Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806039602/sj2129sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806039602/sj2129Isup2.hkl
Contains datablock I

CCDC reference: 628398

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

Computing details top

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) top
Crystal data top
C8H10N4S4F(000) = 300
Mr = 290.44Dx = 1.568 Mg m3
Monoclinic, C2/mMelting point: 94 K
Hall symbol: -C 2yMo Kα radiation, λ = 0.71073 Å
a = 17.333 (3) ÅCell parameters from 1643 reflections
b = 6.9652 (14) Åθ = 2.5–28.3°
c = 5.355 (1) ŵ = 0.75 mm1
β = 107.926 (3)°T = 291 K
V = 615.1 (2) Å3Plate, colourless
Z = 20.37 × 0.22 × 0.07 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
631 independent reflections
Radiation source: fine-focus sealed tube628 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.010
φ and ω scansθmax = 25.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick,1996)
h = 2019
Tmin = 0.768, Tmax = 0.949k = 84
1629 measured reflectionsl = 66
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.087H-atom parameters constrained
S = 1.10 w = 1/[σ2(Fo2) + (0.0425P)2 + 1.2117P]
where P = (Fo2 + 2Fc2)/3
631 reflections(Δ/σ)max < 0.001
49 parametersΔρmax = 0.46 e Å3
0 restraintsΔρmin = 0.25 e Å3
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
S10.20691 (5)0.00000.83005 (15)0.0359 (3)
S20.32221 (4)0.00000.49775 (15)0.0357 (3)
N10.15985 (16)0.00000.3272 (5)0.0387 (7)
N20.09044 (17)0.00000.4008 (6)0.0447 (7)
C10.22525 (18)0.00000.5301 (6)0.0306 (6)
C20.1064 (2)0.00000.6542 (7)0.0397 (8)
H20.06580.00000.73430.048*
C30.38371 (18)0.00000.8403 (6)0.0361 (7)
H3A0.37160.11290.92750.043*0.50
H3B0.37160.11290.92750.043*0.50
C40.47288 (18)0.00000.8568 (6)0.0394 (8)
H4A0.48460.11270.76830.047*0.50
H4B0.48460.11270.76830.047*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0294 (4)0.0502 (5)0.0264 (4)0.0000.0064 (3)0.000
S20.0252 (4)0.0526 (5)0.0279 (4)0.0000.0062 (3)0.000
N10.0259 (13)0.0574 (18)0.0301 (14)0.0000.0047 (10)0.000
N20.0257 (13)0.064 (2)0.0409 (16)0.0000.0051 (11)0.000
C10.0288 (15)0.0354 (15)0.0253 (14)0.0000.0052 (11)0.000
C20.0293 (15)0.056 (2)0.0345 (17)0.0000.0102 (13)0.000
C30.0255 (15)0.055 (2)0.0244 (14)0.0000.0036 (11)0.000
C40.0281 (16)0.055 (2)0.0314 (18)0.0000.0043 (14)0.000
Geometric parameters (Å, º) top
S1—C21.706 (3)C2—H20.9300
S1—C11.731 (3)C3—C41.521 (4)
S2—C11.742 (3)C3—H3A0.9700
S2—C31.816 (3)C3—H3B0.9700
N1—C11.307 (4)C4—C4i1.532 (6)
N1—N21.377 (4)C4—H4A0.9700
N2—C21.298 (5)C4—H4B0.9700
C2—S1—C186.31 (15)C4—C3—H3A109.8
C1—S2—C3100.60 (14)S2—C3—H3A109.8
C1—N1—N2111.9 (3)C4—C3—H3B109.8
C2—N2—N1112.0 (3)S2—C3—H3B109.8
N1—C1—S1114.3 (2)H3A—C3—H3B108.3
N1—C1—S2122.3 (2)C3—C4—C4i111.0 (3)
S1—C1—S2123.42 (17)C3—C4—H4A109.4
N2—C2—S1115.5 (3)C4i—C4—H4A109.4
N2—C2—H2122.3C3—C4—H4B109.4
S1—C2—H2122.3C4i—C4—H4B109.4
C4—C3—S2109.2 (2)H4A—C4—H4B108.0
C1—N1—N2—C20.0C3—S2—C1—S10.0
N2—N1—C1—S10.0N1—N2—C2—S10.0
N2—N1—C1—S2180.0C1—S1—C2—N20.0
C2—S1—C1—N10.0C1—S2—C3—C4180.0
C2—S1—C1—S2180.0S2—C3—C4—C4i180.0
C3—S2—C1—N1180.0
Symmetry code: (i) x+1, y, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···N2ii0.932.583.333 (7)139
Symmetry code: (ii) x, y, z+1.
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds