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Crystal Structure of 2-(Ethoxymethylene)Malononitrile, Hirshfeld Surface Analysis and DFT Evaluation of the Non-covalent Interactions Energy

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Abstract

The presented study describe the crystal structure of 2-(Ethoxymethylene)malononitrile (1), C6H6N2O, in the monoclinic space group P21/m with Z = 2, a = 6.798(3), b = 6.172(3), c = 8.844(5) Å. The unit cell of a single crystal of 1 contains two antiparallel oriented molecules. Ethyl fragment demonstrates a disorder with equal occupancy values of 0.5 and a total site-occupation factor (s.o.f.) of 1.0. The molecules of 1 are linked into infinite chains of co-oriented molecules parallel to the a axis via N-H···N ≡ C close contacts with the distance of 2.494(3) Å. There are also weak hydrogen bonds > O···H- between the oxygen atom and the ethyl moiety. The estimation of the energy of non-covalent interactions was conducted by DFT method with different functionals. The best reproducibility of the geometric parameters of those interactions was obtained by using M06-2X functional. The estimated energy value was found to be − 1.20 kcal/mol.

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Scheme 1
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Data Availability

The structure of crystal 1 has been deposited in the Cambridge Crystallographic Data Centre with deposition number CCDC 2180335. These data can be obtained free of charge via https://www.ccdc.cam.ac.uk/structures/ (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033).

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Acknowledgements

This work was supported by the Russian Science Foundation (grant no. 24-23-00482 to VSG).

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Authors and Affiliations

  1. Institute of Chemistry, National Research Saratov State University, Saratov, 410012, Russian Federation

    Vyacheslav S. Grinev, Ilya A. Demeshko, Anna E. Sklyar & Alevtina Yu. Yegorova

  2. Institute of Biochemistry and Physiology of Plants and Microorganisms, Saratov Scientific Centre of the Russian Academy of Sciences, 13 Prospekt Entuziastov, Saratov, 410049, Russian Federation

    Vyacheslav S. Grinev

  3. Perm State National Research University, 15 Ulitsa Bukireva, Perm, 614068, Russian Federation

    Maksim V. Dmitriev

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Contributions

V.S.G. and I.A.D. wrote the main manuscript text, A.E.S. and M.V.D. prepared Figs. 1, 2, 3 and 4. A.Yu.Ye. supervised the work. All authors reviewed the manuscript.

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Correspondence to Vyacheslav S. Grinev.

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Grinev, V.S., Demeshko, I.A., Sklyar, A.E. et al. Crystal Structure of 2-(Ethoxymethylene)Malononitrile, Hirshfeld Surface Analysis and DFT Evaluation of the Non-covalent Interactions Energy. J Chem Crystallogr (2024). https://doi.org/10.1007/s10870-024-01019-0

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