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The title compound, C7H10FNO7P2, crystallizes in the zwitterionic form. In the crystal structure, mol­ecules are linked via inter­molecular O—H...O hydrogen bonds involv­ing phospho­nate groups, forming a two-dimensional framework. In addition, weak inter­molecular C—H...O hydrogen bonds involving the pyridinium groups further connect mol­ecules, forming a three-dimensional framework.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806004387/lh6584sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806004387/lh6584Isup2.hkl
Contains datablock I

CCDC reference: 601209

Key indicators

  • Single-crystal X-ray study
  • T = 193 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.032
  • wR factor = 0.088
  • Data-to-parameter ratio = 18.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.46 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: XCIF (Bruker, 2001).

[2-(3-Fluoropyridinium-1-yl)–1-hydroxy-1-phosphonoethyl]phosphonate top
Crystal data top
C7H10FNO7P2F(000) = 616
Mr = 301.10Dx = 1.810 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4398 reflections
a = 6.1892 (10) Åθ = 3.1–29.9°
b = 19.1693 (4) ŵ = 0.44 mm1
c = 9.3312 (10) ÅT = 193 K
β = 93.667 (10)°Block, colourless
V = 1104.8 (3) Å30.10 × 0.10 × 0.06 mm
Z = 4
Data collection top
Bruker Kappa-APEXII CCD
diffractometer
3201 independent reflections
Radiation source: fine-focus sealed tube2665 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
profile data from φ and ω scansθmax = 30.0°, θmin = 2.1°
Absorption correction: integration
(SHELXTL/XPREP; Bruker, 2001)
h = 88
Tmin = 0.967, Tmax = 0.981k = 2626
15680 measured reflectionsl = 1313
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.6018P]
where P = (Fo2 + 2Fc2)/3
3201 reflections(Δ/σ)max = 0.002
176 parametersΔρmax = 0.50 e Å3
4 restraintsΔρmin = 0.32 e Å3
Special details top

Experimental. The crystal was mounted using oil (Parantone-N, Exxon) to a 0.3 mm cryo-loop (Hampton Research) with the (0 1 1) scattering planes roughly normal to the spindle axis. One distinct cell was identified using SMART (Bruker, 2001). Four frame series were integrated and filtered for statistical outliers using SAINT (Bruker, 2001) then corrected for absorption by integration using SHELXTL/XPREP (Bruker, 2001) before using SAINT/SADABS (Bruker, 2001) to sort, merge, and scale the combined data. A series of identical frames was collected twice during the experiment to monitor decay. No decay correction was applied.

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. Structure was phased by direct methods. Systematic conditions suggested the unambiguous space group. The space group choice was confirmed by successful convergence of the full-matrix least-squares refinement on F2. The highest peaks in the final difference Fourier map were in the vicinity of atoms O8 and C1; the final map had no other significant features. A final analysis of variance between observed and calculated structure factors showed little dependence on amplitude or resolution.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
P10.41226 (6)0.44840 (2)0.79354 (4)0.01326 (9)
P20.76404 (6)0.553024 (19)0.72862 (4)0.01317 (9)
F11.0442 (3)0.21499 (7)0.91950 (17)0.0600 (4)
O10.39928 (18)0.38731 (6)0.90243 (12)0.0191 (2)
H10.361 (3)0.3987 (11)0.9834 (18)0.029*
O20.31637 (16)0.51504 (6)0.84706 (11)0.0167 (2)
O30.31103 (17)0.42278 (6)0.65129 (11)0.0195 (2)
O40.99640 (17)0.55301 (6)0.67293 (12)0.0171 (2)
H21.095 (3)0.5425 (11)0.735 (2)0.026*
O50.60909 (18)0.57201 (6)0.59910 (12)0.0196 (2)
H30.653 (3)0.5672 (11)0.5133 (18)0.029*
O60.74308 (18)0.59889 (6)0.85500 (11)0.0197 (2)
O70.83747 (17)0.44439 (6)0.90109 (11)0.0162 (2)
H40.792 (3)0.4585 (11)0.9773 (18)0.024*
N10.7718 (2)0.33893 (7)0.69094 (14)0.0173 (2)
C10.7074 (2)0.46110 (7)0.77452 (14)0.0127 (3)
C20.7916 (2)0.41441 (7)0.65544 (15)0.0151 (3)
H50.70800.42420.56360.018*
H60.94530.42570.64280.018*
C30.9182 (3)0.31083 (9)0.78694 (19)0.0252 (3)
H71.03280.33820.82980.030*
C40.8982 (3)0.24148 (10)0.8216 (2)0.0356 (4)
C50.7353 (4)0.20018 (10)0.7608 (3)0.0440 (5)
H80.72360.15240.78590.053*
C60.5903 (3)0.23074 (10)0.6623 (3)0.0414 (5)
H90.47580.20390.61780.050*
C70.6104 (3)0.30032 (9)0.6277 (2)0.0288 (4)
H100.51010.32110.55910.035*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.01074 (16)0.01730 (18)0.01175 (16)0.00011 (13)0.00082 (12)0.00006 (13)
P20.01348 (17)0.01403 (18)0.01206 (17)0.00128 (12)0.00120 (12)0.00141 (13)
F10.0821 (11)0.0305 (7)0.0642 (9)0.0158 (7)0.0195 (8)0.0132 (6)
O10.0232 (5)0.0184 (5)0.0162 (5)0.0008 (4)0.0057 (4)0.0019 (4)
O20.0140 (5)0.0198 (5)0.0163 (5)0.0033 (4)0.0012 (4)0.0005 (4)
O30.0145 (5)0.0300 (6)0.0140 (5)0.0021 (4)0.0002 (4)0.0039 (4)
O40.0129 (5)0.0196 (5)0.0189 (5)0.0002 (4)0.0016 (4)0.0043 (4)
O50.0165 (5)0.0282 (6)0.0139 (5)0.0052 (4)0.0008 (4)0.0050 (4)
O60.0271 (6)0.0167 (5)0.0157 (5)0.0011 (4)0.0045 (4)0.0016 (4)
O70.0149 (5)0.0213 (5)0.0121 (5)0.0035 (4)0.0022 (4)0.0003 (4)
N10.0162 (6)0.0150 (6)0.0210 (6)0.0000 (4)0.0026 (5)0.0043 (5)
C10.0113 (6)0.0149 (6)0.0117 (6)0.0012 (5)0.0004 (5)0.0001 (5)
C20.0143 (6)0.0149 (7)0.0162 (6)0.0003 (5)0.0025 (5)0.0014 (5)
C30.0264 (8)0.0196 (8)0.0292 (8)0.0037 (6)0.0018 (7)0.0019 (6)
C40.0450 (11)0.0216 (9)0.0397 (10)0.0093 (8)0.0001 (9)0.0032 (8)
C50.0521 (13)0.0147 (8)0.0662 (15)0.0018 (8)0.0127 (11)0.0006 (9)
C60.0351 (10)0.0195 (9)0.0692 (15)0.0065 (7)0.0005 (10)0.0108 (9)
C70.0229 (8)0.0220 (8)0.0409 (10)0.0014 (6)0.0012 (7)0.0100 (7)
Geometric parameters (Å, º) top
P1—O21.5071 (11)N1—C31.345 (2)
P1—O31.5130 (11)N1—C71.348 (2)
P1—O11.5559 (11)N1—C21.4911 (19)
P1—C11.8625 (14)C1—C21.5431 (19)
P2—O61.4833 (11)C2—H50.9900
P2—O51.5377 (11)C2—H60.9900
P2—O41.5601 (11)C3—C41.376 (3)
P2—C11.8522 (15)C3—H70.9500
F1—C41.343 (2)C4—C51.376 (3)
O1—H10.834 (15)C5—C61.374 (3)
O4—H20.840 (15)C5—H80.9500
O5—H30.867 (15)C6—C71.380 (3)
O7—C11.4226 (16)C6—H90.9500
O7—H40.827 (15)C7—H100.9500
O2—P1—O3114.59 (6)C2—C1—P1111.78 (9)
O2—P1—O1112.56 (6)P2—C1—P1110.34 (7)
O3—P1—O1107.03 (7)N1—C2—C1111.50 (11)
O2—P1—C1109.28 (6)N1—C2—H5109.3
O3—P1—C1108.21 (6)C1—C2—H5109.3
O1—P1—C1104.63 (6)N1—C2—H6109.3
O6—P2—O5113.75 (7)C1—C2—H6109.3
O6—P2—O4113.22 (6)H5—C2—H6108.0
O5—P2—O4106.27 (6)N1—C3—C4118.46 (16)
O6—P2—C1110.65 (6)N1—C3—H7120.8
O5—P2—C1106.81 (6)C4—C3—H7120.8
O4—P2—C1105.60 (6)F1—C4—C5120.43 (18)
P1—O1—H1115.0 (15)F1—C4—C3117.31 (18)
P2—O4—H2114.5 (14)C5—C4—C3122.26 (19)
P2—O5—H3118.9 (14)C6—C5—C4117.44 (18)
C1—O7—H4115.8 (15)C6—C5—H8121.3
C3—N1—C7121.34 (15)C4—C5—H8121.3
C3—N1—C2118.35 (13)C5—C6—C7120.26 (19)
C7—N1—C2120.30 (14)C5—C6—H9119.9
O7—C1—C2105.55 (11)C7—C6—H9119.9
O7—C1—P2107.50 (9)N1—C7—C6120.24 (18)
C2—C1—P2107.92 (9)N1—C7—H10119.9
O7—C1—P1113.45 (9)C6—C7—H10119.9
O6—P2—C1—O751.22 (11)O1—P1—C1—P2151.56 (7)
O5—P2—C1—O7175.51 (9)C3—N1—C2—C177.51 (16)
O4—P2—C1—O771.65 (10)C7—N1—C2—C1102.50 (16)
O6—P2—C1—C2164.63 (9)O7—C1—C2—N159.80 (14)
O5—P2—C1—C271.08 (10)P2—C1—C2—N1174.51 (9)
O4—P2—C1—C241.76 (10)P1—C1—C2—N163.97 (13)
O6—P2—C1—P172.97 (8)C7—N1—C3—C41.0 (2)
O5—P2—C1—P151.32 (8)C2—N1—C3—C4178.96 (15)
O4—P2—C1—P1164.17 (7)N1—C3—C4—F1178.88 (17)
O2—P1—C1—O789.89 (11)N1—C3—C4—C50.5 (3)
O3—P1—C1—O7144.73 (10)F1—C4—C5—C6179.4 (2)
O1—P1—C1—O730.87 (11)C3—C4—C5—C60.1 (3)
O2—P1—C1—C2150.91 (9)C4—C5—C6—C70.1 (3)
O3—P1—C1—C225.52 (12)C3—N1—C7—C61.0 (3)
O1—P1—C1—C288.34 (10)C2—N1—C7—C6179.02 (17)
O2—P1—C1—P230.81 (9)C5—C6—C7—N10.4 (3)
O3—P1—C1—P294.58 (8)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H3···O3i0.87 (2)1.58 (2)2.4209 (15)163 (2)
O1—H1···O6ii0.83 (2)1.68 (2)2.4950 (15)165 (2)
O4—H2···O2iii0.84 (2)1.75 (2)2.5846 (15)173 (2)
O7—H4···O2ii0.83 (2)1.88 (2)2.7056 (15)177 (2)
C2—H5···O5i0.992.403.3326 (17)156
C2—H6···O3iii0.992.263.2216 (16)163
C3—H7···O1iii0.952.513.430 (2)164
C5—H8···O4iv0.952.593.312 (2)133
C6—H9···O6v0.952.453.260 (2)143
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y+1, z+2; (iii) x+1, y, z; (iv) x+2, y1/2, z+3/2; (v) x+1, y1/2, z+3/2.
 

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