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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1018.
Published online 2008 May 7. doi:  10.1107/S1600536808012907
PMCID: PMC2961549

Ammonium diphenyl­phosphinate monohydrate

Abstract

In the title salt, NH4 +·C12H10O2P·H2O, the ion pair and water mol­ecule inter­act through hydrogen bonds to form a layer structure.

Related literature

For other ammonium diphenyl­phosphinates, see: Guo et al. (2005 [triangle]); Dorn et al. (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o1018-scheme1.jpg

Experimental

Crystal data

  • NH4 +·C12H10O2P·H2O
  • M r = 253.23
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1018-efi1.jpg
  • a = 15.027 (2) Å
  • b = 6.4594 (9) Å
  • c = 15.484 (2) Å
  • β = 117.394 (2)°
  • V = 1334.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.20 mm−1
  • T = 293 (2) K
  • 0.20 × 0.20 × 0.15 mm

Data collection

  • Bruker SMART diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.798, T max = 0.970
  • 6237 measured reflections
  • 2341 independent reflections
  • 2208 reflections with I > 2σ(I)
  • R int = 0.021

Refinement

  • R[F 2 > 2σ(F 2)] = 0.064
  • wR(F 2) = 0.139
  • S = 1.22
  • 2341 reflections
  • 154 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.23 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: SHELXTL/PC (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL/PC.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808012907/ng2451sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012907/ng2451Isup2.hkl

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

Acknowledgments

This work received funding from the Shanxi Returned Overseas Scholar Foundation.

supplementary crystallographic information

Comment

The title compound is a by-product when synthesizing 3-Cyanophenyl-amidinium diphenylphosphinate. Within the OPO fragment of the diphenylphosphinate anion, the P—O distances are 1.495 (2) and 1.503 (2) Å. The similar values was reported in the structure of arylamidinium diphenylphosphinate (Guo et al., 2005). The P—O distances indicate that the charge of the diphenylphosphinate anion [Ph2PO2]- is delocalized over the O—P—O framework. There are two types of hydrogen bond, namely P—O···H—N and P—O···H—O. The O—N distances are in the range of 2.752 (3)–2.816 (4) Å. The O—O distance is 2.723 (4) Å.

Experimental

1,3-Dicyanobenzene (0.38 g, 3 mmol) and LiN(SiMe3)2 (1.0 g, 6 mmol) were dissolveded in THF (30 cm3) at 0°C. The resultant yellow solution was warmed to room temperature and stirred for an additional 2 h before cooling down to -78°C. Chlorodiphenylphosphine (1.1 cm3, 6 mmol) was then slowly added to the reaction mixture which was stirred at -78°C for an hour before warming up to room temperature and allowed to react overnight. Solvent was then removed in vacuum. The residue was extracted with dichloromethane and the solution was filtered. The solvent of the filtrate was removed in vacuum to give a dark red oilyproduct. The product was dissolved in acetonitrile (30 cm3) and 30% hydrogen peroxide (0.68 cm3, 6 mmol) was added in air. After stirring for 24 h at room temperature, the reaction mixture was filtered. The colorless crystals of compound 3-Cyanophenyl-amidinium diphenylphosphinate were produced first; then colorless crystals of the title compound were obtained. Yield: 0.50 g, 2.1 mmol, m.p. 185–187 °C. 1H NMR (300 MHz, [D6]DMSO): d = 7.27 (m, 6H, Ar),7.61–7.64 (m, 4H, Ar). 13CNMR (75 MHz, [D6]DMSO): δ = 130.7, 130.9,132.7, 134.2, 144.1. 31P NMR (121.5 MHz, [D6]DMSO): δ = 13.3. IR (cm-1,in KBr): 3611m, 3071 b s, 3009 b s, 2833 b s, 1638m, 1483 s, 1400m, 1163vs, 1128vs, 1068m, 1040vs, 1020 s, 962m, 725vs, 694 s, 565vs.

Refinement

The ammonium and water H atoms were found by using fourier difference map and constrained to their related atoms, with N—H distances in the range 0.88 Å and Uiso(H) = 1.2Ueq(N), O—H distances in the range 0.86 Å and Uiso(H) = 1.2Ueq(O). The phenyl H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93 Å and 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. The water molecule was omitted.
Fig. 2.
The infinite chain. The waters and all of H atoms were omitted.

Crystal data

NH4+·C12H10O2P·H2OF000 = 536
Mr = 253.23Dx = 1.260 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3307 reflections
a = 15.027 (2) Åθ = 2.6–27.5º
b = 6.4594 (9) ŵ = 0.20 mm1
c = 15.484 (2) ÅT = 293 (2) K
β = 117.394 (2)ºBlock, colorless
V = 1334.4 (3) Å30.20 × 0.20 × 0.15 mm
Z = 4

Data collection

Bruker SMART diffractometer2341 independent reflections
Radiation source: fine-focus sealed tube2208 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.021
T = 293(2) Kθmax = 25.0º
ω scansθmin = 2.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −17→13
Tmin = 0.798, Tmax = 0.970k = −7→7
6237 measured reflectionsl = −10→18

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064H-atom parameters constrained
wR(F2) = 0.139  w = 1/[σ2(Fo2) + (0.0434P)2 + 1.1014P] where P = (Fo2 + 2Fc2)/3
S = 1.22(Δ/σ)max < 0.001
2341 reflectionsΔρmax = 0.35 e Å3
154 parametersΔρmin = −0.23 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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.

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

xyzUiso*/Ueq
P10.56727 (5)0.36680 (12)0.37497 (5)0.0400 (2)
O10.48666 (15)0.5276 (3)0.33914 (16)0.0547 (6)
O20.54859 (16)0.1704 (3)0.41607 (15)0.0533 (6)
C10.5943 (2)0.3010 (5)0.2762 (2)0.0420 (7)
C20.5828 (3)0.4485 (6)0.2071 (2)0.0598 (9)
H2A0.56170.58140.21190.072*
C30.6028 (3)0.3987 (8)0.1308 (3)0.0797 (12)
H3A0.59500.49800.08430.096*
C40.6340 (3)0.2027 (9)0.1236 (3)0.0830 (13)
H4A0.64670.16940.07190.100*
C50.6465 (3)0.0569 (7)0.1916 (3)0.0749 (11)
H5A0.6685−0.07500.18660.090*
C60.6266 (2)0.1035 (5)0.2679 (2)0.0564 (8)
H6A0.63470.00280.31390.068*
C70.6820 (2)0.4771 (5)0.4685 (2)0.0407 (7)
C80.7658 (3)0.3527 (5)0.5140 (3)0.0627 (9)
H8A0.76330.21620.49400.075*
C90.8532 (3)0.4287 (7)0.5888 (3)0.0774 (12)
H9A0.90910.34340.61840.093*
C100.8579 (3)0.6274 (7)0.6192 (3)0.0716 (11)
H10A0.91610.67700.67090.086*
C110.7768 (3)0.7541 (6)0.5736 (3)0.0703 (11)
H11A0.78060.89130.59320.084*
C120.6887 (2)0.6800 (5)0.4982 (2)0.0534 (8)
H12A0.63380.76770.46760.064*
N10.59203 (18)0.1330 (4)0.61263 (18)0.0504 (6)
H1B0.58620.14700.55340.060*
H2B0.56840.24530.62750.060*
H3B0.55610.02620.61400.060*
H4B0.65530.11380.65450.060*
O30.7070 (2)0.6051 (7)0.7434 (2)0.1340 (16)
H3C0.64620.57140.72780.161*
H3D0.70950.70790.70960.161*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
P10.0376 (4)0.0409 (4)0.0432 (4)−0.0016 (3)0.0201 (3)−0.0034 (3)
O10.0422 (11)0.0567 (13)0.0625 (14)0.0058 (10)0.0216 (10)−0.0087 (11)
O20.0611 (14)0.0503 (13)0.0534 (13)−0.0120 (10)0.0305 (11)−0.0035 (10)
C10.0351 (14)0.0484 (17)0.0405 (15)−0.0034 (13)0.0156 (12)−0.0034 (13)
C20.057 (2)0.068 (2)0.0519 (19)−0.0010 (17)0.0231 (16)0.0048 (17)
C30.082 (3)0.108 (4)0.054 (2)−0.006 (3)0.035 (2)0.014 (2)
C40.081 (3)0.123 (4)0.058 (2)−0.008 (3)0.042 (2)−0.018 (3)
C50.072 (2)0.084 (3)0.078 (3)0.008 (2)0.043 (2)−0.021 (2)
C60.0540 (19)0.063 (2)0.0546 (19)0.0080 (16)0.0267 (16)−0.0034 (16)
C70.0421 (15)0.0459 (16)0.0368 (15)−0.0053 (13)0.0205 (12)0.0007 (13)
C80.055 (2)0.051 (2)0.064 (2)0.0025 (16)0.0117 (17)0.0060 (16)
C90.051 (2)0.084 (3)0.071 (2)0.002 (2)0.0048 (18)0.013 (2)
C100.057 (2)0.100 (3)0.0471 (19)−0.025 (2)0.0145 (17)−0.007 (2)
C110.076 (3)0.071 (2)0.067 (2)−0.021 (2)0.034 (2)−0.027 (2)
C120.0528 (18)0.0526 (19)0.0547 (19)−0.0037 (15)0.0247 (15)−0.0121 (15)
N10.0457 (14)0.0514 (15)0.0546 (15)0.0003 (12)0.0236 (12)−0.0039 (12)
O30.0596 (18)0.198 (4)0.106 (2)−0.038 (2)0.0049 (17)0.057 (3)

Geometric parameters (Å, °)

P1—O11.495 (2)C7—C81.383 (4)
P1—O21.503 (2)C8—C91.381 (5)
P1—C11.804 (3)C8—H8A0.9300
P1—C71.811 (3)C9—C101.358 (6)
C1—C21.384 (4)C9—H9A0.9300
C1—C61.392 (4)C10—C111.364 (5)
C2—C31.384 (5)C10—H10A0.9300
C2—H2A0.9300C11—C121.386 (5)
C3—C41.372 (6)C11—H11A0.9300
C3—H3A0.9300C12—H12A0.9300
C4—C51.360 (6)N1—H1B0.8844
C4—H4A0.9300N1—H2B0.8830
C5—C61.378 (5)N1—H3B0.8823
C5—H5A0.9300N1—H4B0.8782
C6—H6A0.9300O3—H3C0.8585
C7—C121.377 (4)O3—H3D0.8572
O1—P1—O2117.81 (13)C12—C7—P1122.5 (2)
O1—P1—C1108.00 (13)C8—C7—P1119.2 (2)
O2—P1—C1108.59 (13)C9—C8—C7120.9 (3)
O1—P1—C7109.50 (13)C9—C8—H8A119.6
O2—P1—C7106.73 (13)C7—C8—H8A119.6
C1—P1—C7105.56 (13)C10—C9—C8120.3 (4)
C2—C1—C6118.9 (3)C10—C9—H9A119.9
C2—C1—P1119.8 (3)C8—C9—H9A119.9
C6—C1—P1121.2 (2)C9—C10—C11119.8 (3)
C1—C2—C3120.1 (4)C9—C10—H10A120.1
C1—C2—H2A119.9C11—C10—H10A120.1
C3—C2—H2A119.9C10—C11—C12120.5 (4)
C4—C3—C2120.0 (4)C10—C11—H11A119.7
C4—C3—H3A120.0C12—C11—H11A119.7
C2—C3—H3A120.0C7—C12—C11120.3 (3)
C5—C4—C3120.4 (4)C7—C12—H12A119.9
C5—C4—H4A119.8C11—C12—H12A119.9
C3—C4—H4A119.8H1B—N1—H2B109.1
C4—C5—C6120.3 (4)H1B—N1—H3B109.5
C4—C5—H5A119.8H2B—N1—H3B108.2
C6—C5—H5A119.8H1B—N1—H4B109.7
C5—C6—C1120.1 (4)H2B—N1—H4B110.6
C5—C6—H6A119.9H3B—N1—H4B109.7
C1—C6—H6A119.9H3C—O3—H3D111.4
C12—C7—C8118.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1B···O20.881.942.814 (3)170
N1—H2B···O1i0.881.872.752 (3)176
N1—H3B···O2ii0.881.912.764 (3)164
N1—H4B···O3iii0.881.942.816 (4)172
O3—H3C···O1i0.861.892.723 (4)164

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2451).

References

  • Bruker (2000). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Dorn, H., Lough, A. J. & Manners, I. (2001). Acta Cryst. E57, o928–o929.
  • Guo, J., Wong, W.-K. & Wong, W.-Y. (2005). Polyhedron, 24, 927–939.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography