Four bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)oligosulfanes

The four oligosulfanes, bis(1-chloro-2,2,4,4-tetra­methyl-3-oxo­cyclo­butan-1-yl)­disulfane, C₁₆H₂₄Cl₂O₂S₂, (III), 1,3-bis(1-chloro-2,2,4,4-tetra­methyl-3-oxo­cyclo­butan-1-yl)­trisulfane, C₁₆H₂₄Cl₂O₂S₃, (V), 1,4-bis(1-chloro-2,2,4,4-tetra­methyl-3-oxo­cyclo­butan-1-yl)­tetrasulfane, C₁₆H₂₄Cl₂O₂S₄, (VII), and 1,6-bis(1-chloro-2,2,4,4-tetra­methyl-3-oxo­cyclo­butan-1-yl)­hexasul­fane, C₁₆H₂₄Cl₂O₂S₆, (VIII), all have similar geometric parameters, with the C-C bond lengths involving the chloro-substituted cyclo­butanyl C atom being elongated to about 1.59 Å. There are two mol­ecules in the asymmetric units of the tri- and tetrasulfanes, and the mol­ecules in the latter compound have local C₂ symmetry. The mol­ecule of the hexasulfane has crystallographic C₂ symmetry. Most of the cyclo­butanyl rings are not perfectly planar and have slight but varying degrees of distortion towards a flattened tetrahedron. The polysulfane chain in each structure has a helical conformation, with each additional S atom in the chain adding approximately one quarter of a turn to the helix.

S1. Comment

Although there are some classical methods for the synthesis of organic polysulfanes (Gunderman & Hümke, 1985; Steudel & Kustos, 1994), they often result in mixtures of homologous compounds which are difficult to separate. Therefore, in recent years, new protocols for the selective preparation of linear and cyclic polysulfanes have been elaborated (Steudel, Pridöhl et al., 1995; Steudel, Westphal & Pickardt, 1995, and references therein). For example, titanocene pentasulfane has been shown to be a very useful sulfur-transfer reagent. It reacts with chloroalkanes to give dialkylpentasulfanes, and with alkylsulfenyl chlorides to give dialkylheptasulfanes (Steudel & Kustos, 1991; Westphal & Steudel, 1991; Kustos et al., 1993). On the other hand, several reactions of thioketones have been described in which polysulfur compounds are formed in the absence of a sulfur-transfer reagent, for example the formation of 1,2,4-trithiolanes on treatment with organic azides (Mloston & Heimgartner, 1995; Mloston et al., 1995, 1996). In this case, an intermediate thiaziridine is believed to be responsible for the sulfur transfer, which leads to reactive thiocarbonyl S-sulfides. Similar sulfur-transfer reactions occur under mild conditions between thiiranes and thioketones (e.g. Huisgen & Rapp, 1997; Huisgen et al., 1997), whereas the formation of reactive thiocarbonyl S-sulfides from thioketones and S₈ needs higher temperatures (e.g. Saito, Nagashima et al., 1992; Saito, Shundo et al., 1992; Okuma et al., 1993) or the presence of sodium benzenethiolate as a catalyst (Huisgen et al., 1997). In the case of adamantanethione, the corresponding 1,2,4-trithiolane was formed on treatment with silica gel in dichloromethane (Linden et al., 2002).

As the intermediacy of thiocarbonyl S-sulfides and their isomeric dithiiranes has frequently been proposed to explain the formation of polysulfur heterocycles (Mloston & Heimgartner, 1995; Huisgen et al., 1997; El-Essawy et al., 1998; Fabian & Senning, 1998; Hegab et al., 1999; Hawata et al., 2000), many attempts have been undertaken to synthesize those compounds. Within the last few years, several stable dithiiranes have been prepared (Ishii et al., 1994; Ishii & Nakayama, 1999, 2000; Shimada et al., 1999), and the parent compound has been generated photolytically and isolated in a matrix at 10 K (Mloston et al., 2001).

Recently, we reported the synthesis of α-chlorosulfenyl chloride (II) from thioketone (I) by using either chlorine (Koch et al., 1999), or phosphorus pentachloride or sulfuryl chloride (Mloston et al., 2002), as the chlorinating agent (see Scheme). The reaction of (II) with thioketone (I) in dichloromethane at 298 K gave the disulfane, (III). Treatment of (I) with sulfur dichloride in tetrachloromethane at 298 K led to a 1:1 mixture of α-chlorodisulfanyl chloride (IV) and the trisulfane, (V), which was separated by trituration with petroleum ether. The latter was formed in high yield when purified (IV) was reacted with (I) in dichloromethane. The tetrasulfane, (VII), has been obtained from the reaction of (I) and disulfur dichloride in dichloromethane at 298 K, with α-chlorotrisulfanyl chloride (VI) being a likely intermediate. Unexpectedly, the reaction of (II) with tetrabutylammonium hexasulfane in tetrahydrofuran gave the symmetrical hexasulfane, (VIII), as colourless crystals in low yield. As part of their full characterization, low-temperature X-ray crystal-structure determinations of the compounds (III), (V), (VII) and (VIII) were carried out and the results are presented here. \sch

The molecules of compounds (III) and (V) do not possess any local or crystallographic symmetry (Figs. 1 and 2). The asymmetric units in compounds (V) and (VII) each contain two molecules which have very similar conformations and can be superimposed very closely; the r.m.s. fit between the non-H atoms of the symmetry-independent molecules is 0.59 Å for (V) and 0.23 Å for (VII). Both symmetry-independent molecules of (VII) display local C₂ symmetry about an axis passing through the middle of the central S—S bond, with the r.m.s. deviations of the C₂-related atoms being 0.08 and 0.11 Å for molecules A and B, respectively (Fig. 3). The molecule of (VIII) has crystallographic C₂ symmetry about an axis passing through the middle of the central S—S bond (Fig. 4).

The pattern of bond lengths and angles is consistent across all four structures and these parameters have normal values (Tables 1–4), although the S1—C1 bond in (III) is about 0.03 Å longer than any of the other S—C bonds in these structures [mean value 1.816 (2)°], including the chemically equivalent S2—C9 bond in (III). The C—C bond lengths involving the chloro-substituted cyclobutanyl C atom are longer than normal C—C single bonds, in the range 1.585 (2)–1.601 (2) Å. However, they are consistent with those previously found in a similar environment (Mloston et al., 1999). This is evidently due to the electron-withdrawing properties of the S and Cl substituents. As a result, the cyclobutanyl rings are not perfect squares. While the C—C—C bond angle at the chloro-substituted C atom is always close to 90°, that at the oxo-substituted C atom is consistently about 96°, while those at the dimethyl-substituted C atoms hover around 86°.

With the exception of one planar ring in compound (VII), the cyclobutanyl rings in the four structures are not planar, but are slightly distorted towards a flattened tetrahedron. The magnitudes of the folds about the ring diagonals vary from structure to structure and from one end of a molecule to the next, with some rings being much flatter than others, as indicated in Table 5. The direction of the fold also varies from one ring to the next and is not necessarily the same for all rings in any one particular structure. The Cl substituent on the ring can be described as being in a pseudo-axial (ax) or a pseudo-equatorial (eq) position, depending on whether the fold about the (Me₂)C···C(Me₂) axis places the Cl atom above the concave or convex side, respectively, of the ring. The ax/eq assignments for each structure are also listed in Table 5.

The polysulfane chain in each structure always has a helical conformation. The magnitudes of the torsion angles about the S—S bonds are fairly constant and lie between 83 and 101°, while, in any one structure, successive torsion angles along the chain have the same sign. Thus, compounds (III), (V), (VII), and (VIII) display approximately 1/4, 1/2, 3/4, and 1.25 full turns, respectively. The one structure missing in this series is the pentasulfane, which should display one complete turn. We have actually determined the structure of this latter compound and it does display the expected full-turn conformation. However, unexpected geometrical and crystallographic anomalies in this structure determination require further investigation and the structure of the pentasulfane will be published at a later date. An analysis of the Cambridge Structural Database (April 2002 release; Allen & Kennard, 1993) indicates that a helical conformation of this type, with torsion angles about the S—S bond in the range 70–110°, is quite normal for polysulfane chains.

Table 5. A ngles (°) between the planes on each side of the diagonals of the cyclobutanyl rings.

S2. Experimental

The syntheses of (III), (V) and (VII) have been reported by Mloston et al. (2000), and single crystals of each compound were obtained by slow evaporation from their respective solutions in hexane/dichloromethane. For the preparation of (VIII), tetrabutylammonium hexasulfane (745 mg, 1.1 mmol) was added to a stirred solution of (II) (257 mg, 1.1 mmol) in tetrahydrofuran (5 ml) at 233 K. After stirring for 2 h at 233 K and for 24 h at 298 K, the solvent was evaporated and the residue dissolved in dichloromethane and filtered through silica gel. Evaporation of the solvent and recrystallization of the residue yielded 30 mg (10%) of (VIII) as colourless crystals (m.p. 402–404 K). The spectroscopic data for (III), (V) and (VII) have been reported by Mloston et al. (2002), and the corresponding data for (VIII) (see below) are virtually identical. These compounds cannot be distinguished by mass spectrometry, as they produce similar fragmentation patterns and the molecular ion does not appear in the spectra. Spectroscopic data for (VIII): ¹H NMR (CDCl₃, δ, p.p.m.): 1.38 (s, 4 Me), 1.41 (s, 4 Me); ¹³C NMR (CDCl₃, δ, p.p.m.): 22.7 (q, 4 Me), 23.4 (q, 4 Me), 69.2 (s, C2, C2', C4, C4'), 87.4 (s, C1, C1'), 215.4 (s, 2 C═O); IR (KBr, ν, cm^-1): 1790 (versus, C═O), 1770 (s, C═O), 1461 (s), 1455 (s), 1443 (s), 1380 (s), 1365 (s), 1169 (s), 1134 (s), 1029 (s), 912 (s), 887 (s), 832 (s).

S3. Refinement

For each structure, the methyl H atoms were constrained to an ideal geometry (C—H = 0.96–0.98 Å), with U_iso(H) = 1.5U_eq(C), but they were allowed to rotate freely about the C—C bonds. For (III), (V) and (VII), three, five and three low-angle reflections, respectively, were omitted from the final refinement because their observed intensities were much lower than the calculated values, as a result of being partially obscured by the beam stop. The structures of (V) and (VII) have two molecules in the asymmetric unit. In each case, the possibility of the two molecules being related by additional symmetry was excluded by comparing their atomic coordinates using PLATON (Spek, 2002). Attempts to collect the data for (VII) at 160 K were unsuccessful, because the thermal shock of cooling destroyed the crystals, so the analysis for this compound was conducted at 253 K. For (VIII), even though the molecule is achiral, the compound crystallized in a polar space group. Refinement of the absolute structure parameter (Flack, 1983) yielded a value of 0.39 (13), which suggests that the crystal may be a merohedral twin, although the large standard uncertainty on this parameter means that a definitive conclusion regarding the absolute structure cannot be drawn (Flack & Bernardinelli, 2000). The absolute structure defined by the model and space group, P4₁2₁2, used in the refinement has therefore been assigned arbitrarily. The inverted structure and space group, P4₃2₁2, could be used equally well.

Computing details

For all compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2002).

Figures

	Fig. 1. A view of the molecule of (III) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A view of one of the symmetry-independent molecules of (V) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 3. A view of one of the symmetry-independent molecules of (VII) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
	Fig. 4. A view of the molecule of (VIII) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii [symmetry code: (i) y - 1, 1 + x, -z.]

(III) bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)disulfane

Crystal data

C16H24Cl2O2S2	F(000) = 808
Mr = 383.39	Dx = 1.377 Mg m^−3
Monoclinic, P21/n	Melting point = 371–373 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.7379 (1) Å	Cell parameters from 103426 reflections
b = 26.7454 (4) Å	θ = 2.0–30.0°
c = 10.6473 (2) Å	µ = 0.58 mm^−1
β = 105.4292 (6)°	T = 160 K
V = 1849.58 (5) Å^3	Rod, colourless
Z = 4	0.32 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer	5400 independent reflections
Radiation source: Nonius FR591 sealed tube generator	3839 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.069
Detector resolution: 9 pixels mm^-1	θmax = 30.0°, θmin = 3.0°
ϕ and ω scans with κ offsets	h = −9→9
Absorption correction: numerical (Coppens et al., 1965)	k = −37→37
Tmin = 0.872, Tmax = 0.961	l = −14→14
40268 measured reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.093	H-atom parameters constrained
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0392P)^2 + 0.5066P] where P = (Fo^2 + 2Fc^2)/3
5397 reflections	(Δ/σ)max = 0.001
207 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.35 e Å^−3

Special details

Experimental. Solvent used: hexane/dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.847 (1) Frames collected: 1481 Seconds exposure per frame: 12 Degrees rotation per frame: 0.6 Crystal-Detector distance (mm): 41.0

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
Cl1	1.10057 (7)	0.069552 (19)	0.59120 (4)	0.03346 (12)
Cl2	0.78806 (6)	0.192378 (16)	0.41231 (4)	0.02775 (11)
S1	0.64412 (6)	0.072255 (16)	0.52548 (4)	0.02409 (10)
S2	0.69317 (7)	0.086746 (16)	0.34955 (4)	0.02372 (10)
O1	1.0234 (2)	0.09743 (5)	0.97583 (12)	0.0380 (3)
O2	0.2449 (2)	0.21167 (5)	0.09187 (13)	0.0371 (3)
C1	0.8859 (2)	0.08087 (6)	0.65477 (15)	0.0218 (3)
C2	0.8876 (3)	0.04590 (6)	0.77643 (16)	0.0241 (4)
C3	0.9560 (3)	0.09207 (7)	0.86002 (16)	0.0254 (4)
C4	0.9163 (3)	0.12886 (7)	0.74607 (16)	0.0256 (4)
C5	1.0378 (3)	0.00234 (7)	0.80294 (19)	0.0363 (4)
H51	1.1782	0.0149	0.8150	0.054*
H52	1.0038	−0.0208	0.7290	0.054*
H53	1.0282	−0.0152	0.8820	0.054*
C6	0.6747 (3)	0.02806 (7)	0.78537 (18)	0.0320 (4)
H61	0.6266	0.0009	0.7229	0.048*
H62	0.5770	0.0560	0.7652	0.048*
H63	0.6849	0.0160	0.8737	0.048*
C7	1.0954 (3)	0.16412 (8)	0.74896 (19)	0.0377 (5)
H71	1.1140	0.1870	0.8231	0.057*
H72	1.0659	0.1834	0.6678	0.057*
H73	1.2215	0.1446	0.7578	0.057*
C8	0.7192 (3)	0.15920 (7)	0.73639 (18)	0.0333 (4)
H81	0.7369	0.1798	0.8146	0.050*
H82	0.6030	0.1363	0.7291	0.050*
H83	0.6919	0.1808	0.6593	0.050*
C9	0.6083 (2)	0.15057 (6)	0.30954 (15)	0.0213 (3)
C10	0.5727 (3)	0.16323 (6)	0.15825 (16)	0.0245 (4)
C11	0.3665 (3)	0.18532 (6)	0.16538 (17)	0.0251 (4)
C12	0.3766 (2)	0.16529 (6)	0.30114 (16)	0.0227 (3)
C13	0.7134 (3)	0.20109 (7)	0.11823 (19)	0.0341 (4)
H131	0.6476	0.2134	0.0303	0.051*
H132	0.8445	0.1851	0.1191	0.051*
H133	0.7385	0.2292	0.1795	0.051*
C14	0.5470 (3)	0.11729 (7)	0.06844 (17)	0.0324 (4)
H141	0.4941	0.1279	−0.0224	0.049*
H142	0.4500	0.0938	0.0907	0.049*
H143	0.6807	0.1009	0.0798	0.049*
C15	0.3348 (3)	0.20333 (7)	0.39731 (19)	0.0317 (4)
H151	0.4348	0.2307	0.4082	0.047*
H152	0.3473	0.1871	0.4816	0.047*
H153	0.1953	0.2167	0.3641	0.047*
C16	0.2302 (3)	0.12054 (7)	0.29045 (17)	0.0273 (4)
H161	0.2555	0.1040	0.3754	0.041*
H162	0.2544	0.0968	0.2260	0.041*
H163	0.0874	0.1323	0.2632	0.041*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0254 (2)	0.0520 (3)	0.0250 (2)	0.00527 (19)	0.01036 (17)	0.0035 (2)
Cl2	0.0264 (2)	0.0298 (2)	0.0268 (2)	−0.00458 (17)	0.00671 (17)	−0.00365 (17)
S1	0.0246 (2)	0.0278 (2)	0.01853 (19)	−0.00379 (17)	0.00350 (16)	0.00245 (16)
S2	0.0299 (2)	0.0238 (2)	0.01701 (19)	0.00530 (17)	0.00555 (16)	−0.00017 (16)
O1	0.0497 (8)	0.0422 (8)	0.0185 (6)	−0.0082 (7)	0.0027 (6)	0.0005 (6)
O2	0.0336 (7)	0.0415 (8)	0.0357 (8)	0.0103 (6)	0.0081 (6)	0.0168 (6)
C1	0.0203 (8)	0.0269 (9)	0.0174 (7)	0.0011 (6)	0.0038 (6)	0.0015 (6)
C2	0.0283 (9)	0.0249 (9)	0.0192 (8)	0.0012 (7)	0.0063 (7)	0.0042 (7)
C3	0.0245 (8)	0.0323 (10)	0.0194 (8)	−0.0015 (7)	0.0058 (7)	0.0019 (7)
C4	0.0303 (9)	0.0266 (9)	0.0184 (8)	−0.0050 (7)	0.0038 (7)	0.0009 (7)
C5	0.0449 (12)	0.0329 (10)	0.0306 (10)	0.0089 (9)	0.0093 (9)	0.0077 (8)
C6	0.0360 (10)	0.0347 (10)	0.0256 (9)	−0.0076 (8)	0.0088 (8)	0.0066 (8)
C7	0.0435 (11)	0.0377 (11)	0.0280 (10)	−0.0156 (9)	0.0027 (9)	0.0023 (8)
C8	0.0451 (11)	0.0270 (10)	0.0284 (10)	0.0047 (8)	0.0106 (8)	−0.0026 (8)
C9	0.0223 (8)	0.0219 (8)	0.0197 (8)	0.0005 (6)	0.0057 (6)	0.0007 (6)
C10	0.0261 (8)	0.0292 (9)	0.0196 (8)	0.0038 (7)	0.0085 (7)	0.0043 (7)
C11	0.0250 (8)	0.0261 (9)	0.0240 (8)	0.0005 (7)	0.0063 (7)	0.0026 (7)
C12	0.0214 (8)	0.0245 (9)	0.0227 (8)	0.0035 (6)	0.0070 (6)	0.0027 (7)
C13	0.0346 (10)	0.0407 (11)	0.0311 (10)	0.0020 (8)	0.0156 (8)	0.0118 (8)
C14	0.0390 (10)	0.0397 (11)	0.0183 (8)	0.0057 (9)	0.0073 (7)	0.0001 (8)
C15	0.0298 (9)	0.0330 (10)	0.0351 (10)	0.0058 (8)	0.0139 (8)	−0.0034 (8)
C16	0.0232 (8)	0.0332 (10)	0.0246 (9)	−0.0033 (7)	0.0047 (7)	0.0036 (7)

Geometric parameters (Å, º)

Cl1—C1	1.7786 (17)	C8—H81	0.9800
Cl2—C9	1.7915 (17)	C8—H82	0.9800
S1—C1	1.8462 (16)	C8—H83	0.9800
S1—S2	2.0243 (6)	C9—C10	1.601 (2)
S2—C9	1.8146 (17)	C9—C12	1.589 (2)
O1—C3	1.204 (2)	C10—C13	1.523 (2)
O2—C11	1.200 (2)	C10—C11	1.530 (2)
C1—C2	1.595 (2)	C10—C14	1.538 (2)
C1—C4	1.590 (2)	C11—C12	1.526 (2)
C2—C5	1.519 (2)	C12—C15	1.522 (2)
C2—C3	1.520 (2)	C12—C16	1.536 (2)
C2—C6	1.539 (2)	C13—H131	0.9800
C3—C4	1.529 (2)	C13—H132	0.9800
C4—C7	1.526 (3)	C13—H133	0.9800
C4—C8	1.536 (3)	C14—H141	0.9800
C5—H51	0.9800	C14—H142	0.9800
C5—H52	0.9800	C14—H143	0.9800
C5—H53	0.9800	C15—H151	0.9800
C6—H61	0.9800	C15—H152	0.9800
C6—H62	0.9800	C15—H153	0.9800
C6—H63	0.9800	C16—H161	0.9800
C7—H71	0.9800	C16—H162	0.9800
C7—H72	0.9800	C16—H163	0.9800
C7—H73	0.9800
C1—S1—S2	109.71 (6)	H82—C8—H83	109.5
C9—S2—S1	106.17 (6)	C10—C9—C12	90.52 (12)
C2—C1—C4	90.28 (12)	C12—C9—Cl2	111.97 (11)
C4—C1—Cl1	112.62 (11)	C10—C9—Cl2	112.25 (11)
C2—C1—Cl1	112.22 (11)	C12—C9—S2	119.33 (11)
C4—C1—S1	120.07 (11)	C10—C9—S2	112.87 (11)
C2—C1—S1	110.29 (11)	Cl2—C9—S2	108.91 (8)
Cl1—C1—S1	109.91 (8)	C13—C10—C11	113.45 (14)
C5—C2—C3	115.52 (15)	C13—C10—C14	109.43 (14)
C5—C2—C6	109.66 (15)	C11—C10—C14	112.69 (15)
C3—C2—C6	110.98 (14)	C13—C10—C9	118.97 (15)
C5—C2—C1	117.46 (14)	C9—C10—C11	85.79 (12)
C1—C2—C3	86.26 (12)	C14—C10—C9	114.76 (14)
C6—C2—C1	115.24 (14)	O2—C11—C12	132.43 (16)
O1—C3—C2	132.01 (16)	O2—C11—C10	131.76 (16)
O1—C3—C4	132.43 (17)	C10—C11—C12	95.69 (13)
C2—C3—C4	95.53 (13)	C15—C12—C11	115.66 (14)
C7—C4—C3	114.26 (15)	C15—C12—C16	109.92 (14)
C7—C4—C8	109.89 (16)	C11—C12—C16	109.72 (14)
C3—C4—C8	111.04 (14)	C15—C12—C9	118.86 (14)
C7—C4—C1	118.92 (15)	C9—C12—C11	86.33 (12)
C1—C4—C3	86.12 (12)	C16—C12—C9	114.39 (14)
C8—C4—C1	114.65 (14)	C10—C13—H131	109.5
C2—C5—H51	109.5	C10—C13—H132	109.5
C2—C5—H52	109.5	H131—C13—H132	109.5
H51—C5—H52	109.5	C10—C13—H133	109.5
C2—C5—H53	109.5	H131—C13—H133	109.5
H51—C5—H53	109.5	H132—C13—H133	109.5
H52—C5—H53	109.5	C10—C14—H141	109.5
C2—C6—H61	109.5	C10—C14—H142	109.5
C2—C6—H62	109.5	H141—C14—H142	109.5
H61—C6—H62	109.5	C10—C14—H143	109.5
C2—C6—H63	109.5	H141—C14—H143	109.5
H61—C6—H63	109.5	H142—C14—H143	109.5
H62—C6—H63	109.5	C12—C15—H151	109.5
C4—C7—H71	109.5	C12—C15—H152	109.5
C4—C7—H72	109.5	H151—C15—H152	109.5
H71—C7—H72	109.5	C12—C15—H153	109.5
C4—C7—H73	109.5	H151—C15—H153	109.5
H71—C7—H73	109.5	H152—C15—H153	109.5
H72—C7—H73	109.5	C12—C16—H161	109.5
C4—C8—H81	109.5	C12—C16—H162	109.5
C4—C8—H82	109.5	H161—C16—H162	109.5
H81—C8—H82	109.5	C12—C16—H163	109.5
C4—C8—H83	109.5	H161—C16—H163	109.5
H81—C8—H83	109.5	H162—C16—H163	109.5
C1—S1—S2—C9	−97.90 (8)	S1—S2—C9—C12	−58.57 (13)
S2—S1—C1—C4	105.37 (12)	S1—S2—C9—C10	−162.95 (10)
S2—S1—C1—C2	−151.91 (9)	S1—S2—C9—Cl2	71.68 (8)
S2—S1—C1—Cl1	−27.65 (10)	C12—C9—C10—C13	124.07 (16)
C4—C1—C2—C5	−126.84 (16)	Cl2—C9—C10—C13	9.99 (19)
Cl1—C1—C2—C5	−12.17 (19)	S2—C9—C10—C13	−113.56 (15)
S1—C1—C2—C5	110.74 (15)	C12—C9—C10—C11	9.53 (12)
C4—C1—C2—C3	−9.93 (12)	Cl2—C9—C10—C11	−104.55 (12)
Cl1—C1—C2—C3	104.74 (12)	S2—C9—C10—C11	131.90 (12)
S1—C1—C2—C3	−132.34 (11)	C12—C9—C10—C14	−103.55 (15)
C4—C1—C2—C6	101.53 (16)	Cl2—C9—C10—C14	142.38 (13)
Cl1—C1—C2—C6	−143.80 (13)	S2—C9—C10—C14	18.82 (18)
S1—C1—C2—C6	−20.88 (18)	C13—C10—C11—O2	46.6 (3)
C5—C2—C3—O1	−49.2 (3)	C14—C10—C11—O2	−78.5 (2)
C6—C2—C3—O1	76.4 (2)	C9—C10—C11—O2	166.4 (2)
C1—C2—C3—O1	−167.9 (2)	C13—C10—C11—C12	−129.82 (15)
C5—C2—C3—C4	129.12 (15)	C14—C10—C11—C12	105.13 (15)
C6—C2—C3—C4	−105.26 (15)	C9—C10—C11—C12	−9.98 (13)
C1—C2—C3—C4	10.38 (13)	O2—C11—C12—C15	−45.9 (3)
O1—C3—C4—C7	47.8 (3)	C10—C11—C12—C15	130.42 (15)
C2—C3—C4—C7	−130.49 (16)	O2—C11—C12—C16	79.1 (2)
O1—C3—C4—C8	−77.2 (2)	C10—C11—C12—C16	−104.57 (15)
C2—C3—C4—C8	104.53 (15)	O2—C11—C12—C9	−166.3 (2)
O1—C3—C4—C1	167.9 (2)	C10—C11—C12—C9	10.04 (13)
C2—C3—C4—C1	−10.41 (13)	C10—C9—C12—C15	−126.95 (16)
C2—C1—C4—C7	125.53 (16)	Cl2—C9—C12—C15	−12.62 (19)
Cl1—C1—C4—C7	11.22 (19)	S2—C9—C12—C15	116.25 (15)
S1—C1—C4—C7	−120.66 (15)	C10—C9—C12—C11	−9.55 (12)
C2—C1—C4—C3	9.87 (12)	Cl2—C9—C12—C11	104.77 (12)
Cl1—C1—C4—C3	−104.44 (12)	S2—C9—C12—C11	−126.36 (12)
S1—C1—C4—C3	123.68 (13)	C10—C9—C12—C16	100.45 (15)
C2—C1—C4—C8	−101.52 (15)	Cl2—C9—C12—C16	−145.22 (12)
Cl1—C1—C4—C8	144.16 (13)	S2—C9—C12—C16	−16.35 (19)
S1—C1—C4—C8	12.3 (2)

(V) 1,3-bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)trisulfane

Crystal data

C16H24Cl2O2S3	F(000) = 1744
Mr = 415.45	Dx = 1.370 Mg m^−3
Monoclinic, P21/c	Melting point = 383–385 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.0673 (1) Å	Cell parameters from 77343 reflections
b = 25.7808 (2) Å	θ = 2.0–30.0°
c = 13.1619 (1) Å	µ = 0.64 mm^−1
β = 114.6674 (3)°	T = 160 K
V = 4029.43 (5) Å^3	Block, colourless
Z = 8	0.38 × 0.30 × 0.22 mm

Data collection

Nonius KappaCCD area-detector diffractometer	11777 independent reflections
Radiation source: Nonius FR591 sealed tube generator	9407 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.050
Detector resolution: 9 pixels mm^-1	θmax = 30.0°, θmin = 2.9°
ϕ and ω scans with κ offsets	h = −18→18
Absorption correction: multi-scan (Blessing, 1995)	k = −36→36
Tmin = 0.826, Tmax = 0.890	l = −18→18
93177 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.086	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.039P)^2 + 1.605P] where P = (Fo^2 + 2Fc^2)/3
11772 reflections	(Δ/σ)max = 0.002
431 parameters	Δρmax = 0.72 e Å^−3
0 restraints	Δρmin = −0.39 e Å^−3

Special details

Experimental. Solvent used: hexane/dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.433 (1) Frames collected: 753 Seconds exposure per frame: 18 Degrees rotation per frame: 1.2 Crystal-Detector distance (mm): 40.0

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
Cl1	−0.02672 (3)	0.588653 (15)	0.67054 (3)	0.03028 (8)
Cl2	0.03901 (3)	0.695356 (14)	1.04711 (3)	0.02683 (8)
S1	0.09745 (3)	0.574333 (14)	0.91119 (3)	0.02538 (8)
S2	0.18540 (3)	0.639084 (14)	0.90639 (3)	0.02589 (8)
S3	0.07172 (3)	0.698115 (14)	0.83988 (3)	0.02374 (8)
O1	0.13271 (13)	0.43230 (5)	0.69596 (16)	0.0618 (5)
O2	0.16487 (11)	0.85621 (5)	0.95325 (13)	0.0457 (3)
C1	0.06598 (12)	0.54538 (5)	0.77555 (12)	0.0216 (3)
C2	0.16760 (12)	0.52558 (6)	0.74884 (13)	0.0254 (3)
C3	0.11131 (14)	0.47243 (6)	0.72902 (15)	0.0329 (3)
C4	0.01761 (13)	0.48791 (6)	0.76338 (14)	0.0273 (3)
C5	0.17823 (16)	0.54900 (8)	0.64729 (15)	0.0405 (4)
H51	0.1996	0.5856	0.6618	0.061*
H52	0.1059	0.5462	0.5819	0.061*
H53	0.2361	0.5302	0.6329	0.061*
C6	0.28335 (13)	0.52345 (7)	0.84789 (15)	0.0334 (4)
H61	0.3343	0.5020	0.8281	0.050*
H62	0.2758	0.5084	0.9128	0.050*
H63	0.3140	0.5586	0.8661	0.050*
C7	0.03006 (18)	0.46208 (7)	0.87293 (17)	0.0435 (4)
H71	−0.0242	0.4773	0.8979	0.065*
H72	0.1066	0.4676	0.9302	0.065*
H73	0.0157	0.4248	0.8607	0.065*
C8	−0.10041 (14)	0.47846 (7)	0.67278 (16)	0.0388 (4)
H81	−0.1067	0.4939	0.6023	0.058*
H82	−0.1560	0.4944	0.6950	0.058*
H83	−0.1144	0.4411	0.6627	0.058*
C9	0.08331 (11)	0.73524 (5)	0.96154 (11)	0.0201 (3)
C10	0.01791 (12)	0.78874 (6)	0.92120 (13)	0.0245 (3)
C11	0.13399 (13)	0.81381 (6)	0.96543 (14)	0.0271 (3)
C12	0.19846 (12)	0.76558 (5)	1.02601 (12)	0.0238 (3)
C13	−0.05577 (16)	0.79669 (7)	0.79695 (15)	0.0390 (4)
H131	−0.0806	0.8329	0.7836	0.058*
H132	−0.1216	0.7739	0.7737	0.058*
H133	−0.0123	0.7884	0.7537	0.058*
C14	−0.04654 (14)	0.80678 (6)	0.98898 (15)	0.0324 (3)
H141	0.0017	0.8031	1.0690	0.049*
H142	−0.1143	0.7855	0.9695	0.049*
H143	−0.0682	0.8432	0.9719	0.049*
C15	0.29928 (13)	0.75312 (7)	1.00028 (16)	0.0355 (4)
H151	0.2743	0.7500	0.9192	0.053*
H152	0.3332	0.7203	1.0363	0.053*
H153	0.3550	0.7810	1.0288	0.053*
C16	0.23636 (14)	0.76976 (7)	1.15272 (13)	0.0341 (4)
H161	0.2941	0.7968	1.1827	0.051*
H162	0.2676	0.7364	1.1878	0.051*
H163	0.1716	0.7788	1.1686	0.051*
Cl21	0.55028 (3)	0.379865 (15)	0.26866 (3)	0.02916 (8)
Cl22	0.43895 (3)	0.575603 (15)	0.14433 (3)	0.03025 (8)
S21	0.35573 (3)	0.444092 (15)	0.13824 (3)	0.02835 (9)
S22	0.38074 (3)	0.475055 (14)	0.28959 (3)	0.02596 (8)
S23	0.53108 (3)	0.514232 (14)	0.35012 (3)	0.02440 (8)
O21	0.27743 (11)	0.26508 (5)	0.06956 (12)	0.0464 (3)
O22	0.47234 (11)	0.69911 (5)	0.37382 (13)	0.0443 (3)
C21	0.40492 (11)	0.37764 (5)	0.17175 (12)	0.0219 (3)
C22	0.33281 (12)	0.33785 (6)	0.20746 (13)	0.0261 (3)
C23	0.32033 (13)	0.30635 (6)	0.10489 (14)	0.0287 (3)
C24	0.38148 (13)	0.34469 (6)	0.06226 (12)	0.0249 (3)
C25	0.39527 (17)	0.30777 (8)	0.31592 (16)	0.0454 (5)
H251	0.3450	0.2815	0.3242	0.068*
H252	0.4195	0.3317	0.3794	0.068*
H253	0.4613	0.2907	0.3137	0.068*
C26	0.22068 (14)	0.35854 (8)	0.20075 (17)	0.0410 (4)
H261	0.1819	0.3774	0.1304	0.062*
H262	0.2345	0.3820	0.2637	0.062*
H263	0.1737	0.3295	0.2038	0.062*
C27	0.29920 (16)	0.36946 (7)	−0.04749 (14)	0.0386 (4)
H271	0.3363	0.3984	−0.0668	0.058*
H272	0.2328	0.3822	−0.0384	0.058*
H273	0.2759	0.3435	−0.1073	0.058*
C28	0.48290 (14)	0.32264 (6)	0.04852 (14)	0.0323 (3)
H281	0.5322	0.3048	0.1174	0.048*
H282	0.5245	0.3509	0.0330	0.048*
H283	0.4574	0.2980	−0.0138	0.048*
C29	0.48614 (12)	0.57861 (5)	0.29427 (11)	0.0216 (3)
C30	0.57805 (12)	0.62283 (6)	0.34926 (12)	0.0238 (3)
C31	0.48196 (13)	0.65397 (6)	0.35750 (12)	0.0259 (3)
C32	0.39927 (12)	0.60877 (5)	0.32809 (12)	0.0220 (3)
C33	0.67236 (13)	0.60886 (7)	0.46285 (14)	0.0326 (3)
H331	0.7258	0.5854	0.4518	0.049*
H332	0.6400	0.5917	0.5092	0.049*
H333	0.7116	0.6405	0.5002	0.049*
C34	0.62990 (15)	0.64855 (7)	0.27779 (15)	0.0336 (4)
H341	0.5700	0.6589	0.2059	0.050*
H342	0.6806	0.6240	0.2650	0.050*
H343	0.6724	0.6793	0.3165	0.050*
C35	0.39210 (13)	0.58841 (6)	0.43468 (13)	0.0267 (3)
H351	0.3543	0.6142	0.4618	0.040*
H352	0.4682	0.5821	0.4922	0.040*
H353	0.3492	0.5559	0.4179	0.040*
C36	0.28156 (13)	0.61938 (6)	0.23822 (14)	0.0302 (3)
H361	0.2402	0.6412	0.2693	0.045*
H362	0.2415	0.5865	0.2125	0.045*
H363	0.2873	0.6373	0.1751	0.045*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.03177 (19)	0.02746 (19)	0.02713 (18)	0.00730 (15)	0.00788 (15)	0.00304 (14)
Cl2	0.02975 (18)	0.02521 (18)	0.02847 (17)	−0.00534 (14)	0.01506 (14)	0.00014 (13)
S1	0.03294 (19)	0.02089 (17)	0.02439 (17)	0.00021 (14)	0.01401 (15)	−0.00086 (13)
S2	0.02341 (17)	0.02086 (17)	0.03225 (19)	0.00063 (13)	0.01048 (15)	−0.00417 (14)
S3	0.02755 (17)	0.02053 (17)	0.02261 (17)	0.00181 (13)	0.00995 (14)	−0.00214 (13)
O1	0.0532 (9)	0.0329 (7)	0.1141 (14)	−0.0060 (6)	0.0495 (9)	−0.0307 (8)
O2	0.0411 (7)	0.0247 (6)	0.0757 (10)	−0.0034 (5)	0.0287 (7)	0.0107 (6)
C1	0.0226 (6)	0.0193 (7)	0.0224 (6)	0.0016 (5)	0.0089 (5)	0.0004 (5)
C2	0.0255 (7)	0.0225 (7)	0.0304 (7)	0.0005 (6)	0.0140 (6)	−0.0018 (6)
C3	0.0290 (8)	0.0253 (8)	0.0454 (9)	0.0005 (6)	0.0166 (7)	−0.0068 (7)
C4	0.0279 (7)	0.0201 (7)	0.0367 (8)	−0.0025 (6)	0.0161 (6)	−0.0037 (6)
C5	0.0384 (9)	0.0552 (12)	0.0367 (9)	0.0036 (8)	0.0243 (8)	0.0027 (8)
C6	0.0253 (7)	0.0322 (9)	0.0410 (9)	0.0049 (6)	0.0121 (7)	−0.0004 (7)
C7	0.0577 (12)	0.0269 (9)	0.0508 (11)	−0.0085 (8)	0.0273 (10)	0.0048 (8)
C8	0.0310 (8)	0.0345 (9)	0.0497 (10)	−0.0085 (7)	0.0156 (8)	−0.0143 (8)
C9	0.0210 (6)	0.0185 (6)	0.0218 (6)	−0.0016 (5)	0.0098 (5)	−0.0017 (5)
C10	0.0239 (7)	0.0192 (7)	0.0293 (7)	0.0020 (5)	0.0101 (6)	−0.0011 (6)
C11	0.0291 (7)	0.0209 (7)	0.0352 (8)	−0.0016 (6)	0.0173 (6)	−0.0014 (6)
C12	0.0208 (6)	0.0192 (7)	0.0305 (7)	−0.0039 (5)	0.0099 (6)	−0.0035 (6)
C13	0.0437 (10)	0.0295 (9)	0.0341 (9)	0.0111 (7)	0.0067 (8)	0.0035 (7)
C14	0.0287 (8)	0.0258 (8)	0.0465 (10)	0.0011 (6)	0.0193 (7)	−0.0072 (7)
C15	0.0236 (7)	0.0322 (9)	0.0531 (10)	−0.0055 (6)	0.0185 (7)	−0.0067 (8)
C16	0.0318 (8)	0.0319 (9)	0.0305 (8)	−0.0079 (7)	0.0048 (7)	−0.0064 (7)
Cl21	0.01906 (16)	0.02944 (19)	0.03357 (19)	−0.00032 (13)	0.00561 (14)	−0.00332 (15)
Cl22	0.0412 (2)	0.02914 (19)	0.01997 (16)	−0.00117 (15)	0.01227 (15)	−0.00067 (13)
S21	0.0341 (2)	0.01997 (18)	0.02572 (18)	0.00419 (14)	0.00723 (15)	0.00070 (14)
S22	0.02739 (18)	0.02142 (17)	0.03056 (19)	0.00073 (14)	0.01358 (15)	−0.00151 (14)
S23	0.02440 (17)	0.01990 (17)	0.02751 (18)	0.00385 (13)	0.00945 (14)	0.00193 (13)
O21	0.0416 (7)	0.0334 (7)	0.0640 (9)	−0.0142 (6)	0.0217 (7)	−0.0131 (6)
O22	0.0433 (7)	0.0240 (6)	0.0703 (9)	−0.0037 (5)	0.0284 (7)	−0.0139 (6)
C21	0.0192 (6)	0.0199 (7)	0.0238 (7)	0.0013 (5)	0.0061 (5)	0.0005 (5)
C22	0.0218 (7)	0.0273 (8)	0.0287 (7)	−0.0037 (6)	0.0100 (6)	0.0012 (6)
C23	0.0220 (7)	0.0241 (7)	0.0354 (8)	−0.0013 (6)	0.0075 (6)	−0.0014 (6)
C24	0.0281 (7)	0.0205 (7)	0.0245 (7)	0.0010 (6)	0.0094 (6)	−0.0013 (5)
C25	0.0467 (11)	0.0466 (11)	0.0375 (10)	−0.0103 (9)	0.0122 (8)	0.0139 (8)
C26	0.0269 (8)	0.0462 (11)	0.0551 (11)	−0.0073 (7)	0.0222 (8)	−0.0083 (9)
C27	0.0472 (10)	0.0368 (9)	0.0246 (8)	0.0087 (8)	0.0079 (7)	−0.0009 (7)
C28	0.0376 (9)	0.0273 (8)	0.0357 (8)	0.0012 (7)	0.0190 (7)	−0.0031 (7)
C29	0.0259 (7)	0.0193 (7)	0.0189 (6)	0.0011 (5)	0.0088 (5)	0.0006 (5)
C30	0.0252 (7)	0.0226 (7)	0.0243 (7)	−0.0020 (5)	0.0111 (6)	−0.0026 (5)
C31	0.0278 (7)	0.0239 (7)	0.0266 (7)	0.0002 (6)	0.0121 (6)	−0.0025 (6)
C32	0.0228 (6)	0.0193 (7)	0.0236 (7)	0.0030 (5)	0.0095 (5)	0.0007 (5)
C33	0.0257 (7)	0.0384 (9)	0.0297 (8)	−0.0028 (7)	0.0076 (6)	−0.0024 (7)
C34	0.0362 (9)	0.0323 (9)	0.0375 (9)	−0.0069 (7)	0.0206 (7)	−0.0003 (7)
C35	0.0279 (7)	0.0283 (8)	0.0264 (7)	0.0026 (6)	0.0139 (6)	0.0006 (6)
C36	0.0247 (7)	0.0299 (8)	0.0318 (8)	0.0049 (6)	0.0075 (6)	0.0046 (6)

Geometric parameters (Å, º)

Cl1—C1	1.7957 (14)	Cl21—C21	1.7934 (14)
Cl2—C9	1.7903 (14)	Cl22—C29	1.8070 (14)
S1—C1	1.8168 (14)	S21—C21	1.8181 (14)
S1—S2	2.0426 (5)	S21—S22	2.0417 (5)
S2—S3	2.0502 (5)	S22—S23	2.0513 (5)
S3—C9	1.8167 (14)	S23—C29	1.8110 (14)
O1—C3	1.200 (2)	O21—C23	1.2021 (19)
O2—C11	1.1990 (19)	O22—C31	1.1993 (19)
C1—C2	1.593 (2)	C21—C22	1.591 (2)
C1—C4	1.592 (2)	C21—C24	1.589 (2)
C2—C5	1.525 (2)	C22—C23	1.525 (2)
C2—C3	1.525 (2)	C22—C26	1.527 (2)
C2—C6	1.531 (2)	C22—C25	1.527 (2)
C3—C4	1.525 (2)	C23—C24	1.518 (2)
C4—C8	1.525 (2)	C24—C28	1.521 (2)
C4—C7	1.534 (2)	C24—C27	1.534 (2)
C5—H51	0.9800	C25—H251	0.9800
C5—H52	0.9800	C25—H252	0.9800
C5—H53	0.9800	C25—H253	0.9800
C6—H61	0.9800	C26—H261	0.9800
C6—H62	0.9800	C26—H262	0.9800
C6—H63	0.9800	C26—H263	0.9800
C7—H71	0.9800	C27—H271	0.9800
C7—H72	0.9800	C27—H272	0.9800
C7—H73	0.9800	C27—H273	0.9800
C8—H81	0.9800	C28—H281	0.9800
C8—H82	0.9800	C28—H282	0.9800
C8—H83	0.9800	C28—H283	0.9800
C9—C10	1.593 (2)	C29—C30	1.594 (2)
C9—C12	1.5905 (19)	C29—C32	1.585 (2)
C10—C11	1.523 (2)	C30—C34	1.522 (2)
C10—C13	1.526 (2)	C30—C33	1.532 (2)
C10—C14	1.532 (2)	C30—C31	1.532 (2)
C11—C12	1.527 (2)	C31—C32	1.525 (2)
C12—C15	1.525 (2)	C32—C36	1.524 (2)
C12—C16	1.533 (2)	C32—C35	1.537 (2)
C13—H131	0.9800	C33—H331	0.9800
C13—H132	0.9800	C33—H332	0.9800
C13—H133	0.9800	C33—H333	0.9800
C14—H141	0.9800	C34—H341	0.9800
C14—H142	0.9800	C34—H342	0.9800
C14—H143	0.9800	C34—H343	0.9800
C15—H151	0.9800	C35—H351	0.9800
C15—H152	0.9800	C35—H352	0.9800
C15—H153	0.9800	C35—H353	0.9800
C16—H161	0.9800	C36—H361	0.9800
C16—H162	0.9800	C36—H362	0.9800
C16—H163	0.9800	C36—H363	0.9800
C1—S1—S2	101.82 (5)	C21—S21—S22	103.61 (5)
S1—S2—S3	107.65 (2)	S21—S22—S23	107.99 (2)
C9—S3—S2	103.63 (5)	C29—S23—S22	101.41 (5)
C2—C1—C4	90.69 (10)	C22—C21—C24	90.54 (11)
C4—C1—Cl1	112.87 (10)	C24—C21—Cl21	114.09 (10)
C2—C1—Cl1	112.71 (10)	C22—C21—Cl21	113.12 (10)
C4—C1—S1	113.49 (10)	C24—C21—S21	111.66 (10)
C2—C1—S1	118.74 (10)	C22—C21—S21	119.09 (10)
Cl1—C1—S1	107.72 (7)	Cl21—C21—S21	107.74 (7)
C5—C2—C3	114.81 (14)	C23—C22—C26	112.92 (13)
C5—C2—C6	109.97 (13)	C23—C22—C25	112.03 (14)
C3—C2—C6	110.37 (13)	C26—C22—C25	110.92 (15)
C5—C2—C1	117.11 (13)	C21—C22—C23	86.53 (11)
C1—C2—C3	86.49 (11)	C26—C22—C21	115.47 (13)
C6—C2—C1	116.23 (12)	C25—C22—C21	116.88 (13)
O1—C3—C4	132.13 (16)	O21—C23—C24	131.74 (16)
O1—C3—C2	131.91 (16)	O21—C23—C22	132.40 (16)
C2—C3—C4	95.95 (12)	C22—C23—C24	95.86 (12)
C8—C4—C3	113.67 (14)	C23—C24—C28	114.83 (13)
C8—C4—C7	109.98 (14)	C23—C24—C27	110.41 (13)
C3—C4—C7	112.45 (14)	C28—C24—C27	110.28 (13)
C8—C4—C1	117.18 (13)	C21—C24—C23	86.84 (11)
C1—C4—C3	86.51 (11)	C28—C24—C21	117.40 (12)
C7—C4—C1	115.31 (13)	C27—C24—C21	115.18 (12)
C2—C5—H51	109.5	C22—C25—H251	109.5
C2—C5—H52	109.5	C22—C25—H252	109.5
H51—C5—H52	109.5	H251—C25—H252	109.5
C2—C5—H53	109.5	C22—C25—H253	109.5
H51—C5—H53	109.5	H251—C25—H253	109.5
H52—C5—H53	109.5	H252—C25—H253	109.5
C2—C6—H61	109.5	C22—C26—H261	109.5
C2—C6—H62	109.5	C22—C26—H262	109.5
H61—C6—H62	109.5	H261—C26—H262	109.5
C2—C6—H63	109.5	C22—C26—H263	109.5
H61—C6—H63	109.5	H261—C26—H263	109.5
H62—C6—H63	109.5	H262—C26—H263	109.5
C4—C7—H71	109.5	C24—C27—H271	109.5
C4—C7—H72	109.5	C24—C27—H272	109.5
H71—C7—H72	109.5	H271—C27—H272	109.5
C4—C7—H73	109.5	C24—C27—H273	109.5
H71—C7—H73	109.5	H271—C27—H273	109.5
H72—C7—H73	109.5	H272—C27—H273	109.5
C4—C8—H81	109.5	C24—C28—H281	109.5
C4—C8—H82	109.5	C24—C28—H282	109.5
H81—C8—H82	109.5	H281—C28—H282	109.5
C4—C8—H83	109.5	C24—C28—H283	109.5
H81—C8—H83	109.5	H281—C28—H283	109.5
H82—C8—H83	109.5	H282—C28—H283	109.5
C10—C9—C12	90.49 (10)	C30—C29—C32	90.79 (10)
C12—C9—Cl2	115.40 (10)	C32—C29—Cl22	111.70 (9)
C10—C9—Cl2	115.96 (10)	C30—C29—Cl22	112.07 (10)
C12—C9—S3	116.21 (9)	C32—C29—S23	118.97 (10)
C10—C9—S3	109.07 (9)	C30—C29—S23	114.58 (10)
Cl2—C9—S3	108.78 (7)	Cl22—C29—S23	108.00 (7)
C11—C10—C13	115.78 (14)	C34—C30—C33	108.75 (13)
C11—C10—C14	110.51 (13)	C34—C30—C31	113.89 (13)
C13—C10—C14	109.20 (13)	C33—C30—C31	113.80 (13)
C9—C10—C11	85.97 (10)	C34—C30—C29	118.45 (12)
C13—C10—C9	118.96 (12)	C33—C30—C29	114.96 (12)
C14—C10—C9	114.68 (13)	C29—C30—C31	85.55 (10)
O2—C11—C10	132.28 (15)	O22—C31—C32	132.11 (14)
O2—C11—C12	132.01 (15)	O22—C31—C30	132.18 (15)
C10—C11—C12	95.65 (11)	C30—C31—C32	95.53 (11)
C15—C12—C11	113.27 (13)	C36—C32—C31	116.02 (12)
C15—C12—C16	109.86 (13)	C36—C32—C35	110.09 (12)
C11—C12—C16	111.61 (13)	C31—C32—C35	109.63 (12)
C15—C12—C9	119.37 (12)	C36—C32—C29	118.64 (12)
C9—C12—C11	85.92 (10)	C29—C32—C31	86.07 (10)
C16—C12—C9	114.80 (12)	C35—C32—C29	114.36 (11)
C10—C13—H131	109.5	C30—C33—H331	109.5
C10—C13—H132	109.5	C30—C33—H332	109.5
H131—C13—H132	109.5	H331—C33—H332	109.5
C10—C13—H133	109.5	C30—C33—H333	109.5
H131—C13—H133	109.5	H331—C33—H333	109.5
H132—C13—H133	109.5	H332—C33—H333	109.5
C10—C14—H141	109.5	C30—C34—H341	109.5
C10—C14—H142	109.5	C30—C34—H342	109.5
H141—C14—H142	109.5	H341—C34—H342	109.5
C10—C14—H143	109.5	C30—C34—H343	109.5
H141—C14—H143	109.5	H341—C34—H343	109.5
H142—C14—H143	109.5	H342—C34—H343	109.5
C12—C15—H151	109.5	C32—C35—H351	109.5
C12—C15—H152	109.5	C32—C35—H352	109.5
H151—C15—H152	109.5	H351—C35—H352	109.5
C12—C15—H153	109.5	C32—C35—H353	109.5
H151—C15—H153	109.5	H351—C35—H353	109.5
H152—C15—H153	109.5	H352—C35—H353	109.5
C12—C16—H161	109.5	C32—C36—H361	109.5
C12—C16—H162	109.5	C32—C36—H362	109.5
H161—C16—H162	109.5	H361—C36—H362	109.5
C12—C16—H163	109.5	C32—C36—H363	109.5
H161—C16—H163	109.5	H361—C36—H363	109.5
H162—C16—H163	109.5	H362—C36—H363	109.5
C1—S1—S2—S3	89.80 (5)	C21—S21—S22—S23	97.00 (5)
S1—S2—S3—C9	100.76 (5)	S21—S22—S23—C29	90.52 (5)
S2—S1—C1—C4	168.77 (9)	S22—S21—C21—C24	174.40 (9)
S2—S1—C1—C2	64.09 (11)	S22—S21—C21—C22	70.95 (11)
S2—S1—C1—Cl1	−65.51 (7)	S22—S21—C21—Cl21	−59.57 (7)
C4—C1—C2—C5	120.55 (15)	C24—C21—C22—C23	3.48 (11)
Cl1—C1—C2—C5	5.31 (17)	Cl21—C21—C22—C23	−113.13 (11)
S1—C1—C2—C5	−121.98 (14)	S21—C21—C22—C23	118.79 (11)
C4—C1—C2—C3	4.38 (12)	C24—C21—C22—C26	−110.30 (14)
Cl1—C1—C2—C3	−110.86 (11)	Cl21—C21—C22—C26	133.09 (13)
S1—C1—C2—C3	121.85 (12)	S21—C21—C22—C26	5.01 (18)
C4—C1—C2—C6	−106.62 (14)	C24—C21—C22—C25	116.47 (15)
Cl1—C1—C2—C6	138.14 (12)	Cl21—C21—C22—C25	−0.14 (18)
S1—C1—C2—C6	10.85 (17)	S21—C21—C22—C25	−128.22 (14)
C5—C2—C3—O1	56.1 (3)	C26—C22—C23—O21	−67.8 (2)
C6—C2—C3—O1	−68.9 (3)	C25—C22—C23—O21	58.3 (2)
C1—C2—C3—O1	174.4 (2)	C21—C22—C23—O21	175.96 (19)
C5—C2—C3—C4	−122.94 (14)	C26—C22—C23—C24	112.59 (14)
C6—C2—C3—C4	112.11 (14)	C25—C22—C23—C24	−121.32 (14)
C1—C2—C3—C4	−4.60 (12)	C21—C22—C23—C24	−3.66 (11)
O1—C3—C4—C8	−56.2 (3)	O21—C23—C24—C28	−57.1 (2)
C2—C3—C4—C8	122.83 (14)	C22—C23—C24—C28	122.50 (14)
O1—C3—C4—C7	69.6 (3)	O21—C23—C24—C27	68.3 (2)
C2—C3—C4—C7	−111.39 (15)	C22—C23—C24—C27	−112.07 (13)
O1—C3—C4—C1	−174.4 (2)	O21—C23—C24—C21	−175.96 (18)
C2—C3—C4—C1	4.60 (12)	C22—C23—C24—C21	3.66 (11)
C2—C1—C4—C8	−119.27 (14)	C22—C21—C24—C23	−3.49 (11)
Cl1—C1—C4—C8	−4.18 (17)	Cl21—C21—C24—C23	112.25 (11)
S1—C1—C4—C8	118.75 (13)	S21—C21—C24—C23	−125.29 (10)
C2—C1—C4—C3	−4.38 (11)	C22—C21—C24—C28	−119.92 (14)
Cl1—C1—C4—C3	110.71 (11)	Cl21—C21—C24—C28	−4.18 (17)
S1—C1—C4—C3	−126.36 (11)	S21—C21—C24—C28	118.28 (13)
C2—C1—C4—C7	108.84 (15)	C22—C21—C24—C27	107.61 (14)
Cl1—C1—C4—C7	−136.07 (13)	Cl21—C21—C24—C27	−136.65 (13)
S1—C1—C4—C7	−13.14 (17)	S21—C21—C24—C27	−14.19 (17)
S2—S3—C9—C12	68.30 (10)	S22—S23—C29—C32	60.12 (11)
S2—S3—C9—C10	168.68 (8)	S22—S23—C29—C30	165.82 (9)
S2—S3—C9—Cl2	−63.96 (7)	S22—S23—C29—Cl22	−68.51 (7)
C12—C9—C10—C11	10.35 (11)	C32—C29—C30—C34	−125.38 (14)
Cl2—C9—C10—C11	129.12 (11)	Cl22—C29—C30—C34	−11.52 (17)
S3—C9—C10—C11	−107.71 (10)	S23—C29—C30—C34	112.00 (13)
C12—C9—C10—C13	127.69 (15)	C32—C29—C30—C33	103.66 (13)
Cl2—C9—C10—C13	−113.54 (14)	Cl22—C29—C30—C33	−142.47 (11)
S3—C9—C10—C13	9.63 (17)	S23—C29—C30—C33	−18.96 (16)
C12—C9—C10—C14	−100.40 (13)	C32—C29—C30—C31	−10.56 (10)
Cl2—C9—C10—C14	18.38 (16)	Cl22—C29—C30—C31	103.31 (10)
S3—C9—C10—C14	141.55 (11)	S23—C29—C30—C31	−133.18 (10)
C13—C10—C11—O2	46.2 (2)	C34—C30—C31—O22	−45.3 (2)
C14—C10—C11—O2	−78.6 (2)	C33—C30—C31—O22	80.2 (2)
C9—C10—C11—O2	166.54 (19)	C29—C30—C31—O22	−164.49 (19)
C13—C10—C11—C12	−131.17 (13)	C34—C30—C31—C32	130.25 (13)
C14—C10—C11—C12	104.04 (14)	C33—C30—C31—C32	−104.33 (14)
C9—C10—C11—C12	−10.84 (11)	C29—C30—C31—C32	11.03 (11)
O2—C11—C12—C15	−46.2 (2)	O22—C31—C32—C36	44.4 (2)
C10—C11—C12—C15	131.15 (13)	C30—C31—C32—C36	−131.16 (13)
O2—C11—C12—C16	78.4 (2)	O22—C31—C32—C35	−81.1 (2)
C10—C11—C12—C16	−104.24 (13)	C30—C31—C32—C35	103.40 (12)
O2—C11—C12—C9	−166.54 (19)	O22—C31—C32—C29	164.44 (19)
C10—C11—C12—C9	10.85 (11)	C30—C31—C32—C29	−11.08 (11)
C10—C9—C12—C15	−124.80 (14)	C30—C29—C32—C36	128.21 (13)
Cl2—C9—C12—C15	115.95 (14)	Cl22—C29—C32—C36	14.01 (16)
S3—C9—C12—C15	−13.18 (18)	S23—C29—C32—C36	−112.90 (13)
C10—C9—C12—C11	−10.32 (11)	C30—C29—C32—C31	10.60 (10)
Cl2—C9—C12—C11	−129.58 (10)	Cl22—C29—C32—C31	−103.60 (10)
S3—C9—C12—C11	101.30 (11)	S23—C29—C32—C31	129.49 (11)
C10—C9—C12—C16	101.63 (14)	C30—C29—C32—C35	−99.19 (13)
Cl2—C9—C12—C16	−17.63 (16)	Cl22—C29—C32—C35	146.61 (11)
S3—C9—C12—C16	−146.75 (11)	S23—C29—C32—C35	19.71 (16)

(VII) 1,4-bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)tetrasulfane

Crystal data

C16H24Cl2O2S4	Z = 4
Mr = 447.51	F(000) = 936
Triclinic, P1	Dx = 1.376 Mg m^−3
Hall symbol: -P 1	Melting point = 405–407 K
a = 11.1372 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.0843 (1) Å	Cell parameters from 39875 reflections
c = 16.3379 (2) Å	θ = 2.0–30.0°
α = 71.8478 (5)°	µ = 0.69 mm^−1
β = 89.8055 (5)°	T = 253 K
γ = 73.5431 (5)°	Tablet, colourless
V = 2160.20 (4) Å^3	0.25 × 0.25 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer	12599 independent reflections
Radiation source: Nonius FR591 sealed tube generator	9118 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.042
Detector resolution: 9 pixels mm^-1	θmax = 30.0°, θmin = 2.2°
ϕ and ω scans with κ offsets	h = −15→15
Absorption correction: multi-scan (Blessing, 1995)	k = −18→18
Tmin = 0.884, Tmax = 0.936	l = −22→22
61153 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.114	w = 1/[σ^2(Fo^2) + (0.0529P)^2 + 0.5211P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
12596 reflections	Δρmax = 0.45 e Å^−3
450 parameters	Δρmin = −0.56 e Å^−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0049 (10)

Special details

Experimental. Solvent used: hexane/dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.534 (1) Frames collected: 381 Seconds exposure per frame: 80 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 30.0

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
Cl1	0.60123 (4)	0.27674 (4)	0.08168 (4)	0.05255 (13)
Cl2	0.89837 (4)	−0.26835 (4)	0.22743 (3)	0.05085 (12)
S1	0.56483 (4)	0.10689 (4)	0.01143 (3)	0.04517 (12)
S2	0.66408 (5)	−0.00384 (4)	0.12373 (4)	0.05424 (14)
S3	0.84544 (5)	0.00729 (4)	0.11382 (4)	0.05064 (13)
S4	0.93563 (4)	−0.11413 (4)	0.06302 (3)	0.04337 (12)
O1	0.17854 (16)	0.3565 (2)	0.01191 (17)	0.1224 (9)
O2	1.31772 (15)	−0.37814 (19)	0.19871 (14)	0.0945 (7)
C1	0.48584 (15)	0.23044 (13)	0.04065 (11)	0.0343 (3)
C2	0.39258 (17)	0.32410 (15)	−0.03731 (12)	0.0418 (4)
C3	0.28888 (18)	0.31110 (19)	0.02201 (15)	0.0580 (5)
C4	0.37223 (18)	0.22151 (17)	0.09875 (13)	0.0474 (4)
C5	0.4078 (2)	0.44162 (17)	−0.06262 (18)	0.0703 (7)
H51	0.3373	0.4942	−0.1017	0.105*
H52	0.4839	0.4419	−0.0904	0.105*
H53	0.4118	0.4629	−0.0117	0.105*
C6	0.3788 (3)	0.2939 (2)	−0.11876 (15)	0.0726 (7)
H61	0.3696	0.2196	−0.1032	0.109*
H62	0.4521	0.2959	−0.1495	0.109*
H63	0.3058	0.3471	−0.1550	0.109*
C7	0.3726 (3)	0.2580 (3)	0.17796 (18)	0.0877 (9)
H71	0.3933	0.3276	0.1630	0.132*
H72	0.4340	0.2012	0.2221	0.132*
H73	0.2909	0.2684	0.1990	0.132*
C8	0.3372 (3)	0.1111 (2)	0.1199 (2)	0.0826 (8)
H81	0.2537	0.1226	0.1380	0.124*
H82	0.3956	0.0536	0.1656	0.124*
H83	0.3406	0.0882	0.0693	0.124*
C9	1.01452 (15)	−0.23266 (13)	0.15743 (10)	0.0348 (3)
C10	1.13192 (17)	−0.22354 (16)	0.20647 (11)	0.0425 (4)
C11	1.20871 (18)	−0.32457 (18)	0.18258 (13)	0.0520 (5)
C12	1.10139 (17)	−0.33522 (15)	0.13192 (12)	0.0424 (4)
C13	1.1754 (2)	−0.1200 (2)	0.16386 (17)	0.0670 (6)
H131	1.2586	−0.1323	0.1883	0.101*
H132	1.1188	−0.0554	0.1738	0.101*
H133	1.1762	−0.1074	0.1028	0.101*
C14	1.1296 (2)	−0.2448 (2)	0.30343 (13)	0.0623 (6)
H141	1.1035	−0.3106	0.3295	0.094*
H142	1.0717	−0.1810	0.3136	0.094*
H143	1.2122	−0.2560	0.3283	0.094*
C15	1.1186 (2)	−0.3129 (2)	0.03568 (14)	0.0623 (6)
H151	1.1399	−0.2438	0.0127	0.093*
H152	1.0419	−0.3068	0.0055	0.093*
H153	1.1850	−0.3739	0.0284	0.093*
C16	1.0748 (3)	−0.44772 (17)	0.16906 (19)	0.0729 (7)
H161	1.1406	−0.5056	0.1574	0.109*
H162	0.9958	−0.4435	0.1428	0.109*
H163	1.0714	−0.4651	0.2304	0.109*
Cl21	0.71636 (4)	0.26896 (4)	0.27609 (3)	0.05166 (13)
Cl22	0.78294 (4)	−0.27841 (4)	0.41765 (3)	0.05102 (12)
S21	0.86092 (4)	0.10730 (4)	0.43601 (3)	0.04429 (12)
S22	0.84084 (5)	−0.01087 (4)	0.38475 (4)	0.05559 (14)
S23	0.65176 (5)	0.00070 (4)	0.38499 (4)	0.05233 (13)
S24	0.63673 (4)	−0.11695 (4)	0.49701 (3)	0.04265 (11)
O21	1.10527 (14)	0.32566 (15)	0.33197 (12)	0.0692 (4)
O22	0.41045 (16)	−0.35990 (16)	0.50155 (14)	0.0829 (6)
C21	0.86012 (15)	0.22684 (13)	0.34193 (10)	0.0335 (3)
C22	0.88989 (16)	0.32241 (14)	0.37163 (11)	0.0388 (4)
C23	1.01325 (17)	0.29567 (15)	0.33082 (12)	0.0431 (4)
C24	0.98270 (17)	0.21408 (16)	0.29156 (12)	0.0426 (4)
C25	0.8050 (2)	0.44140 (16)	0.32573 (17)	0.0616 (6)
H251	0.8398	0.4948	0.3381	0.092*
H252	0.7228	0.4495	0.3457	0.092*
H253	0.7991	0.4548	0.2645	0.092*
C26	0.9064 (2)	0.30321 (19)	0.46888 (13)	0.0551 (5)
H261	0.9651	0.2304	0.4970	0.083*
H262	0.8268	0.3068	0.4924	0.083*
H263	0.9377	0.3604	0.4781	0.083*
C27	0.9598 (3)	0.2629 (3)	0.19300 (14)	0.0734 (7)
H271	0.8985	0.3359	0.1769	0.110*
H272	0.9293	0.2139	0.1712	0.110*
H273	1.0371	0.2698	0.1691	0.110*
C28	1.0834 (2)	0.09960 (19)	0.31916 (19)	0.0715 (7)
H281	1.1611	0.1084	0.2969	0.107*
H282	1.0571	0.0489	0.2968	0.107*
H283	1.0954	0.0696	0.3812	0.107*
C29	0.63905 (15)	−0.23808 (13)	0.46431 (11)	0.0340 (3)
C30	0.51717 (17)	−0.22879 (16)	0.40883 (12)	0.0439 (4)
C31	0.49517 (17)	−0.31893 (16)	0.48724 (14)	0.0470 (4)
C32	0.61360 (16)	−0.33608 (14)	0.54180 (11)	0.0377 (4)
C33	0.4107 (2)	−0.11863 (19)	0.38679 (18)	0.0671 (6)
H331	0.3349	−0.1297	0.3683	0.101*
H332	0.4323	−0.0618	0.3412	0.101*
H333	0.3978	−0.0951	0.4371	0.101*
C34	0.5400 (3)	−0.2676 (3)	0.32983 (17)	0.0788 (8)
H341	0.6042	−0.3389	0.3455	0.118*
H342	0.5665	−0.2130	0.2853	0.118*
H343	0.4636	−0.2753	0.3090	0.118*
C35	0.5875 (2)	−0.31263 (19)	0.62719 (13)	0.0536 (5)
H351	0.5214	−0.2432	0.6167	0.080*
H352	0.6623	−0.3069	0.6521	0.080*
H353	0.5625	−0.3731	0.6664	0.080*
C36	0.7068 (2)	−0.45262 (16)	0.55966 (16)	0.0575 (5)
H361	0.6748	−0.5076	0.5996	0.086*
H362	0.7858	−0.4543	0.5841	0.086*
H363	0.7185	−0.4695	0.5065	0.086*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0469 (3)	0.0473 (2)	0.0673 (3)	−0.0135 (2)	−0.0153 (2)	−0.0240 (2)
Cl2	0.0437 (2)	0.0562 (3)	0.0471 (2)	−0.0174 (2)	0.0174 (2)	−0.0069 (2)
S1	0.0414 (2)	0.0395 (2)	0.0580 (3)	−0.00590 (18)	0.0044 (2)	−0.0260 (2)
S2	0.0424 (3)	0.0353 (2)	0.0712 (3)	−0.00456 (19)	0.0114 (2)	−0.0045 (2)
S3	0.0418 (2)	0.0357 (2)	0.0686 (3)	−0.00658 (19)	0.0008 (2)	−0.0133 (2)
S4	0.0400 (2)	0.0396 (2)	0.0368 (2)	−0.00300 (18)	0.00100 (18)	−0.00131 (17)
O1	0.0365 (9)	0.157 (2)	0.1247 (19)	0.0091 (11)	0.0002 (10)	−0.0116 (17)
O2	0.0406 (8)	0.1137 (16)	0.1145 (16)	0.0145 (9)	−0.0085 (9)	−0.0503 (13)
C1	0.0340 (8)	0.0317 (8)	0.0396 (8)	−0.0075 (6)	−0.0006 (7)	−0.0169 (7)
C2	0.0409 (9)	0.0379 (9)	0.0442 (9)	−0.0079 (7)	−0.0094 (7)	−0.0131 (7)
C3	0.0347 (10)	0.0636 (13)	0.0720 (14)	−0.0055 (9)	−0.0024 (9)	−0.0248 (11)
C4	0.0413 (9)	0.0500 (10)	0.0512 (11)	−0.0082 (8)	0.0108 (8)	−0.0220 (9)
C5	0.0737 (15)	0.0382 (11)	0.0850 (17)	−0.0130 (10)	−0.0269 (13)	−0.0036 (11)
C6	0.0919 (18)	0.0664 (14)	0.0528 (13)	−0.0107 (13)	−0.0253 (12)	−0.0212 (11)
C7	0.0714 (16)	0.135 (3)	0.0709 (16)	−0.0168 (17)	0.0218 (13)	−0.0654 (18)
C8	0.0723 (16)	0.0681 (16)	0.114 (2)	−0.0333 (13)	0.0504 (16)	−0.0277 (15)
C9	0.0327 (8)	0.0341 (8)	0.0308 (7)	−0.0082 (6)	0.0062 (6)	−0.0028 (6)
C10	0.0376 (9)	0.0464 (10)	0.0387 (9)	−0.0125 (7)	−0.0004 (7)	−0.0069 (7)
C11	0.0375 (9)	0.0558 (11)	0.0490 (11)	−0.0018 (8)	0.0033 (8)	−0.0090 (9)
C12	0.0417 (9)	0.0359 (9)	0.0420 (9)	−0.0055 (7)	0.0079 (7)	−0.0077 (7)
C13	0.0575 (13)	0.0668 (14)	0.0740 (15)	−0.0328 (11)	−0.0081 (11)	−0.0057 (12)
C14	0.0646 (14)	0.0743 (15)	0.0437 (11)	−0.0168 (11)	−0.0045 (10)	−0.0165 (10)
C15	0.0666 (14)	0.0651 (13)	0.0503 (11)	−0.0059 (11)	0.0164 (10)	−0.0242 (10)
C16	0.0795 (16)	0.0354 (10)	0.0953 (19)	−0.0125 (10)	0.0229 (14)	−0.0137 (11)
Cl21	0.0417 (2)	0.0611 (3)	0.0467 (2)	−0.0195 (2)	−0.01057 (19)	−0.0061 (2)
Cl22	0.0413 (2)	0.0602 (3)	0.0593 (3)	−0.0160 (2)	0.0225 (2)	−0.0293 (2)
S21	0.0460 (2)	0.0407 (2)	0.0400 (2)	−0.01731 (19)	0.00370 (19)	−0.00060 (18)
S22	0.0479 (3)	0.0388 (2)	0.0826 (4)	−0.0179 (2)	0.0207 (3)	−0.0189 (2)
S23	0.0466 (3)	0.0393 (2)	0.0653 (3)	−0.0165 (2)	0.0033 (2)	−0.0055 (2)
S24	0.0485 (3)	0.0383 (2)	0.0513 (3)	−0.02035 (19)	0.0137 (2)	−0.02189 (19)
O21	0.0495 (8)	0.0782 (11)	0.0864 (11)	−0.0385 (8)	0.0095 (8)	−0.0178 (9)
O22	0.0601 (10)	0.0906 (13)	0.1084 (14)	−0.0508 (10)	0.0003 (10)	−0.0210 (11)
C21	0.0308 (7)	0.0354 (8)	0.0312 (7)	−0.0110 (6)	−0.0009 (6)	−0.0054 (6)
C22	0.0366 (8)	0.0362 (8)	0.0429 (9)	−0.0128 (7)	0.0006 (7)	−0.0101 (7)
C23	0.0371 (9)	0.0423 (9)	0.0436 (9)	−0.0160 (7)	−0.0002 (7)	−0.0013 (7)
C24	0.0381 (9)	0.0477 (10)	0.0413 (9)	−0.0154 (8)	0.0110 (7)	−0.0113 (8)
C25	0.0617 (13)	0.0354 (10)	0.0799 (15)	−0.0083 (9)	−0.0055 (11)	−0.0133 (10)
C26	0.0573 (12)	0.0679 (13)	0.0503 (11)	−0.0235 (10)	0.0036 (9)	−0.0290 (10)
C27	0.0782 (16)	0.109 (2)	0.0406 (11)	−0.0441 (15)	0.0206 (11)	−0.0205 (12)
C28	0.0534 (13)	0.0551 (13)	0.1012 (19)	−0.0112 (10)	0.0349 (13)	−0.0233 (13)
C29	0.0322 (8)	0.0356 (8)	0.0393 (8)	−0.0114 (6)	0.0100 (6)	−0.0183 (7)
C30	0.0386 (9)	0.0501 (10)	0.0470 (10)	−0.0117 (8)	0.0001 (8)	−0.0228 (8)
C31	0.0389 (9)	0.0474 (10)	0.0641 (12)	−0.0190 (8)	0.0055 (9)	−0.0255 (9)
C32	0.0368 (8)	0.0367 (8)	0.0444 (9)	−0.0162 (7)	0.0087 (7)	−0.0150 (7)
C33	0.0448 (11)	0.0580 (13)	0.0910 (17)	−0.0071 (10)	−0.0153 (11)	−0.0211 (12)
C34	0.0703 (16)	0.121 (2)	0.0684 (15)	−0.0312 (15)	0.0041 (12)	−0.0609 (16)
C35	0.0619 (12)	0.0618 (12)	0.0455 (10)	−0.0295 (10)	0.0202 (9)	−0.0193 (9)
C36	0.0548 (12)	0.0375 (10)	0.0741 (14)	−0.0110 (9)	0.0052 (11)	−0.0122 (9)

Geometric parameters (Å, º)

Cl1—C1	1.7799 (16)	Cl21—C21	1.7796 (16)
Cl2—C9	1.7885 (16)	Cl22—C29	1.7863 (16)
S1—C1	1.8131 (16)	S21—C21	1.8176 (16)
S1—S2	2.0341 (7)	S21—S22	2.0361 (7)
S2—S3	2.0680 (7)	S22—S23	2.0681 (7)
S3—S4	2.0332 (7)	S23—S24	2.0336 (7)
S4—C9	1.8174 (16)	S24—C29	1.8172 (16)
O1—C3	1.190 (3)	O21—C23	1.199 (2)
O2—C11	1.200 (2)	O22—C31	1.200 (2)
C1—C2	1.587 (2)	C21—C22	1.588 (2)
C1—C4	1.588 (3)	C21—C24	1.587 (2)
C2—C3	1.518 (3)	C22—C23	1.524 (3)
C2—C6	1.521 (3)	C22—C25	1.524 (3)
C2—C5	1.522 (3)	C22—C26	1.532 (3)
C3—C4	1.511 (3)	C23—C24	1.517 (3)
C4—C7	1.513 (3)	C24—C27	1.528 (3)
C4—C8	1.538 (3)	C24—C28	1.528 (3)
C5—H51	0.9600	C25—H251	0.9600
C5—H52	0.9600	C25—H252	0.9600
C5—H53	0.9600	C25—H253	0.9600
C6—H61	0.9600	C26—H261	0.9600
C6—H62	0.9600	C26—H262	0.9600
C6—H63	0.9600	C26—H263	0.9600
C7—H71	0.9600	C27—H271	0.9600
C7—H72	0.9600	C27—H272	0.9600
C7—H73	0.9600	C27—H273	0.9600
C8—H81	0.9600	C28—H281	0.9600
C8—H82	0.9600	C28—H282	0.9600
C8—H83	0.9600	C28—H283	0.9600
C9—C10	1.588 (2)	C29—C30	1.589 (2)
C9—C12	1.588 (2)	C29—C32	1.587 (2)
C10—C11	1.520 (3)	C30—C31	1.521 (3)
C10—C14	1.522 (3)	C30—C34	1.523 (3)
C10—C13	1.528 (3)	C30—C33	1.525 (3)
C11—C12	1.518 (3)	C31—C32	1.517 (2)
C12—C16	1.520 (3)	C32—C36	1.522 (3)
C12—C15	1.529 (3)	C32—C35	1.529 (3)
C13—H131	0.9600	C33—H331	0.9600
C13—H132	0.9600	C33—H332	0.9600
C13—H133	0.9600	C33—H333	0.9600
C14—H141	0.9600	C34—H341	0.9600
C14—H142	0.9600	C34—H342	0.9600
C14—H143	0.9600	C34—H343	0.9600
C15—H151	0.9600	C35—H351	0.9600
C15—H152	0.9600	C35—H352	0.9600
C15—H153	0.9600	C35—H353	0.9600
C16—H161	0.9600	C36—H361	0.9600
C16—H162	0.9600	C36—H362	0.9600
C16—H163	0.9600	C36—H363	0.9600
C1—S1—S2	103.59 (6)	C21—S21—S22	103.93 (6)
S1—S2—S3	105.29 (3)	S21—S22—S23	105.30 (3)
S4—S3—S2	105.17 (3)	S24—S23—S22	105.29 (3)
C9—S4—S3	103.61 (6)	C29—S24—S23	103.69 (6)
C2—C1—C4	90.73 (13)	C22—C21—C24	90.73 (13)
C2—C1—Cl1	114.49 (11)	C24—C21—Cl21	114.91 (11)
C4—C1—Cl1	114.32 (12)	C22—C21—Cl21	115.54 (11)
C2—C1—S1	111.37 (11)	C24—C21—S21	116.10 (11)
C4—C1—S1	116.46 (12)	C22—C21—S21	109.99 (11)
Cl1—C1—S1	108.69 (9)	Cl21—C21—S21	108.74 (9)
C3—C2—C6	114.36 (18)	C23—C22—C25	112.44 (16)
C3—C2—C5	112.44 (18)	C23—C22—C26	113.98 (15)
C6—C2—C5	109.08 (19)	C25—C22—C26	109.62 (17)
C1—C2—C3	86.31 (14)	C21—C22—C23	86.14 (13)
C6—C2—C1	116.78 (15)	C25—C22—C21	114.97 (15)
C5—C2—C1	116.41 (14)	C26—C22—C21	117.99 (15)
O1—C3—C4	131.5 (2)	O21—C23—C24	131.90 (19)
O1—C3—C2	132.0 (2)	O21—C23—C22	132.05 (19)
C2—C3—C4	96.49 (14)	C22—C23—C24	96.00 (13)
C3—C4—C7	113.43 (19)	C23—C24—C27	111.86 (17)
C3—C4—C8	110.7 (2)	C23—C24—C28	112.30 (17)
C7—C4—C8	111.0 (2)	C27—C24—C28	110.66 (19)
C1—C4—C3	86.48 (14)	C21—C24—C23	86.43 (13)
C7—C4—C1	116.82 (18)	C27—C24—C21	115.46 (16)
C8—C4—C1	116.18 (16)	C28—C24—C21	117.98 (16)
C2—C5—H51	109.5	C22—C25—H251	109.5
C2—C5—H52	109.5	C22—C25—H252	109.5
H51—C5—H52	109.5	H251—C25—H252	109.5
C2—C5—H53	109.5	C22—C25—H253	109.5
H51—C5—H53	109.5	H251—C25—H253	109.5
H52—C5—H53	109.5	H252—C25—H253	109.5
C2—C6—H61	109.5	C22—C26—H261	109.5
C2—C6—H62	109.5	C22—C26—H262	109.5
H61—C6—H62	109.5	H261—C26—H262	109.5
C2—C6—H63	109.5	C22—C26—H263	109.5
H61—C6—H63	109.5	H261—C26—H263	109.5
H62—C6—H63	109.5	H262—C26—H263	109.5
C4—C7—H71	109.5	C24—C27—H271	109.5
C4—C7—H72	109.5	C24—C27—H272	109.5
H71—C7—H72	109.5	H271—C27—H272	109.5
C4—C7—H73	109.5	C24—C27—H273	109.5
H71—C7—H73	109.5	H271—C27—H273	109.5
H72—C7—H73	109.5	H272—C27—H273	109.5
C4—C8—H81	109.5	C24—C28—H281	109.5
C4—C8—H82	109.5	C24—C28—H282	109.5
H81—C8—H82	109.5	H281—C28—H282	109.5
C4—C8—H83	109.5	C24—C28—H283	109.5
H81—C8—H83	109.5	H281—C28—H283	109.5
H82—C8—H83	109.5	H282—C28—H283	109.5
C10—C9—C12	90.97 (13)	C30—C29—C32	90.69 (13)
C12—C9—Cl2	113.88 (12)	C32—C29—Cl22	114.56 (11)
C10—C9—Cl2	113.23 (11)	C30—C29—Cl22	114.38 (11)
C12—C9—S4	112.18 (11)	C32—C29—S24	111.46 (11)
C10—C9—S4	117.55 (12)	C30—C29—S24	116.68 (11)
Cl2—C9—S4	108.35 (8)	Cl22—C29—S24	108.37 (9)
C11—C10—C14	114.11 (16)	C31—C30—C34	112.67 (19)
C11—C10—C13	111.16 (18)	C31—C30—C33	112.08 (18)
C14—C10—C13	110.31 (18)	C34—C30—C33	110.45 (19)
C9—C10—C11	86.27 (14)	C29—C30—C31	86.44 (13)
C14—C10—C9	116.96 (16)	C34—C30—C29	116.14 (16)
C13—C10—C9	116.06 (15)	C33—C30—C29	117.03 (15)
O2—C11—C12	131.9 (2)	O22—C31—C32	132.2 (2)
O2—C11—C10	131.7 (2)	O22—C31—C30	131.61 (19)
C10—C11—C12	96.36 (14)	C30—C31—C32	96.12 (14)
C11—C12—C16	113.43 (18)	C31—C32—C36	112.84 (15)
C11—C12—C15	113.42 (17)	C31—C32—C35	113.31 (16)
C16—C12—C15	109.28 (19)	C36—C32—C35	109.50 (17)
C9—C12—C11	86.32 (14)	C29—C32—C31	86.63 (13)
C16—C12—C9	116.72 (16)	C36—C32—C29	116.09 (15)
C15—C12—C9	116.15 (15)	C35—C32—C29	116.88 (14)
C10—C13—H131	109.5	C30—C33—H331	109.5
C10—C13—H132	109.5	C30—C33—H332	109.5
H131—C13—H132	109.5	H331—C33—H332	109.5
C10—C13—H133	109.5	C30—C33—H333	109.5
H131—C13—H133	109.5	H331—C33—H333	109.5
H132—C13—H133	109.5	H332—C33—H333	109.5
C10—C14—H141	109.5	C30—C34—H341	109.5
C10—C14—H142	109.5	C30—C34—H342	109.5
H141—C14—H142	109.5	H341—C34—H342	109.5
C10—C14—H143	109.5	C30—C34—H343	109.5
H141—C14—H143	109.5	H341—C34—H343	109.5
H142—C14—H143	109.5	H342—C34—H343	109.5
C12—C15—H151	109.5	C32—C35—H351	109.5
C12—C15—H152	109.5	C32—C35—H352	109.5
H151—C15—H152	109.5	H351—C35—H352	109.5
C12—C15—H153	109.5	C32—C35—H353	109.5
H151—C15—H153	109.5	H351—C35—H353	109.5
H152—C15—H153	109.5	H352—C35—H353	109.5
C12—C16—H161	109.5	C32—C36—H361	109.5
C12—C16—H162	109.5	C32—C36—H362	109.5
H161—C16—H162	109.5	H361—C36—H362	109.5
C12—C16—H163	109.5	C32—C36—H363	109.5
H161—C16—H163	109.5	H361—C36—H363	109.5
H162—C16—H163	109.5	H362—C36—H363	109.5
C1—S1—S2—S3	−99.07 (6)	C21—S21—S22—S23	−98.25 (6)
S1—S2—S3—S4	−92.44 (3)	S21—S22—S23—S24	−94.27 (3)
S2—S3—S4—C9	−96.10 (6)	S22—S23—S24—C29	−96.40 (6)
S2—S1—C1—C2	−174.87 (10)	S22—S21—C21—C24	−72.78 (12)
S2—S1—C1—C4	−72.75 (12)	S22—S21—C21—C22	−173.93 (10)
S2—S1—C1—Cl1	58.09 (9)	S22—S21—C21—Cl21	58.64 (9)
C4—C1—C2—C3	0.09 (14)	C24—C21—C22—C23	−6.18 (12)
Cl1—C1—C2—C3	−117.19 (13)	Cl21—C21—C22—C23	−124.41 (12)
S1—C1—C2—C3	119.00 (13)	S21—C21—C22—C23	112.04 (12)
C4—C1—C2—C6	−115.4 (2)	C24—C21—C22—C25	106.81 (18)
Cl1—C1—C2—C6	127.32 (18)	Cl21—C21—C22—C25	−11.4 (2)
S1—C1—C2—C6	3.5 (2)	S21—C21—C22—C25	−134.97 (16)
C4—C1—C2—C5	113.35 (19)	C24—C21—C22—C26	−121.35 (16)
Cl1—C1—C2—C5	−3.9 (2)	Cl21—C21—C22—C26	120.42 (15)
S1—C1—C2—C5	−127.73 (18)	S21—C21—C22—C26	−3.13 (19)
C6—C2—C3—O1	−62.6 (4)	C25—C22—C23—O21	73.5 (3)
C5—C2—C3—O1	62.5 (4)	C26—C22—C23—O21	−52.1 (3)
C1—C2—C3—O1	179.6 (3)	C21—C22—C23—O21	−171.1 (2)
C6—C2—C3—C4	117.70 (18)	C25—C22—C23—C24	−108.95 (17)
C5—C2—C3—C4	−117.19 (17)	C26—C22—C23—C24	125.50 (16)
C1—C2—C3—C4	−0.10 (14)	C21—C22—C23—C24	6.50 (13)
O1—C3—C4—C7	−61.8 (4)	O21—C23—C24—C27	−72.9 (3)
C2—C3—C4—C7	117.9 (2)	C22—C23—C24—C27	109.53 (17)
O1—C3—C4—C8	63.7 (4)	O21—C23—C24—C28	52.2 (3)
C2—C3—C4—C8	−116.61 (18)	C22—C23—C24—C28	−125.35 (17)
O1—C3—C4—C1	−179.6 (3)	O21—C23—C24—C21	171.1 (2)
C2—C3—C4—C1	0.10 (14)	C22—C23—C24—C21	−6.51 (13)
C2—C1—C4—C3	−0.09 (14)	C22—C21—C24—C23	6.21 (12)
Cl1—C1—C4—C3	117.34 (14)	Cl21—C21—C24—C23	124.98 (12)
S1—C1—C4—C3	−114.51 (14)	S21—C21—C24—C23	−106.56 (13)
C2—C1—C4—C7	−114.6 (2)	C22—C21—C24—C27	−106.34 (18)
Cl1—C1—C4—C7	2.8 (2)	Cl21—C21—C24—C27	12.4 (2)
S1—C1—C4—C7	130.95 (19)	S21—C21—C24—C27	140.90 (17)
C2—C1—C4—C8	111.3 (2)	C22—C21—C24—C28	119.61 (19)
Cl1—C1—C4—C8	−131.25 (19)	Cl21—C21—C24—C28	−121.61 (18)
S1—C1—C4—C8	−3.1 (2)	S21—C21—C24—C28	6.8 (2)
S3—S4—C9—C12	−175.16 (11)	S23—S24—C29—C32	−173.96 (10)
S3—S4—C9—C10	−71.66 (13)	S23—S24—C29—C30	−71.72 (13)
S3—S4—C9—Cl2	58.26 (9)	S23—S24—C29—Cl22	59.09 (9)
C12—C9—C10—C11	−1.88 (13)	C32—C29—C30—C31	2.59 (12)
Cl2—C9—C10—C11	114.73 (13)	Cl22—C29—C30—C31	120.10 (13)
S4—C9—C10—C11	−117.65 (13)	S24—C29—C30—C31	−111.96 (13)
C12—C9—C10—C14	−117.10 (18)	C32—C29—C30—C34	−111.0 (2)
Cl2—C9—C10—C14	−0.5 (2)	Cl22—C29—C30—C34	6.5 (2)
S4—C9—C10—C14	127.13 (16)	S24—C29—C30—C34	134.48 (18)
C12—C9—C10—C13	109.89 (18)	C32—C29—C30—C33	115.61 (19)
Cl2—C9—C10—C13	−133.50 (17)	Cl22—C29—C30—C33	−126.88 (18)
S4—C9—C10—C13	−5.9 (2)	S24—C29—C30—C33	1.1 (2)
C14—C10—C11—O2	−59.9 (3)	C34—C30—C31—O22	−67.7 (3)
C13—C10—C11—O2	65.7 (3)	C33—C30—C31—O22	57.6 (3)
C9—C10—C11—O2	−177.8 (3)	C29—C30—C31—O22	175.4 (2)
C14—C10—C11—C12	119.92 (18)	C34—C30—C31—C32	114.17 (18)
C13—C10—C11—C12	−114.56 (17)	C33—C30—C31—C32	−120.51 (16)
C9—C10—C11—C12	1.98 (14)	C29—C30—C31—C32	−2.73 (13)
O2—C11—C12—C16	60.2 (3)	O22—C31—C32—C36	67.7 (3)
C10—C11—C12—C16	−119.57 (18)	C30—C31—C32—C36	−114.22 (17)
O2—C11—C12—C15	−65.2 (3)	O22—C31—C32—C35	−57.5 (3)
C10—C11—C12—C15	114.99 (17)	C30—C31—C32—C35	120.62 (16)
O2—C11—C12—C9	177.8 (3)	O22—C31—C32—C29	−175.4 (2)
C10—C11—C12—C9	−1.98 (14)	C30—C31—C32—C29	2.73 (13)
C10—C9—C12—C11	1.88 (13)	C30—C29—C32—C31	−2.60 (13)
Cl2—C9—C12—C11	−114.16 (13)	Cl22—C29—C32—C31	−119.95 (12)
S4—C9—C12—C11	122.31 (13)	S24—C29—C32—C31	116.56 (12)
C10—C9—C12—C16	116.32 (19)	C30—C29—C32—C36	111.23 (16)
Cl2—C9—C12—C16	0.3 (2)	Cl22—C29—C32—C36	−6.1 (2)
S4—C9—C12—C16	−123.25 (18)	S24—C29—C32—C36	−129.61 (15)
C10—C9—C12—C15	−112.46 (18)	C30—C29—C32—C35	−117.09 (16)
Cl2—C9—C12—C15	131.50 (16)	Cl22—C29—C32—C35	125.56 (15)
S4—C9—C12—C15	8.0 (2)	S24—C29—C32—C35	2.06 (19)

(VIII) 1,6-bis(1-chloro-2,2,4,4-tetramethyl-3-oxocyclobutan-1-yl)hexasulfane

Crystal data

C16H24Cl2O2S6	Dx = 1.436 Mg m^−3
Mr = 511.63	Melting point = 402–404 K
Tetragonal, P41212	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 4abw 2nw	Cell parameters from 40968 reflections
a = 7.1475 (1) Å	θ = 2.0–27.5°
c = 46.3268 (8) Å	µ = 0.81 mm^−1
V = 2366.69 (6) Å^3	T = 160 K
Z = 4	Plate, colourless
F(000) = 1064	0.17 × 0.17 × 0.02 mm

Data collection

Nonius KappaCCD area-detector diffractometer	2715 independent reflections
Radiation source: Nonius FR591 sealed tube generator	1837 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.114
Detector resolution: 9 pixels mm^-1	θmax = 27.5°, θmin = 2.9°
ϕ and ω scans with κ offsets	h = −9→8
Absorption correction: numerical (Coppens et al., 1965)	k = −9→8
Tmin = 0.858, Tmax = 0.944	l = −59→59
25607 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.043	H-atom parameters constrained
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0349P)^2P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max = 0.001
2715 reflections	Δρmax = 0.32 e Å^−3
123 parameters	Δρmin = −0.26 e Å^−3
0 restraints	Absolute structure: Flack (1983), with 987 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.39 (13)

Special details

Experimental. Solvent used: hexane/dichloromethane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.502 (1) Frames collected: 1470 Seconds exposure per frame: 15 Degrees rotation per frame: 0.6 Crystal-Detector distance (mm): 70.0

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
Cl1	0.44896 (12)	0.66274 (11)	0.030910 (17)	0.0413 (2)
S1	0.41877 (11)	1.01411 (11)	0.062849 (17)	0.0328 (2)
S2	0.47779 (11)	1.12866 (11)	0.023553 (18)	0.0384 (2)
S3	0.25816 (12)	1.05754 (13)	−0.002948 (19)	0.0432 (3)
O1	0.8364 (3)	0.6700 (3)	0.11353 (5)	0.0534 (7)
C1	0.5362 (4)	0.7885 (4)	0.06131 (6)	0.0282 (7)
C2	0.7575 (4)	0.7902 (5)	0.06458 (7)	0.0363 (8)
C3	0.7287 (5)	0.7058 (4)	0.09431 (7)	0.0380 (8)
C4	0.5166 (4)	0.6817 (4)	0.09138 (6)	0.0331 (8)
C5	0.8504 (5)	0.9815 (5)	0.06595 (7)	0.0553 (11)
H51	0.7917	1.0562	0.0812	0.083*
H52	0.8354	1.0452	0.0474	0.083*
H53	0.9839	0.9662	0.0702	0.083*
C6	0.8623 (5)	0.6584 (6)	0.04433 (8)	0.0722 (14)
H61	0.9935	0.6498	0.0504	0.108*
H62	0.8558	0.7067	0.0246	0.108*
H63	0.8050	0.5339	0.0451	0.108*
C7	0.4018 (5)	0.7746 (5)	0.11490 (7)	0.0471 (9)
H71	0.2698	0.7769	0.1092	0.071*
H72	0.4462	0.9029	0.1178	0.071*
H73	0.4151	0.7039	0.1329	0.071*
C8	0.4656 (5)	0.4755 (4)	0.08875 (7)	0.0501 (10)
H81	0.4841	0.4136	0.1074	0.075*
H82	0.5456	0.4163	0.0742	0.075*
H83	0.3343	0.4639	0.0829	0.075*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0553 (6)	0.0305 (5)	0.0381 (5)	0.0022 (4)	−0.0099 (4)	−0.0089 (4)
S1	0.0366 (5)	0.0270 (4)	0.0348 (4)	0.0036 (4)	−0.0006 (4)	−0.0023 (4)
S2	0.0416 (5)	0.0326 (5)	0.0408 (5)	−0.0020 (4)	−0.0060 (4)	0.0063 (4)
S3	0.0484 (6)	0.0391 (5)	0.0421 (5)	0.0084 (4)	−0.0122 (4)	−0.0026 (4)
O1	0.0576 (17)	0.0516 (16)	0.0509 (15)	0.0030 (13)	−0.0228 (13)	0.0064 (13)
C1	0.0337 (19)	0.0221 (16)	0.0289 (16)	0.0002 (14)	−0.0008 (15)	−0.0040 (13)
C2	0.0263 (19)	0.043 (2)	0.0393 (19)	0.0077 (16)	−0.0002 (16)	−0.0013 (17)
C3	0.044 (2)	0.0243 (19)	0.045 (2)	0.0043 (16)	−0.0057 (18)	−0.0081 (16)
C4	0.037 (2)	0.0294 (18)	0.0326 (18)	0.0004 (16)	−0.0012 (15)	−0.0008 (14)
C5	0.033 (2)	0.076 (3)	0.057 (2)	−0.010 (2)	−0.0059 (18)	0.020 (2)
C6	0.046 (2)	0.113 (4)	0.057 (3)	0.039 (3)	0.003 (2)	−0.023 (3)
C7	0.053 (2)	0.051 (2)	0.037 (2)	0.0050 (19)	0.0081 (18)	0.0031 (18)
C8	0.070 (3)	0.0317 (19)	0.049 (2)	−0.0071 (19)	−0.005 (2)	0.0101 (17)

Geometric parameters (Å, º)

Cl1—C1	1.783 (3)	C4—C8	1.523 (4)
S1—C1	1.819 (3)	C5—H51	0.9800
S1—S2	2.0402 (11)	C5—H52	0.9800
S2—S3	2.0567 (12)	C5—H53	0.9800
S3—S3^i	2.0461 (18)	C6—H61	0.9800
O1—C3	1.205 (4)	C6—H62	0.9800
C1—C2	1.589 (4)	C6—H63	0.9800
C1—C4	1.595 (4)	C7—H71	0.9800
C2—C3	1.518 (4)	C7—H72	0.9800
C2—C5	1.521 (4)	C7—H73	0.9800
C2—C6	1.526 (4)	C8—H81	0.9800
C3—C4	1.531 (4)	C8—H82	0.9800
C4—C7	1.517 (4)	C8—H83	0.9800
C1—S1—S2	103.03 (10)	C2—C5—H51	109.5
S1—S2—S3	106.00 (5)	C2—C5—H52	109.5
S3^i—S3—S2	106.39 (5)	H51—C5—H52	109.5
C2—C1—C4	90.5 (2)	C2—C5—H53	109.5
C2—C1—Cl1	115.3 (2)	H51—C5—H53	109.5
C4—C1—Cl1	114.7 (2)	H52—C5—H53	109.5
C2—C1—S1	116.6 (2)	C2—C6—H61	109.5
C4—C1—S1	110.5 (2)	C2—C6—H62	109.5
Cl1—C1—S1	108.44 (15)	H61—C6—H62	109.5
C3—C2—C5	112.2 (3)	C2—C6—H63	109.5
C3—C2—C6	112.3 (3)	H61—C6—H63	109.5
C5—C2—C6	111.5 (3)	H62—C6—H63	109.5
C1—C2—C3	87.0 (2)	C4—C7—H71	109.5
C5—C2—C1	116.5 (3)	C4—C7—H72	109.5
C6—C2—C1	115.2 (3)	H71—C7—H72	109.5
O1—C3—C2	132.0 (3)	C4—C7—H73	109.5
O1—C3—C4	132.4 (3)	H71—C7—H73	109.5
C2—C3—C4	95.7 (3)	H72—C7—H73	109.5
C7—C4—C8	110.6 (3)	C4—C8—H81	109.5
C7—C4—C3	115.0 (3)	C4—C8—H82	109.5
C8—C4—C3	110.7 (3)	H81—C8—H82	109.5
C7—C4—C1	117.7 (3)	C4—C8—H83	109.5
C8—C4—C1	114.5 (2)	H81—C8—H83	109.5
C1—C4—C3	86.4 (2)	H82—C8—H83	109.5
C1—S1—S2—S3	92.90 (11)	C5—C2—C3—C4	122.8 (3)
S1—S2—S3—S3^i	86.24 (6)	C6—C2—C3—C4	−110.7 (3)
S2—S3—S3^i—S2^i	83.73 (6)	C1—C2—C3—C4	5.4 (2)
S2—S1—C1—C2	75.0 (2)	O1—C3—C4—C7	55.7 (5)
S2—S1—C1—C4	176.36 (18)	C2—C3—C4—C7	−124.4 (3)
S2—S1—C1—Cl1	−57.13 (16)	O1—C3—C4—C8	−70.5 (4)
C4—C1—C2—C3	−5.2 (2)	C2—C3—C4—C8	109.4 (3)
Cl1—C1—C2—C3	−122.9 (2)	O1—C3—C4—C1	174.7 (4)
S1—C1—C2—C3	108.1 (2)	C2—C3—C4—C1	−5.4 (2)
C4—C1—C2—C5	−118.6 (3)	C2—C1—C4—C7	121.5 (3)
Cl1—C1—C2—C5	123.6 (3)	Cl1—C1—C4—C7	−120.2 (3)
S1—C1—C2—C5	−5.3 (4)	S1—C1—C4—C7	2.8 (4)
C4—C1—C2—C6	108.1 (3)	C2—C1—C4—C8	−106.0 (3)
Cl1—C1—C2—C6	−9.7 (4)	Cl1—C1—C4—C8	12.3 (3)
S1—C1—C2—C6	−138.6 (3)	S1—C1—C4—C8	135.3 (3)
C5—C2—C3—O1	−57.2 (5)	C2—C1—C4—C3	5.1 (2)
C6—C2—C3—O1	69.3 (5)	Cl1—C1—C4—C3	123.4 (2)
C1—C2—C3—O1	−174.7 (4)	S1—C1—C4—C3	−113.7 (2)

Symmetry code: (i) y−1, x+1, −z.