Tris(3-amino­phen­yl)phosphine oxide ethanol solvate

Jun Han; Wenguang Li; Shufang Wang; Juli Jiang

doi:10.1107/S160053680900909X

. 2009 Mar 25;65(Pt 4):o839. doi: 10.1107/S160053680900909X

Tris(3-aminophenyl)phosphine oxide ethanol solvate

Jun Han ^a, Wenguang Li ^b, Shufang Wang ^b, Juli Jiang ^a,^*

PMCID: PMC2969104 PMID: 21582558

Abstract

The title compound crystallized as an ethanol solvate, C₁₈H₁₈N₃OP·C₂H₆O. It is the reduction product of tris(3-nitrophenyl)phosphine oxide. In the crystal, there are intermolecular N—H⋯O hydrogen bonds between neighbouring tris(3-aminophenyl)phosphine oxide molecules and O—H⋯O hydrogen bonds involving the ethanol solvent molecule.

Related literature

The structure of tris(3-nitrophenyl)phosphine oxide is described by Jean-Noël et al. (2004 ▶). For literature on related compounds, see: Michaelis et al. (1885 ▶); Dressick et al. (2000 ▶); Hessler & Stelzer (1997 ▶).

Experimental

Crystal data

C₁₈H₁₈N₃OP·C₂H₆O
M _r = 369.39
Triclinic,
a = 9.1046 (13) Å
b = 10.7595 (15) Å
c = 12.020 (3) Å
α = 109.131 (3)°
β = 94.245 (3)°
γ = 114.028 (2)°
V = 986.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.16 mm⁻¹
T = 293 K
0.35 × 0.34 × 0.30 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.947, T _max = 0.954
5014 measured reflections
3420 independent reflections
1659 reflections with I > 2σ(I)
R _int = 0.058

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.149
S = 0.85
3420 reflections
174 parameters
H-atom parameters constrained
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: SMART (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900909X/pk2158sup1.cif

e-65-0o839-sup1.cif^{(20.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680900909X/pk2158Isup2.hkl

e-65-0o839-Isup2.hkl^{(167.7KB, 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
N3—H3A⋯N1ⁱ	0.86	2.62	3.469 (6)	168
N2—H2B⋯O1ⁱⁱ	0.86	2.14	2.987 (4)	168
N2—H2C⋯O2ⁱⁱⁱ	0.86	2.23	3.089 (5)	173
O2—H2⋯O1	0.82	1.85	2.672 (3)	178

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

Acknowledgments

The authors gratefully acknowledge the financial support of the NSFC (grant No. 20602017), the Program for New Century Excellent Talents in University (grant No. NCET-07-0425) and the Natural Science Foundation of Jiangsu (grant No. BK 2008259).

supplementary crystallographic information

Comment

Arylphosphines have been investigated extensively as ionic ligands for catalytically active transition metals in aqueous solution (Hessler & Stelzer, 1997), as starting materials for the molecular fabrication of materials (Dressick et al., 2000) and so on. As early as 1885, tris(3-aminophenyl)phosphine oxide had been synthesized in the Sn/HCl system but with low yield (Michaelis et al., 1885). The molecules of the title compound crystallized as an ethanol solvate (Fig. 1). Adjacent molecules are linked via intermolecular O—H···O and N—H···O interactions, such as O2—H2···O1, N2—H2B···O1, N2—H2C···O2 and N1—H1A···O2 from a neighboring molecule (Fig. 2).

Experimental

The precursor, tris(3-nitrophenyl)phosphine oxide (1.032 g, 2.5 mmol), was added to a mixture of ethanol (30 ml), THF (30 ml), hydrazine hydrate (10 ml) and a catalytic amount of Raney Ni in a 100 ml flask. The mixture was heated to reflux and reaction progress was monitored by TLC. The pure product was obtained as colorless crystals suitable for X-ray analysis after removing most of the solvent and without further purification (yield > 99%).