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Volume 69 
Part 2 
Pages o227-o228  
February 2013  

Received 18 December 2012
Accepted 2 January 2013
Online 12 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.038
wR = 0.107
Data-to-parameter ratio = 10.3
Details
Open access

N-(5-Amino-1H-1,2,4-triazol-3-yl)pyridine-2-carboxamide

aDepartament de Química Inorgànica, Universitat de València, Vicent Andrés Estellés s/n, 46100 Burjassot, València, Spain,bDepartament de Química Orgànica, Universitat de València, Vicent Andrés Estellés s/n, 46100 Burjassot, València, Spain, and cDeptament de Química Inorgánica, Universitat de Santiago de Compostela, Campus vida, Santiago de Compostela, Galicia, 15782, Spain
Correspondence e-mail: alfonso.castineiras@usc.es

The title compound, C8H8N6O, was obtained by the reaction of 3,5-diamino-1,2,4-triazole with ethyl 2-picolinate in a glass oven. The dihedral angles formed between the plane of the amide group and the pyridine and triazole rings are 11.8 (3) and 5.8 (3)°, respectively. In the crystal, an extensive system of classical N-H...N and N-H...O hydrogen bonds generate an infinite three-dimensional network.

Related literature

For background to triazole derivatives, see: Aromí et al. (2011[Aromí, G., Barrios, L., Roubeuau, O. & Gámez, P. (2011). Coord. Chem. Rev. 255, 485-546.]); Olguín et al. (2012[Olguín, J., Kalisz, J. M., Clé, R. & Brooker, S. (2012). Inorg. Chem. 51, 5058-5069.]). For related triazole structures, see: Allouch et al. (2008[Allouch, F., Zouari, F., Chabchoub, F. & Salem, M. (2008). Acta Cryst. E64, o684.]); Ouakkaf et al. (2011[Ouakkaf, A., Berrah, F., Bouacida, S. & Roisnel, T. (2011). Acta Cryst. E67, o1171-o1172.]). For structures of metal complexes with related triazoles, see: Ferrer et al. (2004[Ferrer, S., Ballesteros, R., Sambartolomé, A., González, M., Alzuet, M. G., Borrás, J. & Liu, M. (2004). J. Inorg. Biochem. 98, 1436-1446.], 2012[Ferrer, S., Lloret, F., Pardo, E., Clemente-Juan, J. M., Liu-González, M. & García-Granda, S. (2012). Inorg. Chem. 51, 985-1001.]). For the synthesis of triazoles, 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 hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C8H8N6O

  • Mr = 204.20

  • Tetragonal, P 41 21 2

  • a = 9.5480 (5) Å

  • c = 21.9570 (9) Å

  • V = 2001.69 (17) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 293 K

  • 0.15 × 0.09 × 0.05 mm

Data collection
  • Nonius KappaCCD diffractometer

  • 4484 measured reflections

  • 1407 independent reflections

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

  • Rint = 0.048

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.107

  • S = 1.07

  • 1407 reflections

  • 137 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.12 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N21-H21...N23i 0.86 2.02 2.788 (3) 149
N21-H21...O17i 0.86 2.41 3.061 (3) 133
N18-H18...N20ii 0.86 2.45 3.253 (3) 155
N22-H22A...O17i 0.86 2.08 2.860 (3) 150
N22-H22B...N20iii 0.86 2.26 3.068 (3) 157
Symmetry codes: (i) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 4}}]; (ii) [-y, -x, -z+{\script{1\over 2}}]; (iii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 4}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft. The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzimology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Cortes Jr & R. M. Sweet, pp 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and DIAMOND (Brandenburg & Putz, 2006[Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: GK2547 ).


Acknowledgements

This work was supported by the Ministerio de Educación y Ciencia (MEC, Spain) (project CTQ2007-63690/BQU) and by the Ministerio de Ciencia e Innovación and FEDER-EC (project MAT2010-15594). JHG acknowledges a PhD grant (project CTQ2007-63690/BQU, MEC, Spain). Technical support (X-ray measurements at S.C.S.I.E., University of Valencia) from M. Liu-González is gratefully acknowledged.

References

Allouch, F., Zouari, F., Chabchoub, F. & Salem, M. (2008). Acta Cryst. E64, o684.  [CSD] [CrossRef] [details]
Aromí, G., Barrios, L., Roubeuau, O. & Gámez, P. (2011). Coord. Chem. Rev. 255, 485-546.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Chernyshev, V. M., Rakitov, V. A., Taranushich, V. A. & Blinov, V. V. (2005). Chem. Heterocycl. Compd, 41, 1139-1146.  [CrossRef] [ChemPort]
Ferrer, S., Ballesteros, R., Sambartolomé, A., González, M., Alzuet, M. G., Borrás, J. & Liu, M. (2004). J. Inorg. Biochem. 98, 1436-1446.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Ferrer, S., Lloret, F., Pardo, E., Clemente-Juan, J. M., Liu-González, M. & García-Granda, S. (2012). Inorg. Chem. 51, 985-1001.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Nonius (1998). COLLECT. Nonius BV, Delft. The Netherlands.
Olguín, J., Kalisz, J. M., Clé, R. & Brooker, S. (2012). Inorg. Chem. 51, 5058-5069.  [ISI] [PubMed]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzimology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Cortes Jr & R. M. Sweet, pp 307-326. New York: Academic Press.
Ouakkaf, A., Berrah, F., Bouacida, S. & Roisnel, T. (2011). Acta Cryst. E67, o1171-o1172.  [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o227-o228   [ doi:10.1107/S1600536813000123 ]

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