(2-Chloro­phen­yl)(diphenyl­phosphor­yl)methanol

Wan-Yun Liu; Ping Huo

doi:10.1107/S1600536807057674

. 2007 Dec 12;64(Pt 1):o233. doi: 10.1107/S1600536807057674

(2-Chlorophenyl)(diphenylphosphoryl)methanol

Wan-Yun Liu ^a,^*, Ping Huo ^a

PMCID: PMC2915293 PMID: 21200800

Abstract

The title compound, C₁₉H₁₆ClO₂P, was obtained by the reaction of diphenylphosphine oxide with 2-chlorobenzaldehyde. The molecule has a tetrahedral structure at the P atom. The dihedral angle between the phenyl rings attached to the P atom is 80.4 (1)°. The molecules are linked together by intermolecular O—H⋯O and C—H⋯O hydrogen-bonding interactrions. The crystal studied was an inversion twin.

Related literature

For general background, see: Clark et al. (2002 ▶). For related structures, see: Dankowski et al. (1979 ▶); Liu et al. (2007 ▶).

Experimental

Crystal data

C₁₉H₁₆ClO₂P
M _r = 342.74
Orthorhombic,
a = 9.0943 (4) Å
b = 10.9172 (6) Å
c = 18.0657 (12) Å
V = 1793.64 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 293 (2) K
0.57 × 0.20 × 0.10 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; (Bruker, 2001 ▶) T _min = 0.844, T _max = 0.970
8361 measured reflections
3466 independent reflections
2494 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.084
S = 0.91
3466 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.26 e Å⁻³
Absolute structure: Flack (1983 ▶), 1437 Friedel pairs
Flack parameter: 0.55 (8)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807057674/xu2343sup1.cif

e-64-0o233-sup1.cif^{(18.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807057674/xu2343Isup2.hkl

e-64-0o233-Isup2.hkl^{(170KB, 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
O2—H2A⋯O1ⁱ	0.82	1.82	2.602 (2)	158
C1—H3A⋯O1ⁱ	0.98	2.56	3.059 (2)	111
C16—H33A⋯O2ⁱⁱ	0.93	2.56	3.318 (3)	139

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

Acknowledgments

The authors thank the Technical Project of the Department of Education of Jiangxi Province, China, and the Key Technical Project of Yichun Municipality, China, for supporting this work.

supplementary crystallographic information

Comment

The title compound is an analog of (diphenylphosphinoyl)phenylmethanol, which was employed as a ligand in the rhodiumcatalyzed hydroformylation of alkenes, with good conversions and regioselectivities (Clark et al., 2002).

The molecular structure is shown in Fig. 1. Bond lengths and angles are in agreement with those reported for similar compounds (Dankowski et al., 1979; Liu et al., 2007). The dihedral angle between the C8-phenyl and C14-phenyl planes is 80.4 (1)°. The O—H···O and C—H···O hydrogen bonds (Table 1) involving the hydroxyl group link the molecules into a supra-molecular structure.

Experimental

To a solution of 2-chlorobenzaldehyde (0.28 g, 2.0 mmol) and diphenylphosphine oxide (0.41 g, 2.0 mmol) in tetrahydrofuran (10 ml) at 273 K was added dropwise triethylamine (0.30 ml, 2.0 mmol). The cooling bath was removed and the mixture warmed to ambient temperature for 2 h. The solvent was concentrated under vacuum and the crude product was purified by column chromatography (petroleum ether-ethyl acetate, 1:1) to give the title compound as a white solid in 85% yield. Single crystals were obtained by slow evaporation of a methanol solution.