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Volume 69 
Part 1 
Page o1  
January 2013  

Received 22 November 2012
Accepted 28 November 2012
Online 5 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.112
Data-to-parameter ratio = 22.8
Details
Open access

(9H-Fluoren-9-yl)(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, C19H15O2P, features pairs of molecules joined by O-H...O hydrogen bonds across crystallographic inversion centers. In addition, [pi]-[pi] interactions, with a centroid-centroid distance of 3.6273 (9) Å between the fluorene ring systems, connect the dimers into chains along [01-1]. The three rings make dihedral angles of 1.34 (9), 1.52 (10) and 1.51 (7)° with each other.

Related literature

For related structues, 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.]); Vioux et al. (2004[Vioux, A., Le Bideau, J., Hubert Martin, P. & Leclerq, D. (2004). Top. Curr. Chem. 232, 145-174.]); 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.]); 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.]); Burrow & Siqueira da Silva (2012[Burrow, R. A. & da Silva, R. M. S. da (2012). Acta Cryst. E68, o3488.]). For a description of the Cambridge Structural Database and geometry checks using Mogul, see: Allen (2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]); 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.]). For hydrogen-bond information, see: Jeffrey (1997[Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding, pp. 11-16. New York: Oxford University Press.]). For the synthesis, see: Boyd & Regan (1994[Boyd, E. A. & Regan, A. C. (1994). Tetrahedron Lett. 35, 4223-4226.]).

[Scheme 1]

Experimental

Crystal data
  • C19H15O2P

  • Mr = 306.28

  • Triclinic, [P \overline 1]

  • a = 8.5736 (7) Å

  • b = 9.5668 (8) Å

  • c = 9.6750 (7) Å

  • [alpha] = 73.348 (5)°

  • [beta] = 87.388 (5)°

  • [gamma] = 83.619 (6)°

  • V = 755.49 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.19 mm-1

  • T = 100 K

  • 0.28 × 0.13 × 0.07 mm

Data collection
  • Bruker X8 Kappa APEXII diffractometer

  • Absorption correction: numerical (SADABS; Bruker, 2012[Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.941, Tmax = 0.988

  • 21221 measured reflections

  • 4614 independent reflections

  • 3560 reflections with I > 2[sigma](I)

  • Rint = 0.047

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.112

  • S = 1.03

  • 4614 reflections

  • 202 parameters

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

  • [Delta][rho]max = 0.33 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.90 (2) 1.61 (2) 2.5107 (15) 177.9 (19)
Symmetry code: (i) -x+1, -y+1, -z+1.

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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) 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: LH5563 ).


Acknowledgements

Financial support from the Conselho Nacional de Desenvolvimento Científico (CNPq, Brazil; grant No. 479747/2009-1), the Fundação de Amparo à Pesquisa (FAPERGS, Rio Grande do Sul; grant No. 10/1645-9) is gratefully acknowledged, as are fellowships from CNPq (RAB; grant No. 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]
Boyd, E. A. & Regan, A. C. (1994). Tetrahedron Lett. 35, 4223-4226.  [CrossRef] [ChemPort] [ISI]
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.  [CSD] [CrossRef] [details]
Burrow, R. A. & Siqueira da Silva, R. M. (2011b). Acta Cryst. E67, o2005.  [CrossRef] [details]
Burrow, R. A. & da Silva, R. M. S. da (2012). Acta Cryst. E68, o3488.  [CSD] [CrossRef] [details]
Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding, pp. 11-16. New York: Oxford University Press.
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.  [ISI] [CSD] [CrossRef]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Vioux, A., Le Bideau, J., Hubert Martin, P. & Leclerq, D. (2004). Top. Curr. Chem. 232, 145-174.  [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1  [ doi:10.1107/S160053681204891X ]

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