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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 1| January 2016| x152426
doi:10.1107/S2414314615024268

cis,trans,cis-1,2,3,4-Tetra­kis­[2-(ethyl­sulfan­yl)phen­yl]cyclo­butane

Barbara Sohr,a Florian Glöcklhofer,a Berthold Stöger,b Matthias Weilb* and Johannes Fröhlicha

aInstitute of Applied Synthetic Chemistry, TU Wien, Getreidemarkt 9/163, A-1060 Vienna, Austria, and bInstitute for Chemical Technologies and Analytics, Division of Structural Chemistry, TU Wien, Getreidemarkt 9/164-SC, A-1060 Vienna, Austria
*Correspondence e-mail: matthias.weil@tuwien.ac.at

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 October 2015; accepted 17 December 2015; online 12 January 2016)

The title cyclo­butane derivative, C36H40S4, formed serendipitously through a photochemically initiated [2 + 2] cyclo­addition. The asymmetric unit contains half a mol­ecule with the 2-(ethyl­sulfan­yl)phenyl substituents in a cis configuration, the other half of the mol­ecule being generated by the application of a twofold rotation operation. The substituents in both halves of the mol­ecules are in a trans arrangement relative to each other. The cyclo­butane ring shows angular and torsional strains, with C—C—C bond angles of 89.80 (8) and 88.40 (8)°, and an average absolute torsion angle of 14.28 (10)°. The angle of pucker in the ring is 20.27 (12)°. The Ccb—Ccb—Cb angles between the cyclo­butane (cb) ring atoms and the attached benzene (b) ring atoms are widened and range from 115.19 (10) to 121.66 (10)°. A weak intra­molecular C—H⋯S hydrogen-bonding inter­action between one of the cyclo­butane ring H atoms and the S atom may help to establish the mol­ecular conformation. No specific inter­molecular inter­actions are found.

CCDC reference: 1443096

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

The title compound was obtained from a bis-thio­ethyl-substituted stilbene by an unintentional [2 + 2] cyclo­addition (Figs. 1[link] and 2[link]). A weak intra­molecular C—H⋯S hydrogen-bonding inter­action between one of the cyclo­butane ring H atoms and the S atom may help to establish the mol­ecular conformation ((Fig. 3[link] and Table 1[link]). The stilbene was synthesized as a model compound for thio­alkyl-substituted poly(p-phenyl­ene vinyl­ene) (PPV). PPVs were among the first materials applied in organic solar cells as well as organic LEDs and have become one of the materials of choice for studies on the basic photophysics of conjugated polymers (Blayney et al., 2014[Blayney, A. J., Perepichka, I. F., Wudl, F. & Perepichka, D. F. (2014). Isr. J. Chem. 54, 674-688.]). For synthetic details, see: Diéguez et al. (2010[Diéguez, H. R., López, A., Domingo, V., Arteaga, J. F., Dobado, J. A., Herrador, M. M., Quílez del Moral, J. F. & Barrero, A. F. (2010). J. Am. Chem. Soc. 132, 254-259.]); Tzur et al. (2010[Tzur, E., Szadkowska, A., Ben-Asuly, A., Makal, A., Goldberg, I., Woźniak, K., Grela, K. & Lemcoff, N. G. (2010). Chem. Eur. J. 16, 8726-8737.]). For a review on conformations and configurations of cyclo­butanes, see: Berg (2005[Berg, U. (2005). The chemistry of cyclobutanes, edited by Z. Rappoport & J. F. Liebman, pp. 83-132. Chichester: John Wiley & Sons.]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C2—H1c2⋯S2 0.96 2.47 3.1939 (12) 132
[Figure 1]
Figure 1
Reaction scheme to obtain the title compound (top) and the originally intended product (bottom).
[Figure 2]
Figure 2
The mol­ecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level; H atoms are given as spheres of arbitrary radius. Non-labelled atoms are generated by symmetry code −x + 2, y, −z + [{1\over 2}].
[Figure 3]
Figure 3
The packing of the mol­ecules in the crystal structure of the title compound in a view along [100].

Synthesis and crystallization

The reaction pathway involving compounds 1–3 and the originally intended reaction product 4 are schematically shown (Fig. 1[link]). The synthesis of stilbene 2 was carried out following a McMurry reaction protocol of Diéguez et al. (2010[Diéguez, H. R., López, A., Domingo, V., Arteaga, J. F., Dobado, J. A., Herrador, M. M., Quílez del Moral, J. F. & Barrero, A. F. (2010). J. Am. Chem. Soc. 132, 254-259.]). Zinc (2.94 g, 45 mmol) and titanocene dichloride (5.60 g, 22.5 mmol) were dissolved in 40 ml dry, degassed tetra­hydro­furan under argon atmosphere. The solution was stirred for 5 min and aldehyde 1 (2.49 g, 15 mmol), which was prepared by a modified procedure of Tzur et al. (2010[Tzur, E., Szadkowska, A., Ben-Asuly, A., Makal, A., Goldberg, I., Woźniak, K., Grela, K. & Lemcoff, N. G. (2010). Chem. Eur. J. 16, 8726-8737.]), was added to the reaction mixture as a solution in 30 ml dry, degassed tetra­hydro­furan. The reaction was heated to reflux for 3 h, cooled to room temperature and quenched with 30 ml diisopropyl ether. The solvent was evaporated in vacuo, the residue was dissolved in di­chloro­methane and washed with 1M HCl and brine. The organic layer was then dried over anhydrous sodium sulfate and the solvent was again evaporated in vacuo. The resulting dark-orange oil was purified by column chromatography using silica gel as stationary phase and a petroleum ether:di­chloro­methane mixture (5:1 to 3:1 v/v) as eluent. A second column using aluminum oxide yielded 2 as a colorless oil (0.88 g, 2.9 mmol, 39%). Storage of 2 at room temperature and without light protection resulted in the quanti­tative formation of crystals of the title compound 3 in the form of translucent blocks within two weeks. 1H NMR (CDCl3, 200 MHz): δ = 7.41–7.32 (m, 4H), 7.21– 7.13 (m, 4H), 7.09–6.98 (m, 8H), 5.01 (s, 4H), 2.87–2.59 (m, 8H), 1.16 (t, 12H, J = 7.5 Hz) p.p.m. 13C NMR (APT) (CDCl3, 50 MHz): δ = 140.1 (s), 136.9 (s), 128.9 (d), 127.6 (d), 126.4 (d), 125.3 (d), 44.8 (d), 28.3 (t), 14.2 (q) p.p.m.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C36H40S4
Mr 600.92
Crystal system, space group Monoclinic, C2/c
Temperature (K) 100
a, b, c (Å) 11.2972 (8), 13.0708 (10), 21.3833 (17)
β (°) 98.400 (2)
V (Å3) 3123.7 (4)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.33
Crystal size (mm) 0.65 × 0.62 × 0.48
 
Data collection
Diffractometer Bruker APEXII CCD diffractometer
Absorption correction Multi-scan (SADABS; Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.80, 0.88
No. of measured, independent and observed [I > 3σ(I)] reflections 31669, 5518, 4606
Rint 0.023
(sin θ/λ)max (Å−1) 0.758
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.058, 3.21
No. of reflections 5518
No. of parameters 181
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.57, −0.51
Computer programs: APEX2 (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SUPERFLIP (Palatinus & Chapuis, 2007[Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790.]), JANA2006 (Petříček et al., 2014[Petříček, V., Dušek, M. & Palatinus, L. (2014). Z. Kristallogr. 229, 345-352.]), XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]), publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Structural data

CCDC reference: 1443096

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314615024268/hb4001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314615024268/hb4001Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314615024268/hb4001Isup3.cml

checkCIF report


Synthesis and Crystallization top

The reaction pathway involving compounds 1 - 3 and the originally intended reaction product 4 are schematically shown (Fig. 1). The synthesis of stilbene 2 was carried out following a McMurry reaction protocol of Diéguez et al. (2010). Zinc (2.94 g, 45 mmol) and titanocene dichloride (5.60 g, 22.5 mmol) were dissolved in 40 ml dry, degassed tetra­hydro­furan under argon atmosphere. The solution was stirred for 5 min and aldehyde 1 (2.49 g, 15 mmol), which was prepared by a modified procedure of Tzur et al. (2010), was added to the reaction mixture as a solution in 30 ml dry, degassed tetra­hydro­furan. The reaction was heated to reflux for 3 h, cooled to room temperature and quenched with 30 ml diiso­propyl ether. The solvent was evaporated in vacuo, the residue was dissolved in di­chloro­methane and washed with 1 N HCl and brine. The organic layer was then dried over anhydrous sodium sulfate and the solvent was again evaporated in vacuo. The resulting dark orange oil was purified by column chromatography using silica gel as stationary phase and a petrol ether:di­chloro­methane mixture (5:1 to 3:1 v/v) as eluent. A second column using aluminium oxide yielded 2 as a colorless oil (0.88 g, 2.9 mmol, 39%). Storage of 2 at room temperature and without light protection resulted in the qu­anti­tative formation of crystals of the title compound 3 in the form of translucent blocks within two weeks. 1H NMR (CDCl3, 200 MHz): δ = 7.41 − 7.32 (m, 4H), 7.21 − 7.13 (m, 4H), 7.09 − 6.98 (m, 8H), 5.01 (s, 4H), 2.87 − 2.59 (m, 8H), 1.16 (t, 12H, J = 7.5 Hz) p.p.m. 13C NMR (APT) (CDCl3, 50 MHz): δ = 140.1 (s), 136.9 (s), 128.9 (d), 127.6 (d), 126.4 (d), 125.3 (d), 44.8 (d), 28.3 (t), 14.2 (q) p.p.m.

Refinement top

H atoms were placed in calculated positions and were refined in the riding atom approximation, with Uiso(H) = 1.2Ueq(C).

Related literature top

The title compound was obtained from a bis-thioethyl substituted stilbene by an unintentional [2 + 2] cycloaddition. The stilbene was synthesized as a model compound for thioalkyl-substituted poly(p-phenylene vinylene) (PPV). PPVs were among the first materials applied in organic solar cells as well as organic LEDs and have become one of the materials of choice for studies on the basic photophysics of conjugated polymers (Blayney et al., 2014). For synthetic details, see: Diéguez et al. (2010); Tzur et al. (2010). For a review on conformations and configurations of cyclobutanes, see: Berg (2005).

Experimental top

The reaction pathway involving compounds 1–3 and the originally intended reaction product 4 are schematically shown (Fig. 1). The synthesis of stilbene 2 was carried out following a McMurry reaction protocol of Diéguez et al. (2010). Zinc (2.94 g, 45 mmol) and titanocene dichloride (5.60 g, 22.5 mmol) were dissolved in 40 ml dry, degassed tetrahydrofuran under argon atmosphere. The solution was stirred for 5 min and aldehyde 1 (2.49 g, 15 mmol), which was prepared by a modified procedure of Tzur et al. (2010), was added to the reaction mixture as a solution in 30 ml dry, degassed tetrahydrofuran. The reaction was heated to reflux for 3 h, cooled to room temperature and quenched with 30 ml diisopropyl ether. The solvent was evaporated in vacuo, the residue was dissolved in dichloromethane and washed with 1N HCl and brine. The organic layer was then dried over anhydrous sodium sulfate and the solvent was again evaporated in vacuo. The resulting dark-orange oil was purified by column chromatography using silica gel as stationary phase and a petrol ether:dichloromethane mixture (5:1 to 3:1 v/v) as eluent. A second column using aluminium oxide yielded 2 as a colorless oil (0.88 g, 2.9 mmol, 39%). Storage of 2 at room temperature and without light protection resulted in the quantitative formation of crystals of the title compound 3 in the form of translucent blocks within two weeks. 1H NMR (CDCl3, 200 MHz): δ = 7.41–7.32 (m, 4H), 7.21– 7.13 (m, 4H), 7.09–6.98 (m, 8H), 5.01 (s, 4H), 2.87–2.59 (m, 8H), 1.16 (t, 12H, J = 7.5 Hz) p.p.m. 13C NMR (APT) (CDCl3, 50 MHz): δ = 140.1 (s), 136.9 (s), 128.9 (d), 127.6 (d), 126.4 (d), 125.3 (d), 44.8 (d), 28.3 (t), 14.2 (q) p.p.m.

Refinement top

H atoms were placed in calculated positions and were refined in the riding atom approximation, with Uiso(H) = 1.2Ueq(C).

Structure description top

The title compound was obtained from a bis-thioethyl substituted stilbene by an unintentional [2 + 2] cycloaddition. The stilbene was synthesized as a model compound for thioalkyl-substituted poly(p-phenylene vinylene) (PPV). PPVs were among the first materials applied in organic solar cells as well as organic LEDs and have become one of the materials of choice for studies on the basic photophysics of conjugated polymers (Blayney et al., 2014). For synthetic details, see: Diéguez et al. (2010); Tzur et al. (2010). For a review on conformations and configurations of cyclobutanes, see: Berg (2005).

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007); program(s) used to refine structure: JANA2006 (Petříček et al., 2014); molecular graphics: XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Reaction scheme to obtain the title compound (top) and the originally intended product (bottom).
[Figure 2] Fig. 2. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level; H atoms are given as spheres of arbitrary radius. Non-labelled atoms are generated by symmetry code −x + 2, y, −z + 1/2.
[Figure 3] Fig. 3. The packing of the molecules in the crystal structure of the title compound in a view along [100].
cis,trans,cis-1,2,3,4-Tetrakis[2-(ethylsulfanyl)phenyl]cyclobutane top
Crystal data top
C36H40S4F(000) = 1280
Mr = 600.92Dx = 1.278 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9001 reflections
a = 11.2972 (8) Åθ = 2.9–32.6°
b = 13.0708 (10) ŵ = 0.33 mm−1
c = 21.3833 (17) ÅT = 100 K
β = 98.400 (2)°Block, translucent colourless
V = 3123.7 (4) Å30.65 × 0.62 × 0.48 mm
Z = 4
Data collection top
Bruker APEXII CCD
diffractometer		5518 independent reflections
Radiation source: X-ray tube4606 reflections with I > 3σ(I)
Graphite monochromatorRint = 0.023
ω and φ–scansθmax = 32.6°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		h = −17→17
Tmin = 0.80, Tmax = 0.88k = −19→19
31669 measured reflectionsl = −32→32
Refinement top
Refinement on F80 constraints
R[F2 > 2σ(F2)] = 0.041H-atom parameters constrained
wR(F2) = 0.058Weighting scheme based on measured s.u.'s w = 1/(σ2(F) + 0.0001F2)
S = 3.21(Δ/σ)max = 0.019
5518 reflectionsΔρmax = 0.57 e Å−3
181 parametersΔρmin = −0.51 e Å−3
0 restraints
Crystal data top
C36H40S4V = 3123.7 (4) Å3
Mr = 600.92Z = 4
Monoclinic, C2/cMo Kα radiation
a = 11.2972 (8) ŵ = 0.33 mm−1
b = 13.0708 (10) ÅT = 100 K
c = 21.3833 (17) Å0.65 × 0.62 × 0.48 mm
β = 98.400 (2)°
Data collection top
Bruker APEXII CCD
diffractometer		5518 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2014)		4606 reflections with I > 3σ(I)
Tmin = 0.80, Tmax = 0.88Rint = 0.023
31669 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0410 restraints
wR(F2) = 0.058H-atom parameters constrained
S = 3.21Δρmax = 0.57 e Å−3
5518 reflectionsΔρmin = −0.51 e Å−3
181 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.87910 (3)0.00251 (3)0.077753 (15)0.01809 (10)
S20.95635 (3)−0.26468 (3)0.105586 (15)0.01571 (9)
C10.97736 (10)0.02697 (9)0.21431 (5)0.0109 (3)
C20.99420 (11)−0.09281 (9)0.21282 (5)0.0111 (3)
C31.03225 (11)0.09664 (9)0.17023 (6)0.0122 (3)
C40.99249 (11)0.09175 (9)0.10458 (6)0.0135 (3)
C51.04055 (12)0.15814 (10)0.06346 (6)0.0183 (4)
C61.12381 (12)0.23133 (11)0.08726 (7)0.0204 (4)
C71.16082 (12)0.23866 (10)0.15155 (7)0.0196 (4)
C81.11571 (11)0.17117 (10)0.19249 (6)0.0155 (3)
C91.10217 (10)−0.13204 (9)0.18639 (6)0.0118 (3)
C101.09395 (11)−0.20633 (10)0.13841 (6)0.0133 (3)
C111.19725 (13)−0.23932 (10)0.11493 (6)0.0176 (4)
C121.30895 (12)−0.20113 (10)0.13908 (7)0.0193 (4)
C131.31825 (12)−0.12954 (10)0.18711 (7)0.0187 (4)
C141.21622 (11)−0.09526 (10)0.20995 (6)0.0158 (4)
C150.81195 (12)0.05410 (11)0.00215 (6)0.0201 (4)
C160.69192 (16)0.00156 (14)−0.01675 (8)0.0362 (5)
C170.95165 (12)−0.36869 (10)0.16180 (6)0.0197 (4)
C181.05717 (13)−0.44112 (11)0.16675 (9)0.0311 (5)
H1c10.9012130.0565160.1981490.013*
H1c20.936693−0.1347840.1870750.0133*
H1c51.0157580.152930.0186860.0219*
H1c61.1559040.2771570.0589210.0244*
H1c71.2175410.2901860.1679560.0235*
H1c81.1427790.1761510.2370760.0186*
H1c111.19035−0.2891350.08160.0212*
H1c121.379047−0.2240930.1226690.0231*
H1c131.395355−0.103420.2047470.0224*
H1c141.224302−0.044790.2429170.0189*
H1c150.7997020.126340.0061580.0241*
H2c150.8630110.040274−0.0290040.0241*
H1c160.6571920.024312−0.0580670.0435*
H2c160.703434−0.071188−0.017310.0435*
H3c160.639380.0183870.0131870.0435*
H1c170.945536−0.3409330.2027670.0237*
H2c170.878734−0.4065820.1510010.0237*
H1c181.045087−0.4965260.1946070.0374*
H2c181.0643−0.4677610.1256280.0374*
H3c181.129027−0.405020.1831550.0374*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.02583 (19)0.01681 (17)0.01032 (15)−0.00304 (13)−0.00175 (12)0.00162 (11)
S20.01991 (17)0.01504 (16)0.01128 (14)−0.00217 (12)−0.00074 (12)−0.00097 (11)
C10.0103 (5)0.0125 (5)0.0098 (5)0.0012 (5)0.0014 (4)0.0000 (4)
C20.0115 (5)0.0123 (6)0.0092 (5)−0.0010 (4)0.0004 (4)−0.0008 (4)
C30.0122 (5)0.0129 (6)0.0120 (5)0.0029 (5)0.0038 (4)0.0003 (4)
C40.0166 (6)0.0134 (6)0.0110 (5)0.0024 (5)0.0035 (4)−0.0001 (4)
C50.0250 (7)0.0187 (6)0.0125 (6)0.0033 (5)0.0074 (5)0.0022 (5)
C60.0224 (7)0.0193 (7)0.0214 (6)0.0003 (6)0.0101 (5)0.0056 (5)
C70.0187 (6)0.0175 (7)0.0231 (7)−0.0042 (5)0.0049 (5)0.0023 (5)
C80.0156 (6)0.0162 (6)0.0146 (6)0.0003 (5)0.0022 (5)0.0008 (5)
C90.0130 (6)0.0111 (6)0.0117 (5)0.0005 (5)0.0027 (4)0.0015 (4)
C100.0175 (6)0.0122 (6)0.0106 (5)−0.0006 (5)0.0030 (4)0.0013 (4)
C110.0235 (7)0.0146 (6)0.0163 (6)0.0021 (5)0.0082 (5)0.0002 (5)
C120.0178 (6)0.0177 (6)0.0245 (7)0.0048 (5)0.0105 (5)0.0043 (5)
C130.0120 (6)0.0175 (6)0.0271 (7)0.0003 (5)0.0050 (5)0.0022 (5)
C140.0145 (6)0.0147 (6)0.0180 (6)−0.0001 (5)0.0024 (5)−0.0022 (5)
C150.0290 (7)0.0199 (7)0.0106 (5)0.0004 (6)0.0001 (5)0.0012 (5)
C160.0430 (10)0.0410 (10)0.0196 (7)−0.0122 (8)−0.0125 (7)0.0072 (7)
C170.0197 (7)0.0189 (7)0.0198 (6)−0.0047 (5)0.0004 (5)0.0044 (5)
C180.0253 (8)0.0228 (8)0.0443 (10)−0.0013 (7)0.0018 (7)0.0133 (7)
Geometric parameters (Å, º) top
S1—C41.7652 (13)C11—C121.3849 (19)
S2—C101.7810 (13)C11—H1c110.96
C1—C1i1.5373 (16)C12—C131.382 (2)
C1—C31.5076 (18)C12—H1c120.96
C1—H1c10.96C13—C141.3901 (19)
C2—C91.5072 (18)C13—H1c130.96
C2—H1c20.96C14—H1c140.96
C3—C41.4115 (17)C15—C161.521 (2)
C3—C81.3905 (17)C15—H1c150.96
C4—C51.4000 (19)C15—H2c150.96
C5—C61.3852 (19)C16—H1c160.96
C5—H1c50.96C16—H2c160.96
C6—C71.381 (2)C16—H3c160.96
C6—H1c60.96C17—C181.514 (2)
C7—C81.391 (2)C17—H1c170.96
C7—H1c70.96C17—H2c170.96
C8—H1c80.96C18—H1c180.96
C9—C101.4057 (17)C18—H2c180.96
C9—C141.3983 (17)C18—H3c180.96
C10—C111.404 (2)
C1i—C1—C3120.87 (10)C10—C11—H1c11119.48
C1i—C1—H1c1120.54C12—C11—H1c11119.48
C3—C1—H1c187.75C11—C12—C13119.17 (13)
C9—C2—H1c296.17C11—C12—H1c12120.41
C1—C3—C4119.63 (10)C13—C12—H1c12120.41
C1—C3—C8121.97 (11)C12—C13—C14120.16 (12)
C4—C3—C8118.26 (11)C12—C13—H1c13119.92
S1—C4—C3117.61 (9)C14—C13—H1c13119.92
S1—C4—C5122.35 (9)C9—C14—C13122.02 (12)
C3—C4—C5120.01 (11)C9—C14—H1c14118.99
C4—C5—C6120.15 (12)C13—C14—H1c14118.99
C4—C5—H1c5119.93C16—C15—H1c15109.47
C6—C5—H1c5119.93C16—C15—H2c15109.47
C5—C6—C7120.28 (13)H1c15—C15—H2c15110.86
C5—C6—H1c6119.86C15—C16—H1c16109.47
C7—C6—H1c6119.86C15—C16—H2c16109.47
C6—C7—C8119.82 (12)C15—C16—H3c16109.47
C6—C7—H1c7120.09H1c16—C16—H2c16109.47
C8—C7—H1c7120.09H1c16—C16—H3c16109.47
C3—C8—C7121.43 (12)H2c16—C16—H3c16109.47
C3—C8—H1c8119.29C18—C17—H1c17109.47
C7—C8—H1c8119.29C18—C17—H2c17109.47
C2—C9—C10122.54 (10)H1c17—C17—H2c17103.93
C2—C9—C14120.10 (11)C17—C18—H1c18109.47
C10—C9—C14117.37 (11)C17—C18—H2c18109.47
S2—C10—C9122.98 (10)C17—C18—H3c18109.47
S2—C10—C11116.79 (9)H1c18—C18—H2c18109.47
C9—C10—C11120.22 (11)H1c18—C18—H3c18109.47
C10—C11—C12121.03 (12)H2c18—C18—H3c18109.47
Symmetry code: (i) −x+2, y, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H1c2···S20.962.473.1939 (12)132
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H1c2···S20.962.473.1939 (12)132

Experimental details

Crystal data
Chemical formulaC36H40S4
Mr600.92
Crystal system, space groupMonoclinic, C2/c
Temperature (K)100
a, b, c (Å)11.2972 (8), 13.0708 (10), 21.3833 (17)
β (°) 98.400 (2)
V (Å3)3123.7 (4)
Z4
Radiation typeMo Kα
µ (mm−1)0.33
Crystal size (mm)0.65 × 0.62 × 0.48
Data collection
DiffractometerBruker APEXII CCD
Absorption correctionMulti-scan
(SADABS; Bruker, 2014)
Tmin, Tmax0.80, 0.88
No. of measured, independent and
observed [I > 3σ(I)] reflections		31669, 5518, 4606
Rint0.023
(sin θ/λ)max (Å−1)0.758
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.041, 0.058, 3.21
No. of reflections5518
No. of parameters181
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.57, −0.51

Computer programs: APEX2 (Bruker, 2014), SAINT (Bruker, 2014), SUPERFLIP (Palatinus & Chapuis, 2007), JANA2006 (Petříček et al., 2014), XP in SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006), publCIF (Westrip, 2010).

 

Acknowledgements

The X-ray centre of TU Wien is acknowledged for providing access to the single-crystal diffractometer.

References

First citationBerg, U. (2005). The chemistry of cyclobutanes, edited by Z. Rappoport & J. F. Liebman, pp. 83–132. Chichester: John Wiley & Sons.  Google Scholar
 First citationBlayney, A. J., Perepichka, I. F., Wudl, F. & Perepichka, D. F. (2014). Isr. J. Chem. 54, 674–688.  Web of Science CrossRef CAS Google Scholar
 First citationBruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationDiéguez, H. R., López, A., Domingo, V., Arteaga, J. F., Dobado, J. A., Herrador, M. M., Quílez del Moral, J. F. & Barrero, A. F. (2010). J. Am. Chem. Soc. 132, 254–259.  Web of Science PubMed Google Scholar
 First citationMacrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
 First citationPalatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786–790.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationPetříček, V., Dušek, M. & Palatinus, L. (2014). Z. Kristallogr. 229, 345–352.  Google Scholar
 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationTzur, E., Szadkowska, A., Ben-Asuly, A., Makal, A., Goldberg, I., Woźniak, K., Grela, K. & Lemcoff, N. G. (2010). Chem. Eur. J. 16, 8726–8737.  Web of Science CSD CrossRef CAS PubMed Google Scholar
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 1| January 2016| x152426
doi:10.1107/S2414314615024268
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