3-(4-Nitro-phen-yl)-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(8)H(6)N(4)O(2)S, the 1,2,4-triazole ring and the nitro group form dihedral angles of 6.26 (13) and 9.5 (3)°, respectively, with the phenyl ring. In the crystal, the mol-ecules are linked via pairs of N-H⋯S hydrogen bonds, generating [010] chains which contain R(2) (2) (8) ring motifs. The crystal structure is further stabilized by π-π stacking [centroid-centroid distance = 3.5491 (14) Å] inter-actions.

Related literature

For general background to and the biological activity of 1,2,4-triazole derivatives, see: Shujuan et al. (2004 ▶); Clemons et al. (2004 ▶); Johnston (2002 ▶); Wei et al. (2007 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶).

Experimental

Crystal data

C8H6N4O2S

M = 222.23

Monoclinic,

a = 7.8221 (1) Å

b = 8.2109 (1) Å

c = 14.6757 (3) Å

β = 101.302 (1)°

V = 924.29 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.33 mm−1

T = 100 K

0.35 × 0.27 × 0.17 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.892, T max = 0.947

8521 measured reflections

1988 independent reflections

1789 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.109

S = 1.17

1988 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.42 e Å−3

Δρmin = −0.29 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 datablock(s) global, I. DOI: 10.1107/S1600536811033952/hb6376sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033952/hb6376Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811033952/hb6376Isup3.cml

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

C8H6N4O2S	F(000) = 456
Mr = 222.23	Dx = 1.597 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6061 reflections
a = 7.8221 (1) Å	θ = 2.7–32.7°
b = 8.2109 (1) Å	µ = 0.33 mm−1
c = 14.6757 (3) Å	T = 100 K
β = 101.302 (1)°	Block, yellow
V = 924.29 (2) Å3	0.35 × 0.27 × 0.17 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	1988 independent reflections
Radiation source: fine-focus sealed tube	1789 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 27.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −9→8
Tmin = 0.892, Tmax = 0.947	k = −10→10
8521 measured reflections	l = −15→18

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) = 0.109	H atoms treated by a mixture of independent and constrained refinement
S = 1.17	w = 1/[σ2(Fo2) + (0.023P)2 + 1.7764P] where P = (Fo2 + 2Fc2)/3
1988 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
S1	0.48563 (8)	0.37379 (7)	0.18859 (4)	0.02226 (18)
O1	0.0046 (3)	0.9832 (3)	0.65011 (15)	0.0430 (6)
O2	0.0293 (3)	0.7834 (3)	0.74650 (13)	0.0364 (5)
N1	0.3673 (3)	0.5040 (3)	0.33704 (14)	0.0184 (4)
N2	0.3841 (3)	0.2469 (3)	0.34126 (15)	0.0227 (5)
N3	0.3212 (3)	0.2888 (3)	0.41922 (14)	0.0227 (5)
N4	0.0471 (3)	0.8436 (3)	0.67295 (14)	0.0265 (5)
C1	0.4131 (3)	0.3742 (3)	0.29010 (16)	0.0192 (5)
C2	0.3128 (3)	0.4479 (3)	0.41483 (16)	0.0187 (5)
C3	0.2506 (3)	0.5522 (3)	0.48290 (16)	0.0186 (5)
C4	0.2100 (3)	0.4814 (3)	0.56284 (16)	0.0206 (5)
H4A	0.2269	0.3680	0.5738	0.025*
C5	0.1450 (3)	0.5774 (3)	0.62606 (16)	0.0218 (5)
H5A	0.1165	0.5310	0.6805	0.026*
C6	0.1226 (3)	0.7419 (3)	0.60807 (16)	0.0223 (5)
C7	0.1638 (3)	0.8162 (3)	0.53043 (17)	0.0235 (5)
H7A	0.1490	0.9301	0.5208	0.028*
C8	0.2272 (3)	0.7193 (3)	0.46708 (16)	0.0210 (5)
H8A	0.2548	0.7668	0.4127	0.025*
H1N1	0.384 (4)	0.601 (4)	0.323 (2)	0.026 (8)*
H1N2	0.400 (4)	0.154 (4)	0.329 (2)	0.033 (9)*

	U11	U22	U33	U12	U13	U23
S1	0.0335 (3)	0.0136 (3)	0.0225 (3)	−0.0009 (2)	0.0124 (2)	−0.0021 (2)
O1	0.0675 (15)	0.0288 (12)	0.0374 (11)	0.0141 (11)	0.0220 (10)	−0.0025 (9)
O2	0.0480 (12)	0.0404 (13)	0.0235 (9)	0.0060 (10)	0.0140 (8)	−0.0005 (9)
N1	0.0223 (10)	0.0137 (11)	0.0204 (10)	0.0009 (8)	0.0070 (8)	−0.0006 (8)
N2	0.0280 (11)	0.0160 (11)	0.0271 (11)	0.0011 (9)	0.0128 (9)	−0.0006 (9)
N3	0.0262 (10)	0.0192 (11)	0.0255 (10)	0.0011 (8)	0.0118 (8)	−0.0001 (9)
N4	0.0292 (11)	0.0280 (13)	0.0229 (10)	0.0014 (9)	0.0063 (8)	−0.0047 (9)
C1	0.0185 (10)	0.0170 (12)	0.0222 (11)	−0.0003 (9)	0.0045 (9)	−0.0029 (10)
C2	0.0149 (10)	0.0207 (13)	0.0207 (11)	0.0002 (9)	0.0040 (8)	0.0016 (10)
C3	0.0146 (10)	0.0217 (13)	0.0198 (11)	0.0000 (9)	0.0040 (8)	−0.0044 (10)
C4	0.0188 (10)	0.0205 (13)	0.0220 (11)	−0.0007 (9)	0.0026 (9)	0.0014 (10)
C5	0.0193 (11)	0.0287 (14)	0.0170 (11)	−0.0006 (10)	0.0030 (9)	0.0014 (10)
C6	0.0197 (11)	0.0272 (14)	0.0202 (11)	0.0015 (10)	0.0046 (9)	−0.0060 (10)
C7	0.0264 (12)	0.0187 (12)	0.0258 (12)	0.0037 (10)	0.0065 (10)	−0.0002 (10)
C8	0.0241 (11)	0.0199 (13)	0.0205 (11)	−0.0005 (9)	0.0079 (9)	−0.0003 (10)

S1—C1	1.695 (2)	C2—C3	1.469 (3)
O1—N4	1.222 (3)	C3—C8	1.398 (3)
O2—N4	1.220 (3)	C3—C4	1.400 (3)
N1—C1	1.355 (3)	C4—C5	1.387 (3)
N1—C2	1.375 (3)	C4—H4A	0.9500
N1—H1N1	0.84 (3)	C5—C6	1.380 (4)
N2—C1	1.332 (3)	C5—H5A	0.9500
N2—N3	1.375 (3)	C6—C7	1.385 (3)
N2—H1N2	0.80 (3)	C7—C8	1.387 (3)
N3—C2	1.309 (3)	C7—H7A	0.9500
N4—C6	1.474 (3)	C8—H8A	0.9500
C1—N1—C2	108.3 (2)	C8—C3—C2	120.6 (2)
C1—N1—H1N1	124 (2)	C4—C3—C2	119.2 (2)
C2—N1—H1N1	127 (2)	C5—C4—C3	119.8 (2)
C1—N2—N3	113.7 (2)	C5—C4—H4A	120.1
C1—N2—H1N2	125 (2)	C3—C4—H4A	120.1
N3—N2—H1N2	122 (2)	C6—C5—C4	118.5 (2)
C2—N3—N2	103.4 (2)	C6—C5—H5A	120.8
O2—N4—O1	123.4 (2)	C4—C5—H5A	120.8
O2—N4—C6	118.1 (2)	C5—C6—C7	123.2 (2)
O1—N4—C6	118.4 (2)	C5—C6—N4	118.8 (2)
N2—C1—N1	103.9 (2)	C7—C6—N4	118.0 (2)
N2—C1—S1	128.14 (19)	C6—C7—C8	118.1 (2)
N1—C1—S1	127.98 (19)	C6—C7—H7A	121.0
N3—C2—N1	110.8 (2)	C8—C7—H7A	121.0
N3—C2—C3	124.6 (2)	C7—C8—C3	120.3 (2)
N1—C2—C3	124.6 (2)	C7—C8—H8A	119.9
C8—C3—C4	120.2 (2)	C3—C8—H8A	119.9
C1—N2—N3—C2	−0.3 (3)	C2—C3—C4—C5	−177.6 (2)
N3—N2—C1—N1	0.1 (3)	C3—C4—C5—C6	−0.2 (3)
N3—N2—C1—S1	−178.54 (17)	C4—C5—C6—C7	−0.7 (4)
C2—N1—C1—N2	0.1 (2)	C4—C5—C6—N4	177.6 (2)
C2—N1—C1—S1	178.73 (18)	O2—N4—C6—C5	9.9 (3)
N2—N3—C2—N1	0.3 (3)	O1—N4—C6—C5	−169.7 (2)
N2—N3—C2—C3	179.3 (2)	O2—N4—C6—C7	−171.7 (2)
C1—N1—C2—N3	−0.2 (3)	O1—N4—C6—C7	8.7 (3)
C1—N1—C2—C3	−179.2 (2)	C5—C6—C7—C8	1.3 (4)
N3—C2—C3—C8	−172.6 (2)	N4—C6—C7—C8	−177.0 (2)
N1—C2—C3—C8	6.3 (3)	C6—C7—C8—C3	−0.9 (4)
N3—C2—C3—C4	5.6 (4)	C4—C3—C8—C7	0.0 (3)
N1—C2—C3—C4	−175.6 (2)	C2—C3—C8—C7	178.2 (2)
C8—C3—C4—C5	0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S1i	0.84 (3)	2.48 (3)	3.295 (3)	164 (3)
N2—H1N2···S1ii	0.80 (3)	2.50 (3)	3.285 (3)	168 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S1i	0.84 (3)	2.48 (3)	3.295 (3)	164 (3)
N2—H1N2⋯S1ii	0.80 (3)	2.50 (3)	3.285 (3)	168 (3)

Symmetry codes: (i) ; (ii) .