2-Amino-5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one

Lahmidi, S.; El Hafi, M.; Sebbar, N. kheira; Abad, N.; Essassi, E.M.; Mague, J.T.

doi:10.1107/S2414314618015006

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 11| November 2018| x181500

https://doi.org/10.1107/S2414314618015006

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2-Amino-5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one

Sanae Lahmidi,^a ^* Mohamed El Hafi,^a Nada kheira Sebbar,^a Nadeem Abad,^a El Mokhtar Essassi ^a and Joel T. Mague ^b

^aLaboratoire de Chimie Organique Hétérocyclique, Centre de Recherche Des Sciences des Médicaments, Pôle de Compétence Pharmacochimie, Av Ibn Battouta, BP 1014, Faculté des Sciences, Université Mohammed V, Rabat, Morocco, and ^bDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA
^*Correspondence e-mail: asb.sanae@gmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 20 September 2018; accepted 23 October 2018; online 16 November 2018)

The asymmetric unit of the title compound, C₆H₇N₅O, consists of two molecules with almost identical conformations. In the crystal, inversion dimers linked by pairs of N—H⋯N hydrogen bonds occur for both molecules; further N—H⋯N and N—H⋯O hydrogen bonds connect the dimers into a three-dimensional network.

Keywords: crystal structure; triazole; pyrimidine; hydrogen bond.

CCDC reference: 1874902

Structure description

As a continuation of our studies of triazolopyrimidine derivatives (Lahmidi et al., 2016 ; El Hafi et al., 2017 ), we now report the synthesis and crystal structure of the title compound (Fig. 1).

Figure 1
The asymmetric unit with labelling scheme and 50% probability ellipsoids. The N—H⋯N hydrogen bond is shown by a dashed line.

The asymmetric unit consists of two independent molecules with almost identical conformations; as expected, the molecules are almost planar with r.m.s. deviations for the N1 and N6 molecules of 0.011 and 0.0052 Å, respectively. The dihedral angle between the mean planes of the independent molecules in the asymmetric unit, which are linked by an N1—H1⋯N7 hydrogen bond, is 78.27 (3)°. In the extended structure, inversion dimers linked by pairs of N—H⋯N hydrogen bonds generate R₂²(8) loops for both molecules (Table 1). Further N—H⋯N and N—H⋯O hydrogen bonds connect the dimers into a three-dimensional network (Table 1 and Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N7	0.85 (2)	2.00 (2)	2.8520 (18)	176 (2)
N5—H5A⋯N2ⁱ	0.93 (2)	2.20 (2)	3.1240 (18)	173.3 (17)
N5—H5B⋯O2ⁱⁱ	0.881 (18)	2.097 (19)	2.9733 (18)	172.7 (16)
N6—H6⋯N3ⁱⁱⁱ	0.944 (19)	1.94 (2)	2.8724 (17)	168.6 (17)
N10—H10A⋯O1^iv	0.863 (18)	2.069 (18)	2.8935 (17)	159.5 (16)
N10—H10B⋯N8^v	0.845 (18)	2.220 (19)	3.0330 (19)	161.2 (16)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y, z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y, -z+1; (v) -x, -y, -z.

Figure 2
Packing showing the hydrogen-bonding network with the N—H⋯O and N—H⋯N hydrogen bonds shown, respectively, as purple and blue dashed lines.

Synthesis and crystallization

A mixture of 3,5-diamino-1,2,4-triazole (0.5 g, 5 mmol) and ethyl acetoacetate (0.64 ml, 5 mmol) and 15 ml of acetic acid was refluxed for 6 h. The solution was cooled and evaporated to dryness under reduced pressure and ethanol (7 ml) was added. After four days, colourless columnar crystals were recovered in 75% yield.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₆H₇N₅O
M_r	165.17
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	100
a, b, c (Å)	6.5921 (14), 8.3935 (18), 13.185 (3)
α, β, γ (°)	92.023 (3), 98.309 (3), 99.741 (3)
V (Å³)	710.1 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.12
Crystal size (mm)	0.39 × 0.16 × 0.09

Data collection
Diffractometer	Bruker SMART APEX CCD
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.96, 0.99
No. of measured, independent and observed [I > 2σ(I)] reflections	6817, 3503, 2743
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.138, 1.13
No. of reflections	3503
No. of parameters	251
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.37, −0.26
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ), Mercury (Macrae, et al., 2008 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1874902

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314618015006/hb4263sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618015006/hb4263Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618015006/hb4263Isup3.cdx

Supporting information file. DOI: https://doi.org/10.1107/S2414314618015006/hb4263Isup4.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: Mercury (Macrae, et al., 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

2-Amino-5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one top

Crystal data top

C₆H₇N₅O	Z = 4
M_r = 165.17	F(000) = 344
Triclinic, P1	D_x = 1.545 Mg m⁻³
a = 6.5921 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3935 (18) Å	Cell parameters from 3414 reflections
c = 13.185 (3) Å	θ = 2.5–29.0°
α = 92.023 (3)°	µ = 0.12 mm⁻¹
β = 98.309 (3)°	T = 100 K
γ = 99.741 (3)°	Column, colourless
V = 710.1 (3) Å³	0.39 × 0.16 × 0.09 mm

Data collection top

Bruker SMART APEX CCD diffractometer	3503 independent reflections
Radiation source: fine-focus sealed tube	2743 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.023
Detector resolution: 8.3333 pixels mm^-1	θ_max = 29.3°, θ_min = 1.6°
ω scans	h = −9→8
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −11→11
T_min = 0.96, T_max = 0.99	l = −18→18
6817 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.045	Hydrogen site location: mixed
wR(F²) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ²(F_o²) + (0.0848P)²] where P = (F_o² + 2F_c²)/3
3503 reflections	(Δ/σ)_max = 0.002
251 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Special details top

Experimental. The diffraction data were collected in three sets of 363 frames (0.5° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The hydrogens attached to C1 and C7 did not refine well as independent atoms and so were included as riding contributions in idealized positions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	0.71873 (17)	0.15324 (13)	0.67848 (8)	0.0266 (3)
N1	0.45726 (19)	0.26128 (14)	0.39710 (9)	0.0185 (3)
H1	0.396 (4)	0.275 (2)	0.3374 (17)	0.047 (6)*
N2	0.22945 (19)	0.38112 (14)	0.49382 (9)	0.0185 (3)
N3	0.38526 (19)	0.32482 (14)	0.65319 (9)	0.0185 (3)
H3	0.833 (3)	0.097 (2)	0.5008 (14)	0.038 (5)*
N4	0.48312 (19)	0.26943 (14)	0.57606 (9)	0.0172 (3)
N5	0.0991 (2)	0.46038 (16)	0.64373 (10)	0.0222 (3)
H5A	0.000 (3)	0.501 (2)	0.5988 (15)	0.037 (5)*
H5B	0.090 (3)	0.444 (2)	0.7087 (15)	0.027 (5)*
C1	0.6963 (3)	0.1426 (2)	0.30516 (12)	0.0264 (4)
H1A	0.781469	0.238609	0.283004	0.040*
H1B	0.574460	0.105785	0.252660	0.040*
H1C	0.779082	0.056198	0.314946	0.040*
C2	0.6262 (2)	0.18420 (17)	0.40412 (11)	0.0201 (3)
C3	0.7210 (2)	0.14891 (18)	0.49694 (12)	0.0210 (3)
C4	0.6514 (2)	0.18617 (17)	0.59172 (11)	0.0200 (3)
C5	0.2336 (2)	0.38926 (17)	0.59923 (10)	0.0180 (3)
C6	0.3869 (2)	0.30546 (17)	0.48365 (10)	0.0170 (3)
O2	0.09921 (16)	0.38683 (13)	−0.13731 (7)	0.0218 (3)
N6	0.37698 (19)	0.56222 (14)	0.14978 (9)	0.0173 (3)
H6	0.438 (3)	0.602 (2)	0.2170 (15)	0.035 (5)*
N7	0.24807 (18)	0.29027 (14)	0.19538 (9)	0.0172 (3)
N8	0.09267 (18)	0.19333 (14)	0.03227 (9)	0.0166 (3)
N9	0.18460 (18)	0.35493 (14)	0.03384 (8)	0.0153 (3)
N10	0.0637 (2)	0.01587 (16)	0.16497 (10)	0.0197 (3)
H10A	0.123 (3)	−0.015 (2)	0.2218 (14)	0.023 (4)*
H10B	0.013 (3)	−0.060 (2)	0.1197 (14)	0.022 (4)*
C7	0.4936 (3)	0.83306 (18)	0.09981 (12)	0.0231 (3)
H7A	0.530492	0.885495	0.038129	0.035*
H7B	0.620513	0.831601	0.148471	0.035*
H7C	0.402030	0.893396	0.131765	0.035*
C8	0.3836 (2)	0.66345 (17)	0.07097 (11)	0.0173 (3)
C9	0.2924 (2)	0.61062 (18)	−0.02650 (11)	0.0180 (3)
H9	0.301 (3)	0.6893 (19)	−0.0810 (13)	0.019 (4)*
C10	0.1855 (2)	0.44763 (18)	−0.05244 (11)	0.0175 (3)
C11	0.1343 (2)	0.16154 (17)	0.13023 (10)	0.0161 (3)
C12	0.2755 (2)	0.40717 (17)	0.13117 (10)	0.0155 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0288 (6)	0.0339 (6)	0.0171 (5)	0.0087 (5)	−0.0021 (4)	0.0072 (5)
N1	0.0235 (7)	0.0199 (6)	0.0107 (6)	0.0020 (5)	0.0003 (5)	0.0009 (5)
N2	0.0223 (6)	0.0202 (6)	0.0115 (6)	0.0019 (5)	0.0001 (5)	0.0015 (5)
N3	0.0234 (6)	0.0201 (6)	0.0116 (6)	0.0033 (5)	0.0013 (5)	0.0012 (5)
N4	0.0217 (6)	0.0174 (6)	0.0116 (6)	0.0024 (5)	0.0011 (5)	0.0012 (4)
N5	0.0278 (7)	0.0288 (7)	0.0113 (6)	0.0090 (6)	0.0023 (5)	0.0031 (5)
C1	0.0305 (9)	0.0275 (8)	0.0208 (8)	0.0034 (7)	0.0054 (6)	−0.0010 (6)
C2	0.0211 (7)	0.0179 (7)	0.0196 (7)	−0.0017 (6)	0.0034 (6)	−0.0006 (5)
C3	0.0209 (7)	0.0214 (7)	0.0200 (7)	0.0039 (6)	0.0009 (6)	0.0004 (6)
C4	0.0221 (7)	0.0182 (7)	0.0175 (7)	0.0003 (6)	−0.0007 (6)	0.0020 (5)
C5	0.0234 (7)	0.0157 (7)	0.0125 (7)	−0.0006 (6)	−0.0003 (5)	0.0009 (5)
C6	0.0207 (7)	0.0159 (7)	0.0116 (6)	−0.0019 (5)	−0.0010 (5)	0.0004 (5)
O2	0.0242 (5)	0.0295 (6)	0.0108 (5)	0.0044 (4)	−0.0005 (4)	0.0005 (4)
N6	0.0194 (6)	0.0203 (6)	0.0113 (6)	0.0036 (5)	0.0001 (5)	−0.0006 (5)
N7	0.0197 (6)	0.0193 (6)	0.0117 (6)	0.0032 (5)	0.0002 (5)	0.0005 (4)
N8	0.0180 (6)	0.0182 (6)	0.0130 (6)	0.0029 (5)	0.0004 (5)	0.0018 (4)
N9	0.0168 (6)	0.0190 (6)	0.0098 (6)	0.0037 (5)	0.0008 (4)	0.0003 (4)
N10	0.0268 (7)	0.0184 (6)	0.0122 (6)	0.0019 (5)	−0.0008 (5)	0.0023 (5)
C7	0.0312 (8)	0.0185 (7)	0.0195 (7)	0.0033 (6)	0.0052 (6)	0.0001 (6)
C8	0.0183 (7)	0.0197 (7)	0.0158 (7)	0.0069 (5)	0.0044 (5)	0.0025 (5)
C9	0.0208 (7)	0.0216 (7)	0.0135 (7)	0.0075 (6)	0.0034 (5)	0.0033 (5)
C10	0.0166 (7)	0.0257 (8)	0.0121 (6)	0.0082 (6)	0.0029 (5)	0.0029 (5)
C11	0.0157 (6)	0.0205 (7)	0.0126 (6)	0.0051 (5)	0.0017 (5)	0.0007 (5)
C12	0.0157 (6)	0.0205 (7)	0.0105 (6)	0.0054 (5)	0.0003 (5)	−0.0001 (5)

Geometric parameters (Å, º) top

O1—C4	1.2244 (17)	O2—C10	1.2301 (17)
N1—C6	1.3549 (18)	N6—C12	1.3553 (18)
N1—C2	1.373 (2)	N6—C8	1.3662 (18)
N1—H1	0.85 (2)	N6—H6	0.944 (19)
N2—C6	1.3252 (19)	N7—C12	1.3247 (18)
N2—C5	1.3850 (18)	N7—C11	1.3934 (18)
N3—C5	1.3425 (18)	N8—C11	1.3272 (17)
N3—N4	1.3871 (16)	N8—N9	1.3869 (16)
N4—C6	1.3586 (18)	N9—C12	1.3592 (17)
N4—C4	1.4028 (19)	N9—C10	1.4009 (18)
N5—C5	1.339 (2)	N10—C11	1.3528 (19)
N5—H5A	0.93 (2)	N10—H10A	0.863 (18)
N5—H5B	0.881 (18)	N10—H10B	0.845 (18)
C1—C2	1.495 (2)	C7—C8	1.493 (2)
C1—H1A	0.9800	C7—H7A	0.9800
C1—H1B	0.9800	C7—H7B	0.9800
C1—H1C	0.9800	C7—H7C	0.9800
C2—C3	1.358 (2)	C8—C9	1.362 (2)
C3—C4	1.434 (2)	C9—C10	1.434 (2)
C3—H3	0.92 (2)	C9—H9	0.994 (16)

C6—N1—C2	119.78 (12)	C12—N6—C8	119.56 (12)
C6—N1—H1	122.1 (14)	C12—N6—H6	120.7 (11)
C2—N1—H1	118.0 (14)	C8—N6—H6	119.7 (11)
C6—N2—C5	102.16 (12)	C12—N7—C11	101.97 (11)
C5—N3—N4	101.88 (11)	C11—N8—N9	101.91 (11)
C6—N4—N3	109.13 (11)	C12—N9—N8	109.40 (11)
C6—N4—C4	125.85 (12)	C12—N9—C10	125.84 (13)
N3—N4—C4	125.00 (11)	N8—N9—C10	124.76 (11)
C5—N5—H5A	115.3 (12)	C11—N10—H10A	121.1 (11)
C5—N5—H5B	118.1 (12)	C11—N10—H10B	116.2 (12)
H5A—N5—H5B	124.6 (16)	H10A—N10—H10B	114.5 (16)
C2—C1—H1A	109.5	C8—C7—H7A	109.5
C2—C1—H1B	109.5	C8—C7—H7B	109.5
H1A—C1—H1B	109.5	H7A—C7—H7B	109.5
C2—C1—H1C	109.5	C8—C7—H7C	109.5
H1A—C1—H1C	109.5	H7A—C7—H7C	109.5
H1B—C1—H1C	109.5	H7B—C7—H7C	109.5
C3—C2—N1	120.58 (14)	C9—C8—N6	121.13 (13)
C3—C2—C1	123.06 (14)	C9—C8—C7	123.36 (13)
N1—C2—C1	116.36 (13)	N6—C8—C7	115.51 (12)
C2—C3—C4	123.05 (14)	C8—C9—C10	122.51 (13)
C2—C3—H3	119.9 (12)	C8—C9—H9	118.0 (9)
C4—C3—H3	117.0 (12)	C10—C9—H9	119.5 (9)
O1—C4—N4	120.04 (14)	O2—C10—N9	120.15 (14)
O1—C4—C3	128.36 (15)	O2—C10—C9	128.04 (14)
N4—C4—C3	111.60 (12)	N9—C10—C9	111.81 (12)
N5—C5—N3	122.72 (13)	N8—C11—N10	122.11 (13)
N5—C5—N2	122.06 (13)	N8—C11—N7	115.47 (12)
N3—C5—N2	115.20 (13)	N10—C11—N7	122.36 (13)
N2—C6—N1	129.32 (13)	N7—C12—N6	129.63 (12)
N2—C6—N4	111.63 (12)	N7—C12—N9	111.24 (12)
N1—C6—N4	119.05 (13)	N6—C12—N9	119.13 (12)

C5—N3—N4—C6	0.68 (14)	C11—N8—N9—C12	0.65 (14)
C5—N3—N4—C4	−177.92 (13)	C11—N8—N9—C10	179.64 (12)
C6—N1—C2—C3	1.3 (2)	C12—N6—C8—C9	−0.9 (2)
C6—N1—C2—C1	−178.81 (13)	C12—N6—C8—C7	178.26 (12)
N1—C2—C3—C4	1.0 (2)	N6—C8—C9—C10	−0.2 (2)
C1—C2—C3—C4	−178.83 (13)	C7—C8—C9—C10	−179.29 (13)
C6—N4—C4—O1	−176.24 (13)	C12—N9—C10—O2	179.35 (13)
N3—N4—C4—O1	2.1 (2)	N8—N9—C10—O2	0.5 (2)
C6—N4—C4—C3	3.1 (2)	C12—N9—C10—C9	−1.25 (19)
N3—N4—C4—C3	−178.51 (12)	N8—N9—C10—C9	179.92 (11)
C2—C3—C4—O1	176.27 (15)	C8—C9—C10—O2	−179.49 (14)
C2—C3—C4—N4	−3.0 (2)	C8—C9—C10—N9	1.17 (19)
N4—N3—C5—N5	−179.14 (13)	N9—N8—C11—N10	176.94 (12)
N4—N3—C5—N2	−0.87 (15)	N9—N8—C11—N7	−0.47 (15)
C6—N2—C5—N5	178.99 (13)	C12—N7—C11—N8	0.11 (16)
C6—N2—C5—N3	0.71 (16)	C12—N7—C11—N10	−177.30 (13)
C5—N2—C6—N1	179.09 (14)	C11—N7—C12—N6	−179.56 (13)
C5—N2—C6—N4	−0.21 (15)	C11—N7—C12—N9	0.33 (15)
C2—N1—C6—N2	179.42 (13)	C8—N6—C12—N7	−179.24 (14)
C2—N1—C6—N4	−1.3 (2)	C8—N6—C12—N9	0.89 (19)
N3—N4—C6—N2	−0.30 (16)	N8—N9—C12—N7	−0.64 (15)
C4—N4—C6—N2	178.28 (12)	C10—N9—C12—N7	−179.62 (12)
N3—N4—C6—N1	−179.69 (11)	N8—N9—C12—N6	179.26 (11)
C4—N4—C6—N1	−1.1 (2)	C10—N9—C12—N6	0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7	0.85 (2)	2.00 (2)	2.8520 (18)	176 (2)
N5—H5A···N2ⁱ	0.93 (2)	2.20 (2)	3.1240 (18)	173.3 (17)
N5—H5B···O2ⁱⁱ	0.881 (18)	2.097 (19)	2.9733 (18)	172.7 (16)
N6—H6···N3ⁱⁱⁱ	0.944 (19)	1.94 (2)	2.8724 (17)	168.6 (17)
N10—H10A···O1^iv	0.863 (18)	2.069 (18)	2.8935 (17)	159.5 (16)
N10—H10B···N8^v	0.845 (18)	2.220 (19)	3.0330 (19)	161.2 (16)

Symmetry codes: (i) −x, −y+1, −z+1; (ii) x, y, z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y, −z+1; (v) −x, −y, −z.

Acknowledgements

JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.

References

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IUCrDATA

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Volume 3| Part 11| November 2018| x181500

https://doi.org/10.1107/S2414314618015006

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

2-Amino-5-methyl-1,2,4-triazolo[1,5-a]pyrimidin-7(4H)-one

Structure description

Synthesis and crystallization

Refinement

Structural data

Acknowledgements

References

organic compounds