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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1607.
Published online 2008 July 26. doi:  10.1107/S1600536808023143
PMCID: PMC2962219

Ammonium benzene­phospho­nate

Abstract

In the crystal structure of the title salt, NH4 +.[(C6H5)P(O)2(OH)] or NH4 +·C6H6O3P, the N and O atoms inter­act via hydrogen bonds to generate a layer motif. The phenyl rings are stacked above and below this layer, sandwiching the hydrogen-bonded layer.

Related literature

For the crystal structure of benzene­phospho­nic acid, see: Weakley (1976 [triangle]); Mahmoudkhani & Langer (2002 [triangle]). For the crystal structure of the 1:1 co-crystal of ammonium benzene­phospho­nate and benzene­phospho­nic acid, see: Rao & Vidyasagar (2005 [triangle]).

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Object name is e-64-o1607-scheme1.jpg

Experimental

Crystal data

  • NH4 +·C6H6O3P
  • M r = 175.12
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1607-efi1.jpg
  • a = 31.122 (2) Å
  • b = 7.1249 (5) Å
  • c = 7.9441 (5) Å
  • V = 1761.5 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.27 mm−1
  • T = 293 (2) K
  • 0.4 × 0.4 × 0.2 mm

Data collection

  • Bruker SMART 1000 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.807, T max = 0.947
  • 7880 measured reflections
  • 1565 independent reflections
  • 1540 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.066
  • wR(F 2) = 0.173
  • S = 1.27
  • 1565 reflections
  • 120 parameters
  • 11 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.31 e Å−3
  • Δρmin = −0.39 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023143/xu2441sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023143/xu2441Isup2.hkl

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

Acknowledgments

This work was sponsored by the Natural Science Foundation of Shanxi Province (grant No. 2008011024) and the University of Malaya.

supplementary crystallographic information

Comment

The title compound (Scheme I, Fig. 1) is a side-product in the synthesis of 2-methylphenylamidinium phenylphosphinate.

Experimental

m-Tolunitrile (0.6 ml, 5 mmol) and lithium bis(trimethylsilyl)amide (0.83 g, 5 mmol) were dissolved in THF (30 ml) at 273 K. The yellow solution was cooled to 195 K. Dichlorophenylphosphine (0.7 ml, 5 mmol) was added. The solution was kept at this temperature for an hour before being allowed to react at room temperature overnight. The solvent was removed and the residue extracted with dichloromethane to give a light yellow oil. The oil was dissolved in acetonitrile (30 ml) and 30% hydrogen peroxide (0.56 cm l, 5 mmol) was added. After 24 h, the solution was filtered. Colorless crystals of 2-methylphenylamidinium phenylphosphinate were first obtained; the second crop yielded the title compound (yield 0.04 g).

Refinement

The hydroxy and ammonium H atoms were located in a difference Fourier map, and were refined with distance restraints of O—H = N—H 0.85 (1) Å and H···H 1.39 (1) Å. Their temperature factors were freely refined. The aromatic H atoms were placed at calculated positions, and were included in the refinement in the riding model approximation, with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure, showing the atom-numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

Crystal data

NH4+·C6H6O3PF000 = 736
Mr = 175.12Dx = 1.321 Mg m3
Orthorhombic, PbcnMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 3647 reflections
a = 31.122 (2) Åθ = 2.6–27.5º
b = 7.1249 (5) ŵ = 0.27 mm1
c = 7.9441 (5) ÅT = 293 (2) K
V = 1761.5 (2) Å3Block, colorless
Z = 80.4 × 0.4 × 0.2 mm

Data collection

Bruker SMART 1000 diffractometer1565 independent reflections
Radiation source: fine-focus sealed tube1540 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 293(2) Kθmax = 25.0º
[var phi] and ω scansθmin = 1.3º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −37→30
Tmin = 0.807, Tmax = 0.947k = −8→6
7880 measured reflectionsl = −9→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.066H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.173  w = 1/[σ2(Fo2) + (0.073P)2 + 2.2855P] where P = (Fo2 + 2Fc2)/3
S = 1.27(Δ/σ)max = 0.001
1565 reflectionsΔρmax = 0.31 e Å3
120 parametersΔρmin = −0.39 e Å3
11 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
P10.42250 (3)0.69330 (12)0.59684 (10)0.0317 (3)
O10.45014 (8)0.6911 (4)0.4300 (3)0.0410 (7)
H10.4413 (14)0.607 (4)0.363 (4)0.056 (13)*
O20.43772 (8)0.8608 (3)0.6936 (3)0.0403 (6)
O30.42584 (8)0.5088 (3)0.6853 (3)0.0431 (7)
N10.46015 (10)0.8111 (4)1.0270 (4)0.0373 (7)
H110.4547 (9)0.827 (4)0.9228 (14)0.053 (13)*
H120.4455 (8)0.720 (3)1.065 (3)0.052 (13)*
H130.4869 (4)0.786 (4)1.038 (4)0.043 (11)*
H140.4541 (9)0.910 (2)1.081 (3)0.048 (12)*
C10.36793 (11)0.7216 (5)0.5282 (5)0.0381 (8)
C20.33569 (14)0.6096 (7)0.5945 (6)0.0566 (11)
H20.34230.51940.67510.068*
C30.29380 (15)0.6318 (9)0.5410 (8)0.0742 (15)
H30.27220.55840.58790.089*
C40.28380 (16)0.7611 (9)0.4195 (8)0.0802 (16)
H40.25560.77250.38220.096*
C50.31517 (17)0.8734 (8)0.3528 (7)0.0755 (15)
H50.30820.96190.27110.091*
C60.35723 (14)0.8548 (6)0.4073 (6)0.0565 (11)
H60.37850.93200.36270.068*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0411 (5)0.0288 (5)0.0252 (5)−0.0007 (3)−0.0013 (3)0.0022 (3)
O10.0427 (14)0.0516 (16)0.0289 (13)−0.0082 (12)−0.0003 (11)−0.0042 (11)
O20.0564 (15)0.0319 (12)0.0326 (13)−0.0039 (11)−0.0083 (11)−0.0017 (10)
O30.0605 (16)0.0326 (13)0.0362 (13)0.0034 (12)−0.0034 (11)0.0064 (11)
N10.0479 (19)0.0322 (16)0.0318 (16)−0.0016 (13)−0.0031 (14)0.0005 (13)
C10.0419 (19)0.0355 (18)0.0369 (19)0.0011 (15)0.0009 (15)−0.0046 (15)
C20.054 (2)0.060 (3)0.056 (3)−0.008 (2)0.001 (2)0.002 (2)
C30.041 (2)0.092 (4)0.089 (4)−0.011 (2)0.004 (2)−0.011 (3)
C40.045 (3)0.099 (4)0.097 (4)0.016 (3)−0.018 (3)−0.019 (4)
C50.066 (3)0.078 (3)0.082 (3)0.017 (3)−0.026 (3)0.011 (3)
C60.055 (3)0.055 (2)0.060 (3)0.005 (2)−0.011 (2)0.014 (2)

Geometric parameters (Å, °)

P1—O31.494 (2)C1—C61.391 (5)
P1—O21.497 (2)C2—C31.380 (7)
P1—O11.580 (3)C2—H20.9300
P1—C11.795 (4)C3—C41.370 (8)
O1—H10.85 (1)C3—H30.9300
N1—H110.85 (1)C4—C51.369 (8)
N1—H120.85 (1)C4—H40.9300
N1—H130.85 (1)C5—C61.385 (6)
N1—H140.85 (1)C5—H50.9300
C1—C21.386 (6)C6—H60.9300
O3—P1—O2115.98 (14)C3—C2—C1120.1 (5)
O3—P1—O1110.38 (14)C3—C2—H2120.0
O2—P1—O1105.45 (14)C1—C2—H2120.0
O3—P1—C1107.91 (16)C4—C3—C2120.6 (5)
O2—P1—C1111.44 (16)C4—C3—H3119.7
O1—P1—C1105.14 (15)C2—C3—H3119.7
P1—O1—H1111 (3)C5—C4—C3120.3 (5)
H11—N1—H12109.6 (14)C5—C4—H4119.9
H11—N1—H13108.8 (14)C3—C4—H4119.9
H12—N1—H13109.2 (14)C4—C5—C6119.8 (5)
H11—N1—H14109.7 (14)C4—C5—H5120.1
H12—N1—H14110.1 (14)C6—C5—H5120.1
H13—N1—H14109.5 (14)C5—C6—C1120.5 (4)
C2—C1—C6118.8 (4)C5—C6—H6119.8
C2—C1—P1120.3 (3)C1—C6—H6119.8
C6—C1—P1120.9 (3)
O3—P1—C1—C215.9 (4)P1—C1—C2—C3−179.9 (4)
O2—P1—C1—C2−112.6 (3)C1—C2—C3—C41.5 (8)
O1—P1—C1—C2133.7 (3)C2—C3—C4—C5−1.7 (9)
O3—P1—C1—C6−163.7 (3)C3—C4—C5—C60.6 (9)
O2—P1—C1—C667.8 (4)C4—C5—C6—C10.6 (8)
O1—P1—C1—C6−45.9 (4)C2—C1—C6—C5−0.8 (7)
C6—C1—C2—C3−0.3 (7)P1—C1—C6—C5178.8 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O3i0.85 (1)1.71 (2)2.526 (3)163 (4)
N1—H11···O20.85 (1)1.91 (1)2.762 (4)175 (3)
N1—H12···O3ii0.85 (1)1.99 (1)2.814 (4)164 (3)
N1—H13···O1iii0.85 (1)2.09 (2)2.940 (4)173 (3)
N1—H14···O2iv0.85 (1)1.93 (1)2.775 (4)177 (3)

Symmetry codes: (i) x, −y+1, z−1/2; (ii) x, −y+1, z+1/2; (iii) −x+1, y, −z+3/2; (iv) x, −y+2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2441).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Mahmoudkhani, A. H. & Langer, V. (2002). J. Mol. Struct.609, 97–108.
  • Rao, K. P. & Vidyasagar, K. (2005). Eur. J. Inorg. Chem. pp. 4936–4943.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Weakley, T. J. R. (1976). Acta Cryst. B32, 2889–2890.
  • Westrip, S. P. (2008). publCIF In preparation.

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