Diethyl [hydr­oxy(2-nitro­phen­yl)­meth­yl]phospho­nate

Cai-bao Chen; Wei-wei Jin; Xin-yong Li

doi:10.1107/S1600536807063453

. 2007 Dec 6;64(Pt 1):o144. doi: 10.1107/S1600536807063453

Diethyl [hydroxy(2-nitrophenyl)methyl]phosphonate

Cai-bao Chen ^a,^*, Wei-wei Jin ^a, Xin-yong Li ^a

PMCID: PMC2915213 PMID: 21200709

Abstract

In the title molecule, C₁₁H₁₆NO₆P, the nitro group is twisted out of the mean plane of the benzene ring at 29.91 (3)°. The two ethyl groups are disordered between two orientations in the ratios 0.784 (7)/0.216 (7) and 0.733 (6)/0.267 (6). Intermolecular O—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers.

Related literature

For general background, see: Allen et al. (1978 ▶); Hirschmann et al. (1994 ▶).

Experimental

Crystal data

C₁₁H₁₆NO₆P
M _r = 289.22
Triclinic,
a = 7.5659 (13) Å
b = 8.3844 (15) Å
c = 12.557 (2) Å
α = 73.356 (3)°
β = 87.391 (3)°
γ = 64.432 (3)°
V = 685.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 291 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
6168 measured reflections
2800 independent reflections
2381 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.157
S = 1.05
2800 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807063453/cv2361sup1.cif

e-64-0o144-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063453/cv2361Isup2.hkl

e-64-0o144-Isup2.hkl^{(137.4KB, 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
O3—H3A⋯O4ⁱ	0.82 (1)	1.857 (11)	2.671 (3)	174 (4)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank Dr Xiang-Gao Meng for the X-ray data collection.

supplementary crystallographic information

Comment

Phosphonates, especially enantiomerically pure forms, are particularly important in connection with their remarkable biological activities. They have been used as enzyme inhibitors, antibacterial agents, anti-HIV agents, botryticides, and haptens for catalytic antibodies (Allen et al., 1978; Hirschmann et al., 1994). In this regard, the preparation of various optically active phosphonates with a diversity of structures is highly desirable for drug discovery and medicinal chemistry. The title compound (I) was obtained in the reaction of diphenylphosphite with an aromatic aldehyde in the presence of triethylamine.

In (I) (Fig. 1), the nitro group is twisted out of the mean plane of benzene ring at 29.91 (3)°. In the crystal (Fig. 2), intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into centrosymmetric dimers (Fig. 2).

Experimental

To a solution of 2-nitrobenzylaldehyde(1 mmol) in tetrahydrofuran(0.6 ml) was added diphenyl phosphite(1 mmol) at 0°C. After 15 minutes, triethylamine (0.1 ml) was added, and the reaction mixture was stirred for 2 h at 0°C. The resulting solution was washed with saturated NaHCO₃ solution, extracted with dichloromethane and dried over MgSO₄. The solution was filtered and purified by column chroatography on silica gel, using ehtyl acetate and petroleum as eluant to afford the title compound. Crystals of (I) suitable for X-ray data collection were obtained by slow evaporation of a chloroform and methanol solution in ratio of 100:1 at 293 K.