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

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ISSN: 2056-9890

1-Methyl-4-({5-[(4-methyl­phen­yl)sulfan­yl]pent­yl}sulfan­yl)benzene

aDepartamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, bDepartamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Casilla 170, Antofagasta, Chile, cInstitut für Anorganische Chemie der Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, D-60438 Frankfurt am Main, Germany, and dInstituto de Bio-Orgánica 'Antonio González', Universidad de La Laguna, Astrofísico Francisco, Sánchez N°2, La Laguna, Tenerife, Spain
*Correspondence e-mail: ivanbritob@yahoo.com

(Received 20 October 2009; accepted 27 October 2009; online 4 November 2009)

There are two independent mol­ecules in the asymmetric unit of the title compound, C19H24S2. In both mol­ecules, the aliphatic segment of the ligand is in an all-trans conformation: the –S–(CH2)5–S–bridging chain is almost planar (r.m.s. deviation for all non-H atoms = 0.0393 and 0.0796 Å in the two mol­ecules) and maximally extended. Their mean planes form dihedral angles of 4.08 (6)/20.47 (6) and 2.22 (6)/58.19 (6)° with the aromatic rings in the two mol­ecules. The crystal packing is purely governed by weak inter­molecular forces.

Related literature

For the potential of coordination polymers based on multitopic bridging ligands and metal centers as functional mat­erials, see: Guo et al. (2002[Guo, D., Pang, K. L., Duan, C. Y., He, C. & Meng, Q. (2002). Inorg. Chem. 41, 5978-5985.]); Melcer et al. (2001[Melcer, N. J., Enright, G. D., Ripmeester, J. A. & Shimizu, G. K. H. (2001). Inorg. Chem. 40, 4641-4648.]). For the use of flexible ligands in such structures, see: Bu et al. (2001[Bu, X. H., Chen, W., Lu, S. L., Zhang, R. H., Liao, D. Z., Bu, W. M., Shionoya, M., Brisse, F. & Ribas, J. (2001). Angew. Chem. Int. Ed. 40, 3201-3203.]); Withersby et al. (1997[Withersby, M. A., Blake, A. J., Champness, N. R., Hubberstey, P., Li, W. S. & Schröder, M. (1997). Angew. Chem. Int. Ed. Engl. 36, 2327-2329.]). For our studies on the synthesis and structural characterization of S(II) compounds, see: Brito et al. (2004[Brito, I., Vargas, D., León, Y., Cárdenas, A., López-Rodríguez, M. & Wittke, O. (2004). Acta Cryst. E60, o1668-o1670.], 2005[Brito, I., Vargas, D., Reyes, A., Cárdenas, A. & López-Rodríguez, M. (2005). Acta Cryst. C61, o234-o236.], 2006[Brito, I., López-Rodríguez, M., Vargas, D. & León, Y. (2006). Acta Cryst. E62, o914-o916.]). For comparison bond distances in several phenylthioether compounds, see: Murray & Hartley (1981[Murray, S. G. & Hartley, F. R. (1981). Chem. Rev. 81, 365-414.]).

[Scheme 1]

Experimental

Crystal data
  • C19H24S2

  • Mr = 316.5

  • Triclinic, [P \overline 1]

  • a = 5.7350 (3) Å

  • b = 14.8989 (7) Å

  • c = 20.5873 (9) Å

  • α = 84.586 (4)°

  • β = 88.355 (4)°

  • γ = 83.937 (4)°

  • V = 1741.13 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 173 K

  • 0.37 × 0.32 × 0.3 mm

Data collection
  • Stoe IPDS II two-circle diffractometer

  • Absorption correction: multi-scan (MULABS; Spek, 2003[Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.]; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.898, Tmax = 0.916

  • 31941 measured reflections

  • 7762 independent reflections

  • 6312 reflections with I > 2σ(I)

  • Rint = 0.046

Refinement
  • R[F2 > 2σ(F2)] = 0.035

  • wR(F2) = 0.095

  • S = 1.00

  • 7762 reflections

  • 383 parameters

  • H-atom parameters constrained

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.40 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001[Stoe & Cie (2001). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.]); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: XP (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).

Supporting information


Comment top

In recent years, the rational design of coordination polymers based on multitopic bridging ligands and metal centers represents one of the most rapidly developing fields owing to their potential as functional materials (Guo et al., 2002; Melcer et al., 2001). The use of flexible ligands in such studies has attracted increasing attention because the flexibility and conformational freedom of such ligands offer the possibility for the construction of diverse frameworks with tailored properties and functions (Bu et al., 2001; Withersby et al., 1997).

The structure of the title compound is described here as part of our work involving the study of the synthesis and structural characterization of divalent-sulfur compounds (Brito et al., 2004, 2005, 2006). In both molecules the aliphatic segment of this ligand is in an all-trans conformation. The bridging chain moiety, –S-(CH2)5-S–, is almost planar (r.m.s. deviation for all non-H atoms: 0.0393 and 0.0796 Å). Its mean planes form a dihedral angle of 4.08 (6) and 20.47 (6)°; 2.22 (6) and 58.19 (6)° with the aromatic rings in the molecules A and B, respectively. The conformation of the central –S-(CH2)5-S– fragment is maximally extended. The average S-Csp2 bond distance of 1.7717 (12) Å is considerably shorter than the average S-Csp3 distance of 1.8151 (12) Å; corresponding bond distances in several phenylthioether compounds (Murray & Hartley, 1981) are 1.75 and 1.81Å respectively. The bond angles at sulfur [average 103.8 (6)°] are less than tetrahedral as is usually found in simple sulfides.

Related literature top

For the potential of coordination polymers based on multitopic bridging ligands and metal centers as functional materials, see: Guo et al. (2002); Melcer et al. (2001). For the use of flexible ligands in such structures, see: Bu et al. (2001); Withersby et al. (1997). For our studies on the synthesis and structural characterization of divalent sulfur compounds, see: Brito et al. (2004, 2005, 2006). For comparation of atomic and molecular parameters, see: Murray & Hartley (1981).

Experimental top

The title compound was synthesized as follows: A solution of 1,5-dibromopentane (1.15 g, 5 mmol) in ethanol (10 ml) was added dropwise to a mixture of p-thiocresol (1.36 g, 11 mmol), KOH (0.615 g, 11 mmol) and ethanol (10 ml). The reaction mixture was stirred for 24 h at room temperature. The precipitate was filtered off and washed with water. Yield 74%; m.p. 317 K. FT—IR (KBr pellets, cm-1): ν (s, C—H of CH3 (asym)) 2980, ν (w, C—H of CH3(sym)) 2847, ν (w, C—H (aliphatic chain, sym) 2944, ν (w, C—H (chain aliphatic, asym) 2924, ν (s, C—H disubstitution 1,2) 1424,, ν (w, C—S) 731. Crystals suitable for single-crystals X-ray analysis were obtained by recrystallization from an acetonitrile solution.

Refinement top

Hydrogen atoms were located in a difference Fourier map but they were included in calculated positions [C—H = 0.95 - 0.99 Å] and refined as riding [Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl)]. The methyl groups in one molecule were refined as being disordered over two equally populated sites. All methyl groups were allowed to rotate but not to tip.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Sheldrick, 2008); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. A view of the two independent molecules of the title compound, with the atom-numbering scheme (A bottom and B top). Displacement ellipsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
1-Methyl-4-({5-[(4-methylphenyl)sulfanyl]pentyl}sulfanyl)benzene top
Crystal data top
C19H24S2Z = 4
Mr = 316.5F(000) = 680
Triclinic, P1Dx = 1.207 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.7350 (3) ÅCell parameters from 28731 reflections
b = 14.8989 (7) Åθ = 2.4–27.6°
c = 20.5873 (9) ŵ = 0.30 mm1
α = 84.586 (4)°T = 173 K
β = 88.355 (4)°Block, colourless
γ = 83.937 (4)°0.37 × 0.32 × 0.3 mm
V = 1741.13 (14) Å3
Data collection top
Stoe IPDS II two-circle
diffractometer
6312 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.046
ω scansθmax = 27.2°, θmin = 2.3°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 77
Tmin = 0.898, Tmax = 0.916k = 1919
31941 measured reflectionsl = 2626
7762 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0641P)2]
where P = (Fo2 + 2Fc2)/3
7762 reflections(Δ/σ)max = 0.001
383 parametersΔρmax = 0.17 e Å3
0 restraintsΔρmin = 0.40 e Å3
Crystal data top
C19H24S2γ = 83.937 (4)°
Mr = 316.5V = 1741.13 (14) Å3
Triclinic, P1Z = 4
a = 5.7350 (3) ÅMo Kα radiation
b = 14.8989 (7) ŵ = 0.30 mm1
c = 20.5873 (9) ÅT = 173 K
α = 84.586 (4)°0.37 × 0.32 × 0.3 mm
β = 88.355 (4)°
Data collection top
Stoe IPDS II two-circle
diffractometer
7762 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
6312 reflections with I > 2σ(I)
Tmin = 0.898, Tmax = 0.916Rint = 0.046
31941 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0350 restraints
wR(F2) = 0.095H-atom parameters constrained
S = 1.00Δρmax = 0.17 e Å3
7762 reflectionsΔρmin = 0.40 e Å3
383 parameters
Special details top

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.

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
xyzUiso*/UeqOcc. (<1)
S10.47078 (5)0.34976 (2)0.553712 (14)0.03300 (8)
S20.28810 (6)0.27344 (2)0.186815 (15)0.04058 (9)
C10.6130 (2)0.37163 (8)0.47493 (5)0.0295 (2)
H1A0.60770.43770.46260.035*
H1B0.77910.34550.47610.035*
C20.4783 (2)0.32682 (8)0.42613 (5)0.0308 (2)
H2A0.49630.26040.43750.037*
H2B0.30940.34820.42990.037*
C30.5604 (2)0.34685 (8)0.35559 (6)0.0311 (2)
H3A0.72810.32420.35110.037*
H3B0.54440.41320.3440.037*
C40.4164 (2)0.30178 (8)0.30902 (6)0.0321 (2)
H4A0.44010.23520.31930.039*
H4B0.24790.32150.31590.039*
C50.4831 (2)0.32489 (9)0.23764 (6)0.0348 (3)
H5A0.6480.30130.22930.042*
H5B0.46740.39150.22720.042*
C110.64268 (19)0.39437 (7)0.61017 (5)0.0271 (2)
C120.8360 (2)0.44212 (8)0.59405 (6)0.0310 (2)
H120.88350.45290.54970.037*
C130.9589 (2)0.47391 (8)0.64276 (6)0.0325 (2)
H131.09020.50630.6310.039*
C140.8954 (2)0.45972 (8)0.70837 (6)0.0305 (2)
C150.7008 (2)0.41199 (8)0.72387 (6)0.0324 (2)
H150.65310.40150.76830.039*
C160.5764 (2)0.37974 (8)0.67601 (6)0.0317 (2)
H160.44510.34740.68790.038*
C171.0314 (2)0.49382 (9)0.76097 (6)0.0399 (3)
H17A1.19820.48990.74860.06*0.5
H17B1.01070.45670.80220.06*0.5
H17C0.97370.55710.76630.06*0.5
H17D0.92350.51250.79610.06*0.5
H17E1.11110.54570.74250.06*0.5
H17F1.1480.44540.77840.06*0.5
C210.3592 (2)0.32102 (8)0.10740 (6)0.0319 (2)
C220.5809 (2)0.30352 (9)0.07944 (6)0.0393 (3)
H220.70160.2690.10440.047*
C230.6276 (2)0.33592 (9)0.01566 (6)0.0412 (3)
H230.78060.32360.00240.049*
C240.4553 (2)0.38607 (8)0.02229 (6)0.0374 (3)
C250.2359 (2)0.40369 (9)0.00603 (6)0.0435 (3)
H250.1150.43780.01910.052*
C260.1878 (2)0.37279 (9)0.07023 (6)0.0404 (3)
H260.03650.38720.08880.048*
C270.5064 (3)0.41786 (11)0.09241 (7)0.0546 (4)
H27A0.66940.43210.0970.082*0.5
H27B0.40090.47220.10560.082*0.5
H27C0.48220.36990.12030.082*0.5
H27D0.36560.41740.11820.082*0.5
H27E0.63410.37730.10970.082*0.5
H27F0.55280.47960.0950.082*0.5
S1A0.03887 (5)0.84904 (2)0.557886 (14)0.03438 (9)
S2A0.12726 (6)0.76554 (2)0.184136 (15)0.04023 (9)
C1A0.1026 (2)0.87023 (8)0.47906 (5)0.0304 (2)
H1A10.0980.93620.46680.037*
H1A20.26850.8440.48030.037*
C2A0.0309 (2)0.82581 (8)0.42979 (6)0.0314 (2)
H2A10.0170.75950.44140.038*
H2A20.19920.84860.43210.038*
C3A0.0611 (2)0.84496 (8)0.36032 (6)0.0320 (2)
H3A10.23010.82320.35820.038*
H3A20.04460.91120.34840.038*
C4A0.0691 (2)0.79927 (8)0.31102 (6)0.0330 (2)
H4A10.05310.73290.32260.04*
H4A20.2380.82130.31250.04*
C5A0.0293 (2)0.81981 (8)0.24225 (6)0.0348 (3)
H5A10.1980.79750.24060.042*
H5A20.01370.88610.23060.042*
C11A0.13591 (19)0.89409 (7)0.61353 (5)0.0280 (2)
C12A0.3278 (2)0.94183 (8)0.59637 (6)0.0320 (2)
H12A0.37390.95190.55180.038*
C13A0.4519 (2)0.97471 (8)0.64446 (6)0.0337 (3)
H13A0.58251.00720.6320.04*
C14A0.3910 (2)0.96155 (8)0.71021 (6)0.0321 (2)
C15A0.1984 (2)0.91322 (8)0.72665 (6)0.0349 (3)
H15A0.15260.90310.77120.042*
C16A0.0728 (2)0.87984 (8)0.67958 (6)0.0335 (3)
H16A0.05710.8470.69210.04*
C17A0.5269 (2)0.99751 (10)0.76193 (7)0.0422 (3)
H17G0.661.02630.74150.063*
H17H0.58460.94740.79360.063*
H17I0.42431.04220.78430.063*
C21A0.0231 (2)0.81398 (8)0.10834 (6)0.0330 (2)
C22A0.1589 (2)0.81022 (8)0.05391 (6)0.0380 (3)
H22A0.29980.78180.05850.046*
C23A0.0901 (3)0.84768 (9)0.00686 (6)0.0442 (3)
H23A0.18420.84380.04360.053*
C24A0.1144 (3)0.89095 (9)0.01533 (6)0.0428 (3)
C25A0.2483 (2)0.89386 (9)0.03914 (7)0.0433 (3)
H25A0.38830.92290.03450.052*
C26A0.1841 (2)0.85568 (9)0.10038 (6)0.0399 (3)
H26A0.2810.85790.13670.048*
C27A0.1903 (3)0.93199 (11)0.08128 (7)0.0590 (4)
H27G0.06890.9280.11310.088*
H27H0.33750.89890.0950.088*
H27I0.21380.99570.07860.088*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.03288 (15)0.04141 (17)0.02700 (15)0.01181 (12)0.00068 (11)0.00653 (12)
S20.0536 (2)0.04460 (19)0.02717 (16)0.02117 (14)0.00305 (13)0.00360 (13)
C10.0319 (5)0.0308 (6)0.0261 (5)0.0043 (4)0.0016 (4)0.0031 (4)
C20.0353 (6)0.0306 (6)0.0270 (6)0.0059 (4)0.0023 (5)0.0024 (4)
C30.0359 (6)0.0309 (6)0.0271 (6)0.0059 (5)0.0025 (5)0.0023 (4)
C40.0385 (6)0.0319 (6)0.0270 (6)0.0075 (5)0.0025 (5)0.0035 (5)
C50.0407 (6)0.0383 (6)0.0270 (6)0.0098 (5)0.0030 (5)0.0042 (5)
C110.0280 (5)0.0274 (5)0.0258 (5)0.0014 (4)0.0005 (4)0.0038 (4)
C120.0325 (6)0.0344 (6)0.0265 (6)0.0063 (5)0.0019 (4)0.0029 (4)
C130.0307 (6)0.0344 (6)0.0334 (6)0.0081 (5)0.0003 (5)0.0035 (5)
C140.0312 (6)0.0304 (6)0.0298 (6)0.0009 (4)0.0035 (4)0.0058 (4)
C150.0351 (6)0.0369 (6)0.0248 (5)0.0015 (5)0.0012 (4)0.0035 (5)
C160.0309 (6)0.0351 (6)0.0292 (6)0.0057 (4)0.0023 (4)0.0018 (5)
C170.0397 (7)0.0469 (7)0.0348 (7)0.0040 (5)0.0071 (5)0.0118 (5)
C210.0396 (6)0.0317 (6)0.0260 (6)0.0071 (5)0.0036 (5)0.0062 (4)
C220.0374 (6)0.0430 (7)0.0358 (7)0.0036 (5)0.0049 (5)0.0021 (5)
C230.0378 (7)0.0493 (7)0.0362 (7)0.0030 (5)0.0025 (5)0.0061 (6)
C240.0496 (7)0.0356 (6)0.0290 (6)0.0107 (5)0.0047 (5)0.0050 (5)
C250.0450 (7)0.0488 (8)0.0350 (7)0.0032 (6)0.0118 (5)0.0011 (6)
C260.0354 (6)0.0504 (7)0.0353 (7)0.0002 (5)0.0024 (5)0.0080 (6)
C270.0749 (11)0.0600 (9)0.0313 (7)0.0205 (8)0.0014 (7)0.0010 (6)
S1A0.03389 (16)0.04282 (17)0.02890 (16)0.01300 (12)0.00289 (11)0.00710 (12)
S2A0.05185 (19)0.04138 (18)0.03061 (17)0.01794 (14)0.00394 (13)0.00413 (13)
C1A0.0326 (6)0.0312 (6)0.0278 (6)0.0038 (4)0.0004 (4)0.0036 (4)
C2A0.0356 (6)0.0299 (6)0.0292 (6)0.0056 (5)0.0010 (5)0.0024 (5)
C3A0.0372 (6)0.0307 (6)0.0287 (6)0.0064 (5)0.0011 (5)0.0030 (5)
C4A0.0396 (6)0.0310 (6)0.0292 (6)0.0061 (5)0.0026 (5)0.0034 (5)
C5A0.0421 (7)0.0341 (6)0.0295 (6)0.0083 (5)0.0042 (5)0.0033 (5)
C11A0.0285 (5)0.0272 (5)0.0285 (6)0.0019 (4)0.0009 (4)0.0038 (4)
C12A0.0330 (6)0.0349 (6)0.0284 (6)0.0068 (5)0.0041 (5)0.0025 (5)
C13A0.0314 (6)0.0358 (6)0.0351 (6)0.0086 (5)0.0026 (5)0.0048 (5)
C14A0.0331 (6)0.0319 (6)0.0317 (6)0.0025 (5)0.0014 (5)0.0060 (5)
C15A0.0384 (6)0.0394 (6)0.0272 (6)0.0063 (5)0.0030 (5)0.0032 (5)
C16A0.0339 (6)0.0371 (6)0.0303 (6)0.0092 (5)0.0038 (5)0.0024 (5)
C17A0.0423 (7)0.0496 (8)0.0372 (7)0.0100 (6)0.0038 (6)0.0106 (6)
C21A0.0376 (6)0.0307 (6)0.0303 (6)0.0003 (5)0.0027 (5)0.0046 (5)
C22A0.0408 (7)0.0371 (6)0.0371 (7)0.0014 (5)0.0063 (5)0.0097 (5)
C23A0.0573 (8)0.0424 (7)0.0324 (7)0.0040 (6)0.0104 (6)0.0081 (5)
C24A0.0546 (8)0.0380 (7)0.0330 (6)0.0066 (6)0.0039 (6)0.0035 (5)
C25A0.0418 (7)0.0458 (7)0.0413 (7)0.0029 (6)0.0039 (6)0.0016 (6)
C26A0.0377 (6)0.0463 (7)0.0354 (7)0.0034 (5)0.0051 (5)0.0024 (5)
C27A0.0834 (12)0.0535 (9)0.0357 (8)0.0062 (8)0.0123 (7)0.0004 (6)
Geometric parameters (Å, º) top
S1—C111.7648 (12)C27—H27D0.98
S1—C11.8119 (12)C27—H27E0.98
S2—C211.7737 (12)C27—H27F0.98
S2—C51.8254 (12)S1A—C11A1.7665 (12)
C1—C21.5274 (16)S1A—C1A1.8091 (12)
C1—H1A0.99S2A—C21A1.7714 (12)
C1—H1B0.99S2A—C5A1.8136 (12)
C2—C31.5259 (16)C1A—C2A1.5268 (16)
C2—H2A0.99C1A—H1A10.99
C2—H2B0.99C1A—H1A20.99
C3—C41.5285 (16)C2A—C3A1.5223 (16)
C3—H3A0.99C2A—H2A10.99
C3—H3B0.99C2A—H2A20.99
C4—C51.5246 (16)C3A—C4A1.5270 (16)
C4—H4A0.99C3A—H3A10.99
C4—H4B0.99C3A—H3A20.99
C5—H5A0.99C4A—C5A1.5249 (16)
C5—H5B0.99C4A—H4A10.99
C11—C121.3950 (16)C4A—H4A20.99
C11—C161.4006 (15)C5A—H5A10.99
C12—C131.3886 (17)C5A—H5A20.99
C12—H120.95C11A—C12A1.3917 (16)
C13—C141.3914 (16)C11A—C16A1.3995 (16)
C13—H130.95C12A—C13A1.3904 (17)
C14—C151.3989 (17)C12A—H12A0.95
C14—C171.5083 (16)C13A—C14A1.3893 (17)
C15—C161.3829 (17)C13A—H13A0.95
C15—H150.95C14A—C15A1.3979 (17)
C16—H160.95C14A—C17A1.5071 (17)
C17—H17A0.98C15A—C16A1.3826 (17)
C17—H17B0.98C15A—H15A0.95
C17—H17C0.98C16A—H16A0.95
C17—H17D0.98C17A—H17G0.98
C17—H17E0.98C17A—H17H0.98
C17—H17F0.98C17A—H17I0.98
C21—C261.3850 (17)C21A—C22A1.3917 (17)
C21—C221.3898 (17)C21A—C26A1.3966 (18)
C22—C231.3843 (18)C22A—C23A1.3853 (19)
C22—H220.95C22A—H22A0.95
C23—C241.3871 (19)C23A—C24A1.396 (2)
C23—H230.95C23A—H23A0.95
C24—C251.3816 (19)C24A—C25A1.384 (2)
C24—C271.5069 (18)C24A—C27A1.5073 (19)
C25—C261.3878 (18)C25A—C26A1.3895 (18)
C25—H250.95C25A—H25A0.95
C26—H260.95C26A—H26A0.95
C27—H27A0.98C27A—H27G0.98
C27—H27B0.98C27A—H27H0.98
C27—H27C0.98C27A—H27I0.98
C11—S1—C1105.56 (5)C24—C27—H27D109.5
C21—S2—C5102.19 (6)H27A—C27—H27D141.1
C2—C1—S1106.39 (8)H27B—C27—H27D56.3
C2—C1—H1A110.5H27C—C27—H27D56.3
S1—C1—H1A110.5C24—C27—H27E109.5
C2—C1—H1B110.5H27A—C27—H27E56.3
S1—C1—H1B110.5H27B—C27—H27E141.1
H1A—C1—H1B108.6H27C—C27—H27E56.3
C3—C2—C1113.25 (9)H27D—C27—H27E109.5
C3—C2—H2A108.9C24—C27—H27F109.5
C1—C2—H2A108.9H27A—C27—H27F56.3
C3—C2—H2B108.9H27B—C27—H27F56.3
C1—C2—H2B108.9H27C—C27—H27F141.1
H2A—C2—H2B107.7H27D—C27—H27F109.5
C2—C3—C4110.84 (10)H27E—C27—H27F109.5
C2—C3—H3A109.5C11A—S1A—C1A105.09 (5)
C4—C3—H3A109.5C21A—S2A—C5A102.30 (6)
C2—C3—H3B109.5C2A—C1A—S1A107.21 (8)
C4—C3—H3B109.5C2A—C1A—H1A1110.3
H3A—C3—H3B108.1S1A—C1A—H1A1110.3
C5—C4—C3112.47 (10)C2A—C1A—H1A2110.3
C5—C4—H4A109.1S1A—C1A—H1A2110.3
C3—C4—H4A109.1H1A1—C1A—H1A2108.5
C5—C4—H4B109.1C3A—C2A—C1A112.15 (10)
C3—C4—H4B109.1C3A—C2A—H2A1109.2
H4A—C4—H4B107.8C1A—C2A—H2A1109.2
C4—C5—S2108.48 (8)C3A—C2A—H2A2109.2
C4—C5—H5A110C1A—C2A—H2A2109.2
S2—C5—H5A110H2A1—C2A—H2A2107.9
C4—C5—H5B110C2A—C3A—C4A112.32 (10)
S2—C5—H5B110C2A—C3A—H3A1109.1
H5A—C5—H5B108.4C4A—C3A—H3A1109.1
C12—C11—C16118.61 (10)C2A—C3A—H3A2109.1
C12—C11—S1125.13 (9)C4A—C3A—H3A2109.1
C16—C11—S1116.26 (9)H3A1—C3A—H3A2107.9
C13—C12—C11120.12 (10)C5A—C4A—C3A110.57 (10)
C13—C12—H12119.9C5A—C4A—H4A1109.5
C11—C12—H12119.9C3A—C4A—H4A1109.5
C12—C13—C14121.89 (11)C5A—C4A—H4A2109.5
C12—C13—H13119.1C3A—C4A—H4A2109.5
C14—C13—H13119.1H4A1—C4A—H4A2108.1
C13—C14—C15117.42 (11)C4A—C5A—S2A110.17 (8)
C13—C14—C17121.49 (11)C4A—C5A—H5A1109.6
C15—C14—C17121.09 (11)S2A—C5A—H5A1109.6
C16—C15—C14121.49 (11)C4A—C5A—H5A2109.6
C16—C15—H15119.3S2A—C5A—H5A2109.6
C14—C15—H15119.3H5A1—C5A—H5A2108.1
C15—C16—C11120.47 (11)C12A—C11A—C16A118.75 (11)
C15—C16—H16119.8C12A—C11A—S1A124.98 (9)
C11—C16—H16119.8C16A—C11A—S1A116.28 (9)
C14—C17—H17A109.5C13A—C12A—C11A119.97 (11)
C14—C17—H17B109.5C13A—C12A—H12A120
H17A—C17—H17B109.5C11A—C12A—H12A120
C14—C17—H17C109.5C14A—C13A—C12A122.03 (11)
H17A—C17—H17C109.5C14A—C13A—H13A119
H17B—C17—H17C109.5C12A—C13A—H13A119
C14—C17—H17D109.5C13A—C14A—C15A117.29 (11)
H17A—C17—H17D141.1C13A—C14A—C17A121.57 (11)
H17B—C17—H17D56.3C15A—C14A—C17A121.14 (11)
H17C—C17—H17D56.3C16A—C15A—C14A121.59 (11)
C14—C17—H17E109.5C16A—C15A—H15A119.2
H17A—C17—H17E56.3C14A—C15A—H15A119.2
H17B—C17—H17E141.1C15A—C16A—C11A120.38 (11)
H17C—C17—H17E56.3C15A—C16A—H16A119.8
H17D—C17—H17E109.5C11A—C16A—H16A119.8
C14—C17—H17F109.5C14A—C17A—H17G109.5
H17A—C17—H17F56.3C14A—C17A—H17H109.5
H17B—C17—H17F56.3H17G—C17A—H17H109.5
H17C—C17—H17F141.1C14A—C17A—H17I109.5
H17D—C17—H17F109.5H17G—C17A—H17I109.5
H17E—C17—H17F109.5H17H—C17A—H17I109.5
C26—C21—C22118.36 (11)C22A—C21A—C26A118.74 (12)
C26—C21—S2119.88 (10)C22A—C21A—S2A117.21 (10)
C22—C21—S2121.66 (9)C26A—C21A—S2A124.05 (10)
C23—C22—C21120.69 (11)C23A—C22A—C21A120.49 (13)
C23—C22—H22119.7C23A—C22A—H22A119.8
C21—C22—H22119.7C21A—C22A—H22A119.8
C22—C23—C24121.22 (12)C22A—C23A—C24A121.39 (13)
C22—C23—H23119.4C22A—C23A—H23A119.3
C24—C23—H23119.4C24A—C23A—H23A119.3
C25—C24—C23117.71 (11)C25A—C24A—C23A117.50 (12)
C25—C24—C27121.70 (12)C25A—C24A—C27A120.79 (14)
C23—C24—C27120.58 (13)C23A—C24A—C27A121.71 (14)
C24—C25—C26121.62 (12)C24A—C25A—C26A122.06 (13)
C24—C25—H25119.2C24A—C25A—H25A119
C26—C25—H25119.2C26A—C25A—H25A119
C21—C26—C25120.38 (12)C25A—C26A—C21A119.82 (12)
C21—C26—H26119.8C25A—C26A—H26A120.1
C25—C26—H26119.8C21A—C26A—H26A120.1
C24—C27—H27A109.5C24A—C27A—H27G109.5
C24—C27—H27B109.5C24A—C27A—H27H109.5
H27A—C27—H27B109.5H27G—C27A—H27H109.5
C24—C27—H27C109.5C24A—C27A—H27I109.5
H27A—C27—H27C109.5H27G—C27A—H27I109.5
H27B—C27—H27C109.5H27H—C27A—H27I109.5
C11—S1—C1—C2175.56 (7)C11A—S1A—C1A—C2A175.59 (8)
S1—C1—C2—C3174.21 (8)S1A—C1A—C2A—C3A175.80 (8)
C1—C2—C3—C4178.93 (9)C1A—C2A—C3A—C4A178.99 (10)
C2—C3—C4—C5176.52 (10)C2A—C3A—C4A—C5A179.72 (10)
C3—C4—C5—S2176.47 (8)C3A—C4A—C5A—S2A179.81 (8)
C21—S2—C5—C4171.38 (8)C21A—S2A—C5A—C4A170.04 (8)
C1—S1—C11—C124.37 (12)C1A—S1A—C11A—C12A4.87 (12)
C1—S1—C11—C16175.58 (8)C1A—S1A—C11A—C16A175.20 (9)
C16—C11—C12—C130.17 (17)C16A—C11A—C12A—C13A0.31 (17)
S1—C11—C12—C13179.79 (9)S1A—C11A—C12A—C13A179.62 (9)
C11—C12—C13—C140.04 (18)C11A—C12A—C13A—C14A0.00 (19)
C12—C13—C14—C150.15 (17)C12A—C13A—C14A—C15A0.20 (18)
C12—C13—C14—C17179.46 (11)C12A—C13A—C14A—C17A179.99 (11)
C13—C14—C15—C160.23 (17)C13A—C14A—C15A—C16A0.09 (18)
C17—C14—C15—C16179.39 (11)C17A—C14A—C15A—C16A179.90 (12)
C14—C15—C16—C110.10 (18)C14A—C15A—C16A—C11A0.22 (19)
C12—C11—C16—C150.10 (17)C12A—C11A—C16A—C15A0.41 (18)
S1—C11—C16—C15179.86 (9)S1A—C11A—C16A—C15A179.52 (9)
C5—S2—C21—C26119.79 (11)C5A—S2A—C21A—C22A159.84 (10)
C5—S2—C21—C2264.01 (11)C5A—S2A—C21A—C26A19.71 (12)
C26—C21—C22—C231.01 (19)C26A—C21A—C22A—C23A0.38 (18)
S2—C21—C22—C23175.24 (10)S2A—C21A—C22A—C23A179.19 (10)
C21—C22—C23—C240.4 (2)C21A—C22A—C23A—C24A0.73 (19)
C22—C23—C24—C250.9 (2)C22A—C23A—C24A—C25A0.97 (19)
C22—C23—C24—C27177.69 (13)C22A—C23A—C24A—C27A179.92 (12)
C23—C24—C25—C260.1 (2)C23A—C24A—C25A—C26A0.1 (2)
C27—C24—C25—C26178.68 (13)C27A—C24A—C25A—C26A179.23 (13)
C22—C21—C26—C252.00 (19)C24A—C25A—C26A—C21A1.0 (2)
S2—C21—C26—C25174.33 (10)C22A—C21A—C26A—C25A1.22 (19)
C24—C25—C26—C211.6 (2)S2A—C21A—C26A—C25A178.33 (10)

Experimental details

Crystal data
Chemical formulaC19H24S2
Mr316.5
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)5.7350 (3), 14.8989 (7), 20.5873 (9)
α, β, γ (°)84.586 (4), 88.355 (4), 83.937 (4)
V3)1741.13 (14)
Z4
Radiation typeMo Kα
µ (mm1)0.30
Crystal size (mm)0.37 × 0.32 × 0.3
Data collection
DiffractometerStoe IPDS II two-circle
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.898, 0.916
No. of measured, independent and
observed [I > 2σ(I)] reflections
31941, 7762, 6312
Rint0.046
(sin θ/λ)max1)0.644
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.095, 1.00
No. of reflections7762
No. of parameters383
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.17, 0.40

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP (Sheldrick, 2008), WinGX (Farrugia, 1999).

 

Acknowledgements

This work was supported by a grant from the Universidad de Antofagasta (DI-1324–06). We thank the Spanish Research Council (CSIC) for providing us with a free-of-charge licence for the CSD system. JA thanks the Universidad de Antofagasta for PhD fellowships.

References

First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–38.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBrito, I., López-Rodríguez, M., Vargas, D. & León, Y. (2006). Acta Cryst. E62, o914–o916.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBrito, I., Vargas, D., León, Y., Cárdenas, A., López-Rodríguez, M. & Wittke, O. (2004). Acta Cryst. E60, o1668–o1670.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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First citationMurray, S. G. & Hartley, F. R. (1981). Chem. Rev. 81, 365–414.  CrossRef CAS Web of Science Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2003). J. Appl. Cryst. 36, 7–13.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationStoe & Cie (2001). X-AREA and X-RED. Stoe & Cie, Darmstadt, Germany.  Google Scholar
First citationWithersby, M. A., Blake, A. J., Champness, N. R., Hubberstey, P., Li, W. S. & Schröder, M. (1997). Angew. Chem. Int. Ed. Engl. 36, 2327–2329.  CSD CrossRef CAS Web of Science Google Scholar

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