Ammonium hydrogen (RS)-[(5-methyl-2-oxo-1,3-oxazolidin-3-yl)meth-yl]phospho-nate.

In the title compound, NH(4) (+)·C(5)H(9)NO(5)P(-), the five-membered methyl-oxazolidin-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 = 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

Δρmax = 0.24 e Å−3

Δρmin = −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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

NH4+·C5H9NO5P−	Z = 2
Mr = 212.14	F(000) = 224
Triclinic, P1	Dx = 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 = 0.28 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

Enraf–Nonius CAD-4 diffractometer	Rint = 0.027
Radiation source: fine-focus sealed tube	θmax = 26.0°, θmin = 2.4°
graphite	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 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(Fo2) + (0.0517P)2 + 0.1432P] where P = (Fo2 + 2Fc2)/3
1855 reflections	(Δ/σ)max = 0.001
159 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq	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)

	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)

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)

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···O4iv	0.97	1.88	2.827 (2)	167

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⋯O4iv	0.97	1.88	2.827 (2)	167

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