4-(1,2,4-Triazol-1-yl)aniline.

In the title compound, C(8)H(8)N(4), the dihedral angle between the triazole ring [maximum deviation = 0.003 (1) Å] and the benzene ring is 34.57 (7)°. In the crystal, mol-ecules are linked into sheets lying parallel to the ac plane via inter-molecular N-H⋯N and C-H⋯N hydrogen bonds. Aromatic π-π [centroid-centroid distance = 3.6750 (8) Å] stacking and N-H⋯π inter-actions are also observed.

Related literature

For general background to and the biological activity of triazole derivatives, see: Isloor et al. (2000 ▶, 2009 ▶); Soliman et al. (2001 ▶); Holla et al. (2000 ▶); Sunil et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For a related structure, see: Fun et al. (2010 ▶).

Experimental

Crystal data

C8H8N4

M = 160.18

Monoclinic,

a = 5.5488 (1) Å

b = 7.3656 (2) Å

c = 19.5477 (5) Å

β = 99.416 (2)°

V = 788.15 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.50 × 0.42 × 0.14 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.957, T max = 0.988

8036 measured reflections

2160 independent reflections

1722 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.05

2160 reflections

110 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052025/hb5764sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052025/hb5764Isup2.hkl

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

C8H8N4	F(000) = 336
Mr = 160.18	Dx = 1.350 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3245 reflections
a = 5.5488 (1) Å	θ = 3.0–29.1°
b = 7.3656 (2) Å	µ = 0.09 mm−1
c = 19.5477 (5) Å	T = 296 K
β = 99.416 (2)°	Block, yellow
V = 788.15 (3) Å3	0.50 × 0.42 × 0.14 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2160 independent reflections
Radiation source: fine-focus sealed tube	1722 reflections with I > 2σ(I)
graphite	Rint = 0.030
φ and ω scans	θmax = 29.4°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −7→7
Tmin = 0.957, Tmax = 0.988	k = −10→10
8036 measured reflections	l = −26→24

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)] = 0.044	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.118	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.1531P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2160 reflections	Δρmax = 0.23 e Å−3
110 parameters	Δρmin = −0.17 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (5)

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.

	x	y	z	Uiso*/Ueq
N1	0.3298 (2)	0.17124 (18)	1.08332 (6)	0.0542 (3)
N2	0.58582 (19)	0.24895 (17)	1.00992 (6)	0.0498 (3)
N3	0.34993 (17)	0.26004 (14)	0.97774 (5)	0.0378 (3)
N4	0.0895 (3)	0.4820 (2)	0.70184 (6)	0.0597 (4)
C1	0.2029 (2)	0.2126 (2)	1.02227 (7)	0.0480 (3)
H1A	0.0334	0.2092	1.0117	0.058*
C2	0.5611 (3)	0.1960 (2)	1.07255 (7)	0.0533 (4)
H2A	0.6948	0.1768	1.1072	0.064*
C3	0.2865 (2)	0.31773 (16)	0.90734 (6)	0.0360 (3)
C4	0.4336 (2)	0.27300 (17)	0.85909 (6)	0.0411 (3)
H4A	0.5752	0.2056	0.8724	0.049*
C5	0.3691 (2)	0.32893 (18)	0.79107 (6)	0.0432 (3)
H5A	0.4686	0.2986	0.7589	0.052*
C6	0.1573 (2)	0.43007 (17)	0.76988 (6)	0.0404 (3)
C7	0.0123 (2)	0.47403 (17)	0.81966 (6)	0.0434 (3)
H7A	−0.1296	0.5415	0.8068	0.052*
C8	0.0763 (2)	0.41891 (17)	0.88743 (6)	0.0415 (3)
H8A	−0.0218	0.4496	0.9200	0.050*
H2N4	0.171 (3)	0.447 (2)	0.6697 (8)	0.065 (5)*
H1N4	−0.029 (3)	0.560 (3)	0.6921 (9)	0.078 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0549 (7)	0.0658 (8)	0.0435 (6)	0.0049 (6)	0.0124 (5)	0.0063 (5)
N2	0.0340 (5)	0.0681 (8)	0.0452 (6)	−0.0015 (5)	0.0006 (4)	0.0051 (5)
N3	0.0318 (5)	0.0448 (5)	0.0367 (5)	0.0009 (4)	0.0052 (4)	−0.0009 (4)
N4	0.0711 (8)	0.0683 (9)	0.0406 (6)	0.0212 (7)	0.0116 (6)	0.0085 (6)
C1	0.0392 (6)	0.0616 (8)	0.0447 (7)	0.0024 (6)	0.0115 (5)	0.0042 (6)
C2	0.0485 (7)	0.0650 (9)	0.0439 (7)	0.0014 (6)	−0.0002 (6)	0.0047 (6)
C3	0.0324 (5)	0.0396 (6)	0.0355 (6)	−0.0019 (4)	0.0043 (4)	−0.0023 (4)
C4	0.0313 (5)	0.0480 (7)	0.0445 (7)	0.0041 (5)	0.0074 (5)	−0.0005 (5)
C5	0.0388 (6)	0.0518 (7)	0.0412 (6)	0.0008 (5)	0.0133 (5)	−0.0019 (5)
C6	0.0427 (6)	0.0395 (6)	0.0386 (6)	−0.0027 (5)	0.0051 (5)	−0.0006 (5)
C7	0.0388 (6)	0.0453 (7)	0.0451 (7)	0.0081 (5)	0.0042 (5)	−0.0005 (5)
C8	0.0375 (6)	0.0468 (7)	0.0413 (6)	0.0053 (5)	0.0096 (5)	−0.0049 (5)

N1—C1	1.3183 (17)	C3—C4	1.3842 (16)
N1—C2	1.3468 (19)	C3—C8	1.3851 (16)
N2—C2	1.3134 (18)	C4—C5	1.3821 (17)
N2—N3	1.3587 (14)	C4—H4A	0.9300
N3—C1	1.3332 (16)	C5—C6	1.3957 (17)
N3—C3	1.4284 (14)	C5—H5A	0.9300
N4—C6	1.3758 (16)	C6—C7	1.3987 (17)
N4—H2N4	0.871 (18)	C7—C8	1.3755 (16)
N4—H1N4	0.87 (2)	C7—H7A	0.9300
C1—H1A	0.9300	C8—H8A	0.9300
C2—H2A	0.9300
C1—N1—C2	102.04 (11)	C8—C3—N3	119.62 (10)
C2—N2—N3	102.11 (11)	C5—C4—C3	119.72 (11)
C1—N3—N2	109.16 (10)	C5—C4—H4A	120.1
C1—N3—C3	128.78 (10)	C3—C4—H4A	120.1
N2—N3—C3	122.06 (10)	C4—C5—C6	121.17 (11)
C6—N4—H2N4	121.5 (11)	C4—C5—H5A	119.4
C6—N4—H1N4	118.2 (12)	C6—C5—H5A	119.4
H2N4—N4—H1N4	120.1 (16)	N4—C6—C5	121.27 (12)
N1—C1—N3	111.01 (12)	N4—C6—C7	120.72 (12)
N1—C1—H1A	124.5	C5—C6—C7	118.00 (11)
N3—C1—H1A	124.5	C8—C7—C6	120.95 (11)
N2—C2—N1	115.69 (12)	C8—C7—H7A	119.5
N2—C2—H2A	122.2	C6—C7—H7A	119.5
N1—C2—H2A	122.2	C7—C8—C3	120.16 (11)
C4—C3—C8	120.00 (11)	C7—C8—H8A	119.9
C4—C3—N3	120.38 (10)	C3—C8—H8A	119.9
C2—N2—N3—C1	−0.42 (15)	C8—C3—C4—C5	−0.32 (19)
C2—N2—N3—C3	178.65 (11)	N3—C3—C4—C5	179.64 (11)
C2—N1—C1—N3	−0.25 (16)	C3—C4—C5—C6	0.0 (2)
N2—N3—C1—N1	0.44 (16)	C4—C5—C6—N4	−178.34 (13)
C3—N3—C1—N1	−178.55 (12)	C4—C5—C6—C7	0.26 (19)
N3—N2—C2—N1	0.29 (17)	N4—C6—C7—C8	178.50 (13)
C1—N1—C2—N2	−0.04 (18)	C5—C6—C7—C8	−0.11 (19)
C1—N3—C3—C4	−146.03 (13)	C6—C7—C8—C3	−0.3 (2)
N2—N3—C3—C4	35.09 (17)	C4—C3—C8—C7	0.48 (19)
C1—N3—C3—C8	33.93 (19)	N3—C3—C8—C7	−179.49 (11)
N2—N3—C3—C8	−144.95 (12)

Cg2 is the centroid of the C3–C8 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
N4—H2N4···N1i	0.871 (16)	2.208 (16)	3.0709 (18)	171.1 (15)
C1—H1A···N2ii	0.93	2.50	3.4035 (16)	166
N4—H1N4···Cg2iii	0.87 (2)	2.58 (2)	3.3929 (16)	156.0 (17)

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C3–C8 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H2N4⋯N1i	0.871 (16)	2.208 (16)	3.0709 (18)	171.1 (15)
C1—H1A⋯N2ii	0.93	2.50	3.4035 (16)	166
N4—H1N4⋯Cg2iii	0.87 (2)	2.58 (2)	3.3929 (16)	156.0 (17)

Symmetry codes: (i) ; (ii) ; (iii) .