Do­decane-1,12-di­thiol

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.

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


 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

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Computing details

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)

Crystal data

C12H26S2	Z = 1
Mr = 234.46	F(000) = 130
Triclinic, P1	Dx = 1.099 Mg m^−3
Hall symbol: -P 1	Melting point: 304.4 K
a = 4.221 (1) Å	Cu Kα radiation, λ = 1.5418 Å
b = 5.430 (1) Å	Cell parameters from 22 reflections
c = 15.615 (2) Å	θ = 9.7–21.4°
α = 85.65 (1)°	µ = 3.12 mm^−1
β = 86.68 (2)°	T = 296 K
γ = 83.51 (1)°	Plate, colourless
V = 354.1 (1) Å^3	0.60 × 0.25 × 0.17 mm

Data collection

Rigaku AFC5R diffractometer	Rint = 0.041
ω–2θ scans	θmax = 70.6°
Absorption correction: ψ scan (North et al., 1968)	h = −4→5
Tmin = 0.406, Tmax = 0.589	k = −6→2
1972 measured reflections	l = −19→19
1287 independent reflections	3 standard reflections every 150 reflections
1173 reflections with F^2 > 2σ(F^2)	intensity decay: 9%

Refinement

Refinement on F^2	w = 1/[σ^2(Fo^2) + {0.07[Max(Fo^2,0) + 2Fc^2]/3}^2]
R[F^2 > 2σ(F^2)] = 0.039	(Δ/σ)max < 0.001
wR(F^2) = 0.138	Δρmax = 0.14 e Å^−3
S = 1.67	Δρmin = −0.18 e Å^−3
1287 reflections	Extinction correction: Zachariasen (1967) type 2 Gaussian isotropic
68 parameters	Extinction coefficient: 0.31 (9)
H atoms treated by a mixture of independent and constrained refinement

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
S1	0.8479 (1)	0.21309 (9)	0.57724 (3)	0.0798 (2)
C1	0.6724 (4)	0.4926 (3)	0.62472 (9)	0.0636 (5)
C2	0.5533 (4)	0.4564 (3)	0.71735 (9)	0.0565 (4)
C3	0.4262 (4)	0.6976 (3)	0.75586 (9)	0.0564 (4)
C4	0.3053 (4)	0.6672 (3)	0.84879 (9)	0.0557 (4)
C5	0.1820 (4)	0.9076 (3)	0.88779 (9)	0.0553 (4)
C6	0.0612 (4)	0.8794 (3)	0.98058 (9)	0.0553 (4)
H1a	0.8289	0.6060	0.6217	0.0764*
H1b	0.4970	0.5616	0.5919	0.0764*
H1s	0.642 (6)	0.112 (5)	0.578 (2)	0.0958*
H2a	0.3870	0.3514	0.7203	0.0678*
H2b	0.7248	0.3790	0.7500	0.0678*
H3a	0.5931	0.8022	0.7525	0.0677*
H3b	0.2552	0.7744	0.7229	0.0677*
H4a	0.1367	0.5643	0.8520	0.0668*
H4b	0.4757	0.5885	0.8816	0.0668*
H5a	0.3507	1.0104	0.8844	0.0663*
H5b	0.0116	0.9860	0.8549	0.0663*
H6a	−0.1070	0.7760	0.9854	0.0663*
H6b	0.2303	0.8063	1.0149	0.0663*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
S1	0.1056 (5)	0.0694 (4)	0.0623 (4)	0.0030 (3)	0.0156 (3)	−0.0236 (2)
C1	0.086 (1)	0.0569 (8)	0.0455 (8)	−0.0015 (7)	0.0102 (7)	−0.0082 (6)
C2	0.0736 (10)	0.0523 (8)	0.0427 (8)	−0.0022 (7)	0.0049 (6)	−0.0098 (6)
C3	0.0705 (9)	0.0540 (8)	0.0432 (7)	−0.0016 (6)	0.0052 (6)	−0.0081 (6)
C4	0.0716 (10)	0.0517 (8)	0.0426 (8)	−0.0017 (7)	0.0043 (6)	−0.0091 (6)
C5	0.0701 (9)	0.0518 (8)	0.0426 (7)	−0.0018 (6)	0.0049 (6)	−0.0081 (6)
C6	0.0697 (9)	0.0525 (8)	0.0426 (8)	−0.0026 (7)	0.0048 (6)	−0.0087 (6)

Geometric parameters (Å, º)

S1—C1	1.804 (2)	C2—H2a	0.95
C1—C2	1.509 (2)	C2—H2b	0.95
C2—C3	1.513 (2)	C3—H3a	0.95
C3—C4	1.513 (2)	C3—H3b	0.95
C4—C5	1.508 (2)	C4—H4a	0.95
C5—C6	1.510 (2)	C4—H4b	0.95
C6—C6^i	1.511 (3)	C5—H5a	0.95
S1—H1s	1.08 (3)	C5—H5b	0.95
C1—H1a	0.95	C6—H6a	0.95
C1—H1b	0.95	C6—H6b	0.95
S(1)···S(1)^ii	3.5552 (8)
S1—C1—C2	114.9 (1)	C4—C3—H3a	108.3
C1—C2—C3	113.0 (1)	C4—C3—H3b	108.3
C2—C3—C4	114.2 (1)	H3a—C3—H3b	109.5
C3—C4—C5	114.4 (1)	C3—C4—H4a	108.2
C4—C5—C6	114.8 (1)	C3—C4—H4b	108.2
C5—C6—C6^i	114.6 (1)	C5—C4—H4a	108.2
C1—S1—H1s	100 (1)	C5—C4—H4b	108.2
S1—C1—H1a	108.1	H4a—C4—H4b	109.5
S1—C1—H1b	108.1	C4—C5—H5a	108.1
C2—C1—H1a	108.1	C4—C5—H5b	108.1
C2—C1—H1b	108.1	C6—C5—H5a	108.1
H1a—C1—H1b	109.5	C6—C5—H5b	108.1
C1—C2—H2a	108.6	H5a—C5—H5b	109.5
C1—C2—H2b	108.6	C5—C6—H6a	109.5
C3—C2—H2a	108.6	C5—C6—H6b	109.5
C3—C2—H2b	108.6	C6^i—C6—H6a	107.8
H2a—C2—H2b	109.5	C6^i—C6—H6b	105.8
C2—C3—H3a	108.3	H6a—C6—H6b	109.5
C2—C3—H3b	108.3
S1—C1—C2—C3	176.6 (1)	C4—C5—C6—C6^i	179.9 (2)
C1—C2—C3—C4	−180.0 (1)	C5—C6—C6^i—C5^i	−180.0
C2—C3—C4—C5	179.3 (1)	C2—C1—S1—H1s	65 (1)
C3—C4—C5—C6	−179.9 (1)

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