European Journal of Chemistry 2017, 8(4), 410-416 | doi: https://doi.org/10.5155/eurjchem.8.4.410-416.1650 | Get rights and content

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N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity


Ilkay Gumus (1,*) orcid , Serpil Gonca (2) orcid , Birdal Arslan (3) orcid , Ebru Keskin (4) orcid , Ummuhan Solmaz (5) orcid , Hakan Arslan (6) orcid

(1) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(2) Department of Pharmaceutical Microbiology, Faculty of Pharmacy, Mersin University, Mersin, TR 33343, Turkey
(3) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(4) Advanced Technology Research and Application Center, Mersin University, Mersin, TR 33343, Turkey
(5) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(6) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(*) Corresponding Author

Received: 20 Oct 2017 | Revised: 08 Nov 2017 | Accepted: 09 Nov 2017 | Published: 31 Dec 2017 | Issue Date: December 2017

Abstract


The compound N-(dibenzylcarbamothioyl)-3-methylbutanamide as a thiourea derivative was synthesized and structurally characterized by NMR and FT-IR spectroscopic techniques. The molecular structure of compound was also characterized by single crystal X-ray diffraction method. Crystal data for title compound C20H24N2OS: monoclinic, space group C2/c (no. 15), a = 19.6882(9) Å, b = 9.4045(4) Å, c = 19.5012(8) Å, β = 98.433(2)°, V = 3571.8(3) Å3, Z = 8, μ(CuKα) = 1.665 mm-1, 25057 reflections measured (9.168° ≤ 2Θ ≤ 144.196°), 3500 unique (Rint = 0.0322, Rsigma = 0.0200) which were used in all calculations. The final R1 was 0.0363 (I>2σ(I)) and wR2 was 0.0910 (all data). Intermolecular contacts obtained from X-ray single crystal diffraction study were also explored using both Hirshfeld surfaces and fingerprint plots. Hirshfeld surface analysis showed the occurrence of S···H, O···H and H···H contacts that display an important role to crystal packing stabilization of the thiourea derivative compound. In addition, the compound was evaluated for both their in-vitro antibacterial and antifungal activity.


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Editor-in-Chief
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Keywords


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

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DOI: 10.5155/eurjchem.8.4.410-416.1650

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Funding information


This work was supported by Mersin University Research Fund [Project No: 2016-AP4-1426].

Citations

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[1]. Ummuhan Solmaz, Hakan Arslan
Spectral, crystallographic, theoretical, and catalytic activity studies of the PdII complexes in different coordination modes of benzoylthiourea ligand
Journal of Molecular Structure  1269, 133839, 2022
DOI: 10.1016/j.molstruc.2022.133839
/

[2]. 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
/

[3]. 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
/

[4]. Muhammet Ebubekir Uysal, Ummuhan Solmaz, Hakan Arslan
Ru(II) and Ru(III) complexes containing N‐acylthiourea ligands: Supramolecular structures and synthons, reduction, and reaction pathway of aromatic nitro compounds
Applied Organometallic Chemistry  37(7), , 2023
DOI: 10.1002/aoc.7107
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[5]. Muhammet Ebubekir Uysal, Ummuhan Solmaz, Hakan Arslan
Ruthenium(III) acyl thiourea complex: A catalyst for transfer hydrogenation of nitroarenes
Polyhedron  247, 116707, 2024
DOI: 10.1016/j.poly.2023.116707
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[6]. Gun Binzet, Ersan Turunc, Ulrich Flörke, Nevzat Külcü, Hakan Arslan
Crystal Structure and Cyclic Voltammetric Studies on the Metal Complexes of N-(Dimethylcarbamothioyl)-4-fluorobenzamide
Journal of Chemistry  2018, 1, 2018
DOI: 10.1155/2018/6108242
/

[7]. 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
/

[8]. 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
/

[9]. 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.; Gonca, S.; Arslan, B.; Keskin, E.; Solmaz, U.; Arslan, H. Eur. J. Chem. 2017, 8(4), 410-416. doi:10.5155/eurjchem.8.4.410-416.1650
Gumus, I.; Gonca, S.; Arslan, B.; Keskin, E.; Solmaz, U.; Arslan, H. N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity. Eur. J. Chem. 2017, 8(4), 410-416. doi:10.5155/eurjchem.8.4.410-416.1650
Gumus, I., Gonca, S., Arslan, B., Keskin, E., Solmaz, U., & Arslan, H. (2017). N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity. European Journal of Chemistry, 8(4), 410-416. doi:10.5155/eurjchem.8.4.410-416.1650
Gumus, Ilkay, Serpil Gonca, Birdal Arslan, Ebru Keskin, Ummuhan Solmaz, & Hakan Arslan. "N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity." European Journal of Chemistry [Online], 8.4 (2017): 410-416. Web. 10 Dec. 2023
Gumus, Ilkay, Gonca, Serpil, Arslan, Birdal, Keskin, Ebru, Solmaz, Ummuhan, AND Arslan, Hakan. "N-(Dibenzylcarbamothioyl)-3-methylbutanamide: Crystal structure, Hirshfeld surfaces and antimicrobial activity" European Journal of Chemistry [Online], Volume 8 Number 4 (31 December 2017)

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