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

Gueddar, H.; Bouhfid, R.; Guessous, A.R.; Essassi, E.M.; Ng, S.W.

doi:10.1107/S1600536811054468

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 (C-C) = 0.002 Å
R = 0.050
wR = 0.138
Data-to-parameter ratio = 28.3
Details

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

Hicham Gueddar,^a Rachid Bouhfid,^b Ahmed Radouane Guessous,^a El Mokhtar Essassi ^a and Seik Weng Ng ^c,^d ^*

^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).

Experimental

Crystal data

C₁₀H₁₃N₅O₂
M_r = 235.25
Monoclinic, C 2/c
a = 22.9635 (4) Å
b = 7.7447 (1) Å
c = 14.7017 (3) Å
= 124.574 (1)°
V = 2152.87 (6) Å³
Z = 8
Mo K radiation
= 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(I)
R_int = 0.050

Refinement

R[F² > 2(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
_max = 0.50 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N5-H1N2ⁱ	0.88 (1)	2.24 (1)	3.095 (1)	166 (2)
N5-H2N3ⁱⁱ	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); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
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.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References