[Journal logo]

Volume 68 
Part 1 
Page o239  
January 2012  

Received 17 December 2011
Accepted 18 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.050
wR = 0.138
Data-to-parameter ratio = 28.3
Details
Open access

Ethyl 2-(2-amino-5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)acetate

aLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco,bInstitute of Nanomaterials and Nanotechnology, MAScIR, Avenue de l'Armée Royale, Rabat, Morocco,cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and dChemistry Department, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: seikweng@um.edu.my

The nine-membered fused-ring of the title compound, C10H13N5O2, is approximately planar [maximum deviation = 0.012 (1) Å]; the bond angle at the methylene C atom is 111.33 (10)°. In the crystal, the amino group forms hydrogen bonds to the N atoms of the triazole rings of adjacent molecules, generating a ribbon running along the a axis.

Related literature

For a related molecule, see: Fettouhi et al. (1996[Fettouhi, M., Boukhari, A., El Otmani, B. & Essassi, E. M. (1996). Acta Cryst. C52, 1031-1032.]).

[Scheme 1]

Experimental

Crystal data
  • C10H13N5O2

  • Mr = 235.25

  • Monoclinic, C 2/c

  • a = 22.9635 (4) Å

  • b = 7.7447 (1) Å

  • c = 14.7017 (3) Å

  • [beta] = 124.574 (1)°

  • V = 2152.87 (6) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.32 × 0.21 × 0.20 mm

Data collection
  • Bruker APEX DUO diffractometer

  • 21320 measured reflections

  • 4613 independent reflections

  • 3058 reflections with I > 2[sigma](I)

  • Rint = 0.050

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.138

  • S = 1.02

  • 4613 reflections

  • 163 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.50 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5-H1...N2i 0.88 (1) 2.24 (1) 3.095 (1) 166 (2)
N5-H2...N3ii 0.89 (1) 2.15 (1) 3.037 (2) 175 (2)
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2010[Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); 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: XU5412 ).


Acknowledgements

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Fettouhi, M., Boukhari, A., El Otmani, B. & Essassi, E. M. (1996). Acta Cryst. C52, 1031-1032.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o239  [ doi:10.1107/S1600536811054468 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.