1,2-Bis(2-thia­zolin-2-ylsulfan­yl)ethane

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.

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

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Computing details

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

Crystal data

C8H12N2S4	F(000) = 276
Mr = 264.44	Dx = 1.484 Mg m^−3
Monoclinic, P21/c	Melting point: 398 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 5.8169 (13) Å	Cell parameters from 1530 reflections
b = 10.001 (2) Å	θ = 2.9–26.3°
c = 10.216 (2) Å	µ = 0.77 mm^−1
β = 95.187 (4)°	T = 293 K
V = 591.9 (2) Å^3	Block, colourless
Z = 2	0.24 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD area-detector diffractometer	1038 independent reflections
Radiation source: fine-focus sealed tube	856 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.029
φ and ω scans	θmax = 25.0°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.769, Tmax = 1.000	k = −11→11
2909 measured reflections	l = −12→7

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0429P)^2 + 0.2261P] where P = (Fo^2 + 2Fc^2)/3
1038 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 0.25 e Å^−3
0 restraints	Δρmin = −0.26 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S2	0.52475 (11)	−0.05810 (7)	0.29258 (6)	0.0501 (2)
S1	0.73838 (12)	0.09905 (7)	0.08706 (6)	0.0568 (2)
N1	0.8635 (3)	0.1234 (2)	0.33908 (17)	0.0472 (5)
C1	0.9947 (5)	0.1979 (3)	0.1288 (2)	0.0601 (7)
H1A	1.1311	0.1503	0.1064	0.072*
H1B	0.9854	0.2822	0.0817	0.072*
C2	1.0046 (4)	0.2215 (3)	0.2758 (2)	0.0530 (6)
H2A	1.1634	0.2152	0.3134	0.064*
H2B	0.9494	0.3109	0.2923	0.064*
C3	0.7280 (4)	0.0627 (2)	0.2561 (2)	0.0385 (5)
C4	0.5637 (4)	−0.0574 (2)	0.4712 (2)	0.0445 (6)
H4A	0.5081	−0.1412	0.5042	0.053*
H4B	0.7270	−0.0503	0.4996	0.053*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S2	0.0527 (4)	0.0570 (4)	0.0418 (4)	−0.0116 (3)	0.0108 (3)	−0.0059 (3)
S1	0.0703 (5)	0.0692 (5)	0.0304 (4)	−0.0106 (3)	0.0023 (3)	0.0036 (3)
N1	0.0508 (12)	0.0579 (13)	0.0334 (10)	−0.0102 (9)	0.0056 (9)	0.0051 (9)
C1	0.0603 (16)	0.0763 (19)	0.0445 (14)	−0.0140 (13)	0.0092 (12)	0.0119 (12)
C2	0.0554 (15)	0.0593 (16)	0.0442 (14)	−0.0110 (12)	0.0037 (11)	0.0105 (11)
C3	0.0402 (12)	0.0438 (12)	0.0324 (11)	0.0058 (9)	0.0077 (9)	0.0017 (9)
C4	0.0486 (13)	0.0438 (13)	0.0422 (13)	−0.0010 (10)	0.0113 (10)	0.0065 (10)

Geometric parameters (Å, º)

S2—C3	1.753 (2)	C1—H1A	0.9700
S2—C4	1.819 (2)	C1—H1B	0.9700
S1—C3	1.771 (2)	C2—H2A	0.9700
S1—C1	1.807 (3)	C2—H2B	0.9700
N1—C3	1.260 (3)	C4—C4^i	1.514 (4)
N1—C2	1.467 (3)	C4—H4A	0.9700
C1—C2	1.516 (3)	C4—H4B	0.9700
C3—S2—C4	100.68 (11)	N1—C2—H2B	109.4
C3—S1—C1	89.01 (11)	C1—C2—H2B	109.4
C3—N1—C2	111.51 (19)	H2A—C2—H2B	108.0
C2—C1—S1	105.99 (16)	N1—C3—S2	125.56 (17)
C2—C1—H1A	110.5	N1—C3—S1	118.85 (17)
S1—C1—H1A	110.5	S2—C3—S1	115.59 (12)
C2—C1—H1B	110.5	C4^i—C4—S2	111.8 (2)
S1—C1—H1B	110.5	C4^i—C4—H4A	109.2
H1A—C1—H1B	108.7	S2—C4—H4A	109.2
N1—C2—C1	111.1 (2)	C4^i—C4—H4B	109.2
N1—C2—H2A	109.4	S2—C4—H4B	109.2
C1—C2—H2A	109.4	H4A—C4—H4B	107.9
C3—S1—C1—C2	−15.2 (2)	C4—S2—C3—N1	2.7 (2)
C3—N1—C2—C1	−14.9 (3)	C4—S2—C3—S1	−177.43 (12)
S1—C1—C2—N1	19.8 (3)	C1—S1—C3—N1	8.4 (2)
C2—N1—C3—S2	−177.80 (17)	C1—S1—C3—S2	−171.42 (15)
C2—N1—C3—S1	2.4 (3)	C3—S2—C4—C4^i	80.8 (2)

Symmetry code: (i) −x+1, −y, −z+1.