X-ray crystal structure analysis of N'-acetyl-N'-phenyl-2-naphthohydrazide European Journal of Chemistry 13 (3) (2022) 253-258 European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2022 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. https://dx.doi.org/10.5155/eurjchem.13.3.253-258.2235 European Journal of Chemistry View Journal Online View Article Online X-ray crystal structure analysis of N'-acetyl-N'-phenyl-2-naphthohydrazide Varun Sharma 1, Indrajit Karmakar 2, Goutam Brahmachari 2 and Vivek Kumar Gupta 1,* 1 Department of Physics, University of Jammu, Jammu Tawi-180006, India 2 Laboratory of Natural Products and Organic Synthesis, Department of Chemistry, Visva-Bharati (A Central University), Santiniketan-731235, West Bengal, India * Corresponding author at: Department of Physics, University of Jammu, Jammu Tawi-180006, India. e-mail: vivek.gupta2k9@gmail.com (V.K. Gupta). 10.5155/eurjchem.13.3.253-258.2235 Received: 02 March 2022 Received in revised form: 29 April 2022 Accepted: 11 May 2022 Published online: 30 September 2022 Printed: 30 September 2022 N'-Acetyl-N'-phenyl-2-naphthohydrazide, a biologically relevant organic molecule, was synthesized following a reported method and characterized based on its single X-ray crystallographic studies. The present manuscript deals with its detailed molecular interactions and X-ray crystal structure. Its space group is P-1 with the following unit cell parameters: a = 8.9164(7), b = 9.7058(9), c = 17.7384(12) Å, α = 88.308(7)°, β = 89.744(6)°, γ = 86.744(7)° and Z = 2. Crystal structure was solved by direct method and refined by full matrix least squares procedure to a final R value of 0.0580 and to a GOOF value of 1.066. The X-ray diffraction analyses showed that the asymmetric unit contains two crystallographically independent molecules. The crystal structure is stabilized by elaborate network of N-H···O and C-H···O hydrogen bonds along with C-H···π and π···π interactions to form supramolecular structures. Disorder Hydrazones Single-crystal X-ray diffraction Hirshfeld surface Hydrogen bonding Cite this: Eur. J. Chem. 2022, 13(3), 253-258 Journal website: www.eurjchem.com 1. Introduction Hydrazones are important class of biologically potent and pharmaceutically useful organic compounds [1-3]. They find many applications in fluorescent chemosensors [4,5], as auxiliaries in asymmetric synthesis [6], photo switches in photopharmacology [7], and linkers in preparing bifunctional molecules [8-10] and as ligands or directing groups in organic synthesis [11-13]. N,N'-Diacylhydrazones are functionalized hydrazone derivatives which are reported to exhibit various biological activities, including antitumor, antidiabetic, anti-inflammation, and anti-infection [14-20]. The title compound, N'-acetyl-N'- phenyl-2-naphthohydrazide (1) was synthesized following a reported method [21] as shown in Scheme 1, and characterized based on its single X-ray crystallographic studies. 2. Experimental 2.1. General For crystallization, 50 mg of compound N'-acetyl-N'- phenyl-2-naphthohydrazide (1) was dissolved in 5 mL DMSO and left for several days at ambient temperature which yielded yellowish block shaped crystals which was suitable for X-ray diffraction analysis, were synthesized following the reported method as described in literature [21]. 2.2. Crystal structure determination and refinement The cell dimensions were determined by least-squares fit of angular settings of 3226 reflections in the θ range 2.27 to 27.97°. The value of Rint = 0.0187 and Rsigma =0.0381 shows satisfactory quality of the data. The molecular structure solution was obtained by direct method procedure as using SHELXT [22]. Six cycles of full-matrix least-squares refinement was carried out and it brought the final R-factor to 0.0580 and to GOOF value of 1.066. All non-hydrogen atoms of the molecule were located in the best E-map and refined in anisotropic approximation using SHELXL [22]. The position of all the Hydrogen atoms bonded to carbon atoms were geometrically fixed and allowed to ride on the corresponding non-H atoms (C-H = 0.93-0.96 Å, and Uiso(H) = 1.5 Ueq of the attached C atoms for methyl groups and 1.2 Ueq(C) for other H atoms) except for H12, H35 and H35’ atoms attached to nitrogen atoms N12, N35 and N35’. The residual electron density in the final difference Fourier map between -0.27 < ∆ρ < 0.61. The geometry of the title molecule was calculated using WinGX [23], PARST [24] and PLATON [25] software. Crystallographic data are summarized in Table 1. ABSTRACT RESEARCH ARTICLE KEYWORDS https://dx.doi.org/10.5155/eurjchem.13.3.253-258.2235 https://www.eurjchem.com/ https://dx.doi.org/10.5155/eurjchem.13.3.253-258.2235 mailto:vivek.gupta2k9@gmail.com http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.13.3.253-258.2235&domain=pdf&date_stamp=2022-09-30 254 Sharma et al. / European Journal of Chemistry 13 (3) (2022) 253-258 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.3.253-258.2235 Table 1. Crystallographic characteristics, details of X-ray data collection, and structure refinement parameters for compound 1. Empirical formula C19H16N2O2 Formula weight 304.34 Temperature (K) 150.01(10) Crystal system Triclinic Space group P-1 a, (Å) 8.9164(7) b, (Å) 9.7058(9) c, (Å) 17.7384(12) α (°) 88.308(7) β (°) 89.744(6) γ (°) 86.744(7) Volume (Å3) 1531.9(2) Z 4 ρcalc (g/cm3) 1.320 μ (mm-1) 0.087 F(000) 640.0 Crystal size (mm3) 0.3 × 0.2 × 0.2 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 4.206 to 51.996 Index ranges -10 ≤ h ≤ 10, -11 ≤ k ≤ 11, -21 ≤ l ≤ 12 Reflections collected 8450 Independent reflections 5935 [Rint = 0.0187, Rsigma = 0.0381] Data/restraints/parameters 5935/936/547 Goodness-of-fit on F2 1.060 Final R indexes [I≥2σ (I)] R1 = 0.0580, wR2 = 0.1421 Final R indexes [all data] R1 = 0.0743, wR2 = 0.1579 Largest diff. peak/hole (e.Å-3) 0.61/-0.27 Scheme 1. Synthesis of N'-acetyl-N'-phenyl-2-naphthohydrazide (1). 3. Results and discussion The molecular structure containing the atomic labeling of the asymmetric unit of the crystal N'-acetyl-N'-phenyl-2- naphthohydrazide is shown in Figure 2 [26]. The X-ray diffraction analyses showed that the asymmetric unit of compound 1 contains two crystallographically independent molecules A and B. The molecule consists of a naphthalene ring and a benzene ring connected through a N'-acetylformo hydrazide bridge. In molecule B, the N'-methyl-N-phenylaceto hydrazide moiety is disordered over two sites with an occupancy ratio of 0.7531:0.2469. The geometric parameters, including bond distances and bond angles, show normal geometry [27] and are in close relation to the related structure N-(4-nitrobenzoyl)-N'- phenylhydrazine [28]. The length of the N-N single bond between nitrogen atoms is 1.388(2) Å in molecule A and the average value of 1.384 Å in molecule B; this is close to the respective bond length of 1.390(4) Å present in C13H11N3O3. Here, the N-N-C bond angles deviate slightly from the ideal value of 120° by 1.1°, which is due to the presence of substitu- tions of acetyl groups and carbonyl groups at its ends. In molecule A, the acetyl group is –sc to the hydrazine moiety as evident from the C11-N12-N13-C14 torsion angle value of - 90.0(3)°. The substituent carbonyl groups have an average value of C=O bond length of 1.217 Å, which is very close to its standard value (1.210 Å, [26]). Whereas, the N-N-C bond angle value of 118.7(3)°, the torsion angle value of N2-N1-C7-O7 of - 3.3(5)° signifies that carbonyl group is –sp to hydrazine moiety for molecule reported in literature [28]. In both title molecule 1 and the molecule of literature, nearly orthogonal values of torsion angle C-N-N-C signifies tendency of the lone-pair orbitals on nitrogen atoms to reduce the corresponding overlap and resonance integrals [28]. In the naphthalene ring systems, the endocyclic angles at C1, C3, C8 and C8’ are narrowed, while those at C2, C6, C26, C27, C29, C32’, C31’, C29’, C26’, C26’, C27’ and C24’ are expanded from 120°, respectively. This would appear to be a real effect caused by the fusion of the smaller benzene ring systems by which the strain is taken up by the angular distortion [29]. All the benzene rings are individually planar which is evident from smaller values of torsion angles. In molecule A, the benzene ring is twisted with respect to the naphthalene ring at a dihedral angle of 87.01(6)°. Some of the important bond lengths and bond angles are listed in Table 2. The dihedral angle value of 79.86(0)° shows that both the rings of the compound of the literature are also nearly orthogonal to each other [28]. Analysis of the crystal packing showed that there exists a network of N-H···O and C-H···O intermolecular hydrogen bonds. O38 acts as an acceptor atom for two types of hydrogen bonds, by interactions with N12 and C26 through H12 and H26 hydrogen atoms resulting in a relatively stronger C-H···O hydrogen bond. The hydrogen H35 on atom N35 of molecule B forms an intermolecular strong hydrogen bond with the carbonyl atom O15 of molecule A. In addition to this, there exists a wide array of C-H···π and π···π interactions for crystal structure stabilization and to form supramolecular structures. The alkyl-aromatic hydrogen bond connects the parent molecules to their centrosymmetrically related molecules. The 90° angle for stacking rings is observed for 1-1, 1-2, 1-4, 1-5, 2- 1, 2-4, 4-1, 4-2, 4-4, 4-5, 5-1, 5-4, and 6-7 molecular pairs. The geometry of these interactions is presented in Tables 3 and 4, respectively. Here CgI···CgJ represents the distance between the ring centroids; CgI···P represents the perpendicular distance of the centroid of one ring from the plane of the other; α is the dihedral angle between the planes of rings I and J; β is the angle between the normal to the centroid of ring I and the line joining ring centroids; Δ is the displacement of the centroid of rings J Sharma et al. / European Journal of Chemistry 13 (3) (2022) 253-258 255 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.3.253-258.2235 Table 2. Selected bond lengths and bond angles for non-hydrogen atoms (e.s.d.’s are given in parentheses) for compound 1. Atom Atom Length (Å) Atom Atom Length (Å) C1 C2 1.362(3) C29 C30 1.403(6) C1 C10 1.412(4) C30 C31 1.352(5) C1 C11 1.493(3) C31 C32 1.425(8) C2 C3 1.431(3) C32 C33 1.412(7) C3 C4 1.408(3) C34 O40 1.216(6) C3 C8 1.406(4) C34 N35 1.363(6) C4 C5 1.355(4) N35 N36 1.408(12) C5 C6 1.409(4) C24' C25' 1.331(15) C6 C7 1.341(4) C24' C33' 1.446(15) C7 C8 1.441(4) C24' C34' 1.45(3) C8 C9 1.392(4) C25' C26' 1.465(17) C9 C10 1.370(4) C26' C27' 1.374(15) C11 N12 1.364(3) C26' C31' 1.47(3) C11 O17 1.210(3) C27' C28' 1.354(15) C14 C16 1.488(3) C28' C29' 1.405(16) C14 N13 1.356(3) C29' C30' 1.346(17) C14 O15 1.223(3) C30' C31' 1.42(3) C18 C19 1.373(3) C31' C32' 1.36(3) C18 C23 1.375(3) C32' C33' 1.364(13) C18 N13 1.434(3) C34' O40' 1.210(16) C19 C20 1.385(3) C34' N35' 1.367(16) C20 C21 1.369(4) N35' N36 1.36(4) C21 C22 1.375(4) C37 C39 1.490(3) C22 C23 1.380(3) C37 N36 1.342(3) N12 N13 1.388(2) C37 O38 1.228(3) C24 C25 1.415(5) C41 C42 1.373(3) C24 C33 1.367(5) C41 C46 1.376(3) C24 C34 1.499(8) C41 N36 1.435(3) C25 C26 1.356(5) C42 C43 1.379(3) C26 C27 1.419(5) C43 C44 1.374(4) C27 C28 1.418(6) C44 C45 1.374(4) C27 C32 1.401(10) C45 C46 1.382(3) C28 C29 1.363(6) Atom Atom Atom Angle (°) Atom Atom Atom Angle (°) C2 C1 C10 118.9(2) C30 C31 C32 120.4(5) C2 C1 C11 117.6(2) C27 C32 C31 119.2(5) C10 C1 C11 123.4(2) C27 C32 C33 119.6(6) C1 C2 C3 121.3(2) C33 C32 C31 121.2(7) C4 C3 C2 121.1(2) C24 C33 C32 120.7(5) C8 C3 C2 118.4(2) O40 C34 C24 122.4(6) C8 C3 C4 120.5(2) O40 C34 N35 123.7(7) C5 C4 C3 120.3(3) N35 C34 C24 113.9(6) C4 C5 C6 120.0(3) C34 N35 N36 118.6(8) C7 C6 C5 121.3(3) C25' C24' C33' 121.6(12) C6 C7 C8 120.5(3) C25' C24' C34' 126.1(14) C3 C8 C7 117.4(3) C33' C24' C34' 112.2(13) C9 C8 C3 119.6(2) C24' C25' C26' 120.5(12) C9 C8 C7 123.0(3) C25' C26' C31' 116.4(13) C10 C9 C8 120.7(3) C27' C26' C25' 122.2(12) C9 C10 C1 121.0(2) C27' C26' C31' 121.4(15) N12 C11 C1 114.9(2) C28' C27' C26' 121.0(12) O17 C11 C1 123.6(2) C27' C28' C29' 118.8(12) O17 C11 N12 121.5(2) C30' C29' C28' 122.9(13) N13 C14 C16 117.3(2) C29' C30' C31' 121.0(17) O15 C14 C16 122.5(2) C30' C31' C26' 115(2) O15 C14 N13 120.2(2) C32' C31' C26' 120.0(18) C19 C18 C23 120.9(2) C32' C31' C30' 125(2) C19 C18 N13 118.8(2) C33' C32' C31' 122.4(14) C23 C18 N13 120.2(2) C32' C33' C24' 119.1(10) C18 C19 C20 119.1(2) O40' C34' C24' 128(2) C21 C20 C19 120.4(2) O40' C34' N35' 115(2) C20 C21 C22 120.0(2) N35' C34' C24' 117(2) C21 C22 C23 120.2(2) N36 N35' C34' 119(3) C18 C23 C22 119.4(2) N36 C37 C39 117.6(2) C11 N12 N13 119.10(19) O38 C37 C39 122.4(2) C14 N13 C18 122.75(19) O38 C37 N36 120.0(2) C14 N13 N12 120.06(18) C42 C41 C46 120.8(2) N12 N13 C18 116.81(18) C42 C41 N36 118.8(2) C25 C24 C34 122.8(4) C46 C41 N36 120.3(2) C33 C24 C25 119.8(4) C41 C42 C43 119.5(2) C33 C24 C34 117.3(5) C44 C43 C42 120.3(2) C26 C25 C24 120.2(4) C45 C44 C43 119.8(2) C25 C26 C27 121.2(4) C44 C45 C46 120.4(2) C28 C27 C26 122.1(4) C41 C46 C45 119.1(2) C32 C27 C26 118.5(4) N35 N36 C41 113.6(4) C32 C27 C28 119.4(4) N35' N36 C41 123.8(14) C29 C28 C27 119.4(4) C37 N36 N35 123.3(4) C28 C29 C30 121.5(4) C37 N36 N35' 112.5(13) C31 C30 C29 120.0(4) C37 N36 C41 123.11(19) 256 Sharma et al. / European Journal of Chemistry 13 (3) (2022) 253-258 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.3.253-258.2235 Table 3. Geometry of inter- and intra-molecular interactions for compound 1 *. D–H···A D–H, Å H···A, Å D···A, Å θ(D–H···A), deg N12-H12···O38 i 0.90(2) 1.92(2) 2.781(2) 159(2) N35-H35···O15 ii 0.90(2) 1.88(3) 2.747(11) 161(3) C26-H26···O38 i 0.93 2.59 3.490(4) 162 C6-H6···Cg8 iii 0.93 2.83 3.638(3) 146 C21-H21···Cg1 iv 0.93 2.76 3.617(3) 154 C29-H29···Cg3 v 0.93 2.75 3.528(5) 142 C39-H39A···Cg7 vi 0.93 2.84 3.531(3) 130 * Symmetry codes: (i) x, 1+y, z, (ii) x, y, z, (iii) –x, 2-y, 1-z, (iv) -1+x, y, z, (v) 1-x, 1-y, -z, (vi) 1-x, 1-y, 1-z. Cg1, Cg3, Cg7, and Cg8, and represents the center of gravity of the rings (C24A/C25A/C26A/C27A/C32A/C33A), (C41/C42/C43/C44/C45/C46), (C3/C4/C5/C6/C7/C8) and (C18/C19/C20/C21/ C22/C23), respectively. Table 4. Geometry of π-π interactions for compound 1 *. CgI CgJ CgI···CgJ, Å CgI···P, Å α, deg β, deg Δ, Å 1 1i 3.663 3.490 0.0 17.6 1.11 1 2i 3.692 3.490 2.3 19.0 1.20 1 4i 3.674 3.452 1.1 20.1 1.25 1 5i 3.636 3.457 1.1 20.1 1.13 2 1i 3.692 3.490 2.3 19.0 1.20 2 4i 3.794 3.428 1.9 24.4 1.64 4 1i 3.674 3.449 1.1 20.0 1.26 4 2i 3.794 3.455 1.9 25.4 1.56 4 4i 3.939 3.427 0.0 29.5 1.94 4 5i 3.507 3.426 1.4 13.6 0.74 5 1i 3.635 3.440 1.9 18.8 1.26 5 4i 3.507 3.409 1.4 12.3 0.81 6 7ii 3.7686 3.4249 1.70 26.1 1.55 * Symmetric codes: (i) 1-x, 1-y, -z, (ii) –x, 2-y, 1-z. Cg1, Cg2, Cg4, Cg5, Cg6 and Cg7 represent the center of gravity of the rings (C24A/C25A/C26A/ C32A/C33A), (C27A/C28A/C29A/C30A/C31A/C32A), (C24’/C25’/C26’/C31’/C32’/C33’), (C26’/C27’/C28’/C29’/C30’/C31’), (C1/C2/C3/C8/C9/C10) and (C3/C4/C5/C6/ C7/C8), respectively. Figure 2. The molecular structure of the compound 1. Figure 3. Packing view of molecules down to a and b-axis. Sharma et al. / European Journal of Chemistry 13 (3) (2022) 253-258 257 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.3.253-258.2235 relative to the intersection point of the normal to the centroid of ring I and the least-squares plane of ring J. These π···π contacts describe the interactions present between the naphthalene ring and the benzene ring of compound 1. The packing of the molecule within the unit cell viewed down the a and b-axis is shown in Figure 3. Molecules are packed together to form infinite layers along the (001) plane. Whereas the crystal packing arrangement for the related compound of the literature is linked to a complex three-dimensional framework structure by a combination of N-H···O, N-H···N, and C-H···O types of intermolecular H-bonds, resulting in sheet-like structure in dearth of other C-H···π and π···π contacts [28]. 4. Conclusions Single crystal X-ray diffraction studies led to unambiguous crystal structure determination of the compound which crystallizes into triclinic crystal system with space group P-1. Direct methods were used to solve the crystal structure and refined by full matrix least squares procedure to final R value of 0.0580. In molecule B, the moiety is disordered over two sites with an occupancy ratio of 0.7521:0.2469. A complete set of intermolecular hydrogen bonds; C-H···π and π···π interactions was observed and quantified for crystal packing analysis. Acknowledgements Vivek Kumar Gupta thanks University of Jammu, Jammu, India, for financial support under the Rashtriya Uchchatar Shiksha Abhiyan (RUSA) 2.0 Project. (Ref. No: RUSA/JU/2/2019-20/111/3588-3636). Bubun Banerjee thanks Akal University for financial assistance. Supporting information CCDC-2110780 contains the supplementary crystallographic 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. Ethical approval: All ethical guidelines have been adhered. Sample availability: Samples of the compound are available from the author. CRediT authorship contribution statement Conceptualization: Vivek Kumar Gupta, Goutam Brahmachari; Methodology: Varun Sharma, Indrajit Karmakar; Software: Varun Sharma, Indrajit Karmakar; Validation: Vivek Kumar Gupta, Goutam Brahmachari; Formal Analysis: Vivek Kumar Gupta, Goutam Brahmachari; Investigation: Indrajit Karmakar, Varun Sharma; Resources Vivek Kumar Gupta, Goutam Brahmachari; Data Curation: Varun Sharma, Indrajit Karmakar; Writing - Original Draft: Varun Sharma, Indrajit Karmakar; Writing - Review and Editing: Vivek Kumar Gupta, Goutam Brahmachari; Varun Sharma, Indrajit Karmakar; Visualization: Goutam Brahmachari, Vivek Kumar Gupta; Funding acquisition: none; Supervision: Vivek Kumar Gupta, Goutam Brahmachari. ORCID and Email Varun Sharma varunsharma5228@gmail.com https://orcid.org/0000-0003-2866-8638 Indrajit Karmakar ijk91.chem@gmail.com https://orcid.org/0000-0002-2713-8080 Goutam Brahmachari brahmg2001@yahoo.co.in https://orcid.org/0000-0001-9925-6281 Vivek Kumar Gupta vivek.gupta2k9@gmail.com https://orcid.org/0000-0003-2471-5943 References [1]. Ding, Y.; Li, H.; Meng, Y.; Zhang, T.; Li, J.; Chen, Q.-Y.; Zhu, C. Direct synthesis of hydrazones by visible light mediated aerobic oxidative cleavage of the C-C bond. Org. Chem. Front. 2017, 4, 1611–1614. [2]. Krátký, M.; Bősze, S.; Baranyai, Z.; Stolaříková, J.; Vinšová, J. Synthesis and biological evolution of hydrazones derived from 4- (trifluoromethyl)benzohydrazide. Bioorg. Med. Chem. Lett. 2017, 27, 5185–5189. [3]. Kauthale, S.; Tekale, S.; Damale, M.; Sangshetti, J.; Pawar, R. Synthesis, antioxidant, antifungal, molecular docking and ADMET studies of some thiazolyl hydrazones. Bioorg. Med. Chem. Lett. 2017, 27, 3891– 3896. [4]. 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Sharma, V.; Karmakar, I.; Brahmachari, G.; Gupta, V. K. Synthesis, spectroscopic characterization, crystal structure, theoretical (DFT) studies and molecular docking analysis of biologically potent isopropyl 5-chloro-2-hydroxy-3-oxo-2,3-dihydrobenzofuran-2-car boxylate. Mol. Cryst. Liq. Cryst. 2022, 1–22. Copyright © 2022 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at http://www.eurjchem.com/index.php/eurjchem/pages/view/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. 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. General 2.2. Crystal structure determination and refinement 3. Results and discussion 4. Conclusions Acknowledgements Supporting information Disclosure statement CRediT authorship contribution statement ORCID and Email References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField15: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: PrintField25: