Diethyl (1-hydr­oxy-1-phenyl­ethyl)phospho­nate

M Nawaz Tahir; Nurcan Acar; Hamza Yilmaz; Muhammad Ilyas Tariq; Ghulam Hussain

doi:10.1107/S1600536809011428

. 2009 Mar 31;65(Pt 4):o939. doi: 10.1107/S1600536809011428

Diethyl (1-hydroxy-1-phenylethyl)phosphonate

M Nawaz Tahir ^a,^*, Nurcan Acar ^b, Hamza Yilmaz ^b, Muhammad Ilyas Tariq ^c, Ghulam Hussain ^c

PMCID: PMC2969021 PMID: 21582639

Abstract

The title compound, C₁₂H₁₉O₄P, has a distorted tetrahedral geometry around the P atom. The molecules form dimers with R ₂ ²(10) ring motifs due to intermolecular O—H⋯O hydrogen bonds. The double-bonded O atom of the phosphonate group behaves as an acceptor and the hydroxy group acts as a donor. Both of the ethyl groups are disordered with occupancies of 0.55:0.45 and 0.725:0.275.

Related literature

For phosphonate compounds, see: Acar et al. (2009 ▶); Tahir et al. (2007 ▶, 2009 ▶). For related structures, see: deMendonca et al. (1996 ▶); Feng et al. (2007 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₂H₁₉O₄P
M _r = 258.24
Monoclinic,
a = 20.1187 (12) Å
b = 8.4488 (14) Å
c = 18.4833 (12) Å
β = 116.991 (4)°
V = 2799.6 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 296 K
0.28 × 0.22 × 0.18 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (MolEN; Fair, 1990 ▶) T _min = 0.949, T _max = 0.969
2753 measured reflections
2664 independent reflections
1726 reflections with I > 2σ(I)
R _int = 0.011
3 standard reflections frequency: 120 min intensity decay: −1.2%

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.197
S = 1.02
2664 reflections
162 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1993 ▶); cell refinement: CAD-4 EXPRESS; data reduction: MolEN (Fair, 1990 ▶); program(s) used to solve structure: SHELXS86 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809011428/bq2131sup1.cif

e-65-0o939-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011428/bq2131Isup2.hkl

e-65-0o939-Isup2.hkl^{(128.2KB, hkl)}

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

Table 1. Selected bond lengths (Å).

P1—O2	1.461 (3)
P1—O3	1.555 (3)
P1—O4	1.551 (3)
P1—C7	1.828 (3)
O1—C7	1.420 (4)

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Table 2. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O2ⁱ	0.8200	1.9100	2.709 (4)	163.00

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

In continuation to the study of phosphonate compounds (Acar et al., 2009; Tahir et al., 2007, 2009), we, herein report the preparation and crystal structure of the title compound (I), (Fig. 1.).

The crystal structures of (II) Diethyl 1-hydroxy-1-(pyridin-2-yl)ethyl phosphonate (Feng et al., 2007) and (III) Diethyl (1-hydroxy-1-methyl-3-phenyl- 2-propynyl)phosphonate (deMendonca et al., 1996) has been reported, previously. The title compound (I) has distorted tetrahedral geometry around phosphorus atom (Table 1.) and differs from (II) as pyridin ring has been replaced by the phenyl ring. It is also dimerized (Fig. 2.) forming ring motifs R₂²(10) (Bernstein et al., 1995) due to intermolecular H-bonding of O–H···O type (Table 2.). Both of the ethyl groups are disordered having occupancy ratios of 0.55:0.45 and 0.725:0.275, respectively. There does not exist any kind of π-interaction.