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Volume 69 
Part 2 
Page o183  
February 2013  

Received 7 November 2012
Accepted 22 December 2012
Online 4 January 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.099
Data-to-parameter ratio = 14.9
Details
Open access

1-(4-Chlorophenyl)-2-[tris(4-methylphenyl)-[lambda]5-phosphanylidene]butane-1,3-dione

aFaculty of Chemistry, Bu-Ali Sina University, Hamedan 65174, Iran, and bInstituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior, Ciudad Universitaria, México 04510, Mexico
Correspondence e-mail: jsabounchei@yahoo.co.uk

In the title ylide, C31H28ClO2P [common name [alpha]-acetyl-[alpha]-p-chlorobenzoylmethylenetri(p-tolyl)phosphorane], the dihedral angle between the 4-chlorophenyl ring and that of the ylide moiety is 66.15 (10)°. The geometry around the P atom is slightly distorted tetrahedral [angle range = 105.22 (8)-115.52 (9)°] and the carbonyl O atoms are syn-oriented with respect to the P atom. The ylide group is close to planar [maximum deviation from the least-squares plane = 0.006 (2) Å] and the P-C, C-C and C=O bond lengths are consistent with electron delocalization involving the O atoms.

Related literature

For a general background to organophosphorus compounds and a review of stabilized phosphonium ylides, see: Bachrach & Nitsche (1994[Bachrach, S. M. & Nitsche, C. I. (1994). The Chemistry of Organophosphorus Compounds, edited by F. R. Hartley, Vol. 3, ch. 4, pp. 273-299. Chichester: Wiley.]). For other related literature on ylides, see: Wilson & Tebby (1972[Wilson, I. F. & Tebby, J. C. (1972). J. Chem. Soc. Perkin Trans. 1, pp. 31-34.]); Sabounchei et al. (2010[Sabounchei, S. J., Shahriary, P., Bolboli Nojini, Z., Khavasi, H. R., Arici, C. & Dal, H. (2010). Heteroat. Chem. 21, 475-485.]). For analogous structures, see: Bart (1969[Bart, J. C. J. (1969). J. Chem. Soc. B, pp. 350-365.]); Kalyanasundari et al. (1994[Kalyanasundari, M., Panchanatheswaran, K., Parthasarathi, V., Robinson, W. T. & Wen, H. (1994). Acta Cryst. C50, 1738-1741.]); Sabounchei et al. (2007[Sabounchei, S. J., Dadras, A., Jafarzadeh, M. & Khavasi, H. R. (2007). Acta Cryst. E63, o3160.]); Castañeda et al. (2001[Castañeda, F., Terraza, C. A., Garland, M. T., Bunton, C. A. & Baggio, R. F. (2001). Acta Cryst. C57, 180-184.], 2003[Castañeda, F., Terraza, C. A., Bunton, C. A., Gillitt, N. D. & Garland, M. T. (2003). Phosphorus Sulfur Silicon Relat. Elem. 178, 1973-1985.]). For bond distance and angle data, see: Dunitz (1979[Dunitz, J. D. (1979). X-ray Analysis and the Structure of Organic Molecules, pp. 335-340. Ithaca: Cornell University Press.]); Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orphen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C31H28ClO2P

  • Mr = 498.95

  • Monoclinic, C 2/c

  • a = 20.327 (2) Å

  • b = 14.7560 (15) Å

  • c = 18.9759 (19) Å

  • [beta] = 113.140 (2)°

  • V = 5233.8 (9) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.23 mm-1

  • T = 298 K

  • 0.35 × 0.27 × 0.25 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 21296 measured reflections

  • 4780 independent reflections

  • 3380 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.099

  • S = 1.00

  • 4780 reflections

  • 320 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART and SAINT. 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2244 ).


Acknowledgements

We are grateful to the University of Bu-Ali Sina for financial support. We are also indebted to the Instituto de Química, Universidad Nacional Autónoma de México, for the use of their X-ray diffractometer.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orphen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bachrach, S. M. & Nitsche, C. I. (1994). The Chemistry of Organophosphorus Compounds, edited by F. R. Hartley, Vol. 3, ch. 4, pp. 273-299. Chichester: Wiley.
Bart, J. C. J. (1969). J. Chem. Soc. B, pp. 350-365.
Bruker (1999). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Castañeda, F., Terraza, C. A., Bunton, C. A., Gillitt, N. D. & Garland, M. T. (2003). Phosphorus Sulfur Silicon Relat. Elem. 178, 1973-1985.  [CrossRef] [ChemPort]
Castañeda, F., Terraza, C. A., Garland, M. T., Bunton, C. A. & Baggio, R. F. (2001). Acta Cryst. C57, 180-184.  [CSD] [CrossRef] [details]
Dunitz, J. D. (1979). X-ray Analysis and the Structure of Organic Molecules, pp. 335-340. Ithaca: Cornell University Press.
Kalyanasundari, M., Panchanatheswaran, K., Parthasarathi, V., Robinson, W. T. & Wen, H. (1994). Acta Cryst. C50, 1738-1741.  [CrossRef] [details]
Sabounchei, S. J., Dadras, A., Jafarzadeh, M. & Khavasi, H. R. (2007). Acta Cryst. E63, o3160.  [CSD] [CrossRef] [details]
Sabounchei, S. J., Shahriary, P., Bolboli Nojini, Z., Khavasi, H. R., Arici, C. & Dal, H. (2010). Heteroat. Chem. 21, 475-485.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wilson, I. F. & Tebby, J. C. (1972). J. Chem. Soc. Perkin Trans. 1, pp. 31-34.  [CrossRef]


Acta Cryst (2013). E69, o183  [ doi:10.1107/S1600536812051689 ]

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