3-Benzyl-sulfanyl-1H-1,2,4-triazol-5-amine.

In the title mol-ecule, C(9)H(10)N(4)S, the dihedral angle between the benzene and triazole rings is 81.05 (5)°. In the crystal, N-H⋯N hydrogen bonds link the mol-ecules into infinite zigzag chains along [010].

Related literature

For the biological properties of 1,2,4-triazoles derivatives, see: Paulvannan et al. (2001 ▶); El-Sagheer & Brown (2011 ▶).

Experimental

Crystal data

C9H10N4S

M = 206.27

Monoclinic,

a = 9.870 (2) Å

b = 9.6370 (19) Å

c = 10.398 (2) Å

β = 90.18 (3)°

V = 989.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 293 K

0.38 × 0.26 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.897, T max = 0.970

9367 measured reflections

2267 independent reflections

1372 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.111

S = 1.04

2267 reflections

136 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.25 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002 ▶); 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811052159/cv5211sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052159/cv5211Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052159/cv5211Isup3.cml

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

C9H10N4S	F(000) = 432
Mr = 206.27	Dx = 1.385 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6282 reflections
a = 9.870 (2) Å	θ = 3.5–27.5°
b = 9.6370 (19) Å	µ = 0.29 mm−1
c = 10.398 (2) Å	T = 293 K
β = 90.18 (3)°	Block, colorless
V = 989.0 (3) Å3	0.38 × 0.26 × 0.11 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2267 independent reflections
Radiation source: fine-focus sealed tube	1372 reflections with I > 2σ(I)
graphite	Rint = 0.059
ω scan	θmax = 27.5°, θmin = 3.5°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −12→12
Tmin = 0.897, Tmax = 0.970	k = −12→12
9367 measured reflections	l = −13→13

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0455P)2 + 0.1013P] where P = (Fo2 + 2Fc2)/3
2267 reflections	(Δ/σ)max < 0.001
136 parameters	Δρmax = 0.26 e Å−3
3 restraints	Δρmin = −0.25 e Å−3

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
C1	0.9298 (2)	0.2955 (2)	0.45864 (19)	0.0424 (5)
C2	1.0473 (2)	0.2171 (2)	0.4593 (2)	0.0510 (6)
H2	1.0536	0.1402	0.5131	0.061*
C3	1.1549 (3)	0.2511 (3)	0.3816 (2)	0.0598 (7)
H3	1.2329	0.1969	0.3823	0.072*
C4	1.1468 (3)	0.3657 (3)	0.3029 (2)	0.0606 (7)
H4	1.2198	0.3896	0.2510	0.073*
C5	1.0312 (3)	0.4446 (3)	0.3008 (2)	0.0564 (6)
H5	1.0256	0.5214	0.2469	0.068*
C6	0.9232 (2)	0.4102 (2)	0.3784 (2)	0.0501 (6)
H6	0.8453	0.4644	0.3769	0.060*
C7	0.8148 (2)	0.2577 (3)	0.5473 (2)	0.0541 (6)
H7A	0.7510	0.3341	0.5495	0.065*
H7B	0.8506	0.2456	0.6335	0.065*
C8	0.6212 (2)	0.1615 (2)	0.3776 (2)	0.0442 (5)
C9	0.4869 (2)	0.1511 (2)	0.2191 (2)	0.0462 (6)
N1	0.5965 (2)	0.29303 (18)	0.3524 (2)	0.0541 (5)
N2	0.5088 (2)	0.28358 (17)	0.2498 (2)	0.0539 (5)
H21	0.473 (3)	0.3613 (18)	0.216 (2)	0.081*
N3	0.55663 (18)	0.06938 (16)	0.29881 (19)	0.0460 (5)
N4	0.4055 (2)	0.1079 (2)	0.1236 (2)	0.0665 (6)
H41	0.404 (3)	0.0173 (12)	0.107 (3)	0.100*
H42	0.368 (3)	0.167 (3)	0.068 (2)	0.100*
S1	0.72492 (7)	0.10082 (6)	0.50093 (7)	0.0582 (2)

	U11	U22	U33	U12	U13	U23
C1	0.0478 (13)	0.0408 (11)	0.0385 (11)	−0.0047 (9)	−0.0002 (10)	−0.0064 (10)
C2	0.0548 (15)	0.0433 (13)	0.0548 (14)	0.0000 (10)	−0.0025 (12)	0.0058 (11)
C3	0.0481 (15)	0.0580 (15)	0.0735 (16)	0.0027 (12)	0.0074 (13)	0.0032 (13)
C4	0.0516 (16)	0.0676 (17)	0.0625 (15)	−0.0123 (13)	0.0078 (12)	0.0057 (14)
C5	0.0657 (18)	0.0511 (14)	0.0522 (14)	−0.0083 (12)	−0.0014 (13)	0.0119 (12)
C6	0.0508 (14)	0.0453 (12)	0.0543 (13)	0.0016 (10)	−0.0055 (11)	0.0007 (11)
C7	0.0587 (16)	0.0511 (13)	0.0525 (13)	−0.0024 (11)	0.0059 (12)	−0.0027 (11)
C8	0.0382 (12)	0.0273 (10)	0.0672 (14)	0.0003 (9)	0.0137 (11)	0.0022 (10)
C9	0.0393 (12)	0.0266 (10)	0.0728 (15)	−0.0016 (9)	0.0111 (11)	0.0016 (11)
N1	0.0525 (13)	0.0264 (9)	0.0834 (14)	0.0016 (8)	−0.0020 (11)	−0.0027 (9)
N2	0.0495 (12)	0.0245 (9)	0.0876 (15)	0.0002 (8)	−0.0015 (11)	0.0035 (9)
N3	0.0400 (10)	0.0226 (8)	0.0753 (13)	−0.0012 (7)	0.0092 (9)	0.0002 (9)
N4	0.0709 (16)	0.0374 (11)	0.0912 (17)	−0.0030 (10)	−0.0166 (13)	0.0004 (12)
S1	0.0576 (4)	0.0398 (3)	0.0774 (5)	−0.0023 (3)	0.0053 (3)	0.0130 (3)

C1—C2	1.384 (3)	C7—H7A	0.9700
C1—C6	1.386 (3)	C7—H7B	0.9700
C1—C7	1.509 (3)	C8—N1	1.317 (3)
C2—C3	1.377 (3)	C8—N3	1.365 (3)
C2—H2	0.9300	C8—S1	1.740 (2)
C3—C4	1.376 (3)	C9—N3	1.333 (3)
C3—H3	0.9300	C9—N2	1.334 (3)
C4—C5	1.371 (4)	C9—N4	1.342 (3)
C4—H4	0.9300	N1—N2	1.375 (3)
C5—C6	1.380 (3)	N2—H21	0.900 (10)
C5—H5	0.9300	N4—H42	0.892 (10)
C6—H6	0.9300	N4—H41	0.889 (10)
C7—S1	1.817 (2)	N4—H42	0.892 (10)
C2—C1—C6	118.5 (2)	C1—C7—H7B	108.8
C2—C1—C7	119.8 (2)	S1—C7—H7B	108.8
C6—C1—C7	121.7 (2)	H7A—C7—H7B	107.6
C3—C2—C1	121.0 (2)	N1—C8—N3	114.9 (2)
C3—C2—H2	119.5	N1—C8—S1	125.35 (18)
C1—C2—H2	119.5	N3—C8—S1	119.75 (15)
C4—C3—C2	119.8 (2)	N3—C9—N2	109.5 (2)
C4—C3—H3	120.1	N3—C9—N4	125.7 (2)
C2—C3—H3	120.1	N2—C9—N4	124.8 (2)
C5—C4—C3	120.0 (2)	C8—N1—N2	101.91 (18)
C5—C4—H4	120.0	C9—N2—N1	110.48 (19)
C3—C4—H4	120.0	C9—N2—H21	129.8 (18)
C4—C5—C6	120.1 (2)	N1—N2—H21	119.7 (17)
C4—C5—H5	119.9	C9—N3—C8	103.18 (17)
C6—C5—H5	119.9	H42—N4—C9	122 (2)
C5—C6—C1	120.6 (2)	H42—N4—H41	120 (3)
C5—C6—H6	119.7	C9—N4—H41	117 (2)
C1—C6—H6	119.7	H42—N4—H42	0(2)
C1—C7—S1	113.99 (16)	C9—N4—H42	122 (2)
C1—C7—H7A	108.8	H41—N4—H42	120 (3)
S1—C7—H7A	108.8	C8—S1—C7	101.62 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H41···N1i	0.89 (1)	2.20 (2)	3.044 (3)	158 (3)
N2—H21···N3ii	0.90 (1)	2.03 (2)	2.873 (2)	155 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H41⋯N1i	0.89 (1)	2.20 (2)	3.044 (3)	158 (3)
N2—H21⋯N3ii	0.90 (1)	2.03 (2)	2.873 (2)	155 (2)

Symmetry codes: (i) ; (ii) .