1,2,4,6-Tetra­thia­cyclo­hepta­ne

The title compound, C₃H₆S₄, is a cyclic polysulfane containing one disulfane S₂ group and two single S atoms bridged by three CH₂ groups, thus forming a seven-membered ring. The ring exhibits a chair conformation.

Key indicators

• Single-crystal X-ray study
• T = 294 K
• Mean [sigma](S-C)= 0.004 Å
• R factor = 0.066
• wR factor = 0.138
• Data-to-parameter ratio = 31.5

checkCIF/PLATON results

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 1996); software used to prepare material for publication: SHELXL97.

1,2,4,6-tetrathiacycloheptane

Crystal data

C3H6S4	F(000) = 352
Mr = 170.32	Dx = 1.711 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3865 reflections
a = 11.1285 (4) Å	θ = 2.5–30.0°
b = 5.2653 (2) Å	µ = 1.31 mm^−1
c = 11.7399 (4) Å	T = 294 K
β = 105.963 (1)°	Prism, colorless
V = 661.37 (4) Å^3	0.20 × 0.18 × 0.15 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	1622 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.090
Graphite monochromator	θmax = 30.6°, θmin = 2.2°
ω scans	h = −12→15
5831 measured reflections	k = −7→7
2018 independent reflections	l = −16→11

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.46	w = 1/[σ^2(Fo^2) + (0.0288P)^2 + 0.65P] where P = (Fo^2 + 2Fc^2)/3
2018 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 0.61 e Å^−3
0 restraints	Δρmin = −0.64 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
S1	0.6479 (1)	0.7137 (2)	0.39086 (9)	0.0381 (3)
S2	0.66833 (9)	0.3404 (2)	0.35810 (8)	0.0317 (2)
S3	0.90117 (9)	0.2125 (2)	0.56458 (9)	0.0350 (2)
S4	0.69318 (9)	0.4823 (2)	0.64219 (8)	0.0323 (2)
C1	0.8373 (4)	0.2947 (7)	0.4111 (3)	0.0335 (8)
H1A	0.8603	0.1622	0.3636	0.040*
H1B	0.8774	0.4500	0.3962	0.040*
C2	0.8564 (3)	0.4824 (7)	0.6402 (3)	0.0318 (8)
H2A	0.8727	0.6370	0.6021	0.038*
H2B	0.9088	0.4851	0.7213	0.038*
C3	0.6301 (4)	0.7360 (7)	0.5409 (4)	0.0341 (8)
H3A	0.6688	0.8932	0.5757	0.041*
H3B	0.5415	0.7492	0.5345	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0499 (6)	0.0299 (5)	0.0349 (5)	0.0059 (4)	0.0122 (4)	0.0066 (4)
S2	0.0335 (5)	0.0315 (4)	0.0276 (4)	−0.0035 (4)	0.0043 (3)	−0.0041 (3)
S3	0.0314 (5)	0.0320 (5)	0.0387 (5)	0.0045 (4)	0.0047 (4)	0.0004 (4)
S4	0.0353 (5)	0.0351 (5)	0.0282 (4)	−0.0031 (4)	0.0116 (4)	−0.0010 (4)
C1	0.034 (2)	0.037 (2)	0.034 (2)	−0.001 (2)	0.015 (2)	−0.003 (2)
C2	0.027 (2)	0.033 (2)	0.032 (2)	−0.006 (1)	0.004 (1)	−0.005 (2)
C3	0.035 (2)	0.028 (2)	0.041 (2)	0.000 (1)	0.014 (2)	−0.005 (2)

Geometric parameters (Å, º)

S3—C1	1.798 (4)	C1—H1A	0.9700
S3—C2	1.816 (4)	C1—H1B	0.9700
S2—C1	1.827 (4)	C3—H3A	0.9700
S2—S1	2.028 (1)	C3—H3B	0.9700
S4—C3	1.798 (4)	C2—H2A	0.9700
S4—C2	1.823 (4)	C2—H2B	0.9700
S1—C3	1.829 (4)
C1—S3—C2	102.5 (2)	S4—C3—H3A	107.9
C1—S2—S1	102.8 (1)	S1—C3—H3A	107.9
C3—S4—C2	101.6 (2)	S4—C3—H3B	107.9
C3—S1—S2	107.0 (1)	S1—C3—H3B	107.9
S3—C1—S2	117.3 (2)	H3A—C3—H3B	107.2
S3—C1—H1A	108.0	S3—C2—S4	114.5 (2)
S2—C1—H1A	108.0	S3—C2—H2A	108.6
S3—C1—H1B	108.0	S4—C2—H2A	108.6
S2—C1—H1B	108.0	S3—C2—H2B	108.6
H1A—C1—H1B	107.2	S4—C2—H2B	108.6
S4—C3—S1	117.6 (2)	H2A—C2—H2B	107.6
C1—S2—S1—C3	−89.4 (2)	S2—S1—C3—S4	24.1 (3)
C2—S3—C1—S2	−60.2 (3)	C1—S3—C2—S4	77.2 (2)
S1—S2—C1—S3	88.4 (2)	C3—S4—C2—S3	−108.6 (2)
C2—S4—C3—S1	56.6 (3)