Рентгеноструктурное исследование структур 3,6-ди(пиридин-2-ил)-1,4-дигидро-1,2,4,5-тетразина и 1,2-бис(2-пиридилформимидоил)гидразина

P. Slepukhin; E. Ladin; A. Rybakova; A. Markina; A. Alekseeva; A. Yurtaeva; M. Eremeeva; A. Golovina; E. Shabunina; D. Kopchuk; G. Zyryanov

Authors

P. Slepukhin Ural Federal University
E. Ladin Ural Federal University
A. Rybakova South Ural State University
A. Markina Ural Federal University
A. Alekseeva Ural Federal University
A. Yurtaeva Ural Federal University
M. Eremeeva South Ural State University
A. Golovina I.Ya. Postovsky Insititute of Organic Synthesis of UB of the RAS
E. Shabunina Ural Federal University
D. Kopchuk Ural Federal University
G. Zyryanov Ural Federal University

Keywords:

dihydrotetrazines, pyridine derivatives, X-ray diffraction analysis, hydrogen bonds, supramolecular organization

Abstract

The structure of 3,6-bis(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine was studied by X-ray diffraction analysis. The data obtained were compared with previously reported crystalline forms of this com-pound. The tetrazine ring was shown to adopt a boat conformation, while the crystal structure is stabi-lized by a system of intra- and intermolecular N–H···N hydrogen bonds. The formation of intermo-lecular dimers and molecular stacks in the crystal was established. In addition, the structural and packing features of the accompanying reaction product, 1,2-bis(2-pyridylformimidoyl)hydrazine, were investigated. Its supramolecular organization was found to be governed by intra- and intermo-lecular hydrogen bonds assembling the molecules into chains.

Author Biographies

P. Slepukhin, Ural Federal University

The structure of 3,6-bis(pyridin-2-yl)-1,4-dihydro-1,2,4,5-tetrazine was studied by X-ray diffraction analysis. The data obtained were compared with previously reported crystalline forms of this compound. The tetrazine ring was shown to adopt a boat conformation, while the crystal structure is stabilized by a system of intra- and intermolecular N–H···N hydrogen bonds. The formation of intermolecular dimers and molecular stacks in the crystal was established. In addition, the structural and packing features of the accompanying reaction product, 1,2-bis(2-pyridylformimidoyl)hydrazine, were investigated. Its supramolecular organization was found to be governed by intra- and intermolecular hydrogen bonds assembling the molecules into chains.

E. Ladin, Ural Federal University

младший научный сотрудник кафедры органической и биомолекулярной химии ХТИ

A. Rybakova, South Ural State University

кандидат химических наук, доцент, доцент кафедры теоретической и прикладной химии

A. Markina, Ural Federal University

лаборант-исследователь лаборатории перспективных материалов, зеленых методов и биотехнологий НОиИЦ ХФТ ХТИ

A. Alekseeva, Ural Federal University

лаборант-исследователь лаборатории перспективных материалов, зеленых методов и биотехнологий НОиИЦ ХФТ ХТИ

A. Yurtaeva, Ural Federal University

инженер-исследователь кафедры органической и биомолекуляной химии ХТИ

M. Eremeeva, South Ural State University

студент 4-го курса бакалавриата по направлению 04.03.01 Химия, кафедра теоретической и прикладной химии

A. Golovina, I.Ya. Postovsky Insititute of Organic Synthesis of UB of the RAS

лаборант-исследователь Технологической лаборатории

E. Shabunina, Ural Federal University

студент 4-го курса бакалавриата Химико-технологического института

D. Kopchuk, Ural Federal University

доктор химических наук, старший научный сотрудник Лаборатории координационных соединений; профессор кафедры органической и биомолекулярной химии ХТИ

G. Zyryanov, Ural Federal University

доктор химических наук, профессор РАН, ведущий научный сотрудник лаборатории координационных соединений

References

1. Kaim W. Coord. Chem. Rev. 2002. V. 230, Is. 1–2. P. 127. DOI: 10.1016/S0010-8545(02)00044-9

2. Stetsiuk O., Abhervé A., Avarvari N. Dalton Trans. 2020. V. 49, Is. 18. P. 5759. DOI: 10.1039/D0DT00827C

3. Seth P., Bauzá A., Frontera A., et al. CrystEngComm. 2013. V. 15, Is. 15. P. 3031. DOI: 10.1039/c3ce00058c

4. Withersby M.A., Blake A.J., Champness N.R., et al. J. Am. Chem. Soc. 2000. V. 122, Is. 17. P. 4044. DOI: 10.1021/ja991698n

5. Withersby M.A., Blake A.J., Champness N.R. et al. Angew. Chem. Int. Ed. Engl. 1997. V. 36, Is. 21. P. 2327. DOI: 10.1002/anie.199723271

6. Li J., Peng Y., Liang H., et al. Eur. J. Inorg. Chem. 2011. V. 2011. Is. 17. P. 2712. DOI:10.1002/ejic.201100227

7. CrysAlisPro, version 1.171.39.38a, Data Collection, Reduction and Correction Program, Rigaku Oxford Diff raction, 2017.

8. Sheldrick G.M. Acta Crystallogr. A. 2015. V. A71. P. 3. DOI: 10.1107/S2053273314026370

9. Sheldrick G.M. Acta Cryst. 2008. A64. 112. DOI: 10.1107/S2053229614024218

10. Dolomanov O.V., Bourhis L.J., Gildea R.J., et al. J. Appl. Cryst. 2009. V. 42, Is. 2. P. 339. DOI: 10.1107/S0021889808042726

11. Caira M.R., Giles R.G.F., Nassimbeni L. R., et al. Acta Crystallogr. Sect. B: Struct. Crystal-logr. Cryst. Chem. 1976. V. 32. P. 1467. DOI: 10.1107/S0567740876005578

12. Bolte M., Wagner M., Ding L. CCDC 138693: Experimental Crystal Structure Determination, 2000, DOI: 10.5517/cc4n9z1

13. Liou L.S., Chen P.S., Sun C.H., et al. Acta Crystallogr., Sect. C: Cryst. Struct. Commun. 1996. V. 52, Is. 7. P. 1841. DOI: 10.1107/s0108270195016635

14. Kubota S., Kirino O., Koida Y. et al. J. Pharm. Soc. Jpn. 1972, V. 92. P. 275.

15. Armstrong J.A., Barnes J.C., Weakley T.J.R. Acta Crystallogr. C Cryst. Struct. Commun. 1998. Vol. 54, Is. 12. P. 1923. DOI: 10.1107/S0108270198008014.