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

The title compound, C(8)H(8)N(6)O, 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 ▶); Olguín et al. (2012 ▶). For related triazole structures, see: Allouch et al. (2008 ▶); Ouakkaf et al. (2011 ▶). For structures of metal complexes with related triazoles, see: Ferrer et al. (2004 ▶, 2012 ▶). For the synthesis of triazoles, see: Chernyshev et al. (2005 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C8H8N6O

M = 204.20

Tetragonal,

a = 9.5480 (5) Å

c = 21.9570 (9) Å

V = 2001.69 (17) Å3

Z = 8

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.107

S = 1.07

1407 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.13 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and DIAMOND (Brandenburg & Putz, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813000123/gk2547sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813000123/gk2547Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813000123/gk2547Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H8N6O	Dx = 1.355 Mg m−3
Mr = 204.20	Melting point: 494(1) K
Tetragonal, P41212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4abw 2nw	Cell parameters from 2353 reflections
a = 9.5480 (5) Å	θ = 1.0–27.5°
c = 21.9570 (9) Å	µ = 0.10 mm−1
V = 2001.69 (17) Å3	T = 293 K
Z = 8	Prism, colourless
F(000) = 848	0.15 × 0.09 × 0.05 mm

Nonius KappaCCD diffractometer	915 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.048
Graphite monochromator	θmax = 27.5°, θmin = 2.3°
Detector resolution: 9 pixels mm-1	h = −12→12
ω and phi scans	k = −8→8
4484 measured reflections	l = −28→27
1407 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038	H-atom parameters constrained
wR(F2) = 0.107	w = 1/[σ2(Fo2) + (0.0557P)2 + 0.0085P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
1407 reflections	Δρmax = 0.12 e Å−3
137 parameters	Δρmin = −0.13 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.013 (2)

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

	x	y	z	Uiso*/Ueq
O17	0.1793 (2)	0.33529 (18)	0.25244 (8)	0.0726 (6)
N11	0.0462 (3)	0.1210 (3)	0.36912 (9)	0.0708 (7)
N18	0.1596 (2)	0.09855 (19)	0.25946 (8)	0.0513 (5)
H18	0.1399	0.0318	0.2843	0.062*
N20	0.2076 (2)	−0.0746 (2)	0.18712 (8)	0.0495 (5)
N21	0.2450 (2)	−0.0695 (2)	0.12653 (8)	0.0503 (5)
H21	0.2593	−0.1412	0.1036	0.060*
N22	0.2887 (3)	0.1049 (2)	0.05253 (9)	0.0797 (9)
H22A	0.3046	0.0438	0.0246	0.096*
H22B	0.2939	0.1928	0.0442	0.096*
N23	0.2279 (2)	0.14920 (19)	0.15549 (8)	0.0543 (6)
C12	−0.0006 (4)	0.1273 (4)	0.42633 (13)	0.0885 (11)
H12	−0.0387	0.0467	0.4434	0.106*
C13	0.0043 (4)	0.2465 (4)	0.46156 (14)	0.0871 (10)
H13	−0.0288	0.2460	0.5014	0.104*
C14	0.0583 (5)	0.3637 (4)	0.43690 (15)	0.1011 (12)
H14	0.0627	0.4458	0.4596	0.121*
C15	0.1072 (4)	0.3613 (3)	0.37768 (13)	0.0877 (11)
H15	0.1451	0.4412	0.3599	0.105*
C16	0.0983 (3)	0.2377 (3)	0.34567 (11)	0.0585 (7)
C17	0.1488 (3)	0.2302 (3)	0.28160 (11)	0.0541 (6)
C19	0.1992 (2)	0.0590 (2)	0.20093 (10)	0.0463 (6)
C22	0.2557 (3)	0.0633 (2)	0.10904 (10)	0.0503 (6)

	U11	U22	U33	U12	U13	U23
O17	0.1132 (17)	0.0408 (10)	0.0639 (11)	−0.0008 (10)	0.0054 (11)	0.0032 (9)
N11	0.0937 (19)	0.0633 (16)	0.0552 (13)	−0.0053 (13)	0.0148 (12)	−0.0079 (11)
N18	0.0701 (14)	0.0370 (11)	0.0468 (11)	−0.0015 (10)	0.0061 (10)	−0.0016 (9)
N20	0.0677 (14)	0.0356 (11)	0.0453 (10)	0.0003 (9)	0.0062 (9)	−0.0003 (9)
N21	0.0723 (14)	0.0345 (11)	0.0442 (10)	0.0013 (10)	0.0061 (9)	−0.0020 (8)
N22	0.147 (3)	0.0395 (13)	0.0522 (13)	0.0045 (14)	0.0264 (15)	0.0046 (10)
N23	0.0790 (15)	0.0351 (10)	0.0487 (11)	−0.0009 (10)	0.0068 (11)	0.0014 (9)
C12	0.115 (3)	0.085 (2)	0.0647 (18)	−0.010 (2)	0.0275 (18)	−0.0075 (17)
C13	0.104 (3)	0.093 (3)	0.0643 (18)	0.014 (2)	0.0149 (17)	−0.0163 (19)
C14	0.148 (4)	0.080 (3)	0.076 (2)	0.018 (3)	0.009 (2)	−0.033 (2)
C15	0.136 (3)	0.0541 (19)	0.073 (2)	0.0064 (19)	0.0134 (19)	−0.0150 (16)
C16	0.0715 (18)	0.0512 (17)	0.0528 (14)	0.0080 (13)	0.0001 (12)	−0.0059 (13)
C17	0.0664 (16)	0.0402 (14)	0.0558 (14)	0.0025 (12)	−0.0052 (12)	−0.0005 (12)
C19	0.0576 (15)	0.0364 (13)	0.0448 (13)	−0.0009 (11)	0.0011 (11)	0.0022 (10)
C22	0.0686 (17)	0.0355 (13)	0.0468 (13)	−0.0007 (12)	0.0043 (12)	−0.0005 (11)

O17—C17	1.225 (3)	N22—H22B	0.8600
N11—C16	1.324 (3)	N23—C22	1.335 (3)
N11—C12	1.335 (3)	N23—C19	1.347 (3)
N18—C17	1.352 (3)	C12—C13	1.377 (4)
N18—C19	1.392 (3)	C12—H12	0.9300
N18—H18	0.8600	C13—C14	1.346 (5)
N20—C19	1.314 (3)	C13—H13	0.9300
N20—N21	1.378 (2)	C14—C15	1.382 (4)
N21—C22	1.329 (3)	C14—H14	0.9300
N21—H21	0.8600	C15—C16	1.376 (4)
N22—C22	1.340 (3)	C15—H15	0.9300
N22—H22A	0.8600	C16—C17	1.489 (3)
C16—N11—C12	117.0 (2)	C13—C14—C15	119.6 (3)
C17—N18—C19	127.3 (2)	C13—C14—H14	120.2
C17—N18—H18	116.4	C15—C14—H14	120.2
C19—N18—H18	116.3	C16—C15—C14	118.3 (3)
C19—N20—N21	101.78 (18)	C16—C15—H15	120.9
C22—N21—N20	109.41 (18)	C14—C15—H15	120.9
C22—N21—H21	125.3	N11—C16—C15	123.1 (2)
N20—N21—H21	125.3	N11—C16—C17	116.7 (2)
C22—N22—H22A	120.0	C15—C16—C17	120.2 (3)
C22—N22—H22B	120.0	O17—C17—N18	123.7 (2)
H22A—N22—H22B	120.0	O17—C17—C16	122.1 (2)
C22—N23—C19	102.32 (19)	N18—C17—C16	114.1 (2)
N11—C12—C13	123.7 (3)	N20—C19—N23	116.0 (2)
N11—C12—H12	118.1	N20—C19—N18	119.6 (2)
C13—C12—H12	118.1	N23—C19—N18	124.4 (2)
C14—C13—C12	118.3 (3)	N21—C22—N23	110.5 (2)
C14—C13—H13	120.8	N21—C22—N22	124.6 (2)
C12—C13—H13	120.8	N23—C22—N22	124.9 (2)
C19—N20—N21—C22	−0.1 (3)	N11—C16—C17—N18	−12.1 (4)
C16—N11—C12—C13	−0.8 (6)	C15—C16—C17—N18	167.8 (3)
N11—C12—C13—C14	0.6 (6)	N21—N20—C19—N23	−0.2 (3)
C12—C13—C14—C15	−0.2 (6)	N21—N20—C19—N18	178.5 (2)
C13—C14—C15—C16	0.2 (5)	C22—N23—C19—N20	0.5 (3)
C12—N11—C16—C15	0.8 (5)	C22—N23—C19—N18	−178.2 (2)
C12—N11—C16—C17	−179.3 (3)	C17—N18—C19—N20	178.4 (2)
C14—C15—C16—N11	−0.5 (5)	C17—N18—C19—N23	−3.0 (4)
C14—C15—C16—C17	179.6 (3)	N20—N21—C22—N23	0.4 (3)
C19—N18—C17—O17	−3.3 (4)	N20—N21—C22—N22	−179.1 (3)
C19—N18—C17—C16	177.7 (2)	C19—N23—C22—N21	−0.5 (3)
N11—C16—C17—O17	168.9 (3)	C19—N23—C22—N22	179.0 (3)
C15—C16—C17—O17	−11.3 (4)

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

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) ; (ii) ; (iii) .