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Crystal structure, Hirshfeld surface analysis, and DFT studies of N-(2-chlorophenylcarbamothioyl)cyclohexanecarboxamide
Cemal Koray Ozer (1)
, Ummuhan Solmaz (2,*) , Hakan Arslan (3) (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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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
[1]. Gün BİNZET
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Osmaniye Korkut Ata Üniversitesi Fen Bilimleri Enstitüsü Dergisi 5(2), 681, 2022
DOI: 10.47495/okufbed.1090049
[2]. Aynur Alizada, Hakan Arslan
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[4]. Ebru Keskin, Hakan Arslan
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[6]. Emmanuel Israel Edache, Adamu Uzairu, Paul Andrew Mamza, Gideon Adamu Shallangwa, Muhammad Tukur Ibrahim
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