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The title compound, C8H12N2S4, was synthesized by the reaction of 1,2-dibromo­ethane and thia­zoline-2-thione. The mol­ecule contains a centre of inversion at the mid-point of the central C-C bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806026808/bt2132sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806026808/bt2132Isup2.hkl
Contains datablock I

CCDC reference: 618133

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.031
  • wR factor = 0.086
  • Data-to-parameter ratio = 16.2

checkCIF/PLATON results

No syntax errors found



Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.769 1.000 Tmin(prime) and Tmax expected: 0.828 0.885 RR(prime) = 0.821 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.82 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.88 PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature . 293 K PLAT322_ALERT_2_C Check Hybridisation of S1 in Main Residue . ?
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.885 Tmax scaled 0.885 Tmin scaled 0.680
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

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

1,2-Bis(2-thiazolin-2-ylsulfanyl)ethane top
Crystal data top
C8H12N2S4F(000) = 276
Mr = 264.44Dx = 1.484 Mg m3
Monoclinic, P21/cMelting point: 398 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 5.8169 (13) ÅCell parameters from 1530 reflections
b = 10.001 (2) Åθ = 2.9–26.3°
c = 10.216 (2) ŵ = 0.77 mm1
β = 95.187 (4)°T = 293 K
V = 591.9 (2) Å3Block, colourless
Z = 20.24 × 0.20 × 0.16 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
1038 independent reflections
Radiation source: fine-focus sealed tube856 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.029
φ and ω scansθmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 66
Tmin = 0.769, Tmax = 1.000k = 1111
2909 measured reflectionsl = 127
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)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.086H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.2261P]
where P = (Fo2 + 2Fc2)/3
1038 reflections(Δ/σ)max < 0.001
64 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.26 e Å3
Special details top

Experimental. IR (KBr, ν cm-1): 2984, 2952, 2846, 1567, 1450, 1400, 1304, 1254, 1196, 1013, 997, 919, 691; 1H NMR (CDCl3): 3.41 (t, 4H), 3.44 (t, 4H), 4.22 (t, 4H).

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*/Ueq
S20.52475 (11)0.05810 (7)0.29258 (6)0.0501 (2)
S10.73838 (12)0.09905 (7)0.08706 (6)0.0568 (2)
N10.8635 (3)0.1234 (2)0.33908 (17)0.0472 (5)
C10.9947 (5)0.1979 (3)0.1288 (2)0.0601 (7)
H1A1.13110.15030.10640.072*
H1B0.98540.28220.08170.072*
C21.0046 (4)0.2215 (3)0.2758 (2)0.0530 (6)
H2A1.16340.21520.31340.064*
H2B0.94940.31090.29230.064*
C30.7280 (4)0.0627 (2)0.2561 (2)0.0385 (5)
C40.5637 (4)0.0574 (2)0.4712 (2)0.0445 (6)
H4A0.50810.14120.50420.053*
H4B0.72700.05030.49960.053*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S20.0527 (4)0.0570 (4)0.0418 (4)0.0116 (3)0.0108 (3)0.0059 (3)
S10.0703 (5)0.0692 (5)0.0304 (4)0.0106 (3)0.0023 (3)0.0036 (3)
N10.0508 (12)0.0579 (13)0.0334 (10)0.0102 (9)0.0056 (9)0.0051 (9)
C10.0603 (16)0.0763 (19)0.0445 (14)0.0140 (13)0.0092 (12)0.0119 (12)
C20.0554 (15)0.0593 (16)0.0442 (14)0.0110 (12)0.0037 (11)0.0105 (11)
C30.0402 (12)0.0438 (12)0.0324 (11)0.0058 (9)0.0077 (9)0.0017 (9)
C40.0486 (13)0.0438 (13)0.0422 (13)0.0010 (10)0.0113 (10)0.0065 (10)
Geometric parameters (Å, º) top
S2—C31.753 (2)C1—H1A0.9700
S2—C41.819 (2)C1—H1B0.9700
S1—C31.771 (2)C2—H2A0.9700
S1—C11.807 (3)C2—H2B0.9700
N1—C31.260 (3)C4—C4i1.514 (4)
N1—C21.467 (3)C4—H4A0.9700
C1—C21.516 (3)C4—H4B0.9700
C3—S2—C4100.68 (11)N1—C2—H2B109.4
C3—S1—C189.01 (11)C1—C2—H2B109.4
C3—N1—C2111.51 (19)H2A—C2—H2B108.0
C2—C1—S1105.99 (16)N1—C3—S2125.56 (17)
C2—C1—H1A110.5N1—C3—S1118.85 (17)
S1—C1—H1A110.5S2—C3—S1115.59 (12)
C2—C1—H1B110.5C4i—C4—S2111.8 (2)
S1—C1—H1B110.5C4i—C4—H4A109.2
H1A—C1—H1B108.7S2—C4—H4A109.2
N1—C2—C1111.1 (2)C4i—C4—H4B109.2
N1—C2—H2A109.4S2—C4—H4B109.2
C1—C2—H2A109.4H4A—C4—H4B107.9
C3—S1—C1—C215.2 (2)C4—S2—C3—N12.7 (2)
C3—N1—C2—C114.9 (3)C4—S2—C3—S1177.43 (12)
S1—C1—C2—N119.8 (3)C1—S1—C3—N18.4 (2)
C2—N1—C3—S2177.80 (17)C1—S1—C3—S2171.42 (15)
C2—N1—C3—S12.4 (3)C3—S2—C4—C4i80.8 (2)
Symmetry code: (i) x+1, y, z+1.
 

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