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

Todorov, P.; Naydenova, E.; Nikolova, R.P.; Shivachev, B.L.

doi:10.1107/S1600536809050338

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o6

doi:10.1107/S1600536809050338

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

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

^aUniversity of Chemical Technology and Metallurgy, Department of Organic Chemistry, 8 Kl. Ohridski Boulevard, 1756 Sofia, Bulgaria, and ^bCentral Laboratory of Mineralogy and Crystallography, Bulgarian Academy of Sciences, Acad G. Bonchev Str. build. 107, 1113 Sofia, Bulgaria
^*Correspondence e-mail: blshivachev@gmail.com

(Received 16 November 2009; accepted 23 November 2009; online 4 December 2009)

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, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.035
wR(F²) = 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

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
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x, -y+1, -z+1; (iii) -x+1, -y+1, -z+1; (iv) -x+1, -y+1, -z.

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 ).

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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. (2009); Shivachev et al. (2005); Todorov et al. (2006); Ying et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

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.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); 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).

Figures top

	Fig. 1. The asymmetric unit of title compound with the atom numbering scheme showing 50% probability displacement ellipsoids. H atoms are shown as small spheres of arbitrary radii. Minor occupancy disorder component is represented with dashed lines.
	Fig. 2. A view of the molecular packing in the title compound. All H atoms not involved in the short contact interactions have been omitted for clarity. [Symmetry codes: (i) -x + 1, -y, z + 1; (ii) 1 + x, -y + 1, -z + 1; (iii) -x + 1, -y + 1, -z + 1; (iv) -x + 1, -y + 1, -z.]

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

Crystal data top

NH₄⁺·C₅H₉NO₅P⁻	Z = 2
M_r = 212.14	F(000) = 224
Triclinic, P1	D_x = 1.482 Mg m⁻³
Hall symbol: -P 1	Melting point: not measured K
a = 6.471 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.801 (3) Å	Cell parameters from 22 reflections
c = 9.427 (4) Å	θ = 18.2–19.9°
α = 70.76 (2)°	µ = 0.29 mm⁻¹
β = 70.658 (18)°	T = 290 K
γ = 89.363 (16)°	Prismatic, pale yellow
V = 475.4 (3) Å³	0.30 × 0.28 × 0.21 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.027
Radiation source: fine-focus sealed tube	θ_max = 26.0°, θ_min = 2.4°
Graphite monochromator	h = −7→7
ω/2θ scans	k = −10→10
3673 measured reflections	l = −11→11
1855 independent reflections	3 standard reflections every 120 min
1606 reflections with I > 2σ(I)	intensity decay: −1%

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0517P)² + 0.1432P] where P = (F_o² + 2F_c²)/3
1855 reflections	(Δ/σ)_max = 0.001
159 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

NH₄⁺·C₅H₉NO₅P⁻	γ = 89.363 (16)°
M_r = 212.14	V = 475.4 (3) Å³
Triclinic, P1	Z = 2
a = 6.471 (3) Å	Mo Kα radiation
b = 8.801 (3) Å	µ = 0.29 mm⁻¹
c = 9.427 (4) Å	T = 290 K
α = 70.76 (2)°	0.30 × 0.28 × 0.21 mm
β = 70.658 (18)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.027
3673 measured reflections	3 standard reflections every 120 min
1855 independent reflections	intensity decay: −1%
1606 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.097	H-atom parameters constrained
S = 1.05	Δρ_max = 0.24 e Å⁻³
1855 reflections	Δρ_min = −0.33 e Å⁻³
159 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
P1	0.41857 (7)	0.24449 (5)	0.45738 (5)	0.02797 (16)
O3	0.5389 (2)	0.15751 (15)	0.56719 (15)	0.0337 (3)
O1	0.2459 (2)	0.34533 (16)	0.51681 (16)	0.0398 (3)
O4	0.6905 (3)	0.3598 (2)	−0.03575 (18)	0.0551 (4)
O2	0.3153 (2)	0.12049 (16)	0.40620 (19)	0.0451 (4)
H1A	0.3957	0.0129	0.4192	0.054*
N1	0.7900 (3)	0.3121 (2)	0.18552 (19)	0.0384 (4)
C4	0.8154 (3)	0.3152 (3)	0.0385 (2)	0.0409 (5)
C1	0.6134 (3)	0.3843 (2)	0.2730 (2)	0.0344 (4)
H1B	0.5331	0.4384	0.2035	0.041*
H1C	0.6778	0.4664	0.2985	0.041*
N2	0.2060 (2)	0.66240 (18)	0.34358 (18)	0.0328 (4)
HN2	0.0704	0.6790	0.3837	0.045 (6)*
HN1	0.2222	0.5670	0.3972	0.052 (7)*
HN3	0.3009	0.7318	0.3485	0.056 (7)*
HN4	0.2541	0.6712	0.2322	0.054 (7)*
C2	0.9747 (8)	0.2620 (6)	0.2347 (6)	0.0391 (10)	0.832 (9)
H2A	0.9323	0.1667	0.3309	0.047*	0.832 (9)
H2B	1.0433	0.3480	0.2527	0.047*	0.832 (9)
O5	1.0145 (8)	0.2687 (6)	−0.0269 (6)	0.0502 (9)	0.832 (9)
C5	1.1711 (12)	0.0514 (6)	0.1183 (8)	0.094 (2)	0.832 (9)
H5A	1.2641	0.0400	0.0200	0.141*	0.832 (9)
H5B	1.0342	−0.0159	0.1578	0.141*	0.832 (9)
H5C	1.2432	0.0191	0.1961	0.141*	0.832 (9)
C3	1.1272 (5)	0.2245 (4)	0.0887 (3)	0.0421 (10)	0.832 (9)
H3	1.2677	0.2932	0.0443	0.050*	0.832 (9)
C22	0.988 (5)	0.221 (3)	0.217 (3)	0.039 (5)	0.168 (9)
H22A	1.1119	0.2984	0.1918	0.047*	0.168 (9)
H22B	0.9459	0.1536	0.3292	0.047*	0.168 (9)
O25	0.957 (3)	0.209 (3)	−0.005 (3)	0.043 (4)	0.168 (9)
C25	1.273 (4)	0.128 (3)	0.054 (3)	0.070 (7)	0.168 (9)
H25A	1.3078	0.0833	−0.0305	0.105*	0.168 (9)
H25B	1.3286	0.0648	0.1352	0.105*	0.168 (9)
H25C	1.3404	0.2376	0.0112	0.105*	0.168 (9)
C23	1.047 (3)	0.125 (2)	0.1196 (16)	0.041 (5)	0.168 (9)
H23	0.9758	0.0133	0.1781	0.049*	0.168 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0290 (3)	0.0249 (2)	0.0322 (3)	0.00831 (17)	−0.01321 (19)	−0.01013 (19)
O3	0.0414 (7)	0.0289 (6)	0.0372 (7)	0.0081 (5)	−0.0215 (6)	−0.0115 (6)
O1	0.0367 (7)	0.0324 (7)	0.0418 (8)	0.0125 (6)	−0.0063 (6)	−0.0097 (6)
O4	0.0615 (10)	0.0769 (11)	0.0407 (8)	0.0307 (9)	−0.0294 (8)	−0.0266 (8)
O2	0.0516 (8)	0.0327 (7)	0.0715 (10)	0.0147 (6)	−0.0440 (8)	−0.0214 (7)
N1	0.0343 (8)	0.0544 (10)	0.0328 (8)	0.0181 (8)	−0.0147 (7)	−0.0202 (8)
C4	0.0418 (11)	0.0482 (12)	0.0313 (10)	0.0140 (9)	−0.0122 (9)	−0.0129 (9)
C1	0.0363 (10)	0.0335 (9)	0.0314 (9)	0.0108 (8)	−0.0100 (8)	−0.0107 (8)
N2	0.0338 (9)	0.0310 (8)	0.0338 (8)	0.0066 (6)	−0.0128 (7)	−0.0108 (7)
C2	0.0315 (15)	0.054 (3)	0.0355 (17)	0.0178 (18)	−0.0107 (12)	−0.0209 (18)
O5	0.046 (2)	0.065 (2)	0.0321 (13)	0.0220 (15)	−0.0070 (15)	−0.0147 (17)
C5	0.158 (7)	0.063 (3)	0.130 (5)	0.064 (3)	−0.111 (5)	−0.059 (3)
C3	0.0309 (14)	0.045 (2)	0.0543 (17)	0.0107 (13)	−0.0152 (12)	−0.0220 (14)
C22	0.059 (9)	0.041 (11)	0.044 (8)	0.037 (8)	−0.042 (7)	−0.037 (8)
O25	0.034 (9)	0.067 (12)	0.035 (8)	0.023 (7)	−0.013 (7)	−0.025 (9)
C25	0.066 (14)	0.087 (18)	0.104 (19)	0.049 (11)	−0.050 (13)	−0.073 (16)
C23	0.045 (8)	0.037 (9)	0.043 (7)	0.009 (7)	−0.015 (6)	−0.016 (6)

Geometric parameters (Å, º) top

P1—O1	1.4969 (14)	C2—C3	1.539 (5)
P1—O3	1.5041 (13)	C2—H2A	0.9700
P1—O2	1.5645 (14)	C2—H2B	0.9700
P1—C1	1.816 (2)	O5—C3	1.454 (6)
O4—C4	1.218 (2)	C5—C3	1.497 (6)
O2—H1A	1.0666	C5—H5A	0.9600
N1—C4	1.332 (3)	C5—H5B	0.9600
N1—C2	1.435 (6)	C5—H5C	0.9600
N1—C1	1.447 (2)	C3—H3	0.9800
N1—C22	1.56 (2)	C22—C23	1.41 (2)
C4—O5	1.355 (5)	C22—H22A	0.9700
C4—O25	1.36 (2)	C22—H22B	0.9700
C1—H1B	0.9700	O25—C23	1.46 (3)
C1—H1C	0.9700	C25—C23	1.39 (3)
N2—HN2	0.8645	C25—H25A	0.9600
N2—HN1	0.8517	C25—H25B	0.9600
N2—HN3	0.8934	C25—H25C	0.9600
N2—HN4	0.9676	C23—H23	0.9800

O1—P1—O3	117.20 (8)	H2A—C2—H2B	109.3
O1—P1—O2	109.29 (9)	C4—O5—C3	109.8 (4)
O3—P1—O2	109.68 (8)	C3—C5—H5A	109.5
O1—P1—C1	104.86 (8)	C3—C5—H5B	109.5
O3—P1—C1	109.63 (9)	H5A—C5—H5B	109.5
O2—P1—C1	105.49 (10)	C3—C5—H5C	109.4
P1—O2—H1A	112.0	H5A—C5—H5C	109.5
C4—N1—C2	114.0 (2)	H5B—C5—H5C	109.5
C4—N1—C1	122.16 (16)	O5—C3—C5	108.1 (3)
C2—N1—C1	122.7 (2)	O5—C3—C2	104.9 (3)
C4—N1—C22	101.9 (8)	C5—C3—C2	115.8 (4)
C1—N1—C22	135.9 (8)	O5—C3—H3	109.2
O4—C4—N1	127.90 (19)	C5—C3—H3	109.2
O4—C4—O5	122.2 (3)	C2—C3—H3	109.3
N1—C4—O5	109.8 (3)	C23—C22—N1	108.1 (16)
O4—C4—O25	116.8 (9)	C23—C22—H22A	110.5
N1—C4—O25	111.6 (10)	N1—C22—H22A	110.4
N1—C1—P1	115.39 (13)	C23—C22—H22B	109.8
N1—C1—H1B	108.4	N1—C22—H22B	109.7
P1—C1—H1B	108.4	H22A—C22—H22B	108.3
N1—C1—H1C	108.4	C4—O25—C23	112.2 (16)
P1—C1—H1C	108.4	C23—C25—H25A	109.5
H1B—C1—H1C	107.5	C23—C25—H25B	109.5
HN2—N2—HN1	108.1	H25A—C25—H25B	109.5
HN2—N2—HN3	112.5	C23—C25—H25C	109.4
HN1—N2—HN3	108.1	H25A—C25—H25C	109.5
HN2—N2—HN4	115.2	H25B—C25—H25C	109.5
HN1—N2—HN4	107.4	C25—C23—C22	112 (2)
HN3—N2—HN4	105.2	C25—C23—O25	110.4 (17)
N1—C2—C3	101.4 (3)	C22—C23—O25	100.2 (16)
N1—C2—H2A	111.6	C25—C23—H23	111.1
C3—C2—H2A	111.5	C22—C23—H23	111.5
N1—C2—H2B	111.5	O25—C23—H23	111.2
C3—C2—H2B	111.4

C2—N1—C4—O4	−176.3 (3)	O4—C4—O5—C3	179.2 (2)
C1—N1—C4—O4	−8.3 (4)	N1—C4—O5—C3	2.6 (4)
C22—N1—C4—O4	172.4 (11)	O25—C4—O5—C3	−96 (3)
C2—N1—C4—O5	0.1 (3)	C4—O5—C3—C5	120.3 (5)
C1—N1—C4—O5	168.1 (3)	C4—O5—C3—C2	−3.9 (4)
C22—N1—C4—O5	−11.2 (11)	N1—C2—C3—O5	3.7 (4)
C2—N1—C4—O25	26.4 (9)	N1—C2—C3—C5	−115.5 (5)
C1—N1—C4—O25	−165.6 (9)	C4—N1—C22—C23	−25 (2)
C22—N1—C4—O25	15.1 (13)	C2—N1—C22—C23	−165 (6)
C4—N1—C1—P1	117.3 (2)	C1—N1—C22—C23	156.3 (11)
C2—N1—C1—P1	−75.7 (3)	O4—C4—O25—C23	−161.7 (9)
C22—N1—C1—P1	−63.7 (15)	N1—C4—O25—C23	−1.7 (15)
O1—P1—C1—N1	−175.71 (13)	O5—C4—O25—C23	89 (3)
O3—P1—C1—N1	57.66 (16)	N1—C22—C23—C25	140 (2)
O2—P1—C1—N1	−60.36 (15)	N1—C22—C23—O25	22 (2)
C4—N1—C2—C3	−2.4 (4)	C4—O25—C23—C25	−132 (2)
C1—N1—C2—C3	−170.3 (2)	C4—O25—C23—C22	−14 (2)
C22—N1—C2—C3	41 (4)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	NH₄⁺·C₅H₉NO₅P⁻
M_r	212.14
Crystal system, space group	Triclinic, P1
Temperature (K)	290
a, b, c (Å)	6.471 (3), 8.801 (3), 9.427 (4)
α, β, γ (°)	70.76 (2), 70.658 (18), 89.363 (16)
V (Å³)	475.4 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.30 × 0.28 × 0.21

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3673, 1855, 1606
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.097, 1.05
No. of reflections	1855
No. of parameters	159
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.33

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—HN1···O1	0.85	1.94	2.789 (2)	176.8
O2—H1A···O3ⁱ	1.07	1.53	2.5770 (19)	165.8
N2—HN2···O1ⁱⁱ	0.86	1.93	2.772 (2)	164.5
N2—HN3···O3ⁱⁱⁱ	0.89	1.93	2.793 (2)	161.2
N2—HN4···O4^iv	0.97	1.88	2.827 (2)	166.5

Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y+1, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z.

Acknowledgements

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

References

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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