In the title structure, C
22H
30S
2,
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.
Supporting information
CCDC reference: 282531
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (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
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
top
Crystal data top
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) Å3 | |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0908P)2] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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—C35i | 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—C45ii | 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—C35i | 114.7 (3) |
C14—C15—C16 | 120.9 (2) | C34—C35—H35A | 108.6 |
C14—C15—H15 | 119.6 | C35i—C35—H35A | 108.6 |
C16—C15—H15 | 119.6 | C34—C35—H35B | 108.6 |
C15—C16—C11 | 120.2 (2) | C35i—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—C45ii | 115.0 (3) |
C33—C32—C31 | 113.3 (2) | C44—C45—H45A | 108.5 |
C33—C32—H32A | 108.9 | C45ii—C45—H45A | 108.5 |
C31—C32—H32A | 108.9 | C44—C45—H45B | 108.5 |
C33—C32—H32B | 108.9 | C45ii—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—C35i | 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—C45ii | 179.4 (3) |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z+2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C12—H12···Cg2iii | 0.93 | 2.88 | 3.621 (3) | 137 |
C15—H15···Cg2iv | 0.93 | 2.91 | 3.638 (3) | 136 |
Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) −x, −y+2, −z+1. |