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Vol. 32 No. 3 (2020): Vol 32 Issue 3

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Synthesis, Crystal Structure and Hirshfeld Surface Analysis of 3,14-Dimethyl-2,6,13,17-tetraazatricyclo(16.4.0.07,12)docosane-2-(nitric acid)

https://doi.org/10.14233/ajchem.2020.22506
Dohyun Moon
Beamline Department, Pohang Accelerator Laboratory, Pohang 37673, Republic of Korea
Sunghwan Jeon
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea
Keon Sang Ryoo
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea
Jong-Ha Choi
Department of Chemistry, Andong National University, Andong 36729, Republic of Korea

Corresponding Author(s) : Jong-Ha Choi

jhchoi@anu.ac.kr

Asian Journal of Chemistry, Vol. 32 No. 3 (2020): Vol 32 Issue 3

Abstract

The crystal structure of 3,14-dimethyl-2,6,13,17-tetraazatricyclo(16.4.0.07,12)docosane-2-(nitric acid), C20H40N4·2(NO2OH) had been determined using synchrotron radiation at 220 K. The compound crystallized in the space group P21/n of the monoclinic system with two mononuclear formula units in a cell of dimensions a = 9.1930(18), b = 10.120(2), c = 12.979(3) Å and β = 101.06(3)º. The asymmetric unit contains half a centrosymmetric macrocycle and one nitric acid molecule. There were two molecules in the unit cell. In structure of macrocycle, C-C and N-C bond lengths were in the range 1.5198(19) to 1.5367(18) Å and 1.4744(16) to 1.4986 (16) Å, respectively. The NO2OH group has one longer N-O bond of 1.3441(18) Å and two shorter N-O bond of 1.2509(19) Å and 1.2510(19) Å, and O-N-O angles of 126.31(14)º, 117.98(14)º and 115.71(14)º. The N-H···O and N-H···N hydrogen bonds interconnect macrocycle (C20H40N4) with nitric acid molecules while two O-H···O hydrogen bonds link the nitric acid molecule to neighboring nitric acid molecule each other. The molecule was stabilized by forming intermolecular N-H···O, N-H−N and O-H···O hydrogen bonds. Hirshfeld surface analysis by 3D molecular surface contours and 2D fingerprint plots have been used to analyze intermolecular interactions present in the crystal.

Keywords

Crystal structure Macrocycle Nitric acid Hydrogen bonds Synchrotron radiation Hirshfeld surface analysis
Moon, D., Jeon, S., Ryoo, K. S., & Choi, J.-H. (2020). Synthesis, Crystal Structure and Hirshfeld Surface Analysis of 3,14-Dimethyl-2,6,13,17-tetraazatricyclo(16.4.0.07,12)docosane-2-(nitric acid). Asian Journal of Chemistry, 32(3), 697–702. https://doi.org/10.14233/ajchem.2020.22506
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References
  1. G.C. Valks, G. McRobbie, E.A. Lewis, T.J. Hubin, T.M. Hunter, P.J. Sadler, C. Pannecouque, E. De Clercq and S.J. Archibald, J. Med. Chem., 49, 6162 (2006); https://doi.org/10.1021/jm0607810
  2. L. Ronconi and P.J. Sadler, Coord. Chem. Rev., 251, 1633 (2007); https://doi.org/10.1016/j.ccr.2006.11.017
  3. E. De Clercq, J. Med. Chem., 53, 1438 (2010); https://doi.org/10.1021/jm900932g
  4. J.-H. Choi, Inorg. Chim. Acta, 362, 4231 (2009); https://doi.org/10.1016/j.ica.2009.05.024
  5. M.A. Subhan, J.-H. Choi and S.W. Ng, Z. Anorg. Allg. Chem., 637, 2193 (2011); https://doi.org/10.1002/zaac.201100423
  6. J. Moncol, M. Mazúr, M. Valko, K.S. Ryoo and J.-H. Choi, J. Mol. Struct., 1202, 127224 (2020); https://doi.org/10.1016/j.molstruc.2019.127224
  7. J.-H. Choi, T. Suzuki and S. Kaizaki, Acta Crystallogr. E, 62, m2383 (2006); https://doi.org/10.1107/S1600536806034234
  8. J.-H. Choi, K.S. Ryoo and K.-M. Park, Acta Crystallogr. E, 63, m2674 (2007); https://doi.org/10.1107/S1600536807048039
  9. J.-H. Choi, T. Joshi and L. Spiccia, Z. Anorg. Allg. Chem., 638, 146 (2012); https://doi.org/10.1002/zaac.201100398
  10. J.-H. Choi, M.A. Subhan and S.W. Ng, Acta Crystallogr. E, 68, m190 (2012); https://doi.org/10.1107/S1600536812001845
  11. A. Ross, J.-H. Choi, T.M. Hunter, C. Pannecouque, S.A. Moggach, S. Parsons, E. De Clercq and P.J. Sadler, Dalton Trans., 41, 6408 (2012); https://doi.org/10.1039/c2dt30140g
  12. J.-H. Choi, M.A. Subhan, K.S. Ryoo and S.W. Ng, Acta Crystallogr. E, 68, o102 (2012); https://doi.org/10.1107/S160053681105272X
  13. F. White, P.J. Sadler and M. Melchart, CSD Communication CCDC 1408165 (2015).
  14. G.B. Richter-Addo, Acta Crystallogr. E, 74, 1039 (2018); https://doi.org/10.1107/S2059798318014997
  15. M.D. Moran, D.S. Brock, H.P.A. Mercier and G.J. Schrobilgen, J. Am. Chem. Soc., 132, 13823 (2010); https://doi.org/10.1021/ja105618w
  16. J.W. Shin, K. Eom and D. Moon, J. Synchrotron Rad., 23, 369 (2016); https://doi.org/10.1107/S1600577515021633
  17. Z. Otwinowski and W. Minor, eds., C.W. Carter Jr. and R.M. Sweet, Methods in Enzymology, Academic Press: New York, vol. 276, Macromolecular Crystallography, Part A, p. 307 (1997).
  18. G.M. Sheldrick, Acta Crystallogr. A, 71, 3 (2015); https://doi.org/10.1107/S2053273314026370
  19. K. Brandenburg and H. Putz, DIAMOND-3, University of Bonn, Bonn Germany (2014).
  20. D. Moon and J.-H. Choi, Acta Crystallogr. E, 74, 461 (2018); https://doi.org/10.1107/S2056989018003560
  21. M.A. Spackman and D. Jayatilaka, CrystEngComm, 11, 19 (2009); https://doi.org/10.1039/B818330A
  22. 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).
  23. M.A. Spackman and J.J. McKinnon, CrystEngComm, 4, 378 (2002); https://doi.org/10.1039/B203191B
  24. D. Moon, S. Tanaka, T. Akitsu and J.-H. Choi, J. Mol. Struct., 1154, 338 (2018); https://doi.org/10.1016/j.molstruc.2017.10.066.
  25. T. Aree, Y.P. Hong and J.-H. Choi, J. Mol. Struct., 1163, 86 (2018); https://doi.org/10.1016/j.molstruc.2018.02.102
  26. S. Jeon, J. Moncol, M. Mazúr, M. Valko and J.-H. Choi, Crystals, 9, 336 (2019); https://doi.org/10.3390/cryst9070336
  27. J. Moncol, M. Mazúr, M. Valko and J.-H. Choi, Acta Crystallogr. C, 75, 616 (2019); https://doi.org/10.1107/S2053229619005588
  28. J.J. McKinnon, D. Jayatilaka and M.A. Spackman, Chem. Commun., 3814 (2007); https://doi.org/10.1039/b704980c
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