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In the molecular structure of the title compound, C12H26S2, the hydro­carbon skeleton has an all-trans conformation. The terminal S-H bond is in the 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 as in the smectic C layer structure of liquid crystals. The mercapto groups do not form hydrogen bonds. These features are similar to those of the homologues with an even number of C atoms containing more than four C atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680100719X/ci6027sup1.cif
Contains datablocks General, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680100719X/ci6027Isup2.hkl
Contains datablock I

CCDC reference: 170297

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.039
  • wR factor = 0.138
  • Data-to-parameter ratio = 18.9

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_420 Alert C D-H Without Acceptor S(1) - H(1S) ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Computing details top

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: MULTAN88 (Debaerdemaeker et al., 1988); program(s) used to refine structure: TEXSAN; software used to prepare material for publication: TEXSAN.

(I) top
Crystal data top
C12H26S2Z = 1
Mr = 234.46F(000) = 130
Triclinic, P1Dx = 1.099 Mg m3
Hall symbol: -P 1Melting point: 304.4 K
a = 4.221 (1) ÅCu Kα radiation, λ = 1.5418 Å
b = 5.430 (1) ÅCell parameters from 22 reflections
c = 15.615 (2) Åθ = 9.7–21.4°
α = 85.65 (1)°µ = 3.12 mm1
β = 86.68 (2)°T = 296 K
γ = 83.51 (1)°Plate, colourless
V = 354.1 (1) Å30.60 × 0.25 × 0.17 mm
Data collection top
Rigaku AFC5R
diffractometer
Rint = 0.041
ω–2θ scansθmax = 70.6°
Absorption correction: ψ scan
(North et al., 1968)
h = 45
Tmin = 0.406, Tmax = 0.589k = 62
1972 measured reflectionsl = 1919
1287 independent reflections3 standard reflections every 150 reflections
1173 reflections with F2 > 2σ(F2) intensity decay: 9%
Refinement top
Refinement on F2 w = 1/[σ2(Fo2) + {0.07[Max(Fo2,0) + 2Fc2]/3}2]
R[F2 > 2σ(F2)] = 0.039(Δ/σ)max < 0.001
wR(F2) = 0.138Δρmax = 0.14 e Å3
S = 1.67Δρmin = 0.18 e Å3
1287 reflectionsExtinction correction: Zachariasen (1967) type 2 Gaussian isotropic
68 parametersExtinction coefficient: 0.31 (9)
H atoms treated by a mixture of independent and constrained refinement
Special details top

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
xyzUiso*/Ueq
S10.8479 (1)0.21309 (9)0.57724 (3)0.0798 (2)
C10.6724 (4)0.4926 (3)0.62472 (9)0.0636 (5)
C20.5533 (4)0.4564 (3)0.71735 (9)0.0565 (4)
C30.4262 (4)0.6976 (3)0.75586 (9)0.0564 (4)
C40.3053 (4)0.6672 (3)0.84879 (9)0.0557 (4)
C50.1820 (4)0.9076 (3)0.88779 (9)0.0553 (4)
C60.0612 (4)0.8794 (3)0.98058 (9)0.0553 (4)
H1a0.82890.60600.62170.0764*
H1b0.49700.56160.59190.0764*
H1s0.642 (6)0.112 (5)0.578 (2)0.0958*
H2a0.38700.35140.72030.0678*
H2b0.72480.37900.75000.0678*
H3a0.59310.80220.75250.0677*
H3b0.25520.77440.72290.0677*
H4a0.13670.56430.85200.0668*
H4b0.47570.58850.88160.0668*
H5a0.35071.01040.88440.0663*
H5b0.01160.98600.85490.0663*
H6a0.10700.77600.98540.0663*
H6b0.23030.80631.01490.0663*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.1056 (5)0.0694 (4)0.0623 (4)0.0030 (3)0.0156 (3)0.0236 (2)
C10.086 (1)0.0569 (8)0.0455 (8)0.0015 (7)0.0102 (7)0.0082 (6)
C20.0736 (10)0.0523 (8)0.0427 (8)0.0022 (7)0.0049 (6)0.0098 (6)
C30.0705 (9)0.0540 (8)0.0432 (7)0.0016 (6)0.0052 (6)0.0081 (6)
C40.0716 (10)0.0517 (8)0.0426 (8)0.0017 (7)0.0043 (6)0.0091 (6)
C50.0701 (9)0.0518 (8)0.0426 (7)0.0018 (6)0.0049 (6)0.0081 (6)
C60.0697 (9)0.0525 (8)0.0426 (8)0.0026 (7)0.0048 (6)0.0087 (6)
Geometric parameters (Å, º) top
S1—C11.804 (2)C2—H2a0.95
C1—C21.509 (2)C2—H2b0.95
C2—C31.513 (2)C3—H3a0.95
C3—C41.513 (2)C3—H3b0.95
C4—C51.508 (2)C4—H4a0.95
C5—C61.510 (2)C4—H4b0.95
C6—C6i1.511 (3)C5—H5a0.95
S1—H1s1.08 (3)C5—H5b0.95
C1—H1a0.95C6—H6a0.95
C1—H1b0.95C6—H6b0.95
S(1)···S(1)ii3.5552 (8)
S1—C1—C2114.9 (1)C4—C3—H3a108.3
C1—C2—C3113.0 (1)C4—C3—H3b108.3
C2—C3—C4114.2 (1)H3a—C3—H3b109.5
C3—C4—C5114.4 (1)C3—C4—H4a108.2
C4—C5—C6114.8 (1)C3—C4—H4b108.2
C5—C6—C6i114.6 (1)C5—C4—H4a108.2
C1—S1—H1s100 (1)C5—C4—H4b108.2
S1—C1—H1a108.1H4a—C4—H4b109.5
S1—C1—H1b108.1C4—C5—H5a108.1
C2—C1—H1a108.1C4—C5—H5b108.1
C2—C1—H1b108.1C6—C5—H5a108.1
H1a—C1—H1b109.5C6—C5—H5b108.1
C1—C2—H2a108.6H5a—C5—H5b109.5
C1—C2—H2b108.6C5—C6—H6a109.5
C3—C2—H2a108.6C5—C6—H6b109.5
C3—C2—H2b108.6C6i—C6—H6a107.8
H2a—C2—H2b109.5C6i—C6—H6b105.8
C2—C3—H3a108.3H6a—C6—H6b109.5
C2—C3—H3b108.3
S1—C1—C2—C3176.6 (1)C4—C5—C6—C6i179.9 (2)
C1—C2—C3—C4180.0 (1)C5—C6—C6i—C5i180.0
C2—C3—C4—C5179.3 (1)C2—C1—S1—H1s65 (1)
C3—C4—C5—C6179.9 (1)
Symmetry codes: (i) x, y+2, z+2; (ii) x+2, y, z+1.
 

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