3-Ethyl-4-[(E)-(4-fluoro-benzyl-idene)amino]-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(11)H(11)FN(4)S, the dihedral angle between the 1,2,4-triazole ring and the benzene ring is 25.04 (12)° and an intra-moleuclar C-H⋯S inter-action leads to an S(6) ring. In the crystal, inversion dimers linked by pairs of N-H⋯S hydrogen bonds generate R(2) (2)(8) loops.

Related literature

For a related structure and background references, see: Devarajegowda et al. (2010 ▶).

Experimental

Crystal data

C11H11FN4S

M = 250.30

Monoclinic,

a = 7.7967 (17) Å

b = 8.4205 (19) Å

c = 19.138 (4) Å

β = 99.780 (4)°

V = 1238.2 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.20 × 0.20 × 0.15 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: ψ scan (SADABS; Sheldrick, 2007 ▶) T min = 0.770, T max = 1.000

11403 measured reflections

2182 independent reflections

1586 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.115

S = 1.02

2182 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812015346/hb6709sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015346/hb6709Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015346/hb6709Isup3.cml

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

C11H11FN4S	F(000) = 520
Mr = 250.30	Dx = 1.343 Mg m−3
Monoclinic, P21/c	Melting point: 414 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.7967 (17) Å	Cell parameters from 2182 reflections
b = 8.4205 (19) Å	θ = 2.2–25.0°
c = 19.138 (4) Å	µ = 0.26 mm−1
β = 99.780 (4)°	T = 293 K
V = 1238.2 (5) Å3	Block, colourless
Z = 4	0.20 × 0.20 × 0.15 mm

Bruker SMART CCD diffractometer	2182 independent reflections
Radiation source: fine-focus sealed tube	1586 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
ω and φ scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: ψ scan (SADABS; Sheldrick, 2007)	h = −9→9
Tmin = 0.770, Tmax = 1.000	k = −10→10
11403 measured reflections	l = −22→22

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0551P)2 + 0.1712P] where P = (Fo2 + 2Fc2)/3
2182 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.22343 (8)	0.61721 (9)	0.07429 (3)	0.0711 (3)
F2	1.1525 (2)	1.1308 (2)	0.18960 (8)	0.0886 (5)
N3	0.2231 (2)	0.5813 (2)	−0.12894 (9)	0.0579 (5)
N4	0.1651 (2)	0.5520 (2)	−0.06628 (9)	0.0542 (5)
H4	0.0729	0.4974	−0.0641	0.065*
N5	0.3973 (2)	0.6845 (2)	−0.03736 (9)	0.0492 (5)
N6	0.5370 (2)	0.7802 (2)	−0.00763 (10)	0.0536 (5)
C7	0.4043 (4)	0.7150 (5)	−0.23453 (15)	0.1142 (13)
H7A	0.4826	0.7624	−0.2622	0.171*
H7B	0.2932	0.7669	−0.2449	0.171*
H7C	0.3906	0.6043	−0.2460	0.171*
C8	0.4763 (3)	0.7329 (4)	−0.15769 (12)	0.0706 (8)
H8A	0.5896	0.6822	−0.1480	0.085*
H8B	0.4929	0.8450	−0.1469	0.085*
C9	0.3637 (3)	0.6635 (3)	−0.11018 (12)	0.0529 (6)
C10	0.2640 (3)	0.6153 (3)	−0.00883 (11)	0.0512 (6)
C11	0.5946 (3)	0.7675 (3)	0.05793 (13)	0.0555 (6)
H11	0.5433	0.6957	0.0850	0.067*
C12	0.7417 (3)	0.8648 (3)	0.09174 (11)	0.0499 (6)
C13	0.8090 (3)	0.8408 (3)	0.16278 (12)	0.0648 (7)
H13	0.7607	0.7634	0.1881	0.078*
C14	0.9473 (3)	0.9307 (3)	0.19634 (12)	0.0689 (7)
H14	0.9920	0.9155	0.2441	0.083*
C15	1.0162 (3)	1.0415 (3)	0.15780 (13)	0.0594 (6)
C16	0.9559 (3)	1.0674 (3)	0.08733 (12)	0.0569 (6)
H16	1.0078	1.1429	0.0623	0.068*
C17	0.8163 (3)	0.9789 (3)	0.05422 (12)	0.0521 (6)
H17	0.7723	0.9960	0.0065	0.063*

	U11	U22	U33	U12	U13	U23
S1	0.0555 (4)	0.1101 (6)	0.0457 (4)	−0.0195 (4)	0.0028 (3)	−0.0027 (3)
F2	0.0719 (10)	0.1093 (13)	0.0787 (11)	−0.0335 (9)	−0.0044 (8)	−0.0223 (9)
N3	0.0501 (11)	0.0773 (14)	0.0440 (11)	−0.0060 (10)	0.0019 (9)	−0.0030 (10)
N4	0.0456 (10)	0.0688 (13)	0.0461 (11)	−0.0116 (9)	0.0020 (8)	0.0004 (9)
N5	0.0397 (10)	0.0599 (12)	0.0443 (11)	−0.0034 (9)	−0.0035 (8)	0.0005 (9)
N6	0.0432 (10)	0.0618 (12)	0.0517 (12)	−0.0058 (9)	−0.0035 (9)	−0.0017 (9)
C7	0.093 (2)	0.192 (4)	0.059 (2)	−0.030 (2)	0.0190 (17)	0.000 (2)
C8	0.0578 (15)	0.099 (2)	0.0547 (16)	−0.0130 (14)	0.0075 (12)	0.0037 (14)
C9	0.0456 (13)	0.0638 (15)	0.0466 (14)	0.0002 (11)	−0.0002 (10)	0.0019 (11)
C10	0.0416 (12)	0.0599 (14)	0.0488 (13)	−0.0004 (11)	−0.0023 (10)	0.0010 (11)
C11	0.0431 (12)	0.0637 (16)	0.0551 (15)	−0.0021 (11)	−0.0050 (11)	0.0101 (12)
C12	0.0409 (11)	0.0600 (15)	0.0462 (13)	−0.0001 (11)	−0.0002 (10)	0.0006 (11)
C13	0.0508 (14)	0.0891 (19)	0.0507 (15)	−0.0103 (13)	−0.0026 (11)	0.0105 (13)
C14	0.0545 (14)	0.103 (2)	0.0444 (14)	−0.0125 (14)	−0.0050 (11)	0.0015 (14)
C15	0.0436 (13)	0.0717 (17)	0.0591 (15)	−0.0072 (12)	−0.0017 (11)	−0.0137 (13)
C16	0.0531 (13)	0.0570 (15)	0.0601 (15)	−0.0048 (11)	0.0082 (11)	−0.0028 (12)
C17	0.0516 (13)	0.0573 (14)	0.0449 (12)	0.0041 (11)	0.0007 (10)	−0.0003 (11)

S1—C10	1.674 (2)	C8—H8A	0.9700
F2—C15	1.358 (3)	C8—H8B	0.9700
N3—C9	1.295 (3)	C11—C12	1.467 (3)
N3—N4	1.374 (2)	C11—H11	0.9300
N4—C10	1.341 (3)	C12—C17	1.385 (3)
N4—H4	0.8600	C12—C13	1.387 (3)
N5—C10	1.382 (3)	C13—C14	1.383 (3)
N5—C9	1.385 (3)	C13—H13	0.9300
N5—N6	1.396 (2)	C14—C15	1.355 (3)
N6—C11	1.263 (3)	C14—H14	0.9300
C7—C8	1.490 (4)	C15—C16	1.368 (3)
C7—H7A	0.9600	C16—C17	1.381 (3)
C7—H7B	0.9600	C16—H16	0.9300
C7—H7C	0.9600	C17—H17	0.9300
C8—C9	1.487 (3)
C9—N3—N4	104.05 (17)	N4—C10—S1	127.43 (17)
C10—N4—N3	114.55 (18)	N5—C10—S1	130.33 (17)
C10—N4—H4	122.7	N6—C11—C12	120.7 (2)
N3—N4—H4	122.7	N6—C11—H11	119.7
C10—N5—C9	108.50 (18)	C12—C11—H11	119.7
C10—N5—N6	132.02 (18)	C17—C12—C13	119.1 (2)
C9—N5—N6	118.99 (18)	C17—C12—C11	121.6 (2)
C11—N6—N5	118.52 (19)	C13—C12—C11	119.2 (2)
C8—C7—H7A	109.5	C14—C13—C12	120.7 (2)
C8—C7—H7B	109.5	C14—C13—H13	119.6
H7A—C7—H7B	109.5	C12—C13—H13	119.6
C8—C7—H7C	109.5	C15—C14—C13	118.3 (2)
H7A—C7—H7C	109.5	C15—C14—H14	120.9
H7B—C7—H7C	109.5	C13—C14—H14	120.9
C9—C8—C7	113.6 (2)	C14—C15—F2	119.3 (2)
C9—C8—H8A	108.8	C14—C15—C16	123.0 (2)
C7—C8—H8A	108.8	F2—C15—C16	117.7 (2)
C9—C8—H8B	108.8	C15—C16—C17	118.6 (2)
C7—C8—H8B	108.8	C15—C16—H16	120.7
H8A—C8—H8B	107.7	C17—C16—H16	120.7
N3—C9—N5	110.71 (19)	C16—C17—C12	120.3 (2)
N3—C9—C8	126.9 (2)	C16—C17—H17	119.9
N5—C9—C8	122.3 (2)	C12—C17—H17	119.9
N4—C10—N5	102.12 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···S1i	0.86	2.48	3.3275 (19)	168
C11—H11···S1	0.93	2.55	3.222 (3)	129

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯S1i	0.86	2.48	3.3275 (19)	168
C11—H11⋯S1	0.93	2.55	3.222 (3)	129

Symmetry code: (i) .