1,8-Bis­(phenyl­sulfanyl)­octane

The title compound, C₂₀H₂₆S₂, crystallizes with two half-mol­ecules in the asymmetric unit. In each independent mol­ecule, there is a centre of inversion at the mid-point of the central C-C bond. Each mol­ecule, excluding H atoms, is roughly planar, and adopts an all-anti conformation. The dihedral angles between the phenyl ring and backbone chain are 20.1 (2) and 20.3 (2)°.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.052
• wR factor = 0.132
• Data-to-parameter ratio = 18.2

checkCIF/PLATON results

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Computing details

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

1,8-Bis(phenylthio)octane

Crystal data

C20H26S2	Z = 2
Mr = 330.53	F(000) = 356
Triclinic, P1	Dx = 1.224 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.579 (2) Å	Cell parameters from 903 reflections
b = 7.857 (3) Å	θ = 3.0–26.3°
c = 20.590 (7) Å	µ = 0.29 mm^−1
α = 84.044 (5)°	T = 293 K
β = 87.890 (6)°	Block, colourless
γ = 89.572 (6)°	0.22 × 0.18 × 0.14 mm
V = 897.1 (6) Å^3

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	3612 independent reflections
Radiation source: fine-focus sealed tube	2506 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.023
φ and ω scans	θmax = 26.4°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −5→6
Tmin = 0.936, Tmax = 0.965	k = −9→8
5201 measured reflections	l = −25→25

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H-atom parameters constrained
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0562P)^2 + 0.209P] where P = (Fo^2 + 2Fc^2)/3
3612 reflections	(Δ/σ)max < 0.001
199 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
S1	0.41169 (12)	0.37995 (10)	0.27985 (3)	0.0541 (2)
S2	1.10101 (12)	0.07884 (9)	0.72325 (3)	0.0533 (2)
C1	0.2811 (4)	0.2671 (3)	0.16848 (12)	0.0429 (6)
H1	0.1509	0.2221	0.1939	0.051*
C2	0.2972 (5)	0.2463 (3)	0.10329 (12)	0.0493 (6)
H2	0.1771	0.1876	0.0849	0.059*
C3	0.4880 (5)	0.3109 (3)	0.06473 (12)	0.0498 (6)
H3	0.4986	0.2963	0.0205	0.060*
C4	0.6620 (5)	0.3973 (3)	0.09272 (12)	0.0486 (6)
H4	0.7918	0.4419	0.0670	0.058*
C5	0.6494 (4)	0.4197 (3)	0.15782 (11)	0.0441 (6)
H5	0.7700	0.4786	0.1759	0.053*
C6	0.4567 (4)	0.3543 (3)	0.19671 (10)	0.0365 (5)
C7	0.7015 (4)	0.4241 (3)	0.30811 (11)	0.0481 (6)
H7A	0.8130	0.3338	0.2988	0.058*
H7B	0.7613	0.5313	0.2860	0.058*
C8	0.6797 (5)	0.4353 (3)	0.38063 (11)	0.0525 (7)
H8A	0.5657	0.5251	0.3888	0.063*
H8B	0.6146	0.3283	0.4015	0.063*
C9	0.9090 (5)	0.4703 (3)	0.41183 (11)	0.0516 (6)
H9A	0.9751	0.5765	0.3906	0.062*
H9B	1.0222	0.3797	0.4042	0.062*
C10	0.8865 (4)	0.4836 (3)	0.48367 (11)	0.0516 (7)
H10A	0.7742	0.5750	0.4911	0.062*
H10B	0.8177	0.3780	0.5046	0.062*
C11	0.8569 (4)	0.2254 (3)	0.82348 (11)	0.0450 (6)
H11	0.7449	0.2673	0.7934	0.054*
C12	0.8309 (5)	0.2589 (3)	0.88731 (12)	0.0510 (6)
H12	0.6999	0.3226	0.9004	0.061*
C13	0.9954 (5)	0.1997 (3)	0.93226 (12)	0.0508 (6)
H13	0.9768	0.2231	0.9755	0.061*
C14	1.1875 (5)	0.1058 (3)	0.91261 (12)	0.0530 (7)
H14	1.3002	0.0655	0.9427	0.064*
C15	1.2150 (4)	0.0706 (3)	0.84923 (12)	0.0469 (6)
H15	1.3462	0.0066	0.8366	0.056*
C16	1.0496 (4)	0.1292 (3)	0.80372 (11)	0.0364 (5)
C17	0.8136 (4)	0.1033 (3)	0.68718 (11)	0.0455 (6)
H17A	0.6945	0.0369	0.7142	0.055*
H17B	0.7648	0.2226	0.6838	0.055*
C18	0.8322 (5)	0.0418 (3)	0.61991 (11)	0.0499 (6)
H18A	0.9529	0.1087	0.5937	0.060*
H18B	0.8848	−0.0766	0.6240	0.060*
C19	0.5986 (5)	0.0555 (3)	0.58507 (11)	0.0486 (6)
H19A	0.5461	0.1739	0.5810	0.058*
H19B	0.4780	−0.0113	0.6114	0.058*
C20	0.6157 (5)	−0.0059 (3)	0.51775 (11)	0.0504 (6)
H20A	0.7363	0.0611	0.4916	0.060*
H20B	0.6694	−0.1242	0.5219	0.060*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0444 (4)	0.0827 (5)	0.0367 (4)	−0.0022 (3)	−0.0017 (3)	−0.0135 (3)
S2	0.0447 (4)	0.0756 (5)	0.0413 (4)	0.0056 (3)	0.0027 (3)	−0.0162 (3)
C1	0.0396 (13)	0.0429 (13)	0.0461 (14)	−0.0017 (11)	−0.0065 (10)	−0.0023 (10)
C2	0.0490 (15)	0.0497 (15)	0.0514 (15)	−0.0033 (12)	−0.0171 (12)	−0.0101 (11)
C3	0.0608 (17)	0.0521 (15)	0.0375 (14)	0.0062 (13)	−0.0062 (12)	−0.0080 (11)
C4	0.0500 (15)	0.0513 (15)	0.0431 (14)	−0.0006 (12)	0.0070 (11)	−0.0021 (11)
C5	0.0398 (13)	0.0487 (14)	0.0447 (14)	−0.0053 (11)	−0.0040 (11)	−0.0073 (11)
C6	0.0369 (13)	0.0381 (12)	0.0348 (12)	0.0057 (10)	−0.0037 (10)	−0.0040 (9)
C7	0.0506 (15)	0.0573 (15)	0.0379 (13)	−0.0060 (12)	−0.0074 (11)	−0.0098 (11)
C8	0.0580 (17)	0.0645 (17)	0.0367 (14)	−0.0009 (13)	−0.0048 (12)	−0.0118 (12)
C9	0.0544 (16)	0.0645 (17)	0.0374 (14)	−0.0087 (13)	−0.0045 (11)	−0.0104 (11)
C10	0.0564 (17)	0.0621 (16)	0.0377 (14)	−0.0058 (13)	−0.0047 (12)	−0.0106 (12)
C11	0.0454 (14)	0.0494 (14)	0.0404 (14)	0.0087 (11)	−0.0062 (11)	−0.0038 (11)
C12	0.0506 (16)	0.0566 (16)	0.0470 (15)	0.0094 (13)	0.0008 (12)	−0.0122 (12)
C13	0.0597 (17)	0.0571 (16)	0.0372 (14)	−0.0025 (13)	−0.0041 (12)	−0.0113 (11)
C14	0.0557 (16)	0.0575 (16)	0.0472 (15)	0.0009 (13)	−0.0192 (12)	−0.0049 (12)
C15	0.0403 (14)	0.0487 (14)	0.0526 (15)	0.0063 (11)	−0.0067 (11)	−0.0088 (11)
C16	0.0348 (12)	0.0374 (12)	0.0372 (12)	−0.0036 (10)	−0.0022 (10)	−0.0039 (9)
C17	0.0492 (15)	0.0560 (15)	0.0319 (12)	0.0039 (12)	−0.0030 (11)	−0.0075 (10)
C18	0.0573 (16)	0.0580 (16)	0.0351 (13)	0.0020 (13)	0.0001 (12)	−0.0095 (11)
C19	0.0566 (16)	0.0569 (15)	0.0332 (13)	0.0015 (13)	0.0000 (11)	−0.0099 (11)
C20	0.0596 (17)	0.0585 (16)	0.0345 (13)	0.0010 (13)	0.0012 (11)	−0.0124 (11)

Geometric parameters (Å, º)

S1—C6	1.753 (2)	C10—H10A	0.9700
S1—C7	1.787 (3)	C10—H10B	0.9700
S2—C16	1.756 (2)	C11—C12	1.369 (3)
S2—C17	1.793 (2)	C11—C16	1.383 (3)
C1—C2	1.369 (3)	C11—H11	0.9300
C1—C6	1.379 (3)	C12—C13	1.372 (3)
C1—H1	0.9300	C12—H12	0.9300
C2—C3	1.373 (3)	C13—C14	1.369 (3)
C2—H2	0.9300	C13—H13	0.9300
C3—C4	1.367 (3)	C14—C15	1.364 (3)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.369 (3)	C15—C16	1.382 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.386 (3)	C17—C18	1.514 (3)
C5—H5	0.9300	C17—H17A	0.9700
C7—C8	1.505 (3)	C17—H17B	0.9700
C7—H7A	0.9700	C18—C19	1.508 (3)
C7—H7B	0.9700	C18—H18A	0.9700
C8—C9	1.492 (3)	C18—H18B	0.9700
C8—H8A	0.9700	C19—C20	1.514 (3)
C8—H8B	0.9700	C19—H19A	0.9700
C9—C10	1.494 (3)	C19—H19B	0.9700
C9—H9A	0.9700	C20—C20^ii	1.505 (5)
C9—H9B	0.9700	C20—H20A	0.9700
C10—C10^i	1.492 (5)	C20—H20B	0.9700
C6—S1—C7	105.4 (1)	H10A—C10—H10B	107.4
C16—S2—C17	104.5 (1)	C12—C11—C16	120.0 (2)
C2—C1—C6	120.5 (2)	C12—C11—H11	120.0
C2—C1—H1	119.8	C16—C11—H11	120.0
C6—C1—H1	119.8	C11—C12—C13	120.9 (2)
C1—C2—C3	120.9 (2)	C11—C12—H12	119.6
C1—C2—H2	119.6	C13—C12—H12	119.6
C3—C2—H2	119.6	C14—C13—C12	119.1 (2)
C4—C3—C2	118.6 (2)	C14—C13—H13	120.4
C4—C3—H3	120.7	C12—C13—H13	120.4
C2—C3—H3	120.7	C15—C14—C13	120.6 (2)
C3—C4—C5	121.4 (2)	C15—C14—H14	119.7
C3—C4—H4	119.3	C13—C14—H14	119.7
C5—C4—H4	119.3	C14—C15—C16	120.6 (2)
C4—C5—C6	119.9 (2)	C14—C15—H15	119.7
C4—C5—H5	120.1	C16—C15—H15	119.7
C6—C5—H5	120.1	C15—C16—C11	118.8 (2)
C1—C6—C5	118.7 (2)	C15—C16—S2	117.37 (17)
C1—C6—S1	116.48 (18)	C11—C16—S2	123.87 (17)
C5—C6—S1	124.80 (18)	C18—C17—S2	108.56 (17)
C8—C7—S1	108.41 (17)	C18—C17—H17A	110.0
C8—C7—H7A	110.0	S2—C17—H17A	110.0
S1—C7—H7A	110.0	C18—C17—H17B	110.0
C8—C7—H7B	110.0	S2—C17—H17B	110.0
S1—C7—H7B	110.0	H17A—C17—H17B	108.4
H7A—C7—H7B	108.4	C19—C18—C17	113.1 (2)
C9—C8—C7	114.9 (2)	C19—C18—H18A	109.0
C9—C8—H8A	108.5	C17—C18—H18A	109.0
C7—C8—H8A	108.5	C19—C18—H18B	109.0
C9—C8—H8B	108.5	C17—C18—H18B	109.0
C7—C8—H8B	108.5	H18A—C18—H18B	107.8
H8A—C8—H8B	107.5	C18—C19—C20	113.4 (2)
C8—C9—C10	114.8 (2)	C18—C19—H19A	108.9
C8—C9—H9A	108.6	C20—C19—H19A	108.9
C10—C9—H9A	108.6	C18—C19—H19B	108.9
C8—C9—H9B	108.6	C20—C19—H19B	108.9
C10—C9—H9B	108.6	H19A—C19—H19B	107.7
H9A—C9—H9B	107.5	C20^ii—C20—C19	114.3 (3)
C10^i—C10—C9	116.0 (3)	C20^ii—C20—H20A	108.7
C10^i—C10—H10A	108.3	C19—C20—H20A	108.7
C9—C10—H10A	108.3	C20^ii—C20—H20B	108.7
C10^i—C10—H10B	108.3	C19—C20—H20B	108.7
C9—C10—H10B	108.3	H20A—C20—H20B	107.6
C6—C1—C2—C3	0.2 (4)	C16—C11—C12—C13	0.7 (4)
C1—C2—C3—C4	−0.2 (4)	C11—C12—C13—C14	−0.1 (4)
C2—C3—C4—C5	0.2 (4)	C12—C13—C14—C15	−0.2 (4)
C3—C4—C5—C6	−0.1 (4)	C13—C14—C15—C16	0.0 (4)
C2—C1—C6—C5	−0.2 (3)	C14—C15—C16—C11	0.5 (4)
C2—C1—C6—S1	177.69 (18)	C14—C15—C16—S2	179.6 (2)
C4—C5—C6—C1	0.2 (3)	C12—C11—C16—C15	−0.9 (4)
C4—C5—C6—S1	−177.54 (18)	C12—C11—C16—S2	−179.9 (2)
C7—S1—C6—C1	159.90 (18)	C17—S2—C16—C15	159.79 (19)
C7—S1—C6—C5	−22.4 (2)	C17—S2—C16—C11	−21.2 (2)
C6—S1—C7—C8	−175.99 (17)	C16—S2—C17—C18	−173.20 (16)
S1—C7—C8—C9	179.48 (19)	S2—C17—C18—C19	179.57 (18)
C7—C8—C9—C10	179.2 (2)	C17—C18—C19—C20	−180.0 (2)
C8—C9—C10—C10^i	179.3 (3)	C18—C19—C20—C20^ii	179.8 (3)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+1, −y, −z+1.