European Journal of Chemistry 2021, 12(4), 439-449 | doi: https://doi.org/10.5155/eurjchem.12.4.439-449.2196 | Get rights and content

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Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide


Cemal Koray Ozer (1) orcid , Ummuhan Solmaz (2,*) orcid , Hakan Arslan (3) orcid

(1) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(2) Department of Chemistry and Chemical Processing Technologies, Technical Science Vocational School, Mersin University, Mersin, TR 33343, Turkey
(3) Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey
(*) Corresponding Author

Received: 22 Oct 2021 | Revised: 14 Nov 2021 | Accepted: 20 Nov 2021 | Published: 31 Dec 2021 | Issue Date: December 2021

Abstract


N-(2-Chlorophenylcarbamothioyl)cyclohexanecarboxamide was characterized by a single crystal X-ray diffraction study. Crystal data for this compound, C14H17ClN2OS; Monoclinic, space group P21/n with Z = 4, a = 5.2385(10) Å, b = 17.902(4) Å, c = 15.021(3) Å, β = 90.86(3)°, V = 1408.5(5) Å3, T = 153(2) K, μ(MoKα) = 0.413 mm-1, Dcalc = 1.400 g/cm3, 9840 reflections measured (7.082° ≤ 2Θ ≤ 50.378°), 2519 unique (Rint = 0.0406, Rsigma = 0.0335) which were used in all calculations. The final R1 was 0.0397 (I > 2σ(I)) and wR2 was 0.0887 (all data). The puckering parameters (q2 = 0.019(3) Å, q3 = 0.578(3) Å, θ = 1.0(3)° and φ = 51(8)°) of the title compound show that the cyclohexane ring adopts a chair conformation. The molecular conformation of the title compound is stabilized by intramolecular hydrogen bonds (N2-H2⋅⋅⋅Cl1, N2-H2⋅⋅⋅O1, and C2-H2A⋅⋅⋅S1) and intermolecular hydrogen bonds (N1-H1⋅⋅⋅S1i and C9-HA⋅⋅⋅S1ii: 2-x, 2-y, 1-z). The intramolecular hydrogen bonds (N2-H2⋅⋅⋅O1 and C2-H2A⋅⋅⋅S1) are also form two pseudo-six-membered rings. Density functional theory optimized structure in the gaseous phase at B3LYP/6-311G(d,p) level of theory has been compared with the experimentally defined molecular structure. The molecular orbitals HOMO and LUMO with the energy gap for the title compound are calculated and the estimated energy gap (ΔE) between the HOMO and LUMO energies levels of the title compound is 3.5399 eV, which implies that the title molecule is very reactive. The Hirshfeld surface analysis reveals that the most important contributions to crystal packing are from H···H (49.0%), H···C/C···H (12.5%), H···Cl/Cl···H (10.9%), and H···S/S···H (10.0%) interactions. The energy-framework calculations are used to analyze and visualize the three-dimensional topology of the crystal packing. The intermolecular energy analysis confirmed a significant contribution of dispersion to the stabilization of molecular packings in the title compound.


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Editor-in-Chief
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Keywords


Benzoylthiourea; Chair conformation; Cyclohexanecarboxamide; Crystal structure analysis; Hirshfeld surface analysis; Density Functional Theory (DFT)

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DOI: 10.5155/eurjchem.12.4.439-449.2196

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Funding information


Mersin University Research Fund [Project No: BAP-SBETB (CKÖ) 2007-1], Mersin, Turkey.

Citations

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[1]. Gün BİNZET
N-(Siklohekzil(metil)karbamotiyoil)-4-nitrobenzamit Bileşiğinin Sentezi, Kristal Yapısı, DFT Çalışmaları ve Hirshfeld Yüzey Analizi
Osmaniye Korkut Ata Üniversitesi Fen Bilimleri Enstitüsü Dergisi  , , 2022
DOI: 10.47495/okufbed.1090049
/

[2]. Aynur Alizada, Hakan Arslan
Experimental and theoretical studies of a thiourea derivative: 1-(4-chloro-benzoyl)-3-(2-trifluoromethyl-phenyl)thiourea
Journal of Molecular Structure  1279, 134996, 2023
DOI: 10.1016/j.molstruc.2023.134996
/

[3]. 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
/

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Ozer, C.; Solmaz, U.; Arslan, H. Eur. J. Chem. 2021, 12(4), 439-449. doi:10.5155/eurjchem.12.4.439-449.2196
Ozer, C.; Solmaz, U.; Arslan, H. Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide. Eur. J. Chem. 2021, 12(4), 439-449. doi:10.5155/eurjchem.12.4.439-449.2196
Ozer, C., Solmaz, U., & Arslan, H. (2021). Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide. European Journal of Chemistry, 12(4), 439-449. doi:10.5155/eurjchem.12.4.439-449.2196
Ozer, Cemal, Ummuhan Solmaz, & Hakan Arslan. "Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide." European Journal of Chemistry [Online], 12.4 (2021): 439-449. Web. 28 May. 2023
Ozer, Cemal, Solmaz, Ummuhan, AND Arslan, Hakan. "Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide" European Journal of Chemistry [Online], Volume 12 Number 4 (31 December 2021)

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