2,2'-[(1,3,4-Thia-diazole-2,5-di-yl)bis-(sulfanedi-yl)]diaceto-nitrile.

In the title compound, C6H4N4S3, the 1,3,4-thia-diazole ring is essentially planar, with an r.m.s. deviation of 0.001 Å. The two N-C-S-C torsion angles in the mol-ecule are -23.41 (15) and 0.62 (14)°. One aceto-nitrile group is above the plane of the 1,3,4-thia-diazole ring and the other is below it, indicating syn and anti orientations. In the crystal, C-H⋯N hydrogen bonds link the molecules into ribbons along [010].

Related literature

For the broad spectrum of biological activities of thia­diazole-containing compounds, see: Padmavathi et al. (2009 ▶); Karegoudar et al. (2008 ▶); Wei et al. (2009 ▶); Gupta et al. (2009 ▶); Pattanayak et al. (2009 ▶); Cressier et al. (2009 ▶).

Experimental

Crystal data

C6H4N4S3

M = 228.34

Monoclinic,

a = 8.5305 (7) Å

b = 14.2102 (11) Å

c = 7.8803 (6) Å

β = 104.3810 (11)°

V = 925.32 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.76 mm−1

T = 150 K

0.24 × 0.08 × 0.06 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2013 ▶) T min = 0.82, T max = 0.96

16625 measured reflections

2450 independent reflections

2155 reflections with I > 2σ(I)

R int = 0.040

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.074

S = 1.05

2450 reflections

118 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2013 ▶); cell refinement: SAINT (Bruker, 2013 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXT (Sheldrick, 2008) ▶; program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008) ▶; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813032194/hg5363sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813032194/hg5363Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813032194/hg5363Isup3.cml

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

C6H4N4S3	F(000) = 464
Mr = 228.34	Dx = 1.639 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9961 reflections
a = 8.5305 (7) Å	θ = 2.9–29.1°
b = 14.2102 (11) Å	µ = 0.76 mm−1
c = 7.8803 (6) Å	T = 150 K
β = 104.3810 (11)°	Column, pale gold
V = 925.32 (13) Å3	0.24 × 0.08 × 0.06 mm
Z = 4

Bruker SMART APEX CCD diffractometer	2450 independent reflections
Radiation source: fine-focus sealed tube	2155 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
Detector resolution: 8.3660 pixels mm-1	θmax = 29.1°, θmin = 2.5°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −19→19
Tmin = 0.82, Tmax = 0.96	l = −10→10
16625 measured reflections

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.074	W = 1/[Σ2(FO2) + (0.0348P)2 + 0.4414P] Where P = (FO2 + 2FC2)/3
S = 1.05	(Δ/σ)max < 0.001
2450 reflections	Δρmax = 0.56 e Å−3
118 parameters	Δρmin = −0.24 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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	0.24557 (4)	0.24679 (2)	0.77612 (5)	0.0199 (1)
S2	0.35261 (4)	0.45127 (3)	0.80614 (5)	0.0225 (1)
S3	−0.02136 (4)	0.11179 (3)	0.59651 (5)	0.0217 (1)
N1	0.07063 (16)	0.38153 (9)	0.61222 (18)	0.0246 (4)
N2	−0.01784 (15)	0.29982 (9)	0.56140 (18)	0.0232 (4)
N3	0.31454 (18)	0.46664 (10)	0.33409 (18)	0.0286 (4)
N4	−0.40861 (18)	0.23221 (12)	0.5806 (2)	0.0370 (5)
C1	0.20800 (17)	0.36440 (10)	0.72254 (19)	0.0188 (4)
C2	0.05731 (17)	0.22555 (10)	0.63639 (18)	0.0178 (4)
C3	0.29143 (18)	0.53720 (10)	0.6312 (2)	0.0223 (4)
C4	0.30417 (18)	0.49844 (10)	0.4636 (2)	0.0222 (4)
C5	−0.20837 (18)	0.14204 (11)	0.4383 (2)	0.0240 (4)
C6	−0.32061 (18)	0.19370 (11)	0.5168 (2)	0.0247 (4)
H3A	0.17830	0.55670	0.62240	0.0270*
H3B	0.36100	0.59370	0.65920	0.0270*
H5A	−0.18280	0.18080	0.34420	0.0290*
H5B	−0.26140	0.08360	0.38420	0.0290*

	U11	U22	U33	U12	U13	U23
S1	0.0170 (2)	0.0195 (2)	0.0210 (2)	−0.0004 (1)	0.0001 (1)	0.0025 (1)
S2	0.0207 (2)	0.0212 (2)	0.0224 (2)	−0.0041 (1)	−0.0007 (1)	0.0015 (1)
S3	0.0205 (2)	0.0189 (2)	0.0243 (2)	−0.0020 (1)	0.0029 (1)	−0.0006 (1)
N1	0.0195 (6)	0.0210 (6)	0.0302 (7)	−0.0028 (5)	0.0006 (5)	0.0037 (5)
N2	0.0185 (6)	0.0212 (6)	0.0274 (7)	−0.0031 (5)	0.0012 (5)	0.0025 (5)
N3	0.0310 (7)	0.0273 (7)	0.0261 (7)	−0.0034 (6)	0.0042 (6)	0.0016 (6)
N4	0.0244 (7)	0.0490 (9)	0.0352 (8)	0.0019 (7)	0.0031 (6)	−0.0032 (7)
C1	0.0195 (7)	0.0175 (6)	0.0194 (7)	−0.0010 (5)	0.0050 (5)	0.0017 (5)
C2	0.0156 (6)	0.0217 (7)	0.0164 (6)	−0.0014 (5)	0.0043 (5)	0.0004 (5)
C3	0.0232 (7)	0.0173 (7)	0.0260 (8)	0.0014 (5)	0.0051 (6)	0.0023 (6)
C4	0.0202 (7)	0.0180 (7)	0.0265 (8)	−0.0026 (5)	0.0025 (6)	0.0041 (6)
C5	0.0233 (7)	0.0272 (8)	0.0187 (7)	−0.0049 (6)	0.0000 (5)	−0.0028 (6)
C6	0.0187 (7)	0.0299 (8)	0.0215 (7)	−0.0047 (6)	−0.0026 (6)	0.0009 (6)

S1—C1	1.7340 (15)	N3—C4	1.140 (2)
S1—C2	1.7333 (15)	N4—C6	1.142 (2)
S2—C1	1.7538 (15)	C3—C4	1.460 (2)
S2—C3	1.8184 (15)	C5—C6	1.460 (2)
S3—C2	1.7486 (15)	C3—H3A	0.9900
S3—C5	1.8155 (16)	C3—H3B	0.9900
N1—N2	1.3885 (19)	C5—H5A	0.9900
N1—C1	1.297 (2)	C5—H5B	0.9900
N2—C2	1.2984 (19)
C1—S1—C2	85.82 (7)	S3—C5—C6	112.64 (11)
C1—S2—C3	98.35 (7)	N4—C6—C5	178.33 (17)
C2—S3—C5	97.88 (7)	S2—C3—H3A	109.00
N2—N1—C1	111.85 (12)	S2—C3—H3B	109.00
N1—N2—C2	112.14 (13)	C4—C3—H3A	109.00
S1—C1—S2	121.11 (9)	C4—C3—H3B	109.00
S1—C1—N1	115.19 (11)	H3A—C3—H3B	108.00
S2—C1—N1	123.63 (11)	S3—C5—H5A	109.00
S1—C2—S3	121.93 (8)	S3—C5—H5B	109.00
S1—C2—N2	114.99 (11)	C6—C5—H5A	109.00
S3—C2—N2	123.07 (11)	C6—C5—H5B	109.00
S2—C3—C4	111.14 (10)	H5A—C5—H5B	108.00
N3—C4—C3	178.79 (16)
C2—S1—C1—S2	−177.61 (10)	C5—S3—C2—N2	0.62 (14)
C2—S1—C1—N1	−0.51 (12)	C2—S3—C5—C6	−68.78 (12)
C1—S1—C2—S3	179.01 (10)	C1—N1—N2—C2	0.16 (19)
C1—S1—C2—N2	0.61 (12)	N2—N1—C1—S1	0.32 (17)
C3—S2—C1—S1	153.44 (9)	N2—N1—C1—S2	177.33 (11)
C3—S2—C1—N1	−23.41 (15)	N1—N2—C2—S1	−0.57 (17)
C1—S2—C3—C4	−60.50 (12)	N1—N2—C2—S3	−178.96 (11)
C5—S3—C2—S1	−177.66 (9)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···N1i	0.99	2.60	3.407 (2)	139
C5—H5B···N3ii	0.99	2.35	3.267 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯N1i	0.99	2.60	3.407 (2)	139
C5—H5B⋯N3ii	0.99	2.35	3.267 (2)	153

Symmetry codes: (i) ; (ii) .