Abstract
Two packing polymorphs of 5-hydroxy-1-(4-methylbenzyl)-3-chloro-4-[(4-chlorophenyl)sulfanyl]-1,5-dihydro-2H-pyrrol-2-one are studied by single-crystal and powder X-ray diffraction, IR spectroscopy, and differential scanning calorimetry. Classical hydrogen bonds and CL…O interactions have the fundamental importance for the formation of the supramolecular motif that is identical in both modifications. The difference relates to the packing of 2D layers which is “parallel” in the triclinic modification and of the “herringbone” type in the monoclinic modification. It is shown that close similarity between structural organizations of crystal lattices, which is typical of packing polymorphs, can be accompanied by significant differences between their energies as well as by a high potential barrier upon the transition from the metastable polymorph to its stable form.
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References
R. J. Davey and J. Garside. From Molecules to Crystallizers: An Introduction to Crystallization. Oxford University Press, 2000.
J. Bernstein. Polymorphism in Molecular Crystals. Oxford University Press, 2002.
W. Beckmann. Crystallization: Basic Concepts and Industrial Applications. Wiley-VCH Verlag GmbH & Co. KGaA, 2013.
T. L. Threlfall. Analyst, 1995, 120, 2435.
E. H. Lee. Asian J. Pharm. Sci., 2014, 9, 163.
A. Nangia. J. Indian Inst. Sci., 2007, 87, 133.
R. K. R. Jetti, R. Boese, J. A. R. P. Sarma, L. S. Reddy, P. Vishweshwar, and G. R. Desiraju. Angew. Chem., Int. Ed., 2003, 42, 1963.
M. Haisa, S. Kashino, and H. Maeda. Acta Crystallogr., Sect.B: Struct. Cryst. Cryst. Chem., 1974, 30, 2510.
M. Haisa, S. Kashino, R. Kawai, and H. Maeda. Acta Crystallogr. B Struct. Cryst. Cryst. Chem., 1976, 32, 1283.
K. Fucke, N. Qureshi, D. S. Yufit, J. A. K. Howard, and J. W. Steed. Cryst. Growth Des., 2010, 10, 880.
Y. Park, S. X. M. Boerrigter, J. Yeon, S. H. Lee, S. K. Kang, and E. H. Lee. Cryst. Growth Des., 2016, 16, 2552.
A. A. Bredikhin, D. V. Zakharychev, Z. A. Bredikhina, A. T. Gubaidullin, and R. R. Fayzullin. CrystEngComm, 2012, 14, 211.
A. A. Bredikhin, D. V. Zakharychev, A. T. Gubaidullin, R. R. Fayzullin, A. I. Samigullina, and Z. A. Bredikhina. Cryst. Growth Des., 2018, 18, 3980.
V. A. Startseva, L. E. Nikitina, O. A. Lodochnikova, A. E. Klimovitskii, A. V. Aref’ev, N. P. Artemova, A. V. Bodrov, R. Z. Musin, and E. N. Klimovitskii. Phosphorus, Sulfur Silicon Relat. Elem., 2014, 189, 615.
O. A. Lodochnikova, D. B. Krivolapov, V. A. Startseva, L. E. Nikitina, A. V. Bodrov, N. P. Artemova, V. V. Klochkov, T. I. Madzhidov, G. A. Chmutova, and I. A. Litvinov. Phosphorus, Sulfur Silicon Relat. Elem., 2015, 190, 2222.
L. E. Nikitina, O. A. Lodochnikova, V. A. Startseva, A. V. Bodrov, N. P. Artemova, A. E. Klimovitskii, and V. V. Klochkov. Phosphorus, Sulfur Silicon Relat. Elem., 2017, 192, 187.
L. S. Kosolapova, A. R. Kurbangalieva, M. F. Valiev, O. A. Lodochnikova, E. A. Berdnikov, and G. A. Chmutova. Russ. Chem. Bull., 2013, 62, 456.
O. A. Lodochnikova, R. M. Khakimov, L. Z. Latypova, A. R. Kurbangalieva, and I. A. Litvinov. Russ. Chem. Bull., 2015, 64, 2444.
O. A. Lodochnikova, A. V. Bodrov, A. F. Saifina, L. E. Nikitina, and I. A. Litvinov. J. Struct. Chem., 2013, 54(1), 140.
R. R. Fayzullin, D. V. Zakharychev, A. T. Gubaidullin, O. A. Antonovich, D. B. Krivolapov, Z. A. Bredikhina, and A. A. Bredikhin. Cryst. Growth Des., 2017, 17, 271.
O. A. Lodochnikova, A. R. Zaripova, R. R. Fayzullin, A. I. Samigullina, I. I. Vandyukova, L. N. Potapova, and A. R. Kurbangalieva. CrystEngComm, 2018, 20, 3218.
O. A. Lodochnikova, L. S. Kosolapova, A. F. Saifina, A. T. Gubaidullin, R. R. Fayzullin, A. R. Khamatgalimov, I. A. Litvinov, and A. R. Kurbangalieva. CrystEngComm, 2017, 19, 7277.
L. Krause, R. Herbst-Irmer, G. M. Sheldrick, and D. Stalke. J. Appl. Cryst., 2015, 48, 3.
G. M. Sheldrick. Acta Crystallogr., Sect. A: Found. Adv., 2015, 71, 3.
G. M. Sheldrick. Acta Crystallogr., Sect. C: Struct. Chem., 2015, 71, 3.
L. J. Farrugia. J. Appl. Crystallogr., 2012, 45, 849.
J. P. M. Lommerse, A. J. Stone, R. Taylor, and F. H. Allen. J. Am. Chem. Soc., 1996, 118, 3108.
P. Cimino, M. Pavone, and V. Barone. J. Phys. Chem. A, 2007, 111, 8482.
K. E. Riley and P. Hobza. J. Chem. Theory Comput., 2008, 4, 232.
O. A. Lodochnikova, L. Z. Latypova, R. M. Khakimov, A. R. Kurbangalieva, D. B. Krivolapov, and I. A. Litvinov. J. Struct. Chem., 2013, 54, 213.
R. R. Fayzullin, S. A. Shteingolts, O. A. Lodochnikova, V. L. Mamedova, D. E. Korshin, and V. A. Mamedov. CrystEngComm, 2019, 21, 1587.
A. A. Bredikhin, D. V. Zakharychev, R. R. Fayzullin, O. A. Antonovich, A. V. Pashagin, and Z. A. Bredikhina. Tetrahedron: Asymmetry, 2013, 24, 807.
Funding
The physicochemical studies were conducted in the Assigned Spectral-Analytical Center of the Kazan Scientific Center, Russian Academy of Sciences. The work was financially supported by the Russian Science Foundation (grant No. 17-13-01209). The main compound was synthesized with the financial support of the Ministry of Education and Science of the Russian Federation according to the Russian Government Program of Competitive Growth of Kazan Federal University.
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Russian Text © The Author(s), 2020, published in Zhurnal Strukturnoi Khimii, 2020, Vol. 61, No. 3, pp. 498–510.
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Gerasimova, D.P., Saifina, A.F., Zakharychev, D.V. et al. Packing Polymorphism on the Example of 5-Hydroxy-1-(4-Methylbenzyl)-3-Chloro-4-[(4-Chlorophenyl)Sulfanyl]-1,5-Dihydro-2H-Pyrrol-2-One: A Crystallographic, Thermochemical, and Spectroscopic Study. J Struct Chem 61, 476–488 (2020). https://doi.org/10.1134/S0022476620030142
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DOI: https://doi.org/10.1134/S0022476620030142