2,2′-(1,4-Butane­diyldithio)bis­(1,3,4-thia­diazole)

In the title compound, C₈H₁₀N₄S₄, there is a twofold rotation axis at the mid-point of the central C—C bond. With the exception of the methylene H atoms, all atoms lie on a mirror plane. In the crystal structure, mol­ecules form a brick-wall motif, via π–π stacking inter­actions, in the ab plane. In addition, C—H...N hydrogen bonds together with weak N...S, and S...S inter­actions promote two-dimensional packing parallel to the ac plane, and form a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.028
• wR factor = 0.087
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.05
PLAT322_ALERT_2_C Check Hybridisation of  S1     in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          5

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2; data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker 2004); software used to prepare material for publication: SHELXTL.

2,2'-(1,4-Butanediyldithio)bis(1,3,4-thiadiazole)

Crystal data

C8H10N4S4	F(000) = 300
Mr = 290.44	Dx = 1.568 Mg m^−3
Monoclinic, C2/m	Melting point: 94 K
Hall symbol: -C 2y	Mo Kα radiation, λ = 0.71073 Å
a = 17.333 (3) Å	Cell parameters from 1643 reflections
b = 6.9652 (14) Å	θ = 2.5–28.3°
c = 5.355 (1) Å	µ = 0.75 mm^−1
β = 107.926 (3)°	T = 291 K
V = 615.1 (2) Å^3	Plate, colourless
Z = 2	0.37 × 0.22 × 0.07 mm

Data collection

Bruker SMART CCD area-detector diffractometer	631 independent reflections
Radiation source: fine-focus sealed tube	628 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.010
φ and ω scans	θmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −20→19
Tmin = 0.768, Tmax = 0.949	k = −8→4
1629 measured reflections	l = −6→6

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0425P)^2 + 1.2117P] where P = (Fo^2 + 2Fc^2)/3
631 reflections	(Δ/σ)max < 0.001
49 parameters	Δρmax = 0.46 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
S1	0.20691 (5)	0.0000	0.83005 (15)	0.0359 (3)
S2	0.32221 (4)	0.0000	0.49775 (15)	0.0357 (3)
N1	0.15985 (16)	0.0000	0.3272 (5)	0.0387 (7)
N2	0.09044 (17)	0.0000	0.4008 (6)	0.0447 (7)
C1	0.22525 (18)	0.0000	0.5301 (6)	0.0306 (6)
C2	0.1064 (2)	0.0000	0.6542 (7)	0.0397 (8)
H2	0.0658	0.0000	0.7343	0.048*
C3	0.38371 (18)	0.0000	0.8403 (6)	0.0361 (7)
H3A	0.3716	0.1129	0.9275	0.043*	0.50
H3B	0.3716	−0.1129	0.9275	0.043*	0.50
C4	0.47288 (18)	0.0000	0.8568 (6)	0.0394 (8)
H4A	0.4846	0.1127	0.7683	0.047*	0.50
H4B	0.4846	−0.1127	0.7683	0.047*	0.50

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0294 (4)	0.0502 (5)	0.0264 (4)	0.000	0.0064 (3)	0.000
S2	0.0252 (4)	0.0526 (5)	0.0279 (4)	0.000	0.0062 (3)	0.000
N1	0.0259 (13)	0.0574 (18)	0.0301 (14)	0.000	0.0047 (10)	0.000
N2	0.0257 (13)	0.064 (2)	0.0409 (16)	0.000	0.0051 (11)	0.000
C1	0.0288 (15)	0.0354 (15)	0.0253 (14)	0.000	0.0052 (11)	0.000
C2	0.0293 (15)	0.056 (2)	0.0345 (17)	0.000	0.0102 (13)	0.000
C3	0.0255 (15)	0.055 (2)	0.0244 (14)	0.000	0.0036 (11)	0.000
C4	0.0281 (16)	0.055 (2)	0.0314 (18)	0.000	0.0043 (14)	0.000

Geometric parameters (Å, º)

S1—C2	1.706 (3)	C2—H2	0.9300
S1—C1	1.731 (3)	C3—C4	1.521 (4)
S2—C1	1.742 (3)	C3—H3A	0.9700
S2—C3	1.816 (3)	C3—H3B	0.9700
N1—C1	1.307 (4)	C4—C4^i	1.532 (6)
N1—N2	1.377 (4)	C4—H4A	0.9700
N2—C2	1.298 (5)	C4—H4B	0.9700
C2—S1—C1	86.31 (15)	C4—C3—H3A	109.8
C1—S2—C3	100.60 (14)	S2—C3—H3A	109.8
C1—N1—N2	111.9 (3)	C4—C3—H3B	109.8
C2—N2—N1	112.0 (3)	S2—C3—H3B	109.8
N1—C1—S1	114.3 (2)	H3A—C3—H3B	108.3
N1—C1—S2	122.3 (2)	C3—C4—C4^i	111.0 (3)
S1—C1—S2	123.42 (17)	C3—C4—H4A	109.4
N2—C2—S1	115.5 (3)	C4^i—C4—H4A	109.4
N2—C2—H2	122.3	C3—C4—H4B	109.4
S1—C2—H2	122.3	C4^i—C4—H4B	109.4
C4—C3—S2	109.2 (2)	H4A—C4—H4B	108.0
C1—N1—N2—C2	0.0	C3—S2—C1—S1	0.0
N2—N1—C1—S1	0.0	N1—N2—C2—S1	0.0
N2—N1—C1—S2	180.0	C1—S1—C2—N2	0.0
C2—S1—C1—N1	0.0	C1—S2—C3—C4	180.0
C2—S1—C1—S2	180.0	S2—C3—C4—C4^i	180.0
C3—S2—C1—N1	180.0

Symmetry code: (i) −x+1, −y, −z+2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2^ii	0.93	2.58	3.333 (7)	139

Symmetry code: (ii) −x, y, −z+1.