1,10-Bis(phenyl­sulfanyl)decane

In the title structure, C₂₂H₃₀S₂, L¹⁰, the asymmetric unit contains two independent mol­ecules, both of which lie on crystallographic inversion centers, and the aliphatic chains are in the all-trans conformation. The crystal structure is stabilized by a combination of van der Waals forces and weak C—H...π(arene) inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.050
• wR factor = 0.147
• Data-to-parameter ratio = 17.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  CG2     ..       2.91 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL022_ALERT_1_A There is a mismatched ~ on line 244
              U~iso~(H) = 1.2U~eq(C). A final verification of possible voids was performed
              If you require a ~ then it should be escaped
              with a \, i.e. \~
              Otherwise there must be a matching closing ~, e.g. C~2~H~4~

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

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Computing details

Data collection: CAD-4 Software (Enraf–Nonius 1989); cell refinement: CAD-4 Software; data reduction: local program; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: UdMX (local program; Author and year?).

1,10-Bis(phenylthio)decane

Crystal data

C22H30S2	Z = 2
Mr = 358.58	F(000) = 388
Triclinic, P1	Dx = 1.186 Mg m^−3
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 5.570 (2) Å	Cell parameters from 25 reflections
b = 7.943 (3) Å	θ = 20.0–25.0°
c = 22.953 (7) Å	µ = 2.38 mm^−1
α = 82.82 (3)°	T = 298 K
β = 85.05 (3)°	Platelet, colorless
γ = 89.55 (3)°	0.25 × 0.11 × 0.05 mm
V = 1003.8 (6) Å^3

Data collection

Enraf–Nonius CAD-4 diffractometer	2520 reflections with I > 2σ(I)
Radiation source: X-ray sealed tube	Rint = 0.038
Graphite monochromator	θmax = 69.9°, θmin = 2.0°
ω scans	h = −6→6
Absorption correction: gaussian from crystal shape (Reference?)	k = −9→9
Tmin = 0.528, Tmax = 0.868	l = −28→28
24003 measured reflections	4 standard reflections every 60 min
3799 independent reflections	intensity decay: −0.04%

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.147	H-atom parameters constrained
S = 0.91	w = 1/[σ^2(Fo^2) + (0.0908P)^2] where P = (Fo^2 + 2Fc^2)/3
3799 reflections	(Δ/σ)max < 0.001
217 parameters	Δρmax = 0.23 e Å^−3
0 restraints	Δρmin = −0.47 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	0.65406 (12)	0.59409 (9)	0.24941 (3)	0.0656 (2)
S2	−0.14093 (12)	0.86634 (9)	0.75337 (3)	0.0662 (2)
C11	0.5865 (4)	0.6394 (3)	0.32233 (10)	0.0497 (5)
C12	0.7431 (4)	0.5777 (3)	0.36373 (11)	0.0577 (6)
H12	0.8757	0.5137	0.3525	0.069*
C13	0.7044 (5)	0.6103 (3)	0.42098 (11)	0.0647 (7)
H13	0.8121	0.5692	0.4481	0.078*
C14	0.5084 (5)	0.7029 (3)	0.43879 (11)	0.0637 (7)
H14	0.4814	0.7234	0.4778	0.076*
C15	0.3528 (5)	0.7648 (3)	0.39799 (11)	0.0626 (6)
H15	0.2202	0.8283	0.4096	0.075*
C16	0.3908 (5)	0.7340 (3)	0.34010 (10)	0.0574 (6)
H16	0.2843	0.7770	0.3129	0.069*
C21	−0.0791 (4)	0.8446 (3)	0.67821 (9)	0.0480 (5)
C22	−0.2514 (4)	0.7581 (3)	0.65262 (10)	0.0551 (6)
H22	−0.3862	0.7119	0.6756	0.066*
C23	−0.2229 (5)	0.7406 (3)	0.59325 (11)	0.0613 (6)
H23	−0.3389	0.6829	0.5766	0.074*
C24	−0.0251 (5)	0.8075 (3)	0.55874 (10)	0.0623 (7)
H24	−0.0063	0.7955	0.5188	0.075*
C25	0.1453 (5)	0.8926 (3)	0.58385 (11)	0.0614 (6)
H25	0.2797	0.9380	0.5605	0.074*
C26	0.1209 (4)	0.9120 (3)	0.64302 (10)	0.0552 (6)
H26	0.2380	0.9700	0.6592	0.066*
C31	0.3723 (5)	0.6183 (3)	0.21669 (9)	0.0579 (6)
H31A	0.2487	0.5505	0.2411	0.070*
H31B	0.3225	0.7362	0.2136	0.070*
C32	0.4042 (5)	0.5607 (3)	0.15580 (10)	0.0630 (7)
H32A	0.5287	0.6292	0.1321	0.076*
H32B	0.4583	0.4437	0.1596	0.076*
C33	0.1762 (5)	0.5736 (3)	0.12427 (10)	0.0619 (6)
H33A	0.1218	0.6905	0.1206	0.074*
H33B	0.0518	0.5049	0.1480	0.074*
C34	0.2079 (5)	0.5163 (3)	0.06305 (10)	0.0648 (7)
H34A	0.3332	0.5848	0.0396	0.078*
H34B	0.2626	0.3995	0.0669	0.078*
C35	−0.0160 (5)	0.5281 (3)	0.03038 (9)	0.0646 (7)
H35A	−0.0710	0.6448	0.0266	0.078*
H35B	−0.1411	0.4593	0.0537	0.078*
C41	0.1449 (5)	0.9079 (3)	0.77894 (10)	0.0618 (6)
H41A	0.2568	0.8173	0.7714	0.074*
H41B	0.2112	1.0136	0.7583	0.074*
C42	0.1084 (5)	0.9192 (4)	0.84453 (10)	0.0650 (7)
H42A	−0.0036	1.0105	0.8510	0.078*
H42B	0.0349	0.8145	0.8640	0.078*
C43	0.3357 (5)	0.9497 (3)	0.87293 (10)	0.0642 (7)
H43A	0.4112	1.0533	0.8530	0.077*
H43B	0.4464	0.8571	0.8673	0.077*
C44	0.2963 (5)	0.9646 (4)	0.93791 (10)	0.0655 (7)
H44A	0.1875	1.0585	0.9433	0.079*
H44B	0.2173	0.8620	0.9576	0.079*
C45	0.5203 (5)	0.9917 (3)	0.96752 (9)	0.0661 (7)
H45A	0.6002	1.0937	0.9477	0.079*
H45B	0.6285	0.8973	0.9625	0.079*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.0596 (4)	0.0873 (5)	0.0528 (4)	0.0048 (3)	−0.0049 (3)	−0.0208 (3)
S2	0.0611 (4)	0.0918 (5)	0.0488 (3)	−0.0029 (3)	−0.0085 (3)	−0.0175 (3)
C11	0.0529 (13)	0.0473 (12)	0.0501 (12)	−0.0037 (10)	−0.0083 (10)	−0.0081 (9)
C12	0.0526 (14)	0.0582 (14)	0.0649 (14)	0.0053 (11)	−0.0134 (11)	−0.0128 (11)
C13	0.0711 (17)	0.0670 (16)	0.0596 (14)	0.0015 (13)	−0.0246 (13)	−0.0085 (12)
C14	0.0775 (19)	0.0650 (16)	0.0517 (13)	−0.0006 (13)	−0.0105 (12)	−0.0161 (11)
C15	0.0650 (16)	0.0653 (15)	0.0598 (14)	0.0092 (12)	−0.0084 (12)	−0.0156 (12)
C16	0.0600 (15)	0.0602 (14)	0.0542 (13)	0.0092 (12)	−0.0129 (11)	−0.0103 (11)
C21	0.0513 (13)	0.0468 (12)	0.0481 (12)	0.0046 (10)	−0.0130 (10)	−0.0088 (9)
C22	0.0542 (14)	0.0540 (13)	0.0583 (13)	−0.0054 (11)	−0.0118 (11)	−0.0071 (10)
C23	0.0675 (17)	0.0613 (15)	0.0597 (14)	−0.0035 (12)	−0.0217 (12)	−0.0138 (11)
C24	0.0764 (18)	0.0644 (16)	0.0484 (13)	0.0066 (13)	−0.0130 (12)	−0.0116 (11)
C25	0.0627 (16)	0.0631 (15)	0.0575 (14)	−0.0010 (12)	−0.0011 (12)	−0.0072 (11)
C26	0.0533 (14)	0.0573 (14)	0.0571 (13)	−0.0063 (11)	−0.0089 (11)	−0.0122 (11)
C31	0.0644 (16)	0.0648 (15)	0.0459 (12)	0.0004 (12)	−0.0061 (11)	−0.0110 (11)
C32	0.0692 (17)	0.0711 (16)	0.0512 (13)	0.0029 (13)	−0.0085 (12)	−0.0156 (12)
C33	0.0682 (17)	0.0743 (17)	0.0460 (13)	0.0011 (13)	−0.0071 (11)	−0.0168 (11)
C34	0.0737 (18)	0.0768 (17)	0.0466 (13)	0.0014 (14)	−0.0065 (12)	−0.0174 (12)
C35	0.0759 (18)	0.0739 (17)	0.0468 (13)	0.0018 (14)	−0.0088 (12)	−0.0167 (12)
C41	0.0695 (17)	0.0687 (16)	0.0499 (13)	−0.0045 (13)	−0.0109 (12)	−0.0139 (11)
C42	0.0709 (18)	0.0771 (17)	0.0505 (14)	−0.0024 (14)	−0.0121 (12)	−0.0170 (12)
C43	0.0696 (17)	0.0774 (17)	0.0493 (13)	−0.0067 (14)	−0.0116 (12)	−0.0170 (12)
C44	0.0732 (18)	0.0762 (17)	0.0502 (13)	−0.0050 (14)	−0.0110 (12)	−0.0162 (12)
C45	0.0754 (18)	0.0770 (17)	0.0493 (14)	−0.0037 (14)	−0.0118 (13)	−0.0165 (12)

Geometric parameters (Å, º)

S1—C11	1.764 (2)	C31—H31B	0.97
S1—C31	1.796 (3)	C32—C33	1.511 (3)
S2—C21	1.759 (2)	C32—H32A	0.97
S2—C41	1.790 (3)	C32—H32B	0.97
C11—C16	1.380 (3)	C33—C34	1.526 (3)
C11—C12	1.387 (3)	C33—H33A	0.97
C12—C13	1.369 (3)	C33—H33B	0.97
C12—H12	0.93	C34—C35	1.506 (3)
C13—C14	1.373 (4)	C34—H34A	0.97
C13—H13	0.93	C34—H34B	0.97
C14—C15	1.374 (3)	C35—C35^i	1.513 (4)
C14—H14	0.93	C35—H35A	0.97
C15—C16	1.379 (3)	C35—H35B	0.97
C15—H15	0.93	C41—C42	1.516 (3)
C16—H16	0.93	C41—H41A	0.97
C21—C26	1.388 (3)	C41—H41B	0.97
C21—C22	1.395 (3)	C42—C43	1.507 (3)
C22—C23	1.382 (3)	C42—H42A	0.97
C22—H22	0.93	C42—H42B	0.97
C23—C24	1.370 (4)	C43—C44	1.508 (3)
C23—H23	0.93	C43—H43A	0.97
C24—C25	1.376 (3)	C43—H43B	0.97
C24—H24	0.93	C44—C45	1.501 (3)
C25—C26	1.381 (3)	C44—H44A	0.97
C25—H25	0.93	C44—H44B	0.97
C26—H26	0.93	C45—C45^ii	1.511 (4)
C31—C32	1.520 (3)	C45—H45A	0.97
C31—H31A	0.97	C45—H45B	0.97
C11—S1—C31	104.59 (11)	H32A—C32—H32B	107.7
C21—S2—C41	105.20 (12)	C32—C33—C34	113.4 (2)
C16—C11—C12	118.6 (2)	C32—C33—H33A	108.9
C16—C11—S1	124.02 (18)	C34—C33—H33A	108.9
C12—C11—S1	117.38 (19)	C32—C33—H33B	108.9
C13—C12—C11	120.6 (2)	C34—C33—H33B	108.9
C13—C12—H12	119.7	H33A—C33—H33B	107.7
C11—C12—H12	119.7	C35—C34—C33	114.7 (2)
C12—C13—C14	120.8 (2)	C35—C34—H34A	108.6
C12—C13—H13	119.6	C33—C34—H34A	108.6
C14—C13—H13	119.6	C35—C34—H34B	108.6
C13—C14—C15	118.9 (2)	C33—C34—H34B	108.6
C13—C14—H14	120.5	H34A—C34—H34B	107.6
C15—C14—H14	120.5	C34—C35—C35^i	114.7 (3)
C14—C15—C16	120.9 (2)	C34—C35—H35A	108.6
C14—C15—H15	119.6	C35^i—C35—H35A	108.6
C16—C15—H15	119.6	C34—C35—H35B	108.6
C15—C16—C11	120.2 (2)	C35^i—C35—H35B	108.6
C15—C16—H16	119.9	H35A—C35—H35B	107.6
C11—C16—H16	119.9	C42—C41—S2	108.38 (18)
C26—C21—C22	118.8 (2)	C42—C41—H41A	110
C26—C21—S2	124.88 (18)	S2—C41—H41A	110
C22—C21—S2	116.29 (19)	C42—C41—H41B	110
C23—C22—C21	120.4 (2)	S2—C41—H41B	110
C23—C22—H22	119.8	H41A—C41—H41B	108.4
C21—C22—H22	119.8	C43—C42—C41	114.6 (2)
C24—C23—C22	120.6 (2)	C43—C42—H42A	108.6
C24—C23—H23	119.7	C41—C42—H42A	108.6
C22—C23—H23	119.7	C43—C42—H42B	108.6
C23—C24—C25	119.2 (2)	C41—C42—H42B	108.6
C23—C24—H24	120.4	H42A—C42—H42B	107.6
C25—C24—H24	120.4	C42—C43—C44	114.1 (2)
C24—C25—C26	121.4 (2)	C42—C43—H43A	108.7
C24—C25—H25	119.3	C44—C43—H43A	108.7
C26—C25—H25	119.3	C42—C43—H43B	108.7
C25—C26—C21	119.7 (2)	C44—C43—H43B	108.7
C25—C26—H26	120.2	H43A—C43—H43B	107.6
C21—C26—H26	120.2	C45—C44—C43	115.2 (2)
C32—C31—S1	108.72 (18)	C45—C44—H44A	108.5
C32—C31—H31A	109.9	C43—C44—H44A	108.5
S1—C31—H31A	109.9	C45—C44—H44B	108.5
C32—C31—H31B	109.9	C43—C44—H44B	108.5
S1—C31—H31B	109.9	H44A—C44—H44B	107.5
H31A—C31—H31B	108.3	C44—C45—C45^ii	115.0 (3)
C33—C32—C31	113.3 (2)	C44—C45—H45A	108.5
C33—C32—H32A	108.9	C45^ii—C45—H45A	108.5
C31—C32—H32A	108.9	C44—C45—H45B	108.5
C33—C32—H32B	108.9	C45^ii—C45—H45B	108.5
C31—C32—H32B	108.9	H45A—C45—H45B	107.5
C31—S1—C11—C16	−22.2 (2)	C22—C23—C24—C25	0.0 (4)
C31—S1—C11—C12	158.88 (19)	C23—C24—C25—C26	−0.1 (4)
C16—C11—C12—C13	−0.1 (4)	C24—C25—C26—C21	0.0 (4)
S1—C11—C12—C13	178.93 (19)	C22—C21—C26—C25	0.1 (3)
C11—C12—C13—C14	0.8 (4)	S2—C21—C26—C25	−177.32 (18)
C12—C13—C14—C15	−0.9 (4)	C11—S1—C31—C32	−173.08 (17)
C13—C14—C15—C16	0.4 (4)	S1—C31—C32—C33	179.33 (19)
C14—C15—C16—C11	0.2 (4)	C31—C32—C33—C34	179.8 (2)
C12—C11—C16—C15	−0.4 (4)	C32—C33—C34—C35	−179.9 (2)
S1—C11—C16—C15	−179.3 (2)	C33—C34—C35—C35^i	179.8 (3)
C41—S2—C21—C26	−23.1 (2)	C21—S2—C41—C42	−177.11 (17)
C41—S2—C21—C22	159.47 (18)	S2—C41—C42—C43	178.6 (2)
C26—C21—C22—C23	−0.2 (3)	C41—C42—C43—C44	178.7 (2)
S2—C21—C22—C23	177.46 (18)	C42—C43—C44—C45	178.9 (2)
C21—C22—C23—C24	0.1 (4)	C43—C44—C45—C45^ii	179.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···Cg2^iii	0.93	2.88	3.621 (3)	137
C15—H15···Cg2^iv	0.93	2.91	3.638 (3)	136

Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x, −y+2, −z+1.