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Volume 69 
Part 8 
Pages o1362-o1363  
August 2013  

Received 25 June 2013
Accepted 19 July 2013
Online 31 July 2013

Key indicators
Single-crystal X-ray study
T = 110 K
Mean [sigma](C-C) = 0.002 Å
Disorder in solvent or counterion
R = 0.042
wR = 0.116
Data-to-parameter ratio = 27.1
Details
Open access

Tris(4-formylphenyl)phosphane oxide tetrahydrofuran hemisolvate

aDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA
Correspondence e-mail: ffroncz@lsu.edu

The title compound, C21H15O4P·0.5C4H8O, contains an ordered phosphane oxide in a general position and a tetrahydrofuran solvent molecule disordered about a twofold axis. All three aldehyde substituents are nearly coplanar with their attached benzene rings, with C-C-C-O torsion angles in the range 1.64 (17)-4.24 (19)°. All three have different conformations with respect to the P=O group, one syn, one anti, and one gauche. Two of the aldehyde substituents form intermolecular C-H...O contacts.

Related literature

For synthetic procedures, see: Bartlett et al. (1978[Bartlett, P. A., Bauer, B. & Singer, S. J. (1978). J. Am. Chem. Soc. 100, 5085-5089.]); Chalier et al. (1996[Chalier, F., Berchadsky, Y., Finet, J. P., Gronchi, G., Marque, S. & Tordo, P. (1996). J. Phys. Chem. 100, 4323-4330.]); Kumagai & Itsuno (2001[Kumagai, T. & Itsuno, S. (2001). Tetrahedron Asymmetry, 12, 2509-2516.]). For use as a precursor in supramolecular chemistry, see: Kakoullis (2007[Kakoullis, J. (2007). MS thesis, Louisiana State University, Baton Rouge, USA.]); Pariya et al. (2008[Pariya, C., Marcos, Y. S., Zhang, Y., Fronczek, F. R. & Maverick, A. W. (2008). Organometallics, 27, 4318-4324.]). For weak hydrogen bonds, see: Desiraju & Steiner (1999[Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.]). For related structures, see: Daly (1964[Daly, J. J. (1964). J. Chem. Soc. pp. 3799-3810.]); Etter & Baures (1988[Etter, M. C. & Baures, P. W. (1988). J. Am. Chem. Soc. 110, 639-640.]); Siegler et al. (2007[Siegler, M. A., Fu, Y., Simpson, G. H., King, D. P., Parkin, S. & Brock, C. P. (2007). Acta Cryst. B63, 912-925.]); Spek (1987[Spek, A. L. (1987). Acta Cryst. C43, 1233-1235.]); Brock et al. (1985[Brock, C. P., Schweizer, W. B. & Dunitz, J. D. (1985). J. Am. Chem. Soc. 107, 6964-6970.]); Lenstra (2007[Lenstra, A. T. (2007). Private communication (refcode TPEPGO12). CCDC, Cambridge, England.]); Thierbach et al. (1980[Thierbach, D., Huber, F. & Preut, H. (1980). Acta Cryst. B36, 974-977.]); Baures & Silverton (1990[Baures, P. W. & Silverton, J. V. (1990). Acta Cryst. C46, 715-717.]); Baures (1991[Baures, P. W. (1991). Acta Cryst. C47, 2715-2716.]).

[Scheme 1]

Experimental

Crystal data
  • C21H15O4P·0.5C4H8O

  • Mr = 398.35

  • Monoclinic, C 2/c

  • a = 21.371 (3) Å

  • b = 13.474 (2) Å

  • c = 13.436 (2) Å

  • [beta] = 99.018 (9)°

  • V = 3821.1 (10) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 110 K

  • 0.45 × 0.43 × 0.38 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) Tmin = 0.926, Tmax = 0.937

  • 36155 measured reflections

  • 7598 independent reflections

  • 5928 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.116

  • S = 1.03

  • 7598 reflections

  • 280 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.39 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C7-H7...O3i 0.95 2.56 3.4303 (16) 152
C14-H14...O1ii 0.95 2.50 3.1575 (14) 127
Symmetry codes: (i) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: COLLECT (Nonius, 2000[Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2638 ).


Acknowledgements

The purchase of the diffractometer was made possible by grant No. LEQSF(1999-2000)-ENH-TR-13, administered by the Louisiana Board of Regents. This work was supported in part by the US Department of Energy (DE-FG02-01ER15267).

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Bartlett, P. A., Bauer, B. & Singer, S. J. (1978). J. Am. Chem. Soc. 100, 5085-5089.  [CrossRef] [ChemPort]
Baures, P. W. (1991). Acta Cryst. C47, 2715-2716.  [CrossRef] [IUCr Journals]
Baures, P. W. & Silverton, J. V. (1990). Acta Cryst. C46, 715-717.  [CrossRef] [IUCr Journals]
Brock, C. P., Schweizer, W. B. & Dunitz, J. D. (1985). J. Am. Chem. Soc. 107, 6964-6970.  [CrossRef] [ChemPort] [Web of Science]
Chalier, F., Berchadsky, Y., Finet, J. P., Gronchi, G., Marque, S. & Tordo, P. (1996). J. Phys. Chem. 100, 4323-4330.  [CrossRef] [ChemPort]
Daly, J. J. (1964). J. Chem. Soc. pp. 3799-3810.  [CrossRef]
Desiraju, G. R. & Steiner, T. (1999). The Weak Hydrogen Bond in Structural Chemistry and Biology. New York: Oxford University Press Inc.
Etter, M. C. & Baures, P. W. (1988). J. Am. Chem. Soc. 110, 639-640.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Kakoullis, J. (2007). MS thesis, Louisiana State University, Baton Rouge, USA.
Kumagai, T. & Itsuno, S. (2001). Tetrahedron Asymmetry, 12, 2509-2516.  [CrossRef] [ChemPort]
Lenstra, A. T. (2007). Private communication (refcode TPEPGO12). CCDC, Cambridge, England.
Nonius (2000). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Pariya, C., Marcos, Y. S., Zhang, Y., Fronczek, F. R. & Maverick, A. W. (2008). Organometallics, 27, 4318-4324.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Siegler, M. A., Fu, Y., Simpson, G. H., King, D. P., Parkin, S. & Brock, C. P. (2007). Acta Cryst. B63, 912-925.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (1987). Acta Cryst. C43, 1233-1235.  [CrossRef] [IUCr Journals]
Thierbach, D., Huber, F. & Preut, H. (1980). Acta Cryst. B36, 974-977.  [CrossRef] [IUCr Journals] [Web of Science]


Acta Cryst (2013). E69, o1362-o1363   [ doi:10.1107/S1600536813020059 ]

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