Diethyl­ammonium anilino(meth­oxy)­phosphinate

Fu, Z.; Liu, X.

doi:10.1107/S1600536808033023

Volume 64
Part 11
Page o2171
November 2008

Received 9 August 2008
Accepted 12 October 2008
Online 22 October 2008

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.004 Å
R = 0.039
wR = 0.081
Data-to-parameter ratio = 14.9
Details

Diethylammonium anilino(methoxy)phosphinate

Zhiyong Fu ^a ^* and Xiaoling Liu ^a

^aSchool of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou, People's Republic of China
Correspondence e-mail: zyfu@scut.edu.cn

The title compound, [Et₂NH₂][(EtO)PO₂(C₆H₅NH)] or C₄H₁₂N⁺·C₈H₁₁NO₃P^-, is a molecular salt with two anions containing PO₃N groupings and two cations in the asymmetric unit. A network of N-HO hydrogen bonds link the cations and anions into a two-dimensional network.

Related literature

For the use of N-substituted phosphoramidic acids in the synthesis of pyrophosphate groups, see: Quin & Jankowski (1994). For a corresponding dimer complex with similar P-O and P-N connections, see: Andrianov et al. (1977).

Experimental

Crystal data

C₄H₁₂N⁺·C₈H₁₁NO₃P^-
M_r = 274.29
Orthorhombic, P n a 2₁
a = 14.341 (3) Å
b = 12.785 (2) Å
c = 15.997 (3) Å
V = 2933.0 (9) Å³
Z = 8
Mo K radiation
= 0.19 mm^-1
T = 173 (2) K
0.40 × 0.20 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.957, T_max = 0.989
5062 measured reflections
4847 independent reflections
4043 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(F²)] = 0.039
wR(F²) = 0.081
S = 1.03
4847 reflections
325 parameters
1 restraint
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.23 e Å^-3
Absolute structure: Flack (1983), 2649 Friedel pairs
Flack parameter: 0.06 (4)

Table 1
Selected bond lengths (Å)

N1-P1	1.670 (2)
P1-O1	1.4798 (19)
P1-O3	1.4994 (17)
P1-O2	1.5979 (18)
N2-P2	1.651 (2)
P2-O5	1.4897 (18)
P2-O4	1.4983 (19)
P2-O6	1.5969 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1BO4	0.86	2.13	2.954 (3)	161
N2-H2BO1	0.86	2.04	2.895 (3)	173
N3-H3CO4	0.90	1.88	2.742 (3)	160
N4-H4AO3	0.90	1.94	2.792 (3)	158
N3-H3BO3ⁱ	0.90	1.89	2.788 (3)	174
N4-H4BO5ⁱⁱ	0.90	1.74	2.637 (3)	172
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 1996); cell refinement: SAINT (Bruker, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: EZ2138 ).

Acknowledgements

The authors thank the NSFFPC (No. 2003 F006) and the SRP program of the SCUT for financial support.

References

Andrianov, V. G., Kalinin, A. E. & Struchkov, Yu. T. (1977). Zh. Strukt. Khim. 18, 310-317.
Bruker (1996). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Quin, L. D. & Jankowski, S. (1994). J. Org. Chem. 59, 4402-4409.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds