Ammonium hydrogen (RS)-[(5-methyl-2-oxo-1,3-oxazolidin-3-yl)meth­yl]phospho­nate

Petar Todorov; Emilia Naydenova; Rositsa P Nikolova; Boris L Shivachev

doi:10.1107/S1600536809050338

. 2009 Dec 4;66(Pt 1):o6. doi: 10.1107/S1600536809050338

Ammonium hydrogen (RS)-[(5-methyl-2-oxo-1,3-oxazolidin-3-yl)methyl]phosphonate

Petar Todorov ^a, Emilia Naydenova ^a, Rositsa P Nikolova ^b, Boris L Shivachev ^b,^*

PMCID: PMC2980211 PMID: 21580161

Abstract

In the title compound, NH₄ ⁺·C₅H₉NO₅P⁻, the five-membered methyloxazolidin-2-one unit is disordered over two positions, the major component having a site occupancy of 0.832 (9). A three-dimensional network of O—H⋯O and N—H⋯O hydrogen bonds stabilizes the crystal structure.

Related literature

For general background of the use of phosphonic and aminophosphonic acids as chelating agents in metal extraction and as medicinal compounds, see: Metlushka et al. (2009 ▶); Naydenova et al. (2009 ▶); Matczak-Jon & Videnova-Adrabinska (2005 ▶). For related structures, see: Dudko et al. (200 ▶9); Shivachev et al. (2005 ▶); Todorov et al. (2006 ▶); Ying et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

NH₄ ⁺·C₅H₉NO₅P⁻
M _r = 212.14
Triclinic,
a = 6.471 (3) Å
b = 8.801 (3) Å
c = 9.427 (4) Å
α = 70.76 (2)°
β = 70.658 (18)°
γ = 89.363 (16)°
V = 475.4 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 290 K
0.30 × 0.28 × 0.21 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: none
3673 measured reflections
1855 independent reflections
1606 reflections with I > 2σ(I)
R _int = 0.027
3 standard reflections frequency: 120 min intensity decay: −1%

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.097
S = 1.05
1855 reflections
159 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.33 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: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050338/is2491sup1.cif

e-66-000o6-sup1.cif^{(18.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050338/is2491Isup2.hkl

e-66-000o6-Isup2.hkl^{(89.4KB, 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
N2—HN1⋯O1	0.85	1.94	2.789 (2)	177
O2—H1A⋯O3ⁱ	1.07	1.53	2.5770 (19)	166
N2—HN2⋯O1ⁱⁱ	0.86	1.93	2.772 (2)	165
N2—HN3⋯O3ⁱⁱⁱ	0.89	1.93	2.793 (2)	161
N2—HN4⋯O4^iv	0.97	1.88	2.827 (2)	167

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

Acknowledgments

This work was supported by the University of Chemical Metallurgy and Technology (project 10646).

supplementary crystallographic information

Comment

Phosphonic and aminophosphonic derivatives have a high potential for biological activity. These derivatives have been widely used in the manufacture of herbicides, as chelating agents in metal extraction and as medicinal compounds (Metlushka et al., 2009; Naydenova et al., 2009; Matczak-Jon & Videnova-Adrabinska, 2005). As part of our ongoing studies of the structure-activity relationships for phosphonic acid derivatives (Todorov et al., 2006; Shivachev et al., 2005) herein we report the structure of the titled compound.

The asymmetric unit of the title compound (Fig. 1) contains one molecule, with a proton transferred from the phosphonic group to the ammonia group. The ammonium cation attendant in structure neutralizes the negatively charged phosphonic acid residue. In the crystal structure, the methyloxazolidin-2-one moiety is disordered over two positions. In one of them (major occupancy) the oxazolidine ring (N1/C2/C3/O5/c4) is almost planar [r.m.s. of 0.017 (2) Å] while in the other one it adopts an envelope conformation, with atom C22 deviating within 0.367 (33) Å from the plane defined by the other four atoms [N1/C4/O25/C23 with r.m.s. 0.006 (5) Å]. Bond lengths and angles have normal values and compare well with related structures (Allen et al., 1987; Dudko et al., 2009; Ying et al., 2007; Todorov et al., 2006). The phosphorus atom displays a slightly distorted tetrahedral geometry provided by three oxygen atoms and one carbon atom.

The crystal structure of title compound shows three-dimensional network of O—H···O and N—H···O hydrogen bonds which additionally stabilize the structure (Table 1 and Fig. 2).

Experimental

The title compound, NH₄⁺.C₅H₁₀N₂O₅P^-, was obtained from the reaction of 5-methyloxazolidin-2-one with formaldehyde and phosphorus trichloride in glacial acetic acid. The solution was left at room temperature. Colorless crystals of the title compound were obtained after several days staying.