

Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide
Fares Hezam Al-Ostoot (1)








(1) Department of Biochemistry, Faculty of Education and Science, Albaydaa University, Al bayda, 00967, Yemen
(2) X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu, 180006, India
(3) X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu, 180006, India
(4) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru, 570005, India
(5) Department of Biochemistry, Faculty of Applied Science, University of Hajjah, Hajjah, 00967, Yemen
(6) Department of Studies in Physics, Manasagangotri, University of Mysore, Mysuru, 570005, India
(7) Department of Chemistry, Yuvaraja’s College, University of Mysore, Mysuru, 570005, India
(8) X-ray Crystallography Laboratory, Department of Physics, University of Jammu, Jammu, 180006, India
(*) Corresponding Author
Received: 15 Apr 2019 | Revised: 23 May 2019 | Accepted: 28 May 2019 | Published: 30 Sep 2019 | Issue Date: September 2019
Abstract
Medicinal chemistry of indole analogs constitutes important therapeutic agents with anti-oxidant, anti-HIV and anti-cancer activities. Indole nucleus is frequently found in synthetic and natural products, pharmaceuticals, functional materials, agrochemicals, etc. The title compound, N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide (5), has been synthesized in good yield by stirring the compound N-(2-aminophenyl)-2-(4-chlorophenoxy)acetamide (3) with 1H-indole-2-carboxylic acid (4), in dry dichloromethane followed by the addition of 2,6-lutidine, and o-(benzotriazol-1-yl)-N,N,N',N'-tetramethyl uraniumtetrafluoroborate in cooled condition. Compound 5 was synthesized and characterized by the conventional spectroscopic techniques (1H NMR, 13C NMR and LC-MS) and the three-dimensional structure was elucidated by using single crystal X-ray diffraction methods. It crystallizes in the monoclinic crystal system with space group P21/c. The structure was solved by direct methods and refined by full matrix least square procedure to a final R value of 0.043 for 2490 observed reflections. Three intra-molecular interactions of the type N-H···N and C-H···N were observed. The packing of molecules in the unit cell is governed by N-H···O and C-H···O intermolecular H-boned interactions which leads to the formation of infinite staking chain along [001] direction. In addition, two weak C-H···π interactions also contribute to molecular packing.
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DOI: 10.5155/eurjchem.10.3.234-238.1874
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Funding information
Department of Science and Technology (Project No, EMR/2014/000467), India.
Citations
[1]. Akhileshwari Prabhuswamy, Yasser Hussein Eissa Mohammed, Fares Hezam Al-Ostoot, Geetha Doddanahalli Venkatesh, Sridhar Mandayam Anandalwar, Shaukath Ara Khanum, Lokanath Neratur Krishnappagowda
Synthesis, crystal structure elucidation, Hirshfeld surface analysis, 3D energy frameworks and DFT studies of 2-(4-fluorophenoxy) acetic acid
European Journal of Chemistry 12(3), 304, 2021
DOI: 10.5155/eurjchem.12.3.304-313.2099

[2]. Pallavi H M, Fares Hezam Al-Ostoot, Hamse Kameshwar Vivek, Shaukath Ara Khanum
Design, docking, synthesis, and characterization of novel N'(2-phenoxyacetyl) nicotinohydrazide and N'(2-phenoxyacetyl)isonicotinohydrazide derivatives as anti-inflammatory and analgesic agents
Journal of Molecular Structure 1247, 131404, 2022
DOI: 10.1016/j.molstruc.2021.131404

[3]. Hamdi Hamid Sallam, Yasser Hussien Issa Mohammed, Fares Hezam Al-Ostoot, P. Akhileshwari, M.A. Sridhar, Shaukath Ara Khanum
Experimental and computational studies on the synthesis and structural characterization of 2-(4-chlorophenoxy)-N-[4-(4-methylphenyl)-1,3-thiazol-2-yl]acetamide
Journal of Molecular Structure 1249, 131588, 2022
DOI: 10.1016/j.molstruc.2021.131588

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DOI Link: https://doi.org/10.5155/eurjchem.10.3.234-238.1874


















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