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Volume 67 
Part 4 
Pages o870-o871  
April 2011  

Received 9 February 2011
Accepted 22 February 2011
Online 12 March 2011

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.005 Å
R = 0.059
wR = 0.160
Data-to-parameter ratio = 15.7
Details
Open access

4-Benzyl-3-[(1-oxidoethylidene)amino]-1-phenyl-4,5-dihydro-1H-1,2,4-triazol-5-iminium

aSouth-Russia State Technical University, 346428 Novocherkassk, Russian Federation, and bDepartment of Chemistry, Moscow State University, 119992 Moscow, Russian Federation
Correspondence e-mail: rybakov20021@yandex.ru

The title compound, C17H17N5O, exists in the zwitterionic form with the amide group deprotonated. The mean planes of the 1,2,4-triazole and N-phenyl rings form a dihedral angle of 39.14 (8)°. The N atom of the amino group adopts a trigonal configuration. Intermoleculat C-H...O and C-H...N hydrogen bonds occur. In the crystal, molecules are linked into a two-dimensional network parallel to (10[\overline{1}]) by N-H...O and N-H...N hydrogen bonds. C-H...N contacts are also observed.

Related literature

For the synthesis of the starting compound, N-(5-amino-1-phenyl-1H-1,2,4-triazol-3-yl)acetamide, see: Chernyshev et al. (2005[Chernyshev, V. M., Rakitov, V. A., Taranushich, V. A. & Blinov, V. V. (2005). Chem. Heterocycl. Compd, 41, 1139-1146.]). For alkylation and other reactions of related compounds with electrophiles, see: Chernyshev et al. (2008a[Chernyshev, V. M., Sokolov, A. N., Khoroshkin, D. A. & Taranushich, V. A. (2008a). Russ. J. Org. Chem. 44, 715-722.],b[Chernyshev, V. M., Khoroshkin, D. A., Sokolov, A. N., Taranushich, V. A., Gladkov, E. S., Shishkina, S. V., Shishkin, O. V. & Desenko, S. M. (2008b). J. Heterocycl. Chem. 45, 1419-1427.]). For crystal structures of 3(5)-acylamino-1,2,4-triazoles, see: Selby & Lepone (1984[Selby, T. P. & Lepone, G. E. (1984). J. Heterocycl. Chem. 21, 61-64.]); Gyorgydeak et al. (1995[Gyorgydeak, Z., Holzer, W., Kunz, R. W. & Linden, A. (1995). Monatsh. Chem. 126, 733-746.]); Chernyshev et al. (2006[Chernyshev, V. M., Kosov, A. E., Gladkov, E. S., Shishkina, S. V., Taranushich, V. A., Desenko, S. M. & Shishkin, O. V. (2006). Russ. Chem. Bull. 55, 338-344.]); Masiukiewicz et al. (2007[Masiukiewicz, E., Rzeszotarska, B., Wawrzycka-Gorczyca, I. & Kolodziejczyk, E. (2007). Synth. Commun. 37, 1917-1925.]); Miao et al. (2009[Miao, J., Jia, M., Liu, X., Xiong, W. & Chen, Z. (2009). Acta Cryst. E65, o2738.]). For crystal structures of 5-amino-1,2,4-triazolium salts, see: Darwich et al. (2008a[Darwich, C., Karaghiosoff, K., Kaloptke, T. M. & Sabate, C. M. (2008a). Z. Anorg. Allg. Chem. 634, 61-68.],b[Darwich, C., Klapotke, T. M. & Sabate, C. M. (2008b). Chem. Eur. J. 14, 5756-5771.]); Klapotke & Sabate (2008[Klapotke, T. M. & Sabate, C. M. (2008). Eur. J. Inorg. Chem. pp. 5350-5366.]); Tao et al. (2009[Tao, G.-H., Twamley, B. & Shreeve, J. M. (2009). J. Mater. Chem. 19, 5850-5854.]); Chernyshev et al. (2010[Chernyshev, V. M., Astakhov, A. V., Ivanov, V. V. & Starikova, Z. A. (2010). Acta Cryst. E66, o1644-o1645.]). 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 in sp2-hybridized C and N atoms, see: Burke-Laing & Laing (1976[Burke-Laing, M. & Laing, M. (1976). Acta Cryst. B32, 3216-3224.]).

[Scheme 1]

Experimental

Crystal data
  • C17H17N5O

  • Mr = 307.36

  • Monoclinic, P 21 /n

  • a = 10.262 (2) Å

  • b = 15.240 (3) Å

  • c = 10.967 (2) Å

  • [beta] = 113.86 (2)°

  • V = 1568.6 (6) Å3

  • Z = 4

  • Ag K[alpha] radiation

  • [lambda] = 0.56085 Å

  • [mu] = 0.06 mm-1

  • T = 295 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 3582 measured reflections

  • 3412 independent reflections

  • 2294 reflections with I > 2[sigma](I)

  • Rint = 0.068

  • 1 standard reflections every 6 min intensity decay: 0%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.160

  • S = 1.03

  • 3412 reflections

  • 218 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N51-H51A...O14i 0.94 (3) 1.83 (3) 2.739 (3) 161 (2)
N51-H51B...N13ii 0.84 (3) 2.18 (3) 2.971 (3) 157 (3)
C6-H6B...O14 0.97 2.30 3.045 (3) 133
C8-H8...N13 0.93 2.72 3.454 (4) 136
C12-H12...N13ii 0.93 2.54 3.441 (4) 162
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AA2002 ).


Acknowledgements

This work was supported by the Ministry of Education and Science of the Russian Federation through the Federal Target Program `Research and Educational Personnel of Innovative Russia in 2009-2013 Years', State contract P302, project NK-109P/2. The authors are indebted to the Russian Foundation for Basic Research for covering the licence fee for use of the Cambridge Structural Database (Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

References

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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.
Burke-Laing, M. & Laing, M. (1976). Acta Cryst. B32, 3216-3224.  [CrossRef] [details]
Chernyshev, V. M., Astakhov, A. V., Ivanov, V. V. & Starikova, Z. A. (2010). Acta Cryst. E66, o1644-o1645.  [CrossRef] [details]
Chernyshev, V. M., Khoroshkin, D. A., Sokolov, A. N., Taranushich, V. A., Gladkov, E. S., Shishkina, S. V., Shishkin, O. V. & Desenko, S. M. (2008b). J. Heterocycl. Chem. 45, 1419-1427.  [ChemPort]
Chernyshev, V. M., Kosov, A. E., Gladkov, E. S., Shishkina, S. V., Taranushich, V. A., Desenko, S. M. & Shishkin, O. V. (2006). Russ. Chem. Bull. 55, 338-344.  [ISI] [CrossRef] [ChemPort]
Chernyshev, V. M., Rakitov, V. A., Taranushich, V. A. & Blinov, V. V. (2005). Chem. Heterocycl. Compd, 41, 1139-1146.  [CrossRef] [ChemPort]
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Darwich, C., Karaghiosoff, K., Kaloptke, T. M. & Sabate, C. M. (2008a). Z. Anorg. Allg. Chem. 634, 61-68.  [ChemPort]
Darwich, C., Klapotke, T. M. & Sabate, C. M. (2008b). Chem. Eur. J. 14, 5756-5771.  [ChemPort]
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
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Gyorgydeak, Z., Holzer, W., Kunz, R. W. & Linden, A. (1995). Monatsh. Chem. 126, 733-746.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Klapotke, T. M. & Sabate, C. M. (2008). Eur. J. Inorg. Chem. pp. 5350-5366.
Masiukiewicz, E., Rzeszotarska, B., Wawrzycka-Gorczyca, I. & Kolodziejczyk, E. (2007). Synth. Commun. 37, 1917-1925.  [ChemPort]
Miao, J., Jia, M., Liu, X., Xiong, W. & Chen, Z. (2009). Acta Cryst. E65, o2738.  [CrossRef] [details]
Selby, T. P. & Lepone, G. E. (1984). J. Heterocycl. Chem. 21, 61-64.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tao, G.-H., Twamley, B. & Shreeve, J. M. (2009). J. Mater. Chem. 19, 5850-5854.  [ChemPort]


Acta Cryst (2011). E67, o870-o871   [ doi:10.1107/S1600536811006751 ]

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