Ammonium benzene­phospho­nate

Lin, Z.; Lei, X.-Q.; Bai, S.-D.; Ng, S.W.

doi:10.1107/S1600536808023143

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1607

doi:10.1107/S1600536808023143

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Ammonium benzenephosphonate

Zhen Lin,^a Xiu-Qing Lei,^b Sheng-Di Bai ^b and Seik Weng Ng ^c ^*

^aShanxi Vocational and Technical College of Biological Applications, Taiyuan 030031, Shanxi, People's Republic of China, ^bInstitute of Applied Chemistry, Shanxi University, Taiyuan 030006, People's Republic of China, and ^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 22 July 2008; accepted 22 July 2008; online 26 July 2008)

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

Experimental

Crystal data

NH₄⁺·C₆H₆O₃P⁻
M_r = 175.12
Orthorhombic, P b c n
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 ) 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[F² > 2σ(F²)] = 0.066
wR(F²) = 0.173
S = 1.27
1565 reflections
120 parameters
11 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3ⁱ	0.85 (1)	1.71 (2)	2.526 (3)	163 (4)
N1—H11⋯O2	0.85 (1)	1.91 (1)	2.762 (4)	175 (3)
N1—H12⋯O3ⁱⁱ	0.85 (1)	1.99 (1)	2.814 (4)	164 (3)
N1—H13⋯O1ⁱⁱⁱ	0.85 (1)	2.09 (2)	2.940 (4)	173 (3)
N1—H14⋯O2^iv	0.85 (1)	1.93 (1)	2.775 (4)	177 (3)
Symmetry codes: (i) $[x, -y+1, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y, -z+{\script{3\over 2}}]$ ; (iv) $[x, -y+2, z+{\script{1\over 2}}]$ .

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: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2008 ).

Supporting information

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

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

checkCIF report

Comment top

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

Related literature top

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

Experimental top

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).

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: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).

Figures top

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

Ammonium benzenephosphonate top

Crystal data top

NH₄⁺·C₆H₆O₃P⁻	F(000) = 736
M_r = 175.12	D_x = 1.321 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 3647 reflections
a = 31.122 (2) Å	θ = 2.6–27.5°
b = 7.1249 (5) Å	µ = 0.27 mm⁻¹
c = 7.9441 (5) Å	T = 293 K
V = 1761.5 (2) Å³	Block, colorless
Z = 8	0.4 × 0.4 × 0.2 mm

Data collection top

Bruker SMART 1000 diffractometer	1565 independent reflections
Radiation source: fine-focus sealed tube	1540 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −37→30
T_min = 0.807, T_max = 0.947	k = −8→6
7880 measured reflections	l = −9→9

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.27	w = 1/[σ²(F_o²) + (0.073P)² + 2.2855P] where P = (F_o² + 2F_c²)/3
1565 reflections	(Δ/σ)_max = 0.001
120 parameters	Δρ_max = 0.31 e Å⁻³
11 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

NH₄⁺·C₆H₆O₃P⁻	V = 1761.5 (2) Å³
M_r = 175.12	Z = 8
Orthorhombic, Pbcn	Mo Kα radiation
a = 31.122 (2) Å	µ = 0.27 mm⁻¹
b = 7.1249 (5) Å	T = 293 K
c = 7.9441 (5) Å	0.4 × 0.4 × 0.2 mm

Data collection top

Bruker SMART 1000 diffractometer	1565 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1540 reflections with I > 2σ(I)
T_min = 0.807, T_max = 0.947	R_int = 0.027
7880 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	11 restraints
wR(F²) = 0.173	H atoms treated by a mixture of independent and constrained refinement
S = 1.27	Δρ_max = 0.31 e Å⁻³
1565 reflections	Δρ_min = −0.39 e Å⁻³
120 parameters

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

	x	y	z	U_iso*/U_eq
P1	0.42250 (3)	0.69330 (12)	0.59684 (10)	0.0317 (3)
O1	0.45014 (8)	0.6911 (4)	0.4300 (3)	0.0410 (7)
H1	0.4413 (14)	0.607 (4)	0.363 (4)	0.056 (13)*
O2	0.43772 (8)	0.8608 (3)	0.6936 (3)	0.0403 (6)
O3	0.42584 (8)	0.5088 (3)	0.6853 (3)	0.0431 (7)
N1	0.46015 (10)	0.8111 (4)	1.0270 (4)	0.0373 (7)
H11	0.4547 (9)	0.827 (4)	0.9228 (14)	0.053 (13)*
H12	0.4455 (8)	0.720 (3)	1.065 (3)	0.052 (13)*
H13	0.4869 (4)	0.786 (4)	1.038 (4)	0.043 (11)*
H14	0.4541 (9)	0.910 (2)	1.081 (3)	0.048 (12)*
C1	0.36793 (11)	0.7216 (5)	0.5282 (5)	0.0381 (8)
C2	0.33569 (14)	0.6096 (7)	0.5945 (6)	0.0566 (11)
H2	0.3423	0.5194	0.6751	0.068*
C3	0.29380 (15)	0.6318 (9)	0.5410 (8)	0.0742 (15)
H3	0.2722	0.5584	0.5879	0.089*
C4	0.28380 (16)	0.7611 (9)	0.4195 (8)	0.0802 (16)
H4	0.2556	0.7725	0.3822	0.096*
C5	0.31517 (17)	0.8734 (8)	0.3528 (7)	0.0755 (15)
H5	0.3082	0.9619	0.2711	0.091*
C6	0.35723 (14)	0.8548 (6)	0.4073 (6)	0.0565 (11)
H6	0.3785	0.9320	0.3627	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P1	0.0411 (5)	0.0288 (5)	0.0252 (5)	−0.0007 (3)	−0.0013 (3)	0.0022 (3)
O1	0.0427 (14)	0.0516 (16)	0.0289 (13)	−0.0082 (12)	−0.0003 (11)	−0.0042 (11)
O2	0.0564 (15)	0.0319 (12)	0.0326 (13)	−0.0039 (11)	−0.0083 (11)	−0.0017 (10)
O3	0.0605 (16)	0.0326 (13)	0.0362 (13)	0.0034 (12)	−0.0034 (11)	0.0064 (11)
N1	0.0479 (19)	0.0322 (16)	0.0318 (16)	−0.0016 (13)	−0.0031 (14)	0.0005 (13)
C1	0.0419 (19)	0.0355 (18)	0.0369 (19)	0.0011 (15)	0.0009 (15)	−0.0046 (15)
C2	0.054 (2)	0.060 (3)	0.056 (3)	−0.008 (2)	0.001 (2)	0.002 (2)
C3	0.041 (2)	0.092 (4)	0.089 (4)	−0.011 (2)	0.004 (2)	−0.011 (3)
C4	0.045 (3)	0.099 (4)	0.097 (4)	0.016 (3)	−0.018 (3)	−0.019 (4)
C5	0.066 (3)	0.078 (3)	0.082 (3)	0.017 (3)	−0.026 (3)	0.011 (3)
C6	0.055 (3)	0.055 (2)	0.060 (3)	0.005 (2)	−0.011 (2)	0.014 (2)

Geometric parameters (Å, º) top

P1—O3	1.494 (2)	C1—C6	1.391 (5)
P1—O2	1.497 (2)	C2—C3	1.380 (7)
P1—O1	1.580 (3)	C2—H2	0.9300
P1—C1	1.795 (4)	C3—C4	1.370 (8)
O1—H1	0.85 (1)	C3—H3	0.9300
N1—H11	0.85 (1)	C4—C5	1.369 (8)
N1—H12	0.85 (1)	C4—H4	0.9300
N1—H13	0.85 (1)	C5—C6	1.385 (6)
N1—H14	0.85 (1)	C5—H5	0.9300
C1—C2	1.386 (6)	C6—H6	0.9300

O3—P1—O2	115.98 (14)	C3—C2—C1	120.1 (5)
O3—P1—O1	110.38 (14)	C3—C2—H2	120.0
O2—P1—O1	105.45 (14)	C1—C2—H2	120.0
O3—P1—C1	107.91 (16)	C4—C3—C2	120.6 (5)
O2—P1—C1	111.44 (16)	C4—C3—H3	119.7
O1—P1—C1	105.14 (15)	C2—C3—H3	119.7
P1—O1—H1	111 (3)	C5—C4—C3	120.3 (5)
H11—N1—H12	109.6 (14)	C5—C4—H4	119.9
H11—N1—H13	108.8 (14)	C3—C4—H4	119.9
H12—N1—H13	109.2 (14)	C4—C5—C6	119.8 (5)
H11—N1—H14	109.7 (14)	C4—C5—H5	120.1
H12—N1—H14	110.1 (14)	C6—C5—H5	120.1
H13—N1—H14	109.5 (14)	C5—C6—C1	120.5 (4)
C2—C1—C6	118.8 (4)	C5—C6—H6	119.8
C2—C1—P1	120.3 (3)	C1—C6—H6	119.8
C6—C1—P1	120.9 (3)

O3—P1—C1—C2	15.9 (4)	P1—C1—C2—C3	−179.9 (4)
O2—P1—C1—C2	−112.6 (3)	C1—C2—C3—C4	1.5 (8)
O1—P1—C1—C2	133.7 (3)	C2—C3—C4—C5	−1.7 (9)
O3—P1—C1—C6	−163.7 (3)	C3—C4—C5—C6	0.6 (9)
O2—P1—C1—C6	67.8 (4)	C4—C5—C6—C1	0.6 (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—C5	178.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.85 (1)	1.71 (2)	2.526 (3)	163 (4)
N1—H11···O2	0.85 (1)	1.91 (1)	2.762 (4)	175 (3)
N1—H12···O3ⁱⁱ	0.85 (1)	1.99 (1)	2.814 (4)	164 (3)
N1—H13···O1ⁱⁱⁱ	0.85 (1)	2.09 (2)	2.940 (4)	173 (3)
N1—H14···O2^iv	0.85 (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.

Experimental details

Crystal data
Chemical formula	NH₄⁺·C₆H₆O₃P⁻
M_r	175.12
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	293
a, b, c (Å)	31.122 (2), 7.1249 (5), 7.9441 (5)
V (Å³)	1761.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.4 × 0.4 × 0.2

Data collection
Diffractometer	Bruker SMART 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.807, 0.947
No. of measured, independent and observed [I > 2σ(I)] reflections	7880, 1565, 1540
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.173, 1.27
No. of reflections	1565
No. of parameters	120
No. of restraints	11
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.39

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3ⁱ	0.85 (1)	1.71 (2)	2.526 (3)	163 (4)
N1—H11···O2	0.85 (1)	1.91 (1)	2.762 (4)	175 (3)
N1—H12···O3ⁱⁱ	0.85 (1)	1.99 (1)	2.814 (4)	164 (3)
N1—H13···O1ⁱⁱⁱ	0.85 (1)	2.09 (2)	2.940 (4)	173 (3)
N1—H14···O2^iv	0.85 (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.

Acknowledgements

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

References

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