Hydrogen 4-ammonio-phenyl-phospho-n-ate.

The title compound, C(6)H(8)NO(3)P, is isostructural with p-arsanilic acid. It exists as the zwitterion H(3)N(+)C(6)H(4)PO(3)H(-). In the crystal, mol-ecules are linked by O-H⋯O and N-H⋯O hydrogen-bond bridges, giving a three-dimensional network structure. The strongest hydrogen bonds are formed between adjacent PO(3)H groups with O⋯O distances of 2.577 (2) Å.

Related literature

For the synthesis of 4-amino­phenyl­phospho­nic acid, see: Cooper et al. (2006 ▶). For the crystal structure of p-arsanilic acid, see: Nuttall & Hunter (1996 ▶). For a description of the TOPOS program, see: Blatov & Proserpio (2009 ▶). For graph-set descriptors of hydrogen bonds, see: Bernstein et al. (1995 ▶). For tables of bond lengths in organic compounds, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C6H8NO3P

M = 173.10

Monoclinic,

a = 7.0967 (13) Å

b = 6.2911 (8) Å

c = 8.4290 (13) Å

β = 100.606 (14)°

V = 369.89 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 200 K

0.28 × 0.19 × 0.06 mm

Data collection

Stoe IPDS 2T diffractometer

2885 measured reflections

1941 independent reflections

1801 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.063

S = 1.08

1941 reflections

116 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.24 e Å−3

Absolute structure: Flack (1983 ▶), 864 Friedel pairs

Flack parameter: 0.13 (8)

Data collection: X-AREA (Stoe & Cie, 2009 ▶); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2009 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2009 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055218/vm2144sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055218/vm2144Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811055218/vm2144Isup3.cml

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

C6H8NO3P	Z = 2
Mr = 173.10	F(000) = 180
Monoclinic, P21	Dx = 1.554 Mg m−3
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 7.0967 (13) Å	µ = 0.33 mm−1
b = 6.2911 (8) Å	T = 200 K
c = 8.4290 (13) Å	Plate, colourless
β = 100.606 (14)°	0.28 × 0.19 × 0.06 mm
V = 369.89 (10) Å3

Stoe IPDS 2T diffractometer	1801 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
graphite	θmax = 29.1°, θmin = 2.5°
Detector resolution: 6.67 pixels mm-1	h = −9→9
rotation method scans	k = −8→8
2885 measured reflections	l = −11→11
1941 independent reflections

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)] = 0.029	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.063	w = 1/[σ2(Fo2) + (0.0348P)2 + 0.0226P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.002
1941 reflections	Δρmax = 0.30 e Å−3
116 parameters	Δρmin = −0.23 e Å−3
4 restraints	Absolute structure: Flack (1983), 864 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.13 (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
P	0.16365 (5)	0.66144 (6)	0.17272 (4)	0.01583 (9)
O2	0.33057 (17)	0.6022 (2)	0.09314 (14)	0.0225 (3)
O1	−0.02778 (17)	0.5711 (2)	0.09090 (14)	0.0214 (3)
O3	0.1487 (2)	0.9089 (2)	0.19018 (14)	0.0243 (3)
H4	0.086 (5)	0.972 (5)	0.091 (4)	0.065 (10)*
N	0.3279 (2)	0.3192 (2)	0.85315 (16)	0.0188 (3)
H1	0.446 (3)	0.256 (4)	0.878 (3)	0.030 (6)*
H2	0.229 (3)	0.226 (3)	0.862 (3)	0.032 (7)*
H3	0.332 (4)	0.417 (4)	0.933 (3)	0.040 (7)*
C4	0.2901 (2)	0.4096 (3)	0.69025 (18)	0.0167 (3)
C6	0.2847 (2)	0.3629 (3)	0.4075 (2)	0.0196 (3)
H6A	0.3068	0.2772	0.3199	0.024*
C1	0.2134 (2)	0.5699 (3)	0.37885 (18)	0.0169 (3)
C5	0.3230 (2)	0.2830 (3)	0.56352 (19)	0.0199 (3)
H5A	0.3713	0.1428	0.5833	0.024*
C3	0.2190 (2)	0.6139 (3)	0.66533 (18)	0.0197 (4)
H3A	0.1967	0.6983	0.7535	0.024*
C2	0.1805 (2)	0.6939 (3)	0.50798 (18)	0.0188 (4)
H2A	0.1316	0.8340	0.4889	0.023*

	U11	U22	U33	U12	U13	U23
P	0.01598 (16)	0.01927 (19)	0.01195 (14)	−0.00100 (19)	0.00178 (11)	−0.00142 (18)
O2	0.0202 (5)	0.0307 (8)	0.0176 (5)	−0.0028 (5)	0.0059 (4)	−0.0041 (4)
O1	0.0173 (6)	0.0266 (7)	0.0190 (5)	−0.0008 (5)	−0.0003 (4)	−0.0048 (5)
O3	0.0343 (7)	0.0199 (7)	0.0169 (6)	−0.0007 (6)	−0.0002 (5)	0.0001 (5)
N	0.0178 (7)	0.0227 (9)	0.0157 (6)	0.0003 (5)	0.0023 (5)	0.0020 (5)
C4	0.0135 (6)	0.0212 (8)	0.0150 (6)	−0.0018 (6)	0.0019 (5)	0.0016 (6)
C6	0.0225 (8)	0.0195 (8)	0.0169 (7)	0.0016 (6)	0.0039 (6)	−0.0029 (6)
C1	0.0150 (7)	0.0214 (8)	0.0138 (7)	−0.0021 (6)	0.0018 (5)	0.0003 (6)
C5	0.0206 (7)	0.0184 (8)	0.0210 (7)	0.0024 (7)	0.0045 (6)	−0.0002 (7)
C3	0.0218 (7)	0.0224 (11)	0.0155 (6)	0.0014 (6)	0.0049 (6)	−0.0022 (6)
C2	0.0209 (7)	0.0174 (10)	0.0180 (7)	0.0018 (6)	0.0033 (5)	−0.0007 (6)

P—O2	1.5114 (13)	C4—C5	1.386 (2)
P—O1	1.5165 (13)	C6—C5	1.387 (2)
P—O3	1.5692 (14)	C6—C1	1.402 (3)
P—C1	1.8026 (16)	C6—H6A	0.9500
O3—H4	0.95 (3)	C1—C2	1.393 (2)
N—C4	1.465 (2)	C5—H5A	0.9500
N—H1	0.918 (17)	C3—C2	1.398 (2)
N—H2	0.928 (17)	C3—H3A	0.9500
N—H3	0.908 (18)	C2—H2A	0.9500
C4—C3	1.383 (2)
O2—P—O1	114.54 (7)	C5—C6—C1	120.08 (16)
O2—P—O3	110.99 (8)	C5—C6—H6A	120.0
O1—P—O3	110.14 (8)	C1—C6—H6A	120.0
O2—P—C1	108.58 (8)	C2—C1—C6	119.51 (15)
O1—P—C1	108.57 (8)	C2—C1—P	122.87 (14)
O3—P—C1	103.37 (8)	C6—C1—P	117.60 (12)
P—O3—H4	111 (2)	C4—C5—C6	119.41 (17)
C4—N—H1	112.4 (15)	C4—C5—H5A	120.3
C4—N—H2	108.1 (15)	C6—C5—H5A	120.3
H1—N—H2	112 (2)	C4—C3—C2	118.74 (15)
C4—N—H3	114.3 (18)	C4—C3—H3A	120.6
H1—N—H3	103 (2)	C2—C3—H3A	120.6
H2—N—H3	107 (2)	C1—C2—C3	120.55 (16)
C3—C4—C5	121.71 (15)	C1—C2—H2A	119.7
C3—C4—N	120.13 (15)	C3—C2—H2A	119.7
C5—C4—N	118.15 (16)
C5—C6—C1—C2	−0.3 (3)	C3—C4—C5—C6	0.3 (2)
C5—C6—C1—P	−179.11 (13)	N—C4—C5—C6	178.67 (16)
O2—P—C1—C2	135.65 (14)	C1—C6—C5—C4	0.0 (3)
O1—P—C1—C2	−99.23 (15)	C5—C4—C3—C2	−0.3 (2)
O3—P—C1—C2	17.73 (16)	N—C4—C3—C2	−178.62 (14)
O2—P—C1—C6	−45.59 (15)	C6—C1—C2—C3	0.3 (2)
O1—P—C1—C6	79.53 (14)	P—C1—C2—C3	179.06 (13)
O3—P—C1—C6	−163.52 (13)	C4—C3—C2—C1	0.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H4···O1i	0.95 (3)	1.64 (3)	2.5772 (17)	166 (3)
N—H1···O2ii	0.92 (2)	1.83 (2)	2.7459 (19)	172 (2)
N—H2···O1iii	0.93 (2)	1.83 (2)	2.751 (2)	170 (2)
N—H3···O2iv	0.91 (2)	1.78 (2)	2.692 (2)	178 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H4⋯O1i	0.95 (3)	1.64 (3)	2.5772 (17)	166 (3)
N—H1⋯O2ii	0.92 (2)	1.83 (2)	2.7459 (19)	172 (2)
N—H2⋯O1iii	0.93 (2)	1.83 (2)	2.751 (2)	170 (2)
N—H3⋯O2iv	0.91 (2)	1.78 (2)	2.692 (2)	178 (3)

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