Crystal structure and computational studies of N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline European Journal of Chemistry 12 (4) (2021) 454-458 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.12.4.454-458.2171 European Journal of Chemistry View Journal Online View Article Online Crystal structure and computational studies of N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline Sehriman Atalay 1, Mustafa Macit 2 and Hakan Bulbul 1,* 1 Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55200, Samsun, Turkey atalays@omu.edu.tr (S.A.), hbulbul@omu.edu.tr (H.B.) 2 Department of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55200, Samsun, Turkey mmacit@omu.edu.tr (M.M.) * Corresponding author at: Department of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55200, Samsun, Turkey. e-mail: hbulbul@omu.edu.tr (H. Bulbul). 10.5155/eurjchem.12.4.454-458.2171 Received: 31 July 2021 Received in revised form: 03 October 2021 Accepted: 23 October 2021 Published online: 31 December 2021 Printed: 31 December 2021 The Schiff base compound, N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline, has been synthesized and characterized by X-ray diffraction method. The title compound, C19H16FNO, crystallizes in triclinic, space group P-1 (no. 2), a = 10.6343(9) Å, b = 11.4720(10) Å, c = 13.8297(13) Å, α = 102.466(7)°, β = 104.763(7)°, γ = 98.972(7)°, V = 1552.7(2) Å3, Z = 4, T = 293(2) K, μ(MoKα) = 0.086 mm-1, Dcalc = 1.255 g/cm3, 24355 reflections measured (3.16° ≤ 2Θ ≤ 51°), 5779 unique (Rint = 0.0794, Rsigma = 0.0696) which were used in all calculations. The final R1 was 0.0373 (I > 2σ(I)) and wR2 was 0.0763 (all data). The title compound contains two molecules with a similar structure in the asymmetric unit cell. The packing of the crystal structure is determined by weak C–H···F and C-H···N intermolecular hydrogen bonds. The contributions of these weak interactions in the crystal structure were calculated by the Hirshfeld surfaces and examined by the intermolecular interactions within the structure. The existence, nature and percentage contribution of different intermolecular interactions H···H, C···H, N···H, and F···H were determined using Hirshfeld surface analysis and fingerprint plots. Synthesis Crystallography Computational studies Single-crystal structure Hirshfeld surface analysis Two-dimensional fingerprint Cite this: Eur. J. Chem. 2021, 12(4), 454-458 Journal website: www.eurjchem.com 1. Introduction The general formula of Schiff bases, which are compounds bearing imine groups, are RCH=NR'. They are formed as a result of condensation of aldehydes and ketones with primary amines. These compounds, discovered by Hugo Schiff, are prepared by condensing an aldehyde or a carbonyl compound with an amine group in different solvents and which are the most familiar, classical method. Numerous spectroscopic and crystallographic studies have been carried out to explain the structure of Schiff bases in detail. In particular, o-hydroxy Schiff bases, which form intra- molecular hydrogen bonds and have different tautomeric struc- tures, are of great interest. o-.hydroxy Schiff bases generally exist in two possible tautomeric forms [1-4]. In addition, carbon-nitrogen double bonds in Schiff base compounds have played an important role in the advancement of chemistry. The important use of Schiff bases is as a starting material in the synthesis of drugs produced in pharmacology [5,6]. Naphthalene-containing Schiff bases also synthesized with two benzene rings fused to each other do not contain heteroatoms or carry substituents. They are also called benzenoid polycyclic aromatic hydrocarbons [7]. Currently, Schiff bases are being investigated as free radical scavengers that can be developed as potential antioxidants. Extending free radical delocalization of imino groups and substituent is due to the free radical scavenging effects of Schiff bases [8-10]. In this study, we have presented the synthesis and crystal structure analysis of a novel Schiff base compound, N-((2-ethoxynaphthalen-1-yl)methyle ne)-4-fluoroaniline which contains naphthalene used as an antioxidant. Furthermore, Hirshfeld surface analysis and fingerprint plots were used to establish the presence, nature, and percentage contribution of the different types of inter- molecular interactions in the crystal. 2. Experimental 2.1 Instrumentation X-ray diffraction data of the examined structure were collected using the STOE IPDS-II diffractometer and MoKα (λ = 0.71073 Å) beam in the X-ray Laboratory of the Faculty of Arts and Sciences, Ondokuz Mayıs University. The structure solution of the crystals was obtained using direct methods with the program SHELXS-97 [11,12]. ABSTRACT RESEARCH ARTICLE KEYWORDS https://dx.doi.org/10.5155/eurjchem.12.4.454-458.2171 https://www.eurjchem.com/ https://dx.doi.org/10.5155/eurjchem.12.4.454-458.2171 mailto:atalays@omu.edu.tr mailto:hbulbul@omu.edu.tr mailto:mmacit@omu.edu.tr mailto:hbulbul@omu.edu.tr http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.12.4.454-458.2171&domain=pdf&date_stamp=2021-12-31 Atalay et al. / European Journal of Chemistry 12 (4) (2021) 454-458 455 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.454-458.2171 Table 1. Crystallographic characteristics and X-ray data collection and structure-refinement parameters for the title compound. Empirical formula C19H16FNO Formula weight 293.33 Temperature (K) 293(2) Crystal system Triclinic Space group P-1 a, (Å) 10.6343(9) b, (Å) 11.4720(10) c, (Å) 13.8297(13) α (°) 102.466(7) β (°) 104.763(7) γ (°) 98.972(7) Volume (Å3) 1552.7(2) Z 4 ρcalc (g/cm3) 1.255 μ (mm-1) 0.086 F(000) 616.0 Crystal size (mm3) 0.61 × 0.38 × 0.17 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 3.16 to 51 Index ranges -12 ≤ h ≤ 12, -13 ≤ k ≤ 13, -16 ≤ l ≤ 16 Reflections collected 24355 Independent reflections 5779 [Rint = 0.0794, Rsigma = 0.0696] Data/restraints/parameters 5779/40/515 Goodness-of-fit on F2 0.789 Final R indexes [I≥2σ (I)] R1 = 0.0373, wR2 = 0.0656 Final R indexes [all data] R1 = 0.0975, wR2 = 0.0763 Largest diff. peak/hole (e.Å-3) 0.09/-0.12 CCDC no 2100901 Programs SHELXL97 [11,12], X-AREA [13], X-RED32 [13], ORTEP-3 [14], WinGX [14], PLATON [15] O O NH2 F N F O Scheme 1. Synthesis of the title compound. In the solution phase, refinement was carried out with the program SHELXL-97 [11,12], which uses the full matrix least squares method to determine the positions of atoms other than hydrogen. In the first stage of the purification, isotropic purification was performed to make the atom positions more sensitive and to identify the missing atoms. As a result of the purification, it was observed that there were no missing atoms except hydrogen and anisotropic purification was carried out. The melting point of the compound was measured with the Gallenkamp melting point apparatus. The synthesized solid form crystal was crushed into powder and formed into a disc with KBr, and FT-IR spectra were recorded in the range of 400- 4000 cm-1 with Bruker Vertex 80V FT-IR spectrometer (Ondokuz Mayıs University). 2.2. Synthesis 2-Ethoxy-1-naphthaldehyde and 4-fluoroaniline were obtained from Acros Organic and Aldrich Chemical Companies. N-((2-Ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline was prepared by refluxing at 350 K of a mixture of a solution containing 2-ethoxy-1-naphthaldehyde (20.0 mg, 0.1 mmol) in ethanol (20 mL) and a solution containing 4-fluoroaniline (11.1 mg, 0.1 mmol) in ethanol (20 mL) (Scheme 1). The prepared mixture was stirred for 5 hours to react. Crystals suitable for X- ray crystallographic analysis were obtained by slow evaporation of an ethanol solution of the title compound at room temperature for 3 days. Yield: 68%. M.p.: 75-79 °C. FTIR (KBr, ν, cm-1): 3520, 2980, 1702, 1676, 1625, 1523, 1446, 1370. 3. Results and discussion In this study, single crystal X-ray diffraction method was used to determine the molecular structure of N-((2- ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline compound (Figure 1). The crystallographic characteristics and the X-ray data collection and structure refinement parameters for the title compound are given in Table 1. The obtained geometrical parameters are given in Tables 2 and 3. The CN group in the molecule, the C=N double bond, has a strong electron-withdrawing effect. The presence of the C=N double bond in the molecule indicates that the enol-imine is in the tautomeric form [16]. The lengths of the C=N bonds in molecule A and B were measured as 1.265 (2) Å. The presence of single C-O bonds in the molecule also shows that the tautomer structure contains an imine form. The C-O bond (C17- O1 and C18-O1) lengths in molecules A and B were measured as 1.369(2), 1.428(2) and 1.360(2), 1.430(3) Å, respectively. The details obtained are compatible with similar structures reported in the literature [17,18]. Torsion angles τ1(N1A-C7A-C8A-C9A) and τ2(C3A-C4A- N1A-C7A) correspond to the tautomeric equivalents of the groups and these values are 19.2(3) and -134.38(18)°, respectively. These values show that the structure is not planar [19]. The packing of the crystal structure in the title compound is stabilized by intermolecular C-H···N, C-H···F hydrogen bonds and π-π stacking interactions (Figure 2). The molecular structure of the title compound contains intermolecular C-H···N and C-H···F hydrogen bonds (Table 4). 456 Atalay et al. / European Journal of Chemistry 12 (4) (2021) 454-458 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.454-458.2171 Table 2. Bond lengths for the title compound. Atom Atom Length (Å) Atom Atom Length (Å) Atom Atom Length (Å) Atom Atom Length (Å) C1A C2A 1.361(3) C4B C5B 1.373(2) C9A C10A 1.419(3) C14A C15A 1.405(3) C1A C6A 1.352(3) C4B N1B 1.423(2) C9A C14A 1.418(2) C14B C15B 1.398(3) C1A F1A 1.368(2) C5A C6A 1.378(3) C9B C10B 1.404(3) C15A C16A 1.347(3) C1B C2B 1.351(3) C5B C6B 1.377(2) C9B C14B 1.429(2) C15B C16B 1.335(3) C1B C6B 1.354(2) C7A C8A 1.459(2) C10A C11A 1.364(3) C16A C17A 1.407(3) C1B F1B 1.3667(18) C7A N1A 1.265(2) C10B C11B 1.360(3) C16B C17B 1.432(3) C2A C3A 1.379(3) C7B C8B 1.470(2) C11A C12A 1.396(4) C17A O1A 1.369(2) C2B C3B 1.374(3) C7B N1B 1.265(2) C11B C12B 1.395(3) C17B O1B 1.360(2) C3A C4A 1.385(2) C8A C9A 1.429(2) C12A C13A 1.337(3) C18A C19A 1.481(3) C3B C4B 1.380(2) C8A C17A 1.389(2) C12B C13B 1.342(3) C18A O1A 1.428(2) C4A C5A 1.381(2) C8B C9B 1.426(2) C13A C14A 1.416(3) C18B C19B 1.481(4) C4A N1A 1.415(2) C8B C17B 1.378(3) C13B C14B 1.412(3) C18B O1B 1.430(3) Table 3. Bond angles for the title compound. Atom Atom Atom Angle (°) Atom Atom Atom Angle (°) Atom Atom Atom Angle (°) C2A C1A F1A 117.9(2) C10B C9B C8B 124.26(17) C16A C15A C14A 122.4(2) C6A C1A C2A 123.2(2) C10B C9B C14B 116.51(19) C16B C15B C14B 122.8(2) C6A C1A F1A 118.9(2) C11A C10A C9A 120.6(2) C15A C16A C17A 119.3(2) C2B C1B C6B 122.84(18) C11B C10B C9B 122.3(2) C15B C16B C17B 119.3(2) C2B C1B F1B 118.83(17) C10A C11A C12A 121.5(3) C8A C17A C16A 121.7(2) C6B C1B F1B 118.32(18) C10B C11B C12B 120.6(3) O1A C17A C8A 116.31(16) C1A C2A C3A 118.3(2) C13A C12A C11A 119.6(3) O1A C17A C16A 121.96(18) C1B C2B C3B 118.49(19) C13B C12B C11B 119.4(3) C8B C17B C16B 120.9(2) C2A C3A C4A 120.3(2) C12A C13A C14A 121.3(3) O1B C17B C8B 116.39(19) C2B C3B C4B 120.8(2) C12B C13B C14B 121.8(2) O1B C17B C16B 122.6(2) C3A C4A N1A 118.62(17) C13A C14A C9A 119.9(2) O1A C18A C19A 107.94(19) C5A C4A C3A 119.16(18) C15A C14A C9A 118.7(2) O1B C18B C19B 107.1(3) C5A C4A N1A 122.20(17) C15A C14A C13A 121.4(2) C7A N1A C4A 117.81(16) C3B C4B N1B 123.33(17) C13B C14B C9B 119.3(2) C7B N1B C4B 118.31(15) C5B C4B C3B 118.71(17) C15B C14B C9B 118.6(2) C17A O1A C18A 120.06(15) C5B C4B N1B 117.92(15) C15B C14B C13B 122.1(2) C17B O1B C18B 120.4(2) C6A C5A C4A 120.5(2) C17B C8B C9B 119.09(18) N1B C7B C8B 124.82(18) C4B C5B C6B 120.77(18) C10A C9A C8A 123.41(18) C9A C8A C7A 124.60(17) C1A C6A C5A 118.5(2) C14A C9A C8A 119.53(17) C17A C8A C7A 116.97(18) C1B C6B C5B 118.39(19) C14A C9A C10A 117.1(2) C17A C8A C9A 118.41(16) N1A C7A C8A 126.4(2) C8B C9B C14B 119.23(19) C9B C8B C7B 124.38(18) Table 4. Hydrogen bonds for the title compound. D H A d(D-H) (Å) d(H-A) (Å) d(D-A) (Å) ∠ D-H-A (°) C18B H18C F1A 1 1.00(3) 2.44(3) 3.311(4) 145(2) C5B H5B N1B 2 0.968(17) 2.639(18) 3.603(2) 174.0(13) Symmetry codes: 1 -1+x, +y, -1+z; 2 -x, 1-y, -z. Figure 1. The molecular structure of the title compound. In addition, there is also C-H···π stacking interactions [C6B- H6B···Cg7 (C9B-C14B) H6B···Cg7: 2.72(2) Å, symmetry code: - x, 1-y, -z; C11-H11B···Cg3 (C9A-C14A) H11B···Cg3: 2.96(2) Å, symmetry code: 1-x, 1-y, -z] and C-F···π stacking interaction [C1B-F1B···Cg1 (C1A-C6A) F1B···Cg1: 4.1209(4) Å, symmetry code: -1+x, y, -1+z] exist in the molecule. 3.1. Hirshfeld surface analysis CrystalExplorer program was used for Hirshfeld surface analysis of the title molecule [20]. The dnorm surface is used to analyze and visualize the interactions between molecules and atoms in the studied structure. de and di distances are normalized distances. de is the distance from the outer surface of the nearest atom to the Van der Waals surface. di is the distance from the inner surface of the nearest atom. In addition, the white, blue, and red colors represented on the Hirshfeld surface in the dnorm map indicate that the interaction distances between atoms are equal, longer, or shorter than the Van der Waals surface [21, 22]. Figure 3 shows a 3D dnorm plot with normalized de and di interactions for the title compound. When the figure is examined, the bright red dots around the oxygen and hydrogen atoms represent donors and acceptors of the C- H···N interaction. Atalay et al. / European Journal of Chemistry 12 (4) (2021) 454-458 457 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.454-458.2171 Figure 2. Packing diagram of the title compound. dnorm de di Figure 3. Three-dimensional view of the Hirshfeld surface (dnorm, de, and di). H···H/H···H 49.3% C···H/H···C 30.8% F···H/H···F 11.9% N···H/H···N 3.2% Figure 4. Contribution of crystalline atom pairs to Hirshfeld surface and two-dimensional fingerprint drawings. In Figure 2, where two-dimensional fingerprint plots are shown (scattering points spread up to de = di = 1.5 Å), the dominant interaction of the analyzed compound originates from the H···H contacts, and these H···H contacts contribute to the Hirshfeld surface. It was calculated as 49.3%. Contribution from N···H/F···H contacts corresponding to the intermolecular interactions of C5-H5···N1 in the middle and C18-H18C··F1 at the far end (3.2% + 11.9% = 15.1%), in Figure 4. It is represented by a sharp spike formed as a pair. Other important interactions found in the molecule are C···H (30.8%) and O···H (2.5%) in percentile order. In addition, while there is a high probability that there are other identifiable contact points in the molecule that can be identified, their importance is likely to be of limited importance. Therefore, it is not be necessary to discuss or explain it in detail in this study [23,24]. 4. Conclusions A Schiff base compound, N-((2-ethoxynaphthalen-1-yl) methylene)-4-fluoroaniline, was synthesized by reacting 2- ethoxy-1-naphthaldehyde and 4-fluoroaniline. The structure of the compound was confirmed by X-ray crystallography. 458 Atalay et al. / European Journal of Chemistry 12 (4) (2021) 454-458 2021 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.12.4.454-458.2171 Compound that crystallizes in imine form in the triclinic P-1 Bravais lattice. C–H···F and C-H···N intermolecular hydrogen bonds determine the packing of the crystal structure. In the Hirshfeld calculations within the structure, the percentages of H···H, C···H, F···H, and N···H interactions were calculated as 49.3, 30.8, 11.9, and 3.2%, respectively. Supporting information CCDC-2100901 contains the supplementary crystallo- graphic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, 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 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. CRediT authorship contribution statement Conceptualization: Hakan Bulbul, Sehriman Atalay; Software: Hakan Bulbul, Sehriman Atalay; Validation: Sehriman Atalay; Formal Analysis: Mustafa Macit; Investigation: Sehriman Atalay; Resources: Mustafa Macit; Data Curation: Hakan Bulbul; Writing - Original Draft: Sehriman Atalay; Writing - Review and Editing: Hakan Bulbul; Visualization: Hakan Bulbul; Funding acquisition: Mustafa Macit; Supervision: Mustafa Macit; Project Administration: Mustafa Macit. ORCID Sehriman Atalay https://orcid.org/0000-0002-4175-3477 Mustafa Macit https://orcid.org/0000-0002-8512-9625 Hakan Bulbul https://orcid.org/0000-0002-8586-5075 References [1]. Jia, Y.; Li, J. Chem. Rev. 2015, 115 (3), 1597–1621. [2]. Rezaeivala, M.; Keypour, H. Coord. Chem. Rev. 2014, 280, 203–253. [3]. Qin, W.; Long, S.; Panunzio, M.; Biondi, S. Molecules 2013, 18 (10), 12264–12289. [4]. da Silva, C. M.; da Silva, D. L.; Modolo, L. V.; Alves, R. B.; de Resende, M. A.; Martins, C. V. 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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.ccdc.cam.ac.uk/data_request/cif mailto:data_request@ccdc.cam.ac.uk https://orcid.org/0000-0002-4175-3477 https://orcid.org/0000-0002-8512-9625 https://orcid.org/0000-0002-8586-5075 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms http://creativecommons.org/licenses/by-nc/4.0 http://www.eurjchem.com/index.php/eurjchem/pages/view/terms 1. Introduction 2. Experimental 2.1 Instrumentation 2.2. Synthesis 3. Results and discussion 3.1. Hirshfeld surface analysis 4. Conclusions Supporting information Disclosure statement CRediT authorship contribution statement ORCID References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: