4-[2-(Hydrogen phosphonato)-2-hydroxy-2-phosphonoethyl]pyridinium.

The title compound, C(7)H(11)NO(7)P(2), exists as a zwitterion in which the positive charge resides on the protonated pyridyl N atom and the negative charge on one of the two phosphate groups. In the crystal, adjacent molcules are linked by O-H⋯O and N-H⋯O hydrogen bonds into a three-dimensional network.

Related literature

For metal complexes of phospho­nic acids, see: Ma et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C7H11NO7P2

M = 283.11

Monoclinic,

a = 10.083 (2) Å

b = 9.4713 (19) Å

c = 11.708 (2) Å

β = 94.87 (3)°

V = 1114.1 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.42 mm−1

T = 293 K

0.3 × 0.25 × 0.2 mm

Data collection

Rigaku Mercury diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) ▶ T min = 0.880, T max = 0.92

11137 measured reflections

2548 independent reflections

2093 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.117

S = 1.02

2548 reflections

174 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005) ▶; cell refinement: CrystalClear ▶; data reduction: CrystalClear ▶; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: PLATON (Spek, 2009) ▶.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811011408/ng5136sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811011408/ng5136Isup2.hkl

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

C7H11NO7P2	F(000) = 584
Mr = 283.11	Dx = 1.688 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10067 reflections
a = 10.083 (2) Å	θ = 3.4–27.6°
b = 9.4713 (19) Å	µ = 0.42 mm−1
c = 11.708 (2) Å	T = 293 K
β = 94.87 (3)°	Block, colorless
V = 1114.1 (4) Å3	0.3 × 0.25 × 0.2 mm
Z = 4

Rigaku Mercury diffractometer	2548 independent reflections
Radiation source: fine-focus sealed tube	2093 reflections with I > 2σ(I)
graphite	Rint = 0.051
Detector resolution: 13.6612 pixels mm-1	θmax = 27.5°, θmin = 3.3°
dtfind.ref scans	h = −13→13
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −12→12
Tmin = 0.880, Tmax = 0.92	l = −15→15
11137 measured 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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0537P)2 + 1.150P] where P = (Fo2 + 2Fc2)/3
2548 reflections	(Δ/σ)max < 0.001
174 parameters	Δρmax = 0.30 e Å−3
5 restraints	Δρmin = −0.29 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.

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 > 2sigma(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	0.66199 (6)	0.19546 (7)	0.09909 (6)	0.01961 (18)
P2	0.87076 (6)	0.20407 (7)	0.30954 (6)	0.01825 (18)
O1	0.88791 (18)	0.0416 (2)	0.12393 (16)	0.0229 (4)
H1A	0.846 (3)	−0.021 (3)	0.151 (3)	0.041 (10)*
O2	0.81307 (19)	0.3435 (2)	0.34177 (16)	0.0277 (4)
O3	1.01876 (18)	0.1862 (2)	0.33689 (16)	0.0275 (5)
O4	0.79155 (19)	0.0847 (2)	0.36597 (16)	0.0258 (4)
H4A	0.827 (4)	0.008 (3)	0.370 (3)	0.059 (12)*
O5	0.58172 (19)	0.0799 (2)	0.1556 (2)	0.0327 (5)
H5A	0.613 (4)	0.000 (2)	0.157 (3)	0.069 (14)*
O6	0.6632 (2)	0.1660 (2)	−0.02975 (18)	0.0341 (5)
H6A	0.619 (4)	0.218 (4)	−0.072 (3)	0.059 (13)*
O7	0.60449 (17)	0.33631 (19)	0.12698 (17)	0.0269 (5)
N1	1.3345 (2)	0.3264 (3)	0.1400 (2)	0.0362 (6)
H2A	1.4152 (19)	0.334 (4)	0.143 (3)	0.058 (12)*
C2	1.2820 (3)	0.2028 (3)	0.1039 (3)	0.0331 (7)
H2	1.3374	0.1275	0.0894	0.040*
C3	1.1465 (3)	0.1875 (3)	0.0883 (2)	0.0279 (6)
H3	1.1097	0.1020	0.0625	0.033*
C4	1.0641 (3)	0.2998 (3)	0.1109 (2)	0.0221 (6)
C5	1.1232 (3)	0.4260 (3)	0.1492 (3)	0.0334 (7)
H5	1.0705	0.5024	0.1662	0.040*
C6	1.2600 (3)	0.4372 (4)	0.1618 (3)	0.0413 (8)
H6	1.2999	0.5220	0.1855	0.050*
C7	0.9147 (2)	0.2907 (3)	0.0868 (2)	0.0234 (6)
H7A	0.8954	0.2725	0.0055	0.028*
H7B	0.8777	0.3826	0.1023	0.028*
C8	0.8396 (2)	0.1788 (2)	0.1534 (2)	0.0166 (5)

	U11	U22	U33	U12	U13	U23
P1	0.0118 (3)	0.0169 (3)	0.0293 (4)	0.0002 (3)	−0.0028 (2)	−0.0001 (3)
P2	0.0170 (3)	0.0162 (3)	0.0213 (3)	0.0004 (3)	−0.0001 (2)	−0.0024 (3)
O1	0.0193 (9)	0.0172 (10)	0.0326 (10)	0.0020 (8)	0.0050 (8)	−0.0043 (8)
O2	0.0302 (10)	0.0183 (10)	0.0349 (11)	0.0020 (8)	0.0048 (8)	−0.0068 (8)
O3	0.0193 (10)	0.0355 (11)	0.0265 (10)	0.0036 (8)	−0.0060 (7)	−0.0050 (9)
O4	0.0287 (11)	0.0186 (10)	0.0310 (10)	0.0019 (8)	0.0082 (8)	0.0040 (8)
O5	0.0167 (10)	0.0234 (12)	0.0577 (14)	−0.0027 (8)	0.0011 (9)	0.0076 (10)
O6	0.0316 (11)	0.0390 (13)	0.0294 (11)	0.0093 (10)	−0.0116 (9)	−0.0025 (10)
O7	0.0161 (9)	0.0177 (10)	0.0466 (12)	0.0012 (8)	0.0018 (8)	−0.0016 (8)
N1	0.0154 (12)	0.0549 (18)	0.0386 (15)	−0.0072 (12)	0.0046 (10)	−0.0016 (13)
C2	0.0199 (14)	0.0435 (19)	0.0368 (16)	0.0047 (13)	0.0074 (12)	0.0006 (14)
C3	0.0225 (14)	0.0300 (16)	0.0319 (15)	−0.0022 (12)	0.0060 (11)	−0.0039 (12)
C4	0.0180 (13)	0.0260 (14)	0.0229 (13)	−0.0027 (11)	0.0051 (10)	0.0022 (11)
C5	0.0240 (15)	0.0265 (16)	0.0507 (19)	−0.0058 (12)	0.0094 (13)	−0.0057 (14)
C6	0.0262 (16)	0.043 (2)	0.055 (2)	−0.0144 (15)	0.0074 (14)	−0.0112 (16)
C7	0.0144 (12)	0.0248 (14)	0.0311 (14)	−0.0015 (11)	0.0021 (10)	0.0059 (12)
C8	0.0129 (11)	0.0129 (12)	0.0236 (12)	0.0017 (9)	−0.0004 (9)	−0.0007 (10)

P1—O7	1.5015 (19)	N1—C2	1.339 (4)
P1—O6	1.535 (2)	N1—H2A	0.815 (19)
P1—O5	1.543 (2)	C2—C3	1.371 (4)
P1—C8	1.855 (2)	C2—H2	0.9300
P2—O2	1.5038 (19)	C3—C4	1.388 (4)
P2—O3	1.5090 (19)	C3—H3	0.9300
P2—O4	1.563 (2)	C4—C5	1.392 (4)
P2—C8	1.844 (3)	C4—C7	1.512 (3)
O1—C8	1.440 (3)	C5—C6	1.379 (4)
O1—H1A	0.806 (18)	C5—H5	0.9300
O4—H4A	0.811 (18)	C6—H6	0.9300
O5—H5A	0.821 (19)	C7—C8	1.551 (3)
O6—H6A	0.81 (4)	C7—H7A	0.9700
N1—C6	1.328 (4)	C7—H7B	0.9700
O7—P1—O6	114.23 (12)	C2—C3—H3	120.0
O7—P1—O5	108.10 (12)	C4—C3—H3	120.0
O6—P1—O5	109.93 (13)	C3—C4—C5	118.2 (2)
O7—P1—C8	112.34 (11)	C3—C4—C7	121.6 (2)
O6—P1—C8	103.49 (12)	C5—C4—C7	120.1 (2)
O5—P1—C8	108.59 (11)	C6—C5—C4	119.8 (3)
O2—P2—O3	116.23 (11)	C6—C5—H5	120.1
O2—P2—O4	107.85 (11)	C4—C5—H5	120.1
O3—P2—O4	111.15 (11)	N1—C6—C5	119.7 (3)
O2—P2—C8	108.99 (11)	N1—C6—H6	120.2
O3—P2—C8	106.16 (11)	C5—C6—H6	120.2
O4—P2—C8	105.97 (11)	C4—C7—C8	117.8 (2)
C8—O1—H1A	112 (2)	C4—C7—H7A	107.9
P2—O4—H4A	116 (3)	C8—C7—H7A	107.9
P1—O5—H5A	117 (3)	C4—C7—H7B	107.9
P1—O6—H6A	117 (3)	C8—C7—H7B	107.9
C6—N1—C2	122.5 (3)	H7A—C7—H7B	107.2
C6—N1—H2A	120 (3)	O1—C8—C7	107.8 (2)
C2—N1—H2A	117 (3)	O1—C8—P2	108.77 (16)
N1—C2—C3	119.8 (3)	C7—C8—P2	111.14 (17)
N1—C2—H2	120.1	O1—C8—P1	109.33 (16)
C3—C2—H2	120.1	C7—C8—P1	105.54 (16)
C2—C3—C4	119.9 (3)	P2—C8—P1	114.04 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.81 (2)	2.06 (2)	2.816 (3)	156 (3)
O4—H4A···O7i	0.81 (2)	1.77 (2)	2.574 (3)	176 (4)
O5—H5A···O2i	0.82 (2)	1.66 (2)	2.477 (3)	175 (4)
N1—H2A···O7ii	0.82 (2)	1.93 (2)	2.741 (3)	171 (4)
O6—H6A···O3iii	0.81 (4)	1.67 (4)	2.476 (3)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.81 (2)	2.06 (2)	2.816 (3)	156 (3)
O4—H4A⋯O7i	0.81 (2)	1.77 (2)	2.574 (3)	176 (4)
O5—H5A⋯O2i	0.82 (2)	1.66 (2)	2.477 (3)	175 (4)
N1—H2A⋯O7ii	0.82 (2)	1.93 (2)	2.741 (3)	171 (4)
O6—H6A⋯O3iii	0.81 (4)	1.67 (4)	2.476 (3)	175 (4)

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