Ammonium diphenyl­phosphinate monohydrate

Li, D.; Chen, J.; Guo, J.

doi:10.1107/S1600536808012907

organic compounds

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ISSN: 2056-9890

Volume 64| Part 6| June 2008| Page o1018

doi:10.1107/S1600536808012907

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Ammonium diphenylphosphinate monohydrate

Dongyang Li,^a Juan Chen ^b and Jianping Guo ^a ^*

^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 ); Dorn et al. (2001 ).

Experimental

Crystal data

NH₄⁺·C₁₂H₁₀O₂P⁻·H₂O
M_r = 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 ) 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[F² > 2σ(F²)] = 0.064
wR(F²) = 0.139
S = 1.22
2341 reflections
154 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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.

Supporting information

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

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

checkCIF report

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.

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

	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.

Ammonium diphenylphosphinate monohydrate top

Crystal data top

NH₄⁺·C₁₂H₁₀O₂P⁻·H₂O	F(000) = 536
M_r = 253.23	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3307 reflections
a = 15.027 (2) Å	θ = 2.6–27.5°
b = 6.4594 (9) Å	µ = 0.20 mm⁻¹
c = 15.484 (2) Å	T = 293 K
β = 117.394 (2)°	Block, colorless
V = 1334.4 (3) Å³	0.20 × 0.20 × 0.15 mm
Z = 4

Data collection top

Bruker SMART diffractometer	2341 independent reflections
Radiation source: fine-focus sealed tube	2208 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→13
T_min = 0.798, T_max = 0.970	k = −7→7
6237 measured reflections	l = −10→18

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.22	w = 1/[σ²(F_o²) + (0.0434P)² + 1.1014P] where P = (F_o² + 2F_c²)/3
2341 reflections	(Δ/σ)_max < 0.001
154 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

NH₄⁺·C₁₂H₁₀O₂P⁻·H₂O	V = 1334.4 (3) Å³
M_r = 253.23	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 15.027 (2) Å	µ = 0.20 mm⁻¹
b = 6.4594 (9) Å	T = 293 K
c = 15.484 (2) Å	0.20 × 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)
T_min = 0.798, T_max = 0.970	R_int = 0.021
6237 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.22	Δρ_max = 0.35 e Å⁻³
2341 reflections	Δρ_min = −0.23 e Å⁻³
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

	x	y	z	U_iso*/U_eq
P1	0.56727 (5)	0.36680 (12)	0.37497 (5)	0.0400 (2)
O1	0.48666 (15)	0.5276 (3)	0.33914 (16)	0.0547 (6)
O2	0.54859 (16)	0.1704 (3)	0.41607 (15)	0.0533 (6)
C1	0.5943 (2)	0.3010 (5)	0.2762 (2)	0.0420 (7)
C2	0.5828 (3)	0.4485 (6)	0.2071 (2)	0.0598 (9)
H2A	0.5617	0.5814	0.2119	0.072*
C3	0.6028 (3)	0.3987 (8)	0.1308 (3)	0.0797 (12)
H3A	0.5950	0.4980	0.0843	0.096*
C4	0.6340 (3)	0.2027 (9)	0.1236 (3)	0.0830 (13)
H4A	0.6467	0.1694	0.0719	0.100*
C5	0.6465 (3)	0.0569 (7)	0.1916 (3)	0.0749 (11)
H5A	0.6685	−0.0750	0.1866	0.090*
C6	0.6266 (2)	0.1035 (5)	0.2679 (2)	0.0564 (8)
H6A	0.6347	0.0028	0.3139	0.068*
C7	0.6820 (2)	0.4771 (5)	0.4685 (2)	0.0407 (7)
C8	0.7658 (3)	0.3527 (5)	0.5140 (3)	0.0627 (9)
H8A	0.7633	0.2162	0.4940	0.075*
C9	0.8532 (3)	0.4287 (7)	0.5888 (3)	0.0774 (12)
H9A	0.9091	0.3434	0.6184	0.093*
C10	0.8579 (3)	0.6274 (7)	0.6192 (3)	0.0716 (11)
H10A	0.9161	0.6770	0.6709	0.086*
C11	0.7768 (3)	0.7541 (6)	0.5736 (3)	0.0703 (11)
H11A	0.7806	0.8913	0.5932	0.084*
C12	0.6887 (2)	0.6800 (5)	0.4982 (2)	0.0534 (8)
H12A	0.6338	0.7677	0.4676	0.064*
N1	0.59203 (18)	0.1330 (4)	0.61263 (18)	0.0504 (6)
H1B	0.5862	0.1470	0.5534	0.060*
H2B	0.5684	0.2453	0.6275	0.060*
H3B	0.5561	0.0262	0.6140	0.060*
H4B	0.6553	0.1138	0.6545	0.060*
O3	0.7070 (2)	0.6051 (7)	0.7434 (2)	0.1340 (16)
H3C	0.6462	0.5714	0.7278	0.161*
H3D	0.7095	0.7079	0.7096	0.161*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0376 (4)	0.0409 (4)	0.0432 (4)	−0.0016 (3)	0.0201 (3)	−0.0034 (3)
O1	0.0422 (11)	0.0567 (13)	0.0625 (14)	0.0058 (10)	0.0216 (10)	−0.0087 (11)
O2	0.0611 (14)	0.0503 (13)	0.0534 (13)	−0.0120 (10)	0.0305 (11)	−0.0035 (10)
C1	0.0351 (14)	0.0484 (17)	0.0405 (15)	−0.0034 (13)	0.0156 (12)	−0.0034 (13)
C2	0.057 (2)	0.068 (2)	0.0519 (19)	−0.0010 (17)	0.0231 (16)	0.0048 (17)
C3	0.082 (3)	0.108 (4)	0.054 (2)	−0.006 (3)	0.035 (2)	0.014 (2)
C4	0.081 (3)	0.123 (4)	0.058 (2)	−0.008 (3)	0.042 (2)	−0.018 (3)
C5	0.072 (2)	0.084 (3)	0.078 (3)	0.008 (2)	0.043 (2)	−0.021 (2)
C6	0.0540 (19)	0.063 (2)	0.0546 (19)	0.0080 (16)	0.0267 (16)	−0.0034 (16)
C7	0.0421 (15)	0.0459 (16)	0.0368 (15)	−0.0053 (13)	0.0205 (12)	0.0007 (13)
C8	0.055 (2)	0.051 (2)	0.064 (2)	0.0025 (16)	0.0117 (17)	0.0060 (16)
C9	0.051 (2)	0.084 (3)	0.071 (2)	0.002 (2)	0.0048 (18)	0.013 (2)
C10	0.057 (2)	0.100 (3)	0.0471 (19)	−0.025 (2)	0.0145 (17)	−0.007 (2)
C11	0.076 (3)	0.071 (2)	0.067 (2)	−0.021 (2)	0.034 (2)	−0.027 (2)
C12	0.0528 (18)	0.0526 (19)	0.0547 (19)	−0.0037 (15)	0.0247 (15)	−0.0121 (15)
N1	0.0457 (14)	0.0514 (15)	0.0546 (15)	0.0003 (12)	0.0236 (12)	−0.0039 (12)
O3	0.0596 (18)	0.198 (4)	0.106 (2)	−0.038 (2)	0.0049 (17)	0.057 (3)

Geometric parameters (Å, º) top

P1—O1	1.495 (2)	C7—C8	1.383 (4)
P1—O2	1.503 (2)	C8—C9	1.381 (5)
P1—C1	1.804 (3)	C8—H8A	0.9300
P1—C7	1.811 (3)	C9—C10	1.358 (6)
C1—C2	1.384 (4)	C9—H9A	0.9300
C1—C6	1.392 (4)	C10—C11	1.364 (5)
C2—C3	1.384 (5)	C10—H10A	0.9300
C2—H2A	0.9300	C11—C12	1.386 (5)
C3—C4	1.372 (6)	C11—H11A	0.9300
C3—H3A	0.9300	C12—H12A	0.9300
C4—C5	1.360 (6)	N1—H1B	0.8844
C4—H4A	0.9300	N1—H2B	0.8830
C5—C6	1.378 (5)	N1—H3B	0.8823
C5—H5A	0.9300	N1—H4B	0.8782
C6—H6A	0.9300	O3—H3C	0.8585
C7—C12	1.377 (4)	O3—H3D	0.8572

O1—P1—O2	117.81 (13)	C12—C7—P1	122.5 (2)
O1—P1—C1	108.00 (13)	C8—C7—P1	119.2 (2)
O2—P1—C1	108.59 (13)	C9—C8—C7	120.9 (3)
O1—P1—C7	109.50 (13)	C9—C8—H8A	119.6
O2—P1—C7	106.73 (13)	C7—C8—H8A	119.6
C1—P1—C7	105.56 (13)	C10—C9—C8	120.3 (4)
C2—C1—C6	118.9 (3)	C10—C9—H9A	119.9
C2—C1—P1	119.8 (3)	C8—C9—H9A	119.9
C6—C1—P1	121.2 (2)	C9—C10—C11	119.8 (3)
C1—C2—C3	120.1 (4)	C9—C10—H10A	120.1
C1—C2—H2A	119.9	C11—C10—H10A	120.1
C3—C2—H2A	119.9	C10—C11—C12	120.5 (4)
C4—C3—C2	120.0 (4)	C10—C11—H11A	119.7
C4—C3—H3A	120.0	C12—C11—H11A	119.7
C2—C3—H3A	120.0	C7—C12—C11	120.3 (3)
C5—C4—C3	120.4 (4)	C7—C12—H12A	119.9
C5—C4—H4A	119.8	C11—C12—H12A	119.9
C3—C4—H4A	119.8	H1B—N1—H2B	109.1
C4—C5—C6	120.3 (4)	H1B—N1—H3B	109.5
C4—C5—H5A	119.8	H2B—N1—H3B	108.2
C6—C5—H5A	119.8	H1B—N1—H4B	109.7
C5—C6—C1	120.1 (4)	H2B—N1—H4B	110.6
C5—C6—H6A	119.9	H3B—N1—H4B	109.7
C1—C6—H6A	119.9	H3C—O3—H3D	111.4
C12—C7—C8	118.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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+3/2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	NH₄⁺·C₁₂H₁₀O₂P⁻·H₂O
M_r	253.23
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	15.027 (2), 6.4594 (9), 15.484 (2)
β (°)	117.394 (2)
V (Å³)	1334.4 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.798, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	6237, 2341, 2208
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.139, 1.22
No. of reflections	2341
No. of parameters	154
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
N1—H1B···O2	0.88	1.94	2.814 (3)	170.0
N1—H2B···O1ⁱ	0.88	1.87	2.752 (3)	176.4
N1—H3B···O2ⁱⁱ	0.88	1.91	2.764 (3)	163.9
N1—H4B···O3ⁱⁱⁱ	0.88	1.94	2.816 (4)	171.9
O3—H3C···O1ⁱ	0.86	1.89	2.723 (4)	163.7

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.

Acknowledgements

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

References

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