Synthesis, crystal structure, and spectroscopic characterization of a new non-centrosymmetric compound, 1-(2-chloroquinolin-3-yl)-N-(4-fluorobenzyl)methanimine European Journal of Chemistry 15 (1) (2024) 25-30 European Journal of Chemistry ISSN 2153-2249 (Print) / ISSN 2153-2257 (Online) – Copyright © 2024 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.15.1.25-30.2491 European Journal of Chemistry View Journal Online View Article Online Synthesis, crystal structure, and spectroscopic characterization of a new non-centrosymmetric compound, 1-(2-chloroquinolin-3-yl)-N-(4-fluorobenzyl)methanimine Maha Hachicha 1, Rawia Nasri 2,*, Mohamed Faouzi Zid 2 and Hédi Mrabet 1 1 Laboratory of Selective and Heterocyclic Organic Synthesis, Faculty of Sciences of Tunis, University of Tunis El Manar, 2092 El Manar II, Tunis, Tunisia 2 Laboratory of Materials, Crystallochemistry and Applied Thermodynamics, Faculty of Sciences of Tunis, University of Tunis El Manar, 2092 El Manar II, Tunis, Tunisia * Corresponding author at: Laboratory of Materials, Crystallochemistry and Applied Thermodynamics, Faculty of Sciences of Tunis, University of Tunis El Manar, 2092 El Manar II, Tunis, Tunisia. e-mail: rawia.nasri@fst.utm.tn (R. Nasri). 10.5155/eurjchem.15.1.25-30.2491 Received: 29 October 2023 Received in revised form: 12 December 2023 Accepted: 26 December 2023 Published online: 31 March 2024 Printed: 31 March 2024 In this work, we report the synthesis and characterization of a new condensed aromatic heterocycle (1-(2-chloroquinolin-3-yl)-N-(4-fluorobenzyl)methanimine) useful in various fields, mainly in medicinal and therapeutic chemistry, with interesting biological properties. Characterization of the title compound was carried out by 1H, 13C, 19F nuclear magnetic resonance and X-ray diffraction techniques. The crystal structure reveals that title compound crystallizes in the monoclinic system and crystal data for C17H12ClFN2: monoclinic, space group P21 (no. 4), a = 7.2253(10) Å, b = 5.7720(10) Å, c = 17.105(2) Å, β = 95.338(10)°, V = 710.26(18) Å3, Z = 2, T = 298(2) K, μ(MoKα) = 0.274 mm-1, Dcalc = 1.397 g/cm3, 5010 reflections measured (4.784° ≤ 2Θ ≤ 54.324°), 3160 unique (Rint = 0.0501, Rsigma = 0.0506) which were used in all calculations. The final R1 was 0.0339 (I > 2σ(I)) and wR2 was 0.0907 (all data). The obtained molecular structure has an antiparallel arrangement of the molecular unit leading to a one-dimensional framework. Synthesis Quinolines X-ray diffraction Crystal structure NMR spectroscopy Non-centrosymmetric Cite this: Eur. J. Chem. 2024, 15(1), 25-30 Journal website: www.eurjchem.com 1. Introduction Heterocyclic chemistry is an essential section of chemistry that offers powerful synthetic tools for the search for bio- logically active molecules. Indeed, the majority of biologically active compounds contain a heterocyclic profile, and, therefore, heterocyclic chemistry has taken on an important place in organic and inorganic synthesis. Heterocycles occupy a predo- minant place in the dye industry, pharmaceuticals, and their roles are constantly increasing in the field of plastics, agri- cultural chemicals, and various other sectors. The development of new methods to obtain heterocycles of biological active compounds is one of the main objectives of chemists. Quinoline derivatives have been studied as antibacterial, antifungal, antimycobacterial, antiviral, anti SARS-Cov-2 Target, anti- malarial, anticancer, antioxidant, anticonvulsant, analgesic, anti-inflammatory, anthelmintic and cardiovascular protective, in addition to being beneficial against diseases affecting the nervous system [1-9]. These compounds are also widely used for their optical properties [10]. The importance of quinoline derivatives in biological systems has encouraged researchers to use this molecular framework to develop new potential drugs. On these days, the discovery of new compounds of this family is becoming increasingly observed. We are interested in the synthesis of a new compound containing the quinoline nucleus with a highly sought-after pharmacological profile and an important area of interesting biological activity. In this study, we synthesized 1-(2-chloroquinolin-3-yl)-N-(4-fluorobenzyl) methanimine (3) by a Vilsmeier-Haack reaction and an aromatic nucleophilic addition. The structure of the compound (3) obtained was confirmed and analyzed using 1H, 13C, and 19F NMR spectroscopy and X-ray diffraction techniques. 2. Experimental 2.1. Instrumentation The melting points were measured with a Koffler hot- staged apparatus and were not corrected. 1H, 13C and 19F NMR spectra were recorded with CDCl3 as the solvent on a Bruker- 300 spectrometer. Chemical shifts δ are reported in ppm relative to TMS as an internal reference. ABSTRACT RESEARCH ARTICLE KEYWORDS https://dx.doi.org/10.5155/eurjchem.15.1.25-30.2491 https://www.eurjchem.com/ https://dx.doi.org/10.5155/eurjchem.15.1.25-30.2491 mailto:rawia.nasri@fst.utm.tn http://www.eurjchem.com/ https://crossmark.crossref.org/dialog/?doi=10.5155/eurjchem.15.1.25-30.2491&domain=pdf&date_stamp=2024-03-31 26 Hachicha et al. / European Journal of Chemistry 15 (1) (2024) 25-30 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.1.25-30.2491 NH2 O OO AcOH, ∆, 30 min N H O POCl3, DMF 0°C / 75°C N CHO Cl 1 2 Scheme 1. Synthesis of 2-chloro-3-formylquinoline (2). N Cl H O 2 F H2N + 3 - H2O Hj Hh Hg Hf He Hd Hc Hc Hb HbHa F N ClN AcOH Hj Scheme 2. Synthesis of 1-(2-chloroquinolin-3-yl)-N-(4-fluorobenzyl)methanimine (3). Scheme 3. Correlations observed on the HMBC spectrum for compound 3. The progress of the reactions was monitored by TLC. The purification of the synthesized products was performed by recrystallisation and column chromatography. 2.2. Synthesis 2.2.1. Synthesis of 2-chloro-3-formylquinoline To a solution of N-phenylacetamide (1) (5 mmoles, 1 equiv.) in dry DMF (15 mmoles, 2.5 equiv.) at 0 °C with stirring, POCl3 (60 mmoles, 7 equiv.) was added dropwise. The reaction mixture was then warmed to 75 °C. After stirring for 5 hours, the mixture was poured into crushed ice, stirred for 5 minutes, and the resulting solid was filtered, washed well with water, and dried. The compound was purified by recrystallisation from ethyl acetate (Scheme 1). Yield: 50%. M.p.: 150-152 °C. 1H NMR (300 MHz, CDCl3, δ, ppm): 10.5 (s, 1H, CHO), 8.8 (s, 1H, H-1), 8.1 (m, 1H, H-5), 8.0 (m, 1H, H-2), 7.9 (m, 1H, H-3), 7.7 (m, 1H, H-4). 13C NMR (75 MHz, CDCl3, δ, ppm): 189.0 (HC=O), 127.3-134.5 (Ar-C). 2.2.2. Synthesis of 1-(2-chloroquinolin-3-yl)-N-(4-fluoro benzyl)methanimine (3) A solution of 2-chloro-3-formylquinoline (2) (2.60 mmol, 1 equiv.) in methanol (10 mL) was added dropwise to 4- benzylaminefluorine (2.60 mmol, 1.0 equiv.) in the presence of a catalytic amount of acetic acid. The reaction mixture was then heated to 60 °C for 12 hours with stirring. After evaporation, the residue is dried and recrystallized from petroleum ether. (Scheme 2). Color: Yellow crystals. M.p.: 83-85 °C. Yield: 80%. 1H NMR (300 MHz, CDCl3, δ, ppm): 4.80 (s, 2H, Hj), 7.12 (s, 2H, Hc), 7.21 (s, 2H, Hb), 7.60 (s, 1H, Hf), 7.80 (s, 1H, Hg), 7.88 (s, 1H, Hh), 7.92 (s, 1H, He), 8.71 (s, 1H, Hd), 8.8 (s, 1H, Ha). 13C NMR (75 MHz, CDCl3, δ, ppm): 160.8 (HC=N), 121.1-161.5 (Ar-C), 64.5 (CH2-N). 19F NMR (282 MHz, CDCl3, δ, ppm): -115.35. 2.3. X-ray diffraction study A yellow single crystal of compound 3 was selected and used for X-ray diffraction experiment. Intensity data were collected using an Enraf-Nonius CAD-4 diffractometer equipped with graphite monochromatic MoKα (λ = 0.71073 Å). Data reduction was processed with XCAD4 [11] included in the WINGX software package [12]. The structure was solved by direct method using the SHELXS-97 program [13] and refinements were performed by the full matrix least squares technique on all (F2) data using the program SHELXL-2014 [14]. Correction by psi-scan absorption was achieved [15]. All non- hydrogen atoms were refined with anisotropic atomic displacement parameters and refined against F2 data using the SHELXS-97 program [13]. All hydrogen atoms were fixed using the HFIX instruction authorized by SHELXL-2014 [14]. The structure representation was prepared using DIAMOND 3.1 [16]. Crystal data for compound 3 are summarized in Table 1. Hachicha et al. / European Journal of Chemistry 15 (1) (2024) 25-30 27 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.1.25-30.2491 Table 1. Crystal data and structure refinement for the title compound. Empirical formula C17H12ClFN2 Formula weight (g/mol) 298.74 Temperature (K) 298(2) Crystal system Monoclinic Space group P21 a, (Å) 7.2253(10) b, (Å) 5.7720(10) c, (Å) 17.105(2) β (°) 95.338(10) Volume (Å3) 710.26(18) Z 2 ρcalc (g/cm3) 1.397 μ (mm-1) 0.274 F(000) 308.0 Crystal size (mm3) 0.35 × 0.29 × 0.25 Radiation MoKα (λ = 0.71073) 2Θ range for data collection (°) 4.784 to 54.324 Index ranges -9 ≤ h ≤ 4, -7 ≤ k ≤ 7, -21 ≤ l ≤ 21 Reflections collected 5010 Independent reflections 3160 [Rint = 0.0501, Rsigma = 0.0506] Data/restraints/parameters 3160/1/239 Goodness-of-fit on F2 1.038 Final R indexes [I≥2σ (I)] R1 = 0.0339, wR2 = 0.0851 Final R indexes [all data] R1 = 0.0432, wR2 = 0.0907 Largest diff. peak/hole (e.Å-3) 0.24/-0.13 Flack parameter 0.02(4) CCDC number 2091684 Figure 1. Spectrum HMBC in CDCl3 of compound 3. Figure 2. The asymmetric unit of compound 3. 3. Results and discussion 3.1. Synthesis The required acetanilide (1) was readily prepared from the reaction of the corresponding aniline with acetic anhydride in acetic acid. Vilsmeier cyclization of acetanilide (1) was carried out by adding POCl3 to the substrate in DMF at 0 ° C followed by heating to 75 ° C to obtain 2-chloro-3-formylquinoline (2) with good yield [1] (Scheme 1). The chemical shifts and scalar coupling constants of the different types of protons and carbon of compound 2 are given in the experimental part. To access the desired compound 3, we react p-fluoro- benzylamine with quinoline 2 in the presence of a few drops of acetic acid in methanol, which allowed us to isolate a functionalized quinoline 3 (Scheme 2). Identification of this product was performed by 1D and 2D NMR (1H, 13C, HMBC). In particular, a detailed study of the HMBC spectrum unambiguously confirms the structure of compound 3 (Figure 1). On the HMBC spectrum, we observed the presence of a heteronuclear correlation between the protons of the CH2 unit in the benzyl group and the imine carbon (Scheme 3). No correlation was observed between the carbon that carries the chlorine atom and the CH2 of the benzyl group. 28 Hachicha et al. / European Journal of Chemistry 15 (1) (2024) 25-30 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.1.25-30.2491 Table 2. Bond lengths, bond angles and torsion angles for the title compound. Atom Atom Length (Å) Atom Atom Length (Å) C1 N1 1.257(3) C5 C6 1.354(5) C1 C2 1.470(4) C6 C7 1.413(5) Cl1 C10 1.749(3) C7 C8 1.346(5) F1 C15 1.364(3) C8 C9 1.414(4) N1 C11 1.450(4) C11 C12 1.511(4) C2 C3 1.369(4) C12 C13 1.391(4) C2 C10 1.420(3) C12 C17 1.387(4) N2 C9 1.370(3) C13 C14 1.378(4) N2 C10 1.294(4) C14 C15 1.367(4) C3 C4 1.402(4) C15 C16 1.366(4) C4 C5 1.410(4) C16 C17 1.384(4) C4 C9 1.418(3) Atom Atom Atom Angle (°) Atom Atom Atom Angle (°) N1 C1 C2 120.8(2) C8 C9 C4 118.9(2) C1 N1 C11 117.7(2) C2 C10 Cl1 118.5(2) C3 C2 C1 121.5(2) N2 C10 Cl1 115.20(19) C3 C2 C10 115.7(2) N2 C10 C2 126.3(2) C10 C2 C1 122.8(2) N1 C11 C12 111.5(2) C10 N2 C9 117.3(2) C13 C12 C11 119.7(2) C2 C3 C4 121.5(2) C17 C12 C11 122.0(2) C3 C4 C5 124.0(2) C17 C12 C13 118.3(2) C3 C4 C9 117.0(2) C14 C13 C12 121.6(3) C5 C4 C9 119.0(2) C15 C14 C13 118.0(3) C6 C5 C4 120.6(3) F1 C15 C14 119.2(3) C5 C6 C7 120.2(3) F1 C15 C16 118.1(3) C8 C7 C6 120.9(3) C16 C15 C14 122.7(3) C7 C8 C9 120.4(3) C15 C16 C17 118.7(3) N2 C9 C4 122.2(2) C16 C17 C12 120.7(2) N2 C9 C8 118.9(2) A B C D Angle (°) A B C D Angle (°) C1 N1 C11 C12 -118.2(3) C5 C6 C7 C8 0.3(5) C1 C2 C3 C4 178.0(2) C6 C7 C8 C9 0.0(5) C1 C2 C10 Cl1 1.6(3) C7 C8 C9 N2 -179.7(3) C1 C2 C10 N2 -178.4(2) C7 C8 C9 C4 -0.3(4) F1 C15 C16 C17 178.7(2) C9 N2 C10 Cl1 -179.52(18) N1 C1 C2 C3 13.7(4) C9 N2 C10 C2 0.5(4) N1 C1 C2 C10 -167.9(2) C9 C4 C5 C6 -0.1(4) N1 C11 C12 C13 -156.8(2) C10 C2 C3 C4 -0.5(3) N1 C11 C12 C17 23.2(4) C10 N2 C9 C4 -0.7(3) C2 C1 N1 C11 -179.3(2) C10 N2 C9 C8 178.6(2) C2 C3 C4 C5 -179.0(2) C11 C12 C13 C14 -179.7(3) C2 C3 C4 C9 0.3(3) C11 C12 C17 C16 -179.9(3) C3 C2 C10 Cl1 -179.87(18) C12 C13 C14 C15 -0.8(4) C3 C2 C10 N2 0.1(4) C13 C12 C17 C16 0.1(4) C3 C4 C5 C6 179.2(3) C13 C14 C15 F1 -178.3(2) C3 C4 C9 N2 0.4(3) C13 C14 C15 C16 0.9(4) C3 C4 C9 C8 -179.0(2) C14 C15 C16 C17 -0.6(4) C4 C5 C6 C7 -0.2(5) C15 C16 C17 C12 0.0(4) C5 C4 C9 N2 179.7(2) C17 C12 C13 C14 0.3(4) C5 C4 C9 C8 0.4(4) 3.2. Crystal structure The crystal structure determination reveals that compound 3 (C17H12ClFN2) crystallizes in the monoclinic system with the P21 space group. The lattices parameters are a = 7.2253(10) Å, b = 5.7720(10) Å, c = 17.105(2) Å, β = 95.338(10)°. Single- crystal XRD analysis shows that the formula unit of C17H12ClFN2 consists of two aromatic rings that contain an N and Cl atom linked to another aromatic ring, which contains an F atom (Figure 2). The structure of the title compound can be described by the antiparallel arrangement of the molecular units (Figure 3). In this structure, the double bonds C-N in the imine functions: C10- N2 and C1-N1 are 1.294(4) and 1.257(3) Å, respectively. The average of the C-C bond distances in the aromatic ring is equal to 1.419(3) Å. Furthermore, the values of C15-F1 and C10-Cl1 are 1.364(3) and 1.749(3) Å, respectively (Table 2). These values are consistent with those reported in the literature [17- 20]. Intramolecular interactions determine the supramolecular structure of the title compound (Table 3). Noncovalent interactions between hydrocarbons (C–H⋅⋅⋅π interaction) and aromatic ring (Cg(3)) form one-dimensional framework in compound 3, and play an essential role in maintaining the stability of the crystal (Figure 4). Figure 3. Projection of the structure of compound 3 along b direction. Hachicha et al. / European Journal of Chemistry 15 (1) (2024) 25-30 29 2024 – European Journal of Chemistry – CC BY NC – DOI: 10.5155/eurjchem.15.1.25-30.2491 Table 3. Intramolecular hydrogen bonding interactions and the geometric parameters of C–H⋅⋅⋅π contact for title compound. Donor-H···Acceptor D-H, Å H···A, Å D···A, Å D-H···A, ° C(1)-H(1)···Cl(1) 0.93(3) 2.69(3) 3.066(2) 105(2) C(3)-H(3)···N(1) 0.94(3) 2.53(3) 2.844(4) 100(2) X--H(I)···Cg(J) X-H, Å H···Cg, Å X···Cg, Å X-H···Cg , ° H-Perp, Å γ, ° Symmetry C(13)-H(13)···Cg(3) * 0.92(3) 2.78(3) 3.452(3) 132(2) 2.75 7.99 1-x,1/2+y,1-z * Cg(3): C12-C17 ring. Figure 4. C–H⋅⋅⋅π contact for title compound. 4. Conclusions 1-(2-Chloroquinolin-3-yl)-N-(4-fluorobenzyl)methanimine (3) was successfully synthesized in three steps and the compound obtained was characterized by 1H, 13C and 19F NMR techniques. In addition, the obtained molecular structure by the single crystal X-ray diffraction study of the title compound confirms the suggested molecular structure. The obtained molecular structure has an antiparallel arrangement of the molecular unit leading to a one-dimensional framework. Acknowledgements Financial support from the Ministry of Higher Education and Scientific Research of Tunisia is appreciated. Supporting information CCDC-2091684 contains the supplementary crystallographic data for this article. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ data_request/cif, or by emailing data_request@ccdc.cam.ac.uk, or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44(0)1223-336033. Disclosure statement Conflict of interest: The authors declare that they have no conflict of interest. Ethical approval: All ethical guidelines have been adhered. Sample availability: A sample of the compound is available from the author. CRediT authorship contribution statement Conceptualization: Rawia Nasri, Maha Hachicha; Methodology: Rawia Nasri, Maha Hachicha; Validation: Rawia Nasri, Maha Hachicha; Mohamed Faouzi Zid; Hédi Mrabet; Formal Analysis: Rawia Nasri, Mohamed Faouzi Zid; Investigation: Rawia Nasri, Maha Hachicha; Mohamed Faouzi Zid; Data Curation: Rawia Nasri, Maha Hachicha; Writing - Original Draft: Rawia Nasri, Maha Hachicha; Writing - Review and Editing: Rawia Nasri, Maha Hachicha; Visualization: Rawia Nasri, Mohamed Faouzi Zid; Supervision: Mohamed Faouzi Zid, Hédi Mrabet; Project Administration: Ministry of Higher Education and Scientific Research of Tunisia. ORCID and Email Maha Hachicha hachicha19@gmail.com https://orcid.org/0009-0001-0988-5058 Rawia Nasri rawianasri11@gmail.com https://orcid.org/0000-0003-3844-5083 Mohamed Faouzi Zid mohamedfaouzi.zid@fst.utm.tn https://orcid.org/0000-0003-2061-853X Hédi Mrabet hedi.mrabet@fst.utm.tn https://orcid.org/0009-0003-7133-7815 References [1]. 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Synthesis, crystal structure, and antidiabetic property of hydrazine functionalized Schiff base: 1,2- Di(benzylidene)hydrazine. Eur. J. Chem. 2022, 13, 234–240. Copyright © 2024 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 https://www.eurjchem.com/index.php/eurjchem/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 (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry). https://www.eurjchem.com/index.php/eurjchem/terms http://creativecommons.org/licenses/by-nc/4.0 https://www.eurjchem.com/index.php/eurjchem/terms 1. Introduction 2. Experimental 2.1. Instrumentation 2.2. Synthesis 2.2.1. Synthesis of 2-chloro-3-formylquinoline 2.2.2. Synthesis of 1-(2-chloroquinolin-3-yl)-N-(4-fluoro benzyl)methanimine (3) 2.3. X-ray diffraction study 3. Results and discussion 3.1. Synthesis 3.2. Crystal structure 4. Conclusions Acknowledgements Supporting information Disclosure statement CRediT authorship contribution statement ORCID and Email References PrintField10: PrintField11: PrintField12: PrintField13: PrintField14: PrintField15: PrintField20: PrintField21: PrintField22: PrintField23: PrintField24: PrintField25: