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ISSN: 2056-9890

Ammonium di­phenyl­phosphinate monohydrate

aInstitute of Applied Chemistry, Shanxi University, Taiyuan 030006, People's Republic of China, and bDepartment of Chemistry, Taiyuan Teachers' College, Taiyuan 030031, People's Republic of China
*Correspondence e-mail: guojp@sxu.edu.cn

(Received 26 April 2008; accepted 1 May 2008; online 7 May 2008)

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[Guo, J., Wong, W.-K. & Wong, W.-Y. (2005). Polyhedron, 24, 927-939.]); Dorn et al. (2001[Dorn, H., Lough, A. J. & Manners, I. (2001). Acta Cryst. E57, o928-o929.]).

[Scheme 1]

Experimental

Crystal data
  • NH4+·C12H10O2P·H2O

  • Mr = 253.23

  • Monoclinic, P 21 /n

  • 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.798, Tmax = 0.970

  • 6237 measured reflections

  • 2341 independent reflections

  • 2208 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 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

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1B⋯O2 0.88 1.94 2.814 (3) 170
N1—H2B⋯O1i 0.88 1.87 2.752 (3) 176
N1—H3B⋯O2ii 0.88 1.91 2.764 (3) 164
N1—H4B⋯O3iii 0.88 1.94 2.816 (4) 172
O3—H3C⋯O1i 0.86 1.89 2.723 (4) 164
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL/PC.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/PC (Sheldrick, 2008); software used to prepare material for publication: SHELXTL/PC (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure, showing the atom-numbering scheme. Displacement ellipsoids were drawn at the 30% probability level. The water molecule was omitted.
[Figure 2] Fig. 2. The infinite chain. The waters and all of H atoms were omitted.
Ammonium diphenylphosphinate monohydrate top
Crystal data top
NH4+·C12H10O2P·H2OF(000) = 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 = 2.6–27.5°
b = 6.4594 (9) ŵ = 0.20 mm1
c = 15.484 (2) ÅT = 293 K
β = 117.394 (2)°Block, colorless
V = 1334.4 (3) Å30.20 × 0.20 × 0.15 mm
Z = 4
Data collection top
Bruker SMART
diffractometer
2341 independent reflections
Radiation source: fine-focus sealed tube2208 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1713
Tmin = 0.798, Tmax = 0.970k = 77
6237 measured reflectionsl = 1018
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)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 1.22 w = 1/[σ2(Fo2) + (0.0434P)2 + 1.1014P]
where P = (Fo2 + 2Fc2)/3
2341 reflections(Δ/σ)max < 0.001
154 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
NH4+·C12H10O2P·H2OV = 1334.4 (3) Å3
Mr = 253.23Z = 4
Monoclinic, P21/nMo Kα radiation
a = 15.027 (2) ŵ = 0.20 mm1
b = 6.4594 (9) ÅT = 293 K
c = 15.484 (2) Å0.20 × 0.20 × 0.15 mm
β = 117.394 (2)°
Data collection top
Bruker SMART
diffractometer
2341 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2208 reflections with I > 2σ(I)
Tmin = 0.798, Tmax = 0.970Rint = 0.021
6237 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0640 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 1.22Δρmax = 0.35 e Å3
2341 reflectionsΔρmin = 0.23 e Å3
154 parameters
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. 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
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)
H5A0.66850.07500.18660.090*
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) top
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, º) top
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, º) top
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, y1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaNH4+·C12H10O2P·H2O
Mr253.23
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)15.027 (2), 6.4594 (9), 15.484 (2)
β (°) 117.394 (2)
V3)1334.4 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.20
Crystal size (mm)0.20 × 0.20 × 0.15
Data collection
DiffractometerBruker SMART
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.798, 0.970
No. of measured, independent and
observed [I > 2σ(I)] reflections
6237, 2341, 2208
Rint0.021
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.064, 0.139, 1.22
No. of reflections2341
No. of parameters154
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.23

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1B···O20.881.942.814 (3)170.0
N1—H2B···O1i0.881.872.752 (3)176.4
N1—H3B···O2ii0.881.912.764 (3)163.9
N1—H4B···O3iii0.881.942.816 (4)171.9
O3—H3C···O1i0.861.892.723 (4)163.7
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1; (iii) x+3/2, y1/2, z+3/2.
 

Acknowledgements

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

References

First citationBruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationDorn, H., Lough, A. J. & Manners, I. (2001). Acta Cryst. E57, o928–o929.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationGuo, J., Wong, W.-K. & Wong, W.-Y. (2005). Polyhedron, 24, 927–939.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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