Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of N,N'-bis(3-quinolyl-methylene)diphenylethanedione dihydrazone European Journal of Chemistry 12 (4) (2021) 394-400 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.12.4.394-400.2153 European Journal of Chemistry View Journal Online View Article Online Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of N,N'-bis(3-quinolyl-methylene)diphenylethanedione dihydrazone Goutam Kumar Patra 1,*, Amit Kumar Manna 1 and Dinesh De 2 1 Department of Chemistry, Faculty of Physical Sciences, Guru Ghasidas Vishwavidyalaya, Bilaspur (Chhattisgarh), 495009, India goutam.patra@ggu.ac.in (G.K.P.), amitmanna51@gmail.com (A.K.M.) 2 Department of Basic Science, Vishwavidyalaya Engineering College, Lakhanpur, CSVTU- Bhilai, Chhattisgarh-497116, India d2chem@gmail.com (D.D.) * Corresponding author at: Department of Chemistry, Faculty of Physical Sciences, Guru Ghasidas Vishwavidyalaya, Bilaspur (Chhattisgarh), 495009, India. e-mail: goutam.patra@ggu.ac.in (G.K. Patra). 10.5155/eurjchem.12.4.394-400.2153 Received: 16 July 2021 Received in revised form: 20 August 2021 Accepted: 28 August 2021 Published online: 31 December 2021 Printed: 31 December 2021 The synthesis, characterization, and theoretical studies of a novel hydrazine, N,N’-bis-(3- quinolylmethylene)diphenylethanedione dihydrazone (1) has been reported. The molecular structure has been characterized by room-temperature single-crystal X-ray diffraction which reveals that two quinoline moieties are disposed nearly perpendicularly around the central C-C bond giving a ‘L’ shape of the molecule. This particular geometry gives rise to the hydrogen-bonded supramolecular rectangle of two self-complementary molecules. These supramolecular units are further assembled by π-π interaction. The Hirshfeld surface analysis of compound 1 shows that C···C, C···H, H···H, and N···H interactions of 13.1, 9.9, 52.3, and 7.4%, respectively, which exposed that the main intermolecular interactions were H···H intermolecular interactions. Crystal data for C34H24N6: Triclinic, space group P-1 (no. 2), a = 10.885(3) Å, b = 11.134(3) Å, c = 12.870(3) Å, α = 90.122(6)°, β = 114.141(6)°, γ = 110.277(5)°, V = 1316.1(6) Å3, Z = 2, T = 100(2) K, μ(MoKα) = 0.080 mm-1, Dcalc = 1.304 g/cm3, 7309 reflections measured (3.518° ≤ 2Θ ≤ 39.276°), 2318 unique (Rint = 0.0527, Rsigma = 0.0565) which were used in all calculations. The final R1 was 0.0416 (I > 2σ(I)) and wR2 was 0.1074 (all data). Dihydrazone Di-Schiff base Diphenylethanedione X-ray crystal structure Hirshfeld surface analysis Density functional theory (DFT) Cite this: Eur. J. Chem. 2021, 12(4), 394-400 Journal website: www.eurjchem.com 1. Introduction Generally, Schiff bases provide suitable geometrical and electronic environments towards some selected main metal ions, thus responsible for stable host-guest interaction. The specific ion selectivity depends on the relative stability of the host-guest interaction, thus can be influenced by the cavity size, flexibility of the chelator, and hardness of the coordinating atom; whereas the optical response is due to influence of guest on the electronic environment of the chromo-fluorophore [1-6]. As the guest selective binding does not always produce a proper signal, thus tailor-made synthesis of a chemoreceptor with desired functionalities is necessary to achieve measurable signal through a change in emission and/or absorption upon coordination. After Jean-Marie Lehn’s famous report of supra- molecular chemistry [7], the chemistry of molecular assemblies and intermolecular noncovalent binding interactions, i.e. hydrogen bonding, ionic interactions and π-π stacking interactions have fascinated increasing attention in crystal engineering. In particular, hydrogen bonding π-π stacking interactions which is a powerful organizing force in designing various supramolecular and solid-state architectures [8-10], is extensively used not only for networking numerous organic and organometallic compounds [11,12], but also for generating interesting supramolecular properties, such as electrical, optical and magnetic [13,14] properties. Quinoline groups, with effective sites for coordination to transition metal ions, have been used for the construction of supramolecular coordination compounds [15-18]. In addition, organic imino-quinolyl fragments have proved to be very useful in self-assembly through hydrogen bonding and π-π stacking, and the assembled products have relevance to biological systems [19]. Thus, imino-quinolyl ligand like N,N’-bis-(3-quinolylmethylene) diphenylethanedione dihydrazone has been designed and synthesized. Density functional theory (DFT) is a quantum mechanical (QM) method used in chemistry and physics to calculate the electronic structure of atoms, molecules and solids. It has been very popular in computational solid-state physics since the 1970s. In recent years, density functional theory has been a shooting star in theoretical modelling [20,21]. The development of better exchange-correlation functional made it possible to calculate many molecular properties with comparable accuracies to traditional correlated ab initio methods, with more favorable computational costs [22]. ABSTRACT RESEARCH ARTICLE KEYWORDS https://dx.doi.org/10.5155/eurjchem.12.4.394-400.2153 https://www.eurjchem.com/ https://dx.doi.org/10.5155/eurjchem.12.4.394-400.2153 mailto:goutam.patra@ggu.ac.in mailto:amitmanna51@gmail.com mailto:d2chem@gmail.com mailto:goutam.patra@ggu.ac.in http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.12.4.394-400.2153&domain=pdf&date_stamp=2021-12-31 Patra et al. / European Journal of Chemistry 12 (4) (2021) 394-400 395 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.394-400.2153 Table 1. Crystal data and Refinement parameters of compound 1. Empirical formula C34H24N6 Formula weight 516.59 Temperature (K) 100(2) Crystal system Triclinic Space group P-1 a (Å) 10.885(3) b (Å) 11.134(3) c (Å) 12.870(3) α (°) 90.122(6) β (°) 114.141(6) γ (°) 110.277(5) Volume (Å3) 1316.1(6) Z 2 ρcalc (g/cm3) 1.304 μ (mm-1) 0.080 F(000) 540.0 Crystal size (mm3) 0.24 × 0.20 × 0.19 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 3.518 to 39.276 Index ranges -10 ≤ h ≤ 10, -10 ≤ k ≤ 10, -12 ≤ l ≤ 12 Reflections collected 7309 Independent reflections 2318 [Rint = 0.0527, Rsigma = 0.0565] Data/restraints/parameters 2318/0/457 Goodness-of-fit on F2 1.000 Final R indexes [I≥2σ (I)] R1 = 0.0416, wR2 = 0.0904 Final R indexes [all data] R1 = 0.0747, wR2 = 0.1074 Largest diff. peak/hole (e Å-3) 0.14/-0.20 N NN N N N Scheme 1. Chemical structure of compound 1. Literature survey revealed that the DFT has a great accuracy in reproducing the experimental values in terms of geometry, dipole moment, vibrational frequency, etc. [23]. Hirshfeld surface-based tools appear as a novel approach to this end [24,25]. 2. Experimental 2.1. Materials and physical measurements All chemicals used in this study were purchased from Aldrich Chemical Company, USA, and Acros Chemical Company, USA, and used without further purification unless otherwise mentioned. The melting point was determined by an electro- thermal IA9000 series digital melting point apparatus and is uncorrected. Microanalyses were carried out using a Perkin- Elmer 2400II elemental analyzer. Infrared (IR) spectra and solution electronic spectra were recorded on Nicolet Magna IR (Series II) and Shimadzu UV-160A spectrophotometers, respectively. 1H NMR spectra and electro-spray ionization mass (ESI-MS) measurements were made using a Bruker Advance 400 MHz and Finnigan LCQ Decaxp MAX mass spectrometer, respectively. 2.2. Synthesis of compound 1 Diphenylethanedione dihydrazone (0.714 g, 3 mmol) was dissolved in anhydrous methanol (25 mL) and in the solution 3- quinoline carboxaldehyde (0.942 g, 6 mmol) was added. The reaction mixture was refluxed under dry atmosphere for about 6 h. Then it was slowly cooled to room temperature to obtain a yellow crystalline solid of compound 1. The structure of the compound 1 has been confirmed by, mass spectrometry, 1H and 13C NMR, IR and electronic spectroscopy. N,N’-bis-(3-quinolylmethylene)diphenylethanedione dihyd- razone (1) (Scheme 1): Color: Yellow. Yield: 80%. M.p.: 473 K. FT-IR (KBr, cm-1): 3421 (wb), 3059 (w), 1612 (vs), 1569 (m), 1492 (m), 1448 (w), 1361 (w), 1315 (m), 1247 (m), 1172 (s), 968 (m), 785 (vs), 750 (s), 685 (vs), 464 (m). 1H NMR (400 MHz, CDCl3, δ, ppm): 9.16 (d, 2H, Ar-H), 8.67 (s, 2H, Ar-H), 8.27 (s, 2H, Ar-H), 8.16 (d, 2H, Ar-H), 7.92(d, 4H, Ar-H), 7.80 (s, 2H, -CH=N), 7.75 (t, 2H, Ar-H), 7.56 (t, 2H, Ar-H), 7.47 (m, 6H, Ar-H), 7.67 (t, 2H, Ar-H), 7.22-7.27 (m, 2H, Ar-H), 3.60 (t, 4H, -CH2), 1.66 (q, 4H, -CH2). 13C NMR (200 MHz, CDCl3, δ, ppm): 166.53, 157.40, 148.58, 137.95, 134.03, 131.57, 131.51, 129.07, 128.64, 128.58, 128.03, 127.90, 127.69, 127.48. MS (EI, m/z (%)): 517.339 (LH+, 100). Anal. calcd. for C34H24N6: C, 79.05; H, 4.68; N, 16.27. Found: C, 79.12; H, 4.59; N, 16.36%. 2.3. X-ray crystallography X-ray single crystal data were collected using MoKα (λ = 0.7107 Å) radiation on a Bruker APEX II diffractometer equip- ped with CCD area detector. Data collection, data reduction, structure solution/refinement were carried out using the software package of SMART APEX [26]. The structures were solved by direct methods SHELXS-97 [27] and standard Fourier techniques, and refined on F2 using full matrix least squares procedures SHELXL-97 using the SHELX-97 package incorpo- rated in WinGX [28]. Whenever possible, the hydrogen atoms were located on a difference Fourier map and refined. In other cases, the hydrogen atoms were geometrically fixed. The crystallographic details of compound 1 are summarized in Table 1, selected bond lengths and angles of 1 is listed in Tables 2 and 3 and selected hydrogen bonding parameters of compound 1 is shown in Table 4. 396 Patra et al. / European Journal of Chemistry 12 (4) (2021) 394-400 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.394-400.2153 Table 2. Bond distances for compound 1. Atom Atom Length (Å) Atom Atom Length (Å) C2 C3 1.363(5) C14 C22 1.451(5) C2 C1 1.424(5) C16 C17 1.412(5) C2 C10 1.446(5) C16 C15 1.414(5) C3 C4 1.417(5) C16 C21 1.416(5) C4 C5 1.418(5) C17 C18 1.411(5) C4 C9 1.418(5) C20 C21 1.368(5) C5 C6 1.360(6) C20 C19 1.395(6) C7 C8 1.361(6) C18 C19 1.364(6) C7 C6 1.393(6) C22 N5 1.276(4) C8 C9 1.394(5) N6 N5 1.410(4) C1 N1 1.323(5) N6 C34 1.291(4) C9 N1 1.380(5) C23 C24 1.392(5) C10 N2 1.284(4) C23 C28 1.383(5) N2 N3 1.422(4) C23 C34 1.486(5) N3 C11 1.290(4) C24 C25 1.389(6) C12 C11 1.473(5) C28 C27 1.382(6) C12 C29 1.379(5) C27 C26 1.369(6) C12 C33 1.393(5) C26 C25 1.371(6) C11 C34 1.510(5) C29 C30 1.379(5) N4 C17 1.374(5) C33 C32 1.384(5) N4 C13 1.325(5) C31 C32 1.375(5) C14 C13 1.412(5) C31 C30 1.367(5) Table 3. Bond angles for compound 1. Atom Atom Atom Angle (°) Atom Atom Atom Angle (°) C3 C2 C1 117.6(4) C17 C16 C21 118.9(4) C3 C2 C10 120.6(4) C15 C16 C21 123.1(4) C1 C2 C10 121.8(4) N4 C17 C16 122.8(4) C2 C3 C4 120.8(4) N4 C17 C18 117.9(4) C3 C4 C5 123.4(4) C16 C17 C18 119.3(4) C3 C4 C9 117.4(4) N4 C13 C14 125.1(4) C5 C4 C9 119.2(4) C14 C15 C16 119.6(4) C6 C5 C4 120.0(5) C21 C20 C19 121.0(5) C8 C7 C6 121.6(5) C20 C21 C16 120.0(5) C7 C8 C9 120.0(5) C19 C18 C17 120.4(5) N1 C1 C2 124.3(4) C18 C19 C20 120.3(5) C5 C6 C7 120.0(5) N5 C22 C14 121.3(4) C8 C9 C4 119.1(4) C34 N6 N5 111.3(3) N1 C9 C4 122.0(4) C22 N5 N6 111.9(3) N1 C9 C8 118.9(4) C24 C23 C34 121.1(4) C1 N1 C9 117.9(4) C28 C23 C24 118.6(4) N2 C10 C2 121.8(4) C28 C23 C34 120.2(4) C10 N2 N3 111.1(3) C25 C24 C23 120.7(5) C11 N3 N2 112.6(3) C23 C28 C27 120.5(5) C29 C12 C11 121.6(4) C26 C27 C28 120.2(5) C29 C12 C33 118.2(4) C27 C26 C25 120.6(5) C33 C12 C11 120.2(4) C26 C25 C24 119.4(5) N3 C11 C12 119.4(4) C30 C29 C12 121.2(5) N3 C11 C34 123.6(3) C32 C33 C12 120.1(4) C12 C11 C34 116.9(4) C30 C31 C32 119.4(5) C13 N4 C17 116.7(4) C31 C32 C33 120.7(5) C13 C14 C22 119.6(4) C31 C30 C29 120.4(5) C15 C14 C13 117.8(4) N6 C34 C11 122.8(3) C15 C14 C22 122.6(4) N6 C34 C23 118.3(3) C17 C16 C15 117.9(4) C23 C34 C11 118.5(4) Table 4. Hydrogen bonding parameters for compound 1. D-H∙∙∙A D-H (Å) H∙∙∙A (Å) D∙∙∙A (Å) ∠ D-H∙∙∙A (°) Symmetry C13-H5∙∙∙N1 0.99(4) 2.60(4) 3.587(7) 170(3) 1-x, 2-y, 2-z 2.4. Theoretical calculations Gaussian 09 program [29] has been used for quantum chemical calculations. The possible ground state structures have been optimized with density functional theory (DFT) at B3LYP/6-311G**. GaussView 5 program [30] was used for the visualization of the studied systems. 2.5. Hirshfeld surfaces calculation Hirshfeld surface analysis helps as a powerful set-up for obtaining additional insight into the intermolecular interaction of molecular crystals. The size and shape of Hirshfeld surface allows the qualitative and quantitative study and imagining of intermolecular close contacts in molecular crystals [31]. The Hirshfeld surface enclosing a molecule is defined by a set of points in 3D space where the contribution to the electron density from the molecule of interest is equal to the contribution from all other molecules. Molecular Hirshfeld surfaces are constructed based on electron distribution calculated as the sum of spherical atom electron densities [32]. Thus, an iso-surface is obtained, and for each point of the iso-surface two distances can be defined: de, the distance from the point to the nearest atom outside to the surface, and di, the distance to the nearest atom inside to the surface. Moreover, the identification of the regions of particular importance to intermolecular interactions is obtained by mapping normalized contact distance (dnorm), expressed as: dnorm = (di-rivdw)/rivdw+(de-revdw)/revdw; where rivdw and revdw are the van der Waals radii of the atoms [33]. The value of dnorm is negative or positive when intermolecular contacts are shorter or longer than rvdw, respectively. Patra et al. / European Journal of Chemistry 12 (4) (2021) 394-400 397 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.394-400.2153 Figure 1. The ORTEP diagram (30% ellipsoidal probability) of compound 1 with atom numbering scheme. Figure 2. The self-assembled molecular rectangle through hydrogen bonding in compound 1. Graphical plots of the molecular Hirshfeld surfaces mapped with dnorm employ the red-white-blue color scheme, where red color indicates the shorter intermolecular contacts, white color show the contacts around the rvdw separation, and blue color is used to indicate the longer contact distances. Because of the symmetry between de and di in the expression for dnorm, where two Hirshfeld surfaces touch, both will display a red spot identical in color intensity as well as size and shape [34]. The combination of de and di in the form of a 2D fingerprint plot provides summary of intermolecular contacts in the crystal and are in complement to the Hirshfeld surfaces. Such plots provide information about the intermolecular interactions in the immediate environment of each molecule in the asymmetric unit. Moreover, the close contacts between particular atom types can be highlighted in so-called resolved fingerprint plots, which allow the facile assignment of an intermolecular contact to a certain type of interaction and quantitatively summarize the nature and type of intermolecular contacts. Two additional colored properties (shape index and curvedness) based on the local curvature of the surface can also be specified [35]. The Hirshfeld surfaces are mapped with dnorm, shape-index, curvedness and 2D fingerprint plots (full and resolved) presented in this paper were generated using Crystal-Explorer 3.1 [36]. 3. Results and discussion 3.1. Synthesis and structure The compound 1 was synthesized in good yield and as yellow solid by condensing diphenylethanedione dihydrazone and quinoline 3-carboxaldehyde in 1:2 molar ratio in anhydrous methanol [37,38]. The compound 1 under study shows characteristic peak at 1612 cm-1 is assigned to the imine (C=N) stretching frequencies. The 1H NMR spectra of the compound 1 in CDCl3 showed a singlet at δ 7.80 ppm due to HC=N proton, other aryl protons resonates in between δ 9.16 to 7.47 ppm. In the 13C NMR spectra the –C=N carbon appears at δ 166.53 ppm and the other aryl carbons resonate between δ 157.50 to 127.48 ppm (expected region). Compound 1 crystallizes in the triclinic space group P-1 and the asymmetric unit contains a single molecule of compound 1 (Scheme 1). Due to the steric crowding between the two phenyl groups substituted on the central C-C bond in compound 1 the N=C- C=N and C(Ph)- C-C-C(Ph) torsion angles about this bond are - 102.25 and -93.55°, respectively. The molecule consists of two identical linear parts connected covalently by a -C-C- bond at the C11 and C34 carbon (Figure 1). Each segment of the molecule is linear and is nearly orthogonally disposed with respect to each other. This gives rise to the ‘L’ shape of the molecule with two phenyl groups acting as small appendages. Each of the linear segments of the molecule consists of a phenyl and a quinoline group on either side of the central azo group. The molecule is rigid and the plane of the quinoline groups on both branches is perpendicular to each other. The ‘L’ shape of the molecule is self-complementary for hydrogen bonding. The crystal structure analysis reveals a hydrogen bonded supramolecular rectangle (Figure 2). The quinoline nitrogen atom N1 acts as an acceptor for the hydrogen attached to the C13 carbon atom adjacent to the N atom. The hydrogen bonding parameters are given in Table 4. The size and aromatic nature of the quinoline fragment reveals a high propensity for strong dispersive interactions between the flat molecular surfaces of these rings in the condensed solid phase. This spatial as well as enthalpic element is well expressed in the crystal packing arrangement of compound 1. 398 Patra et al. / European Journal of Chemistry 12 (4) (2021) 394-400 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.394-400.2153 Figure 3. The π-π stacking of hydrogen bonded molecular rectangles in compound 1. Figure 4. Optimized molecular structure of compound 1. LUMO HOMO Figure 5. Surface plots of HOMO and LUMO of the ligand 1. The π-π stacking interaction between the aromatic 3- quinoline rings of neighboring molecules has been observed in the crystals of compound 1. Face-to-face overlap between the phenyl substituent of one species and the quinoline substituent of another species provides an additional stabilizing contri- bution. Hydrogen bonded molecular rectangles are thus joined at their corners by π-π interaction (Figure 3). In a unit cell four such rectangles are there, center of each is positioned at the cell corners. 3.2. Theoretical investigations The optimized bond lengths and angles for the compound 1 is well replicated with the experimental single crystal X-ray diffracttion structure data. The optimized structure of compound 1 has been shown in Figure 4. The surface plots of HOMO and LUMO of compound 1 have been depicted in Figure 5. Patra et al. / European Journal of Chemistry 12 (4) (2021) 394-400 399 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.394-400.2153 (a) (b) (c) Figure 6. Hirshfeld surfaces of compound 1: (a) 3D dnorm surface, (b) shape index, and (c) curvedness. (a) (b) (c) (d) Figure 7. 2D Fingerprint plots of compound 1, (a) standard full, (b) resolved into C···C, (c) resolved into H···H, and (d) N···H contacts, showing the percentages of contacts contributing to the total Hirshfeld surface area of the molecule. 3.3. Molecular Hirshfeld surfaces The Hirshfeld surface is a suitable tool for describing the surface characteristics of molecules. The molecular Hirshfeld surface of compound 1 was generated using a standard (high) surface resolution with the 3D dnorm surfaces mapped over a fixed color scale of -0.22 (red) to 1.4 Å (blue). The shape index mapped in the color range of -0.99 to 1.0, and the curvedness was in the range of -4.0 to 0.4. The surfaces were shown to be transparent to allow visualization of the molecular moiety in a similar orientation for all of the structures around which they were calculated. The molecular Hirshfeld surface (dnorm, Shape index and Curvedness) of compound 1 has been shown in Figure 6. The Hirshfeld surface analysis of compound 1 shows that C···C, H···H, C···H, and N···H interactions of 13.1, 52.3, 9.9 and 7.4%, respectively, which revealed that the main inter- molecular interactions were H···H intermolecular interactions. Both the C···C and C···H interactions were represented almost same area by a small area in the right side of the top in the 2D fingerprint map, whereas the H···H interactions were represented by the largest in the fingerprint plot (Figure 7) and thus had the most significant contribution to the total Hirshfeld surfaces (52.3%). 3.4. Molecular electrostatic potential (MEP) The potential increases in the order red < yellow < green < blue < pink < white. Red and yellow represent the regions of most negative electrostatic potential which is related to electrophilic reactivity, white represents the region of most positive electrostatic potential which is related to nucleophilic reactivity and blue represents the region of zero potential. Molecular electrostatic potential (MEP) of compound 1 has been shown in Figure 8. Figure 8. Molecular electrostatic potential of compound 1. 4. Conclusion In conclusion, we have synthesized a polydentate imino quinolyl ligand, N,N’-bis-(3-quinolylmethylene)diphenylethane dione dihydrazone and determined its single crystal X-ray structure at room temperature. Interestingly this molecule is predisposed for supramolecular rectangles due to its ‘L’ shaped geometry as well as self-complementarity in hydrogen bonding. Generation of molecules or supramolecular architecture of different well-known geometries such as triangles, square, pentagon- in general n-gon is a challenging task in crystal engineering. In this respect, the molecule reported here shows how the design principle, especially ‘L’ shape and suitable positioning of acceptor and donors can give rise to targeted geometry. The Hirshfeld surface analysis of compound 1 shows that C···C, C···H, H···H, and N···H interactions of 13.1, 9.9, 52.3, and 7.4%, respectively, which exposed that the main inter- molecular interactions were H···H intermolecular interactions. 400 Patra et al. / European Journal of Chemistry 12 (4) (2021) 394-400 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.394-400.2153 Acknowledgements Goutam Kumar Patra would like to thank the Department of Science and Technology (SR/FST/CSI-264/2014 and EMR/ 2017/0001789) and Department of Biotechnology, Government of India, New Delhi for financial support. Amit Kumar Manna thanks the Council for Scientific and Industrial Research, Government of India, for financial support in the form of research fellowships. Supporting information CCDC-805764 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 interests: The authors declare that they have no conflict of interest. Ethical approval: All ethical guidelines have been adhered. Sample availability: Sample of compound 1 is available from the author. CRediT authorship contribution statement Conceptualization: Goutam Kumar Patra; Methodology: Goutam Kumar Patra; Software: Dinesh De; Validation: Amit Kumar Manna; Formal Analysis: Amit Kumar Manna; Investigation: Amit Kumar Manna; Resources: Goutam Kumar Patra; Data Curation: Dinesh De; Writing - Original Draft: Goutam Kumar Patra; Writing - Review and Editing: Goutam Kumar Patra; Visualization: Amit Kumar Manna; Funding acquisition: Goutam Kumar Patra; Supervision: Goutam Kumar Patra; Project Administration: Goutam Kumar Patra. ORCID Amit Kumar Manna https://orcid.org/0000-0002-9605-2168 Dinesh De https://orcid.org/0000-0001-7850-8718 Goutam Kumar Patra https://orcid.org/0000-0003-3151-0284 References [1]. Janiak, C.; Scharmann, T. G. Polyhedron 2003, 22 (8), 1123–1133. [2]. Janiak, C. Dalton Trans. 2003, 14, 2781–2804. [3]. Rout, K.; Manna, A. K.; Sahu, M.; Mondal, J.; Singh, S. K.; Patra, G. K. RSC Adv. 2019, 9 (44), 25919–25931. [4]. Pal, S.; Pal, S. 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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). https://www.ccdc.cam.ac.uk/structures/ mailto:data_request@ccdc.cam.ac.uk https://orcid.org/0000-0002-9605-2168 https://orcid.org/0000-0001-7850-8718 https://orcid.org/0000-0003-3151-0284 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. Materials and physical measurements 2.2. Synthesis of compound 1 2.3. X-ray crystallography 2.4. Theoretical calculations 2.5. Hirshfeld surfaces calculation 3. Results and discussion 3.1. Synthesis and structure 3.2. Theoretical investigations 3.3. Molecular Hirshfeld surfaces 3.4. Molecular electrostatic potential (MEP) 4. Conclusion Acknowledgements Supporting information Disclosure statement ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField15: PrintField16: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: PrintField25: PrintField26: