(R)-(1-Ammonio-eth-yl)phospho-nate.

The title compound, C(2)H(8)NO(3)P, crystallizes in its zwitterionic form H(3)N(+)CH(CH(3))PO(O(-))(OH). In the crystal, the molecules are linked by N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For the anti­bacterial activity of the title compound, see: Allen et al. (1979 ▶). For the use of the title compound as a co-crystallizing inhibitor on the X-ray structure of the alanine racemase from Bacillus anthracis, a potential anti-anthrax drug target, see: Au et al. (2008 ▶). For examples of coordination compounds of the title compound, see: Cui et al. (2006 ▶); Carraro et al. (2008 ▶). For a description of the graph-set notation for hydrogen-bonded aggregates, see: Grell et al. (1999 ▶). For previous work from our research group on the assembly of coordination polymers using phospho­nic-based mol­ecules, see: Cunha-Silva, Ananias et al. (2009 ▶); Cunha-Silva, Lima et al. (2009 ▶); Shi, Cunha-Silva et al. (2008 ▶); Shi, Trindade et al. (2008 ▶).

Experimental

Crystal data

C2H8NO3P

M = 125.06

Orthorhombic,

a = 4.8256 (1) Å

b = 10.3928 (3) Å

c = 10.4668 (3) Å

V = 524.93 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 150 K

0.12 × 0.08 × 0.04 mm

Data collection

Bruker X8 Kappa CCD APEXII diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1997 ▶) T min = 0.951, T max = 0.983

7972 measured reflections

2535 independent reflections

2362 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.025

wR(F 2) = 0.070

S = 1.07

2535 reflections

77 parameters

7 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.50 e Å−3

Δρmin = −0.26 e Å−3

Absolute structure: Flack (1983 ▶), 1051 Friedel pairs

Flack parameter: 0.00 (8)

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT-Plus (Bruker, 2006 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030308/tk2694sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030308/tk2694Isup2.hkl

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

C2H8NO3P	F(000) = 264
Mr = 125.06	Dx = 1.583 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3869 reflections
a = 4.8256 (1) Å	θ = 2.8–35.9°
b = 10.3928 (3) Å	µ = 0.42 mm−1
c = 10.4668 (3) Å	T = 150 K
V = 524.93 (2) Å3	Prism, colourless
Z = 4	0.12 × 0.08 × 0.04 mm

Bruker X8 Kappa CCD APEXII diffractometer	2535 independent reflections
Radiation source: fine-focus sealed tube	2362 reflections with I > 2σ(I)
graphite	Rint = 0.027
ω and phi scans	θmax = 36.3°, θmin = 3.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −7→8
Tmin = 0.951, Tmax = 0.983	k = −16→17
7972 measured reflections	l = −17→16

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.025	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.070	w = 1/[σ2(Fo2) + (0.0415P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
2535 reflections	Δρmax = 0.50 e Å−3
77 parameters	Δρmin = −0.26 e Å−3
7 restraints	Absolute structure: Flack (1983), 1051 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.00 (8)

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
P1	0.12299 (5)	0.08570 (2)	0.11153 (2)	0.01023 (6)
O1	0.15178 (17)	0.13133 (7)	−0.02404 (7)	0.01436 (13)
O2	0.33072 (15)	−0.02579 (7)	0.14607 (8)	0.01551 (14)
H4	0.512 (2)	0.0009 (18)	0.1437 (15)	0.023*
O3	−0.16015 (15)	0.03922 (8)	0.15035 (8)	0.01671 (15)
N1	0.15332 (19)	0.34471 (8)	0.15951 (8)	0.01264 (14)
H1	0.290 (2)	0.3648 (15)	0.0983 (11)	0.019*
H2	0.152 (3)	0.4080 (12)	0.2239 (10)	0.019*
H3	−0.0211 (19)	0.3439 (15)	0.1171 (13)	0.019*
C1	0.2286 (2)	0.21731 (10)	0.21766 (9)	0.01326 (17)
H1A	0.4352	0.2143	0.2248	0.016*
C2	0.1111 (4)	0.20387 (11)	0.35212 (10)	0.0253 (2)
H2A	0.1924	0.2698	0.4075	0.038*
H2B	0.1557	0.1184	0.3858	0.038*
H2C	−0.0906	0.2148	0.3495	0.038*

	U11	U22	U33	U12	U13	U23
P1	0.00725 (9)	0.01088 (9)	0.01254 (9)	−0.00054 (8)	−0.00037 (8)	0.00118 (8)
O1	0.0141 (3)	0.0168 (3)	0.0121 (3)	−0.0005 (3)	−0.0003 (3)	0.0012 (2)
O2	0.0087 (3)	0.0130 (3)	0.0248 (4)	0.0004 (2)	−0.0024 (2)	0.0025 (3)
O3	0.0076 (3)	0.0195 (3)	0.0229 (3)	−0.0017 (2)	0.0002 (3)	0.0051 (3)
N1	0.0126 (3)	0.0122 (3)	0.0132 (3)	0.0000 (3)	0.0000 (3)	−0.0004 (3)
C1	0.0134 (4)	0.0137 (4)	0.0126 (4)	−0.0001 (3)	−0.0025 (3)	0.0011 (3)
C2	0.0425 (7)	0.0216 (5)	0.0118 (4)	0.0001 (5)	0.0004 (5)	0.0019 (4)

P1—O1	1.5025 (8)	N1—H2	0.942 (7)
P1—O3	1.5051 (8)	N1—H3	0.951 (7)
P1—O2	1.5742 (8)	C1—C2	1.5238 (16)
P1—C1	1.8344 (10)	C1—H1A	1.0000
O2—H4	0.918 (9)	C2—H2A	0.9800
N1—C1	1.5018 (13)	C2—H2B	0.9800
N1—H1	0.943 (8)	C2—H2C	0.9800
O1—P1—O3	116.12 (4)	N1—C1—C2	111.41 (9)
O1—P1—O2	112.98 (4)	N1—C1—P1	110.17 (6)
O3—P1—O2	106.25 (4)	C2—C1—P1	112.80 (8)
O1—P1—C1	108.11 (5)	N1—C1—H1A	107.4
O3—P1—C1	109.15 (5)	C2—C1—H1A	107.4
O2—P1—C1	103.46 (4)	P1—C1—H1A	107.4
P1—O2—H4	112.2 (12)	C1—C2—H2A	109.5
C1—N1—H1	107.5 (10)	C1—C2—H2B	109.5
C1—N1—H2	109.1 (9)	H2A—C2—H2B	109.5
H1—N1—H2	109.6 (9)	C1—C2—H2C	109.5
C1—N1—H3	113.3 (10)	H2A—C2—H2C	109.5
H1—N1—H3	107.7 (9)	H2B—C2—H2C	109.5
H2—N1—H3	109.5 (10)
O1—P1—C1—N1	33.30 (8)	O1—P1—C1—C2	158.48 (8)
O3—P1—C1—N1	−93.86 (7)	O3—P1—C1—C2	31.32 (10)
O2—P1—C1—N1	153.33 (7)	O2—P1—C1—C2	−81.49 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H4···O3i	0.92 (1)	1.63 (1)	2.5484 (10)	175.(2)
N1—H1···O1ii	0.94 (1)	1.91 (1)	2.8033 (11)	157.(1)
N1—H2···O3iii	0.94 (1)	1.90 (1)	2.8369 (12)	178.(1)
N1—H3···O1iv	0.95 (1)	1.87 (1)	2.8160 (12)	171.(1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H4⋯O3i	0.92 (1)	1.63 (1)	2.5484 (10)	175 (2)
N1—H1⋯O1ii	0.94 (1)	1.91 (1)	2.8033 (11)	157 (1)
N1—H2⋯O3iii	0.94 (1)	1.90 (1)	2.8369 (12)	178 (1)
N1—H3⋯O1iv	0.95 (1)	1.87 (1)	2.8160 (12)	171 (1)

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