X-ray crystal structure analysis of 5-bromospiro[indoline-3,7'-pyrano[3,2-C:5,6-C']dichromene]-2,6',8'-trione European Journal of Chemistry 12 (2) (2021) 187-191 European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2021 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.12.2.187-191.2086 European Journal of Chemistry View Journal Online View Article Online X-ray crystal structure analysis of 5-bromospiro[indoline-3,7'-pyrano[3,2-C:5,6-C']dichromene]-2,6',8'-trione Varun Sharma 1, Bubun Banerjee 2,3, Gurpreet Kaur 3 and Vivek Kumar Gupta 1,* 1 Department of Physics, University of Jammu, Jammu Tawi-180006, India varunsharma5228@gmail.com (V.S.), vivek.gupta2k9@gmail.com (V.K.G.) 2 Department of Chemistry, Akal University, Talwandi Sabo, Bathinda, Punjab-151302, India banerjeebubun@gmail.com (B.B) 3 Department of Chemistry, Indus International University, V.P.O Bathu, Distt. Una, Himachal Praesh- 174301, India kaur80328@gmail.com (G.K.) * 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.12.2.187-191.2086 Received: 27 January 2021 Received in revised form: 27 February 2021 Accepted: 07 March 2021 Published online: 30 June 2021 Printed: 30 June 2021 An analog of spirooxindole[pyrano-bis-2H-l-benzopyran] derivatives namely 5-bromospiro [indoline-3,7'-pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione was synthesized via one-pot pseudo three-component reaction of one equivalent of 5-bromoisatin and two equivalents of 4-hydroxycoumarin using mandelic acid as a naturally occurring organo catalyst in aqueous ethanol under reflux conditions. The synthesized compound was characterized by FT-IR, 1H NMR, 13C NMR, and HRMS data. Crystal structure was determined by using single X-ray crystallography technique. It was found that the crystals are triclinic with space group P-1, C108H60Br4N4O29S2: a = 11.8333(6) Å, b = 12.8151(6) Å, c = 17.1798(8) Å, α = 77.317(4)°, β = 74.147(4)°, γ = 66.493(5)°, V = 2280.0(2) Å3, Z = 1, T = 149.99(10) K, μ(MoKα) = 1.902 mm-1, Dcalc = 1.647 g/cm3, 11545 reflections measured (3.836° ≤ 2Θ ≤ 50.998°), 8310 unique (Rint = 0.0488, Rsigma = 0.0875) which were used in all calculations. The final R1 was 0.0622 (I > 2σ(I)) and wR2 was 0.1994 (all data). The crystal structure was solved by direct methods and refined by full-matrix least-squares procedure to a final R-value of 0.0622 for 6264 observed reflections. The crystal structure was stabilized by an elaborate system of N- H···O, O-H···O, C-H···π, and π···π interactions involving solvent molecules to form supramolecular structure. Benzopyran Spirooxindoles Direct methods Solvent molecules Hydrogen bonding X-ray crystallography Cite this: Eur. J. Chem. 2021, 12(2), 187-191 Journal website: www.eurjchem.com 1. Introduction Heterocyclic skeletons are very common in naturally occurring bioactive compounds as well as in commercially available drug molecules [1-3]. Spiro-oxindoles and 4-hydroxy- coumarin both moieties are very common in naturally occurring bioactive compounds [4,5]. Various synthetic benzopyran derivatives are found to possess a wide range of biological activities [6-8]. Recently, in 2016, Parthasarathy et al. [9] showed that spirooxindole[pyrano-bis-2H-l-benzopyran] derivatives can be used as an antimicrobial agent. On the other hand, mandelic acid is an inexpensive, commercially available, environmentally benign, naturally occurring organo-catalyst. In recent past, our group, for the first time, has investigated the catalytic activities of mandelic acid for various reactions [10- 11]. The title compound, i.e., 5-bromospiro[indoline-3,7'- pyrano[3,2-c:5,6-c']dichromene]-2,6',8'-trione (I) was also synthesized with 69% yield by using 20 mol% mandelic acid as catalyst from the one-pot pseudo three-component reaction of one equivalent of 5-bromoisatin and two equivalents of 4- hydroxycoumarin in aqueous ethanol under reflux conditions at 110 °C. The biological significance of these heterocycles prompted us to synthesize this molecule. We were also able to form single crystals of the title compound. In this commu- nication we wish to report the mandelic acid catalyzed a novel synthetic method and crystal structure of the title compound I. 2. Experimental 2.1. Synthesis To an oven-dried screw cap round bottom flask, a magnetic stir bar, 5-bromoisatin (0.225 g, 1 mmol) and 4-hydroxy- coumarin (0.324 g, 2 mmol), mandelic acid (0.031 g, 20 mol % as an organo-catalyst) and 5 mL aqueous ethanol [EtOH:H2O (1:1, v:v)] were added in a sequential manner. The reaction mixture was then refluxed for four hours at 110 °C. In between, the progress of the reaction was monitored by TLC. The reaction mixture was then allowed to cool. At room tempera- ture, a solid mass precipitated out that was filtered off followed by subsequent washing with aqueous ethanol. Crude product was further purified by column chromatography. ABSTRACT RESEARCH ARTICLE KEYWORDS https://dx.doi.org/10.5155/eurjchem.12.2.187-191.2086 https://www.eurjchem.com/ https://dx.doi.org/10.5155/eurjchem.12.2.187-191.2086 mailto:varunsharma5228@gmail.com mailto:vivek.gupta2k9@gmail.com mailto:banerjeebubun@gmail.com mailto:kaur80328@gmail.com mailto:vivek.gupta2k9@gmail.com http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.12.2.187-191.2086&domain=pdf&date_stamp=2021-06-30 188 Sharma et al. / European Journal of Chemistry 12 (2) (2021) 187-191 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.2.187-191.2086 Table 1. Crystallographic characteristics, details of X-ray data collection and structure refinement parameters for compound I. Empirical formula C108H60Br4N4O29S2 Formula weight 2261.36 Temperature(K) 149.99(10) Crystal system Triclinic Space group P-1 a (Å) 11.8333(6) b (Å) 12.8151(6) c (Å) 17.1798(8) α (°) 77.317(4) β (°) 74.147(4) γ (°) 66.493(5) Volume(Å3) 2280.0(2) Z 1 ρcalc (g/cm3) 1.647 μ/mm-1 1.902 F(000) 1140.0 Crystal size (mm3) 0.3 × 0.2 × 0.2 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 3.836 to 50.998 Index ranges -14 ≤ h ≤ 12, -15 ≤ k ≤ 14, -20 ≤ l ≤ 18 Reflections collected 11545 Independent reflections 8310 [Rint = 0.0488, Rsigma = 0.0875] Data/restraints/parameters 8310/217/734 Goodness-of-fit on F2 1.044 Final R indexes [I≥2σ (I)] R1 = 0.0622, wR2 = 0.1671 Final R indexes [all data] R1 = 0.0906, wR2 = 0.1994 Largest diff. peak/hole (e Å-3) 0.87/-0.95 Figure 1. The structure of compound I, displacement ellipsoids are drawn at 40% probability level. Single crystal was obtained from ethanol as solvent. For crystallization, 0.025 g of the purified compound was dissolved in 3 mL DMSO and left at room temperature. Orange block shaped crystals were obtained after few days. 5-Bromospiro[indoline-3, 7'-pyrano[3, 2-c:5, 6-c']dechro mene]-2,6',8'-trione (I): Color: Brownish. Yield: 69%. M.p.: 190- 191 °C. FT-IR (KBr, ν, cm-1): 3389 (NH), 1709 (C=O) (ester), 1656(C=O) (ester), 1618 (C=O) (amide). 1H NMR (400 MHz, DMSO-d6, δ, ppm): 11.02 (brs, 1H, -NH), 8.42 (d, 2H, J = 8.4 Hz, Ar-H), 7.81-7.89 (m, 2H, Ar-H), 7.55-7.61 (m, 3H, Ar-H), 7.49 (d, 2H, J = 8.4 Hz, Ar-H),7.38 (d, 1H, J = 8.4 Hz, Ar-H), 6.79(d, 1H, J = 7.4 Hz, Ar-H). 13C NMR (100 MHz, DMSO-d6, δ, ppm): 176.12, 156.17, 156.06, 153.89, 152.08, 143.54, 134.04, 131.73, 127.36, 124.97, 123.74, 116.57, 113.12, 113.03, 110.74, 103.09, 46.52. HRMS (ESI-TOF, m/z) calcd. for C26H12BrNO6, 512.9848; found 512.9826. 2.2. Crystal structure determination and refinement The molecular structure solution was obtained by direct method procedure as using SHELXT [12]. The structure was solved by direct methods. Six cycles of full-matrix least-squares refinement was carried out and it brought the final R-factor to 0.0622. All non-hydrogen atoms of the molecule were located in the best E-map and refined in anisotropic approximation using SHELXS [12]. The Crystallographic data are summarized in Table 1. All hydrogen atoms were geometrically fixed and a riding model was used for them (N-H = 0.86, C-H = 0.93-0.98 Å), Uiso(H) = 1.5Ueq for the attached C atoms of methyl groups and 1.2Ueq(N,C) for other H atoms except for H2, H1 and H1’ atoms attached to N2, N1 and N1’ of pyrrole group in molecule. They were localized from the difference Fourier map, and their parameters were refined in the isotropic approximation of atomic displacements. The geometry of the molecule was calculated using the WinGX [13], PARST [14], and PLATON [15] programs. 3. Results and discussion The molecular structure containing atomic labeling of the asymmetric unit of crystals (I), ‘4(C26H12BrNO6), 2(C2H6OS), 3(O)’ is shown in Figure 1 (ORTEP program) [16] and the packing diagram as generated using PLATON [15] is shown in Figure 2. Sharma et al. / European Journal of Chemistry 12 (2) (2021) 187-191 189 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.2.187-191.2086 Table 2. Selected bond lengths and angles for compound I. Bond d, Å Bond d, Å C1-O3 1.375(6) C35-O36 1.372(7) C3-O3 1.383(7) C37-O36 1.379(6) C3-O31 1.205(7) C37-O65 1.213(7) C7-O32 1.218(7) C41-O66 1.210(6) C7-O8 1.380(6) C41-O42 1.359(6) C9-O8 1.381(7) C43-O42 1.383(6) C15-O16 1.366(6) C49-O50 1.367(6) C17-O16 1.364(6) C51-O50 1.353(7) C25-Br1 1.900(6) C59-Br2 1.884(6) C28-N1' 1.402(10) C62-N2 1.384(7) C28-N1 1.410(16) N2-C64 1.361(7) N1-C30 1.344(16) C64-O67 1.203(7) N1'-C30 1.347(10) C30-O33 1.218(6) Angle ∠, deg Angle ∠, deg C1-O3-C3 121.9(4) C35-O36-C37 122.2(4) C7-O8-C9 122.5(4) C41-O42-C43 122.2(4) C17-O16-C15 118.0(4) C51-O50-C49 117.5(4) C4-C5-C6 108.7(4) C38-C39-C40 107.6(4) C23-C5-C30 100.8(4) C57-C39-C64 101.6(4) Figure 2. View of molecules packing down the a-axis in the unit cell (I). The asymmetric unit consists of two molecules of the title compound I, one molecule of solvent DMSO and 1.5 molecules of partial water who’s H-atoms could not be located. Molecules A and B of the compound are built up from a fused pyrrole and pyran ring system through a spiro junction at common carbon atoms C5 and C39, respectively. The nitrogen atom of molecule I is disordered over two sites with an occupancy ratio of N1:N1’ = 0.296:0.703. All the atoms of DMSO solvent molecule and partial oxygen atoms are refined to site of occupancy of 0.5000. The structural parameters, including bond distances and angles show a normal geometry, and are close to their normal geometry [17] and show a fair amount of agreement with those observed in the related molecule (C26H12FNO6) [8]. For central pyran skeleton of the molecule A, bond distances are O16-C17 = 1.364(6) Å, O16-C15 = 1.366(6) Å and bond angle C15-O16-C17= 118.0(4)°. For the molecule B, O50- C49 = 1.367(6) Å, O50-C51 = 1.353(7) Å and bond angle C52- O50-C49 =117.5(4)° are quite similar to related structure (1.3712 (16) Å, 1.3685 (16) Å, 117.29 (10)°). For hetero O atom of chromene rings attached adjacent to central pyran ring for molecule A and B, the bond distances and bond angles vary from 1.359(6) to 1.383(6) Å and 121.9(4) to 122.5(4)° indicating hetero π-electron delocalization over carbonyl groups attached to these rings. Whereas the C=O bond lengths vary from 1.203(7) to 1.218(7) Å, which are very close to the standard value for carbonyl group (1.210 Å; [10]). The N1-C28, N1’-C28, N2-C62; and N1-C30, N1’-C30, N2-C64 bond lengths (1.410(16), 1.402(10), 1.384(7) Å; and 1.344(16), 1.347(10), 1.361(7) Å, respectively) differ from the corresponding mean values of 1.419 and 1.331 Å, respectively, as reported for γ-lactams [10], which may reflect the delocalization of electrons in this ring. Moreover, around C5 and C39 in pyrrole ring, C23-C5-C30 and C57-C39-C64 (100.8(4)°, 101.6(4)°) deviate significantly from the ideal tetrahedral value of 109.4°. Whereas in pyran ring, the angles (C4-C5-C6= 108.7(4)°, C40-C39-C38 = 107.6(4)°) differ from similar angle of 101.17(10)° of the related structure. The Bromine atom substituted at C25 and C59 are at 1.900(6) Å, 1.884(6) Å of bond lengths, respectively. In 1H NMR, all the hydrogen atoms expected NH are appeared in the aromatic region. In the benzene rings of the oxindole ring system, the endocyclic angles at C24, C27, C58, and C61 are narrowed while those at C23, C25, C28, C60 and C62 are expanded from 120° respectively. This would appear to be a real effect caused by the fusion of the smaller pyrrole ring to the six-membered benzene ring and the strain is taken up by the angular distortion rather than by bond-length distortions. All rings of molecules A and B show planar conformation. The dihedral angle of 87.52(8)° shows that the oxindole ring is almost perpendicular to the fused pyrano-bis-2H-l-benzopyran moiety in molecule B. Table 2. contains the selected bond lengths and angles for compound I. The crystal structure is assembled from the title molecules with solvent molecules via hydrogen bonding. Hydrogen bonded interactions between the title molecule and solvent molecules are also observed. Analysis of the crystal packing showed that there exist N-H···O and O-H···O types of intra- and inter-molecular hydrogen bonds. 190 Sharma et al. / European Journal of Chemistry 12 (2) (2021) 187-191 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.2.187-191.2086 Table 3. Geometry of intermolecular and intramolecular interactions for compound I *. D–H···A D–H, Å H···A, Å D···A, Å ∠(D–H···A), deg N1’-H1’···O1’i 0.84(4) 2.14(5) 2.8400(2) 140(6) N1’-H1’···O1ii 0.84(4) 2.01(5) 2.8017(2) 155(6) N2-H2···O2 0.84(2) 2.11(3) 2.879(10) 152(5) N2-H2···O2’ 0.84(2) 2.18(3) 2.902(10) 143(3) C67-H67B···S1 0.96 2.22 2.8378 121 C10-H10···Cg8ii 0.96 2.75 3.5973 152 C27-H27···Cg14iii 0.96 2.80 3.3689 120 C44-H44···Cg15iv 0.96 2.72 3.5742 153 C60-H60···Cg3 0.96 2.75 3.6349 159 * Symmetry codes: (i) x, 1+y, z; (ii) 1-x, 1-y, 1-z; (iii) 1-x, 1-y, -z; (iv) 1-x, -y, 1-z; Cg3, Cg8, Cg14, and Cg15 present the center of gravity of the rings (O3/C1/C18/C17/C4/C3), (C23/C24/C25/C26/C27/C28), (C43/C44/C45/C46/C47/C48) and (C57/C58/C59/C60/C61/C62), respectively. Table 4. Geometry of π···π interactions for (I) CgI CgJ CgI···CgJ, Å CgI···P, Å α, deg β, deg Δ, Å 1 3i 3.8192 0.0345 89 51.9 3.80 1 4i 3.8149 0.0342 88 49.6 3.81 2 3i 3.7887 0.0336 89 49.1 3.79 2 4i 3.8434 0.0330 89 52.4 3.84 3 7ii 3.7242 3.3292 3 45.6 1.67 4 6ii 3.4942 3.3746 1 15.0 0.27 6 4ii 3.4942 3.3746 1 14.8 0.91 6 7ii 3.6797 3.3238 3 25.4 1.58 7 3ii 3.7242 3.2980 3 27.7 1.63 7 6ii 3.6797 3.3927 3 22.8 1.42 9 10i 3.7945 0.0080 89 50.6 3.79 9 11i 3.8314 0.0021 87 51.0 3.38 10 14iii 3.8139 3.4404 3 26.8 1.65 11 13iii 3.5908 3.3487 6 20.0 1.29 13 14iii 3.5890 3.3815 4 18.4 1.20 14 10iii 3.8139 3.4035 3 25.6 1.72 14 13iii 3.5890 3.4049 4 19.6 1.13 Symmetric codes:(i) x, y, z; (ii) -x, 1-y, 1-z; (iii) 2-x, -y, -z. In addition, the molecular packing is also stabilized with the help of weak π···π, C-H···π, and Van der Waal’s forces. The geometry of these interactions is presented in Tables 3 and 4, respectively. The 90° angle for stacking rings is observed for 1- 3, 1-4, 2-3, 2-4, 9-10, and 9-11 molecular pairs probably indicates that the stacking is missing. The molecular packing in the unit cell is shown in Figure 2. Cg1, Cg2, Cg3, Cg4, Cg6, Cg7, Cg9, Cg10, Cg11, Cg13 and Cg14 represent the center of gravity of the rings (N1’/C28/ C23/C5/C30), (C5/C23/C28/N1/C30), (C1/C18/C17/C4/C3), (C7/C6/C15/C14/C9), (C1/C18/C19/C20/C21/C22), (C10/ C11/C12/C13/C14), (C62/C57/C39/C64), (O36/C35/C51/ C38/C37), (O42/C41/C40/C49/C48/C43), (C35/C52/C53/ C54/C55/C56) and (C44/C45/C46/C47/C48), respectively. 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 relative to the intersection point of the normal to the centroid of ring I and the least- squares plane of ring J. The small values of torsion angle of compound I indicates that the bicyclic indole ring systems, along with central pyran ring systems are planar in conformation. Whereas the central pyran ring in the related molecule (C26H12FNO6) [9] adopts a boat conformation. 4. Conclusion A spiro-oxindoles fused pyrano-bis-2H-l-benzopyran deri- vative was synthesized due to the recognition that molecules comprised of two or more heterocyclic skeleton often possess heightened pharmacological activities, in this regard a detailed spectral and X-ray crystallographic behavioral study was carried out. The crystal structure was solved by direct methods and refined by full-matrix least-squares procedure. The struc- tural parameters, including bond distances are close to their normal geometry. Different hydrogen bond modes and π···π interactions involving solvent molecules played an incomparable role in the stabilization and formation of supramolecular crystal structure. Acknowledgements Vivek Kumar Gupta is thankful to University of Jammu, Jammu, India, for financial support under Rashtriya Uchchatar Shiksha Abhiyan (RUSA) 2.0 Project. (Ref. No: RUSA/JU/ 2/2019-20/111/3588-3636). Supporting information CCDC-2008867 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 interests: 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. ORCID Varun Sharma https://orcid.org/0000-0003-2866-8638 Bubun Banerjee https://orcid.org/0000-0001-7119-9377 Gurpreet Kaur https://orcid.org/0000-0002-9685-7927 Vivek Kumar Gupta https://orcid.org/0000-0003-2471-5943 https://www.ccdc.cam.ac.uk/structures/ mailto:data_request@ccdc.cam.ac.uk https://orcid.org/0000-0003-2866-8638 https://orcid.org/0000-0001-7119-9377 https://orcid.org/0000-0002-9685-7927 https://orcid.org/0000-0003-2471-5943 Sharma et al. / European Journal of Chemistry 12 (2) (2021) 187-191 191 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.2.187-191.2086 References [1]. Banerjee, B. Chem. Select 2017, 2 (23), 6744–6757. [2]. Banerjee, B.; Kaur, G.; Kaur, N. Curr. Org. Chem. 2021, 25 (1), 209– 222. [3]. Banik, B. K.; Banerjee, B.; Kaur, G.; Saroch, S.; Kumar, R. Molecules 2020, 25 (24), 5918–5918. [4]. Banerjee, B.; Kaur, G. Curr. Microw. Chem. 2020, 7 (1), 5–22. [5]. Kaur, G.; Bala, K.; Devi, S.; Banerjee, B. Curr. Green Chem. 2018, 5 (3), 150–167. [6]. Almansour, A. I.; Kumar, R. S.; Arumugam, N.; Kanagalaksmi, S.; Suresh, J. Acta Crystallogr. Sect. E Struct. Rep. Online 2012, 68 (4), o1172–o1172. [7]. Almansour, A. I.; Kumar, R. S.; Arumugam, N.; Vishnupriya, R.; Suresh, J. Acta Crystallogr. Sect. E Struct. Rep. Online 2012, 68 (4), o1194– o1194. [8]. Almansour, A. I.; Kumar, R. S.; Arumugam, N.; Devi Shree, P.; Suresh, J. Acta Crystallogr. Sect. E Struct. Rep. Online 2012, 68 (3), o744–o744. [9]. Parthasarathy, K.; Praveen, C.; Saranraj, K.; Balachandran, C.; Kumar, P. S. Med. Chem. Res. 2016, 25 (10), 2155–2170. [10]. Kaur, G.; Singh, A.; Bala, K.; Devi, M.; Kumari, A.; Devi, S.; Devi, R.; Gupta, V. K.; Banerjee, B. Curr. Org. Chem. 2019, 23 (16), 1778–1788. [11]. Kaur, G.; Shamim, M.; Bhardwaj, V.; Gupta, V. K.; Banerjee, B. Synth. Commun. 2020, 50 (10), 1545–1560. [12]. Sheldrick, G. M. Acta Crystallogr. A Found. Adv.2015, 71, 3–8. [13]. Farrugia, L. J. J. Appl. Crystallogr.1997, 30 (5), 565–565. [14]. Nardelli, M. J. Appl. Crystallogr.1995, 28 (5), 659–659. [15]. Spek, A. L. Acta Crystallogr. D Biol. Crystallogr. 2009, 65, 148–155. [16]. Farrugia, L. J. J. Appl. Crystallogr.2012, 45 (4), 849–854. [17]. Allen, F. H.; Kennard, O.; Watson, D. G.; Brammer, L.; Orpen, A. G.; Taylor, R. J. Chem. Soc., Perkin Trans. 2 1987, 12, S1-S19. Copyright © 2021 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. Synthesis 2.2. Crystal structure determination and refinement 3. Results and discussion 4. Conclusion Acknowledgements Supporting information Disclosure statement ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: