5-(3-Fluoro-phen-yl)-1,3,4-thia-diazol-2-amine.

The title compound, C(8)H(6)FN(3)S, was synthesized by the reaction of 3-fluoro-benzoic acid and thio-semicarbazide. The dihedral angle between the planes of the thia-diazole and benzene rings is 37.3 (2)°. In the structure, two crystallographically independent mol-ecules form a centrosymmetric dimer, in which two inter-molecular N-H⋯N hydrogen bonds generate an R(2) (2)(8) motif.

Related literature

For the biological activity of 1,3,4-thiadiazole derivatives, see: Nakagawa et al. (1996 ▶); Wang et al. (1999 ▶). For a similar structure, see: Wan et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H6FN3S

M = 195.23

Monoclinic,

a = 11.345 (2) Å

b = 7.3130 (15) Å

c = 11.269 (2) Å

β = 111.64 (3)°

V = 869.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.935, T max = 0.967

1667 measured reflections

1584 independent reflections

1177 reflections with I > 2σ(I)

R int = 0.021

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.124

S = 1.01

1584 reflections

118 parameters

13 restraints

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; 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/S1600536809019333/at2787sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019333/at2787Isup2.hkl

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

C8H6FN3S	F(000) = 400
Mr = 195.23	Dx = 1.492 Mg m−3
Monoclinic, P21/c	Melting point: 515 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.345 (2) Å	Cell parameters from 25 reflections
b = 7.3130 (15) Å	θ = 10–13°
c = 11.269 (2) Å	µ = 0.34 mm−1
β = 111.64 (3)°	T = 293 K
V = 869.0 (3) Å3	Block, colourless
Z = 4	0.20 × 0.10 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1177 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 25.3°, θmin = 1.9°
ω/2θ scans	h = −13→0
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.935, Tmax = 0.967	l = −12→13
1667 measured reflections	3 standard reflections every 200 reflections
1584 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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3
1584 reflections	(Δ/σ)max < 0.001
118 parameters	Δρmax = 0.37 e Å−3
13 restraints	Δρmin = −0.25 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	0.82144 (7)	0.08639 (11)	0.55908 (6)	0.0548 (3)
F	0.5162 (3)	−0.2428 (3)	0.0198 (2)	0.1125 (9)
N1	0.8658 (2)	0.1443 (3)	0.3566 (2)	0.0523 (6)
C1	0.7322 (3)	−0.2918 (5)	0.3984 (3)	0.0713 (9)
H1B	0.7804	−0.3036	0.4850	0.086*
N2	0.9262 (2)	0.2841 (3)	0.4381 (2)	0.0551 (6)
C2	0.6592 (4)	−0.4354 (5)	0.3322 (4)	0.0817 (11)
H2B	0.6585	−0.5443	0.3746	0.098*
N3	0.9606 (3)	0.3931 (4)	0.6429 (2)	0.0733 (9)
H3A	1.0043	0.4846	0.6340	0.088*
H3B	0.9481	0.3787	0.7131	0.088*
C3	0.5871 (4)	−0.4202 (5)	0.2040 (4)	0.0822 (12)
H3C	0.5378	−0.5175	0.1592	0.099*
C4	0.5898 (3)	−0.2597 (6)	0.1447 (3)	0.0741 (10)
C5	0.6637 (3)	−0.1132 (4)	0.2071 (3)	0.0639 (9)
H5A	0.6658	−0.0066	0.1628	0.077*
C6	0.7338 (3)	−0.1272 (4)	0.3350 (3)	0.0516 (7)
C7	0.8082 (3)	0.0307 (4)	0.4039 (2)	0.0475 (7)
C8	0.9121 (3)	0.2733 (4)	0.5476 (2)	0.0499 (7)

	U11	U22	U33	U12	U13	U23
S	0.0686 (5)	0.0626 (5)	0.0402 (4)	−0.0130 (4)	0.0282 (3)	0.0002 (3)
F	0.1200 (19)	0.122 (2)	0.0888 (16)	−0.0253 (16)	0.0307 (14)	−0.0193 (15)
N1	0.0646 (15)	0.0583 (14)	0.0421 (12)	−0.0113 (12)	0.0293 (11)	−0.0079 (11)
C1	0.070 (2)	0.068 (2)	0.073 (2)	−0.0121 (18)	0.0235 (17)	0.0023 (18)
N2	0.0753 (16)	0.0580 (15)	0.0433 (12)	−0.0172 (13)	0.0353 (12)	−0.0097 (11)
C2	0.074 (2)	0.060 (2)	0.112 (3)	−0.0081 (19)	0.035 (2)	0.001 (2)
N3	0.110 (2)	0.0800 (19)	0.0452 (14)	−0.0379 (17)	0.0462 (15)	−0.0191 (13)
C3	0.074 (2)	0.079 (3)	0.104 (3)	−0.020 (2)	0.045 (2)	−0.040 (2)
C4	0.075 (2)	0.091 (3)	0.062 (2)	−0.024 (2)	0.0319 (18)	−0.0344 (19)
C5	0.075 (2)	0.068 (2)	0.0514 (17)	−0.0144 (17)	0.0271 (16)	−0.0140 (16)
C6	0.0557 (17)	0.0533 (17)	0.0519 (16)	0.0000 (13)	0.0270 (14)	−0.0051 (13)
C7	0.0541 (16)	0.0513 (16)	0.0421 (14)	0.0000 (13)	0.0236 (13)	−0.0013 (12)
C8	0.0634 (18)	0.0556 (17)	0.0374 (13)	−0.0068 (14)	0.0265 (13)	−0.0025 (13)

S—C8	1.744 (3)	C2—H2B	0.9300
S—C7	1.747 (3)	N3—C8	1.338 (3)
F—C4	1.351 (4)	N3—H3A	0.8600
N1—C7	1.288 (3)	N3—H3B	0.8600
N1—N2	1.377 (3)	C3—C4	1.357 (5)
C1—C2	1.375 (5)	C3—H3C	0.9300
C1—C6	1.403 (4)	C4—C5	1.382 (4)
C1—H1B	0.9300	C5—C6	1.369 (4)
N2—C8	1.303 (3)	C5—H5A	0.9300
C2—C3	1.378 (5)	C6—C7	1.472 (4)
C8—S—C7	86.76 (13)	F—C4—C3	118.3 (3)
C7—N1—N2	114.0 (2)	F—C4—C5	119.0 (4)
C2—C1—C6	119.8 (3)	C3—C4—C5	122.7 (3)
C2—C1—H1B	120.1	C6—C5—C4	119.0 (3)
C6—C1—H1B	120.1	C6—C5—H5A	120.5
C8—N2—N1	112.5 (2)	C4—C5—H5A	120.5
C1—C2—C3	120.9 (4)	C5—C6—C1	119.3 (3)
C1—C2—H2B	119.6	C5—C6—C7	119.6 (3)
C3—C2—H2B	119.6	C1—C6—C7	121.1 (3)
C8—N3—H3A	120.0	N1—C7—C6	124.6 (2)
C8—N3—H3B	120.0	N1—C7—S	113.2 (2)
H3A—N3—H3B	120.0	C6—C7—S	122.1 (2)
C4—C3—C2	118.3 (3)	N2—C8—N3	124.3 (3)
C4—C3—H3C	120.9	N2—C8—S	113.5 (2)
C2—C3—H3C	120.9	N3—C8—S	122.19 (19)
C7—N1—N2—C8	−0.2 (4)	N2—N1—C7—S	0.5 (3)
C6—C1—C2—C3	−0.1 (5)	C5—C6—C7—N1	−36.0 (4)
C1—C2—C3—C4	−0.1 (6)	C1—C6—C7—N1	144.6 (3)
C2—C3—C4—F	−178.1 (3)	C5—C6—C7—S	141.4 (3)
C2—C3—C4—C5	1.3 (6)	C1—C6—C7—S	−37.9 (4)
F—C4—C5—C6	177.0 (3)	C8—S—C7—N1	−0.4 (2)
C3—C4—C5—C6	−2.4 (5)	C8—S—C7—C6	−178.2 (2)
C4—C5—C6—C1	2.2 (5)	N1—N2—C8—N3	−179.5 (3)
C4—C5—C6—C7	−177.2 (3)	N1—N2—C8—S	−0.1 (3)
C2—C1—C6—C5	−1.0 (5)	C7—S—C8—N2	0.3 (2)
C2—C1—C6—C7	178.4 (3)	C7—S—C8—N3	179.7 (3)
N2—N1—C7—C6	178.1 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···N2i	0.86	2.14	2.981 (5)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N2i	0.86	2.14	2.981 (5)	165

Symmetry code: (i) .