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Volume 69 
Part 11 
Pages o1648-o1649  
November 2013  

Received 27 September 2013
Accepted 9 October 2013
Online 16 October 2013

Key indicators
Single-crystal X-ray study
T = 120 K
Mean [sigma](C-C) = 0.001 Å
R = 0.042
wR = 0.118
Data-to-parameter ratio = 21.2
Details
Open access

3-Methyl-4-(2-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)furazan

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

In the title mol­ecule, C14H10N6O, the planes of the methyl­furazan fragment and the phenyl ring attached to the triazolo­pyrimidine bicycle are twisted from the mean plane of the bicycle at angles of 45.92 (5) and 5.45 (4)°, respectively. In the crystal, [pi]-[pi] inter­actions, indicated by short distances [in the range 3.456 (3)-3.591 (3) Å] between the centroids of the five- and six-membered rings of neighbouring mol­ecules, link the mol­ecules into stacks propagating along the c-axis direction.

Related literature

For applications of enamino­nes in synthesis, see: Kulinich & Ischenko (2009[Kulinich, A. B. & Ischenko, A. A. (2009). Russ. Chem. Rev. 78, 141-164 [translated from (2009). Usp. Khim. 78, 151-175].]); Stanovnik & Svete (2004[Stanovnik, B. & Svete, J. (2004). Chem. Rev. 104, 2433-2480.]). For the synthesis of triazolo­pyrimidines from enamino­propenones, see: Abdelhamid et al. (2012[Abdelhamid, A. O., Shokry, S. A. & Tawfiek, S. M. (2012). J. Heterocycl. Chem. 49, 116-124.], 2013[Abdelhamid, A. O., Fahmi, A. A. & Halim, K. N. M. (2013). Synth. Commun. 43, 1101-1126.]); Behbehani & Ibrahim (2012[Behbehani, H. & Ibrahim, H. M. (2012). Molecules, 17, 6362-6385.]). For X-ray studies of [1,2,4]triazolo[a]pyrimidines, see: Lipkind et al. (2011[Lipkind, D., Rath, N., Chickos, J. S., Pozdeev, V. A. & Verekin, S. P. (2011). J. Phys. Chem. B, 115, 8785-8796.]); Shikhaliev et al. (2008[Shikhaliev, Kh. S., Kryl'skii, D. V., Potapov, A. Yu., Nefedov, S. E. & Sidorenko, O. E. (2008). Russ. Chem. Bull. 57, 1268-1272 [translated from (2008). Izv. AN, Ser. Khim. pp. 1244-1248].]); Lokaj et al. (2006[Lokaj, J., Kettmann, V., Katuscák, S., Cernuchová, P., Milata, V. & Gregán, F. (2006). Acta Cryst. E62, o1252-o1253.]) and of furazan derivatives, see: Sheremetev et al. (2004[Sheremetev, A. B., Andrianov, V. G., Mantseva, E. V., Shatunova, E. V., Aleksandrova, N. S., Yudin, I. L., Dmitriev, D. E., Averkiev, B. B. & Antipin, M. Yu. (2004). Russ. Chem. Bull. Int. Ed. 53, 596-614 [translated from (2004). Izv. AN, Ser. Khim. pp. 569-586].], 2006[Sheremetev, A. B., Yudin, I. L. & Suponitsky, K. Yu. (2006). Mendeleev Commun. 16, 264-266.], 2012[Sheremetev, A. B., Yudin, I. L., Palysaeva, N. V. & Suponitsky, K. Yu. (2012). J. Heterocycl. Chem. 49, 394-401.], 2013[Sheremetev, A. B., Aleksandrova, N. S., Palysaeva, N. V., Struchkova, M. I., Tartakovsky, V. A. & Suponitsky, K. Yu. (2013). Chem. Eur. J. 19, 12446-12457.]); Suponitsky et al. (2009a[Suponitsky, K. Yu., Lyssenko, K. A., Antipin, M. Yu., Aleksandrova, N. S., Sheremetev, A. B. & Novikova, T. S. (2009a). Russ. Chem. Bull. 58, 2129-2136 [translated from (2009). Izv. AN, Ser. Khim. pp. 2065-2071].],b[Suponitsky, K. Yu., Masunov, A. E. & Antipin, M. Yu. (2009b). Mendeleev Commun. 19, 311-313.]). For normal values of bond lengths in organic compounds, 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.]) and for a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]).

[Scheme 1]

Experimental

Crystal data
  • C14H10N6O

  • Mr = 278.28

  • Monoclinic, P 21 /c

  • a = 11.1397 (6) Å

  • b = 15.6579 (8) Å

  • c = 7.3952 (4) Å

  • [beta] = 101.332 (1)°

  • V = 1264.76 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 120 K

  • 0.32 × 0.28 × 0.26 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 16844 measured reflections

  • 4041 independent reflections

  • 3456 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.118

  • S = 1.02

  • 4041 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.42 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

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: CV5430 ).


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 in Years 2009-2013" (grant No. 14.B37.21.1187) and, in part, through State research contract No. 3.2107.2011.

References

Abdelhamid, A. O., Fahmi, A. A. & Halim, K. N. M. (2013). Synth. Commun. 43, 1101-1126.  [Web of Science] [CrossRef] [ChemPort]
Abdelhamid, A. O., Shokry, S. A. & Tawfiek, S. M. (2012). J. Heterocycl. Chem. 49, 116-124.  [CrossRef] [ChemPort]
Allen, F. H. (2002). Acta Cryst. B58, 380-388.  [Web of Science] [CrossRef] [IUCr Journals]
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.
Behbehani, H. & Ibrahim, H. M. (2012). Molecules, 17, 6362-6385.  [CSD] [CrossRef] [ChemPort] [PubMed]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Kulinich, A. B. & Ischenko, A. A. (2009). Russ. Chem. Rev. 78, 141-164 [translated from (2009). Usp. Khim. 78, 151-175].
Lipkind, D., Rath, N., Chickos, J. S., Pozdeev, V. A. & Verekin, S. P. (2011). J. Phys. Chem. B, 115, 8785-8796.  [CSD] [CrossRef] [ChemPort] [PubMed]
Lokaj, J., Kettmann, V., Katuscák, S., Cernuchová, P., Milata, V. & Gregán, F. (2006). Acta Cryst. E62, o1252-o1253.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Sheremetev, A. B., Aleksandrova, N. S., Palysaeva, N. V., Struchkova, M. I., Tartakovsky, V. A. & Suponitsky, K. Yu. (2013). Chem. Eur. J. 19, 12446-12457.  [CSD] [CrossRef] [ChemPort] [PubMed]
Sheremetev, A. B., Andrianov, V. G., Mantseva, E. V., Shatunova, E. V., Aleksandrova, N. S., Yudin, I. L., Dmitriev, D. E., Averkiev, B. B. & Antipin, M. Yu. (2004). Russ. Chem. Bull. Int. Ed. 53, 596-614 [translated from (2004). Izv. AN, Ser. Khim. pp. 569-586].
Sheremetev, A. B., Yudin, I. L., Palysaeva, N. V. & Suponitsky, K. Yu. (2012). J. Heterocycl. Chem. 49, 394-401.  [CSD] [CrossRef] [ChemPort]
Sheremetev, A. B., Yudin, I. L. & Suponitsky, K. Yu. (2006). Mendeleev Commun. 16, 264-266.  [Web of Science] [CSD] [CrossRef]
Shikhaliev, Kh. S., Kryl'skii, D. V., Potapov, A. Yu., Nefedov, S. E. & Sidorenko, O. E. (2008). Russ. Chem. Bull. 57, 1268-1272 [translated from (2008). Izv. AN, Ser. Khim. pp. 1244-1248].
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Stanovnik, B. & Svete, J. (2004). Chem. Rev. 104, 2433-2480.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Suponitsky, K. Yu., Lyssenko, K. A., Antipin, M. Yu., Aleksandrova, N. S., Sheremetev, A. B. & Novikova, T. S. (2009a). Russ. Chem. Bull. 58, 2129-2136 [translated from (2009). Izv. AN, Ser. Khim. pp. 2065-2071].
Suponitsky, K. Yu., Masunov, A. E. & Antipin, M. Yu. (2009b). Mendeleev Commun. 19, 311-313.  [Web of Science] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1648-o1649   [ doi:10.1107/S1600536813027700 ]

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