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Volume 69 
Part 11 
Pages o1630-o1631  
November 2013  

Received 1 October 2013
Accepted 4 October 2013
Online 12 October 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.003 Å
R = 0.037
wR = 0.094
Data-to-parameter ratio = 10.2
Details
Open access

6-(3,5-Dimethyl-1H-pyrazol-1-yl)-1,2,4,5-tetra­zin-3(2H)-one

aA. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova St, 119991 Moscow, Russian Federation,bSouth-Russia State Technical University, 346428 Novocherkassk, Russian Federation, and cN. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prosp, 119991 Moscow, Russian Federation
Correspondence e-mail: kirshik@yahoo.com

The title compound, C7H8N6O, represents the keto form and adopts a nearly planar structure (r.m.s. deviation of the non-H atoms = 0.072 Å). In the crystal, mol­ecules form spiral chains along the c axis by N-H...N hydrogen bonds. The chains are linked to each other by weak C-H...O hydrogen bonds, forming a three-dimensional framework.

Related literature

For review on nucleophilic displacement at the 1,2,4,5-tetra­zine ring, see: Clavier & Audebert (2010[Clavier, G. & Audebert, P. (2010). Chem. Rev. 110, 3299-3314.]); Tolshchina et al. (2013[Tolshchina, S. G., Rusinov, G. L. & Charushin, V. N. (2013). Chem. Heterocycl. Compd, 49, 66-91 [translated from (2013). Khim. Geterotsikl. Soedin. pp. 75-101].]). For the synthesis of 3-hy­droxy-1,2,4,5-tetra­zines, see: Ishmetova et al. (2009[Ishmetova, R. I., Latosh, N. I., Ganebnykh, I. N., Ignatenko, N. K., Tolshchina, S. G. & Rusinov, G. L. (2009). Russ. J. Org. Chem. 45, 1102-1107 [translated from (2009). Zh. Org. Khim. 45, 1113-1118].]); Sheremetev et al. (2012a[Sheremetev, A. B., Palysaeva, N. V., Struchkova, M. I. & Suponitskii, K. Yu. (2012a). Russ. Chem. Bull. 61, 121-130 [translated from (2012). Izv. Akad. Nauk, Ser. Khim. 119-128].],b[Sheremetev, A. B., Palysaeva, N. V., Struchkova, M. I. & Suponitsky, K. Yu. (2012b). Mendeleev Commun. 22, 302-304.]). For the structure of 3-hy­droxy-1,2,4,5-tetra­zine, see: Yeh et al. (1994[Yeh, M.-Y., Huang, C.-Y., Ueng, C.-H. & Wang, Y. (1994). Acta Cryst. C50, 1781-1784.]). For a review on oxo-hy­droxy tautomerism of various azines, see: Stanovnik et al. (2006[Stanovnik, B., Tisler, M., Katritzky, A. R. & Denisko, O. V. (2006). Adv. Heterocycl. Chem. 91, 1-134.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C7H8N6O

  • Mr = 192.19

  • Orthorhombic, P n a 21

  • a = 12.1431 (11) Å

  • b = 12.6551 (12) Å

  • c = 5.3907 (5) Å

  • V = 828.40 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 120 K

  • 0.28 × 0.22 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 14157 measured reflections

  • 1353 independent reflections

  • 1228 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.094

  • S = 1.05

  • 1353 reflections

  • 133 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N4-H4...N1i 0.89 (3) 2.00 (3) 2.863 (2) 161 (3)
C2-H2A...O1ii 0.95 2.40 3.193 (3) 141
Symmetry codes: (i) [-x+2, -y+1, z+{\script{1\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z-{\script{3\over 2}}].

Data collection: APEX (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, PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: KQ2010 ).


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 a Russian Foundation for Basic Research (grant No. 12-03-31346).

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.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Clavier, G. & Audebert, P. (2010). Chem. Rev. 110, 3299-3314.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Ishmetova, R. I., Latosh, N. I., Ganebnykh, I. N., Ignatenko, N. K., Tolshchina, S. G. & Rusinov, G. L. (2009). Russ. J. Org. Chem. 45, 1102-1107 [translated from (2009). Zh. Org. Khim. 45, 1113-1118].
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheremetev, A. B., Palysaeva, N. V., Struchkova, M. I. & Suponitskii, K. Yu. (2012a). Russ. Chem. Bull. 61, 121-130 [translated from (2012). Izv. Akad. Nauk, Ser. Khim. 119-128].
Sheremetev, A. B., Palysaeva, N. V., Struchkova, M. I. & Suponitsky, K. Yu. (2012b). Mendeleev Commun. 22, 302-304.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stanovnik, B., Tisler, M., Katritzky, A. R. & Denisko, O. V. (2006). Adv. Heterocycl. Chem. 91, 1-134.  [Web of Science] [CrossRef] [ChemPort]
Tolshchina, S. G., Rusinov, G. L. & Charushin, V. N. (2013). Chem. Heterocycl. Compd, 49, 66-91 [translated from (2013). Khim. Geterotsikl. Soedin. pp. 75-101].
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yeh, M.-Y., Huang, C.-Y., Ueng, C.-H. & Wang, Y. (1994). Acta Cryst. C50, 1781-1784.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1630-o1631   [ doi:10.1107/S1600536813027360 ]

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