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Volume 69 
Part 10 
Pages o1586-o1587  
October 2013  

Received 26 July 2013
Accepted 18 September 2013
Online 25 September 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.032
wR = 0.082
Data-to-parameter ratio = 19.6
Details
Open access

2-Amino-5-methyl-3-(2-oxo-2-phenylethyl)-7-phenyl-4,5,6,7-tetrahydro-3H-[1,2,4]triazolo[1,5-a]pyrimidin-8-ium bromide ethanol monosolvate

aSouth-Russia State Technical University, 346428 Novocherkassk, Russian Federation, and bA. N. Nesmeyanov Institute of Organoelement Compounds, 119991 Moscow, Russian Federation
Correspondence e-mail: chern13@yandex.ru

In the title compound, C20H22N5O+·Br-·C2H6O, the tetrahydropyrimidine ring of the bicyclic cation adopts a half-chair conformation with an equatorial orientation of the phenyl and methyl substituents. The amino group is nearly coplanar with the 1,2,4-triazole ring [interplanar angle = 4.08 (8)°] and has a slightly pyramidal configuration. The mean planes of the triazole ring and the benzene ring of the phenacyl group form a dihedral angle of 88.58 (7)°. In the crystal, N-H...Br, N-H...O and O-H...Br hydrogen bonds link the cations, anions and ethanol molecules into layers parallel to the bc plane.

Related literature

For the synthesis and reactivity of partially hydrogenated [1,2,4]triazolo[1,5-a]pyrimidines, see: Desenko (1995[Desenko, S. M. (1995). Chem. Heterocycl. Compd, 31, 125-136.]); Desenko et al. (1994[Desenko, S. M., Shishkin, O. V., Orlov, V. D., Lipson, V. V., Lindeman, S. V. & Struchkov, Yu. T. (1994). Chem. Heterocycl. Compd, 30, 851-855.]); Chebanov et al. (2008[Chebanov, V. A., Desenko, S. M. & Gurley, T. W. (2008). Azaheterocycles Based on ,-Unsaturated Carbonyls. Berlin: Springer.], 2010[Chebanov, V. A., Gura, K. A. & Desenko, S. M. (2010). Top. Heterocycl. Chem. 23, 41-84.]); Gorobets et al. (2012[Gorobets, N. Yu., Chebanov, V. A., Konovalova, I. S., Shishkin, O. V. & Desenko, S. M. (2012). RSC Adv. 2, 6719-6728.]); Lipson et al. (2012[Lipson, V. V., Svetlichnaya, N. V., Borodina, V. V., Shirobokova, M. G., Desenko, S. M., Musatov, V. I., Shishkina, S. V., Shishkin, O. V. & Zubatyuk, R. I. (2012). J. Heterocycl. Chem. 49, 1019-1025.]), Chernyshev et al. (2008a[Chernyshev, V. M., Khoroshkin, D. A., Sokolov, A. N., Taranushich, V. A., Gladkov, E. S., Shishkina, S. V., Shishkin, O. V. & Desenko, S. M. (2008a). J. Heterocycl. Chem. 45, 1419-1427.],b[Chernyshev, V. M., Sokolov, A. N., Khoroshkin, D. A. & Taranushich, V. A. (2008b). Russ. J. Org. Chem. 44, 715-722.]). For applications of partially hydrogenated triazolopyrimidines in the synthesis of polycondensed heterocycles, see: Beck et al. (2011[Beck, H. P., DeGraffenreid, M., Fox, B., Allen, J. G., Rew, Y., Schneider, S., Saiki, A. Y., Yu, D., Oliner, J. D., Salyers, K., Ye, Q. & Olson, S. (2011). Bioorg. Med. Chem. Lett. 21, 2752-2755.]); Lipson et al. (2006[Lipson, V. V., Desenko, S. M., Ignatenko, I. V., Shishkin, O. V. & Shishkina, S. V. (2006). Russ. Chem. Bull. 55, 345-350.]); Sidorenko & Orlov (2011[Sidorenko, D. Yu. & Orlov, V. D. (2011). Ultrason. Sonochem. 18, 300-302.]); Sokolov et al. (2011[Sokolov, A. N., Mischenko, M. S., Gladkov, E. S. & Chernyshev, V. M. (2011). Chem. Heterocycl. Compd, 47, 249-251.]). For structures of protonated C-amino-1,2,4-triazoles and quaternized derivatives of tetrahydrotriazolopyrimidines, see: Chernyshev et al. (2008a[Chernyshev, V. M., Khoroshkin, D. A., Sokolov, A. N., Taranushich, V. A., Gladkov, E. S., Shishkina, S. V., Shishkin, O. V. & Desenko, S. M. (2008a). J. Heterocycl. Chem. 45, 1419-1427.], 2010[Chernyshev, V. M., Astakhov, A. V., Ivanov, V. V. & Starikova, Z. A. (2010). Acta Cryst. E66, o1644-o1645.]); Matulkova et al. (2012[Matulkova, I., Cihelka, J., Pojarova, M., Fejfarova, K., Dusek, M., Vanek, P., Kroupa, J., Krupkova, R., Fabry, J. & Nemec, I. (2012). CrystEngComm, 14, 4625-4636.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the correlation of bond lengths with bond orders between the sp2 hybridized C and N atoms, see: Burke-Laing & Laing (1976[Burke-Laing, M. & Laing, M. (1976). Acta Cryst. B32, 3216-3224.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C20H22N5O+·Br-·C2H6O

  • Mr = 474.40

  • Monoclinic, P 21 /c

  • a = 10.7471 (13) Å

  • b = 13.3261 (16) Å

  • c = 15.5792 (19) Å

  • [beta] = 95.735 (2)°

  • V = 2220.0 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.88 mm-1

  • T = 120 K

  • 0.22 × 0.19 × 0.18 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.520, Tmax = 0.713

  • 31509 measured reflections

  • 5356 independent reflections

  • 4309 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](F2)] = 0.032

  • wR(F2) = 0.082

  • S = 1.01

  • 5356 reflections

  • 273 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.87 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H3N...Br1i 0.90 2.49 3.392 (2) 176
N5-H1N...O1S 0.90 1.94 2.839 (2) 176
N5-H2N...Br1ii 0.90 2.61 3.468 (2) 159
O1S-H1S...Br1 0.85 2.46 3.287 (2) 165
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2095 ).


Acknowledgements

This work was supported financially by the Ministry of Education and Science of Russia through the Federal Target Program "Research and Educational Personnel of Innovative Russia at 2009-2013 Years" (grant No. 14.B37.21.0827) and, in part, by the Russian Foundation for Basic Research (grant No. 13-03-00253).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Beck, H. P., DeGraffenreid, M., Fox, B., Allen, J. G., Rew, Y., Schneider, S., Saiki, A. Y., Yu, D., Oliner, J. D., Salyers, K., Ye, Q. & Olson, S. (2011). Bioorg. Med. Chem. Lett. 21, 2752-2755.  [CrossRef] [ChemPort] [PubMed]
Bruker (2008). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burke-Laing, M. & Laing, M. (1976). Acta Cryst. B32, 3216-3224.  [CSD] [CrossRef] [IUCr Journals] [Web of Science]
Chebanov, V. A., Desenko, S. M. & Gurley, T. W. (2008). Azaheterocycles Based on [alpha],[beta]-Unsaturated Carbonyls. Berlin: Springer.
Chebanov, V. A., Gura, K. A. & Desenko, S. M. (2010). Top. Heterocycl. Chem. 23, 41-84.  [CrossRef] [ChemPort]
Chernyshev, V. M., Astakhov, A. V., Ivanov, V. V. & Starikova, Z. A. (2010). Acta Cryst. E66, o1644-o1645.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Chernyshev, V. M., Khoroshkin, D. A., Sokolov, A. N., Taranushich, V. A., Gladkov, E. S., Shishkina, S. V., Shishkin, O. V. & Desenko, S. M. (2008a). J. Heterocycl. Chem. 45, 1419-1427.  [CSD] [CrossRef] [ChemPort]
Chernyshev, V. M., Sokolov, A. N., Khoroshkin, D. A. & Taranushich, V. A. (2008b). Russ. J. Org. Chem. 44, 715-722.  [Web of Science] [CrossRef] [ChemPort]
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Desenko, S. M. (1995). Chem. Heterocycl. Compd, 31, 125-136.  [CrossRef]
Desenko, S. M., Shishkin, O. V., Orlov, V. D., Lipson, V. V., Lindeman, S. V. & Struchkov, Yu. T. (1994). Chem. Heterocycl. Compd, 30, 851-855.  [CrossRef]
Gorobets, N. Yu., Chebanov, V. A., Konovalova, I. S., Shishkin, O. V. & Desenko, S. M. (2012). RSC Adv. 2, 6719-6728.
Lipson, V. V., Desenko, S. M., Ignatenko, I. V., Shishkin, O. V. & Shishkina, S. V. (2006). Russ. Chem. Bull. 55, 345-350.  [Web of Science] [CrossRef] [ChemPort]
Lipson, V. V., Svetlichnaya, N. V., Borodina, V. V., Shirobokova, M. G., Desenko, S. M., Musatov, V. I., Shishkina, S. V., Shishkin, O. V. & Zubatyuk, R. I. (2012). J. Heterocycl. Chem. 49, 1019-1025.  [CSD] [CrossRef] [ChemPort]
Matulkova, I., Cihelka, J., Pojarova, M., Fejfarova, K., Dusek, M., Vanek, P., Kroupa, J., Krupkova, R., Fabry, J. & Nemec, I. (2012). CrystEngComm, 14, 4625-4636.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sidorenko, D. Yu. & Orlov, V. D. (2011). Ultrason. Sonochem. 18, 300-302.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Sokolov, A. N., Mischenko, M. S., Gladkov, E. S. & Chernyshev, V. M. (2011). Chem. Heterocycl. Compd, 47, 249-251.  [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1586-o1587   [ doi:10.1107/S1600536813025853 ]

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