5-(2,3,4,5,6-Penta-fluoro-phen-yl)-1,3,4-thia-diazol-2-amine.

The title compound, C(8)H(2)F(5)N(3)S, was synthesized by the reaction of perfluoro-benzoic acid and thio-semicarbazide. The dihedral angle between the thia-diazole and perfluoro-phenyl ring is 35.41 (6)°. In the crystal, inter-molecular N-H⋯N hydrogen bonds link the mol-ecules, forming a three-dimensional network.

Related literature

For the fungicidal and herbicidal activity of thia­diazole deriv­atives, see: Chen et al. (2000 ▶); Kidwai et al. (2000 ▶); Vicentini et al. (1998 ▶) and for their insecticidal activity, see: Arun et al. (1999 ▶); Wasfy et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H2F5N3S

M = 267.19

Monoclinic,

a = 11.897 (2) Å

b = 7.0680 (14) Å

c = 11.553 (2) Å

β = 104.66 (3)°

V = 939.8 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.40 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.889, T max = 0.961

3428 measured reflections

1709 independent reflections

1283 reflections with I > 2σ(I)

R int = 0.064

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.128

S = 1.00

1709 reflections

154 parameters

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536810039723/er2081sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039723/er2081Isup2.hkl

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

C8H2F5N3S	F(000) = 528
Mr = 267.19	Dx = 1.888 Mg m−3
Monoclinic, P21/c	Melting point = 523–525 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.897 (2) Å	Cell parameters from 25 reflections
b = 7.0680 (14) Å	θ = 9–13°
c = 11.553 (2) Å	µ = 0.40 mm−1
β = 104.66 (3)°	T = 293 K
V = 939.8 (3) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1283 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
graphite	θmax = 25.3°, θmin = 1.8°
ω/2θ scans	h = −14→0
Absorption correction: ψ scan (North et al., 1968)	k = −8→8
Tmin = 0.889, Tmax = 0.961	l = −13→13
3428 measured reflections	3 standard reflections every 200 reflections
1709 independent reflections	intensity decay: 1%

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.128	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.080P)2] where P = (Fo2 + 2Fc2)/3
1709 reflections	(Δ/σ)max < 0.001
154 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
S	0.82940 (7)	0.06662 (10)	0.05893 (6)	0.0461 (3)
F1	0.78775 (15)	−0.3360 (2)	−0.00245 (14)	0.0569 (5)
C1	0.9155 (2)	0.2602 (4)	0.0479 (2)	0.0404 (6)
N1	0.9659 (2)	0.3683 (4)	0.1416 (2)	0.0524 (6)
H1A	1.0105	0.4601	0.1330	0.063*
H1B	0.9537	0.3459	0.2106	0.063*
C2	0.8165 (2)	0.0294 (4)	−0.0925 (2)	0.0389 (6)
F2	0.65099 (17)	−0.6042 (2)	−0.12921 (18)	0.0685 (6)
N2	0.9298 (2)	0.2855 (4)	−0.06011 (19)	0.0472 (6)
F3	0.53266 (17)	−0.5342 (3)	−0.35867 (18)	0.0747 (6)
N3	0.8725 (2)	0.1519 (3)	−0.13946 (19)	0.0451 (6)
C3	0.7437 (2)	−0.1198 (4)	−0.1630 (2)	0.0387 (6)
F4	0.55308 (16)	−0.1942 (3)	−0.45890 (14)	0.0689 (6)
C4	0.7312 (2)	−0.2972 (4)	−0.1154 (2)	0.0429 (6)
F5	0.68393 (17)	0.0780 (2)	−0.33282 (15)	0.0609 (5)
C5	0.6609 (3)	−0.4358 (4)	−0.1800 (3)	0.0489 (7)
C6	0.6009 (2)	−0.4016 (4)	−0.2954 (3)	0.0502 (7)
C7	0.6116 (2)	−0.2282 (4)	−0.3459 (2)	0.0482 (7)
C8	0.6812 (2)	−0.0900 (4)	−0.2800 (2)	0.0453 (7)

	U11	U22	U33	U12	U13	U23
S	0.0633 (5)	0.0429 (4)	0.0347 (4)	−0.0129 (3)	0.0171 (3)	−0.0005 (3)
F1	0.0665 (10)	0.0469 (10)	0.0521 (10)	−0.0049 (8)	0.0052 (8)	0.0130 (8)
C1	0.0472 (14)	0.0406 (15)	0.0352 (13)	−0.0044 (12)	0.0139 (12)	−0.0027 (11)
N1	0.0725 (16)	0.0530 (15)	0.0339 (12)	−0.0221 (13)	0.0176 (11)	−0.0081 (10)
C2	0.0477 (14)	0.0358 (14)	0.0354 (13)	−0.0023 (11)	0.0147 (12)	−0.0012 (11)
F2	0.0801 (13)	0.0418 (10)	0.0824 (14)	−0.0148 (9)	0.0184 (11)	0.0058 (9)
N2	0.0600 (14)	0.0494 (14)	0.0368 (12)	−0.0185 (11)	0.0206 (11)	−0.0092 (10)
F3	0.0815 (13)	0.0659 (13)	0.0740 (13)	−0.0330 (10)	0.0145 (11)	−0.0233 (10)
N3	0.0586 (14)	0.0442 (13)	0.0362 (12)	−0.0136 (11)	0.0191 (11)	−0.0087 (10)
C3	0.0450 (14)	0.0351 (14)	0.0378 (13)	−0.0027 (11)	0.0139 (11)	−0.0040 (11)
F4	0.0762 (12)	0.0821 (14)	0.0411 (9)	−0.0162 (11)	0.0012 (8)	−0.0056 (9)
C4	0.0458 (15)	0.0405 (15)	0.0426 (15)	−0.0010 (12)	0.0114 (12)	0.0025 (12)
F5	0.0840 (12)	0.0443 (10)	0.0477 (10)	−0.0082 (9)	0.0041 (9)	0.0086 (7)
C5	0.0553 (16)	0.0349 (15)	0.0603 (18)	−0.0060 (13)	0.0217 (14)	−0.0005 (13)
C6	0.0508 (16)	0.0486 (17)	0.0531 (17)	−0.0159 (14)	0.0165 (14)	−0.0172 (13)
C7	0.0492 (16)	0.0547 (18)	0.0406 (15)	−0.0051 (13)	0.0108 (13)	−0.0087 (13)
C8	0.0542 (16)	0.0404 (15)	0.0429 (15)	−0.0015 (12)	0.0155 (13)	−0.0008 (11)

S—C1	1.733 (3)	N2—N3	1.372 (3)
S—C2	1.737 (3)	F3—C6	1.331 (3)
F1—C4	1.336 (3)	C3—C8	1.383 (4)
C1—N2	1.313 (3)	C3—C4	1.392 (4)
C1—N1	1.337 (3)	F4—C7	1.336 (3)
N1—H1A	0.8600	C4—C5	1.379 (4)
N1—H1B	0.8600	F5—C8	1.339 (3)
C2—N3	1.292 (3)	C5—C6	1.365 (5)
C2—C3	1.473 (4)	C6—C7	1.377 (4)
F2—C5	1.345 (3)	C7—C8	1.379 (4)
C1—S—C2	87.05 (12)	F1—C4—C5	118.0 (3)
N2—C1—N1	123.5 (2)	F1—C4—C3	119.5 (2)
N2—C1—S	113.5 (2)	C5—C4—C3	122.4 (3)
N1—C1—S	122.92 (19)	F2—C5—C6	120.1 (3)
C1—N1—H1A	120.0	F2—C5—C4	120.0 (3)
C1—N1—H1B	120.0	C6—C5—C4	119.9 (3)
H1A—N1—H1B	120.0	F3—C6—C5	120.5 (3)
N3—C2—C3	122.8 (2)	F3—C6—C7	120.2 (3)
N3—C2—S	113.4 (2)	C5—C6—C7	119.3 (2)
C3—C2—S	123.72 (19)	F4—C7—C6	119.5 (2)
C1—N2—N3	112.3 (2)	F4—C7—C8	120.3 (3)
C2—N3—N2	113.8 (2)	C6—C7—C8	120.2 (3)
C8—C3—C4	116.0 (2)	F5—C8—C7	117.2 (2)
C8—C3—C2	121.8 (2)	F5—C8—C3	120.8 (2)
C4—C3—C2	122.2 (2)	C7—C8—C3	122.1 (3)
C2—S—C1—N2	−0.2 (2)	F1—C4—C5—C6	179.5 (3)
C2—S—C1—N1	−177.7 (3)	C3—C4—C5—C6	0.3 (4)
C1—S—C2—N3	0.2 (2)	F2—C5—C6—F3	−0.4 (4)
C1—S—C2—C3	−176.3 (2)	C4—C5—C6—F3	−179.9 (3)
N1—C1—N2—N3	177.7 (3)	F2—C5—C6—C7	179.7 (2)
S—C1—N2—N3	0.2 (3)	C4—C5—C6—C7	0.2 (4)
C3—C2—N3—N2	176.4 (2)	F3—C6—C7—F4	0.0 (4)
S—C2—N3—N2	−0.2 (3)	C5—C6—C7—F4	179.9 (3)
C1—N2—N3—C2	0.0 (4)	F3—C6—C7—C8	179.3 (3)
N3—C2—C3—C8	−34.3 (4)	C5—C6—C7—C8	−0.8 (4)
S—C2—C3—C8	141.9 (2)	F4—C7—C8—F5	2.1 (4)
N3—C2—C3—C4	147.3 (3)	C6—C7—C8—F5	−177.2 (3)
S—C2—C3—C4	−36.4 (4)	F4—C7—C8—C3	−179.6 (2)
C8—C3—C4—F1	−179.2 (2)	C6—C7—C8—C3	1.1 (4)
C2—C3—C4—F1	−0.8 (4)	C4—C3—C8—F5	177.6 (2)
C8—C3—C4—C5	0.0 (4)	C2—C3—C8—F5	−0.8 (4)
C2—C3—C4—C5	178.4 (3)	C4—C3—C8—C7	−0.6 (4)
F1—C4—C5—F2	−0.1 (4)	C2—C3—C8—C7	−179.1 (3)
C3—C4—C5—F2	−179.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.86	2.18	3.001 (4)	160
N1—H1B···N3ii	0.86	2.19	3.013 (3)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.86	2.18	3.001 (4)	160
N1—H1B⋯N3ii	0.86	2.19	3.013 (3)	161

Symmetry codes: (i) ; (ii) .