N-(1H-1,2,4-Triazol-5-yl)pyridine-2-carboxamide.

In the structure of the title compound, C(8)H(7)N(5)O, the pyridine ring and the imidazole ring are nearly coplanar, making a dihedral angle of 2.97 (15)°. An intra-molecular N-H⋯O hydrogen bond occurs. In the crystal mol-ecules are connected by inter-molecular hydrogen bonds and π-π stacking inter-actions between neighboring imidazole rings [centroid-centroid distance = 3.5842 (5) Å and off-set angle = 21.77°], leading to the formation of a two-dimensional supra-molecular sheet.

Related literature

For an alternative preparative method for the title compound, see: Browne & Polya (1968 ▶). For the potential bioinorganic applications of 1,2,4-triazole derivatives, see: Bohm & Karow (1981 ▶); Bahel et al. (1984 ▶).

Experimental

Crystal data

C8H7N5O

M = 189.19

Monoclinic,

a = 8.6906 (17) Å

b = 5.2854 (10) Å

c = 17.880 (4) Å

β = 90.700 (3)°

V = 821.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 273 K

0.26 × 0.24 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.972, T max = 0.980

3938 measured reflections

1443 independent reflections

961 reflections with I > 2σ(I)

R int = 0.095

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.106

S = 1.00

1443 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809041269/ez2185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041269/ez2185Isup2.hkl

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

C8H7N5O	F(000) = 392
Mr = 189.19	Dx = 1.530 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1623 reflections
a = 8.6906 (17) Å	θ = 3.0–28.0°
b = 5.2854 (10) Å	µ = 0.11 mm−1
c = 17.880 (4) Å	T = 273 K
β = 90.700 (3)°	Block, colorless
V = 821.2 (3) Å3	0.26 × 0.24 × 0.18 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	1443 independent reflections
Radiation source: fine-focus sealed tube	961 reflections with I > 2σ(I)
graphite	Rint = 0.095
φ and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −8→10
Tmin = 0.972, Tmax = 0.980	k = −6→5
3938 measured reflections	l = −21→21

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.106	w = 1/[σ2(Fo2) + (0.0259P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1443 reflections	Δρmax = 0.17 e Å−3
128 parameters	Δρmin = −0.16 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: 0.024 (3)

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
N1	0.6956 (2)	0.7443 (3)	0.35815 (9)	0.0470 (5)
N2	0.77449 (17)	0.4023 (3)	0.46730 (8)	0.0410 (5)
H21	0.8406	0.5181	0.4539	0.061*
C5	0.5911 (2)	0.5707 (4)	0.37611 (10)	0.0389 (5)
C6	0.6318 (2)	0.3877 (4)	0.43697 (10)	0.0391 (5)
N4	0.74724 (18)	0.0445 (3)	0.54961 (8)	0.0438 (5)
H41	0.6579	−0.0130	0.5370	0.066*
N5	0.83128 (19)	−0.0771 (3)	0.60411 (9)	0.0481 (5)
N3	0.96153 (18)	0.2595 (3)	0.55752 (9)	0.0454 (5)
C3	0.4141 (3)	0.7178 (5)	0.28387 (12)	0.0529 (7)
H3	0.3198	0.7083	0.2589	0.063*
C4	0.4492 (2)	0.5512 (4)	0.34098 (11)	0.0478 (6)
H4	0.3789	0.4286	0.3555	0.057*
C1	0.6574 (3)	0.9042 (4)	0.30331 (12)	0.0547 (6)
H1	0.7281	1.0284	0.2905	0.066*
C7	0.8255 (2)	0.2395 (4)	0.52329 (11)	0.0380 (5)
C2	0.5196 (3)	0.8965 (5)	0.26449 (12)	0.0534 (7)
H2	0.4990	1.0104	0.2260	0.064*
C8	0.9568 (2)	0.0599 (4)	0.60561 (11)	0.0490 (6)
H8	1.0385	0.0229	0.6379	0.059*
O1	0.53795 (16)	0.2298 (3)	0.45747 (8)	0.0520 (5)

	U11	U22	U33	U12	U13	U23
N1	0.0448 (11)	0.0521 (13)	0.0439 (10)	−0.0024 (9)	−0.0056 (8)	0.0052 (10)
N2	0.0348 (10)	0.0466 (12)	0.0414 (10)	−0.0067 (8)	−0.0051 (8)	0.0074 (9)
C5	0.0382 (12)	0.0424 (13)	0.0360 (11)	0.0004 (10)	−0.0015 (9)	−0.0021 (10)
C6	0.0346 (11)	0.0436 (14)	0.0390 (12)	−0.0060 (10)	−0.0031 (9)	−0.0033 (10)
N4	0.0371 (10)	0.0510 (13)	0.0431 (10)	−0.0086 (9)	−0.0042 (8)	0.0068 (9)
N5	0.0419 (10)	0.0541 (13)	0.0481 (10)	−0.0055 (10)	−0.0077 (8)	0.0132 (9)
N3	0.0391 (10)	0.0500 (12)	0.0469 (10)	−0.0077 (9)	−0.0092 (8)	0.0089 (9)
C3	0.0490 (14)	0.0611 (18)	0.0482 (13)	0.0082 (12)	−0.0150 (11)	−0.0033 (12)
C4	0.0438 (13)	0.0529 (15)	0.0465 (13)	−0.0028 (11)	−0.0065 (10)	−0.0015 (11)
C1	0.0580 (15)	0.0517 (16)	0.0542 (14)	−0.0055 (12)	−0.0027 (11)	0.0127 (12)
C7	0.0320 (11)	0.0441 (14)	0.0379 (11)	−0.0058 (10)	−0.0014 (9)	−0.0008 (10)
C2	0.0620 (16)	0.0542 (17)	0.0439 (12)	0.0088 (13)	−0.0074 (11)	0.0059 (12)
C8	0.0438 (13)	0.0582 (16)	0.0447 (13)	−0.0034 (12)	−0.0128 (10)	0.0109 (12)
O1	0.0390 (9)	0.0594 (11)	0.0574 (10)	−0.0141 (8)	−0.0100 (7)	0.0117 (8)

N1—C5	1.333 (2)	N5—C8	1.309 (3)
N1—C1	1.333 (3)	N3—C7	1.329 (2)
N2—C6	1.349 (2)	N3—C8	1.362 (2)
N2—C7	1.388 (2)	C3—C2	1.364 (3)
N2—H21	0.8751	C3—C4	1.379 (3)
C5—C4	1.381 (3)	C3—H3	0.9300
C5—C6	1.495 (3)	C4—H4	0.9300
C6—O1	1.226 (2)	C1—C2	1.377 (3)
N4—C7	1.324 (2)	C1—H1	0.9300
N4—N5	1.371 (2)	C2—H2	0.9300
N4—H41	0.8612	C8—H8	0.9300
C5—N1—C1	116.71 (19)	C4—C3—H3	120.4
C6—N2—C7	122.55 (17)	C3—C4—C5	118.5 (2)
C6—N2—H21	122.2	C3—C4—H4	120.7
C7—N2—H21	115.2	C5—C4—H4	120.7
N1—C5—C4	123.29 (19)	N1—C1—C2	124.0 (2)
N1—C5—C6	117.68 (18)	N1—C1—H1	118.0
C4—C5—C6	119.02 (19)	C2—C1—H1	118.0
O1—C6—N2	122.01 (19)	N4—C7—N3	110.85 (18)
O1—C6—C5	120.34 (18)	N4—C7—N2	125.30 (17)
N2—C6—C5	117.65 (18)	N3—C7—N2	123.85 (18)
C7—N4—N5	110.26 (16)	C3—C2—C1	118.4 (2)
C7—N4—H41	130.3	C3—C2—H2	120.8
N5—N4—H41	119.4	C1—C2—H2	120.8
C8—N5—N4	101.06 (17)	N5—C8—N3	116.56 (18)
C7—N3—C8	101.28 (17)	N5—C8—H8	121.7
C2—C3—C4	119.1 (2)	N3—C8—H8	121.7
C2—C3—H3	120.4
C1—N1—C5—C4	0.0 (3)	C5—N1—C1—C2	−1.0 (3)
C1—N1—C5—C6	179.44 (19)	N5—N4—C7—N3	−0.1 (2)
C7—N2—C6—O1	0.4 (3)	N5—N4—C7—N2	179.57 (17)
C7—N2—C6—C5	−178.98 (17)	C8—N3—C7—N4	0.3 (2)
N1—C5—C6—O1	177.46 (18)	C8—N3—C7—N2	−179.40 (19)
C4—C5—C6—O1	−3.1 (3)	C6—N2—C7—N4	4.8 (3)
N1—C5—C6—N2	−3.1 (3)	C6—N2—C7—N3	−175.51 (19)
C4—C5—C6—N2	176.30 (17)	C4—C3—C2—C1	−0.4 (3)
C7—N4—N5—C8	−0.1 (2)	N1—C1—C2—C3	1.2 (4)
C2—C3—C4—C5	−0.5 (3)	N4—N5—C8—N3	0.3 (2)
N1—C5—C4—C3	0.7 (3)	C7—N3—C8—N5	−0.4 (2)
C6—C5—C4—C3	−178.68 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H21···N3i	0.88	2.09	2.946 (2)	164
N4—H41···O1ii	0.86	2.06	2.873 (2)	158
N4—H41···O1	0.86	2.17	2.629 (2)	113

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H21⋯N3i	0.88	2.09	2.946 (2)	164
N4—H41⋯O1ii	0.86	2.06	2.873 (2)	158
N4—H41⋯O1	0.86	2.17	2.629 (2)	113

Symmetry codes: (i) ; (ii) .