The dimer, trimer and 1,2,4-tri­thiol­ane of adamantane­thione

The mol­ecules of di­spiro­[1,3-dithietane-2,2':4,2''-diadamantane], C₂₀H₂₈S₂, have crystallographic C_i symmetry, as well as local D_2h symmetry, and a planar 1,3-dithietane ring. The mol­ecules of tri­spiro­[1,3,5-tri­thia­ne-2,2':4,2'':6,2'''-triadamantane], C₃₀H₄₂S₃, have approximate C₂ symmetry and the 1,3,5-tri­thia­ne ring has a twist-boat conformation. The C-S-C bond angles within the ring are about 8° larger than observed in most related 1,3,5-tri­thia­ne structures. In di­spiro­[1,2,4-tri­thiol­ane-3,2':5,2''-diadamantane], C₂₀H₂₈S₃, the mol­ecules have local C₂ symmetry and the 1,2,4-tri­thiol­ane ring has a half-chair conformation.

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).

(II) dispiro[1,3-dithietane-2,2':4,2''-diadamantane]

Crystal data

C20H28S2	F(000) = 360
Mr = 332.56	Dx = 1.330 Mg m^−3
Monoclinic, P21/n	Melting point = 578–580 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 6.4567 (1) Å	Cell parameters from 17358 reflections
b = 12.0271 (2) Å	θ = 2.0–30.0°
c = 10.7163 (2) Å	µ = 0.32 mm^−1
β = 93.8719 (5)°	T = 160 K
V = 830.28 (2) Å^3	Prism, colourless
Z = 2	0.25 × 0.25 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer	2410 independent reflections
Radiation source: Nonius FR591 sealed tube generator	2098 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.040
Detector resolution: 9 pixels mm^-1	θmax = 30.0°, θmin = 3.4°
φ and ω scans with κ offsets	h = −9→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −16→16
Tmin = 0.769, Tmax = 0.830	l = −14→15
29949 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.081	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.0363P)^2 + 0.2667P] where P = (Fo^2 + 2Fc^2)/3
2409 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.29 e Å^−3

Special details

Experimental. Solvent used: CH₂Cl₂ / hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.459 (1) Frames collected: 480 Seconds exposure per frame: 10 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
S1	1.20722 (4)	0.00527 (2)	0.02619 (2)	0.01916 (9)
C1	0.97197 (14)	0.05290 (8)	0.09823 (9)	0.01561 (18)
C2	0.94793 (16)	0.00044 (8)	0.22698 (10)	0.0176 (2)
H2	0.9587	−0.0823	0.2208	0.021*
C3	1.12057 (17)	0.04494 (10)	0.31955 (10)	0.0219 (2)
H31	1.1081	0.0107	0.4027	0.026*
H32	1.2579	0.0248	0.2903	0.026*
C4	1.10362 (17)	0.17167 (10)	0.33022 (10)	0.0237 (2)
H4	1.2157	0.2000	0.3910	0.028*
C5	1.12786 (17)	0.22341 (9)	0.20118 (10)	0.0235 (2)
H51	1.2656	0.2041	0.1721	0.028*
H52	1.1188	0.3054	0.2070	0.028*
C6	0.95627 (16)	0.17988 (8)	0.10736 (9)	0.0183 (2)
H6	0.9722	0.2137	0.0233	0.022*
C7	0.73474 (16)	0.03259 (9)	0.27209 (10)	0.0209 (2)
H71	0.6233	0.0043	0.2124	0.025*
H72	0.7169	−0.0016	0.3547	0.025*
C8	0.71837 (16)	0.15952 (9)	0.28226 (10)	0.0218 (2)
H8	0.5798	0.1800	0.3118	0.026*
C9	0.89069 (18)	0.20316 (10)	0.37522 (10)	0.0256 (2)
H91	0.8800	0.2850	0.3822	0.031*
H92	0.8747	0.1707	0.4589	0.031*
C10	0.74219 (17)	0.20997 (9)	0.15248 (10)	0.0219 (2)
H101	0.7278	0.2918	0.1566	0.026*
H102	0.6317	0.1811	0.0926	0.026*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.01337 (13)	0.02701 (15)	0.01717 (14)	−0.00029 (9)	0.00142 (9)	−0.00666 (9)
C1	0.0136 (4)	0.0183 (4)	0.0149 (4)	−0.0001 (3)	0.0010 (3)	−0.0018 (3)
C2	0.0191 (5)	0.0178 (4)	0.0161 (5)	0.0009 (3)	0.0032 (4)	0.0016 (3)
C3	0.0210 (5)	0.0290 (5)	0.0155 (4)	0.0044 (4)	−0.0002 (4)	0.0005 (4)
C4	0.0217 (5)	0.0303 (6)	0.0186 (5)	−0.0005 (4)	−0.0013 (4)	−0.0080 (4)
C5	0.0239 (5)	0.0211 (5)	0.0257 (5)	−0.0050 (4)	0.0024 (4)	−0.0050 (4)
C6	0.0207 (5)	0.0168 (4)	0.0174 (4)	0.0001 (3)	0.0011 (4)	0.0010 (3)
C7	0.0197 (5)	0.0256 (5)	0.0181 (5)	−0.0013 (4)	0.0054 (4)	0.0002 (4)
C8	0.0193 (5)	0.0270 (5)	0.0193 (5)	0.0042 (4)	0.0035 (4)	−0.0048 (4)
C9	0.0268 (5)	0.0308 (6)	0.0192 (5)	0.0023 (4)	0.0019 (4)	−0.0084 (4)
C10	0.0230 (5)	0.0210 (5)	0.0217 (5)	0.0058 (4)	0.0010 (4)	−0.0019 (4)

Geometric parameters (Å, º)

S1—C1	1.8411 (10)	C5—H51	0.99
S1—C1^i	1.8432 (10)	C5—H52	0.99
C1—C6	1.5342 (14)	C6—C10	1.5380 (14)
C1—C2	1.5346 (14)	C6—H6	1.00
C2—C3	1.5374 (14)	C7—C8	1.5346 (15)
C2—C7	1.5388 (14)	C7—H71	0.99
C2—H2	1.00	C7—H72	0.99
C3—C4	1.5330 (16)	C8—C10	1.5346 (15)
C3—H31	0.99	C8—C9	1.5350 (15)
C3—H32	0.99	C8—H8	1.00
C4—C5	1.5340 (16)	C9—H91	0.99
C4—C9	1.5348 (16)	C9—H92	0.99
C4—H4	1.00	C10—H101	0.99
C5—C6	1.5369 (14)	C10—H102	0.99
C1—S1—C1^i	85.76 (4)	C1—C6—C5	109.45 (8)
C6—C1—C2	109.93 (8)	C1—C6—C10	108.60 (8)
C6—C1—S1	113.36 (7)	C5—C6—C10	109.73 (8)
C2—C1—S1	112.67 (7)	C1—C6—H6	109.7
C6—C1—S1^i	112.52 (7)	C5—C6—H6	109.7
C2—C1—S1^i	113.43 (7)	C10—C6—H6	109.7
S1—C1—S1^i	94.24 (4)	C8—C7—C2	109.86 (8)
C1—C2—C3	108.91 (8)	C8—C7—H71	109.7
C1—C2—C7	109.03 (8)	C2—C7—H71	109.7
C3—C2—C7	109.56 (8)	C8—C7—H72	109.7
C1—C2—H2	109.8	C2—C7—H72	109.7
C3—C2—H2	109.8	H71—C7—H72	108.2
C7—C2—H2	109.8	C10—C8—C7	108.50 (8)
C4—C3—C2	110.00 (8)	C10—C8—C9	109.90 (9)
C4—C3—H31	109.7	C7—C8—C9	109.63 (9)
C2—C3—H31	109.7	C10—C8—H8	109.6
C4—C3—H32	109.7	C7—C8—H8	109.6
C2—C3—H32	109.7	C9—C8—H8	109.6
H31—C3—H32	108.2	C4—C9—C8	109.70 (8)
C3—C4—C5	108.90 (9)	C4—C9—H91	109.7
C3—C4—C9	109.80 (9)	C8—C9—H91	109.7
C5—C4—C9	109.34 (9)	C4—C9—H92	109.7
C3—C4—H4	109.6	C8—C9—H92	109.7
C5—C4—H4	109.6	H91—C9—H92	108.2
C9—C4—H4	109.6	C8—C10—C6	109.82 (8)
C4—C5—C6	109.79 (9)	C8—C10—H101	109.7
C4—C5—H51	109.7	C6—C10—H101	109.7
C6—C5—H51	109.7	C8—C10—H102	109.7
C4—C5—H52	109.7	C6—C10—H102	109.7
C6—C5—H52	109.7	H101—C10—H102	108.2
H51—C5—H52	108.2
C1^i—S1—C1—C6	−116.76 (8)	C2—C1—C6—C10	−60.24 (10)
C1^i—S1—C1—C2	117.59 (8)	S1—C1—C6—C10	172.66 (7)
C1^i—S1—C1—S1^i	0.0	S1^i—C1—C6—C10	67.22 (9)
C6—C1—C2—C3	−59.61 (10)	C4—C5—C6—C1	−59.68 (11)
S1—C1—C2—C3	67.87 (9)	C4—C5—C6—C10	59.40 (11)
S1^i—C1—C2—C3	173.45 (7)	C1—C2—C7—C8	−60.02 (11)
C6—C1—C2—C7	59.90 (10)	C3—C2—C7—C8	59.08 (11)
S1—C1—C2—C7	−172.62 (7)	C2—C7—C8—C10	60.47 (11)
S1^i—C1—C2—C7	−67.05 (9)	C2—C7—C8—C9	−59.56 (11)
C1—C2—C3—C4	60.30 (11)	C3—C4—C9—C8	−59.44 (12)
C7—C2—C3—C4	−58.88 (11)	C5—C4—C9—C8	59.98 (12)
C2—C3—C4—C5	−60.52 (11)	C10—C8—C9—C4	−59.55 (12)
C2—C3—C4—C9	59.18 (11)	C7—C8—C9—C4	59.62 (12)
C3—C4—C5—C6	59.99 (11)	C7—C8—C10—C6	−61.06 (11)
C9—C4—C5—C6	−59.99 (11)	C9—C8—C10—C6	58.79 (11)
C2—C1—C6—C5	59.54 (11)	C1—C6—C10—C8	60.95 (11)
S1—C1—C6—C5	−67.56 (9)	C5—C6—C10—C8	−58.65 (11)
S1^i—C1—C6—C5	−173.00 (7)

Symmetry code: (i) −x+2, −y, −z.

(III) trispiro[1,3,5-trithiane-2,2':4,2'':6,2'''-triadamantane]

Crystal data

C30H42S3	Z = 2
Mr = 498.84	F(000) = 540
Triclinic, P1	Dx = 1.366 Mg m^−3
Hall symbol: -P 1	Melting point = 618.9–619.4 K
a = 6.6436 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3102 (2) Å	Cell parameters from 47672 reflections
c = 15.6057 (2) Å	θ = 2.0–30.0°
α = 77.0671 (5)°	µ = 0.32 mm^−1
β = 86.7263 (6)°	T = 160 K
γ = 77.1671 (7)°	Needle, colourless
V = 1212.81 (3) Å^3	0.25 × 0.12 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	7114 independent reflections
Radiation source: Nonius FR591 sealed tube generator	5854 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.053
Detector resolution: 9 pixels mm^-1	θmax = 30.0°, θmin = 2.7°
φ and ω scans with κ offsets	h = −9→9
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −17→17
Tmin = 0.914, Tmax = 0.970	l = −21→21
50920 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.094	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0438P)^2 + 0.4675P] where P = (Fo^2 + 2Fc^2)/3
7113 reflections	(Δ/σ)max = 0.001
298 parameters	Δρmax = 0.42 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. Solvent used: CH₂Cl₂ / hexane Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.648 (1) Frames collected: 639 Seconds exposure per frame: 40 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
S1	0.33045 (5)	0.84430 (3)	0.14323 (2)	0.01722 (8)
S3	0.14588 (5)	0.91645 (2)	0.30841 (2)	0.01416 (7)
S5	0.40169 (5)	0.67727 (3)	0.31857 (2)	0.01529 (8)
C2	0.32622 (19)	0.94283 (10)	0.21744 (8)	0.0138 (2)
C4	0.25224 (18)	0.77853 (10)	0.38106 (8)	0.0130 (2)
C6	0.28793 (19)	0.70647 (10)	0.20973 (8)	0.0143 (2)
C7	0.54635 (18)	0.94454 (10)	0.24414 (8)	0.0146 (2)
H7	0.6125	0.8677	0.2793	0.017*
C8	0.67667 (19)	0.97474 (11)	0.16111 (8)	0.0170 (2)
H81	0.8188	0.9730	0.1782	0.020*
H82	0.6844	0.9174	0.1248	0.020*
C9	0.5812 (2)	1.09367 (11)	0.10720 (8)	0.0174 (2)
H9	0.6669	1.1119	0.0533	0.021*
C10	0.3618 (2)	1.09511 (11)	0.08056 (8)	0.0173 (2)
H101	0.3672	1.0393	0.0432	0.021*
H102	0.2986	1.1718	0.0460	0.021*
C11	0.22899 (19)	1.06482 (10)	0.16307 (8)	0.0150 (2)
H11	0.0861	1.0666	0.1450	0.018*
C12	0.5372 (2)	1.03528 (11)	0.29914 (8)	0.0176 (2)
H121	0.4545	1.0172	0.3532	0.021*
H122	0.6785	1.0344	0.3168	0.021*
C13	0.4398 (2)	1.15423 (11)	0.24546 (9)	0.0191 (3)
H13	0.4329	1.2121	0.2821	0.023*
C14	0.5722 (2)	1.18326 (11)	0.16304 (9)	0.0206 (3)
H14A	0.7134	1.1831	0.1804	0.025*
H14B	0.5113	1.2603	0.1284	0.025*
C15	0.2211 (2)	1.15529 (10)	0.21807 (9)	0.0179 (2)
H151	0.1582	1.2318	0.1831	0.021*
H152	0.1343	1.1389	0.2711	0.021*
C16	0.40298 (19)	0.78625 (10)	0.45122 (8)	0.0149 (2)
H16	0.5268	0.8117	0.4211	0.018*
C17	0.2959 (2)	0.87145 (11)	0.50665 (8)	0.0173 (2)
H171	0.3939	0.8766	0.5503	0.021*
H172	0.2521	0.9481	0.4681	0.021*
C18	0.1069 (2)	0.83313 (11)	0.55438 (8)	0.0180 (2)
H18	0.0370	0.8899	0.5894	0.022*
C19	−0.04377 (19)	0.82466 (11)	0.48637 (8)	0.0177 (2)
H191	−0.0909	0.9005	0.4472	0.021*
H192	−0.1662	0.8001	0.5168	0.021*
C20	0.06283 (19)	0.73806 (10)	0.43120 (8)	0.0157 (2)
H20	−0.0373	0.7321	0.3879	0.019*
C21	0.4721 (2)	0.66821 (11)	0.51374 (8)	0.0184 (2)
H211	0.5425	0.6118	0.4795	0.022*
H212	0.5710	0.6731	0.5571	0.022*
C22	0.2837 (2)	0.62903 (11)	0.56202 (9)	0.0193 (3)
H22	0.3293	0.5525	0.6020	0.023*
C23	0.1763 (2)	0.71587 (11)	0.61598 (9)	0.0210 (3)
H231	0.0551	0.6908	0.6473	0.025*
H232	0.2727	0.7210	0.6603	0.025*
C24	0.1327 (2)	0.62131 (11)	0.49384 (9)	0.0186 (3)
H241	0.0109	0.5959	0.5243	0.022*
H242	0.2007	0.5643	0.4597	0.022*
C25	0.05998 (19)	0.69626 (10)	0.20793 (8)	0.0164 (2)
H25	−0.0297	0.7549	0.2366	0.020*
C26	−0.0078 (2)	0.71553 (11)	0.11161 (9)	0.0203 (3)
H261	−0.1547	0.7114	0.1103	0.024*
H262	0.0060	0.7925	0.0792	0.024*
C27	0.1255 (2)	0.62486 (12)	0.06685 (9)	0.0228 (3)
H27	0.0814	0.6389	0.0044	0.027*
C28	0.3524 (2)	0.63218 (11)	0.06927 (9)	0.0208 (3)
H281	0.3700	0.7083	0.0365	0.025*
H282	0.4396	0.5739	0.0406	0.025*
C29	0.4211 (2)	0.61248 (11)	0.16511 (9)	0.0175 (2)
H29	0.5698	0.6162	0.1660	0.021*
C30	0.0354 (2)	0.57628 (11)	0.25662 (9)	0.0209 (3)
H301	0.0788	0.5620	0.3185	0.025*
H302	−0.1115	0.5717	0.2565	0.025*
C31	0.1676 (2)	0.48524 (11)	0.21170 (10)	0.0231 (3)
H31	0.1511	0.4078	0.2440	0.028*
C32	0.0990 (2)	0.50603 (12)	0.11595 (10)	0.0262 (3)
H321	0.1835	0.4471	0.0871	0.031*
H322	−0.0474	0.5010	0.1144	0.031*
C33	0.3946 (2)	0.49270 (11)	0.21351 (9)	0.0212 (3)
H331	0.4814	0.4344	0.1848	0.025*
H332	0.4401	0.4774	0.2752	0.025*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.02598 (17)	0.01429 (14)	0.01360 (15)	−0.00746 (12)	0.00110 (11)	−0.00484 (11)
S3	0.01512 (14)	0.01247 (14)	0.01369 (14)	−0.00127 (10)	0.00023 (10)	−0.00209 (11)
S5	0.01701 (15)	0.01364 (14)	0.01473 (15)	0.00014 (11)	−0.00210 (11)	−0.00499 (11)
C2	0.0170 (6)	0.0122 (5)	0.0125 (5)	−0.0029 (4)	0.0005 (4)	−0.0038 (4)
C4	0.0152 (5)	0.0112 (5)	0.0127 (5)	−0.0019 (4)	−0.0006 (4)	−0.0033 (4)
C6	0.0185 (6)	0.0118 (5)	0.0128 (5)	−0.0032 (4)	−0.0008 (4)	−0.0028 (4)
C7	0.0149 (6)	0.0139 (5)	0.0147 (6)	−0.0028 (4)	−0.0004 (4)	−0.0029 (4)
C8	0.0165 (6)	0.0172 (6)	0.0173 (6)	−0.0038 (5)	0.0013 (5)	−0.0038 (5)
C9	0.0210 (6)	0.0156 (6)	0.0155 (6)	−0.0057 (5)	0.0028 (5)	−0.0025 (5)
C10	0.0217 (6)	0.0143 (6)	0.0151 (6)	−0.0033 (5)	−0.0007 (5)	−0.0018 (5)
C11	0.0166 (6)	0.0126 (5)	0.0152 (6)	−0.0022 (4)	−0.0012 (4)	−0.0024 (4)
C12	0.0204 (6)	0.0181 (6)	0.0162 (6)	−0.0065 (5)	−0.0016 (5)	−0.0052 (5)
C13	0.0253 (7)	0.0145 (6)	0.0198 (6)	−0.0053 (5)	0.0004 (5)	−0.0075 (5)
C14	0.0252 (7)	0.0165 (6)	0.0216 (7)	−0.0085 (5)	0.0010 (5)	−0.0035 (5)
C15	0.0221 (6)	0.0121 (5)	0.0183 (6)	−0.0008 (5)	0.0015 (5)	−0.0040 (5)
C16	0.0168 (6)	0.0150 (5)	0.0134 (6)	−0.0033 (4)	−0.0021 (4)	−0.0038 (4)
C17	0.0224 (6)	0.0156 (6)	0.0150 (6)	−0.0049 (5)	−0.0001 (5)	−0.0051 (5)
C18	0.0231 (6)	0.0164 (6)	0.0148 (6)	−0.0036 (5)	0.0024 (5)	−0.0053 (5)
C19	0.0171 (6)	0.0181 (6)	0.0172 (6)	−0.0034 (5)	0.0031 (5)	−0.0036 (5)
C20	0.0168 (6)	0.0148 (5)	0.0156 (6)	−0.0039 (4)	0.0002 (4)	−0.0032 (5)
C21	0.0203 (6)	0.0167 (6)	0.0163 (6)	0.0000 (5)	−0.0041 (5)	−0.0027 (5)
C22	0.0270 (7)	0.0147 (6)	0.0150 (6)	−0.0043 (5)	−0.0022 (5)	−0.0001 (5)
C23	0.0275 (7)	0.0201 (6)	0.0154 (6)	−0.0061 (5)	0.0009 (5)	−0.0027 (5)
C24	0.0247 (6)	0.0140 (6)	0.0177 (6)	−0.0068 (5)	−0.0001 (5)	−0.0021 (5)
C25	0.0174 (6)	0.0146 (6)	0.0179 (6)	−0.0033 (4)	−0.0016 (4)	−0.0046 (5)
C26	0.0214 (6)	0.0201 (6)	0.0206 (6)	−0.0049 (5)	−0.0049 (5)	−0.0052 (5)
C27	0.0312 (7)	0.0203 (6)	0.0193 (6)	−0.0057 (5)	−0.0053 (5)	−0.0077 (5)
C28	0.0286 (7)	0.0183 (6)	0.0177 (6)	−0.0048 (5)	0.0015 (5)	−0.0090 (5)
C29	0.0190 (6)	0.0149 (6)	0.0192 (6)	−0.0014 (5)	−0.0003 (5)	−0.0073 (5)
C30	0.0226 (6)	0.0195 (6)	0.0226 (7)	−0.0089 (5)	0.0000 (5)	−0.0047 (5)
C31	0.0322 (7)	0.0146 (6)	0.0247 (7)	−0.0088 (5)	−0.0013 (6)	−0.0051 (5)
C32	0.0339 (8)	0.0209 (7)	0.0286 (8)	−0.0091 (6)	−0.0038 (6)	−0.0115 (6)
C33	0.0271 (7)	0.0128 (6)	0.0227 (7)	0.0000 (5)	−0.0026 (5)	−0.0060 (5)

Geometric parameters (Å, º)

S1—C2	1.8501 (12)	C18—C23	1.5343 (18)
S1—C6	1.8511 (12)	C18—C19	1.5353 (18)
S3—C2	1.8245 (12)	C18—H18	1.00
S3—C4	1.8341 (12)	C19—C20	1.5444 (17)
S5—C6	1.8270 (13)	C19—H191	0.99
S5—C4	1.8370 (12)	C19—H192	0.99
C2—C7	1.5492 (17)	C20—C24	1.5373 (17)
C2—C11	1.5665 (17)	C20—H20	1.00
C4—C16	1.5572 (17)	C21—C22	1.5373 (19)
C4—C20	1.5606 (17)	C21—H211	0.99
C6—C25	1.5495 (17)	C21—H212	0.99
C6—C29	1.5627 (17)	C22—C23	1.5351 (19)
C7—C8	1.5381 (17)	C22—C24	1.5354 (18)
C7—C12	1.5432 (17)	C22—H22	1.00
C7—H7	1.00	C23—H231	0.99
C8—C9	1.5331 (17)	C23—H232	0.99
C8—H81	0.99	C24—H241	0.99
C8—H82	0.99	C24—H242	0.99
C9—C10	1.5339 (18)	C25—C30	1.5416 (17)
C9—C14	1.5408 (18)	C25—C26	1.5456 (18)
C9—H9	1.00	C25—H25	1.00
C10—C11	1.5416 (17)	C26—C27	1.5353 (19)
C10—H101	0.99	C26—H261	0.99
C10—H102	0.99	C26—H262	0.99
C11—C15	1.5415 (17)	C27—C28	1.534 (2)
C11—H11	1.00	C27—C32	1.535 (2)
C12—C13	1.5352 (18)	C27—H27	1.00
C12—H121	0.99	C28—C29	1.5396 (18)
C12—H122	0.99	C28—H281	0.99
C13—C15	1.5342 (18)	C28—H282	0.99
C13—C14	1.5367 (19)	C29—C33	1.5419 (18)
C13—H13	1.00	C29—H29	1.00
C14—H14A	0.99	C30—C31	1.5370 (19)
C14—H14B	0.99	C30—H301	0.99
C15—H151	0.99	C30—H302	0.99
C15—H152	0.99	C31—C33	1.533 (2)
C16—C17	1.5358 (17)	C31—C32	1.536 (2)
C16—C21	1.5474 (17)	C31—H31	1.00
C16—H16	1.00	C32—H321	0.99
C17—C18	1.5337 (18)	C32—H322	0.99
C17—H171	0.99	C33—H331	0.99
C17—H172	0.99	C33—H332	0.99
C2—S1—C6	108.59 (5)	C19—C18—H18	109.6
C2—S3—C4	108.70 (5)	C18—C19—C20	110.14 (10)
C6—S5—C4	108.91 (5)	C18—C19—H191	109.6
C7—C2—C11	107.56 (9)	C20—C19—H191	109.6
C7—C2—S3	115.40 (8)	C18—C19—H192	109.6
C11—C2—S3	104.73 (8)	C20—C19—H192	109.6
C7—C2—S1	112.04 (8)	H191—C19—H192	108.1
C11—C2—S1	105.84 (8)	C24—C20—C19	108.26 (10)
S3—C2—S1	110.51 (6)	C24—C20—C4	110.41 (10)
C16—C4—C20	107.42 (10)	C19—C20—C4	109.67 (10)
C16—C4—S3	113.57 (8)	C24—C20—H20	109.5
C20—C4—S3	105.53 (8)	C19—C20—H20	109.5
C16—C4—S5	105.58 (8)	C4—C20—H20	109.5
C20—C4—S5	113.60 (8)	C22—C21—C16	110.06 (10)
S3—C4—S5	111.26 (6)	C22—C21—H211	109.6
C25—C6—C29	107.42 (10)	C16—C21—H211	109.6
C25—C6—S5	116.00 (9)	C22—C21—H212	109.6
C29—C6—S5	104.00 (8)	C16—C21—H212	109.6
C25—C6—S1	112.18 (8)	H211—C21—H212	108.2
C29—C6—S1	105.83 (8)	C23—C22—C24	109.38 (11)
S5—C6—S1	110.52 (6)	C23—C22—C21	109.55 (11)
C8—C7—C12	108.29 (10)	C24—C22—C21	108.91 (11)
C8—C7—C2	109.62 (10)	C23—C22—H22	109.7
C12—C7—C2	110.41 (10)	C24—C22—H22	109.7
C8—C7—H7	109.5	C21—C22—H22	109.7
C12—C7—H7	109.5	C18—C23—C22	109.43 (11)
C2—C7—H7	109.5	C18—C23—H231	109.8
C9—C8—C7	110.48 (10)	C22—C23—H231	109.8
C9—C8—H81	109.6	C18—C23—H232	109.8
C7—C8—H81	109.6	C22—C23—H232	109.8
C9—C8—H82	109.6	H231—C23—H232	108.2
C7—C8—H82	109.6	C22—C24—C20	110.37 (10)
H81—C8—H82	108.1	C22—C24—H241	109.6
C8—C9—C10	109.09 (10)	C20—C24—H241	109.6
C8—C9—C14	109.64 (11)	C22—C24—H242	109.6
C10—C9—C14	109.35 (10)	C20—C24—H242	109.6
C8—C9—H9	109.6	H241—C24—H242	108.1
C10—C9—H9	109.6	C30—C25—C26	108.30 (10)
C14—C9—H9	109.6	C30—C25—C6	110.47 (10)
C9—C10—C11	110.16 (10)	C26—C25—C6	109.49 (10)
C9—C10—H101	109.6	C30—C25—H25	109.5
C11—C10—H101	109.6	C26—C25—H25	109.5
C9—C10—H102	109.6	C6—C25—H25	109.5
C11—C10—H102	109.6	C27—C26—C25	110.34 (11)
H101—C10—H102	108.1	C27—C26—H261	109.6
C15—C11—C10	107.75 (10)	C25—C26—H261	109.6
C15—C11—C2	110.58 (10)	C27—C26—H262	109.6
C10—C11—C2	109.96 (10)	C25—C26—H262	109.6
C15—C11—H11	109.5	H261—C26—H262	108.1
C10—C11—H11	109.5	C28—C27—C32	109.68 (12)
C2—C11—H11	109.5	C28—C27—C26	109.11 (11)
C13—C12—C7	110.21 (10)	C32—C27—C26	109.35 (12)
C13—C12—H121	109.6	C28—C27—H27	109.6
C7—C12—H121	109.6	C32—C27—H27	109.6
C13—C12—H122	109.6	C26—C27—H27	109.6
C7—C12—H122	109.6	C27—C28—C29	110.02 (11)
H121—C12—H122	108.1	C27—C28—H281	109.7
C15—C13—C12	109.51 (10)	C29—C28—H281	109.7
C15—C13—C14	109.57 (11)	C27—C28—H282	109.7
C12—C13—C14	109.37 (11)	C29—C28—H282	109.7
C15—C13—H13	109.5	H281—C28—H282	108.2
C12—C13—H13	109.5	C28—C29—C33	108.08 (10)
C14—C13—H13	109.5	C28—C29—C6	109.77 (10)
C13—C14—C9	108.93 (10)	C33—C29—C6	110.88 (10)
C13—C14—H14A	109.9	C28—C29—H29	109.4
C9—C14—H14A	109.9	C33—C29—H29	109.4
C13—C14—H14B	109.9	C6—C29—H29	109.4
C9—C14—H14B	109.9	C31—C30—C25	110.18 (11)
H14A—C14—H14B	108.3	C31—C30—H301	109.6
C13—C15—C11	110.01 (10)	C25—C30—H301	109.6
C13—C15—H151	109.7	C31—C30—H302	109.6
C11—C15—H151	109.7	C25—C30—H302	109.6
C13—C15—H152	109.7	H301—C30—H302	108.1
C11—C15—H152	109.7	C33—C31—C32	109.53 (12)
H151—C15—H152	108.2	C33—C31—C30	108.90 (11)
C17—C16—C21	108.12 (10)	C32—C31—C30	109.86 (12)
C17—C16—C4	110.38 (10)	C33—C31—H31	109.5
C21—C16—C4	110.03 (10)	C32—C31—H31	109.5
C17—C16—H16	109.4	C30—C31—H31	109.5
C21—C16—H16	109.4	C27—C32—C31	109.14 (11)
C4—C16—H16	109.4	C27—C32—H321	109.9
C18—C17—C16	110.27 (10)	C31—C32—H321	109.9
C18—C17—H171	109.6	C27—C32—H322	109.9
C16—C17—H171	109.6	C31—C32—H322	109.9
C18—C17—H172	109.6	H321—C32—H322	108.3
C16—C17—H172	109.6	C31—C33—C29	109.95 (11)
H171—C17—H172	108.1	C31—C33—H331	109.7
C17—C18—C23	109.38 (11)	C29—C33—H331	109.7
C17—C18—C19	109.28 (10)	C31—C33—H332	109.7
C23—C18—C19	109.43 (11)	C29—C33—H332	109.7
C17—C18—H18	109.6	H331—C33—H332	108.2
C23—C18—H18	109.6
C4—S3—C2—C7	−58.48 (10)	C4—C16—C17—C18	60.27 (13)
C4—S3—C2—C11	−176.52 (8)	C16—C17—C18—C23	60.84 (13)
C4—S3—C2—S1	69.91 (7)	C16—C17—C18—C19	−58.94 (13)
C6—S1—C2—C7	96.82 (9)	C17—C18—C19—C20	59.40 (13)
C6—S1—C2—C11	−146.24 (8)	C23—C18—C19—C20	−60.35 (13)
C6—S1—C2—S3	−33.38 (8)	C18—C19—C20—C24	59.64 (13)
C2—S3—C4—C16	85.79 (9)	C18—C19—C20—C4	−60.89 (13)
C2—S3—C4—C20	−156.81 (8)	C16—C4—C20—C24	−59.31 (12)
C2—S3—C4—S5	−33.16 (8)	S3—C4—C20—C24	179.21 (8)
C6—S5—C4—C16	−155.72 (8)	S5—C4—C20—C24	57.06 (12)
C6—S5—C4—C20	86.83 (9)	C16—C4—C20—C19	59.90 (12)
C6—S5—C4—S3	−32.09 (8)	S3—C4—C20—C19	−61.58 (11)
C4—S5—C6—C25	−59.89 (10)	S5—C4—C20—C19	176.27 (8)
C4—S5—C6—C29	−177.59 (8)	C17—C16—C21—C22	59.68 (13)
C4—S5—C6—S1	69.23 (7)	C4—C16—C21—C22	−60.94 (13)
C2—S1—C6—C25	97.88 (9)	C16—C21—C22—C23	−60.02 (13)
C2—S1—C6—C29	−145.27 (8)	C16—C21—C22—C24	59.58 (13)
C2—S1—C6—S5	−33.27 (8)	C17—C18—C23—C22	−59.78 (14)
C11—C2—C7—C8	−60.13 (12)	C19—C18—C23—C22	59.90 (14)
S3—C2—C7—C8	−176.59 (8)	C24—C22—C23—C18	−59.74 (14)
S1—C2—C7—C8	55.77 (11)	C21—C22—C23—C18	59.57 (14)
C11—C2—C7—C12	59.08 (12)	C23—C22—C24—C20	60.31 (14)
S3—C2—C7—C12	−57.37 (12)	C21—C22—C24—C20	−59.39 (13)
S1—C2—C7—C12	174.99 (8)	C19—C20—C24—C22	−59.65 (13)
C12—C7—C8—C9	−59.21 (13)	C4—C20—C24—C22	60.41 (13)
C2—C7—C8—C9	61.30 (13)	C29—C6—C25—C30	58.73 (13)
C7—C8—C9—C10	−59.62 (13)	S5—C6—C25—C30	−57.06 (12)
C7—C8—C9—C14	60.11 (13)	S1—C6—C25—C30	174.62 (8)
C8—C9—C10—C11	58.91 (13)	C29—C6—C25—C26	−60.45 (12)
C14—C9—C10—C11	−60.99 (13)	S5—C6—C25—C26	−176.25 (8)
C9—C10—C11—C15	60.53 (13)	S1—C6—C25—C26	55.44 (12)
C9—C10—C11—C2	−60.06 (13)	C30—C25—C26—C27	−59.57 (14)
C7—C2—C11—C15	−59.03 (12)	C6—C25—C26—C27	60.96 (13)
S3—C2—C11—C15	64.23 (11)	C25—C26—C27—C28	−59.28 (14)
S1—C2—C11—C15	−178.95 (8)	C25—C26—C27—C32	60.69 (14)
C7—C2—C11—C10	59.85 (12)	C32—C27—C28—C29	−60.54 (14)
S3—C2—C11—C10	−176.90 (8)	C26—C27—C28—C29	59.22 (14)
S1—C2—C11—C10	−60.07 (11)	C27—C28—C29—C33	60.14 (13)
C8—C7—C12—C13	59.58 (13)	C27—C28—C29—C6	−60.92 (13)
C2—C7—C12—C13	−60.44 (13)	C25—C6—C29—C28	60.77 (13)
C7—C12—C13—C15	59.20 (13)	S5—C6—C29—C28	−175.75 (9)
C7—C12—C13—C14	−60.88 (13)	S1—C6—C29—C28	−59.24 (11)
C15—C13—C14—C9	−59.85 (13)	C25—C6—C29—C33	−58.58 (13)
C12—C13—C14—C9	60.19 (14)	S5—C6—C29—C33	64.90 (11)
C8—C9—C14—C13	−59.82 (14)	S1—C6—C29—C33	−178.60 (9)
C10—C9—C14—C13	59.75 (14)	C26—C25—C30—C31	59.00 (14)
C12—C13—C15—C11	−58.92 (13)	C6—C25—C30—C31	−60.91 (14)
C14—C13—C15—C11	61.04 (13)	C25—C30—C31—C33	59.94 (14)
C10—C11—C15—C13	−60.41 (13)	C25—C30—C31—C32	−60.02 (14)
C2—C11—C15—C13	59.80 (13)	C28—C27—C32—C31	59.58 (15)
C20—C4—C16—C17	−59.80 (12)	C26—C27—C32—C31	−60.04 (15)
S3—C4—C16—C17	56.50 (12)	C33—C31—C32—C27	−59.70 (15)
S5—C4—C16—C17	178.66 (8)	C30—C31—C32—C27	59.88 (15)
C20—C4—C16—C21	59.45 (12)	C32—C31—C33—C29	60.77 (14)
S3—C4—C16—C21	175.75 (8)	C30—C31—C33—C29	−59.40 (14)
S5—C4—C16—C21	−62.09 (11)	C28—C29—C33—C31	−60.30 (14)
C21—C16—C17—C18	−60.14 (13)	C6—C29—C33—C31	60.06 (14)

(IV) dispiro[1,2,4-trithiolane-3,2':5,2''-diadamantane]

Crystal data

C20H28S3	F(000) = 784
Mr = 364.62	Dx = 1.359 Mg m^−3
Monoclinic, P21/c	Melting point = 468.4–469.7 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 13.3264 (2) Å	Cell parameters from 5453 reflections
b = 11.5166 (1) Å	θ = 2.0–30.0°
c = 12.9233 (1) Å	µ = 0.41 mm^−1
β = 116.0645 (5)°	T = 160 K
V = 1781.69 (3) Å^3	Prism, colourless
Z = 4	0.20 × 0.15 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer	4190 reflections with I > 2σ(I)
Radiation source: Nonius FR591 sealed tube generator	Rint = 0.044
Horizontally mounted graphite crystal monochromator	θmax = 30.1°, θmin = 3.2°
Detector resolution: 9 pixels mm^-1	h = −18→16
φ and ω scans with κ offsets	k = −16→0
50637 measured reflections	l = 0→18
5220 independent 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.097	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0467P)^2 + 0.6782P] where P = (Fo^2 + 2Fc^2)/3
5217 reflections	(Δ/σ)max = 0.001
208 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.36 e Å^−3

Special details

Experimental. Solvent used: CDCl₃ / CH₂Cl₂ / CH₃OH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.464 (1) Frames collected: 378 Seconds exposure per frame: 40 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.

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

11.9249 (0.0047) x - 3.1084 (0.0068) y - 0.9533 (0.0103) z = 1.8634 (0.0086)

* 0.0000 (0.0000) C3 * 0.0000 (0.0000) S4 * 0.0000 (0.0000) C5 0.6302 (0.0022) S1 - 0.5117 (0.0022) S2

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	0.27916 (3)	−0.07394 (3)	1.11734 (3)	0.02496 (9)
S2	0.22661 (3)	0.08375 (3)	1.14365 (3)	0.02574 (9)
S4	0.25221 (3)	0.08339 (3)	0.92828 (3)	0.02134 (9)
C3	0.28476 (10)	0.16741 (11)	1.06155 (10)	0.0181 (2)
C5	0.21634 (10)	−0.06389 (10)	0.95980 (10)	0.0170 (2)
C6	0.22346 (10)	0.28561 (11)	1.02981 (11)	0.0216 (3)
H6	0.1412	0.2725	0.9863	0.026*
C7	0.24871 (12)	0.35460 (13)	1.14089 (12)	0.0275 (3)
H71	0.2088	0.4299	1.1210	0.033*
H72	0.2220	0.3105	1.1898	0.033*
C8	0.37486 (12)	0.37587 (12)	1.20737 (12)	0.0261 (3)
H8	0.3906	0.4203	1.2794	0.031*
C9	0.43549 (12)	0.25869 (12)	1.23885 (11)	0.0254 (3)
H91	0.4099	0.2142	1.2884	0.030*
H92	0.5169	0.2716	1.2825	0.030*
C10	0.41143 (10)	0.18914 (11)	1.12892 (11)	0.0207 (2)
H10	0.4519	0.1132	1.1498	0.025*
C11	0.26517 (11)	0.35577 (12)	0.95557 (11)	0.0247 (3)
H111	0.2492	0.3127	0.8837	0.030*
H112	0.2253	0.4310	0.9345	0.030*
C12	0.39114 (12)	0.37727 (12)	1.02174 (12)	0.0251 (3)
H12	0.4177	0.4224	0.9724	0.030*
C13	0.41575 (12)	0.44578 (12)	1.13237 (12)	0.0281 (3)
H131	0.4970	0.4601	1.1752	0.034*
H132	0.3772	0.5218	1.1126	0.034*
C14	0.45213 (11)	0.26015 (12)	1.05387 (12)	0.0243 (3)
H141	0.5336	0.2735	1.0965	0.029*
H142	0.4379	0.2162	0.9829	0.029*
C15	0.08958 (11)	−0.08417 (11)	0.90145 (11)	0.0208 (3)
H15	0.0517	−0.0253	0.9291	0.025*
C16	0.06399 (12)	−0.20747 (12)	0.92979 (13)	0.0268 (3)
H161	0.0907	−0.2154	1.0141	0.032*
H162	−0.0177	−0.2206	0.8923	0.032*
C17	0.12138 (12)	−0.29816 (12)	0.88746 (12)	0.0262 (3)
H17	0.1049	−0.3776	0.9072	0.031*
C18	0.24780 (11)	−0.27758 (12)	0.94582 (13)	0.0269 (3)
H181	0.2853	−0.3364	0.9190	0.032*
H182	0.2765	−0.2857	1.0303	0.032*
C19	0.27425 (11)	−0.15525 (11)	0.91687 (12)	0.0222 (3)
H19	0.3568	−0.1423	0.9547	0.027*
C20	0.04609 (11)	−0.07449 (12)	0.77019 (11)	0.0252 (3)
H201	−0.0358	−0.0868	0.7322	0.030*
H202	0.0616	0.0043	0.7500	0.030*
C21	0.10309 (12)	−0.16537 (12)	0.72720 (12)	0.0265 (3)
H21	0.0746	−0.1579	0.6419	0.032*
C22	0.07740 (13)	−0.28772 (12)	0.75650 (12)	0.0289 (3)
H221	−0.0042	−0.3016	0.7184	0.035*
H222	0.1137	−0.3466	0.7284	0.035*
C23	0.22948 (12)	−0.14538 (12)	0.78553 (12)	0.0260 (3)
H231	0.2465	−0.0673	0.7653	0.031*
H232	0.2666	−0.2037	0.7578	0.031*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.03017 (18)	0.02351 (18)	0.01694 (15)	−0.00242 (13)	0.00646 (13)	0.00317 (12)
S2	0.03319 (19)	0.02786 (19)	0.02206 (16)	−0.00654 (14)	0.01755 (14)	−0.00468 (12)
S4	0.03230 (18)	0.01695 (16)	0.01708 (15)	−0.00354 (12)	0.01297 (13)	−0.00189 (11)
C3	0.0207 (6)	0.0197 (6)	0.0150 (5)	−0.0012 (5)	0.0090 (5)	−0.0023 (4)
C5	0.0198 (6)	0.0161 (5)	0.0150 (5)	0.0008 (4)	0.0075 (4)	0.0014 (4)
C6	0.0183 (6)	0.0215 (6)	0.0212 (6)	0.0039 (5)	0.0054 (5)	−0.0041 (5)
C7	0.0278 (7)	0.0270 (7)	0.0276 (7)	0.0019 (5)	0.0122 (6)	−0.0092 (5)
C8	0.0284 (7)	0.0250 (7)	0.0208 (6)	−0.0015 (5)	0.0070 (5)	−0.0078 (5)
C9	0.0260 (6)	0.0264 (7)	0.0177 (6)	−0.0020 (5)	0.0040 (5)	−0.0007 (5)
C10	0.0183 (6)	0.0210 (6)	0.0201 (6)	0.0019 (5)	0.0060 (5)	0.0003 (5)
C11	0.0282 (7)	0.0187 (6)	0.0204 (6)	0.0030 (5)	0.0043 (5)	0.0007 (5)
C12	0.0279 (7)	0.0220 (6)	0.0231 (6)	−0.0024 (5)	0.0091 (5)	0.0015 (5)
C13	0.0297 (7)	0.0209 (6)	0.0267 (7)	−0.0025 (5)	0.0058 (6)	−0.0031 (5)
C14	0.0213 (6)	0.0251 (7)	0.0281 (7)	−0.0010 (5)	0.0124 (5)	−0.0008 (5)
C15	0.0185 (6)	0.0210 (6)	0.0222 (6)	0.0022 (5)	0.0083 (5)	−0.0004 (5)
C16	0.0241 (6)	0.0275 (7)	0.0311 (7)	−0.0054 (5)	0.0142 (6)	−0.0006 (6)
C17	0.0286 (7)	0.0183 (6)	0.0306 (7)	−0.0034 (5)	0.0121 (6)	0.0012 (5)
C18	0.0265 (7)	0.0182 (6)	0.0331 (7)	0.0038 (5)	0.0104 (6)	0.0017 (5)
C19	0.0202 (6)	0.0185 (6)	0.0284 (6)	0.0017 (5)	0.0111 (5)	−0.0013 (5)
C20	0.0236 (6)	0.0229 (7)	0.0211 (6)	0.0023 (5)	0.0024 (5)	0.0004 (5)
C21	0.0348 (7)	0.0215 (6)	0.0208 (6)	−0.0019 (5)	0.0099 (6)	−0.0028 (5)
C22	0.0330 (7)	0.0215 (7)	0.0297 (7)	−0.0046 (6)	0.0114 (6)	−0.0053 (5)
C23	0.0354 (7)	0.0204 (6)	0.0290 (7)	−0.0020 (5)	0.0206 (6)	−0.0054 (5)

Geometric parameters (Å, º)

S1—C5	1.8334 (12)	C13—H131	0.99
S1—S2	2.0281 (5)	C13—H132	0.99
S2—C3	1.8378 (12)	C14—H141	0.99
S4—C3	1.8532 (12)	C14—H142	0.99
S4—C5	1.8554 (12)	C15—C20	1.5368 (19)
C3—C10	1.5423 (17)	C15—C16	1.5416 (18)
C3—C6	1.5473 (18)	C15—H15	1.00
C5—C15	1.5353 (17)	C16—C17	1.531 (2)
C5—C19	1.5449 (17)	C16—H161	0.99
C6—C11	1.5334 (19)	C16—H162	0.99
C6—C7	1.5429 (18)	C17—C18	1.5319 (19)
C6—H6	1.00	C17—C22	1.533 (2)
C7—C8	1.5346 (19)	C17—H17	1.00
C7—H71	0.99	C18—C19	1.5378 (19)
C7—H72	0.99	C18—H181	0.99
C8—C13	1.533 (2)	C18—H182	0.99
C8—C9	1.5331 (19)	C19—C23	1.5362 (19)
C8—H8	1.00	C19—H19	1.00
C9—C10	1.5369 (18)	C20—C21	1.5336 (19)
C9—H91	0.99	C20—H201	0.99
C9—H92	0.99	C20—H202	0.99
C10—C14	1.5382 (18)	C21—C23	1.530 (2)
C10—H10	1.00	C21—C22	1.5362 (19)
C11—C12	1.5327 (19)	C21—H21	1.00
C11—H111	0.99	C22—H221	0.99
C11—H112	0.99	C22—H222	0.99
C12—C14	1.5348 (19)	C23—H231	0.99
C12—C13	1.5369 (19)	C23—H232	0.99
C12—H12	1.00
C5—S1—S2	96.13 (4)	H131—C13—H132	108.3
C3—S2—S1	96.22 (4)	C12—C14—C10	110.26 (11)
C3—S4—C5	104.53 (5)	C12—C14—H141	109.6
C10—C3—C6	109.04 (10)	C10—C14—H141	109.6
C10—C3—S2	113.19 (8)	C12—C14—H142	109.6
C6—C3—S2	107.87 (8)	C10—C14—H142	109.6
C10—C3—S4	111.14 (8)	H141—C14—H142	108.1
C6—C3—S4	109.41 (8)	C5—C15—C20	109.33 (11)
S2—C3—S4	106.08 (6)	C5—C15—C16	109.50 (10)
C15—C5—C19	109.60 (10)	C20—C15—C16	108.27 (11)
C15—C5—S1	113.76 (9)	C5—C15—H15	109.9
C19—C5—S1	107.42 (8)	C20—C15—H15	109.9
C15—C5—S4	111.42 (8)	C16—C15—H15	109.9
C19—C5—S4	109.04 (8)	C17—C16—C15	110.26 (11)
S1—C5—S4	105.40 (6)	C17—C16—H161	109.6
C11—C6—C7	108.66 (11)	C15—C16—H161	109.6
C11—C6—C3	109.58 (10)	C17—C16—H162	109.6
C7—C6—C3	109.42 (10)	C15—C16—H162	109.6
C11—C6—H6	109.7	H161—C16—H162	108.1
C7—C6—H6	109.7	C16—C17—C18	109.42 (11)
C3—C6—H6	109.7	C16—C17—C22	109.41 (12)
C8—C7—C6	109.91 (11)	C18—C17—C22	109.61 (12)
C8—C7—H71	109.7	C16—C17—H17	109.5
C6—C7—H71	109.7	C18—C17—H17	109.5
C8—C7—H72	109.7	C22—C17—H17	109.5
C6—C7—H72	109.7	C17—C18—C19	110.00 (11)
H71—C7—H72	108.2	C17—C18—H181	109.7
C13—C8—C9	109.74 (12)	C19—C18—H181	109.7
C13—C8—C7	109.65 (12)	C17—C18—H182	109.7
C9—C8—C7	109.15 (11)	C19—C18—H182	109.7
C13—C8—H8	109.4	H181—C18—H182	108.2
C9—C8—H8	109.4	C23—C19—C18	108.50 (11)
C7—C8—H8	109.4	C23—C19—C5	109.49 (10)
C8—C9—C10	109.99 (10)	C18—C19—C5	109.42 (11)
C8—C9—H91	109.7	C23—C19—H19	109.8
C10—C9—H91	109.7	C18—C19—H19	109.8
C8—C9—H92	109.7	C5—C19—H19	109.8
C10—C9—H92	109.7	C21—C20—C15	110.11 (11)
H91—C9—H92	108.2	C21—C20—H201	109.6
C9—C10—C14	108.52 (11)	C15—C20—H201	109.6
C9—C10—C3	109.78 (10)	C21—C20—H202	109.6
C14—C10—C3	109.39 (10)	C15—C20—H202	109.6
C9—C10—H10	109.7	H201—C20—H202	108.2
C14—C10—H10	109.7	C23—C21—C20	109.39 (11)
C3—C10—H10	109.7	C23—C21—C22	109.44 (12)
C12—C11—C6	110.20 (11)	C20—C21—C22	109.70 (12)
C12—C11—H111	109.6	C23—C21—H21	109.4
C6—C11—H111	109.6	C20—C21—H21	109.4
C12—C11—H112	109.6	C22—C21—H21	109.4
C6—C11—H112	109.6	C17—C22—C21	109.00 (11)
H111—C11—H112	108.1	C17—C22—H221	109.9
C11—C12—C14	109.21 (11)	C21—C22—H221	109.9
C11—C12—C13	109.61 (12)	C17—C22—H222	109.9
C14—C12—C13	109.17 (11)	C21—C22—H222	109.9
C11—C12—H12	109.6	H221—C22—H222	108.3
C14—C12—H12	109.6	C21—C23—C19	110.00 (11)
C13—C12—H12	109.6	C21—C23—H231	109.7
C8—C13—C12	109.19 (11)	C19—C23—H231	109.7
C8—C13—H131	109.8	C21—C23—H232	109.7
C12—C13—H131	109.8	C19—C23—H232	109.7
C8—C13—H132	109.8	H231—C23—H232	108.2
C12—C13—H132	109.8
C5—S1—S2—C3	−53.84 (6)	C11—C12—C13—C8	59.69 (14)
S1—S2—C3—C10	−78.92 (9)	C14—C12—C13—C8	−59.89 (15)
S1—S2—C3—C6	160.35 (7)	C11—C12—C14—C10	−59.38 (14)
S1—S2—C3—S4	43.20 (6)	C13—C12—C14—C10	60.45 (14)
C5—S4—C3—C10	106.57 (9)	C9—C10—C14—C12	−59.81 (14)
C5—S4—C3—C6	−132.95 (9)	C3—C10—C14—C12	59.94 (14)
C5—S4—C3—S2	−16.84 (7)	C19—C5—C15—C20	−59.40 (13)
S2—S1—C5—C15	−76.60 (8)	S1—C5—C15—C20	−179.67 (8)
S2—S1—C5—C19	161.92 (8)	S4—C5—C15—C20	61.36 (11)
S2—S1—C5—S4	45.75 (6)	C19—C5—C15—C16	59.07 (13)
C3—S4—C5—C15	102.96 (9)	S1—C5—C15—C16	−61.20 (12)
C3—S4—C5—C19	−135.95 (9)	S4—C5—C15—C16	179.84 (8)
C3—S4—C5—S1	−20.89 (7)	C5—C15—C16—C17	−59.34 (14)
C10—C3—C6—C11	59.70 (13)	C20—C15—C16—C17	59.79 (14)
S2—C3—C6—C11	−177.01 (8)	C15—C16—C17—C18	59.36 (15)
S4—C3—C6—C11	−62.05 (11)	C15—C16—C17—C22	−60.75 (14)
C10—C3—C6—C7	−59.35 (13)	C16—C17—C18—C19	−59.64 (15)
S2—C3—C6—C7	63.94 (12)	C22—C17—C18—C19	60.34 (15)
S4—C3—C6—C7	178.91 (9)	C17—C18—C19—C23	−59.65 (14)
C11—C6—C7—C8	−59.52 (15)	C17—C18—C19—C5	59.76 (14)
C3—C6—C7—C8	60.09 (15)	C15—C5—C19—C23	59.35 (13)
C6—C7—C8—C13	60.24 (15)	S1—C5—C19—C23	−176.59 (9)
C6—C7—C8—C9	−60.00 (15)	S4—C5—C19—C23	−62.85 (12)
C13—C8—C9—C10	−60.28 (14)	C15—C5—C19—C18	−59.45 (13)
C7—C8—C9—C10	59.90 (14)	S1—C5—C19—C18	64.60 (11)
C8—C9—C10—C14	59.44 (14)	S4—C5—C19—C18	178.35 (9)
C8—C9—C10—C3	−60.07 (14)	C5—C15—C20—C21	59.84 (14)
C6—C3—C10—C9	59.42 (13)	C16—C15—C20—C21	−59.40 (14)
S2—C3—C10—C9	−60.64 (12)	C15—C20—C21—C23	−59.73 (14)
S4—C3—C10—C9	−179.89 (9)	C15—C20—C21—C22	60.32 (14)
C6—C3—C10—C14	−59.56 (13)	C16—C17—C22—C21	60.03 (15)
S2—C3—C10—C14	−179.62 (9)	C18—C17—C22—C21	−59.96 (15)
S4—C3—C10—C14	61.14 (12)	C23—C21—C22—C17	60.11 (15)
C7—C6—C11—C12	59.57 (14)	C20—C21—C22—C17	−59.92 (15)
C3—C6—C11—C12	−59.95 (14)	C20—C21—C23—C19	59.51 (14)
C6—C11—C12—C14	59.37 (14)	C22—C21—C23—C19	−60.70 (14)
C6—C11—C12—C13	−60.18 (14)	C18—C19—C23—C21	59.91 (13)
C9—C8—C13—C12	60.04 (14)	C5—C19—C23—C21	−59.46 (14)
C7—C8—C13—C12	−59.84 (15)