1,2-Bis(undecyl­sulfan­yl)benzene

Tomiyama, E.; Miyamura, K.

doi:10.1107/S1600536808014712

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1119

doi:10.1107/S1600536808014712

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1,2-Bis(undecylsulfanyl)benzene

Etsuko Tomiyama ^a ^* and Kazuo Miyamura ^a

^aDepartment of Chemistry, Faculty of Science, Tokyo University of Science, Kagurazaka 1-3, Shinjuku-ku, Tokyo 162-8601, Japan
^*Correspondence e-mail: j1306709@ed.kagu.tus.ac.jp

(Received 4 May 2008; accepted 15 May 2008; online 21 May 2008)

In the title compound, C₂₈H₅₀S₂, the alkyl chains adopt a fully extended all-trans conformation and each of them is almost perfectly planar. One of the alkyl chains is coplanar with the benzene ring and the other is twisted out of the benzene ring plane; the C—C—S—C torsion angles are 176.4 (2) and 80.8 (3)°. In the crystal structure, an intermolecular S⋯S interaction [3.2123 (13) Å] links the molecules into a centrosymmetric dimer; dimers are linked through weak C—H⋯π and C—H⋯S interactions, forming a column along the a axis.

Related literature

For related literature, see: Alves et al. (2004 ); Huynh et al. (2002 ); Liu et al. (2007 ); Robertson & Cronin (2002 ); Salvatore et al. (2005 ); Tomiyama et al. (2007 ).

Experimental

Crystal data

C₂₈H₅₀S₂
M_r = 450.80
Monoclinic, P 2₁ /c
a = 5.4024 (10) Å
b = 16.863 (3) Å
c = 29.611 (5) Å
β = 91.245 (3)°
V = 2696.9 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 100 (1) K
0.55 × 0.11 × 0.10 mm

Data collection

Bruker SMART APEX CCD-detector diffractometer
Absorption correction: analytical (XPREP; Bruker 2000 ) T_min = 0.901, T_max = 0.991
15683 measured reflections
5958 independent reflections
4452 reflections with I > 2σ(I)
R_int = 0.086

Refinement

R[F² > 2σ(F²)] = 0.087
wR(F²) = 0.205
S = 1.14
5958 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.75 e Å⁻³
Δρ_min = −0.55 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18B⋯S1ⁱ	0.99	2.99	3.749 (4)	134
C7—H7A⋯Cgⁱⁱ	0.99	2.67	3.567 (16)	151
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z. Cg is the centroid of the C1–C6 ring.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97, KENX (Sakai, 2002 ), ORTEPIII and Mercury.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808014712/ci2597sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808014712/ci2597Isup2.hkl

checkCIF report

Comment top

Thioethers have emerged as preeminent classes of organic compounds, which hold useful applications as key reagents in organic synthesis, bio-organic, mechanical, and heterocyclic chemistry. The coordination chemistry of dithiolate ligands has also been extensively studied (Liu et al., 2007; Alves et al., 2004; Huynh et al., 2002). In recent years, transition metal bis(dithiolene) complexes, with square-planar coordination geometry, have been used widely as building blocks for conducting and magnetic materials (Robertson & Cronin, 2002). We previously reported the crystal structure of a dithiolate complex salt (Tomiyama et al., 2007). In order to explore crystal structures of new dithiole compounds and to gain more insight into the structure-regulating ability of intermolecular S···S, C—H···S interactions, the title compound was synthesized and its structure was analysized by X-ray analysis.

The structure of the title molecule is shown in Fig. 1. The alkyl chains are in the fully extended all-trans conformation and each alkyl chain is almost perfectly planar. The C8—C7—S1—C1 and C19—C18—S2—C6 torsion angles of 176.4 (2)° and 80.8 (3)°, respectively, indicate that non-hydrogen atoms of one of the side chains is coplanar with the benzene ring, and the other chain is twisted out of the benzene plane.

In the crystal structure, an intermolecular S···S interaction [S2···S2(1-x,-y,1-z) = 3.2123 (13) Å] shorter than 3.70 Å, the sum of van der Waals radii, links the molecules into a centrosymmetric dimer (Fig. 2). The dimers are linked through weak C—H···π (between C7—H7A and benzene ring) and C—H···S interactions (Table 1) to form a column along the a axis.

Related literature top

For related literature, see: Alves et al. (2004); Huynh et al. (2002); Liu et al. (2007); Robertson & Cronin (2002); Salvatore et al. (2005); Tomiyama et al. (2007). Cg1 is the centroid of the C1–C6 ring.

Experimental top

All starting materials were of reagent grade and used without further purification. 1,2-Bis(undecylthio)benzene was prepared by a literature procedure (Salvatore et al., 2005): Benzene-1,2-dithiol (1 mmol) was stirred under argon atmosphere at temperature for 1 h in the presence of caesium carbonate (2.2 mmol), tetrabutylammonium iodide (TBAI; 2.2 mmol) and anhydrous DMF. The reaction mixture was subsequently cooled to 273 K, added with undecylbromide (2.2 mmol), and the reaction mixture stirred for 2 h and then allowed to return to room temperature. The title compound was obtained by slow evaporation method from the reaction mixture at room temperature. White needle-shaped crystals of suitable size for X-ray diffraction were obtained. ¹H NMR (CDCl₃): δ 0.88 (t, J = 6.7, 6H), 1.26–1.44 (m, 32H), 1.66 (quin, J = 7.3, 4H), 2.90 (t, J = 7.4, 4H), 7.11–7.14 (m, 2H), 7.24–7.27 (m, 2H). ¹³C NMR (CDCl₃): δ 14.1, 22.7, 28.8, 29.0, 29.2, 29.3, 29.5, 29.6, 31.9, 33.2, 125.9, 128.5, 137.2.

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), KENX (Sakai, 2002), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. An ORTEPIII (Burnett & Johnson, 1996) view of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A partial packing diagram of the title compound, showing symmetrically paired molecules. S···S interactions are shown by dashed lines.

1,2-Bis(undecylsulfanyl)benzene top

Crystal data top

C₂₈H₅₀S₂	F(000) = 1000
M_r = 450.80	D_x = 1.110 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3006 reflections
a = 5.4024 (10) Å	θ = 2.4–27.7°
b = 16.863 (3) Å	µ = 0.21 mm⁻¹
c = 29.611 (5) Å	T = 100 K
β = 91.245 (3)°	Needle, white
V = 2696.9 (8) Å³	0.55 × 0.11 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD-detector diffractometer	5958 independent reflections
Radiation source: fine-focus sealed tube	4452 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.086
Detector resolution: 8.366 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scans	h = −6→5
Absorption correction: analytical (XPREP; Bruker 2000)	k = −21→21
T_min = 0.901, T_max = 0.991	l = −24→37
15683 measured reflections

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)] = 0.088	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.205	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0976P)²] where P = (F_o² + 2F_c²)/3
5958 reflections	(Δ/σ)_max = 0.001
273 parameters	Δρ_max = 0.75 e Å⁻³
0 restraints	Δρ_min = −0.55 e Å⁻³

Crystal data top

C₂₈H₅₀S₂	V = 2696.9 (8) Å³
M_r = 450.80	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 5.4024 (10) Å	µ = 0.21 mm⁻¹
b = 16.863 (3) Å	T = 100 K
c = 29.611 (5) Å	0.55 × 0.11 × 0.10 mm
β = 91.245 (3)°

Data collection top

Bruker SMART APEX CCD-detector diffractometer	5958 independent reflections
Absorption correction: analytical (XPREP; Bruker 2000)	4452 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.991	R_int = 0.086
15683 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.088	0 restraints
wR(F²) = 0.205	H-atom parameters constrained
S = 1.14	Δρ_max = 0.75 e Å⁻³
5958 reflections	Δρ_min = −0.55 e Å⁻³
273 parameters

Special details top

Experimental. The first 50 frames were rescanned at the end of data collection to evaluate any possible decay phenomenon. Since it was judged to be negligible, no decay correction was applied to the data.

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.

Mean-plane data from final SHELXL refinement run:-

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

- 3.2338 (0.0068) x - 0.2627 (0.0262) y + 24.0951 (0.0272) z = 10.3067 (0.0188)

* -0.0131 (0.0025) C1 * 0.0083 (0.0027) C2 * 0.0004 (0.0029) C3 * -0.0044 (0.0028) C4 * -0.0004 (0.0026) C5 * 0.0092 (0.0026) C6

Rms deviation of fitted atoms = 0.0076

1.5719 (0.0210) x + 16.1263 (0.0188) y + 0.6605 (0.0846) z = 2.7127 (0.0343)

Angle to previous plane (with approximate e.s.d.) = 80.44 (0.21)

* 0.0000 (0.0001) S2 * 0.0000 (0.0000) C18 * 0.0000 (0.0000) C19

Rms deviation of fitted atoms = 0.0000

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	U_iso*/U_eq
C1	0.3636 (6)	0.23339 (18)	0.47850 (11)	0.0143 (7)
C2	0.3445 (6)	0.31584 (19)	0.47775 (11)	0.0177 (7)
H2	0.2129	0.3404	0.4611	0.021*
C3	0.5152 (6)	0.36204 (19)	0.50091 (12)	0.0206 (8)
H3	0.5028	0.4182	0.4998	0.025*
C4	0.7044 (6)	0.3267 (2)	0.52580 (11)	0.0196 (7)
H4	0.8218	0.3588	0.5417	0.024*
C5	0.7236 (6)	0.24514 (19)	0.52766 (11)	0.0172 (7)
H5	0.8540	0.2213	0.5449	0.021*
C6	0.5529 (6)	0.19786 (18)	0.50448 (10)	0.0126 (6)
C7	−0.0418 (6)	0.23663 (19)	0.41612 (11)	0.0161 (7)
H7A	−0.1406	0.2689	0.4370	0.019*
H7B	0.0570	0.2729	0.3973	0.019*
C8	−0.2111 (6)	0.18638 (19)	0.38639 (11)	0.0156 (7)
H8A	−0.3070	0.1502	0.4057	0.019*
H8B	−0.1091	0.1534	0.3663	0.019*
C9	−0.3894 (6)	0.23563 (19)	0.35769 (11)	0.0160 (7)
H9A	−0.4946	0.2674	0.3778	0.019*
H9B	−0.2933	0.2730	0.3391	0.019*
C10	−0.5543 (6)	0.18594 (19)	0.32679 (11)	0.0166 (7)
H10A	−0.6531	0.1496	0.3455	0.020*
H10B	−0.4486	0.1531	0.3073	0.020*
C11	−0.7305 (6)	0.23463 (19)	0.29673 (11)	0.0165 (7)
H11A	−0.8384	0.2668	0.3162	0.020*
H11B	−0.6320	0.2716	0.2784	0.020*
C12	−0.8924 (6)	0.1844 (2)	0.26526 (11)	0.0175 (7)
H12A	−0.7845	0.1524	0.2458	0.021*
H12B	−0.9904	0.1473	0.2836	0.021*
C13	−1.0683 (6)	0.23277 (19)	0.23545 (11)	0.0171 (7)
H13A	−1.1768	0.2645	0.2550	0.021*
H13B	−0.9702	0.2702	0.2173	0.021*
C14	−1.2293 (6)	0.18315 (19)	0.20373 (11)	0.0167 (7)
H14A	−1.3252	0.1451	0.2219	0.020*
H14B	−1.1208	0.1521	0.1838	0.020*
C15	−1.4082 (6)	0.2314 (2)	0.17450 (11)	0.0174 (7)
H15A	−1.3129	0.2701	0.1567	0.021*
H15B	−1.5193	0.2616	0.1943	0.021*
C16	−1.5645 (6)	0.1807 (2)	0.14234 (11)	0.0203 (8)
H16A	−1.6564	0.1411	0.1601	0.024*
H16B	−1.4533	0.1514	0.1221	0.024*
C17	−1.7491 (7)	0.2284 (2)	0.11360 (12)	0.0247 (8)
H17A	−1.8648	0.2558	0.1333	0.037*
H17B	−1.8413	0.1926	0.0933	0.037*
H17C	−1.6598	0.2675	0.0957	0.037*
C18	0.8229 (6)	0.06584 (19)	0.53962 (10)	0.0147 (7)
H18A	0.8749	0.0117	0.5311	0.018*
H18B	0.9610	0.1021	0.5327	0.018*
C19	0.7839 (6)	0.06751 (19)	0.58997 (11)	0.0151 (7)
H19A	0.6565	0.0280	0.5979	0.018*
H19B	0.7241	0.1206	0.5990	0.018*
C20	1.0263 (6)	0.04874 (19)	0.61545 (11)	0.0169 (7)
H20A	1.0864	−0.0037	0.6055	0.020*
H20B	1.1518	0.0886	0.6071	0.020*
C21	1.0057 (6)	0.04781 (19)	0.66646 (11)	0.0182 (7)
H21A	0.9020	0.0022	0.6753	0.022*
H21B	0.9214	0.0969	0.6762	0.022*
C22	1.2558 (6)	0.0419 (2)	0.69080 (11)	0.0172 (7)
H22A	1.3383	−0.0074	0.6811	0.021*
H22B	1.3597	0.0870	0.6813	0.021*
C23	1.2446 (6)	0.04204 (19)	0.74200 (11)	0.0190 (7)
H23A	1.1481	−0.0046	0.7517	0.023*
H23B	1.1555	0.0902	0.7518	0.023*
C24	1.4977 (6)	0.0400 (2)	0.76552 (11)	0.0182 (7)
H24A	1.5864	−0.0082	0.7558	0.022*
H24B	1.5943	0.0865	0.7556	0.022*
C25	1.4887 (6)	0.0404 (2)	0.81672 (11)	0.0188 (7)
H25A	1.3865	−0.0049	0.8266	0.023*
H25B	1.4065	0.0897	0.8266	0.023*
C26	1.7422 (6)	0.0350 (2)	0.83994 (11)	0.0194 (7)
H26A	1.8269	−0.0133	0.8292	0.023*
H26B	1.8421	0.0813	0.8309	0.023*
C27	1.7338 (7)	0.0323 (2)	0.89105 (12)	0.0243 (8)
H27A	1.6665	0.0831	0.9022	0.029*
H27B	1.6197	−0.0105	0.9001	0.029*
C28	1.9854 (7)	0.0181 (2)	0.91318 (13)	0.0298 (9)
H28A	2.0508	−0.0330	0.9031	0.045*
H28B	1.9693	0.0176	0.9461	0.045*
H28C	2.0989	0.0606	0.9046	0.045*
S1	0.16106 (14)	0.17012 (5)	0.44775 (3)	0.0151 (2)
S2	0.55814 (15)	0.09312 (5)	0.50441 (3)	0.0171 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0147 (16)	0.0167 (16)	0.0114 (17)	−0.0035 (13)	−0.0017 (12)	0.0033 (13)
C2	0.0188 (17)	0.0186 (17)	0.0156 (18)	0.0018 (14)	−0.0028 (13)	0.0007 (14)
C3	0.0254 (18)	0.0135 (17)	0.0228 (19)	0.0004 (14)	−0.0050 (14)	−0.0015 (14)
C4	0.0227 (17)	0.0221 (18)	0.0137 (17)	−0.0030 (14)	−0.0066 (13)	−0.0013 (14)
C5	0.0180 (17)	0.0187 (17)	0.0149 (17)	0.0012 (13)	−0.0027 (13)	0.0018 (13)
C6	0.0147 (15)	0.0123 (15)	0.0109 (16)	−0.0034 (12)	−0.0017 (12)	0.0021 (12)
C7	0.0131 (16)	0.0191 (17)	0.0160 (18)	0.0021 (13)	−0.0040 (12)	0.0025 (13)
C8	0.0166 (16)	0.0161 (16)	0.0139 (17)	0.0007 (13)	−0.0045 (13)	−0.0011 (13)
C9	0.0153 (16)	0.0156 (16)	0.0169 (18)	0.0011 (13)	−0.0027 (13)	0.0024 (13)
C10	0.0137 (16)	0.0195 (17)	0.0163 (18)	0.0010 (13)	−0.0050 (13)	−0.0014 (13)
C11	0.0141 (16)	0.0189 (17)	0.0163 (18)	−0.0008 (13)	−0.0022 (13)	0.0003 (13)
C12	0.0157 (16)	0.0210 (18)	0.0157 (18)	−0.0016 (13)	−0.0041 (13)	0.0011 (14)
C13	0.0144 (16)	0.0204 (17)	0.0164 (18)	−0.0026 (13)	−0.0041 (13)	0.0013 (14)
C14	0.0155 (16)	0.0190 (17)	0.0155 (18)	−0.0002 (13)	−0.0038 (13)	0.0006 (13)
C15	0.0155 (16)	0.0211 (17)	0.0153 (18)	−0.0014 (13)	−0.0058 (13)	0.0030 (13)
C16	0.0206 (17)	0.0234 (18)	0.0165 (18)	−0.0009 (14)	−0.0083 (14)	0.0005 (14)
C17	0.0254 (19)	0.029 (2)	0.0190 (19)	0.0005 (15)	−0.0125 (15)	0.0036 (15)
C18	0.0125 (15)	0.0175 (16)	0.0139 (17)	−0.0016 (13)	−0.0055 (12)	0.0001 (13)
C19	0.0159 (16)	0.0152 (16)	0.0141 (17)	0.0024 (13)	−0.0033 (12)	0.0016 (13)
C20	0.0173 (16)	0.0176 (17)	0.0157 (18)	0.0003 (13)	−0.0054 (13)	−0.0002 (13)
C21	0.0222 (17)	0.0167 (17)	0.0154 (18)	0.0014 (14)	−0.0043 (14)	0.0030 (13)
C22	0.0204 (17)	0.0181 (17)	0.0128 (17)	0.0009 (13)	−0.0070 (13)	−0.0017 (13)
C23	0.0228 (18)	0.0155 (16)	0.0184 (19)	0.0007 (14)	−0.0061 (14)	0.0017 (13)
C24	0.0208 (17)	0.0181 (17)	0.0153 (18)	0.0010 (14)	−0.0071 (13)	0.0001 (13)
C25	0.0218 (18)	0.0183 (17)	0.0160 (18)	0.0014 (14)	−0.0052 (14)	0.0020 (13)
C26	0.0244 (18)	0.0154 (16)	0.0180 (19)	0.0018 (14)	−0.0090 (14)	−0.0032 (14)
C27	0.030 (2)	0.0217 (18)	0.020 (2)	0.0010 (15)	−0.0054 (15)	0.0003 (15)
C28	0.039 (2)	0.029 (2)	0.020 (2)	0.0013 (17)	−0.0158 (17)	0.0016 (16)
S1	0.0137 (4)	0.0177 (4)	0.0135 (4)	−0.0001 (3)	−0.0076 (3)	0.0013 (3)
S2	0.0189 (4)	0.0147 (4)	0.0173 (5)	−0.0011 (3)	−0.0110 (3)	0.0021 (3)

Geometric parameters (Å, º) top

C1—C2	1.394 (4)	C16—C17	1.526 (4)
C1—C6	1.401 (4)	C16—H16A	0.99
C1—S1	1.767 (3)	C16—H16B	0.99
C2—C3	1.379 (4)	C17—H17A	0.98
C2—H2	0.95	C17—H17B	0.98
C3—C4	1.382 (4)	C17—H17C	0.98
C3—H3	0.95	C18—C19	1.511 (4)
C4—C5	1.381 (4)	C18—S2	1.811 (3)
C4—H4	0.95	C18—H18A	0.99
C5—C6	1.389 (4)	C18—H18B	0.99
C5—H5	0.95	C19—C20	1.530 (4)
C6—S2	1.766 (3)	C19—H19A	0.99
C7—C8	1.515 (4)	C19—H19B	0.99
C7—S1	1.814 (3)	C20—C21	1.517 (4)
C7—H7A	0.99	C20—H20A	0.99
C7—H7B	0.99	C20—H20B	0.99
C8—C9	1.518 (4)	C21—C22	1.521 (4)
C8—H8A	0.99	C21—H21A	0.99
C8—H8B	0.99	C21—H21B	0.99
C9—C10	1.516 (4)	C22—C23	1.519 (5)
C9—H9A	0.99	C22—H22A	0.99
C9—H9B	0.99	C22—H22B	0.99
C10—C11	1.528 (4)	C23—C24	1.522 (4)
C10—H10A	0.99	C23—H23A	0.99
C10—H10B	0.99	C23—H23B	0.99
C11—C12	1.521 (4)	C24—C25	1.518 (4)
C11—H11A	0.99	C24—H24A	0.99
C11—H11B	0.99	C24—H24B	0.99
C12—C13	1.520 (4)	C25—C26	1.521 (4)
C12—H12A	0.99	C25—H25A	0.99
C12—H12B	0.99	C25—H25B	0.99
C13—C14	1.517 (4)	C26—C27	1.516 (5)
C13—H13A	0.99	C26—H26A	0.99
C13—H13B	0.99	C26—H26B	0.99
C14—C15	1.519 (4)	C27—C28	1.516 (5)
C14—H14A	0.99	C27—H27A	0.99
C14—H14B	0.99	C27—H27B	0.99
C15—C16	1.522 (4)	C28—H28A	0.98
C15—H15A	0.99	C28—H28B	0.98
C15—H15B	0.99	C28—H28C	0.98

S2···S2ⁱ	3.2134 (18)

C2—C1—C6	119.2 (3)	C17—C16—H16B	108.9
C2—C1—S1	123.3 (2)	H16A—C16—H16B	107.7
C6—C1—S1	117.5 (2)	C16—C17—H17A	109.5
C3—C2—C1	120.5 (3)	C16—C17—H17B	109.5
C3—C2—H2	119.8	H17A—C17—H17B	109.5
C1—C2—H2	119.8	C16—C17—H17C	109.5
C2—C3—C4	120.1 (3)	H17A—C17—H17C	109.5
C2—C3—H3	120.0	H17B—C17—H17C	109.5
C4—C3—H3	120.0	C19—C18—S2	116.0 (2)
C5—C4—C3	120.3 (3)	C19—C18—H18A	108.3
C5—C4—H4	119.9	S2—C18—H18A	108.3
C3—C4—H4	119.9	C19—C18—H18B	108.3
C4—C5—C6	120.3 (3)	S2—C18—H18B	108.3
C4—C5—H5	119.9	H18A—C18—H18B	107.4
C6—C5—H5	119.9	C18—C19—C20	110.3 (3)
C5—C6—C1	119.6 (3)	C18—C19—H19A	109.6
C5—C6—S2	124.3 (2)	C20—C19—H19A	109.6
C1—C6—S2	116.0 (2)	C18—C19—H19B	109.6
C8—C7—S1	107.7 (2)	C20—C19—H19B	109.6
C8—C7—H7A	110.2	H19A—C19—H19B	108.1
S1—C7—H7A	110.2	C21—C20—C19	114.3 (3)
C8—C7—H7B	110.2	C21—C20—H20A	108.7
S1—C7—H7B	110.2	C19—C20—H20A	108.7
H7A—C7—H7B	108.5	C21—C20—H20B	108.7
C7—C8—C9	112.8 (3)	C19—C20—H20B	108.7
C7—C8—H8A	109.0	H20A—C20—H20B	107.6
C9—C8—H8A	109.0	C20—C21—C22	112.9 (3)
C7—C8—H8B	109.0	C20—C21—H21A	109.0
C9—C8—H8B	109.0	C22—C21—H21A	109.0
H8A—C8—H8B	107.8	C20—C21—H21B	109.0
C10—C9—C8	113.1 (3)	C22—C21—H21B	109.0
C10—C9—H9A	108.9	H21A—C21—H21B	107.8
C8—C9—H9A	108.9	C23—C22—C21	114.7 (3)
C10—C9—H9B	108.9	C23—C22—H22A	108.6
C8—C9—H9B	108.9	C21—C22—H22A	108.6
H9A—C9—H9B	107.8	C23—C22—H22B	108.6
C9—C10—C11	113.9 (3)	C21—C22—H22B	108.6
C9—C10—H10A	108.8	H22A—C22—H22B	107.6
C11—C10—H10A	108.8	C22—C23—C24	113.7 (3)
C9—C10—H10B	108.8	C22—C23—H23A	108.8
C11—C10—H10B	108.8	C24—C23—H23A	108.8
H10A—C10—H10B	107.7	C22—C23—H23B	108.8
C12—C11—C10	113.6 (3)	C24—C23—H23B	108.8
C12—C11—H11A	108.8	H23A—C23—H23B	107.7
C10—C11—H11A	108.8	C25—C24—C23	114.1 (3)
C12—C11—H11B	108.8	C25—C24—H24A	108.7
C10—C11—H11B	108.8	C23—C24—H24A	108.7
H11A—C11—H11B	107.7	C25—C24—H24B	108.7
C13—C12—C11	113.7 (3)	C23—C24—H24B	108.7
C13—C12—H12A	108.8	H24A—C24—H24B	107.6
C11—C12—H12A	108.8	C24—C25—C26	113.8 (3)
C13—C12—H12B	108.8	C24—C25—H25A	108.8
C11—C12—H12B	108.8	C26—C25—H25A	108.8
H12A—C12—H12B	107.7	C24—C25—H25B	108.8
C14—C13—C12	114.0 (3)	C26—C25—H25B	108.8
C14—C13—H13A	108.8	H25A—C25—H25B	107.7
C12—C13—H13A	108.8	C27—C26—C25	114.0 (3)
C14—C13—H13B	108.8	C27—C26—H26A	108.8
C12—C13—H13B	108.8	C25—C26—H26A	108.8
H13A—C13—H13B	107.7	C27—C26—H26B	108.8
C13—C14—C15	114.0 (3)	C25—C26—H26B	108.8
C13—C14—H14A	108.8	H26A—C26—H26B	107.6
C15—C14—H14A	108.8	C28—C27—C26	113.0 (3)
C13—C14—H14B	108.8	C28—C27—H27A	109.0
C15—C14—H14B	108.8	C26—C27—H27A	109.0
H14A—C14—H14B	107.7	C28—C27—H27B	109.0
C14—C15—C16	113.2 (3)	C26—C27—H27B	109.0
C14—C15—H15A	108.9	H27A—C27—H27B	107.8
C16—C15—H15A	108.9	C27—C28—H28A	109.5
C14—C15—H15B	108.9	C27—C28—H28B	109.5
C16—C15—H15B	108.9	H28A—C28—H28B	109.5
H15A—C15—H15B	107.8	C27—C28—H28C	109.5
C15—C16—C17	113.6 (3)	H28A—C28—H28C	109.5
C15—C16—H16A	108.9	H28B—C28—H28C	109.5
C17—C16—H16A	108.9	C1—S1—C7	104.66 (15)
C15—C16—H16B	108.9	C6—S2—C18	105.42 (15)

C6—C1—C2—C3	2.4 (5)	C13—C14—C15—C16	179.0 (3)
S1—C1—C2—C3	−177.1 (3)	C14—C15—C16—C17	178.6 (3)
C1—C2—C3—C4	−1.2 (5)	S2—C18—C19—C20	−176.2 (2)
C2—C3—C4—C5	−0.1 (5)	C18—C19—C20—C21	−179.2 (3)
C3—C4—C5—C6	0.1 (5)	C19—C20—C21—C22	−171.0 (3)
C4—C5—C6—C1	1.2 (5)	C20—C21—C22—C23	179.1 (3)
C4—C5—C6—S2	−179.9 (3)	C21—C22—C23—C24	−177.3 (3)
C2—C1—C6—C5	−2.4 (5)	C22—C23—C24—C25	179.8 (3)
S1—C1—C6—C5	177.1 (3)	C23—C24—C25—C26	177.6 (3)
C2—C1—C6—S2	178.6 (3)	C24—C25—C26—C27	−177.9 (3)
S1—C1—C6—S2	−1.9 (4)	C25—C26—C27—C28	173.9 (3)
S1—C7—C8—C9	−179.5 (2)	C2—C1—S1—C7	3.0 (3)
C7—C8—C9—C10	178.3 (3)	C6—C1—S1—C7	−176.4 (3)
C8—C9—C10—C11	−178.5 (3)	C8—C7—S1—C1	176.4 (2)
C9—C10—C11—C12	179.0 (3)	C5—C6—S2—C18	0.0 (3)
C10—C11—C12—C13	179.8 (3)	C1—C6—S2—C18	179.0 (3)
C11—C12—C13—C14	179.6 (3)	C19—C18—S2—C6	80.8 (3)
C12—C13—C14—C15	179.0 (3)

Symmetry code: (i) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···S1ⁱⁱ	0.99	2.99	3.749 (4)	134
C7—H7A···Cg1ⁱⁱⁱ	0.99	2.67	3.567 (16)	151

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

Experimental details

Crystal data
Chemical formula	C₂₈H₅₀S₂
M_r	450.80
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	5.4024 (10), 16.863 (3), 29.611 (5)
β (°)	91.245 (3)
V (Å³)	2696.9 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.55 × 0.11 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD-detector diffractometer
Absorption correction	Analytical (XPREP; Bruker 2000)
T_min, T_max	0.901, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	15683, 5958, 4452
R_int	0.086
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.088, 0.205, 1.14
No. of reflections	5958
No. of parameters	273
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.75, −0.55

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006), SHELXL97 (Sheldrick, 2008), KENX (Sakai, 2002), ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18B···S1ⁱ	0.99	2.99	3.749 (4)	134
C7—H7A···Cg1ⁱⁱ	0.99	2.67	3.567 (16)	151

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

References

Alves, H., Simão, D., Santos, I. C., Gama, V., Henriques, R. T., Novais, H. & Almeida, M. (2004). Eur. J. Inorg. Chem. 6, 1318-1329. Web of Science CSD CrossRef Google Scholar
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Volume 64| Part 6| June 2008| Page o1119

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