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COMPARISON OF DIFFERENT COMPUTATIONAL APPROACHES FOR UNVEILING THE HIGH-PRESSURE BEHAVIOR OF ORGANIC CRYSTALS AT A MOLECULAR LEVEL. CASE STUDY OF TOLAZAMIDE POLYMORPHS

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Abstract

The study of the high-pressure behavior of molecular crystals helps find limits of their stability, as well as obtain previously unknown new phases. This may result in the creation of new materials and their forms for a variety of applications: pharmaceutics, optoelectronics, etc. Nevertheless, until recently, there was no practical unified scheme for high-pressure studies of organic molecules, paying close attention to various inter- and intramolecular interactions. In this work, we compare different computational methods for the high-pressure research of molecular crystals in terms of the energy of particular interactions. Tolazamide polymorphs are taken as a representative system. It is shown that not only “structure-forming” interactions, e.g. H-bonds and stacking interactions, but also multiple van der Waals interactions should be taken into account. Moreover, we compare two different concepts for studying particular H-bonds in terms of absolute and relative energies, showing their importance in understanding the high-pressure behavior of tolazamide polymorphs. Finally, several important details about the high-pressure research of organic crystals at a molecular level by computational methods are formulated.

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REFERENCES

  1. J. Bernstein. Polymorphism in Molecular Crystals. Vol. 14. Oxford University Press: New York, 2002.

  2. A. J. Cruz-Cabeza, S. M. Reutzel-Edens, and J. Bernstein. Chem. Soc. Rev., 2015, 44, 8619–8635.

  3. L. McGregor, D. A. Rychkov, P. L. Coster, S. Day, V. A. Drebushchak, A. F. Achkasov, G. S. Nichol, C. R. Pulham, and E. V. Boldyreva. CrystEngComm, 2015, 17, 6183–6192.

  4. V. A. Drebushchak, L. McGregor, and D. A. Rychkov. J. Therm. Anal. Calorim., 2017, 127, 1807–1814.

  5. E. S. Vikulova, K. V. Zherikova, D. A. Piryazev, I. V. Korol′kov, N. B. Morozova, and I. K. Igumenov. J. Struct. Chem., 2017, 58(8), 1681–1684.

  6. A. Ramazani, H. Ahankar, K. Ślepokura, T. Lis, and S. W. Joo. J. Struct. Chem., 2019, 60(4), 662–670.

  7. D. P. Gerasimova, A. F. Saifina, D. V. Zakharychev, I. I. Vandyukova, P. P. Faizulin, A. R. Kurbangalieva, and O. A. Lodochnikova. J. Struct. Chem., 2020, 61(3), 476.

  8. Y. Liu, B. Gabriele, R. J. Davey, and A. J. Cruz-Cabeza. J. Am. Chem. Soc., 2020, jacs.0c00321.

  9. I. Orgzall, F. Emmerling, B. Schulz, and O. Franco. J. Phys. Condens. Matter, 2008, 20, 295206.

  10. B. A. Zakharov and E. V. Boldyreva. CrystEngComm, 2019, 21, 10–22.

  11. C. R. Groom, I. J. Bruno, M. P. Lightfoot, and S. C. Ward, Acta Crystallogr., Sect. B, 2016, 72, 171–179.

  12. Y. V. Seryotkin, T. N. Drebushchak, and E. V. Boldyreva. Acta Crystallogr., Sect. B, 2013, 69, 77–85.

  13. X. D. Wen, R. Hoffmann, and N. W. Ashcroft. J. Am. Chem. Soc., 2011, 133, 9023–9035.

  14. S. Block, C. E. Weir, and G. J. Piermarini. Science, 1970, 169, 586–587.

  15. F. P. A. Fabbiani, D. R. Allan, W. I. F. David, S. A. Moggach, S. Parsons, and C. R. Pulham. CrystEngComm, 2004, 6, 504–511.

  16. S. J. Smith, M. M. Bishop, J. M. Montgomery, T. P. Hamilton, and Y. K. Vohra. J. Phys. Chem. A, 2014, 118, 6068–6077.

  17. M. A. Neumann, J. van de Streek, F. P. A. Fabbiani, P. Hidber, and O. Grassmann. Nat. Commun., 2015, 6, 7793.

  18. R. D. L. Johnstone, A. R. Lennie, S. F. Parker, S. Parsons, E. Pidcock, P. R. Richardson, J. E. Warren, and P. A. Wood. CrystEngComm, 2010, 12, 1065.

  19. D. A. Rychkov. Crystals, 2020, 10, 81.

  20. D. A. Rychkov, J. Stare, and E. V. Boldyreva. Phys. Chem. Chem. Phys., 2017, 19, 6671–6676.

  21. P. A. Wood, D. Francis, W. G. Marshall, S. A. Moggach, S. Parsons, E. Pidcock, and A. L. Rohl. CrystEngComm, 2008, 10, 1154.

  22. L. B. Munday, P. W. Chung, B. M. Rice, and S. D. Solares. J. Phys. Chem. B, 2011, 115, 4378–4386.

  23. N. Giordano, C. M. Beavers, K. V. Kamenev, W. G. Marshall, S. A. Moggach, S. D. Patterson, S. J. Teat, J. E. Warren, P. A. Wood, and S. Parsons. CrystEngComm, 2019, 21, 4444–4456.

  24. P. Kumar, M. K. Cabaj, and P. M. Dominiak. Crystals, 2019, 9, 668.

  25. Y. Gao and K. W. Olsen. J. Pharm. Sci., 2015, 104, 2132–2141.

  26. A. M. Hendriks, D. Schrijnders, N. Kleefstra, E. G. E. de Vries, H. J. G. Bilo, M. Jalving, and G. W. D. Landman. Eur. J. Pharmacol., 2019, 861, 172598.

  27. W. Lv, X. Wang, Q. Xu, and W. Lu. Curr. Top. Med. Chem., 2020, 20, 37–56.

  28. E. V. Boldyreva, S. G. Arkhipov, T. N. Drebushchak, V. A. Drebushchak, E. A. Losev, A. A. Matvienko, V. S. Minkov, D. A. Rychkov, Y. V. Seryotkin, J. Stare, B. A. Zakharova, and B. A. Zakharov. Chem. – Eur. J., 2015, 21, 15395–15404.

  29. A. Y. Fedorov, D. A. Rychkov, E. A. Losev, B. A. Zakharov, J. Stare, and E. V. Boldyreva. CrystEngComm, 2017, 19, 2243–2252.

  30. A. Y. Fedorov, D. A. Rychkov, E. A. Losev, T. N. Drebushchak, and E. V. Boldyreva. Acta Crystallogr. Sect. C, 2019, 75, 598–608.

  31. M. Karakaya, Y. Sert, M. Kürekçi, B. Eskiyurt, and Ç. Çırak. J. Mol. Struct., 2015, 1095, 87–95.

  32. M. J. Turner, J. J. McKinnon, S. K. Wolff, D. J. Grimwood, P. R. Spackman, D. Jayatilaka, and M. A. Spackman. CrystalExplorer17. University of Western Australia, 2017.

  33. D. Jayatilaka, D. J. Grimwood. In: Computational Science – ICCS 2003 / Eds. P. M. A. Sloot, D. Abramson, A. V. Bogdanov, Y. E. Gorbachev, J. J. Dongarra, and A. Y. Zomaya. Lecture Notes in Computer Science, vol. 2660. Springer: Berlin, Heidelberg, 2003, 142–151.

  34. M. J. Turner, S. Grabowsky, D. Jayatilaka, Berlin, Heidelberg: M. A. Spackman. J. Phys. Chem. Lett., 2014, 5, 4249–4255.

  35. C. F. Mackenzie, P. R. Spackman, D. Jayatilaka, Berlin, Heidelberg: M. A. Spackman. IUCrJ, 2017, 4, 575–587.

  36. M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J. A. Montgomery, Jr., J. E. Peralta, F. Ogliaro, M. Bearpark, J. J. Heyd, E. Brothers, K. N. Kudin, V. N. Staroverov, T. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman, D.J. Fox. Gaussian 09, Revision A.02. Gaussian, Inc.: Wallingford CT, 2016.

  37. Y. Zhao and D. G. Truhlar. Theor. Chem. Acc., 2008, 120, 215–241.

  38. M. Walker, A. J. A. Harvey, A. Sen, and C. E. H. Dessent. J. Phys. Chem. A, 2013, 117, 12590–12600.

  39. F. B. van Duijneveldt, J. G. C. M. van Duijneveldt-van de Rijdt, and J. H. van Lenthe. Chem. Rev., 1994, 94, 1873–1885.

  40. D. Rychkov, S. Arkhipov, and E. Boldyreva. Acta Crystallogr., Sect. B, 2016, 72, 160–163.

  41. C. Tantardini, S. G. Arkipov, K. A. Cherkashina, A. S. Kil′met′ev, and E. V. Boldyreva. Struct. Chem., 2018, 29, 1867–1874.

  42. S. G. Arkhipov, P. S. Sherin, A. S. Kiryutin, V. A. Lazarenko, and C. Tantardini. CrystEngComm, 2019, 21, 5392–5401.

  43. A. Y. Fedorov, T. N. Drebushchak, and C. Tantardini. Comput. Theor. Chem., 2019, 1157, 47–53.

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Funding

This work was supported by the Russian Science Foundation (http://rscf.ru/en/) (project 18-73-00154).

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Authors and Affiliations

  1. Novosibirsk State University, Novosibirsk, Russia

    A. Yu. Fedorov & D. A. Rychkov

  2. Institute of Solid State Chemistry and Mechanochemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    D. A. Rychkov

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Correspondence to D. A. Rychkov.

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Fedorov, A.Y., Rychkov, D.A. COMPARISON OF DIFFERENT COMPUTATIONAL APPROACHES FOR UNVEILING THE HIGH-PRESSURE BEHAVIOR OF ORGANIC CRYSTALS AT A MOLECULAR LEVEL. CASE STUDY OF TOLAZAMIDE POLYMORPHS. J Struct Chem 61, 1356–1366 (2020). https://doi.org/10.1134/S0022476620090024

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