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CONFORMATIONAL DUALISM OF DIPYRIDYL-SUBSTITUTED FORMAMIDINE

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Abstract

A new polymorph of the β-modification of N,N′-di(pyridin-2-yl)formamidine that is more thermodynamically stable than the known α-modification is obtained. The crystal of β-modification contains hydrogen bonded molecular dimers with a skewed geometry. Therefore, the space group is not centrosymmetric – P42. This geometry is a result of the molecular E-syn,syn conformation in crystals of the β-phase, which differs from the E-anti,syn conformation in the α-phase. The number of crystallographically non-equivalent molecules (8) in the β-modification is unusually large for organic compounds. The structure of the packing is analyzed, and it is shown that the centers of dimers follow the sites of a distorted body-centered cubic pseudo-lattice (Ат ≈ 10 Å, αт = 90°) with a 16 times decreased unit cell volume. Reasons for symmetry violations causing modulations are considered.

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REFERENCES

  1. Z. Guo, R. Huo, Y. Q. Tan, V. Blair, G. B. Deacon, and P. C. Junk. Coord. Chem. Rev., 2020, 415, 213232.

    Article  CAS  Google Scholar 

  2. G. B. Deacon, M. E. Hossain, P. C. Junk, and M. Salehisaki. Coord. Chem. Rev., 2017, 340, 247.

    Article  CAS  Google Scholar 

  3. F. T. Edelmann. Recent Progress in the Chemistry of Metal Amidinates and Guanidinates: Syntheses, Catalysis and Materials. In: Advances in Organometallic Chemistry / Eds. A. F. Hill and M. J. Fink. Academic Press, 2013, Vol. 61, 55.

  4. Y. Z. Ma, N. A. Pushkarevsky, T. S. Sukhikh, A. E. Galashov, A. G. Makarov, P. W. Roesky, and S. N. Konchenko. Eur. J. Inorg. Chem., 2018, 2018, 3388.

    Article  CAS  Google Scholar 

  5. A. Millet, C. Xue, E. Song, C. Turro, and K. R. Dunbar. Inorg. Chem., 2020, 59, 2255.

    Article  CAS  PubMed  Google Scholar 

  6. S. Bambirra, M. W. Bouwkamp, A. Meetsma, and B. Hessen. J. Am. Chem. Soc., 2004, 126, 9182.

    Article  CAS  PubMed  Google Scholar 

  7. R. M. Roberts. J. Org. Chem., 1949, 14, 277.

    Article  CAS  PubMed  Google Scholar 

  8. M. N. C. Soeiro, K. Werbovetz, D. W. Boykin, W. D. Wilson, M. Z. Wang, and A. Hemphill. Parasitology, 2013, 140, 929.

    Article  CAS  PubMed  Google Scholar 

  9. X. Nan, J. Zhang, H.-J. Li, R. Wu, S.-B. Fang, Z.-Z. Zhang, and Y.-C. Wu. Eur. J. Med. Chem., 2020, 200, 112470.

    Article  CAS  PubMed  Google Scholar 

  10. J. A. Schott, C.-L. Do-Thanh, S. M. Mahurin, Z. Tian, N. C. Onishi, D.-E. Jiang, and S. Dai. J. Membr. Sci., 2018, 565, 203.

    Article  CAS  Google Scholar 

  11. A. Calderón-Díaz, J. Arras, E. T. Miller, N. Bhuvanesh, C. D. McMillen, and M. Stollenz. Eur. J. Org. Chem., 2020, 2020, 3243.

    Article  CAS  Google Scholar 

  12. S. Preusser, P. R. W. Schönherr, H. Görls, S. Krieck, W. Imhof, and M. Westerhausen. J. Mol. Struct., 2020, 1205, 127622.

    Article  CAS  Google Scholar 

  13. S. Bulut and W. L. Queen. J. Org. Chem., 2018, 83, 3806.

    Article  CAS  PubMed  Google Scholar 

  14. M. L. Cole, P. C. Junk, and L. M. Louis. J. Chem. Soc., Dalton Trans., 2002, 3906.

  15. M. K. Rofouei, N. Sohrabi, M. Shamsipur, E. Fereyduni, S. Ayyappan, and N. Sundaraganesan. Spectrochim. Acta, Part A, 2010, 76, 182.

    Article  CAS  Google Scholar 

  16. M. Handa, T. Ikeue, Y. Harada, Y. Kimura, T. Nishimura, D. Yoshioka, and M. Mikuriya. X-ray Struct. Anal. Online, 2013, 29, 25.

    Article  Google Scholar 

  17. A. Petitjean, L. Xing, and R. Wang. CrystEngComm, 2010, 12, 1397.

    Article  CAS  Google Scholar 

  18. X. An, L. Jiang, Q. Li, W. Li, and J. Cheng. Spectrochim. Acta, Part A, 2015, 138, 195.

    Article  CAS  Google Scholar 

  19. L. Xing, C. Wiegert, and A. Petitjean. J. Org. Chem., 2009, 74, 9513.

    Article  CAS  PubMed  Google Scholar 

  20. W. Zhao, R. Wang, N. J. Mosey, and A. Petitjean. Org. Lett., 2011, 13, 5160.

    Article  CAS  PubMed  Google Scholar 

  21. C.-J. Wu, C.-W. Su, C.-W. Yeh, J.-D. Chen, and J.-C. Wang. Acta Crystallogr., Sect. E, 2009, 65, o536.

    Article  CAS  Google Scholar 

  22. H. Komber, H.-H. Limbach, F. Böhme, and C. Kunert. J. Am. Chem. Soc., 2002, 124, 11955.

    Article  CAS  PubMed  Google Scholar 

  23. Bruker Apex3 software suite: Apex3, SADABS-2016/2 and SAINT, version 2018.7-2. Bruker AXS Inc.: Madison, WI, 2017.

  24. G. Sheldrick. Acta Crystallogr., Sect. A, 2015, 71, 3.

    Article  Google Scholar 

  25. G. Sheldrick. Acta Crystallogr., Sect. C, 2015, 71, 3.

    Article  Google Scholar 

  26. O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard, and H. Puschmann. J. Appl. Crystallogr., 2009, 42, 339.

    Article  CAS  Google Scholar 

  27. A. V. Alexeev and S. A. Gromilov. J. Struct. Chem., 2010, 51(1), 156.

    Article  CAS  Google Scholar 

  28. A. V. Alexeev and S. A. Gromilov. J. Struct. Chem., 2010, 51(4), 744.

    Article  CAS  Google Scholar 

  29. C. Prescher and V. Prakapenka: DIOPTAS. A Program for Reduction of Two-Dimensional X-Ray Diffraction Data and Data Exploration. High Pressure Research, 2015, 35, 223-230.

    Article  CAS  Google Scholar 

  30. S. V. Borisov. J. Struct. Chem., 1986, 27(1), 164.

    Article  CAS  Google Scholar 

  31. S. A. Gromilov and S. V. Borisov. J. Struct. Chem., 2003, 44(4), 664.

    Article  CAS  Google Scholar 

  32. S. A. Gromilov, E. A. Bykova, and S. V. Borisov. Crystallogr. Report, 2011, 56, 947.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Nikolaev Institute of Inorganic Chemistry, Siberian Branch, Russian Academy of Sciences, Novosibirsk, Russia

    T. S. Sukhikh, D. S. Kolybalov, D. A. Bashirov, S. A. Gromilov & S. N. Konchenko

  2. Novosibirsk State University, Novosibirsk, Russia

    D. S. Kolybalov

Authors
  1. T. S. Sukhikh
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  2. D. S. Kolybalov
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  3. D. A. Bashirov
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  4. S. A. Gromilov
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  5. S. N. Konchenko
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Correspondence to T. S. Sukhikh.

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Russian Text © The Author(s), 2021, published in Zhurnal Strukturnoi Khimii, 2021, Vol. 62, No. 6, pp. 1035-1042.https://doi.org/10.26902/JSC_id74448

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Sukhikh, T.S., Kolybalov, D.S., Bashirov, D.A. et al. CONFORMATIONAL DUALISM OF DIPYRIDYL-SUBSTITUTED FORMAMIDINE. J Struct Chem 62, 966–973 (2021). https://doi.org/10.1134/S0022476621060160

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  • DOI: https://doi.org/10.1134/S0022476621060160

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