu Saravanan,
Arasambattu K. Mohanakrishnan,
S. Aravindhan
Publication year - 2019
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.2019.22430
Subject(s) - chemistry , triclinic crystal system , carbazole , intramolecular force , monoclinic crystal system , intermolecular force , crystallography , hydrogen bond , crystal structure , molecule , docking (animal) , interaction energy , single crystal , stereochemistry , organic chemistry , medicine , nursing
Carbazole derivatives are important compounds from medicinal point of view because of their widespread biological significance. In the present work two compounds 7-(4-chlorophenyl)-5-methyl- 12-(phenylsulfonyl)-12H-naphtho[1,2-b]carbazole (I) and 7-ethyl-5-methyl-12-(phenylsulfonyl)-12Hnaphtho[ 1,2-b]carbazole (II) have been synthesized and characterized by XRD, Hirshfeld surface, energy framework and docking analysis. Single crystal X-ray diffraction analysis shows that the compound I crystallizes in monoclinic system with space group P21/n whereas compound II crystallizes in triclinic with space group P-1. In both compounds there are two intramolecular C-H···O hydrogen bonds, which generates two S (6) ring motifs. The crystal packing is stabilized through weak C-H···O and C-H···Cl interactions. The molecules also features C-H···π interactions. The intermolecular interactions of both compounds were analyzed using Hirshfeld surface analysis and two dimensional fingerprint plots, which was confirmed by the XRD data. Energy frameworks were used to calculate the intermolecular interaction energies and their distribution over the crystal structure. Molecular docking studies show that the compounds exhibits antitumor activity.