3-Pyridin-2-yl-1H-1,2,4-triazol-5-amine.

In the title compound, C(7)H(7)N(5), the non-H atoms are almost coplanar (r.m.s. deviation = 0.050 Å), with the N atom of pyridine ring oriented to the N-N(H) side of the 1,2,4-triazole ring. The mean planes of the pyridine and 1,2,4-triazole rings form a dihedral angle of 5.58 (7)°. The N atom of the amino group adopts a pyramidal configuration. The mol-ecules are linked into a two-dimensional network parallel to (10) by N-H⋯N hydrogen bonds.

Related literature

For 1,2,4-triazol-5-amines as building blocks in the synthesis of fused heterocyclic systems, see: Dolzhenko et al. (2006 ▶, 2007a ▶,b ▶); Fischer, (2007 ▶). For a summary of structural data for 1,2,4-triazoles, see: Buzykin et al. (2006 ▶). For crystal structures of CuII complexes with 3-pyridin-2-yl-1,2,4-triazol-5-amine, see: Ferrer et al. (2004 ▶).

Experimental

Crystal data

C7H7N5

M = 161.18

Monoclinic,

a = 7.3863 (6) Å

b = 7.9096 (6) Å

c = 13.2157 (11) Å

β = 91.832 (2)°

V = 771.70 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 223 (2) K

0.36 × 0.16 × 0.12 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.967, T max = 0.989

5336 measured reflections

1772 independent reflections

1519 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.110

S = 1.05

1772 reflections

121 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.21 e Å−3

Δρmin = −0.20 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); 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 I, global. DOI: 10.1107/S1600536808042177/ci2719sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808042177/ci2719Isup2.hkl

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

C7H7N5	F(000) = 336
Mr = 161.18	Dx = 1.387 Mg m−3
Monoclinic, P21/n	Melting point: 493 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 7.3863 (6) Å	Cell parameters from 1841 reflections
b = 7.9096 (6) Å	θ = 3.0–26.6°
c = 13.2157 (11) Å	µ = 0.10 mm−1
β = 91.832 (2)°	T = 223 K
V = 771.70 (11) Å3	Block, colourless
Z = 4	0.36 × 0.16 × 0.12 mm

Bruker SMART APEX CCD diffractometer	1772 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −9→9
Tmin = 0.967, Tmax = 0.989	k = −8→10
5336 measured reflections	l = −14→17

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1487P] where P = (Fo2 + 2Fc2)/3
1772 reflections	(Δ/σ)max = 0.001
121 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.20 e Å−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	0.72741 (16)	0.34999 (14)	0.68693 (8)	0.0383 (3)
N2	0.66107 (16)	0.19639 (15)	0.71630 (8)	0.0393 (3)
H2N	0.669 (2)	0.164 (2)	0.7817 (14)	0.052 (5)*
N3	0.61324 (14)	0.20352 (14)	0.55193 (8)	0.0345 (3)
N4	0.51489 (16)	−0.04181 (15)	0.64256 (9)	0.0398 (3)
H4A	0.488 (2)	−0.095 (2)	0.5842 (13)	0.049 (4)*
H4B	0.564 (2)	−0.106 (2)	0.6948 (13)	0.050 (4)*
N5	0.80901 (15)	0.62905 (15)	0.56803 (8)	0.0388 (3)
C1	0.69411 (16)	0.34759 (16)	0.58805 (9)	0.0331 (3)
C2	0.59494 (16)	0.11150 (17)	0.63532 (9)	0.0343 (3)
C3	0.74353 (16)	0.48955 (17)	0.52229 (9)	0.0343 (3)
C4	0.72299 (19)	0.47748 (19)	0.41755 (10)	0.0425 (3)
H4	0.6758	0.3786	0.3873	0.051*
C5	0.77288 (19)	0.6128 (2)	0.35870 (11)	0.0491 (4)
H5	0.7598	0.6076	0.2878	0.059*
C6	0.8419 (2)	0.7554 (2)	0.40516 (12)	0.0486 (4)
H6	0.8781	0.8489	0.3668	0.058*
C7	0.85663 (19)	0.75796 (19)	0.50930 (12)	0.0455 (4)
H7	0.9029	0.8561	0.5408	0.055*

	U11	U22	U33	U12	U13	U23
N1	0.0476 (6)	0.0387 (6)	0.0282 (5)	−0.0007 (5)	−0.0076 (4)	0.0006 (4)
N2	0.0518 (7)	0.0392 (6)	0.0261 (6)	−0.0013 (5)	−0.0092 (5)	0.0000 (5)
N3	0.0362 (5)	0.0396 (6)	0.0273 (5)	0.0042 (4)	−0.0059 (4)	−0.0028 (4)
N4	0.0498 (7)	0.0397 (6)	0.0291 (6)	−0.0021 (5)	−0.0110 (5)	−0.0001 (5)
N5	0.0420 (6)	0.0409 (6)	0.0332 (6)	0.0030 (5)	−0.0043 (5)	0.0012 (5)
C1	0.0330 (6)	0.0385 (7)	0.0273 (6)	0.0057 (5)	−0.0056 (5)	−0.0035 (5)
C2	0.0357 (6)	0.0391 (7)	0.0274 (6)	0.0053 (5)	−0.0068 (5)	−0.0030 (5)
C3	0.0305 (6)	0.0419 (7)	0.0301 (6)	0.0076 (5)	−0.0028 (5)	−0.0010 (5)
C4	0.0442 (7)	0.0522 (8)	0.0310 (7)	0.0046 (6)	−0.0016 (5)	−0.0025 (6)
C5	0.0488 (8)	0.0683 (10)	0.0304 (7)	0.0080 (7)	0.0032 (6)	0.0071 (7)
C6	0.0444 (8)	0.0558 (9)	0.0457 (8)	0.0057 (7)	0.0046 (6)	0.0150 (7)
C7	0.0454 (8)	0.0447 (8)	0.0460 (8)	0.0013 (6)	−0.0035 (6)	0.0050 (6)

N1—C1	1.3221 (16)	N5—C3	1.3410 (17)
N1—N2	1.3708 (16)	C1—C3	1.4729 (18)
N2—C2	1.3422 (16)	C3—C4	1.3909 (18)
N2—H2N	0.902 (19)	C4—C5	1.380 (2)
N3—C2	1.3312 (17)	C4—H4	0.94
N3—C1	1.3656 (16)	C5—C6	1.374 (2)
N4—C2	1.3538 (18)	C5—H5	0.94
N4—H4A	0.896 (18)	C6—C7	1.377 (2)
N4—H4B	0.925 (17)	C6—H6	0.94
N5—C7	1.3354 (18)	C7—H7	0.94
C1—N1—N2	102.14 (10)	N5—C3—C4	122.10 (13)
C2—N2—N1	109.99 (11)	N5—C3—C1	116.99 (11)
C2—N2—H2N	129.2 (11)	C4—C3—C1	120.91 (12)
N1—N2—H2N	120.8 (11)	C5—C4—C3	119.01 (14)
C2—N3—C1	102.81 (10)	C5—C4—H4	120.5
C2—N4—H4A	116.4 (10)	C3—C4—H4	120.5
C2—N4—H4B	112.7 (10)	C6—C5—C4	119.12 (14)
H4A—N4—H4B	117.2 (14)	C6—C5—H5	120.4
C7—N5—C3	117.65 (12)	C4—C5—H5	120.4
N1—C1—N3	115.02 (12)	C5—C6—C7	118.36 (14)
N1—C1—C3	122.04 (12)	C5—C6—H6	120.8
N3—C1—C3	122.94 (11)	C7—C6—H6	120.8
N3—C2—N2	110.03 (12)	N5—C7—C6	123.76 (15)
N3—C2—N4	127.19 (11)	N5—C7—H7	118.1
N2—C2—N4	122.71 (12)	C6—C7—H7	118.1

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···N5i	0.90 (2)	2.01 (2)	2.9010 (16)	171 (1)
N4—H4A···N3ii	0.90 (2)	2.11 (2)	2.9971 (16)	172 (1)
N4—H4B···N1i	0.93 (2)	2.19 (2)	3.0264 (16)	151 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯N5i	0.90 (2)	2.01 (2)	2.9010 (16)	171 (1)
N4—H4A⋯N3ii	0.90 (2)	2.11 (2)	2.9971 (16)	172 (1)
N4—H4B⋯N1i	0.93 (2)	2.19 (2)	3.0264 (16)	151 (1)

Symmetry codes: (i) ; (ii) .