Tris[4-(methyl­sulfan­yl)phen­yl]arsine

Omar bin Shawkataly; Imthyaz Ahmed Khan; Chin Sing Yeap; Hoong-Kun Fun

doi:10.1107/S160053681002876X

. 2010 Jul 24;66(Pt 8):o2116. doi: 10.1107/S160053681002876X

Tris[4-(methylsulfanyl)phenyl]arsine

Omar bin Shawkataly ^a,^*,^‡, Imthyaz Ahmed Khan ^a,^§, Chin Sing Yeap ^b,^¶, Hoong-Kun Fun ^b,^‡‡

PMCID: PMC3007364 PMID: 21588406

Abstract

In the title compound, C₂₁H₂₁AsS₃, the three benzene rings make dihedral angles of 88.41 (10), 87.75 (9) and 74.74 (10)° with each other. The methylsulfanyl groups are roughly coplanar with their attached benzene rings [C—S—C—C torsion angles = −7.6 (2), 11.2 (2) and 4.1 (2)°]. In the crystal, weak C—H⋯π interactions link the molecules.

Related literature

For related structures of trisarylarsines with osmium and ruthenium, see: Cullen et al. (1995 ▶); Shawkataly et al. (2009a ▶,b ▶, 2010a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₁H₂₁AsS₃
M _r = 444.48
Monoclinic,
a = 11.0839 (2) Å
b = 11.4556 (2) Å
c = 17.3247 (2) Å
β = 110.860 (1)°
V = 2055.58 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.96 mm⁻¹
T = 100 K
0.35 × 0.13 × 0.11 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.545, T _max = 0.821
31130 measured reflections
7111 independent reflections
5098 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.097
S = 1.01
7111 reflections
229 parameters
H-atom parameters constrained
Δρ_max = 0.86 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681002876X/hb5559sup1.cif

e-66-o2116-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681002876X/hb5559Isup2.hkl

e-66-o2116-Isup2.hkl^{(348KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C7–C12 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C21—H21A⋯Cg1ⁱ	0.96	2.55	3.441 (3)	155

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research grant No. 1001/PJJAUH/811115. IAK is grateful to USM for a Visiting Researcher position. HKF and CSY thank USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY also thanks USM for the award of a USM Fellowship.

supplementary crystallographic information

Comment

Trisarylarsines are used in the synthesis of osmium and ruthenium cluster derivatives (Cullen et al., 1995; Shawkataly et al., 2009a, b, 2010a, b).

The three benzene rings of the title compound (Fig. 1) make dihedral angles (C1–C6/C7–C12, C1–C6/C13–C18 and C7–C12/C13–C18) of 88.41 (10), 87.75 (9) and 74.74 (10)° with each other respectively. The methylsulfanyl groups are nearly coplanar with the attached benzene rings [torsion angles of C19–S1–C4–C3 = -7.6 (2), C20–S2–C10–C9 = 11.2 (2) and C21–S3–C16–C17 = 4.1 (2)°]. In the crystal structure, the molecules are stacked along a axis (Fig. 2). Weak intermolecular C—H···π interactions further stabilize the crystal structure (Table 1).

Experimental

The reactions were conducted under an atmosphere of high purity nitrogen using standard Schlenk techniques and tetrahydrofuran (THF) dried over sodium metal. Tris(4-(methylsulfanyl)phenyl)arsine was prepared from arsenic trichloride and 4-(methylsulfanyl)phenylmagnesium bromide in tetrahydrofuran. Colourless blocks of (I) were obtained by slow evaporation from a chloroform solution.