European Journal of Chemistry 2019, 10(3), 234-238 | doi: https://doi.org/10.5155/eurjchem.10.3.234-238.1874 | Get rights and content

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


Fares Hezam Al-Ostoot (1) orcid , Jigmat Stondus (2) orcid , Sumati Anthal (3) orcid , Geetha Doddenahally Venkatesh (4) orcid , Yasser Hussein Eissa Mohammed (5) orcid , Mandayam Anandalwar Sridhar (6) orcid , Shaukath Ara Khanum (7) orcid , Rajni Kant (8,*) orcid

(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.


Keywords


Amide; Single crystal; X-ray diffraction; Indole analogues; H-bonded interactions; Spectroscopic analysis

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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

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[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
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[2]. Pallavi H M, Fares Hezam Al-Ostoot, Hamse Kameshwar Vivek, Shaukath Ara Khanum
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[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
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How to cite


Al-Ostoot, F.; Stondus, J.; Anthal, S.; Venkatesh, G.; Mohammed, Y.; Sridhar, M.; Khanum, S.; Kant, R. Eur. J. Chem. 2019, 10(3), 234-238. doi:10.5155/eurjchem.10.3.234-238.1874
Al-Ostoot, F.; Stondus, J.; Anthal, S.; Venkatesh, G.; Mohammed, Y.; Sridhar, M.; Khanum, S.; Kant, R. Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide. Eur. J. Chem. 2019, 10(3), 234-238. doi:10.5155/eurjchem.10.3.234-238.1874
Al-Ostoot, F., Stondus, J., Anthal, S., Venkatesh, G., Mohammed, Y., Sridhar, M., Khanum, S., & Kant, R. (2019). Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide. European Journal of Chemistry, 10(3), 234-238. doi:10.5155/eurjchem.10.3.234-238.1874
Al-Ostoot, Fares, Jigmat Stondus, Sumati Anthal, Geetha Doddenahally Venkatesh, Yasser Hussein Eissa Mohammed, Mandayam Anandalwar Sridhar, Shaukath Ara Khanum, & Rajni Kant. "Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide." European Journal of Chemistry [Online], 10.3 (2019): 234-238. Web. 19 Aug. 2022
Al-Ostoot, Fares, Stondus, Jigmat, Anthal, Sumati, Venkatesh, Geetha, Mohammed, Yasser, Sridhar, Mandayam, Khanum, Shaukath, AND Kant, Rajni. "Synthesis, spectroscopic and X-ray crystallographic analysis of N-(2-(2-(4-chlorophenoxy)acetamido)phenyl)-1H-indole-2-carboxamide" European Journal of Chemistry [Online], Volume 10 Number 3 (30 September 2019)

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