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The title compound, C6H8O4NP·H2O, contains one phosphonate group and one pyridyl ring connected by a CH(OH) group. The pyridyl N atom and one of the three phosphonate O atoms are protonated. Extensive hydrogen-bonding interactions, as well as π–π-stacking interactions, are found between the molecules, thus generating a three-dimensional supramolecular network structure.
Supporting information
CCDC reference: 193734
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.043
- wR factor = 0.103
- Data-to-parameter ratio = 12.1
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXTL (Bruker, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
[Hydroxy(4-pyridyl)methyl]phosphonic acid monohydrate
top
Crystal data top
C6H8NO4P·H2O | F(000) = 432 |
Mr = 207.12 | Dx = 1.671 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 1197 reflections |
a = 6.486 (1) Å | θ = 2.6–23.9° |
b = 15.464 (3) Å | µ = 0.32 mm−1 |
c = 8.457 (2) Å | T = 293 K |
β = 103.91 (1)° | Column, colorless |
V = 823.3 (3) Å3 | 0.30 × 0.25 × 0.10 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD diffractometer | 1613 independent reflections |
Radiation source: fine-focus sealed tube | 1189 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
φ and ω scans | θmax = 26.0°, θmin = 2.6° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1997) | h = −8→7 |
Tmin = 0.906, Tmax = 0.966 | k = 0→19 |
4405 measured reflections | l = 0→10 |
Refinement top
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.103 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0566P)2] where P = (Fo2 + 2Fc2)/3 |
1613 reflections | (Δ/σ)max < 0.001 |
133 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
Special details top
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. The structure was solved by direct methods and successive difference Fourier
syntheses. 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.12248 (10) | 0.76824 (4) | 0.54576 (8) | 0.0230 (2) | |
O1 | 0.3073 (3) | 0.82852 (12) | 0.5804 (2) | 0.0306 (5) | |
O2 | −0.0848 (3) | 0.80124 (12) | 0.4462 (2) | 0.0318 (5) | |
O3 | 0.0825 (3) | 0.73396 (13) | 0.7110 (2) | 0.0325 (5) | |
H3 | 0.183 (5) | 0.727 (2) | 0.780 (4) | 0.045* | |
O4 | 0.0128 (3) | 0.61959 (13) | 0.3815 (2) | 0.0388 (5) | |
H4 | −0.064 (5) | 0.644 (2) | 0.282 (4) | 0.054* | |
O1W | 0.8688 (3) | 0.41828 (14) | 0.9975 (3) | 0.0370 (5) | |
H1WA | 0.772 (5) | 0.377 (2) | 1.008 (4) | 0.052* | |
H1WB | 0.946 (5) | 0.388 (2) | 0.969 (4) | 0.052* | |
N1 | 0.6554 (3) | 0.52927 (15) | 0.7759 (3) | 0.0305 (6) | |
H1N | 0.744 (4) | 0.4937 (18) | 0.851 (4) | 0.043* | |
C1 | 0.4521 (4) | 0.50419 (18) | 0.7443 (3) | 0.0335 (7) | |
H1C | 0.4137 | 0.4564 | 0.7977 | 0.040* | |
C2 | 0.3014 (4) | 0.54843 (17) | 0.6345 (3) | 0.0306 (7) | |
H2C | 0.1604 | 0.5306 | 0.6123 | 0.037* | |
C3 | 0.3576 (4) | 0.61976 (17) | 0.5557 (3) | 0.0230 (6) | |
C4 | 0.5703 (4) | 0.64302 (17) | 0.5909 (3) | 0.0287 (6) | |
H4C | 0.6139 | 0.6902 | 0.5388 | 0.034* | |
C5 | 0.7151 (4) | 0.59667 (18) | 0.7019 (3) | 0.0312 (7) | |
H5C | 0.8575 | 0.6126 | 0.7259 | 0.037* | |
C6 | 0.1915 (4) | 0.67209 (17) | 0.4403 (3) | 0.0261 (6) | |
H6C | 0.2483 | 0.6908 | 0.3485 | 0.031* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0188 (4) | 0.0252 (4) | 0.0222 (4) | 0.0006 (3) | −0.0003 (3) | −0.0001 (3) |
O1 | 0.0259 (10) | 0.0306 (11) | 0.0322 (11) | −0.0063 (8) | 0.0011 (8) | −0.0002 (8) |
O2 | 0.0221 (10) | 0.0379 (11) | 0.0305 (10) | 0.0079 (8) | −0.0033 (8) | −0.0025 (9) |
O3 | 0.0243 (10) | 0.0465 (13) | 0.0242 (10) | −0.0024 (9) | 0.0010 (8) | 0.0045 (9) |
O4 | 0.0337 (12) | 0.0334 (11) | 0.0391 (12) | −0.0068 (9) | −0.0113 (9) | 0.0008 (9) |
O1W | 0.0262 (11) | 0.0358 (13) | 0.0508 (13) | 0.0038 (9) | 0.0125 (10) | 0.0118 (10) |
N1 | 0.0257 (13) | 0.0316 (14) | 0.0295 (12) | 0.0070 (10) | −0.0024 (10) | 0.0000 (11) |
C1 | 0.0366 (17) | 0.0263 (16) | 0.0372 (16) | −0.0001 (13) | 0.0078 (13) | 0.0031 (13) |
C2 | 0.0233 (14) | 0.0294 (16) | 0.0365 (15) | 0.0003 (12) | 0.0021 (12) | 0.0000 (13) |
C3 | 0.0223 (13) | 0.0233 (14) | 0.0223 (13) | 0.0036 (11) | 0.0032 (10) | −0.0053 (11) |
C4 | 0.0252 (14) | 0.0313 (16) | 0.0300 (15) | −0.0011 (12) | 0.0073 (12) | 0.0023 (12) |
C5 | 0.0215 (14) | 0.0357 (17) | 0.0348 (16) | 0.0008 (12) | 0.0040 (12) | −0.0012 (13) |
C6 | 0.0229 (14) | 0.0262 (14) | 0.0267 (14) | −0.0005 (11) | 0.0010 (11) | −0.0006 (11) |
Geometric parameters (Å, º) top
P1—O1 | 1.4910 (18) | N1—H1N | 0.93 (3) |
P1—O2 | 1.4938 (17) | C1—C2 | 1.360 (4) |
P1—O3 | 1.5736 (19) | C1—H1C | 0.9300 |
P1—C6 | 1.843 (3) | C2—C3 | 1.382 (4) |
O3—H3 | 0.77 (3) | C2—H2C | 0.9300 |
O4—C6 | 1.404 (3) | C3—C4 | 1.387 (3) |
O4—H4 | 0.95 (3) | C3—C6 | 1.504 (3) |
O1W—H1WA | 0.92 (3) | C4—C5 | 1.361 (3) |
O1W—H1WB | 0.77 (3) | C4—H4C | 0.9300 |
N1—C5 | 1.321 (3) | C5—H5C | 0.9300 |
N1—C1 | 1.339 (3) | C6—H6C | 0.9800 |
| | | |
O1—P1—O2 | 117.98 (11) | C3—C2—H2C | 120.0 |
O1—P1—O3 | 109.43 (10) | C2—C3—C4 | 117.9 (2) |
O2—P1—O3 | 107.30 (11) | C2—C3—C6 | 120.8 (2) |
O1—P1—C6 | 108.79 (11) | C4—C3—C6 | 121.3 (2) |
O2—P1—C6 | 107.04 (11) | C5—C4—C3 | 119.8 (3) |
O3—P1—C6 | 105.61 (12) | C5—C4—H4C | 120.1 |
P1—O3—H3 | 115 (2) | C3—C4—H4C | 120.1 |
C6—O4—H4 | 107.2 (19) | N1—C5—C4 | 120.7 (2) |
H1WA—O1W—H1WB | 97 (3) | N1—C5—H5C | 119.6 |
C5—N1—C1 | 121.4 (2) | C4—C5—H5C | 119.6 |
C5—N1—H1N | 126.1 (18) | O4—C6—C3 | 108.7 (2) |
C1—N1—H1N | 112.5 (18) | O4—C6—P1 | 111.21 (18) |
N1—C1—C2 | 120.2 (3) | C3—C6—P1 | 109.83 (17) |
N1—C1—H1C | 119.9 | O4—C6—H6C | 109.0 |
C2—C1—H1C | 119.9 | C3—C6—H6C | 109.0 |
C1—C2—C3 | 120.1 (3) | P1—C6—H6C | 109.0 |
C1—C2—H2C | 120.0 | | |
| | | |
C5—N1—C1—C2 | −0.2 (4) | C4—C3—C6—O4 | 158.5 (2) |
N1—C1—C2—C3 | −0.4 (4) | C2—C3—C6—P1 | 98.1 (3) |
C1—C2—C3—C4 | 1.0 (4) | C4—C3—C6—P1 | −79.6 (3) |
C1—C2—C3—C6 | −176.9 (2) | O1—P1—C6—O4 | −170.53 (17) |
C2—C3—C4—C5 | −1.0 (4) | O2—P1—C6—O4 | −42.0 (2) |
C6—C3—C4—C5 | 176.8 (2) | O3—P1—C6—O4 | 72.09 (19) |
C1—N1—C5—C4 | 0.2 (4) | O1—P1—C6—C3 | 69.2 (2) |
C3—C4—C5—N1 | 0.4 (4) | O2—P1—C6—C3 | −162.35 (17) |
C2—C3—C6—O4 | −23.7 (3) | O3—P1—C6—C3 | −48.2 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.77 (3) | 1.85 (3) | 2.617 (2) | 174 (3) |
O4—H4···O1ii | 0.95 (3) | 1.76 (3) | 2.697 (3) | 169 (3) |
O1W—H1WA···O2iii | 0.92 (3) | 1.79 (3) | 2.705 (3) | 173 (3) |
O1W—H1WB···O1iv | 0.77 (3) | 1.97 (3) | 2.727 (3) | 167 (4) |
N1—H1N···O1W | 0.93 (3) | 1.75 (3) | 2.669 (3) | 170 (3) |
Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) x−1/2, −y+3/2, z−1/2; (iii) −x+1/2, y−1/2, −z+3/2; (iv) −x+3/2, y−1/2, −z+3/2. |
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