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Molecular self-assembly in indole-based benzamide derivative: Crystal structure, Hirshfeld surfaces and antimicrobial activity
Ilkay Gumus (1,*)
, Ummuhan Solmaz (2) , Serpil Gonca (3) , Hakan Arslan (4) (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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European Journal of Chemistry
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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
[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]. 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
[5]. 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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DOI Link: https://doi.org/10.5155/eurjchem.8.4.349-357.1637
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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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