4-[(E)-(3-Methyl-5-thioxo-4,5-dihydro-1H-1,2,4-triazol-4-yl)imino-meth-yl]benzonitrile.

In the title compound, C(11)H(9)N(5)S, the dihedral angle between the mean planes of the thione-substituted triazole ring and benzonitrile ring is 4.28 (3)°. Inter-molecular N-H⋯S hydrogen bonds link the mol-ecules together into characteristic dimers.

Related literature

For the application of benzotriazole compounds in industry, see: Sharma & Bahel (1982 ▶); Grasso (1988 ▶); Eweiss et al. (1986 ▶); Awad et al. (1991 ▶); Pillard et al. (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C11H9N5S

M = 243.29

Triclinic,

a = 6.975 (2) Å

b = 7.682 (2) Å

c = 11.412 (2) Å

α = 90.262 (7)°

β = 94.328 (14)°

γ = 104.713 (17)°

V = 589.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 (2) K

0.70 × 0.50 × 0.50 mm

Data collection

Rigaku Mercury2 diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.854, T max = 0.901

5954 measured reflections

2659 independent reflections

2178 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.115

S = 1.05

2659 reflections

155 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.20 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/S1600536808017613/rn2041sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808017613/rn2041Isup2.hkl

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

C11H9N5S	Z = 2
Mr = 243.29	F000 = 252
Triclinic, P1	Dx = 1.371 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 6.975 (2) Å	Cell parameters from 1492 reflections
b = 7.682 (2) Å	θ = 3.0–27.4º
c = 11.412 (2) Å	µ = 0.26 mm−1
α = 90.262 (7)º	T = 293 (2) K
β = 94.328 (14)º	Block, colorless
γ = 104.713 (17)º	0.70 × 0.50 × 0.50 mm
V = 589.5 (3) Å3

Rigaku Mercury2 diffractometer	2659 independent reflections
Radiation source: fine-focus sealed tube	2178 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5º
T = 293(2) K	θmin = 3.2º
CCD_Profile_fitting scans	h = −9→9
Absorption correction: Multi-scan(CrystalClear; Rigaku, 2005)	k = −9→9
Tmin = 0.854, Tmax = 0.901	l = −14→14
5954 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)] = 0.043	H-atom parameters constrained
wR(F2) = 0.115	w = 1/[σ2(Fo2) + (0.0532P)2 + 0.1343P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
2659 reflections	Δρmax = 0.18 e Å−3
155 parameters	Δρmin = −0.20 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
C1	0.2635 (2)	1.3033 (2)	0.27180 (13)	0.0379 (3)
C2	0.1665 (3)	1.0264 (2)	0.18636 (14)	0.0439 (4)
C3	0.1029 (4)	0.8280 (3)	0.17603 (17)	0.0617 (5)
H3A	0.0629	0.7922	0.0953	0.093*
H3B	−0.0070	0.7840	0.2230	0.093*
H3C	0.2115	0.7789	0.2030	0.093*
C4	0.2745 (2)	1.1001 (2)	0.49268 (13)	0.0400 (4)
H4	0.3196	1.2248	0.4992	0.048*
C5	0.2738 (2)	0.9871 (2)	0.59672 (13)	0.0371 (3)
C6	0.3299 (3)	1.0685 (2)	0.70682 (14)	0.0487 (4)
H6	0.3678	1.1934	0.7142	0.058*
C7	0.3300 (3)	0.9654 (3)	0.80588 (15)	0.0539 (5)
H7	0.3652	1.0206	0.8798	0.065*
C8	0.2773 (3)	0.7799 (2)	0.79417 (15)	0.0476 (4)
C9	0.2227 (3)	0.6970 (2)	0.68453 (16)	0.0514 (4)
H9	0.1879	0.5721	0.6772	0.062*
C10	0.2200 (3)	0.8001 (2)	0.58632 (15)	0.0461 (4)
H10	0.1821	0.7445	0.5127	0.055*
C11	0.2800 (3)	0.6704 (3)	0.89609 (17)	0.0601 (5)
N1	0.21505 (19)	1.11995 (17)	0.29285 (10)	0.0362 (3)
N2	0.1847 (2)	1.1369 (2)	0.10000 (12)	0.0524 (4)
N3	0.2429 (2)	1.3038 (2)	0.15394 (12)	0.0485 (4)
H3D	0.2647	1.4017	0.1151	0.058*
N4	0.2117 (2)	1.02188 (17)	0.39419 (11)	0.0385 (3)
N5	0.2817 (3)	0.5822 (3)	0.97577 (16)	0.0811 (6)
S1	0.32744 (8)	1.48037 (6)	0.36283 (4)	0.05691 (18)

	U11	U22	U33	U12	U13	U23
C1	0.0412 (8)	0.0381 (8)	0.0336 (8)	0.0090 (6)	0.0012 (6)	0.0115 (6)
C2	0.0541 (10)	0.0461 (9)	0.0328 (8)	0.0162 (7)	−0.0013 (7)	0.0027 (6)
C3	0.0905 (15)	0.0456 (10)	0.0494 (11)	0.0217 (10)	−0.0072 (10)	−0.0044 (8)
C4	0.0457 (9)	0.0390 (8)	0.0350 (8)	0.0100 (7)	0.0031 (6)	0.0111 (6)
C5	0.0366 (8)	0.0433 (8)	0.0325 (7)	0.0115 (6)	0.0048 (6)	0.0131 (6)
C6	0.0612 (11)	0.0433 (9)	0.0377 (8)	0.0070 (8)	0.0003 (7)	0.0109 (7)
C7	0.0647 (11)	0.0623 (11)	0.0325 (8)	0.0130 (9)	0.0007 (7)	0.0134 (8)
C8	0.0463 (9)	0.0592 (11)	0.0412 (9)	0.0186 (8)	0.0096 (7)	0.0259 (8)
C9	0.0628 (11)	0.0426 (9)	0.0525 (10)	0.0180 (8)	0.0112 (8)	0.0191 (8)
C10	0.0576 (10)	0.0443 (9)	0.0382 (9)	0.0160 (8)	0.0048 (7)	0.0102 (7)
C11	0.0646 (12)	0.0709 (13)	0.0517 (11)	0.0264 (10)	0.0144 (9)	0.0305 (10)
N1	0.0438 (7)	0.0370 (7)	0.0279 (6)	0.0105 (5)	0.0016 (5)	0.0089 (5)
N2	0.0719 (10)	0.0542 (9)	0.0308 (7)	0.0172 (8)	−0.0013 (6)	0.0065 (6)
N3	0.0652 (9)	0.0451 (8)	0.0328 (7)	0.0103 (7)	0.0016 (6)	0.0154 (6)
N4	0.0465 (7)	0.0389 (7)	0.0312 (6)	0.0125 (6)	0.0041 (5)	0.0136 (5)
N5	0.1056 (16)	0.0881 (14)	0.0603 (11)	0.0394 (12)	0.0213 (10)	0.0456 (10)
S1	0.0794 (4)	0.0363 (2)	0.0488 (3)	0.0070 (2)	−0.0080 (2)	0.00552 (19)

C1—N3	1.3420 (19)	C6—C7	1.383 (2)
C1—N1	1.3887 (19)	C6—H6	0.9300
C1—S1	1.6546 (17)	C7—C8	1.382 (3)
C2—N2	1.296 (2)	C7—H7	0.9300
C2—N1	1.384 (2)	C8—C9	1.383 (3)
C2—C3	1.477 (2)	C8—C11	1.440 (2)
C3—H3A	0.9600	C9—C10	1.377 (2)
C3—H3B	0.9600	C9—H9	0.9300
C3—H3C	0.9600	C10—H10	0.9300
C4—N4	1.266 (2)	C11—N5	1.137 (2)
C4—C5	1.4735 (19)	N1—N4	1.3815 (16)
C4—H4	0.9300	N2—N3	1.371 (2)
C5—C6	1.384 (2)	N3—H3D	0.8600
C5—C10	1.391 (2)
N3—C1—N1	101.52 (13)	C8—C7—C6	119.51 (17)
N3—C1—S1	127.16 (12)	C8—C7—H7	120.2
N1—C1—S1	131.32 (11)	C6—C7—H7	120.2
N2—C2—N1	110.55 (15)	C7—C8—C9	120.50 (15)
N2—C2—C3	126.08 (16)	C7—C8—C11	120.31 (18)
N1—C2—C3	123.37 (15)	C9—C8—C11	119.20 (18)
C2—C3—H3A	109.5	C10—C9—C8	119.79 (17)
C2—C3—H3B	109.5	C10—C9—H9	120.1
H3A—C3—H3B	109.5	C8—C9—H9	120.1
C2—C3—H3C	109.5	C9—C10—C5	120.33 (16)
H3A—C3—H3C	109.5	C9—C10—H10	119.8
H3B—C3—H3C	109.5	C5—C10—H10	119.8
N4—C4—C5	117.83 (15)	N5—C11—C8	179.2 (2)
N4—C4—H4	121.1	N4—N1—C2	118.04 (13)
C5—C4—H4	121.1	N4—N1—C1	133.14 (13)
C6—C5—C10	119.33 (14)	C2—N1—C1	108.80 (13)
C6—C5—C4	119.41 (15)	C2—N2—N3	104.07 (13)
C10—C5—C4	121.26 (14)	C1—N3—N2	115.04 (13)
C7—C6—C5	120.52 (17)	C1—N3—H3D	122.5
C7—C6—H6	119.7	N2—N3—H3D	122.5
C5—C6—H6	119.7	C4—N4—N1	120.55 (13)
N4—C4—C5—C6	−176.05 (15)	C3—C2—N1—N4	2.8 (2)
N4—C4—C5—C10	4.7 (2)	N2—C2—N1—C1	1.31 (19)
C10—C5—C6—C7	−0.9 (3)	C3—C2—N1—C1	−178.55 (17)
C4—C5—C6—C7	179.80 (16)	N3—C1—N1—N4	177.34 (15)
C5—C6—C7—C8	1.3 (3)	S1—C1—N1—N4	−3.4 (3)
C6—C7—C8—C9	−0.7 (3)	N3—C1—N1—C2	−0.99 (17)
C6—C7—C8—C11	178.86 (17)	S1—C1—N1—C2	178.25 (13)
C7—C8—C9—C10	−0.3 (3)	N1—C2—N2—N3	−0.99 (19)
C11—C8—C9—C10	−179.81 (17)	C3—C2—N2—N3	178.87 (18)
C8—C9—C10—C5	0.6 (3)	N1—C1—N3—N2	0.42 (19)
C6—C5—C10—C9	−0.1 (3)	S1—C1—N3—N2	−178.87 (13)
C4—C5—C10—C9	179.22 (16)	C2—N2—N3—C1	0.3 (2)
C7—C8—C11—N5	−176 (100)	C5—C4—N4—N1	−177.73 (12)
C9—C8—C11—N5	4(17)	C2—N1—N4—C4	172.61 (15)
N2—C2—N1—N4	−177.30 (14)	C1—N1—N4—C4	−5.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3D···N5i	0.86	2.11	2.934 (2)	162

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3D⋯N5i	0.86	2.11	2.934 (2)	162

Symmetry code: (i) .