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Volume 67 
Part 5 
Page o1045  
May 2011  

Received 13 January 2011
Accepted 3 March 2011
Online 7 April 2011

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Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.039
wR = 0.108
Data-to-parameter ratio = 23.3
Details
Open access

Benzyl(phenyl)phosphinic acid

Robert A. Burrowa* and Rubia M. Siqueira da Silvaa

aLaboratório de Materiais Inorgânicos, Universidade Federal de Santa Maria, Av. Roraima, 1000 Camobi, 97105-900 Santa Maria, RS, Brazil
Correspondence e-mail: rburrow@ewald.base.ufsm.br

The title compound, C13H13O2P, crystallized as enantiomerically pure crystals; for the crystal measured, the P atom has R stereochemistry. The crystal structure displays O-H...O hydrogen bonding, which links individual molecules related by a 21 screw axis parallel to the crystallographic a-axis direction into continuous chains.

Related literature

For background to phosphinic acids, see: Beckmann et al. (2009[Beckmann, J., Duthie, A., Rüttinger, R. & Schwich, T. (2009). Z. Anorg. Allg. Chem. 635, 1412-1419.]); Burrow et al. (2000[Burrow, R. A., Farrar, D. H., Lough, A. J., Siqueira, M. R. & Squizani, F. (2000). Acta Cryst. C56, e357-e358.]); Chen & Suslick (1993[Chen, C.-T. & Suslick, K. S. (1993). Coord. Chem. Rev. 128, 293-322.]); 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, 536-540.]); Vioux et al. (2004[Vioux, A., Le Bideau, J., Hubert Mutin, P. & Leclerq, D. (2004). Top. Curr. Chem. 232, 145-174.]). For a description of the Cambridge Structural Database, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]). Geometrical analysis was performed with Mogul (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

  • C13H13O2P

  • Mr = 232.20

  • Orthorhombic, P 21 21 21

  • a = 5.7326 (2) Å

  • b = 12.3430 (3) Å

  • c = 16.7794 (4) Å

  • V = 1187.27 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 295 K

  • 0.65 × 0.34 × 0.22 mm
Data collection

  • Bruker X8 Kappa APEXII diffractometer

  • Absorption correction: gaussian (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.880, Tmax = 0.964

  • 14337 measured reflections

  • 3451 independent reflections

  • 3119 reflections with I > 2[sigma](I)

  • Rint = 0.028
Refinement

  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.108

  • S = 1.05

  • 3451 reflections

  • 148 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1447 Friedel pairs

  • Flack parameter: 0.00 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.93 (3) 1.58 (3) 2.4838 (18) 163 (3)
Symmetry code: (i) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT (Bruker, 2009[Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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, 2009[Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: 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: ZB2011 ).

Acknowledgements

Financial support from the Conselho Nacional de Desenvolvimento Científico (CNPq, Brazil; grants 485245/2007-8 and 479747/2009-1) and the Fundação de Amparo à Pesquisa (FAPERGS, Rio Grande do Sul) is gratefully acknowledged, as are fellowships from CNPq (RAB) 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.  [CrossRef] [ChemPort]
Brandenburg, K. (2009). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). 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]
Chen, C.-T. & Suslick, K. S. (1993). Coord. Chem. Rev. 128, 293-322.  [CrossRef] [ChemPort] [ISI]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
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, 536-540.  [CrossRef]
Vioux, A., Le Bideau, J., Hubert Mutin, P. & Leclerq, D. (2004). Top. Curr. Chem. 232, 145-174.  [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2011). E67, o1045  [ doi:10.1107/S1600536811008245 ]

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