(9H-Fluoren-9-yl)(phen­yl)phosphinic acid

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

doi:10.1107/S160053681204891X

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 (C-C) = 0.002 Å
R = 0.044
wR = 0.112
Data-to-parameter ratio = 22.8
Details

(9H-Fluoren-9-yl)(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, C₁₉H₁₅O₂P, features pairs of molecules joined by O-HO 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); Vioux et al. (2004); Siqueira et al. (2006); Burrow & Siqueira da Silva (2011a,b); Burrow & Siqueira da Silva (2012). For a description of the Cambridge Structural Database and geometry checks using Mogul, see: Allen (2002); Bruno et al. (2004). For hydrogen-bond information, see: Jeffrey (1997). For the synthesis, see: Boyd & Regan (1994).

Experimental

Crystal data

C₁₉H₁₅O₂P
M_r = 306.28
Triclinic, $[P \overline 1]$
a = 8.5736 (7) Å
b = 9.5668 (8) Å
c = 9.6750 (7) Å
= 73.348 (5)°
= 87.388 (5)°
= 83.619 (6)°
V = 755.49 (10) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.941, T_max = 0.988
21221 measured reflections
4614 independent reflections
3560 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(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
_max = 0.33 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O2ⁱ	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); 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: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

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.
Boyd, E. A. & Regan, A. C. (1994). Tetrahedron Lett. 35, 4223-4226.
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.
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Burrow, R. A. & Siqueira da Silva, R. M. (2011b). Acta Cryst. E67, o2005.
Burrow, R. A. & da Silva, R. M. S. da (2012). Acta Cryst. E68, o3488.
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.
Siqueira, M. R., Tonetto, T. C., Rizzatti, M. R., Lang, E. S., Ellena, J. & Burrow, R. A. (2006). Inorg. Chem. Commun. 9, 536-540.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Vioux, A., Le Bideau, J., Hubert Martin, P. & Leclerq, D. (2004). Top. Curr. Chem. 232, 145-174.
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organic compounds