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

In the title compound, C(8)H(8)N(4)S, the planar triazole ring forms a dihedral angle of 13.7 (2)° with the phenyl ring. The crystal structure is stabilized by inter-molecular N-H⋯S hydrogen-bond inter-actions, linking the mol-ecules into chains along the a axis.

Related literature

For the applications of triazole compounds, see: Xu et al. (2002 ▶); Jantova et al. (1998 ▶); Holla et al. (1996 ▶); Pevzner (1997 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H8N4S

M = 192.25

Monoclinic,

a = 5.5574 (4) Å

b = 25.2384 (3) Å

c = 6.6327 (4) Å

β = 104.511 (1)°

V = 900.63 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 293 (2) K

0.2 × 0.2 × 0.2 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.736, T max = 0.939

8689 measured reflections

2134 independent reflections

1464 reflections with I > 2σ(I)

R int = 0.062

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.223

S = 1.12

2134 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.44 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536808014967/rz2214sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808014967/rz2214Isup2.hkl

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

C8H8N4S	F000 = 400
Mr = 192.25	Dx = 1.418 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1686 reflections
a = 5.5574 (4) Å	θ = 3.2–27.5º
b = 25.2384 (3) Å	µ = 0.31 mm−1
c = 6.6327 (4) Å	T = 293 (2) K
β = 104.5110 (10)º	Block, colourless
V = 900.63 (9) Å3	0.2 × 0.2 × 0.2 mm
Z = 4

Rigaku Mercury2 diffractometer	2134 independent reflections
Radiation source: fine-focus sealed tube	1464 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.062
Detector resolution: 13.6612 pixels mm-1	θmax = 27.9º
T = 293(2) K	θmin = 3.2º
CCD_Profile_fitting scans	h = −7→7
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)	k = −33→32
Tmin = 0.736, Tmax = 0.939	l = −8→8
8689 measured reflections

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)] = 0.067	H-atom parameters constrained
wR(F2) = 0.223	w = 1/[σ2(Fo2) + (0.1186P)2] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
2134 reflections	Δρmax = 0.46 e Å−3
118 parameters	Δρmin = −0.44 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	0.12788 (16)	0.01977 (3)	0.82762 (13)	0.0565 (3)
N3	0.4947 (5)	0.08640 (10)	0.7790 (4)	0.0427 (6)
N2	0.3057 (5)	0.05034 (10)	0.4961 (4)	0.0461 (6)
H2A	0.2049	0.0311	0.4058	0.055*
N1	0.4798 (5)	0.08322 (10)	0.4454 (4)	0.0478 (7)
C1	0.7971 (6)	0.14417 (11)	0.6429 (5)	0.0413 (7)
C7	0.5948 (5)	0.10520 (11)	0.6248 (4)	0.0405 (7)
C6	0.9052 (6)	0.14961 (12)	0.4763 (5)	0.0465 (7)
H6A	0.8489	0.1288	0.3581	0.056*
C8	0.3071 (6)	0.05098 (11)	0.6963 (5)	0.0431 (7)
N4	0.5695 (6)	0.09940 (12)	0.9922 (4)	0.0611 (8)
H4B	0.6203	0.0702	1.0659	0.092*
H4D	0.4409	0.1133	1.0312	0.092*
C5	1.0959 (6)	0.18563 (13)	0.4843 (6)	0.0531 (8)
H5A	1.1668	0.1889	0.3719	0.064*
C4	1.1802 (7)	0.21651 (13)	0.6595 (6)	0.0566 (9)
H4C	1.3088	0.2405	0.6658	0.068*
C2	0.8828 (8)	0.17585 (14)	0.8169 (6)	0.0625 (10)
H2B	0.8124	0.1732	0.9298	0.075*
C3	1.0756 (8)	0.21171 (16)	0.8214 (6)	0.0703 (11)
H3A	1.1330	0.2328	0.9387	0.084*

	U11	U22	U33	U12	U13	U23
S1	0.0563 (6)	0.0662 (6)	0.0481 (5)	−0.0193 (4)	0.0153 (4)	0.0046 (4)
N3	0.0450 (14)	0.0473 (13)	0.0346 (12)	−0.0077 (11)	0.0079 (10)	0.0004 (10)
N2	0.0478 (15)	0.0508 (14)	0.0406 (14)	−0.0148 (11)	0.0126 (11)	−0.0067 (11)
N1	0.0475 (15)	0.0538 (15)	0.0440 (14)	−0.0102 (12)	0.0153 (12)	−0.0050 (11)
C1	0.0407 (15)	0.0386 (14)	0.0446 (16)	−0.0013 (11)	0.0105 (12)	0.0017 (11)
C7	0.0432 (15)	0.0408 (14)	0.0389 (15)	−0.0019 (12)	0.0128 (12)	−0.0005 (11)
C6	0.0465 (17)	0.0545 (17)	0.0396 (15)	−0.0057 (13)	0.0130 (14)	0.0005 (12)
C8	0.0436 (17)	0.0434 (15)	0.0414 (16)	−0.0051 (12)	0.0086 (13)	0.0015 (12)
N4	0.079 (2)	0.0703 (18)	0.0332 (14)	−0.0228 (16)	0.0128 (13)	−0.0022 (13)
C5	0.0485 (18)	0.0603 (19)	0.0535 (19)	−0.0055 (15)	0.0185 (15)	0.0091 (15)
C4	0.0497 (18)	0.0535 (19)	0.068 (2)	−0.0110 (15)	0.0168 (17)	0.0027 (16)
C2	0.069 (2)	0.071 (2)	0.055 (2)	−0.0244 (18)	0.0276 (17)	−0.0158 (17)
C3	0.077 (3)	0.072 (2)	0.067 (2)	−0.031 (2)	0.027 (2)	−0.0212 (19)

S1—C8	1.675 (3)	C6—C5	1.387 (4)
N3—C7	1.366 (4)	C6—H6A	0.9300
N3—C8	1.378 (4)	N4—H4B	0.8900
N3—N4	1.409 (3)	N4—H4D	0.8900
N2—C8	1.326 (4)	C5—C4	1.380 (5)
N2—N1	1.379 (3)	C5—H5A	0.9300
N2—H2A	0.8600	C4—C3	1.349 (5)
N1—C7	1.323 (4)	C4—H4C	0.9300
C1—C2	1.387 (4)	C2—C3	1.397 (5)
C1—C6	1.390 (4)	C2—H2B	0.9300
C1—C7	1.476 (4)	C3—H3A	0.9300
C7—N3—C8	109.7 (2)	N2—C8—S1	131.3 (2)
C7—N3—N4	126.7 (2)	N3—C8—S1	125.9 (2)
C8—N3—N4	123.6 (3)	N3—N4—H4B	109.3
C8—N2—N1	114.1 (2)	N3—N4—H4D	109.1
C8—N2—H2A	123.0	H4B—N4—H4D	109.5
N1—N2—H2A	123.0	C4—C5—C6	119.8 (3)
C7—N1—N2	104.1 (2)	C4—C5—H5A	120.1
C2—C1—C6	118.5 (3)	C6—C5—H5A	120.1
C2—C1—C7	123.2 (3)	C3—C4—C5	119.8 (3)
C6—C1—C7	118.3 (3)	C3—C4—H4C	120.1
N1—C7—N3	109.4 (2)	C5—C4—H4C	120.1
N1—C7—C1	122.6 (3)	C1—C2—C3	119.6 (3)
N3—C7—C1	128.0 (3)	C1—C2—H2B	120.2
C5—C6—C1	120.8 (3)	C3—C2—H2B	120.2
C5—C6—H6A	119.6	C4—C3—C2	121.5 (3)
C1—C6—H6A	119.6	C4—C3—H3A	119.3
N2—C8—N3	102.8 (2)	C2—C3—H3A	119.3

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···S1i	0.86	2.46	3.310 (3)	172
N4—H4B···S1ii	0.89	2.67	3.506 (3)	157

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯S1i	0.86	2.46	3.310 (3)	172
N4—H4B⋯S1ii	0.89	2.67	3.506 (3)	157

Symmetry codes: (i) ; (ii) .