Ethyl [(benzyl­aza­nium­yl)(2-hy­droxy­phen­yl)meth­yl]phospho­nate

Xiangdong Zhang; Rui Zhang; Chunhua Ge; Xiaoyan Zhang

doi:10.1107/S1600536811026444

. 2011 Jul 9;67(Pt 8):o2006. doi: 10.1107/S1600536811026444

Ethyl [(benzylazaniumyl)(2-hydroxyphenyl)methyl]phosphonate

Xiangdong Zhang ^a,^*, Rui Zhang ^a, Chunhua Ge ^a, Xiaoyan Zhang ^a

PMCID: PMC3213461 PMID: 22091040

Abstract

The title compound, C₁₆H₂₀NO₄P, crystallizes as a zwitterion. In the molecule, the two aromatic rings form a dihedral angle of 55.2 (1)°. In the crystal, intermolecular N—H⋯O and O—H⋯O hydrogen bonds link the molecules into columns propagating in [010].

Related literature

For related structures, see: Zhang et al. (2005 ▶, 2007 ▶).

Experimental

Crystal data

C₁₆H₂₀NO₄P
M _r = 321.30
Monoclinic,
a = 28.069 (3) Å
b = 6.0927 (7) Å
c = 22.333 (3) Å
β = 124.464 (2)°
V = 3149.0 (6) Å³
Z = 8
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 296 K
0.28 × 0.25 × 0.19 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.955, T _max = 0.969
8453 measured reflections
3104 independent reflections
1918 reflections with I > 2σ(I)
R _int = 0.057

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.121
S = 1.00
3104 reflections
209 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811026444/cv5124sup1.cif

e-67-o2006-sup1.cif^{(17.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026444/cv5124Isup2.hkl

e-67-o2006-Isup2.hkl^{(152.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811026444/cv5124Isup3.cml

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
N1—H1NA⋯O1ⁱ	0.97 (3)	1.77 (3)	2.738 (3)	179 (2)
N1—H1NB⋯O4	0.86 (3)	2.50 (3)	2.982 (3)	116 (2)
N1—H1NB⋯O2ⁱⁱ	0.86 (3)	2.08 (3)	2.915 (3)	164 (2)
O4—H4A⋯O1	0.82	1.94	2.738 (3)	164
O4—H4A⋯O2ⁱⁱ	0.82	2.58	2.925 (3)	107

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

Acknowledgments

This work was supported by the National Natural Science Foundation of China (No. 20971062/B010303), the Project for Provincial Key Laboratory of Liaoning Province, China (grant No. 2008S104).

supplementary crystallographic information

Comment

As a continuation of our structural study of (2-hydroxyphenyl)methylphosphonate derivatives (Zhang et al., 2005; 2007), we present here the crystal structure of the title compound, (I), which crystallizes as a zwitterion.

In the title molecule (Fig. 1), two aromatic rings form a dihedral angle of 55.2 (1)°. In the crystal structure, intermolecular N—H···O and O—H···O hydrogen bonds (Table 1) link molecules into columns propagated in [010].

Experimental

The title compound was synthesized following the reported method (Zhang et al., 2005). Diethyl phosphonate (0.02 mol) was dissolved in 80 ml of ethanol. The solution was added dropwise to a mixture of salicylaldehyde (0.02 mol) and benzylamine (0.02 mol) in 30 ml e thanol which was refluxed for 4 h. The resulting solution was refluxed until solid appeared. The product was filtered and washed with ethanol. Yield 43%.