4-Amino-3-(4-pyrid-yl)-1,2,4-triazole-5(4H)-thione.

In the title mol-ecule, C(7)H(7)N(5)S, the pyridyl and triazole rings form a dihedral angle of 20.07 (6)°. Inter-molecular N-H⋯N hydrogen bonds link the mol-ecules into chains extended in the direction [10]. Further stability is provided by π⋯π stacking inter-actions, indicated by short distances between the centroids of triazole rings [3.480 (5) Å] and pyridyl rings [3.574 (5) Å] of neighbouring mol-ecules.

Related literature

For the biological activities of related compounds, see: Eweiss et al. (1986 ▶); Awad et al. (1991 ▶). For a similar structure, see Kajdan et al. (2000 ▶).

Experimental

Crystal data

C7H7N5S

M = 193.24

Monoclinic,

a = 7.722 (6) Å

b = 14.215 (11) Å

c = 15.068 (12) Å

β = 93.432 (15)°

V = 1651 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.35 mm−1

T = 273 (2) K

0.15 × 0.10 × 0.08 mm

Data collection

Bruker APEX area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.950, T max = 0.973

4402 measured reflections

1626 independent reflections

1116 reflections with I > 2σ(I)

R int = 0.060

Refinement

R[F 2 > 2σ(F 2)] = 0.065

wR(F 2) = 0.169

S = 1.01

1626 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.28 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and ViewerPro (Accelrys, 2001 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807064331/cv2366sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807064331/cv2366Isup2.hkl

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

C7H7N5S	F000 = 800
Mr = 193.24	Dx = 1.555 Mg m−3
Monoclinic, C2/c	Mo Kα radiation λ = 0.71073 Å
a = 7.722 (6) Å	Cell parameters from 1061 reflections
b = 14.215 (11) Å	θ = 2.7–23.8º
c = 15.068 (12) Å	µ = 0.35 mm−1
β = 93.432 (15)º	T = 273 (2) K
V = 1651 (2) Å3	Clubbed, colourless
Z = 8	0.15 × 0.10 × 0.08 mm

Bruker APEX area-detector diffractometer	1626 independent reflections
Radiation source: fine-focus sealed tube	1116 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.060
T = 273(2) K	θmax = 26.0º
φ and ω scan	θmin = 2.7º
Absorption correction: multi-scan(SADABS; Bruker, 2001)	h = −9→9
Tmin = 0.950, Tmax = 0.973	k = −16→17
4402 measured reflections	l = −8→18

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)] = 0.065	H-atom parameters constrained
wR(F2) = 0.169	w = 1/[σ2(Fo2) + (0.0857P)2 + 0.3739P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max = 0.048
1626 reflections	Δρmax = 0.29 e Å−3
118 parameters	Δρmin = −0.28 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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
S1	0.11589 (13)	0.51429 (7)	0.38748 (7)	0.0572 (4)
N5	0.2341 (3)	0.73058 (19)	0.24951 (19)	0.0425 (8)
C6	0.2889 (4)	0.6629 (2)	0.2010 (2)	0.0362 (8)
N3	0.2571 (3)	0.57925 (19)	0.2400 (2)	0.0414 (7)
C3	0.3732 (4)	0.6799 (2)	0.1189 (2)	0.0366 (8)
N1	0.5323 (3)	0.7249 (2)	−0.0353 (2)	0.0468 (8)
N4	0.1676 (3)	0.68743 (19)	0.31970 (19)	0.0401 (7)
H4B	0.1229	0.7172	0.3624	0.048*
C7	0.1781 (4)	0.5945 (2)	0.3160 (2)	0.0409 (9)
C1	0.5178 (5)	0.7863 (3)	0.0293 (3)	0.0551 (11)
H1A	0.5630	0.8462	0.0219	0.066*
N2	0.2980 (4)	0.49002 (19)	0.2082 (2)	0.0579 (10)
H2B	0.2642	0.4458	0.2463	0.087*
H2C	0.2407	0.4820	0.1550	0.087*
C4	0.3874 (5)	0.6154 (3)	0.0534 (3)	0.0564 (11)
H4A	0.3438	0.5550	0.0596	0.068*
C5	0.4670 (5)	0.6408 (3)	−0.0219 (3)	0.0591 (11)
H5A	0.4753	0.5959	−0.0663	0.071*
C2	0.4414 (4)	0.7675 (3)	0.1055 (2)	0.0493 (10)
H2A	0.4350	0.8138	0.1488	0.059*

	U11	U22	U33	U12	U13	U23
S1	0.0686 (7)	0.0505 (6)	0.0540 (7)	0.0022 (5)	0.0170 (6)	0.0140 (5)
N5	0.0460 (16)	0.0430 (16)	0.0394 (18)	−0.0043 (12)	0.0104 (15)	−0.0002 (13)
C6	0.0297 (16)	0.0445 (19)	0.034 (2)	−0.0018 (13)	0.0000 (15)	0.0030 (16)
N3	0.0415 (15)	0.0405 (16)	0.0433 (18)	0.0031 (11)	0.0118 (14)	0.0008 (13)
C3	0.0259 (15)	0.0485 (19)	0.035 (2)	0.0043 (13)	0.0030 (15)	0.0050 (16)
N1	0.0402 (15)	0.062 (2)	0.0383 (19)	0.0031 (14)	0.0070 (14)	0.0012 (16)
N4	0.0420 (15)	0.0470 (17)	0.0324 (17)	−0.0008 (12)	0.0111 (14)	0.0011 (13)
C7	0.0330 (16)	0.043 (2)	0.047 (2)	0.0027 (14)	0.0053 (17)	0.0025 (16)
C1	0.064 (2)	0.048 (2)	0.055 (3)	−0.0077 (17)	0.018 (2)	0.002 (2)
N2	0.076 (2)	0.0413 (17)	0.060 (2)	0.0057 (15)	0.0273 (19)	−0.0025 (16)
C4	0.070 (2)	0.047 (2)	0.053 (3)	−0.0123 (18)	0.018 (2)	−0.005 (2)
C5	0.077 (3)	0.059 (3)	0.043 (2)	−0.002 (2)	0.021 (2)	−0.0063 (19)
C2	0.061 (2)	0.046 (2)	0.042 (2)	0.0017 (17)	0.0151 (19)	−0.0012 (17)

S1—C7	1.659 (4)	N4—C7	1.325 (4)
N5—C6	1.295 (4)	N4—H4B	0.8600
N5—N4	1.350 (4)	C1—C2	1.349 (5)
C6—N3	1.356 (4)	C1—H1A	0.9300
C6—C3	1.452 (4)	N2—H2B	0.9000
N3—C7	1.347 (4)	N2—H2C	0.8999
N3—N2	1.399 (4)	C4—C5	1.371 (5)
C3—C4	1.355 (5)	C4—H4A	0.9300
C3—C2	1.372 (5)	C5—H5A	0.9300
N1—C5	1.319 (5)	C2—H2A	0.9300
N1—C1	1.317 (5)
C6—N5—N4	104.9 (3)	N3—C7—S1	127.2 (3)
N5—C6—N3	109.5 (3)	N1—C1—C2	124.0 (3)
N5—C6—C3	122.4 (3)	N1—C1—H1A	118.0
N3—C6—C3	128.1 (3)	C2—C1—H1A	118.0
C7—N3—C6	109.3 (3)	N3—N2—H2B	109.6
C7—N3—N2	124.1 (3)	N3—N2—H2C	108.1
C6—N3—N2	126.6 (3)	H2B—N2—H2C	109.5
C4—C3—C2	117.3 (3)	C3—C4—C5	119.0 (4)
C4—C3—C6	124.6 (3)	C3—C4—H4A	120.5
C2—C3—C6	118.1 (3)	C5—C4—H4A	120.5
C5—N1—C1	115.9 (3)	N1—C5—C4	124.1 (4)
C7—N4—N5	113.1 (3)	N1—C5—H5A	118.0
C7—N4—H4B	123.4	C4—C5—H5A	118.0
N5—N4—H4B	123.4	C1—C2—C3	119.7 (3)
N4—C7—N3	103.2 (3)	C1—C2—H2A	120.1
N4—C7—S1	129.6 (3)	C3—C2—H2A	120.1

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···N1i	0.86	1.91	2.772 (4)	175

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯N1i	0.86	1.91	2.772 (4)	175

Symmetry code: (i) .