5-(4-Pyrid-yl)-1,3,4-thia-diazole-2(3H)-thione.

The title compound C(7)H(5)N(3)S(2), occurs as the thione tautomer in the solid state; the dihedral angle between the pyridine and thia-diazole ring planes is 2.08 (6)°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds, generating C(8) chains propagating in [010].

Related literature

For details of the synthesis, see: Song et al. (2005 ▶). For the biological activity of related compounds, see: Liu et al. (2007 ▶, 2009a ▶,b ▶,c ▶).

Experimental

Crystal data

C7H5N3S2

M = 195.26

Monoclinic,

a = 7.837 (3) Å

b = 15.971 (5) Å

c = 6.694 (2) Å

β = 103.680 (4)°

V = 814.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 113 K

0.20 × 0.20 × 0.08 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.891, T max = 0.954

8141 measured reflections

1928 independent reflections

1642 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.076

S = 1.06

1928 reflections

113 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 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: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810052116/hb5770sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052116/hb5770Isup2.hkl

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

C7H5N3S2	F(000) = 400
Mr = 195.26	Dx = 1.593 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2887 reflections
a = 7.837 (3) Å	θ = 2.6–27.9°
b = 15.971 (5) Å	µ = 0.59 mm−1
c = 6.694 (2) Å	T = 113 K
β = 103.680 (4)°	Prism, colorless
V = 814.1 (5) Å3	0.20 × 0.20 × 0.08 mm
Z = 4

Rigaku Saturn CCD diffractometer	1928 independent reflections
Radiation source: fine-focus sealed tube	1642 reflections with I > 2σ(I)
graphite	Rint = 0.033
Detector resolution: 14.63 pixels mm-1	θmax = 27.8°, θmin = 2.6°
ω and φ scans	h = −10→10
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −20→21
Tmin = 0.891, Tmax = 0.954	l = −8→8
8141 measured reflections

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0461P)2] where P = (Fo2 + 2Fc2)/3
1928 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.44 e Å−3
1 restraint	Δρmin = −0.21 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
S1	0.40446 (4)	0.02171 (2)	0.20702 (6)	0.01704 (11)
S2	0.60139 (5)	−0.14291 (2)	0.26909 (6)	0.02389 (13)
N1	0.27180 (16)	−0.11033 (7)	0.30185 (19)	0.0159 (3)
N2	0.13949 (15)	−0.05360 (7)	0.28751 (18)	0.0151 (2)
N3	−0.14570 (15)	0.23252 (7)	0.15350 (18)	0.0154 (3)
C1	0.42543 (17)	−0.08492 (8)	0.2646 (2)	0.0159 (3)
C2	0.19024 (17)	0.01952 (8)	0.2396 (2)	0.0138 (3)
C3	0.07477 (17)	0.09310 (8)	0.2109 (2)	0.0138 (3)
C4	0.13479 (18)	0.17060 (8)	0.1615 (2)	0.0160 (3)
H4	0.2515	0.1772	0.1463	0.019*
C5	0.02020 (18)	0.23800 (8)	0.1349 (2)	0.0159 (3)
H5	0.0617	0.2909	0.1018	0.019*
C6	−0.20252 (18)	0.15758 (8)	0.2012 (2)	0.0156 (3)
H6	−0.3202	0.1529	0.2145	0.019*
C7	−0.09795 (17)	0.08668 (9)	0.2320 (2)	0.0156 (3)
H7	−0.1426	0.0348	0.2667	0.019*
H1	0.244 (3)	−0.1638 (6)	0.325 (3)	0.047 (6)*

	U11	U22	U33	U12	U13	U23
S1	0.01417 (18)	0.01237 (18)	0.0254 (2)	−0.00003 (12)	0.00638 (15)	0.00162 (13)
S2	0.0190 (2)	0.0213 (2)	0.0318 (3)	0.00798 (14)	0.00682 (17)	0.00402 (15)
N1	0.0171 (6)	0.0109 (5)	0.0204 (7)	0.0014 (4)	0.0058 (5)	0.0016 (5)
N2	0.0171 (6)	0.0117 (5)	0.0170 (6)	0.0013 (5)	0.0048 (5)	0.0001 (4)
N3	0.0164 (6)	0.0132 (6)	0.0158 (6)	−0.0001 (5)	0.0021 (5)	−0.0016 (4)
C1	0.0169 (7)	0.0139 (6)	0.0162 (7)	0.0003 (5)	0.0025 (5)	−0.0005 (5)
C2	0.0142 (6)	0.0137 (6)	0.0137 (7)	−0.0005 (5)	0.0039 (5)	−0.0014 (5)
C3	0.0160 (7)	0.0136 (6)	0.0115 (7)	0.0002 (5)	0.0026 (5)	−0.0014 (5)
C4	0.0146 (7)	0.0158 (7)	0.0179 (7)	−0.0014 (5)	0.0046 (6)	−0.0002 (5)
C5	0.0183 (7)	0.0123 (6)	0.0167 (7)	−0.0022 (5)	0.0037 (6)	0.0000 (5)
C6	0.0142 (6)	0.0170 (7)	0.0158 (7)	−0.0015 (5)	0.0040 (6)	−0.0017 (5)
C7	0.0177 (7)	0.0126 (7)	0.0164 (7)	−0.0025 (5)	0.0042 (6)	−0.0006 (5)

S1—C2	1.7437 (15)	C2—C3	1.4679 (18)
S1—C1	1.7452 (15)	C3—C4	1.3916 (19)
S2—C1	1.6555 (14)	C3—C7	1.3974 (18)
N1—C1	1.3485 (18)	C4—C5	1.3862 (19)
N1—N2	1.3631 (16)	C4—H4	0.9500
N1—H1	0.902 (9)	C5—H5	0.9500
N2—C2	1.2980 (17)	C6—C7	1.3844 (19)
N3—C5	1.3378 (18)	C6—H6	0.9500
N3—C6	1.3417 (17)	C7—H7	0.9500
C2—S1—C1	89.77 (6)	C7—C3—C2	120.65 (12)
C1—N1—N2	118.98 (11)	C5—C4—C3	118.43 (13)
C1—N1—H1	125.1 (12)	C5—C4—H4	120.8
N2—N1—H1	115.7 (13)	C3—C4—H4	120.8
C2—N2—N1	110.06 (11)	N3—C5—C4	123.48 (12)
C5—N3—C6	117.71 (11)	N3—C5—H5	118.3
N1—C1—S2	127.20 (11)	C4—C5—H5	118.3
N1—C1—S1	107.03 (10)	N3—C6—C7	123.17 (13)
S2—C1—S1	125.77 (8)	N3—C6—H6	118.4
N2—C2—C3	122.50 (12)	C7—C6—H6	118.4
N2—C2—S1	114.16 (10)	C6—C7—C3	118.57 (12)
C3—C2—S1	123.33 (10)	C6—C7—H7	120.7
C4—C3—C7	118.64 (12)	C3—C7—H7	120.7
C4—C3—C2	120.71 (12)
C1—N1—N2—C2	−0.77 (17)	N2—C2—C3—C7	−0.8 (2)
N2—N1—C1—S2	−178.87 (10)	S1—C2—C3—C7	177.65 (11)
N2—N1—C1—S1	0.50 (15)	C7—C3—C4—C5	−0.1 (2)
C2—S1—C1—N1	−0.08 (10)	C2—C3—C4—C5	179.66 (12)
C2—S1—C1—S2	179.29 (11)	C6—N3—C5—C4	0.3 (2)
N1—N2—C2—C3	179.24 (12)	C3—C4—C5—N3	−0.3 (2)
N1—N2—C2—S1	0.65 (15)	C5—N3—C6—C7	0.1 (2)
C1—S1—C2—N2	−0.34 (11)	N3—C6—C7—C3	−0.5 (2)
C1—S1—C2—C3	−178.92 (12)	C4—C3—C7—C6	0.5 (2)
N2—C2—C3—C4	179.40 (13)	C2—C3—C7—C6	−179.28 (12)
S1—C2—C3—C4	−2.14 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N3i	0.90 (1)	1.85 (1)	2.7395 (19)	169 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N3i	0.90 (1)	1.85 (1)	2.7395 (19)	169 (2)

Symmetry code: (i) .