Bis(N,N-dicyclo­hexyl­thio­carbamo­yl) disulfide

The title compound, C₂₆H₄₄N₂S₂, was prepared by the oxidation of the corresponding thio­carbamate with iodine. The disulfide S—S distance is close to the distances observed in free (uncoordinated) disulfides. A crystallographic twofold axis passes through the mid-point of the S---S bond.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C)= 0.004 Å
• R factor = 0.047
• wR factor = 0.127
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

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Computing details

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

Bis(N,N-dicyclohexylthiocarbamoyl) disulfide

Crystal data

C26H44N2O2S2	F(000) = 1048
Mr = 480.75	Dx = 1.201 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1510 reflections
a = 12.868 (3) Å	θ = 2.5–24.3°
b = 25.435 (6) Å	µ = 0.23 mm^−1
c = 9.080 (2) Å	T = 298 K
β = 116.579 (3)°	Block, yellow
V = 2657.8 (11) Å^3	0.53 × 0.41 × 0.32 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer	2341 independent reflections
Radiation source: fine-focus sealed tube	1519 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→14
Tmin = 0.890, Tmax = 0.932	k = −24→30
6913 measured reflections	l = −10→10

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.127	H-atom parameters constrained
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0586P)^2 + 1.1207P] where P = (Fo^2 + 2Fc^2)/3
2341 reflections	(Δ/σ)max < 0.001
145 parameters	Δρmax = 0.37 e Å^−3
0 restraints	Δρmin = −0.19 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2σ(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	0.45764 (5)	0.05959 (3)	0.32018 (9)	0.0439 (2)
N1	0.26971 (17)	0.11701 (8)	0.2759 (3)	0.0387 (5)
O1	0.34661 (16)	0.13382 (8)	0.0954 (2)	0.0517 (5)
C1	0.3461 (2)	0.11028 (10)	0.2130 (3)	0.0396 (6)
C2	0.1818 (2)	0.15968 (10)	0.2081 (3)	0.0388 (6)
H2	0.1391	0.1596	0.2744	0.047*
C3	0.2350 (2)	0.21386 (11)	0.2277 (4)	0.0515 (8)
H3A	0.2810	0.2155	0.1675	0.062*
H3B	0.2864	0.2201	0.3432	0.062*
C4	0.1427 (3)	0.25628 (12)	0.1649 (4)	0.0609 (9)
H4A	0.1038	0.2579	0.2349	0.073*
H4B	0.1793	0.2901	0.1706	0.073*
C5	0.0543 (2)	0.24583 (12)	−0.0102 (4)	0.0654 (9)
H5A	0.0916	0.2482	−0.0821	0.079*
H5B	−0.0060	0.2724	−0.0442	0.079*
C6	0.0002 (2)	0.19199 (12)	−0.0272 (4)	0.0580 (9)
H6A	−0.0536	0.1858	−0.1417	0.070*
H6B	−0.0433	0.1907	0.0366	0.070*
C7	0.0924 (2)	0.14929 (11)	0.0320 (3)	0.0484 (7)
H7A	0.0560	0.1154	0.0259	0.058*
H7B	0.1306	0.1482	−0.0389	0.058*
C8	0.2781 (2)	0.08843 (10)	0.4222 (3)	0.0379 (6)
H8	0.3340	0.0599	0.4428	0.046*
C9	0.1634 (2)	0.06283 (11)	0.3941 (3)	0.0463 (7)
H9A	0.1050	0.0898	0.3718	0.056*
H9B	0.1370	0.0398	0.2990	0.056*
C10	0.1783 (3)	0.03140 (13)	0.5440 (4)	0.0594 (9)
H10A	0.1035	0.0174	0.5267	0.071*
H10B	0.2299	0.0020	0.5585	0.071*
C11	0.2274 (3)	0.06483 (13)	0.6979 (4)	0.0652 (10)
H11A	0.1712	0.0916	0.6888	0.078*
H11B	0.2406	0.0430	0.7922	0.078*
C12	0.3398 (3)	0.09089 (12)	0.7255 (3)	0.0578 (8)
H12A	0.3991	0.0643	0.7491	0.069*
H12B	0.3651	0.1141	0.8201	0.069*
C13	0.3256 (2)	0.12247 (11)	0.5749 (3)	0.0478 (7)
H13A	0.2732	0.1517	0.5591	0.057*
H13B	0.4003	0.1367	0.5931	0.057*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0370 (4)	0.0510 (5)	0.0517 (5)	0.0039 (3)	0.0268 (3)	0.0082 (3)
N1	0.0368 (12)	0.0483 (14)	0.0375 (13)	0.0061 (10)	0.0225 (10)	0.0074 (11)
O1	0.0518 (12)	0.0683 (13)	0.0468 (12)	0.0164 (10)	0.0326 (10)	0.0141 (10)
C1	0.0352 (14)	0.0485 (16)	0.0370 (16)	0.0002 (12)	0.0178 (12)	−0.0001 (13)
C2	0.0346 (14)	0.0464 (17)	0.0395 (16)	0.0055 (12)	0.0204 (12)	0.0062 (13)
C3	0.0432 (16)	0.0525 (18)	0.0523 (19)	−0.0021 (14)	0.0157 (14)	0.0002 (14)
C4	0.059 (2)	0.0472 (19)	0.078 (3)	0.0039 (15)	0.0317 (19)	0.0024 (17)
C5	0.0504 (19)	0.063 (2)	0.074 (2)	0.0103 (16)	0.0203 (18)	0.0257 (18)
C6	0.0394 (16)	0.071 (2)	0.056 (2)	0.0042 (15)	0.0141 (15)	0.0128 (16)
C7	0.0415 (16)	0.0551 (18)	0.0443 (18)	−0.0031 (13)	0.0154 (14)	0.0018 (14)
C8	0.0371 (14)	0.0456 (16)	0.0366 (16)	0.0051 (12)	0.0215 (12)	0.0063 (13)
C9	0.0434 (16)	0.0496 (17)	0.0475 (18)	−0.0046 (13)	0.0218 (14)	0.0023 (14)
C10	0.0546 (18)	0.066 (2)	0.066 (2)	−0.0055 (16)	0.0343 (17)	0.0152 (17)
C11	0.080 (2)	0.078 (2)	0.056 (2)	0.0150 (19)	0.0462 (19)	0.0231 (19)
C12	0.071 (2)	0.063 (2)	0.0373 (17)	0.0032 (17)	0.0226 (16)	0.0054 (15)
C13	0.0482 (16)	0.0547 (18)	0.0386 (16)	−0.0042 (14)	0.0176 (13)	0.0029 (14)

Geometric parameters (Å, º)

S1—C1	1.849 (3)	C6—H6B	0.9700
S1—S1^i	2.0138 (13)	C7—H7A	0.9700
N1—C1	1.350 (3)	C7—H7B	0.9700
N1—C8	1.475 (3)	C8—C13	1.513 (4)
N1—C2	1.488 (3)	C8—C9	1.526 (3)
O1—C1	1.227 (3)	C8—H8	0.9800
C2—C3	1.513 (4)	C9—C10	1.516 (4)
C2—C7	1.518 (3)	C9—H9A	0.9700
C2—H2	0.9800	C9—H9B	0.9700
C3—C4	1.515 (4)	C10—C11	1.511 (4)
C3—H3A	0.9700	C10—H10A	0.9700
C3—H3B	0.9700	C10—H10B	0.9700
C4—C5	1.508 (4)	C11—C12	1.507 (4)
C4—H4A	0.9700	C11—H11A	0.9700
C4—H4B	0.9700	C11—H11B	0.9700
C5—C6	1.513 (4)	C12—C13	1.524 (4)
C5—H5A	0.9700	C12—H12A	0.9700
C5—H5B	0.9700	C12—H12B	0.9700
C6—C7	1.519 (4)	C13—H13A	0.9700
C6—H6A	0.9700	C13—H13B	0.9700
C1—S1—S1^i	100.35 (9)	C2—C7—H7B	109.5
C1—N1—C8	123.0 (2)	C6—C7—H7B	109.5
C1—N1—C2	118.7 (2)	H7A—C7—H7B	108.1
C8—N1—C2	117.9 (2)	N1—C8—C13	112.3 (2)
O1—C1—N1	126.5 (2)	N1—C8—C9	112.6 (2)
O1—C1—S1	119.5 (2)	C13—C8—C9	111.2 (2)
N1—C1—S1	113.98 (19)	N1—C8—H8	106.8
N1—C2—C3	113.3 (2)	C13—C8—H8	106.8
N1—C2—C7	112.7 (2)	C9—C8—H8	106.8
C3—C2—C7	111.8 (2)	C10—C9—C8	110.6 (2)
N1—C2—H2	106.1	C10—C9—H9A	109.5
C3—C2—H2	106.1	C8—C9—H9A	109.5
C7—C2—H2	106.1	C10—C9—H9B	109.5
C2—C3—C4	111.6 (2)	C8—C9—H9B	109.5
C2—C3—H3A	109.3	H9A—C9—H9B	108.1
C4—C3—H3A	109.3	C11—C10—C9	111.5 (3)
C2—C3—H3B	109.3	C11—C10—H10A	109.3
C4—C3—H3B	109.3	C9—C10—H10A	109.3
H3A—C3—H3B	108.0	C11—C10—H10B	109.3
C5—C4—C3	111.5 (2)	C9—C10—H10B	109.3
C5—C4—H4A	109.3	H10A—C10—H10B	108.0
C3—C4—H4A	109.3	C12—C11—C10	112.0 (3)
C5—C4—H4B	109.3	C12—C11—H11A	109.2
C3—C4—H4B	109.3	C10—C11—H11A	109.2
H4A—C4—H4B	108.0	C12—C11—H11B	109.2
C4—C5—C6	111.3 (3)	C10—C11—H11B	109.2
C4—C5—H5A	109.4	H11A—C11—H11B	107.9
C6—C5—H5A	109.4	C11—C12—C13	111.2 (2)
C4—C5—H5B	109.4	C11—C12—H12A	109.4
C6—C5—H5B	109.4	C13—C12—H12A	109.4
H5A—C5—H5B	108.0	C11—C12—H12B	109.4
C5—C6—C7	111.1 (2)	C13—C12—H12B	109.4
C5—C6—H6A	109.4	H12A—C12—H12B	108.0
C7—C6—H6A	109.4	C8—C13—C12	110.9 (2)
C5—C6—H6B	109.4	C8—C13—H13A	109.4
C7—C6—H6B	109.4	C12—C13—H13A	109.4
H6A—C6—H6B	108.0	C8—C13—H13B	109.5
C2—C7—C6	110.7 (2)	C12—C13—H13B	109.4
C2—C7—H7A	109.5	H13A—C13—H13B	108.0
C6—C7—H7A	109.5

Symmetry code: (i) −x+1, y, −z+1/2.