Tris(1-naphth­yl)arsine chloro­form solvate

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

doi:10.1107/S1600536809041646

. 2009 Oct 17;65(Pt 11):o2772–o2773. doi: 10.1107/S1600536809041646

Tris(1-naphthyl)arsine chloroform solvate

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

PMCID: PMC2971302 PMID: 21578366

Abstract

In the title compound, C₃₀H₂₁As·CHCl₃, the dihedral angles between the three naphthalene ring systems [r.m.s. deviations = 0.007, 0.009 and 0.020 Å] are 72.54 (4), 88.05 (4) and 83.36 (4)°. In the crystal, the molecules are stacked down the a axis being consolidated by C—H⋯π and π–π interactions [centroid to centroid distance = 3.7839 (7) Å].

Related literature

For general background to tris(1-naphthyl)arsine, see: Cullen et al. (1995 ▶). For related structures, see: Kamepalli et al. (1996 ▶); Shawkataly et al. (2009 ▶). For the synthesis, see: Burfield et al. (1977 ▶, 1978 ▶); Burfield & Smithers (1978 ▶); Michaelis (1902 ▶). For description of the Cambridge Structural Database, see: Allen (2002 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₃₀H₂₁As·CHCl₃
M _r = 575.76
Triclinic,
a = 9.1326 (2) Å
b = 11.9473 (2) Å
c = 12.3971 (2) Å
α = 77.432 (1)°
β = 87.455 (1)°
γ = 75.434 (1)°
V = 1277.72 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.66 mm⁻¹
T = 100 K
0.62 × 0.23 × 0.10 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.427, T _max = 0.849
37994 measured reflections
7382 independent reflections
6791 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.023
wR(F ²) = 0.061
S = 1.04
7382 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809041646/tk2554sup1.cif

e-65-o2772-sup1.cif^{(24.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809041646/tk2554Isup2.hkl

e-65-o2772-Isup2.hkl^{(361.2KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯Cg1ⁱ	0.93	2.68	3.6013 (14)	169
C14—H14A⋯Cg2ⁱⁱ	0.93	2.86	3.7421 (15)	160

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) . Cg1 and Cg2 are centroids of the C25–C30 and C5–C10 benzene rings, respectively.

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 postdoctoral Fellowship and Gokhale Centenary College, Ankola, Karnataka, India for study leave. HKF thanks USM for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY thanks USM for the award of a USM Fellowship.

supplementary crystallographic information

Comment

Tris(1-naphthyl)arsine has been used in the synthesis of osmium and ruthenium cluster derivatives (Cullen et al., 1995). A search of the Cambridge Structural Database (Allen, 2002) revealed no structure containing this molecule. Among substituted naphthylarsines, only the structure of tris[8-(dimethylamino)-1-naphthyl]arsine (Kamepalli et al., 1996) is known.

The asymmetric unit of the title compound comprises a molecule of tris(1-naphthyl)arsine and a solvent chloroform molecule (Fig. 1). The As–C bond lengths lie in the range 1.9595 (11) to 1.9635 (12) Å, and the C–As–C angles lie in the range 98.97 (5) to 100.92 (5) °. The values are comparable to those found in related structures (Kamepalli et al., 1996; Shawkataly et al., 2009). The dihedral angles between the three naphthalene ring systems (C1–C10/C11–C20, C1–C10/C21–C30 and C11–C20/C21–C30) are 72.54 (4), 88.05 (4) and 83.36 (4)°, respectively. In the crystal packing (Fig. 2), the molecules are stacked down the a axis being consolidated by C—H···π (Table 1) and π–π interactions [Cg1···Cg3ⁱⁱⁱ = 3.7839 (7) Å; Cg1 and Cg3 are centroids of benzene rings C25–C30 and C21–C25/C30, respectively; (iii) -x, 2 - y, 1 - z].

Experimental

Solvents were dried by recommended literature routes (Burfield et al., 1977, 1978; Burfield & Smithers, 1978). Tris(1-naphthyl)arsine was prepared from arsenic trichloride and 1-bromonaphthalene (Michaelis, 1902). Crystals were obtained by slow evaporation from its chloroform solution.