Hydroxonium 1-ammonio-ethyl-idene-1,1-bis-phospho-nate.

The title compound, H(3)O(+)·C(2)H(8)NO(6)P(2) (-), contains a disordered H(3)O(+) cation and an NH(3)C(CH(3))(PO(3)H)(2) anion. The three H atoms of the H(3)O(+) cation are statistically distributed over four positions with occupancies of 0.75, resulting in a pseudo tetra-hedron. Multiple N-H⋯O and O-H⋯O hydrogen bonds generate an intricate three-dimensional network.

Related literature

For related literature, see: Bollinger & Roundhill (1993 ▶); Chai et al. (1980 ▶); Clearfield (2002 ▶); Fernández et al. (2003 ▶); Li et al. (2008 ▶); Finn et al. (2003 ▶); Yin et al. (2005 ▶).

Experimental

Crystal data

H3O+·C2H8NO6P2 −

M = 223.06

Triclinic,

a = 5.6379 (5) Å

b = 8.9712 (8) Å

c = 9.2302 (8) Å

α = 102.111 (1)°

β = 100.499 (1)°

γ = 101.342 (1)°

V = 435.22 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.50 mm−1

T = 293 (2) K

0.36 × 0.32 × 0.27 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.839, T max = 0.876

2811 measured reflections

1946 independent reflections

1871 reflections with I > 2σ(I)

R int = 0.009

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.095

S = 1.08

1946 reflections

113 parameters

H-atom parameters constrained

Δρmax = 0.44 e Å−3

Δρmin = −0.58 e Å−3

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; 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 PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808029565/pv2098sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029565/pv2098Isup2.hkl

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

H3O+·C2H8NO6P2−	Z = 2
Mr = 223.06	F(000) = 232
Triclinic, P1	Dx = 1.702 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6379 (5) Å	Cell parameters from 2523 reflections
b = 8.9712 (8) Å	θ = 2.4–29.6°
c = 9.2302 (8) Å	µ = 0.50 mm−1
α = 102.111 (1)°	T = 293 K
β = 100.499 (1)°	Plate, colorless
γ = 101.342 (1)°	0.36 × 0.32 × 0.27 mm
V = 435.22 (7) Å3

Bruker SMART 4K CCD area-detector diffractometer	1871 reflections with I > 2σ(I)
graphite	Rint = 0.009
φ and ω scans	θmax = 27.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.839, Tmax = 0.876	k = −9→11
2811 measured reflections	l = −11→8
1946 independent reflections

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) = 0.095	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0451P)2 + 0.5124P] where P = (Fo2 + 2Fc2)/3
1946 reflections	(Δ/σ)max < 0.001
113 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

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

	x	y	z	Uiso*/Ueq	Occ. (<1)
P1	0.64618 (8)	0.73089 (5)	0.49332 (5)	0.01519 (14)
P2	0.58222 (8)	0.83546 (6)	0.19085 (5)	0.01897 (14)
C1	0.7352 (3)	0.7236 (2)	0.3101 (2)	0.0159 (3)
C2	0.6859 (4)	0.5520 (2)	0.2183 (2)	0.0263 (4)
H2A	0.7448	0.5493	0.1268	0.039*
H2B	0.5106	0.5046	0.1924	0.039*
H2C	0.7717	0.4950	0.2784	0.039*
N1	1.0110 (3)	0.79403 (19)	0.34632 (18)	0.0177 (3)
H1A	1.0884	0.7500	0.4126	0.027*
H1B	1.0421	0.8971	0.3866	0.027*
H1C	1.0657	0.7766	0.2612	0.027*
O1	0.8136 (2)	0.63586 (16)	0.57120 (16)	0.0207 (3)
H1	0.7371	0.5435	0.5513	0.031*
O2	0.7185 (3)	0.89740 (16)	0.58704 (16)	0.0234 (3)
O3	0.3743 (2)	0.64928 (16)	0.46080 (17)	0.0218 (3)
O4	0.6364 (3)	1.00594 (17)	0.29828 (18)	0.0267 (3)
H4	0.5123	1.0175	0.3295	0.040*
O5	0.7259 (3)	0.8501 (2)	0.07158 (17)	0.0295 (3)
O6	0.3106 (3)	0.75734 (19)	0.14090 (16)	0.0262 (3)
O1W	1.0469 (3)	0.8192 (2)	−0.1160 (2)	0.0403 (4)
H9	1.0002	0.7549	−0.2088	0.061*	0.75
H10	0.9220	0.8286	−0.0718	0.061*	0.75
H11	1.1434	0.7837	−0.0515	0.061*	0.75
H12	1.1157	0.9206	−0.1025	0.061*	0.75

	U11	U22	U33	U12	U13	U23
P1	0.0131 (2)	0.0149 (2)	0.0193 (2)	0.00319 (17)	0.00587 (17)	0.00642 (17)
P2	0.0151 (2)	0.0268 (3)	0.0203 (3)	0.00901 (19)	0.00713 (18)	0.01124 (19)
C1	0.0124 (7)	0.0172 (8)	0.0194 (8)	0.0038 (6)	0.0051 (6)	0.0057 (6)
C2	0.0297 (10)	0.0204 (9)	0.0257 (10)	0.0056 (8)	0.0055 (8)	0.0005 (7)
N1	0.0128 (7)	0.0209 (7)	0.0223 (8)	0.0054 (6)	0.0068 (6)	0.0083 (6)
O1	0.0173 (6)	0.0195 (6)	0.0253 (7)	0.0040 (5)	0.0017 (5)	0.0094 (5)
O2	0.0265 (7)	0.0170 (7)	0.0275 (7)	0.0043 (5)	0.0119 (6)	0.0033 (5)
O3	0.0132 (6)	0.0226 (7)	0.0334 (8)	0.0043 (5)	0.0073 (5)	0.0138 (6)
O4	0.0239 (7)	0.0241 (7)	0.0376 (8)	0.0104 (6)	0.0125 (6)	0.0106 (6)
O5	0.0297 (8)	0.0425 (9)	0.0283 (8)	0.0162 (7)	0.0175 (6)	0.0184 (7)
O6	0.0162 (7)	0.0401 (8)	0.0239 (7)	0.0087 (6)	0.0033 (5)	0.0112 (6)
O1W	0.0390 (9)	0.0496 (11)	0.0344 (9)	0.0119 (8)	0.0101 (7)	0.0127 (8)

P1—O2	1.4952 (14)	C2—H2B	0.9600
P1—O3	1.5081 (13)	C2—H2C	0.9600
P1—O1	1.5686 (14)	N1—H1A	0.8900
P1—C1	1.8417 (18)	N1—H1B	0.8900
P2—O5	1.4928 (14)	N1—H1C	0.8900
P2—O6	1.4947 (14)	O1—H1	0.8200
P2—O4	1.5765 (15)	O4—H4	0.8200
P2—C1	1.8497 (19)	O1W—H9	0.8869
C1—N1	1.505 (2)	O1W—H10	0.8852
C1—C2	1.537 (2)	O1W—H11	0.8841
C2—H2A	0.9600	O1W—H12	0.8888
O2—P1—O3	115.72 (8)	C1—C2—H2B	109.5
O2—P1—O1	108.61 (8)	H2A—C2—H2B	109.5
O3—P1—O1	111.06 (8)	C1—C2—H2C	109.5
O2—P1—C1	109.30 (8)	H2A—C2—H2C	109.5
O3—P1—C1	108.25 (8)	H2B—C2—H2C	109.5
O1—P1—C1	103.15 (8)	C1—N1—H1A	109.5
O5—P2—O6	118.42 (9)	C1—N1—H1B	109.5
O5—P2—O4	106.13 (9)	H1A—N1—H1B	109.5
O6—P2—O4	112.40 (8)	C1—N1—H1C	109.5
O5—P2—C1	105.96 (8)	H1A—N1—H1C	109.5
O6—P2—C1	108.21 (8)	H1B—N1—H1C	109.5
O4—P2—C1	104.72 (8)	P1—O1—H1	109.5
N1—C1—C2	107.76 (14)	P2—O4—H4	109.5
N1—C1—P1	106.97 (11)	H9—O1W—H10	113.6
C2—C1—P1	110.19 (13)	H9—O1W—H11	112.2
N1—C1—P2	107.45 (12)	H10—O1W—H11	102.3
C2—C1—P2	109.40 (13)	H9—O1W—H12	120.3
P1—C1—P2	114.79 (9)	H10—O1W—H12	98.6
C1—C2—H2A	109.5	H11—O1W—H12	107.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3i	0.89	2.02	2.798 (2)	145
N1—H1B···O2ii	0.89	2.00	2.766 (2)	144
N1—H1C···O6i	0.89	1.93	2.771 (2)	156
O1—H1···O3iii	0.82	1.69	2.501 (2)	168
O4—H4···O2iv	0.82	1.84	2.635 (2)	164
O1W—H9···O1v	0.89	2.06	2.923 (2)	164
O1W—H10···O5	0.89	1.88	2.737 (2)	164
O1W—H11···O6i	0.88	1.94	2.781 (2)	159
O1W—H12···O5vi	0.89	2.01	2.901 (3)	180

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3i	0.89	2.02	2.798 (2)	145
N1—H1B⋯O2ii	0.89	2.00	2.766 (2)	144
N1—H1C⋯O6i	0.89	1.93	2.771 (2)	156
O1—H1⋯O3iii	0.82	1.69	2.501 (2)	168
O4—H4⋯O2iv	0.82	1.84	2.635 (2)	164
O1W—H9⋯O1v	0.89	2.06	2.923 (2)	164
O1W—H10⋯O5	0.89	1.88	2.737 (2)	164
O1W—H11⋯O6i	0.88	1.94	2.781 (2)	159
O1W—H12⋯O5vi	0.89	2.01	2.901 (3)	180

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