rac-Eth­yl(phen­yl)phosphinic acid

Burrow, R.A.; da Silva, R.M.S.

doi:10.1107/S160053681204812X

Volume 68
Part 12
Page o3488
December 2012

Received 20 November 2012
Accepted 22 November 2012
Online 30 November 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.045
wR = 0.128
Data-to-parameter ratio = 25.5
Details

rac-Ethyl(phenyl)phosphinic acid

Robert A. Burrow ^a ^* and Rubia M. Siqueira da Silva ^a

^aLaboratório de Materiais Inorgânicos, Universidade Federal de Santa Maria, 97105-900 Santa Maria-RS, Brazil
Correspondence e-mail: rburrow@ewald.base.ufsm.br

The crystal structure of the title compound, C₈H₁₁O₂P, features O-HO hydrogen bonds, which link molecules related by the b-glide plane into chains along [010].

Related literature

For background to metal-organic frameworks involving phosphonate ligands, see: Gagnon et al. (2012). For details of coordination polymers constructed using phosphinic acids as the spacer ligand, see: Siqueira et al. (2006); Beckmann et al. (2009). For further details of phosphinic acids and the crystal structures of similar compounds, see: Burrow et al. (2000); Burrow & Siqueira da Silva (2011a,b). For a description of the Cambridge Structural Database, see: Allen (2002). For geometry analysis using Mogul, see: Bruno et al. (2004).

Experimental

Crystal data

C₈H₁₁O₂P
M_r = 170.14
Orthorhombic, P b c n
a = 13.5314 (16) Å
b = 8.0328 (9) Å
c = 15.922 (2) Å
V = 1730.6 (4) Å³
Z = 8
Mo K radiation
= 0.27 mm^-1
T = 296 K
0.41 × 0.12 × 0.11 mm

Data collection

Bruker X8 Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2012) T_min = 0.906, T_max = 0.971
14069 measured reflections
2650 independent reflections
1499 reflections with I > 2(I)
R_int = 0.054

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.128
S = 1.09
2650 reflections
104 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.24 e Å^-3
_min = -0.34 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	0.87 (2)	1.64 (2)	2.4931 (19)	168 (2)
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2012); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2532 ).

Acknowledgements

Financial support from the Conselho Nacional de Desenvolvimento Científico (CNPq, Brazil; grant 479747/2009-1) and the Fundação de Amparo à Pesquisa (FAPERGS, Rio Grande do Sul; grant 10/1645-9) is gratefully acknowledged, as are fellowships from CNPq (RAB; grant 308731/2009-3) and the Coordenação de Aperfeiçoamento de Pessoas de Nível Superior (CAPES, Brazil; RMSS). The diffractometer was funded by a CT-INFRA grant from the Financiadora de Estrutos e Projetos (FINEP, Brazil).

References

Allen, F. H. (2002). Acta Cryst. B58, 380-388.
Beckmann, J., Duthie, A., Rüttinger, R. & Schwich, T. (2009). Z. Anorg. Allg. Chem. 635, 1412-1419.
Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruno, I. J., Cole, J. C., Kessler, M., Luo, J., Motherwell, W. D. S., Purkis, L. H., Smith, B. R., Taylor, R., Cooper, R. I., Harris, S. E. & Orpen, A. G. (2004). J. Chem. Inf. Comput. Sci. 44, 2133-2144.
Burrow, R. A., Farrar, D. H., Lough, A. J., Siqueira, M. R. & Squizani, F. (2000). Acta Cryst. C56, e357-e358.
Burrow, R. A. & Siqueira da Silva, R. M. (2011a). Acta Cryst. E67, o1045.
Burrow, R. A. & Siqueira da Silva, R. M. (2011b). Acta Cryst. E67, o2005.
Gagnon, K. J., Perry, H. P. & Clearfield, A. (2012). Coord. Chem. Rev. 112, 1034-1054.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Siqueira, M. R., Tonetto, T. C., Rizzatti, M. R., Lang, E. S., Ellena, J. & Burrow, R. A. (2006). Inorg. Chem. Commun. 9, 537-540.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds