European Journal of Chemistry 2017, 8(4), 349-357 | doi: https://doi.org/10.5155/eurjchem.8.4.349-357.1637 | Get rights and content

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Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity


Ilkay Gumus (1,*) orcid , Ummuhan Solmaz (2) orcid , Serpil Gonca (3) orcid , Hakan Arslan (4) orcid

(1) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(2) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(3) Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Mersin University, Mersin, TR 33343, Turkey
(4) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(*) Corresponding Author

Received: 12 Oct 2017 | Revised: 28 Oct 2017 | Accepted: 28 Oct 2017 | Published: 31 Dec 2017 | Issue Date: December 2017

Abstract


Two new compounds, 1H-indole-7-amine (1) and N-(1H-indol-7-yl)-2-methylbenzamide (2) were synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound 2 was further elucidated by single-crystal X-ray diffraction technique. Moreover, the crystal packing of compound 2 is analyzed in terms of non-covalent N-H···O, C-H···π, and parallel displaced π···π interactions. Hirshfeld surface analysis and decomposed fingerprint plots of the compound 2 were performed to visualize the presence of strong hydrogen bond N-H···O and C-H···π stacking interactions. Hirshfeld surface analysis and decomposed fingerprint plots show that the structure of compound 2 is stabilized by H···H, N-H···O, C-H···π and π···π intermolecular interactions and these interactions contribute mostly to molecular self-assembly in the crystal. In addition, compound 2 was evaluated for both their in-vitro antibacterial and antifungal activity. The obtained results have been reported, explained and compared with fluconazole and ampicillin used as reference drugs.


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Editor-in-Chief
European Journal of Chemistry

Keywords


Antimicrobial activity; Single crystal structure; Molecular self-assembly; Hirshfeld surface analysis; Deformation electron density; Indole-based benzamide derivative

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DOI: 10.5155/eurjchem.8.4.349-357.1637

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Funding information


This work was supported by Mersin University Research Fund [Project No: 2015-AP4-1162].

Citations

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[1]. Ilkay Gumus, Ummuhan Solmaz, Gun Binzet, Ebru Keskin, Birdal Arslan, Hakan Arslan
Supramolecular self-assembly of new thiourea derivatives directed by intermolecular hydrogen bonds and weak interactions: crystal structures and Hirshfeld surface analysis
Research on Chemical Intermediates  45(2), 169, 2019
DOI: 10.1007/s11164-018-3596-5
/


[2]. Ebru Keskin, Hakan Arslan
Synthesis, crystal structure, DFT calculations, and Hirshfeld surface analysis of an NNN pincer type compound
Journal of Molecular Structure  1283, 135252, 2023
DOI: 10.1016/j.molstruc.2023.135252
/


[3]. Ebru Keskin, Ummuhan Solmaz, Gun Binzet, Ilkay Gumus, Hakan Arslan
Synthesis, characterization and crystal structure of platinum(II) complexes with thiourea derivative ligands
European Journal of Chemistry  9(4), 360, 2018
DOI: 10.5155/eurjchem.9.4.360-368.1774
/


[4]. Ebru Keskin, Hakan Arslan
Palladium complexes containing NNN pincer type ligands and their activities in Suzuki-Miyaura cross coupling reaction
Heliyon  9(7), e17608, 2023
DOI: 10.1016/j.heliyon.2023.e17608
/


[5]. Soundararajan Krishnan, Thanigaimani Kaliyaperumal, Ramalingam Marimuthu, Sethuraman Velusamy
Crystal structure, Hirshfeld surface, and DFT studies of 4-((pyrrolidin-1-ylsulfonyl)methyl)aniline
European Journal of Chemistry  12(4), 419, 2021
DOI: 10.5155/eurjchem.12.4.419-431.2177
/


[6]. U. Solmaz, E. Keskin, I. Gumus, P. K. Cevik, G. Binzet, H. Arslan
PLATINUM(II) COMPLEX CONTAINING N-(BIS (-2,4-DIMETHOXY-BENZYL)CARBAMOTHIOYL)- 4-METHYLBENZAMIDE LIGAND: SYNTHESIS, CRYSTAL STRUCTURE, HIRSHFELD SURFACE ANALYSIS, AND ANTIMICROBIAL ACTIVITY
Journal of Structural Chemistry  63(1), 62, 2022
DOI: 10.1134/S0022476622010073
/


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Supporting information


The Supplementary Material for this article can be found online at: Supplementary files

How to cite


Gumus, I.; Solmaz, U.; Gonca, S.; Arslan, H. Eur. J. Chem. 2017, 8(4), 349-357. doi:10.5155/eurjchem.8.4.349-357.1637
Gumus, I.; Solmaz, U.; Gonca, S.; Arslan, H. Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity. Eur. J. Chem. 2017, 8(4), 349-357. doi:10.5155/eurjchem.8.4.349-357.1637
Gumus, I., Solmaz, U., Gonca, S., & Arslan, H. (2017). Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity. European Journal of Chemistry, 8(4), 349-357. doi:10.5155/eurjchem.8.4.349-357.1637
Gumus, Ilkay, Ummuhan Solmaz, Serpil Gonca, & Hakan Arslan. "Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity." European Journal of Chemistry [Online], 8.4 (2017): 349-357. Web. 11 Dec. 2023
Gumus, Ilkay, Solmaz, Ummuhan, Gonca, Serpil, AND Arslan, Hakan. "Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

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