Dimethyl (1-hydr­oxy-1,2-diphenyl­ethyl)phospho­nate

Nurcan Acar; M Nawaz Tahir; Hamza Yılmaz; Muhammad Saeed Ahmad Chishti; Muhammad Ali Malik

doi:10.1107/S1600536809004036

. 2009 Feb 6;65(Pt 3):o481. doi: 10.1107/S1600536809004036

Dimethyl (1-hydroxy-1,2-diphenylethyl)phosphonate

Nurcan Acar ^a, M Nawaz Tahir ^b,^*, Hamza Yılmaz ^a, Muhammad Saeed Ahmad Chishti ^b, Muhammad Ali Malik ^b

PMCID: PMC2968507 PMID: 21582150

Abstract

In the molecule of the title compound, C₁₆H₁₉O₄P, the coordination around the P atom is distorted tetrahedral. The aromatic rings are oriented at a dihedral angle of 72.28 (11)°. Intramolecular C—H⋯O hydrogen bonding result in the formation of five- and six-membered rings. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link the molecules. There is also a weak C—H⋯π interaction.

Related literature

For related structures, see: Hudson et al. (1993 ▶); Tahir et al. (2007 ▶); Wroblewski et al. (2000 ▶).

Experimental

Crystal data

C₁₆H₁₉O₄P
M _r = 306.28
Monoclinic,
a = 6.0671 (12) Å
b = 17.0962 (11) Å
c = 15.0502 (12) Å
β = 95.0021 (11)°
V = 1555.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.28 × 0.12 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.968, T _max = 0.982
2800 measured reflections
2794 independent reflections
1655 reflections with I > 2σ(I)
R _int = 0.059
3 standard reflections frequency: 120 min intensity decay: −1.3%

Refinement

R[F ² > 2σ(F ²)] = 0.064
wR(F ²) = 0.159
S = 1.01
2794 reflections
191 parameters
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809004036/hk2619sup1.cif

e-65-0o481-sup1.cif^{(21.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004036/hk2619Isup2.hkl

e-65-0o481-Isup2.hkl^{(135.9KB, 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
O1—H1⋯O2ⁱ	0.8200	1.9000	2.710 (3)	172.00
C2—H2⋯O4	0.9300	2.5200	2.956 (4)	109.00
C6—H6⋯O1	0.9300	2.3000	2.671 (4)	103.00
C14—H14⋯O1ⁱⁱ	0.9300	2.5700	3.432 (5)	154.00
C16—H16A⋯O3ⁱⁱ	0.9600	2.4700	3.336 (5)	149.00
C15—H15B⋯CgA	0.9600	2.7200	3.608 (5)	154.00

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Symmetry codes: (i) Inline graphic ; (ii) . CgA is centroid of the C1–C6 ring.

supplementary crystallographic information

Comment

The crystal structure of (R)-dimethyl [(2-chlorophenyl)hydroxymethyl]- phosphonate (Tahir et al., 2007), which is a member of α-hydroxy phosphonates, has been reported, previously. In continuation to the study of such organic compounds, we report herein the synthesis and crystal structure of the title compound, (I).

In the molecule of (I), (Fig. 1) the coordination around the P atom is a distorted tetrahedral. The crystal structure of dimethyl α-chloromethyl-α -hydroxybenzylphosphonate, (II) (Hudson et al., 1993) and C₂₄H₂₆NO₄P, (III) (Wroblewski et al., 2000) have also been reported, in which both of them have similar coordinations around the C-atom having α-hydroxy group. In (I), the benzene rings A (C1-C6) and B (C9-C14) are oriented at a dihedral angle of 72.28 (11)°. The intramolecular C-H···O hydrogen bonds (Table 1) result in the formations of five- and six-membered rings C (O1/C1/C6/C7/H6) and D (P1/O4/C1/C2/C7/H2), respectively, having planar and boat conformations.

In the crystal structure, intermolecular O-H···O and C-H···O hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure. There is also a weak C—H···π interaction (Table 1).

Experimental

For the preparation of the title compound, 2-phenylacetophenone (1.96 g, 10 mmol) was disolved in dimethylphosphonate (1.10 g, 10 mmol) at room temperature. Then, KF (2.5 g) and ψ-Al₂O₃ (2.5 g) were added partwise and the mixture was kept at room temperature for 72 h. The product was extracted twice with 50 ml portions of a dichloromethane/methanol mixture (1:1). After the evaporation of the solvent on a rotary evaporator, the residue was crystallized from a mixture of diethyl ether/acetone (3:1) (m.p. 414 K).