In the molecular structure of the title compound, C20H42S2, (I), the skeleton of the hydrocarbon has an all-trans conformation. The terminal S-H bond is in a gauche conformation with respect to the skeleton. In the crystal structure, the molecules are arranged along the c axis, the longest axis, forming layers in which the long axis of the molecule is inclined to the layer plane. This packing is very similar to that of the smectic C structure of liquid crystals. Except for the length of the c axis, no big difference was observed between the crystal data obtained here and those of homologues with even numbers of C atoms already reported.
Supporting information
CCDC reference: 170296
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.057
- wR factor = 0.159
- Data-to-parameter ratio = 19.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level A:
ABSTM_02 Alert A Test not performed as the _exptl_absorpt_correction_type
has not been identified. See test ABSTY_01.
ABSTY_01 Alert A The absorption correction should be one of the following
* none
* analytical
* integration
* numerical
* gaussian
* empirical
* psi-scan
* multi-scan
* refdelf
* sphere
* cylinder
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor S(1) - H(1S) ?
2 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1992); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 2000); program(s) used to solve structure: SAPI91 (Fan, 1991); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.
Crystal data top
C20H42S2 | Z = 1 |
Mr = 346.67 | Dx = 1.063 Mg m−3 |
Triclinic, P1 | Cu Kα radiation, λ = 1.5418 Å |
a = 4.2261 (6) Å | Cell parameters from 24 reflections |
b = 5.4283 (6) Å | θ = 9.8–17.5° |
c = 23.819 (3) Å | µ = 2.17 mm−1 |
α = 87.43 (1)° | T = 296 K |
β = 86.56 (1)° | Plate, colorless |
γ = 83.37 (1)° | 0.7 × 0.15 × 0.01 mm |
V = 541.4 (1) Å3 | |
Data collection top
Rigaku AFC-5R diffractometer | Rint = 0.045 |
ω scans | θmax = 70.5° |
Absorption correction: ψ (North et al., 1968) | h = −4→5 |
Tmin = 0.767, Tmax = 0.996 | k = −6→2 |
3008 measured reflections | l = −29→29 |
1967 independent reflections | 2 standard reflections every 150 reflections |
1453 reflections with F2 > 2σ(F2) | intensity decay: 11.8% |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + {0.05[Max(Fo2,0) + 2Fc2]/3}2] |
wR(F2) = 0.159 | (Δ/σ)max = 0.001 |
S = 1.77 | Δρmax = 0.15 e Å−3 |
1966 reflections | Δρmin = −0.35 e Å−3 |
103 parameters | |
Special details top
Geometry. none |
Refinement. Refinement using reflections with F2 > -3.0 σ(F2). The
weighted R-factor (wR) and goodness of fit (S) are based
on F2. R-factor (gt) are based on F. The threshold
expression of F2 > 2.0 σ(F2) is used only for calculating
R-factor (gt). |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
S1 | 1.3470 (2) | −0.2802 (1) | 0.05060 (3) | 0.0784 (2) | |
C1 | 1.1699 (6) | 0.0041 (5) | 0.08170 (10) | 0.0626 (7) | |
C2 | 1.0508 (6) | −0.0239 (5) | 0.14241 (9) | 0.0563 (7) | |
C3 | 0.9202 (6) | 0.2219 (4) | 0.16753 (9) | 0.0534 (6) | |
C4 | 0.7989 (6) | 0.1982 (4) | 0.22849 (9) | 0.0546 (7) | |
C5 | 0.6752 (6) | 0.4440 (4) | 0.25398 (9) | 0.0530 (6) | |
C6 | 0.5533 (6) | 0.4242 (4) | 0.31487 (9) | 0.0531 (6) | |
C7 | 0.4287 (6) | 0.6702 (4) | 0.34032 (9) | 0.0524 (6) | |
C8 | 0.3073 (6) | 0.6504 (4) | 0.40118 (9) | 0.0520 (6) | |
C9 | 0.1840 (6) | 0.8966 (4) | 0.42645 (9) | 0.0523 (6) | |
C10 | 0.0616 (6) | 0.8770 (4) | 0.48742 (9) | 0.0519 (6) | |
H1a | 1.3258 | 0.1176 | 0.0796 | 0.0752* | |
H1b | 0.9946 | 0.0700 | 0.0604 | 0.0752* | |
H1s | 1.122 (8) | −0.393 (6) | 0.050 (1) | 0.0942* | |
H2a | 0.8860 | −0.1296 | 0.1445 | 0.0675* | |
H2b | 1.2226 | −0.0971 | 0.1637 | 0.0675* | |
H3a | 1.0856 | 0.3272 | 0.1653 | 0.0641* | |
H3b | 0.7490 | 0.2948 | 0.1460 | 0.0641* | |
H4a | 0.6305 | 0.0959 | 0.2306 | 0.0655* | |
H4b | 0.9689 | 0.1220 | 0.2498 | 0.0655* | |
H5a | 0.8440 | 0.5462 | 0.2517 | 0.0636* | |
H5b | 0.5054 | 0.5199 | 0.2325 | 0.0636* | |
H6a | 0.3849 | 0.3218 | 0.3172 | 0.0638* | |
H6b | 0.7232 | 0.3488 | 0.3363 | 0.0638* | |
H7a | 0.5970 | 0.7728 | 0.3379 | 0.0630* | |
H7b | 0.2586 | 0.7455 | 0.3189 | 0.0630* | |
H8a | 0.1386 | 0.5483 | 0.4036 | 0.0624* | |
H8b | 0.4772 | 0.5748 | 0.4226 | 0.0624* | |
H9a | 0.3529 | 0.9986 | 0.4241 | 0.0628* | |
H9b | 0.0144 | 0.9724 | 0.4049 | 0.0628* | |
H10a | −0.1111 | 0.7787 | 0.4905 | 0.0624* | |
H10b | 0.2284 | 0.8018 | 0.5097 | 0.0624* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
S1 | 0.0960 (6) | 0.0717 (5) | 0.0627 (4) | 0.0077 (4) | 0.0184 (3) | −0.0224 (3) |
C1 | 0.075 (2) | 0.063 (1) | 0.046 (1) | 0.002 (1) | 0.010 (1) | −0.009 (1) |
C2 | 0.065 (1) | 0.059 (1) | 0.041 (1) | 0.004 (1) | 0.006 (1) | −0.0066 (10) |
C3 | 0.060 (1) | 0.054 (1) | 0.043 (1) | 0.004 (1) | 0.0075 (10) | −0.0077 (9) |
C4 | 0.062 (1) | 0.056 (1) | 0.042 (1) | 0.005 (1) | 0.007 (1) | −0.0079 (10) |
C5 | 0.060 (1) | 0.055 (1) | 0.041 (1) | 0.004 (1) | 0.0071 (10) | −0.0080 (9) |
C6 | 0.062 (1) | 0.054 (1) | 0.040 (1) | 0.003 (1) | 0.007 (1) | −0.0082 (9) |
C7 | 0.060 (1) | 0.054 (1) | 0.040 (1) | 0.004 (1) | 0.0064 (10) | −0.0079 (9) |
C8 | 0.060 (1) | 0.052 (1) | 0.040 (1) | 0.005 (1) | 0.0066 (10) | −0.0083 (9) |
C9 | 0.060 (1) | 0.053 (1) | 0.041 (1) | 0.004 (1) | 0.0080 (10) | −0.0084 (9) |
C10 | 0.059 (1) | 0.054 (1) | 0.039 (1) | 0.005 (1) | 0.0061 (10) | −0.0071 (10) |
Geometric parameters (Å, º) top
S1—C1 | 1.806 (3) | C6—C7 | 1.516 (3) |
C1—C2 | 1.509 (3) | C7—C8 | 1.512 (3) |
C2—C3 | 1.518 (3) | C8—C9 | 1.514 (3) |
C3—C4 | 1.515 (3) | C9—C10 | 1.515 (3) |
C4—C5 | 1.515 (3) | C10—C10i | 1.512 (4) |
C5—C6 | 1.513 (3) | | |
| | | |
S1—C1—C2 | 114.8 (2) | C5—C6—C7 | 114.6 (2) |
C1—C2—C3 | 112.8 (2) | C6—C7—C8 | 114.6 (2) |
C2—C3—C4 | 113.8 (2) | C7—C8—C9 | 114.4 (2) |
C3—C4—C5 | 113.8 (2) | C8—C9—C10 | 114.4 (2) |
C4—C5—C6 | 114.6 (2) | C9—C10—C10i | 114.3 (2) |
| | | |
C2—C1—S1—H1s | 67 (1) | | |
Symmetry code: (i) −x, −y+2, −z+1. |