Tris(2-methoxy­phen­yl)phosphine

Omar bin Shawkataly; Mohd Aslam A Pankhi; Imthyaz Ahmed Khan; Chin Sing Yeap; Hoong-Kun Fun

doi:10.1107/S1600536809020595

. 2009 Jun 6;65(Pt 7):o1525–o1526. doi: 10.1107/S1600536809020595

Tris(2-methoxyphenyl)phosphine

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

PMCID: PMC2969262 PMID: 21582816

Abstract

In the title compound, C₂₁H₂₁O₃P, the whole molecule is disordered over two sets of positions with refined occupancies of 0.503 (1) and 0.497 (1). The dihedral angles between the three benzene rings are 72.9 (2)°, 82.9 (3)° and 70.0 (2)° in the major disorder component and the corresponding angles in the minor disorder component are 85.0 (2)°, 79.2 (2)° and 72.3 (2)°. The crystal structure is stabilized by C—H⋯π interactions.

Related literature

For P–C bond lengths and C–P–C angles, see: Uttecht et al. (2005 ▶). For the stereochemistry of tris(2-methoxyphenyl) phosphine complexes and for P–C bond distances, see: Abbassioun et al. (1990 ▶); Shawkataly et al. (1996 ▶); Hirsivaara et al. (2000 ▶); Barnes et al. (2006 ▶); Bott et al. (2007 ▶); Romeo et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C₂₁H₂₁O₃P
M _r = 352.35
Monoclinic,
a = 29.5721 (4) Å
b = 8.2201 (1) Å
c = 14.9409 (2) Å
β = 96.381 (1)°
V = 3609.42 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 120 K
0.47 × 0.37 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.862, T _max = 0.983
40913 measured reflections
5318 independent reflections
4128 reflections with I > 2σ(I)
R _int = 0.032

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.163
S = 1.05
5318 reflections
413 parameters
189 restraints
H-atom parameters constrained
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.50 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/S1600536809020595/ci2802sup1.cif

e-65-o1525-sup1.cif^{(32.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809020595/ci2802Isup2.hkl

e-65-o1525-Isup2.hkl^{(260.5KB, 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
C21A—H21C⋯Cg1ⁱ	0.96	2.83	3.662 (3)	145

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Symmetry code: (i) Inline graphic . Cg1 is the centroid of the C13A–C18A ring.

Acknowledgments

The authors thank the Malaysian Government and Universiti Sains Malaysia for the Research grant No. 1001/PJJAUH/811115. HKF thanks Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. CSY thanks the Malaysian Government and Universiti Sains Malaysia for the award of the post of Research Officer under the Science Fund grant No. 305/PFIZIK/613312.

supplementary crystallographic information

Comment

The structure determination of the title compound was undertaken as part of a project to study the stereochemistry of substituted triphenylphosphine ligands (Abbassioun et al., 1990; Shawkataly et al., 1996; Hirsivaara et al., 2000; Barnes et al., 2006; Bott et al., 2007). Some of these interesting complexes have been synthesized using this tripodal ligand. Specially, its complex with platinum exhibits fluxionality and has been shown to behave as molecular gears (Romeo et al., 2006). The X-ray crystal structure of its thio analogue namely, tris[2-(methylsulfanyl)phenyl]phosphine, shows two independent molecules (Uttecht et al., 2005).

The whole molecule of title compound is disordered over two positions (Fig. 1 and 2) with refined occupancies of 0.503 (1) and 0.497 (1). The P—C bond lengths and C—P—C angles are comparable to a related structure (Uttecht et al., 2005). Bond lengths (Allen et al., 1987) and angles are within normal ranges. The dihedral angles between the benzene rings C1-C6 (A), C7-C12 (B) and C13-C18 (C) are: A/B 72.9 (2)°, A/C 82.9 (3)° and B/C 70.0 (2)° for the major disorder component, and A/B 85.0 (2)°, A/C 79.2 (2)° and B/C 72.3 (2)° for the minor disorder component.

In the crystal structure, a C18B···C19B(x,1+y,z) contact [3.112 (6) Å], shorter than the sum of the van der Waals radii is observed. The crystal structure (Fig. 3) is stabilized by C—H···π interactions (Table 1).

Experimental

The title compound was supplied by Strem Chemicals. Single crystals of were obtained by slow evaporation of an ethanol solution.