Crystal and molecular structure of bis(N-(diethylcarbamothioyl)cyclohexane carboxamido)copper(II) complex European Journal of Chemistry 11 (4) (2020) 319-323 European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2020 The Authors – Atlanta Publishing House LLC – Printed in the USA. This work is published and licensed by Atlanta Publishing House LLC – CC BY NC – Some Rights Reserved. http://dx.doi.org/10.5155/eurjchem.11.4.319-323.2047 European Journal of Chemistry View Journal Online View Article Online Crystal and molecular structure of bis(N-(diethylcarbamothioyl)cyclohexane carboxamido)copper(II) complex Cemal Koray Ozer 1, Gun Binzet 2,* and Hakan Arslan 1 1 Department of Chemistry, Faculty of Arts and Science, Mersin University, Mersin, TR 33343, Turkey c.korayozer@gmail.com (C.K.O.), hakan.arslan@mersin.edu.tr (H.A.) 2 Department of Chemistry, Faculty of Education, Mersin University, Mersin, TR-33343, Turkey gunbinzet@mersin.edu.tr (G.B.) * Corresponding author at: Department of Chemistry, Faculty of Education, Mersin University, Mersin, TR-33343, Turkey. e-mail: gunbinzet@mersin.edu.tr (G. Binzet). 10.5155/eurjchem.11.4.319-323.2047 Received: 13 October 2020 Received in revised form: 05 November 2020 Accepted: 15 November 2020 Published online: 31 December 2020 Printed: 31 December 2020 Herein, we describe the synthesis and characterization of bis(N-(diethylcarbamothioyl)cyclohexane carboxamido)copper(II) complex, cis-[Cu(L-κ2S,O)2], has been prepared by the reaction of N-(diethyl carbamothioyl)cyclohexanecarboxamide ligand with copper(II) acetate. The green colored crystals of the complex were obtained by slow evaporation of their dichloromethane:ethanol solution (2:1, v:v). The crystal structure of cis-[Cu(L-κ2S,O)2] was obtained by single-crystal X-ray diffraction. The crystal structure reveals an monoclinic C2 (no. 5) space group with cell parameters a = 14.848(3) Å, b = 10.543(2) Å, c = 10.511(2) Å, β = 123.84(3)°, V = 1366.7(7) Å3, Z = 2, T = 153(2) K, μ(MoKα) = 0.979 mm-1, Dcalc = 1.327 g/cm3, 4979 reflections measured (6.6° ≤ 2Θ ≤ 50.68°), 2243 unique (Rint = 0.0223, Rsigma = 0.0444) which were used in all calculations. The final R1 was 0.0225 (>2sigma(I)) and wR2 was 0.0490 (all data). The angular structural index parameter, τ4, is equal to 0.40, which confirms the distorted square planar geometry for the title compound. The puckering parameters (q2 = 0.015(3) Å, q3 = 0.576(3) Å, QT = 0.577(3) Å, θ = 1.6(3)° and φ = 20(11)°) of the title complex show that the cyclohexane ring adopts a chair conformation. The two ethyl groups of the diethyl amine group have anti-orientation with respect to one another. The crystal packing shows the molecules stacked in parallel sheets along [010], accompanied by C3-H3A···O1ⁱ (i -x, +y, 1-z) intermolecular contact. Thiourea Copper complex Crystal structure Chair conformation Single crystal X-ray diffraction Distorted square planar geometry Cite this: Eur. J. Chem. 2020, 11(4), 319-323 Journal website: www.eurjchem.com 1. Introduction Thiourea derivative compounds have a long history as ligands in coordination chemistry due to their ease of synthesis, variability in structural design, and wide range of applications. The nitrogen, oxygen, and sulfur donor atoms of thiourea derivatives provide a multitude of bonding possibilities [1-6]. The thiourea derivatives are able to coordinate to a range of metal centers as neutral ligands, monoanions, or dianions. Both the ligands and their metal complexes display a wide range of biological activity including antibacterial [7-12], antifungal [13- 19], antitumor [20-24], antiviral [25] antithyroid [26, 27], anthelmintic [28], rodenticidal [29], insecticidal [30], herbicidal [31], anti-parasitic [32], antileishmanial [24], antioxidant [33] and plant-growth regulator [34] properties. Additionally, espe- cially benzoyl thiourea derivatives possess wide applications in several areas of life sciences as catalysts [35-39], fluorescent sensor [40,41], anion selective sensors [42-46] liquid-liquid extraction [47,48], preconcentration [49-51] and highly efficient chromatographic separation [52,53]. Our research group is interested in the synthesis, charac- terization, crystal structure, biological applications, and coor- dination chemistry of novel thiourea derivative compounds [7,8,54-62]. As a part of our ongoing studies into the structure and utility of oxygen and sulfur containing thiourea derivatives, we report the crystal structure of bis(N-(diethylcarbamothioyl) cyclohexane carboxamido)copper(II) complex. 2. Experimental 2.1. Instrumentation 1H NMR spectrum of the ligand was recorded on a Bruker DPX-400 spectrometer at 400 MHz using CDCl3 as the solvent, with tetramethylsilane as an internal standard. Room tempe- rature attenuated total reflection Fourier transform infrared (FT-IR ATR) spectra of all synthesized compounds were recorded using a Varian FTS1000 FT-IR spectrometer with Diamond/ZnSe prism (4000-525 cm-1; number of scans: 250; resolution: 1 cm-1). The X-ray diffraction data were recorded on a Bruker APEX-II CCD diffractometer. A suitable crystal was selected and coated with Paratone oil and mounted on a Nylon loop on a Bruker APEX-II CCD diffractometer. The crystal was kept at T = 153(2) K during data collection. The data were collected with MoKα (λ = 0.71073 Å) radiation at a crystal-to- detector distance of 40 mm. ABSTRACT RESEARCH ARTICLE KEYWORDS http://dx.doi.org/10.5155/eurjchem.11.4.319-323.2047 http://www.eurjchem.com/ http://dx.doi.org/10.5155/eurjchem.11.4.319-323.2047 mailto:c.korayozer@gmail.com mailto:hakan.arslan@mersin.edu.tr mailto:gunbinzet@mersin.edu.tr mailto:gunbinzet@mersin.edu.tr http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.11.4.319-323.2047&domain=pdf&date_stamp=2020-12-31 320 Ozer et al. / European Journal of Chemistry 11 (4) (2020) 319-323 2020 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.11.4.319-323.2047 Scheme 1. Synthesis of ligand and its copper complex. Using Olex2 [63], the structure was solved with the Superflip [64] structure solution program, using the Charge Flipping solution method and refined by full-matrix least- squares technique on F2 using ShelXL [65] with a refinement of F2 against all reflections. Hydrogen atoms were constrained by difference maps and were refined isotropically, and all non- hydrogen atoms were refined anisotropically. All geometrical data were calculated using PLATON [66]. Molecular structure and packing diagrams were generated using OLEX2 and MERCURY, respectively [63,67]. 2.2. Reagents All chemicals used for the preparation of the compounds were of reagent grade quality. Acetone was distilled before use. Potassium thiocyanate and cyclohexanecarbonyl chloride were purchased from Merck and used as received. All other chemicals and solvents were obtained from commercial suppliers and used without further purification. 2.3. Synthesis 2.3.1. Synthesis of N-(diethylcarbamothioyl)cyclohexane carboxamide, HL N-(Diethylcarbamothioyl)cyclohexanecarboxamide (HL) was prepared according to previously published methods [54- 62,68]. A solution of cyclohexanecarbonyl chloride (5.00 mmoles, 0.683 mL) in acetone (30 mL) was added dropwise to a suspension of potassium thiocyanate (5.00 mmoles, 0.4908 g) in acetone (30 mL). The reaction mixture was heated (50 °C) under reflux for 30 min and then cooled to room temperature. A solution of diethyl amine (5.00 mmoles, 0.520 mL) in acetone (30 mL) was added and the resulting mixture was stirred for 2 h. Hydrochloric acid (0.1 N, 100 mL) was added and the solution filtered. The solid product was washed with water and purified by recrystallization from an ethanol:dichloromethane mixture (1:2, v:v) (Scheme 1). Yield: 76% (0.9211 g). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.00 (s, 1H, NH), 3.93 (t, 2H, NCH2), 3.43 (t, 2H, NCH2), 2.24 (tt, 1H, CH, Ch), 1.89 (d, 1H, CH, Ch), 1.84 (d, 1H, CH, Ch), 1.78 (m, 1H, CH, Ch), 1.74 (m, 1H, CH, Ch), 1.67 (m, 1H, CH, Ch), 1.64 (m, 1H, CH, Ch), 1.41 (m, 4H, CH, Ch), 1.32 (t, 3H, CH3), 1.23 (t, 3H, CH3). FT-IR (cm-1): 3240 ν(NH), 2976, 2926, 2853 ν(CH), 1661 ν(C=O), 1312 ν(C=S) [62]. 2.3.2. Synthesis of copper complex, Cu(L-κ2S,O)2 Paramagnetic copper complex was prepared according to the method described in the literature [62]. A solution of copper(II) acetate (10.0 mmoles, 1.8163 g) in ethanol (30 mL) was added dropwise to a solution of N-(diethylcarbamothioyl) cyclohexanecarboxamide (22.0 mmoles, 5.3324 g) in a 1:2 ratio with a small excess of N-(diethylcarbamothioyl)cyclohexane carboxamide in ethanol (30 mL) at room temperature and the resulting mixture was stirred for 30 min. The solid complex was filtered and re-crystallized from ethanol: dichloromethane mixture (1:2, v:v) (Scheme 1). Bis(N-(diethylcarbamothioyl) cyclohexanecarboxamido)copper(II) [Cu(L-κ2S,O)2]: Color: Green. M.p.: 71-73 °C. Yield: 81 % (4.4161 g). FT-IR (ATR, cm-1): 2972, 2924, 2854 ν(CH), 1522 ν(CN), 1489 ν(CO) [62]. 3. Results and discussion The block-shaped green colored crystals of the copper complex was obtained by slow evaporation of their dichloro- methane:ethanol solution (2:1, v:v). The molecular structure of the copper complex was determined by single crystal X-ray diffraction. The copper complex crystallized in the monoclinic space group C2 (No. 5) and the crystal and structure refinement data are given in Table 1. Selected bond lengths and angles are given in Table 2. The molecular structure of the complex with the atomic numbering scheme is shown in Figure 1. The reaction between N-(diethylcarbamothioyl)cyclohexane carboxamide ligands and copper(II) ion produces a metal complex with the expected metal:ligand ratio of 1:2. The chelating two thiourea ligands are coordinated with a copper(II) ion in a bidentate mode, forming two six-membered chelate rings (Cu1-S1-C5-N1-C6-O1). The six-membered rings are formed via oxygen and sulphur atoms, and the dihedral angle between these chelate rings in the copper complex is 44.96° (Figure 2). The bond angles around the copper ion are S1-Cu1-O1 = 95.97(5)° and S1i-Cu1-S1 = 92.94(4)° (i -x, +y, 1-z) for cis-[CuL2], so the bite angles of the complex deviate slightly from the ideal angle (90°) [69]. The copper center, surrounded by oxygen and sulphur atoms in the complex form, has a distorted square planar geometry as shown in Figure 1. The sum of the equatorial angles S1-Cu1-O1, S1-Cu1-S1i, O1-Cu1- O1i, and O1i-Cu1-S1i (i -x, +y, 1-z) are 373.20°, which is consistent with distorted square planar geometry. In addition, it is clear that the τ4 parameter is essential for four-coordinate transition metal complexes since square planar and tetrahedral geometries are the extremes [70]. The angular structural index parameter, τ4 = (360-(β+α))/141, evaluated from the two largest angles in the four-coordinated geometry, which has ideal values of 1 for a perfect tetrahedral geometry and 0 for a perfect square planar geometry, is equal to 0.40, which confirms the distorted square planar geometry for the title compound. The distance of copper atom from the best plane through the coordination sphere is 0.000 Å. The deviations from the best plane (O1/S1/Cu/S1i/Oi ; i -x, +y, 1-z) are 0.548(2) and 0.428(2) Å for O1 and S1 atoms, respectively. Ozer et al. / European Journal of Chemistry 11 (4) (2020) 319-323 321 2020 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.11.4.319-323.2047 Table 1. Crystal data and structure refinement for [Cu(L-κ2S,O)2]. Empirical formula C24H42CuN4O2S2 Formula weight 546.28 Temperature (K) 153(2) Crystal system Monoclinic Space group C2 a (Å) 14.848(3) b (Å) 10.543(2) c (Å) 10.511(2) β (°) 123.84(3) Volume (Å3) 1366.7(7) Z 2 ρcalc (g/cm3) 1.327 μ (mm-1) 0.979 F(000) 582.0 Crystal size (mm3) 0.22 × 0.22 × 0.07 Radiation MoKα (λ = 0.71073 Å) 2Θ range for data collection (°) 6.6 to 50.68 Index ranges -17 ≤ h ≤ 17, -12 ≤ k ≤ 10, -12 ≤ l ≤ 12 Reflections collected 4979 Independent reflections 2243 [Rint = 0.0223, Rsigma = 0.0444] Data / restraints / parameters 2243/1/153 Goodness-of-fit on F2 1.027 Final R indexes [I≥2σ (I)] R1 = 0.0225, wR2 = 0.0476 Final R indexes [all data] R1 = 0.0249, wR2 = 0.0490 Largest diff. peak /hole (e.Å-3) 0.29/-0.20 Flack parameter 0.620(11) Table 2. Bond lengths and angles for [Cu(L-κ2S,O)2]. Bond Distance (Å) Bond Distance (Å) Cu1-S11 2.2341(8) N2-C5 1.339(3) Cu1-S1 2.2341(8) C1-C2 1.510(3) Cu1-O1 1.9197(16) C3-C4 1.520(4) Cu1-O11 1.9197(16) C6-C7 1.522(3) S1-C5 1.739(2) C7-C8 1.532(3) O1-C6 1.276(2) C7-C12 1.529(3) N1-C5 1.345(3) C8-C9 1.523(3) N1-C6 1.322(3) C9-C10 1.531(3) N2-C1 1.477(3) C10-C11 1.517(4) N2-C3 1.464(3) C11-C12 1.523(3) Bond Angles (°) Bond Angles (°) S11-Cu1-S1 92.94(4) N1-C5-S1 127.22(18) O11-Cu1-S11 95.97(5) N2-C5-S1 117.53(19) O11-Cu1-S1 152.08(5) N2-C5-N1 115.05(19) O1-Cu1-S1 95.97(5) O1-C6-N1 128.8(2) O1-Cu1-S11 152.08(5) O1-C6-C7 114.92(19) O1-Cu1-O11 88.39(10) N1-C6-C7 116.29(18) C5-S1-Cu1 104.90(9) C6-C7-C8 111.68(18) C6-O1-Cu1 129.69(16) C6-C7-C12 114.17(18) C6-N1-C5 126.30(19) C12-C7-C8 109.94(19) C3-N2-C1 115.54(17) C9-C8-C7 111.11(19) C5-N2-C1 120.86(19) C8-C9-C10 110.84(19) C5-N2-C3 123.59(19) C11-C10-C9 111.1(2) N2-C1-C2 111.62(19) C10-C11-C12 111.5(2) N2-C3-C4 112.4(2) C11-C12-C7 111.12(19) 1 Symmetry code: -x, +y, 1-z. Figure 1. The molecular structure of bis(N-(diethylcarbamothioyl)cyclohexane carboxamido)copper(II) complex with atom labeling scheme. Displacements of ellipsoids are shown at the 50% probability level, i -x, +y, 1-z. 322 Ozer et al. / European Journal of Chemistry 11 (4) (2020) 319-323 2020 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.11.4.319-323.2047 Figure 2. Packing diagram for bis(N-(diethylcarbamothioyl)cyclohexane carboxamido)copper(II) complex, viewed along [010]. Intermolecular C-H···O contact is indicated by dashed lines. The chelate ring systems, Cu1–O1–C6–N1–C5–S1, are nearly planar as well with the largest deviations from the best plane being 0.175(2) Å for C5 atom. The C6-O1 and C5-S1 bond lengths are 1.276(2) and 1.739(2) Å for copper(II) complex which are slightly longer than the corresponding distance found in free ligand (C=O, 1.228(3) and C=S, 1.664(2) Å) [62]. This indicates the existence of electron delocalization over the six-member chelate rings (Cu1-S1-C5-N1-C6-O1 and Cu1-S1i -C5i -N1i -C6i -O1i; i -x, +y, 1- z) due to the coordination of the oxygen and sulfur atoms with the copper(II) ion. This result was also confirmed by the short C-N bond distance (N1-C5, 1.345(3) and N1-C6, 1.322(3) Å) which are shorter than the average for C-N single bond distance (1.48 Å) [71,72]. The molecular structure is very close to the related bis(N-(di-n-propylcarbamothioyl)cyclohexanecarbox- amido) copper(II) complex, [71] and shows similar short Metal- S, Metal-O, C-O, C-N and C-S bonds indicating the known π- bonding character in the chelate rings. All other bond lengths are within normal ranges (Table 2) [72]. The cyclohexane ring in the title complex exhibits a puckered conformation with puckering parameters q2 = 0.015(3) Å, q3 = 0.576(3) Å, QT = 0.577(3) Å, θ = 1.6(3)° and φ = 20(11)°. These puckering parameters show that the cyclo- hexane ring adopts a chair conformation [73]. The torsion angles of the diethyl amine group are C5-N2- C3-C4 = -90.1(3)° and C5-N2-C1-C2 = -88.2(3)°. According to these torsion angles, the ethyl substituents (C5-N2-C3-C4 and C5-N2-C1-C2) are in (-) anticlinal (-ac) and (-) synclinal (-sc) orientation, respectively [74]. In addition, the two ethyl groups of the diethyl amine group are anti-orientation with respect to one another. The crystal packing shows the molecules stacked in parallel sheets along [010] (Figure 2), accompanied by the following intermolecular contact: C3-H3A···O1ⁱ, with C-H = 0.96 Å, H···O 2.70 Å, and C-H···O 134°; symmetry code i -x, +y, 1-z. Possible intramolecular interactions are C1-H1B···N1, with C-H = 0.96 Å, H···O 2.33 Å, and C-H···O 100° and C3-H3B···S1, with C-H = 0.96 Å, H···S 2.57 Å, and C-H···O 106°. 4. Conclusion A copper(II) complex, having the general formula cis-[Cu(L- κ2S,O)2], has been prepared with N-(diethylcarbamothioyl) cyclohexanecarboxamide ligand and copper(II) acetate, and characterized by a single crystal X-ray diffraction study, where the ligands coordinate to copper(II) ion in a cis conformation. The obtained copper complex, cis-[Cu(L-κ2S,O)2], crystallized in the monoclinic space group C2. The copper center has a slightly distorted square planar geometry and the puckering parameters of the title complex show that the cyclohexane ring adopts a chair conformation. The crystal packing shows the molecules stacked in parallel sheets along [010], accompanied by C3-H3A···O1ⁱ (i -x, +y, 1-z) intermolecular contact. Acknowledgements A part of this work was supported by the Mersin University Research Fund [Project No: BAP-SBETB (CKÖ) 2007-1]. Supporting information CCDC-2039559 contains the supplementary crystallo- graphic data for this paper. These data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/, or by e- mailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033. Disclosure statement Conflict of interest: The authors declare that they have no conflict of interest. Author contributions: All authors contributed equally to this work. Ethical approval: All ethical guidelines have been adhered. Sample availability: Samples of the compounds are available from the author. Funding Mersin Üniversitesi http://dx.doi.org/10.13039/501100004172 ORCID Cemal Koray Ozer http://orcid.org/0000-0001-9957-4167 Gun Binzet http://orcid.org/0000-0002-9601-9528 Hakan Arslan http://orcid.org/0000-0003-0046-9442 https://www.ccdc.cam.ac.uk/structures/ mailto:data_request@ccdc.cam.ac.uk http://dx.doi.org/10.13039/501100004172 http://orcid.org/0000-0001-9957-4167 http://orcid.org/0000-0002-9601-9528 http://orcid.org/0000-0003-0046-9442 Ozer et al. / European Journal of Chemistry 11 (4) (2020) 319-323 323 2020 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.11.4.319-323.2047 References [1]. Beyer, L.; Hoyer, E.; Liebscher, J.; Hartmann, H. Z. Chem. 2010, 21(3), 81-91. [2]. Bourne, S.; Koch, K. R. J. Chem. Soc., Dalton Trans. 1993, 13, 2071-2072. [3]. Koch, K. R.; Wang, Y.; Coetzee, A. J. Chem. Soc., Dalton Trans. 1999, 6, 1013-1016. [4]. Che, D. J.; Li, G.; Yao, X. L.; Wu, Q. J.; Wang, W. L.; Zhu, Y. J. Organometal. Chem. 1999, 584(1), 190-196. [5]. 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This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (http://www.eurjchem.com/index.php/eurjchem/pages/view/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry). http://www.eurjchem.com/index.php/eurjchem/pages/view/terms http://creativecommons.org/licenses/by-nc/4.0 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms 1. Introduction 2. Experimental 2.1. Instrumentation 2.2. Reagents 2.3. Synthesis 2.3.1. Synthesis of N-(diethylcarbamothioyl)cyclohexane carboxamide, HL 2.3.2. Synthesis of copper complex, Cu(L-κ2S,O)2 3. Results and discussion 4. Conclusion Acknowledgements Supporting information Disclosure statement Funding ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: