European Journal of Chemistry 2017, 8(4), 349-357. doi:10.5155/eurjchem.8.4.349-357.1637

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, Accepted: 28 Oct 2017, Published: 31 Dec 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.


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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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
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[2]. Anna Adach, Marek Daszkiewicz, Malgorzata Tyszka-Czochara
Comparative X-ray, vibrational, theoretical and biological studies of new in situ formed [CoLSX]2[CdX4] halogenocadmate(II) complexes containing N-scorpionate ligand
Polyhedron  , 114229, 2019
DOI: 10.1016/j.poly.2019.114229
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[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
/


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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. 15 Nov. 2019
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)

DOI Link: https://doi.org/10.5155/eurjchem.8.4.349-357.1637

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