Triphen­yl[2-(triphenyl­phosphanium­yl)eth­yl]phosphanium bis­(periodate)

Mostafa Gholizadeh; Farrokhzad Mohammadi Zonoz; Mehrdad Pourayoubi; Maliheh Ebrahimpour; Maryam Salehabadi

doi:10.1107/S1600536811008725

. 2011 Mar 12;67(Pt 4):o863. doi: 10.1107/S1600536811008725

Triphenyl[2-(triphenylphosphaniumyl)ethyl]phosphanium bis(periodate)

Mostafa Gholizadeh ^a,^*, Farrokhzad Mohammadi Zonoz ^b, Mehrdad Pourayoubi ^a, Maliheh Ebrahimpour ^b, Maryam Salehabadi ^b

PMCID: PMC3099791 PMID: 21754144

Abstract

In title salt, C₃₈H₃₄P₂ ²⁺·2IO₄ ⁻, the P atoms of the dication and the I atoms of the periodate anions are each in a slightly distorted tetrahedral environment. In the dication, the two –P(C₆H₅)₃ groups adopt a gauche conformation with respect to each other. In the crystal, several C—H⋯O hydrogen bonds between the cations and anions lead to a two-dimensional arrangement along (101).

Related literature

For the synthesis and structures of related compounds, see: Barkell et al. (2008 ▶); Rizzoli et al. (2010 ▶).

Experimental

Crystal data

C₃₈H₃₄P₂ ²⁺·2IO₄ ⁻
M _r = 934.39
Monoclinic,
a = 9.2077 (18) Å
b = 18.387 (4) Å
c = 21.992 (4) Å
β = 94.37 (3)°
V = 3712.5 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.83 mm⁻¹
T = 298 K
0.5 × 0.2 × 0.2 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE; Stoe & Cie, 2005 ▶)] T _min = 0.649, T _max = 0.692
26606 measured reflections
9970 independent reflections
7229 reflections with I > 2σ(I)
R _int = 0.077

Refinement

R[F ² > 2σ(F ²)] = 0.069
wR(F ²) = 0.190
S = 1.17
9970 reflections
451 parameters
H-atom parameters constrained
Δρ_max = 1.18 e Å⁻³
Δρ_min = −1.69 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA ▶); data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811008725/sj5109sup1.cif

e-67-0o863-sup1.cif^{(28.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008725/sj5109Isup2.hkl

e-67-0o863-Isup2.hkl^{(487.6KB, 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
C30—H30⋯O5ⁱ	0.93	2.43	3.351 (10)	172
C20—H20B⋯O8ⁱⁱ	0.97	2.38	3.338 (11)	170
C19—H19B⋯O4	0.97	2.44	3.397 (8)	171
C19—H19A⋯O7	0.97	2.30	3.135 (8)	144

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

Support of this investigation by Ferdowsi University of Mashhad and Sabzevar Tarbiat Moallem University Councils is gratefully acknowledged.

supplementary crystallographic information

Comment

In previous work, the syntheses and X-ray structures of some phosphonium salts, such as [C₆H₅–C₆H₄C(O)CH₂P(C₆H₅)₃]⁺[CF₃SO₃]^- (Rizzoli et al., 2010) and [(C₆H₅)₃PCH₂C₆H₂(OCH₃)₃]⁺Cl^-H₂O (Barkell et al., 2008) have been investigated. We report here the synthesis and crystal structure of a new phosphonium salt, [P(C₆H₅)₃CH₂CH₂P(C₆H₅)₃]²⁺, 2[IO₄]^- (Fig. 1). In the cation of the title salt, the phosphorus atoms are found in a slightly distorted tetrahedral environment; the bond angles around the P atoms are in the range of 106.6 (3)° to 112.0 (3)° for P1 and 107.9 (3)° to 110.4 (3)° for P2. The two P(C₆H₅)₃ groups are gauche to each other, the torsion angle P1—C19—C20—P2 is 136.1 (3)°. The I atoms of the two symmetrically independent periodate anions (labeled with I1 and I2) also display slightly distorted tetrahedral environments; for example, the bond angles around I1 are in the range of 108.0 (3)° to 111.2 (4)°. Several C—H···O hydrogen bonds (C···O distances are in the range of 3.135 (8) Å to 3.397 (8) Å) between the cations and anions lead to a two-dimensional arrangement along the (101) plane.

Experimental

Preparation of bis (triphenylphosphonium) 1,2-ethane bromide: 1,2-Dibromoethane (15 mmol) was added to triphenylphosphine (30 mmol) and refluxed. After 5 h, the precipitate was filtered and washed with diethyl ether and dried.

Preparation of title salt: To a solution of bis (triphenylphosphonium) 1,2-ethane bromide (10 mmol) in H₂O (25 ml), a solution of NaIO₄ (20 mmol) in H₂O (25 ml) was added and stirred. After 24 h, the precipitate was filtered and washed with H₂O and crystallized from CH₃CN at room temperature.