[Amino-(iminio)meth-yl]phospho-nate.

The title compound, CH(5)N(2)O(3)P, exists as a zwitterion. The N atom of the imino group is protonated and the phospho-nic acid group is deprotonated. The mol-ecular geometry about the central C atom of this zwitterionic species was found to be strictly planar with the sum of the three angles about C being precisely 360°. In the crystal, the mol-ecules are inter-linked by O-H⋯O and N-H⋯O hydrogen-bonding inter-actions, forming a three-dimensional supra-molecular network structure.

Related literature

For background to phospho­nic acid and metal phospho­nate compounds, see: Ayyappan et al. (2001 ▶); Clearfield (1998 ▶); Haga et al. (2007 ▶); Vivani et al. (2008 ▶); Bao et al. (2007 ▶); Cave et al. (2006 ▶); Cao et al. (1992 ▶); Ma et al. (2006 ▶, 2008 ▶). For a related structure, see Makarov et al. (1999 ▶).

Experimental

Crystal data

CH5N2O3P

M = 124.04

Triclinic,

a = 4.8559 (17) Å

b = 5.910 (2) Å

c = 8.101 (3) Å

α = 99.570 (6)°

β = 90.784 (6)°

γ = 101.546 (6)°

V = 224.36 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.50 mm−1

T = 296 K

0.20 × 0.18 × 0.16 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.907, T max = 0.924

1324 measured reflections

855 independent reflections

840 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.161

S = 1.01

855 reflections

64 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.77 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810032083/jj2049sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810032083/jj2049Isup2.hkl

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

CH5N2O3P	Z = 2
Mr = 124.04	F(000) = 128
Triclinic, P1	Dx = 1.836 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.8559 (17) Å	Cell parameters from 1436 reflections
b = 5.910 (2) Å	θ = 2.6–30.3°
c = 8.101 (3) Å	µ = 0.50 mm−1
α = 99.570 (6)°	T = 296 K
β = 90.784 (6)°	Block, colorless
γ = 101.546 (6)°	0.20 × 0.18 × 0.16 mm
V = 224.36 (14) Å3

Bruker SMART APEX CCD diffractometer	855 independent reflections
Radiation source: fine-focus sealed tube	840 reflections with I > 2σ(I)
graphite	Rint = 0.014
phi and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −5→5
Tmin = 0.907, Tmax = 0.924	k = −6→7
1324 measured reflections	l = −9→9

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.161	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.1046P)2 + 0.7669P] where P = (Fo2 + 2Fc2)/3
855 reflections	(Δ/σ)max < 0.001
64 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.77 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
P1	0.66113 (16)	0.60637 (13)	0.74674 (10)	0.0149 (4)
O1	0.3963 (5)	0.6733 (4)	0.8092 (3)	0.0225 (6)
O2	0.7837 (5)	0.6917 (4)	0.5956 (3)	0.0224 (6)
O3	0.8828 (5)	0.6695 (5)	0.9016 (3)	0.0224 (6)
H3B	1.0481	0.6105	0.8696	0.034*
N1	0.7663 (7)	0.1822 (5)	0.6080 (4)	0.0224 (7)
H1A	0.7485	0.0324	0.5929	0.027*
H1B	0.8918	0.2651	0.5566	0.027*
N2	0.4088 (7)	0.1649 (5)	0.7899 (4)	0.0229 (7)
H2A	0.3854	0.0148	0.7776	0.027*
H2B	0.3047	0.2374	0.8554	0.027*
C1	0.6036 (7)	0.2834 (6)	0.7084 (4)	0.0168 (7)

	U11	U22	U33	U12	U13	U23
P1	0.0130 (6)	0.0125 (5)	0.0216 (6)	0.0045 (3)	0.0061 (4)	0.0070 (3)
O1	0.0156 (13)	0.0197 (13)	0.0350 (14)	0.0076 (10)	0.0086 (10)	0.0073 (10)
O2	0.0245 (13)	0.0199 (13)	0.0271 (14)	0.0067 (10)	0.0113 (10)	0.0124 (10)
O3	0.0150 (13)	0.0271 (14)	0.0247 (13)	0.0047 (10)	0.0029 (10)	0.0032 (10)
N1	0.0243 (16)	0.0139 (14)	0.0318 (17)	0.0057 (12)	0.0124 (13)	0.0088 (12)
N2	0.0263 (16)	0.0145 (14)	0.0299 (17)	0.0052 (12)	0.0138 (13)	0.0074 (12)
C1	0.0170 (16)	0.0147 (15)	0.0207 (16)	0.0044 (12)	0.0026 (12)	0.0073 (12)

P1—O2	1.487 (2)	N1—H1A	0.8600
P1—O1	1.490 (3)	N1—H1B	0.8600
P1—O3	1.587 (3)	N2—C1	1.314 (5)
P1—C1	1.845 (3)	N2—H2A	0.8600
O3—H3B	0.9600	N2—H2B	0.8600
N1—C1	1.299 (5)
O2—P1—O1	119.46 (15)	C1—N1—H1B	120.0
O2—P1—O3	111.94 (15)	H1A—N1—H1B	120.0
O1—P1—O3	106.97 (15)	C1—N2—H2A	120.0
O2—P1—C1	108.20 (15)	C1—N2—H2B	120.0
O1—P1—C1	107.89 (15)	H2A—N2—H2B	120.0
O3—P1—C1	100.70 (15)	N1—C1—N2	122.4 (3)
P1—O3—H3B	109.3	N1—C1—P1	118.7 (3)
C1—N1—H1A	120.0	N2—C1—P1	118.8 (3)
O2—P1—C1—N1	28.6 (3)	O2—P1—C1—N2	−154.6 (3)
O1—P1—C1—N1	159.2 (3)	O1—P1—C1—N2	−24.1 (3)
O3—P1—C1—N1	−88.9 (3)	O3—P1—C1—N2	87.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O1i	0.96	1.75	2.611 (4)	147.
N1—H1A···O2ii	0.86	2.06	2.903 (4)	167.
N2—H2A···O1ii	0.86	2.09	2.924 (4)	164.
N1—H1B···O2iii	0.86	2.02	2.812 (4)	153.
N2—H2B···O3iv	0.86	2.21	3.008 (4)	154.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O1i	0.96	1.75	2.611 (4)	147
N1—H1A⋯O2ii	0.86	2.06	2.903 (4)	167
N2—H2A⋯O1ii	0.86	2.09	2.924 (4)	164
N1—H1B⋯O2iii	0.86	2.02	2.812 (4)	153
N2—H2B⋯O3iv	0.86	2.21	3.008 (4)	154

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