European Journal of Chemistry

Crystal structure and computational studies of N-((2-ethoxynaphthalen-1-yl)methylene)-4-fluoroaniline

Crossmark


Main Article Content

Sehriman Atalay
Mustafa Macit
Hakan Bulbul

Abstract

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)°, = 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.


icon graph This Abstract was viewed 464 times | icon graph Article PDF downloaded 194 times icon graph Article CIF FILE downloaded 0 times

How to Cite
(1)
Atalay, S.; Macit, M.; Bulbul, H. Crystal Structure and Computational Studies of N-(2-Ethoxynaphthalen-1-yl)methylene)-4-Fluoroaniline. Eur. J. Chem. 2021, 12, 454-458.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Jia, Y.; Li, J. Chem. Rev. 2015, 115 (3), 1597-1621.
https://doi.org/10.1021/cr400559g

[2]. Rezaeivala, M.; Keypour, H. Coord. Chem. Rev. 2014, 280, 203-253.
https://doi.org/10.1016/j.ccr.2014.06.007

[3]. Qin, W.; Long, S.; Panunzio, M.; Biondi, S. Molecules 2013, 18 (10), 12264-12289.
https://doi.org/10.3390/molecules181012264

[4]. da Silva, C. M.; da Silva, D. L.; Modolo, L. V.; Alves, R. B.; de Resende, M. A.; Martins, C. V. B.; de Fátima, Â. J. Adv. Res. 2011, 2 (1), 1-8.
https://doi.org/10.1016/j.jare.2010.05.004

[5]. Malik, M. A.; Dar, O. A.; Gull, P.; Wani, M. Y.; Hashmi, A. A. Medchemcomm 2018, 9 (3), 409-436.
https://doi.org/10.1039/C7MD00526A

[6]. Nair, M. S.; Arish, D.; Joseyphus, R. S. J. Saudi Chem. Soc. 2012, 16 (1), 83-88.
https://doi.org/10.1016/j.jscs.2010.11.002

[7]. Tamer, Ö.; Dege, N.; Demirtaş, G.; Avcı, D.; Atalay, Y.; Macit, M.; Ağar, A. A. Spectrochim. Acta A Mol. Biomol. Spectrosc. 2014, 117, 13-23.
https://doi.org/10.1016/j.saa.2013.07.098

[8]. Ekennia, A. C.; Osowole, A. A.; Olasunkanmi, L. O.; Onwudiwe, D. C.; Ebenso, E. E. Res. Chem. Intermed. 2017, 43 (7), 3787-3811.
https://doi.org/10.1007/s11164-016-2841-z

[9]. Shrivastava, S. K.; Srivastava, P.; Upendra, T. V. R.; Tripathi, P. N.; Sinha, S. K. Bioorg. Med. Chem. 2017, 25 (4), 1471-1480.
https://doi.org/10.1016/j.bmc.2017.01.010

[10]. Carocho, M.; Ferreira, I. C. F. R. Food Chem. Toxicol. 2013, 51, 15-25.
https://doi.org/10.1016/j.fct.2012.09.021

[11]. Sheldrick, G. M. Acta Crystallogr. A 2008, 64 (Pt 1), 112-122.
https://doi.org/10.1107/S0108767307043930

[12]. Sheldrick, G. M. Acta Crystallogr. C Struct. Chem. 2015, 71 (Pt 1), 3-11.
https://doi.org/10.1107/S2053229614024218

[13]. Stoe&Cie, X-AREA (Version 1.18) and X-RED32 (Version 1.04), Stoe&Cie, Darmstadt, Germany, 2002.

[14]. Farrugia, L. J. J. Appl. Crystallogr. 2012, 45 (4), 849-854.
https://doi.org/10.1107/S0021889812029111

[15]. Spek, A. L. Acta Crystallogr. D Biol. Crystallogr. 2009, 65 (Pt 2), 148-155.
https://doi.org/10.1107/S090744490804362X

[16]. Ünver, H.; Yıldız, M.; Kiraz, A.; İskeleli, N. O.; Erdönmez, A.; Dülger, B.; Durlu, T. N. J. Chem. Crystallogr. 2006, 36 (3), 229-237.
https://doi.org/10.1007/s10870-005-9053-5

[17]. Bülbül, H.; Köysal, Y.; Macit, M.; Yaman, R.; Dege, N. Z. Krist. - New Cryst. Struct. 2017, 232 (1), 135-136.
https://doi.org/10.1515/ncrs-2016-0191

[18]. Ceylan, U.; Gümüş, S.; Ağar, E.; Soylu, M. S. Acta Crystallogr. Sect. E Struct. Rep. Online 2012, 68 (Pt 7), o2116.
https://doi.org/10.1107/S1600536812026062

[19]. Ünver, H.; Boyacıoğlu, B.; Zeyrek, C. T.; Yıldız, M.; Demir, N.; Yıldırım, N.; Karaosmanoğlu, O.; Sivas, H.; Elmalı, A. J. Mol. Struct. 2016, 1125, 162-176.
https://doi.org/10.1016/j.molstruc.2016.06.058

[20]. Spackman, P. R.; Turner, M. J.; McKinnon, J. J.; Wolff, S. K.; Grimwood, D. J.; Jayatilaka, D.; Spackman, M. A. J. Appl. Crystallogr. 2021, 54 (Pt 3), 1006-1011.
https://doi.org/10.1107/S1600576721002910

[21]. Demir Kanmazalp, S.; Dogan, O. E.; Dege, N.; Agar, E.; Bulbul, H.; Golenya, I. A. Acta Crystallogr. E Crystallogr. Commun. 2019, 75 (4), 470-474.
https://doi.org/10.1107/S2056989019003220

[22]. Sen, P.; Kansiz, S.; Dege, N.; Iskenderov, T. S.; Yildiz, S. Z. Acta Crystallogr. E Crystallogr. Commun. 2018, 74 (7), 994-997.
https://doi.org/10.1107/S2056989018008745

[23]. Gümüş, M. K.; Kansız, S.; Aydemir, E.; Gorobets, N. Y.; Dege, N. J. Mol. Struct. 2018, 1168, 280-290.

[24]. Kansız, S.; Dege, N. J. Mol. Struct. 2018, 1173, 42-51.
https://doi.org/10.1016/j.molstruc.2018.06.071

Supporting Agencies

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

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).