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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 [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.128
Data-to-parameter ratio = 25.5
Details
Open access

rac-Ethyl(phenyl)phosphinic acid

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-H...O 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[Gagnon, K. J., Perry, H. P. & Clearfield, A. (2012). Coord. Chem. Rev. 112, 1034-1054.]). For details of coordination polymers constructed using phosphinic acids as the spacer ligand, see: Siqueira et al. (2006[Siqueira, M. R., Tonetto, T. C., Rizzatti, M. R., Lang, E. S., Ellena, J. & Burrow, R. A. (2006). Inorg. Chem. Commun. 9, 537-540.]); Beckmann et al. (2009[Beckmann, J., Duthie, A., Rüttinger, R. & Schwich, T. (2009). Z. Anorg. Allg. Chem. 635, 1412-1419.]). For further details of phosphinic acids and the crystal structures of similar compounds, see: Burrow et al. (2000[Burrow, R. A., Farrar, D. H., Lough, A. J., Siqueira, M. R. & Squizani, F. (2000). Acta Cryst. C56, e357-e358.]); Burrow & Siqueira da Silva (2011a[Burrow, R. A. & Siqueira da Silva, R. M. (2011a). Acta Cryst. E67, o1045.],b[Burrow, R. A. & Siqueira da Silva, R. M. (2011b). Acta Cryst. E67, o2005.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). For geometry analysis using Mogul, see: Bruno et al. (2004[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.]).

[Scheme 1]

Experimental

Crystal data
  • C8H11O2P

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.906, Tmax = 0.971

  • 14069 measured reflections

  • 2650 independent reflections

  • 1499 reflections with I > 2[sigma](I)

  • Rint = 0.054

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 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[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. 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: DIAMOND (Brandenburg, 2012[Brandenburg, K. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97 and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [ISI] [CrossRef] [details]
Beckmann, J., Duthie, A., Rüttinger, R. & Schwich, T. (2009). Z. Anorg. Allg. Chem. 635, 1412-1419.  [CSD] [CrossRef] [ChemPort]
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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Burrow, R. A., Farrar, D. H., Lough, A. J., Siqueira, M. R. & Squizani, F. (2000). Acta Cryst. C56, e357-e358.  [CSD] [CrossRef] [details]
Burrow, R. A. & Siqueira da Silva, R. M. (2011a). Acta Cryst. E67, o1045.  [CrossRef] [details]
Burrow, R. A. & Siqueira da Silva, R. M. (2011b). Acta Cryst. E67, o2005.  [CrossRef] [details]
Gagnon, K. J., Perry, H. P. & Clearfield, A. (2012). Coord. Chem. Rev. 112, 1034-1054.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siqueira, M. R., Tonetto, T. C., Rizzatti, M. R., Lang, E. S., Ellena, J. & Burrow, R. A. (2006). Inorg. Chem. Commun. 9, 537-540.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2012). E68, o3488  [ doi:10.1107/S160053681204812X ]

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