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The title compound, C10H14N2S4, was synthesized by the reaction of the potassium salt of 2-thio­thia­zole and 1,4-di­bromo­butane. The two 2-thia­zole­thio groups are related by a center of symmetry. The plane defined by the butyl carbon chain is approximately orthogonal to the thia­zole plane, with a dihedral angle of 84.7 (8)°. Intermolecular S...S interactions between adjacent mol­ecules link them into infinite chains running along the c axis.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803015204/ww6095sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803015204/ww6095Isup2.hkl
Contains datablock I

CCDC reference: 221692

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.030
  • wR factor = 0.076
  • Data-to-parameter ratio = 18.1

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry








Computing details top

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

2,2'-[(1,4-Butanediyl)dithio]dithiazole top
Crystal data top
C10H12N2S4F(000) = 300
Mr = 288.46Dx = 1.459 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 754 reflections
a = 6.067 (2) Åθ = 3.0–25.9°
b = 14.099 (5) ŵ = 0.70 mm1
c = 7.733 (3) ÅT = 293 K
β = 97.101 (6)°Needle, colourless
V = 656.4 (4) Å30.56 × 0.32 × 0.20 mm
Z = 2
Data collection top
Bruker CCD area-detector
diffractometer
1336 independent reflections
Radiation source: fine-focus sealed tube1021 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
φ and ω scansθmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan
SADABS (Sheldrick, 1997)
h = 47
Tmin = 0.772, Tmax = 0.870k = 1717
3664 measured reflectionsl = 99
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.030 w = 1/[σ2(Fo2) + (0.0344P)2 + 0.1369P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.076(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.20 e Å3
1336 reflectionsΔρmin = 0.18 e Å3
74 parameters
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 > 2σ(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*/Ueq
S10.16147 (9)0.02272 (4)0.82924 (7)0.0476 (2)
S20.11393 (9)0.18759 (4)1.06770 (7)0.0509 (2)
N10.4513 (3)0.16970 (13)0.8982 (2)0.0495 (5)
C10.3181 (4)0.27241 (15)1.0963 (3)0.0513 (5)
H10.31680.32511.16860.062*
C20.4791 (4)0.25157 (16)0.9995 (3)0.0574 (6)
H20.60390.28990.99970.069*
C30.2654 (3)0.12949 (13)0.9224 (2)0.0371 (4)
C40.3962 (4)0.01837 (14)0.7242 (3)0.0445 (5)
H4A0.53230.00060.79600.053*
H4B0.39160.08710.71820.053*
C50.4029 (3)0.02053 (13)0.5416 (2)0.0388 (5)
H5A0.41640.08910.54700.047*
H5B0.26500.00520.46970.047*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0534 (3)0.0478 (3)0.0452 (3)0.0087 (2)0.0204 (2)0.0120 (2)
S20.0505 (4)0.0518 (3)0.0532 (4)0.0016 (3)0.0181 (3)0.0147 (2)
N10.0503 (11)0.0526 (11)0.0481 (10)0.0097 (9)0.0158 (9)0.0063 (8)
C10.0624 (14)0.0406 (11)0.0501 (12)0.0031 (11)0.0039 (11)0.0073 (10)
C20.0592 (14)0.0516 (13)0.0623 (14)0.0172 (11)0.0114 (12)0.0056 (11)
C30.0436 (11)0.0385 (10)0.0301 (9)0.0043 (9)0.0085 (8)0.0001 (8)
C40.0577 (13)0.0414 (11)0.0364 (10)0.0088 (10)0.0140 (9)0.0022 (9)
C50.0459 (11)0.0388 (11)0.0322 (9)0.0056 (9)0.0062 (9)0.0019 (8)
Geometric parameters (Å, º) top
S1—C31.752 (2)C2—H20.9300
S1—C41.819 (2)C4—C51.520 (3)
S2—C11.717 (2)C4—H4A0.9700
S2—C31.7413 (18)C4—H4B0.9700
N1—C31.297 (3)C5—C5i1.524 (4)
N1—C21.394 (3)C5—H5A0.9700
C1—C21.335 (3)C5—H5B0.9700
C1—H10.9300
C3—S1—C4101.28 (10)C5—C4—S1114.36 (14)
C1—S2—C388.91 (10)C5—C4—H4A108.7
C3—N1—C2109.12 (17)S1—C4—H4A108.7
C2—C1—S2109.93 (17)C5—C4—H4B108.7
C2—C1—H1125.0S1—C4—H4B108.7
S2—C1—H1125.0H4A—C4—H4B107.6
C1—C2—N1116.9 (2)C4—C5—C5i111.5 (2)
C1—C2—H2121.6C4—C5—H5A109.3
N1—C2—H2121.6C5i—C5—H5A109.3
N1—C3—S2115.19 (15)C4—C5—H5B109.3
N1—C3—S1126.24 (14)C5i—C5—H5B109.3
S2—C3—S1118.54 (11)H5A—C5—H5B108.0
C3—S2—C1—C20.33 (18)C1—S2—C3—S1178.20 (13)
S2—C1—C2—N10.4 (3)C4—S1—C3—N17.6 (2)
C3—N1—C2—C10.3 (3)C4—S1—C3—S2170.23 (11)
C2—N1—C3—S20.0 (2)C3—S1—C4—C586.26 (16)
C2—N1—C3—S1177.82 (16)S1—C4—C5—C5i177.24 (18)
C1—S2—C3—N10.17 (17)
Symmetry code: (i) x+1, y, z+1.
 

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