organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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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

(Received 17 December 2011; accepted 18 December 2011; online 23 December 2011)

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

  • β = 124.574 (1)°

  • V = 2152.87 (6) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 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 > 2σ(I)

  • Rint = 0.050

Refinement
  • R[F2 > 2σ(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

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.32 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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.]).

Supporting information


Comment top

We reported the reaction of 3-diamino-1,2,4-triazole and 4-hydroxy-6-methyl-pyran-2-one to form ethyl 2-(2-amino-5-methyl-[1,2,4]triazolo[1,5-a]pyrimidin-7-yl)acetate (Fettouhi et al., 1996), which is a member of a class of antiviral compounds. The use of 3,5-diamino-1,2,4-triazol with the pyrone gave the analogous amino-substituted compound (Scheme I). The nine-membered fused-ring of C10H13N5O2 is planar; the methylene unit connecting the fused-ring and the ethoxycarbonyl unit is slightly opened up to 111.33 (10)° (Fig. 1). The amino group forms hydrogen bonds to the N atoms of the triazole rings of adjacent molecules by a two-fold symmetry operation to generate a ribbon running along the a-axis of the monoclinic unit cell (Table 1).

Related literature top

For a related molecule, see: Fettouhi et al. (1996).

Experimental top

A solution of 3,5-diamino-1,2,4-triazole (1 g, 10 mmol) and 4-hydroxy-6-methyl-pyran-2-one (1.6g, 12.6 mmol) in ethanol (30 ml) was heated for 12 hours. The solvent was removed by evaporation and the residue recrystallized from ethanol to afford the colorless crystals.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

The amino H-atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.88±0.01 Å; their temperature factors were refined.

Computing details top

Data collection: APEX2 (Bruker, 2010); cell refinement: SAINT (Bruker, 2010); data reduction: SAINT (Bruker, 2010); 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).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of C10H13N5O2 at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.
Ethyl 2-(2-amino-5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7-yl)acetate top
Crystal data top
C10H13N5O2F(000) = 992
Mr = 235.25Dx = 1.452 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 3608 reflections
a = 22.9635 (4) Åθ = 2.8–35.5°
b = 7.7447 (1) ŵ = 0.11 mm1
c = 14.7017 (3) ÅT = 293 K
β = 124.574 (1)°Prism, colorless
V = 2152.87 (6) Å30.32 × 0.21 × 0.20 mm
Z = 8
Data collection top
Bruker APEX DUO
diffractometer
3058 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.050
Graphite monochromatorθmax = 34.7°, θmin = 2.8°
ω scansh = 3536
21320 measured reflectionsk = 129
4613 independent reflectionsl = 2322
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.050Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0666P)2 + 0.6364P]
where P = (Fo2 + 2Fc2)/3
4613 reflections(Δ/σ)max = 0.001
163 parametersΔρmax = 0.50 e Å3
2 restraintsΔρmin = 0.32 e Å3
Crystal data top
C10H13N5O2V = 2152.87 (6) Å3
Mr = 235.25Z = 8
Monoclinic, C2/cMo Kα radiation
a = 22.9635 (4) ŵ = 0.11 mm1
b = 7.7447 (1) ÅT = 293 K
c = 14.7017 (3) Å0.32 × 0.21 × 0.20 mm
β = 124.574 (1)°
Data collection top
Bruker APEX DUO
diffractometer
3058 reflections with I > 2σ(I)
21320 measured reflectionsRint = 0.050
4613 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0502 restraints
wR(F2) = 0.138H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.50 e Å3
4613 reflectionsΔρmin = 0.32 e Å3
163 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.66634 (4)0.58516 (12)0.48590 (7)0.01669 (18)
O20.59517 (5)0.70201 (15)0.31780 (7)0.0279 (2)
N10.60826 (5)0.99885 (13)0.53229 (7)0.01076 (18)
N20.67164 (5)0.93485 (13)0.61966 (7)0.01190 (18)
N30.66734 (5)1.23064 (13)0.63055 (8)0.01260 (19)
N40.55068 (5)1.27125 (14)0.46404 (8)0.01363 (19)
N50.77145 (5)1.08068 (14)0.76545 (8)0.0147 (2)
C10.77877 (6)0.45604 (19)0.56140 (11)0.0200 (3)
H1A0.81240.41830.54660.030*
H1B0.76460.35960.58560.030*
H1C0.80000.54270.61810.030*
C20.71486 (6)0.53072 (18)0.45759 (10)0.0177 (2)
H2A0.72840.62840.43210.021*
H2B0.69280.44450.39950.021*
C30.60866 (6)0.66849 (16)0.40788 (9)0.0151 (2)
C40.56130 (6)0.71606 (16)0.44533 (9)0.0140 (2)
H4A0.51500.66490.39550.017*
H4B0.58110.66940.51860.017*
C50.55386 (5)0.90755 (15)0.44764 (9)0.0118 (2)
C60.49644 (6)1.00289 (16)0.36969 (9)0.0133 (2)
H60.45730.94790.30990.016*
C70.49650 (6)1.18385 (16)0.37998 (9)0.0135 (2)
C80.43393 (6)1.28736 (18)0.29316 (10)0.0188 (2)
H8A0.43751.40290.31950.028*
H8B0.39121.23490.27730.028*
H8C0.43311.29040.22710.028*
C90.60642 (6)1.17669 (15)0.54011 (9)0.0114 (2)
C100.70439 (6)1.08132 (15)0.67461 (9)0.0115 (2)
H10.7866 (9)1.1735 (16)0.8069 (12)0.027 (4)*
H20.7920 (8)0.9812 (15)0.7978 (13)0.027 (4)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0130 (4)0.0209 (5)0.0142 (4)0.0049 (3)0.0066 (3)0.0026 (3)
O20.0328 (5)0.0336 (6)0.0165 (4)0.0168 (5)0.0135 (4)0.0082 (4)
N10.0087 (4)0.0096 (4)0.0101 (4)0.0000 (3)0.0030 (3)0.0006 (3)
N20.0087 (4)0.0104 (5)0.0101 (4)0.0000 (3)0.0015 (3)0.0003 (3)
N30.0108 (4)0.0102 (4)0.0118 (4)0.0001 (3)0.0034 (3)0.0002 (3)
N40.0108 (4)0.0114 (5)0.0145 (4)0.0010 (3)0.0047 (3)0.0007 (4)
N50.0122 (4)0.0110 (5)0.0113 (4)0.0002 (4)0.0009 (3)0.0004 (4)
C10.0147 (5)0.0207 (6)0.0225 (6)0.0038 (4)0.0094 (4)0.0025 (5)
C20.0178 (5)0.0181 (6)0.0180 (5)0.0034 (5)0.0106 (4)0.0006 (5)
C30.0148 (5)0.0116 (5)0.0138 (5)0.0009 (4)0.0050 (4)0.0017 (4)
C40.0118 (4)0.0102 (5)0.0153 (5)0.0013 (4)0.0049 (4)0.0020 (4)
C50.0093 (4)0.0116 (5)0.0116 (4)0.0015 (4)0.0043 (4)0.0025 (4)
C60.0091 (4)0.0140 (5)0.0115 (4)0.0001 (4)0.0028 (4)0.0016 (4)
C70.0100 (4)0.0147 (6)0.0125 (4)0.0007 (4)0.0044 (4)0.0003 (4)
C80.0122 (5)0.0170 (6)0.0178 (5)0.0039 (4)0.0028 (4)0.0027 (5)
C90.0113 (4)0.0087 (5)0.0124 (4)0.0004 (4)0.0057 (4)0.0000 (4)
C100.0112 (4)0.0107 (5)0.0104 (4)0.0007 (4)0.0048 (4)0.0001 (4)
Geometric parameters (Å, º) top
O1—C31.3276 (14)C1—H1B0.9600
O1—C21.4555 (15)C1—H1C0.9600
O2—C31.2049 (15)C2—H2A0.9700
N1—C51.3582 (14)C2—H2B0.9700
N1—N21.3755 (12)C3—C41.5169 (17)
N1—C91.3847 (15)C4—C51.4954 (17)
N2—C101.3474 (15)C4—H4A0.9700
N3—C91.3374 (14)C4—H4B0.9700
N3—C101.3621 (15)C5—C61.3720 (15)
N4—C71.3373 (14)C6—C71.4096 (17)
N4—C91.3419 (14)C6—H60.9300
N5—C101.3494 (14)C7—C81.5016 (16)
N5—H10.877 (9)C8—H8A0.9600
N5—H20.887 (9)C8—H8B0.9600
C1—C21.5085 (17)C8—H8C0.9600
C1—H1A0.9600
C3—O1—C2116.37 (9)C5—C4—H4A109.4
C5—N1—N2127.13 (10)C3—C4—H4A109.4
C5—N1—C9122.57 (9)C5—C4—H4B109.4
N2—N1—C9110.30 (9)C3—C4—H4B109.4
C10—N2—N1101.03 (9)H4A—C4—H4B108.0
C9—N3—C10103.08 (10)N1—C5—C6115.69 (11)
C7—N4—C9116.18 (10)N1—C5—C4118.66 (9)
C10—N5—H1117.7 (11)C6—C5—C4125.64 (10)
C10—N5—H2119.6 (11)C5—C6—C7120.23 (10)
H1—N5—H2117.3 (15)C5—C6—H6119.9
C2—C1—H1A109.5C7—C6—H6119.9
C2—C1—H1B109.5N4—C7—C6123.11 (10)
H1A—C1—H1B109.5N4—C7—C8117.06 (11)
C2—C1—H1C109.5C6—C7—C8119.83 (10)
H1A—C1—H1C109.5C7—C8—H8A109.5
H1B—C1—H1C109.5C7—C8—H8B109.5
O1—C2—C1106.55 (10)H8A—C8—H8B109.5
O1—C2—H2A110.4C7—C8—H8C109.5
C1—C2—H2A110.4H8A—C8—H8C109.5
O1—C2—H2B110.4H8B—C8—H8C109.5
C1—C2—H2B110.4N3—C9—N4128.53 (11)
H2A—C2—H2B108.6N3—C9—N1109.22 (9)
O2—C3—O1124.23 (11)N4—C9—N1122.23 (10)
O2—C3—C4123.83 (11)N2—C10—N5121.70 (10)
O1—C3—C4111.95 (10)N2—C10—N3116.37 (9)
C5—C4—C3111.33 (10)N5—C10—N3121.86 (10)
C5—N1—N2—C10178.81 (11)C9—N4—C7—C8179.26 (11)
C9—N1—N2—C100.44 (12)C5—C6—C7—N40.35 (18)
C3—O1—C2—C1174.51 (11)C5—C6—C7—C8178.90 (11)
C2—O1—C3—O20.81 (19)C10—N3—C9—N4178.56 (12)
C2—O1—C3—C4178.92 (10)C10—N3—C9—N10.13 (12)
O2—C3—C4—C562.89 (16)C7—N4—C9—N3178.85 (11)
O1—C3—C4—C5117.38 (11)C7—N4—C9—N10.31 (16)
N2—N1—C5—C6179.22 (10)C5—N1—C9—N3179.09 (10)
C9—N1—C5—C60.05 (16)N2—N1—C9—N30.20 (13)
N2—N1—C5—C40.24 (17)C5—N1—C9—N40.30 (17)
C9—N1—C5—C4178.93 (10)N2—N1—C9—N4178.99 (10)
C3—C4—C5—N176.46 (13)N1—N2—C10—N5176.45 (10)
C3—C4—C5—C6102.41 (13)N1—N2—C10—N30.56 (13)
N1—C5—C6—C70.35 (16)C9—N3—C10—N20.45 (13)
C4—C5—C6—C7178.55 (11)C9—N3—C10—N5176.55 (10)
C9—N4—C7—C60.00 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H1···N2i0.88 (1)2.24 (1)3.095 (1)166 (2)
N5—H2···N3ii0.89 (1)2.15 (1)3.037 (2)175 (2)
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+3/2, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC10H13N5O2
Mr235.25
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)22.9635 (4), 7.7447 (1), 14.7017 (3)
β (°) 124.574 (1)
V3)2152.87 (6)
Z8
Radiation typeMo Kα
µ (mm1)0.11
Crystal size (mm)0.32 × 0.21 × 0.20
Data collection
DiffractometerBruker APEX DUO
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21320, 4613, 3058
Rint0.050
(sin θ/λ)max1)0.801
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.138, 1.02
No. of reflections4613
No. of parameters163
No. of restraints2
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.50, 0.32

Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H1···N2i0.88 (1)2.24 (1)3.095 (1)166 (2)
N5—H2···N3ii0.89 (1)2.15 (1)3.037 (2)175 (2)
Symmetry codes: (i) x+3/2, y+1/2, z+3/2; (ii) x+3/2, y1/2, z+3/2.
 

Acknowledgements

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

References

First citationBarbour, L. J. (2001). J. Supramol. Chem. 1, 189–191.  CrossRef CAS
First citationBruker (2010). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationFettouhi, M., Boukhari, A., El Otmani, B. & Essassi, E. M. (1996). Acta Cryst. C52, 1031–1032.  CSD CrossRef CAS Web of Science IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals

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