Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylidene))bis(methanylylidene))diphenol European Journal of Chemistry 13 (1) (2022) 49-55 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.13.1.49-55.2175 European Journal of Chemistry View Journal Online View Article Online Synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylidene)) bis(methanylylidene))diphenol Goutam Kumar Patra 1,* and Dinesh De 2 1 Department of Chemistry, Faculty of Physical Sciences, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh, 495009, India 2 Department of Basic Science, Vishwavidyalaya Engineering College, Ambikapur, CSVTU-Bhilai, Chhattisgarh, 497001, India * 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.13.1.49-55.2175 Received: 07 August 2021 Received in revised form: 09 October 2021 Accepted: 01 November 2021 Published online: 31 March 2022 Printed: 31 March 2022 The synthesis, characterization, and theoretical studies of the title compound has been reported in this study. The molecular structure has been characterized by room- temperature single-crystal X-ray diffraction study which reveals that it has an angular shape with intramolecular and intermolecular hydrogen bonding. Crystal data for the title compound, C27H22N2O2 (M =406.46 g/mol): monoclinic, space group C2/c (no. 15), a = 36.371(10) Å, b = 4.6031(12) Å, c = 12.192(3) Å, β = 94.972(6)°, V = 2033.5(9) Å3, Z = 4, T = 100 K, μ(MoKα) = 0.084 mm-1, Dcalc = 1.328 g/cm3, 8812 reflections measured (2.248° ≤ 2Θ ≤ 49.734°), 1773 unique (Rint = 0.0323, Rsigma = 0.0239) which were used in all calculations. The final R1 was 0.0411 (I > 2σ(I)) and wR2 was 0.1165 (all data). In crystal structure, the molecule exits in the enol form and is located on a two-fold axis of symmetry; where the central methylene carbon atom of the diphenylmethane moiety is displaced from the aromatic ring planes. The Hirshfeld surface analysis of the title compound shows that H···H, C···H, and O···H interactions of 53.3, 13.2, and 5.4%; respectively, which exposed that the main intermolecular interactions were H···H intermolecular interactions. The HOMO-LUMO energy gap in the title compound is 2.9639 eV. Molecular electrostatic potential of the investigated compound has also been studied. H-bonding Di-Schiff base X-ray crystal structure Density functional theory Hirshfeld surface analysis Molecular electrostatic potential Cite this: Eur. J. Chem. 2022, 13(1), 49-55 Journal website: www.eurjchem.com 1. Introduction Compounds containing imine group (–CH=N–) are known as Schiff bases and are usually prepared by condensing primary amines with active carbonyl compounds, in di-Schiff base there are two units of imine group [1-3]. They are versatile and flexible ligands for forming multinuclear transition metal complexes with interesting properties viz. reversible oxygen- binding ability and catalysis for several reactions [4-7]. The predilection and adaptability of imine functionality can be endorsed to its effortlessness synthesis, stability towards hydrolysis, and most prominently the flexible nature of -N=CH- bonds through tautomerism, which facilitate its incorporation in different applications [8,9]. Bis-bidentate Schiff base ligands have also attracted significant interest as building blocks in metallo-supramolecular chemistry, especially in the synthesis of helicate [10-13]. Free N-salicylideneanilines are often thermo- chromic due to a temperature-dependent equilibrium between the keto-amine and enol-imino form [14,15]. Schiff bases with ortho-substituted aromatic rings have found to be most responsive for chelation with transition metal ions. The chelation of transition metal ions to the >C=N linkage would develop intramolecular charge transfer (ICT) transition or make ligand to metal charge transfer (LMCT) transition, which could be useful for the visual sensing of the metal ions [16-18]. In this regard, 4-(diethylamino)-2-hydroxybenzalde- hyde is a well-known chromophore used in the area of chemo- sensors. Similar type of bis-N,O-bidentate Schiff-base ligands can be electronically and configurationally controlled, leading to a systematic study of the self-assembly process in solution [19]. In continuation to our previous research work for the search potential important functionalized bis-Schiff [20-22], we report here the synthesis, crystal structure, DFT studies, and Hirshfeld surface analysis of a multidentate bis-Schiff base, 2,2'- (((methylene-bis(4,1- phenylene))bis(azanylylidene))bis(methanylylidene))diphenol (1), 1+2 condensate of4-(4-aminobenzyl)benzenamine and 2- hydroxybenzaldehyde.For designing bis-Schiff base compound 1, we have selected amine part using two aniline moieties joined through a methylene rotor at their para positions and aldehyde part containing strong electron donating hydroxo group also in ortho position to the aldehyde, which makes it electron rich [23,24]. ABSTRACT RESEARCH ARTICLE KEYWORDS https://dx.doi.org/10.5155/eurjchem.13.1.49-55.2175 https://www.eurjchem.com/ https://dx.doi.org/10.5155/eurjchem.13.1.49-55.2175 mailto:goutam.patra@ggu.ac.in http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.13.1.49-55.2175&domain=pdf&date_stamp=2022-03-31 50 Patra and De / European Journal of Chemistry 13 (1) (2022) 49-55 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.1.49-55.2175 Table 1. Crystal data and structure refinement parameters for the title compound 1. Empirical formula C27H22N2O2 Formula weight 406.46 Temperature (K) 100 Crystal system Monoclinic Space group C2/c a, (Å) 36.371(10) b, (Å) 4.6031(12) c, (Å) 12.192(3) α (°) 90 β (°) 94.972(6) γ (°) 90 Volume (Å3) 2033.5(9) Z 4 ρcalc(g/cm3) 1.328 μ (mm-1) 0.084 F(000) 856.0 Crystal size (mm3) 0.22 × 0.21 × 0.18 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 2.248 to 49.734 Index ranges -42 ≤ h ≤ 42, -5 ≤ k ≤ 5, -14 ≤ l ≤ 14 Reflections collected 8812 Independent reflections 1773 [Rint = 0.0323, Rsigma = 0.0239] Data/restraints/parameters 1773/0/146 Goodness-of-fit on F2 1.038 Final R indexes [I≥2σ (I)] R1 = 0.0411, wR2 = 0.1063 Final R indexes [all data] R1 = 0.0561, wR2 = 0.1165 Largest diff. peak/hole (e.Å-3) 0.12/-0.15 N N OH HO H2N NH2 C HO + CH3OH 4 h O H Scheme 1. Synthesis of compound 1. 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 the title compound 1 The compound 1 has been synthesized by following a reported procedure [25]. Bis(4-aminophenyl)methane (1 mmol) was dissolved in 30mL of dehydrated methanol, and 2- hydroxybenzaldehyde (2 mmol) was added drop-wise over 10 min. The reaction mixture was refluxed for 4h at 70 °C, maintaining dry condition. A yellow precipitate was filtered and washed several times with n-hexane and then re-crystallized from methanol and dried in vacuum to obtain the pure yellow solid. Single crystals suitable for analysis were obtained by the slow evaporation of methanolic solution (Scheme 1). 2, 2'-(((Methylene-bis(4, 1-phenylene))bis(azanylylidene)) bis(methanylylidene))diphenol: Color: Yellow. Yield: 85%. FT- IR (KBr, ν, cm-1): 1617, 1595, 1563. 1H-NMR (400 MHz, CDCl3, δ, ppm): 13.28 (bs, 2H, OH), 8.65 (s, 2H, =CH), 7.41 (m, J = 7.3 Hz, 4H, Ar-H), 7.26 (m, 8H, Ar-H), 7.04 (d, J = 7.8 Hz, 2H, Ar-H), 6.96 (t, J = 7.8 Hz, 2H, Ar-H), 4.07 (s, 2H, CH2). ESI-MS (m/z, %): 407.39 (LH2+, 100%). Anal. calcd. for C27H22N2O2: C, 79.78; H, 5.46; N, 6.89. Found: C, 79.62; H, 5.43; N, 6.97%. UV-Vis (MeOH, λmax, nm): 330, 280. 2.3. X-ray crystallography Single crystal X-ray data of compound 1 was collected using MoKα (λ = 0.71073 Å) radiation on a Bruker APEX II diffracto- meter equipped with CCD area detector. The crystal was kept at 100 K during data collection. Using Olex2 [26], the structure was solved with the SHELXS [27] structure solution program using Direct Methods and refined with the SHELXL [28] refinement package using Least Squares minimization. Atoms other than hydrogen atoms were treated anisotropically. The hydrogen atoms were geometrically fixed. The crystallographic details of compound 1 are summarized in Table 1, the bond lengths, bond angles and torsion angles of compound 1 are listed in Tables 2-4, respectively. 2.4. Theoretical calculations Gaussian 09 program [29] has been used for the 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 Surface Calculations For obtaining additional insight into the intermolecular interaction of molecular crystals, Hirshfeld surface analysis helps as a powerful set-up. Patra and De / European Journal of Chemistry 13 (1) (2022) 49-55 51 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.1.49-55.2175 Table 2. Bond lengths for the title compound. Atom Atom Length (Å) Atom Atom Length (Å) N1 C8 1.4139(19) C11 C14 1.513(2) N1 C7 1.2793(19) C11 C12 1.382(2) O1 C5 1.344(2) C5 C6 1.387(2) C8 C13 1.379(2) C10 C9 1.382(2) C8 C9 1.388(2) C13 C12 1.379(2) C4 C7 1.445(2) C3 C2 1.372(2) C4 C5 1.399(2) C2 C1 1.375(3) C4 C3 1.391(2) C6 C1 1.372(3) C11 C10 1.376(2) Table 3. Bond angles for the title compound. Atom Atom Atom Angle (°) Atom Atom Atom Angle (°) C7 N1 C8 121.43(13) O1 C5 C6 119.46(16) C13 C8 N1 117.09(13) C6 C5 C4 119.45(16) C13 C8 C9 118.02(14) C11 C10 C9 122.02(15) C9 C8 N1 124.88(14) C12 C13 C8 121.11(15) C5 C4 C7 121.40(14) C10 C9 C8 120.16(15) C3 C4 C7 120.01(14) C2 C3 C4 121.51(17) C3 C4 C5 118.59(15) C111 C14 C11 109.79(18) N1 C7 C4 122.28(14) C13 C12 C11 121.30(15) C10 C11 C14 121.49(13) C3 C2 C1 119.27(17) C10 C11 C12 117.31(14) C1 C6 C5 120.46(18) C12 C11 C14 121.11(13) C6 C1 C2 120.71(17) O1 C5 C4 121.09(15) 1 1-x, +y, 3/2-z. Table 4. Torsion angles for the title compound. A B C D Angle (°) A B C D Angle (°) N1 C8 C13 C12 178.34(14) C5 C4 C3 C2 1.3(2) N1 C8 C9 C10 -179.75(14) C5 C6 C1 C2 0.1(3) O1 C5 C6 C1 -179.61(17) C10 C11 C14 C11 1 -93.61(15) C8 N1 C7 C4 179.78(12) C10 C11 C12 C13 0.8(2) C8 C13 C12 C11 1.7(2) C13 C8 C9 C10 1.5(2) C4 C5 C6 C1 0.6(3) C9 C8 C13 C12 -2.8(2) C4 C3 C2 C1 -0.5(3) C3 C4 C7 N1 178.71(15) C7 N1 C8 C13 -166.32(14) C3 C4 C5 O1 178.93(15) C7 N1 C8 C9 14.9(2) C3 C4 C5 C6 -1.3(2) C7 C4 C5 O1 -0.3(2) C3 C2 C1 C6 -0.2(3) C7 C4 C5 C6 179.52(15) C14 C11 C10 C9 174.60(15) C7 C4 C3 C2 -179.53(14) C14 C11 C12 C13 -175.94(15) C11 C10 C9 C8 1.0(2) C12 C11 C10 C9 -2.1(2) C5 C4 C7 N1 -2.1(2) C12 C11 C14 C111 82.95(14) 1 1-x, +y, 3/2-z. The size and shape of Hirshfeld surface allow 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 built based on electron distribution calculated as the sum of spherical atom electron densities [32,33]. The identification of the regions of particular importance to intermolecular interactions is achieved 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 [34]. The value of dnorm is negative or positive when intermolecular contacts are shorter or longer than rvdw, respectively. Due to 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 [35]. The mixture of de and di in the form of a 2D fingerprint plot provides a summary of intermolecular contacts in the crystal and are in complement to the Hirshfeld surfaces [34]. The information about the intermolecular interactions in the immediate environment of each molecule in the asymmetric unit is achieved by such plots. In addition, the close contacts between particular atom types can be highlighted in so-called resolved fingerprint plots [36], 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 [37]. The Hirshfeld surfaces are mapped with dnorm, shape-index, curvedness and 2D fingerprint plots (full and resolved) reported in this manuscript were generated using Crystal-Explorer 3.1 [38]. 2.6. Molecular electrostatic potential The molecular electrostatic potential at a given point around a molecule can be defined in terms of total charge distribution of the molecule and related with the dipole moments. It supplies a method to understand the electron density which is useful for determining the electrophilic reactivity and nucleophilic reactivity along with hydrogen- bonding interactions [39,40]. 3. Results and discussion 3.1. Synthesis and structure The compound 1 was synthesized in good yield and as yellow solid by condensing bis(4-aminophenyl)methane and 2- hydroxybenzaldehyde in 1:2 molar ratio in anhydrous methanol (Scheme 1). It crystallizes in monoclinic space group C2/c and the asymmetric unit contains a single molecule of compound 1. The molecule of compound 1 has crystallo- graphically imposed two-fold plain of symmetry. The ORTEP diagram of the compound 1 is shown in Figure 1. 52 Patra and De / European Journal of Chemistry 13 (1) (2022) 49-55 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.1.49-55.2175 Table 5. List of hydrogen bonding in compound 1. D H A D-H (Å) H···A (Å) D-A (Å) ∠ D-H···A (°) C7 H7 O1 0.950 2.563 3.417 149.75 C9 H9 O1 0.950 3.279 4.070 141.97 C3 H3 O1 0.950 2.718 3.539 145.03 O1 H1 N1 0.840 1.841 2.589 147.81 Figure 1. The ORTEP diagram of the compound 1. H-bondings are shown in dotted line. (a) (b) (c) (d) Figure 2. Crystal structure of compound 1, (a, b) top view, (b, c) layer structure. H-bondings are shown in dotted line The central methylene C atom (C14) of the diphenyl- methane moiety is displaced from the aromatic ring planes. The molecule of compound 1 is angular V-shaped conformation, with atom C14 coinciding with a crystallographic two-fold axis. The two O-H groups are trans to each other. The angle between the two arms originating from central methylene C atom (C14) is 109.77° and the symmetry-related C1/C2/C3/C4/C5/C6 phenol ring is 78.87°. The C8/C9/C10/C11/C12/C13 phenyl ring is not coplanar with the C1/C2/C3/C4/C5/C6 phenol ring, the interplanar angle is 12.93°. The imino plane is almost coplanar with the phenol ring, it is, rather, twisted considerably out of the plane of the phenyl ring of bis(4-aminophenyl) methane. The dihedral angle between the two unique phenyl rings is 177.68° while the dihedral angle between the two central phenyl rings is 93.73°. In the crystal structure of compound 1, there exists two intramolecular O–H⋯N hydrogen bonds between the hydroxyl hydrogen and imino nitrogen atoms. Detailed information regarding hydrogen bonds in the molecules of compound 1 is given in Table 5. The packing of the molecules is shown in Figure 2. The molecules are stabilized by several weak non-covalent interactions including C-H⋯O bonds, and π-π interactions resulting the formation of layered structure with direction of propagation of two adjacent layers are in opposite direction. Each layer is stabilized by π-π interactions. Top view of the structure formed rectangular channel (Figure 2a and b). There is a chance of keto-enol tautomerism in compound 1, but the in the crystal structure of compound 1, the molecule exits in the enol form. 3.2. Theoretical investigations The optimized bond length and angles for the compound 1 is well replicated with the experimental single crystal X-ray diffraction structure data. The optimized structure of compound 1 has been shown in Figure 3. The surface plots of HOMO and LUMO of compound 1 have been depicted in Figure 4. The ground state energy of compound 1 achieved in DFT calculation is -1302.14 a.u. The HOMO-LUMO energy gap in compound 1 is 2.9639 eV. 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). Patra and De / European Journal of Chemistry 13 (1) (2022) 49-55 53 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.1.49-55.2175 Figure 3. Optimized molecular structure of compound 1. ELUMO = -5.5500 eV ↕∆E = 2.9639 eV EHOMO = -8.5139 eV Figure 4. HOMO-LUMO energy levels and energy gap of the compound 1. (a) (b) (c) Figure 5. Hirshfeld surfaces of compound 1, (a) 3D dnorm surface, (b) shape index, and (c) curvedness. The shape index mapped in the color range of -1.0 to 1.0, and 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 surfaces (dnorm, Shape index and curvedness) of compound 1 have been shown in Figure 5. The pattern of adjacent red and blue triangles that appears on the shape index surfaces of compound 1 and a relatively large and flat green region at the same side of the molecule on the corresponding curvedness surfaces, confirms the presence of π···π interactions in compound 1. The Hirshfeld surface analysis of compound 1 shows that H···H, C···H, and O···H interactions of 53.3, 13.2 and 5.4%, respectively, which revealed that the main intermolecular interactions were H···H intermolecular interactions. Both the C···H and O···H interactions were represented 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 6) and thus, had the most significant contribution to the total Hirshfeld surfaces (53.3%). 3.4. Molecular electrostatic potential Molecular electrostatic potential can simultaneously display molecular size, shape as well as positive, negative and neutral electrostatic potential regions in terms of color grading. The order of the electrostatic potential is as follows: Red < orange < yellow < green < blue. Negative regions of molecular electrostatic potential are rich in electrons and are focused on electronegative atoms. Positive regions are electrons deficient and these sites are mainly around hydrogen atoms. Molecular electrostatic potential of compound 1 has been shown in Figure 7. 4. Conclusion In conclusion, we have reported here the synthesis, crystal structure and Hirshfeld surface analysis of a di-Schiff base ligand, 2,2'-(((methylene-bis(4,1-phenylene))bis(azanylylide- ne))bis(methanylylidene))diphenol (1), which is a building block of several metal helicates. 54 Patra and De / European Journal of Chemistry 13 (1) (2022) 49-55 2022 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.13.1.49-55.2175 (a) (b) (c) (d) Figure 6. 2D Fingerprint plots of compound 1, (a) standard full, (b) resolved into H···H, (c) resolved into C··H, and (d) O···H contacts, showing the percentages of contacts contributing to the total Hirshfeld surface area of the molecule. Figure 7. Molecular electrostatic potential of compound 1. Interestingly, this molecule has an angular shape with intramolecular and intermolecular hydrogen bonding. In crystal structure, the molecule exits in the enol form and is located on a two-fold axis of symmetry; where the central methylene carbon atom of the diphenylmethane moiety is displaced from the aromatic ring planes. The Hirshfeld surface analysis of compound 1 shows that H···H, C···H, and O···H interactions of 53.3, 13.2, and 5.4%; respectively, which exposed that the main intermolecular interactions were H···H intermolecular interactions. 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. Supporting information CCDC-2101426 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 the compound 1 is available from the author. CRediT authorship contribution statement Conceptualization: Goutam Kumar Patra; Methodology: Goutam Kumar Patra; Software: Dinesh De; Validation: Goutam Kumar Patra; Formal Analysis: Goutam Kumar Patra; Investigation: Goutam Kumar Patra; Resources: Goutam Kumar Patra; Data Curation: Dinesh De Writing - Original Draft: Goutam Kumar Patra; Writing - Review and Editing: Dinesh De; Visualization: Dinesh De; Funding acquisition: Goutam Kumar Patra; Supervision: Goutam Kumar Patra; Project Administration: Goutam Kumar Patra. ORCID and Email Goutam Kumar Patra goutam.patra@ggu.ac.in https://orcid.org/0000-0003-3151-0284 Dinesh De d2chem@gmail.com https://orcid.org/0000-0001-7850-8718 References [1]. Dey, S.; Sen, C.; Sinha, C. Chromogenic Hydrazide Schiff Base Reagent: Spectrophotometric Determination of CN- Ion. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2020, 225 (117471), 117471. [2]. Sztanke, K.; Maziarka, A.; Osinka, A.; Sztanke, M. 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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). 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 the title compound 1 2.3. X-ray crystallography 2.4. Theoretical calculations 2.5. Hirshfeld Surface Calculations 2.6. Molecular electrostatic potential 3. Results and discussion 3.1. Synthesis and structure 3.2. Theoretical investigations 3.3. Molecular Hirshfeld surfaces 3.4. Molecular electrostatic potential 4. Conclusion Acknowledgements Supporting information Disclosure statement CRediT authorship contribution statement ORCID and Email References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField15: PrintField16: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: PrintField25: PrintField26: