(IUCr) 2-Thienylcarbonylmethylene-triphenylphosphorane ylide

Volume 64
Part 4
Page o647
April 2008

Received 21 January 2008
Accepted 26 February 2008
Online 5 March 2008

Key indicators
Single-crystal X-ray study
T = 120 K
Mean (C-C) = 0.003 Å
R = 0.043
wR = 0.116
Data-to-parameter ratio = 16.9
Details

2-Thienylcarbonylmethylene-triphenylphosphorane ylide

Seyyed Javad Sabounchei,^a ^* Vida Jodaian ^a and Hamid Reza Khavasi ^b

^aFaculty of Chemistry, Bu-Ali Sina University, Hamadan 65174, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, Evin, Tehran 1983963113, Iran
Correspondence e-mail: jsabounchei@yahoo.co.uk

In the molecule of the title compound, (2-thienylcarbonyl)(triphenylphosphonio)methanide, C₂₄H₁₉OPS, the geometry around the P atom is nearly tetrahedral and the O-C-C-P torsion angle is 2.80 (3)°. The thiophene ring is twisted through an angle of 4.33 (4)° with respect to the plane of the carbonyl group. Inter- and intramolecular hydrogen bonds and C-H [pi] interactions are present in the crystal structure.

Related literature

For related literature, see: Allen et al. (1987); Bart (1969); Dunitz (1979).

Experimental

Crystal data

C₂₄H₁₉OPS
M_r = 386.43
Monoclinic, C c
a = 11.3076 (17) Å
b = 15.474 (2) Å
c = 11.3540 (16) Å
= 97.063 (12)°
V = 1971.6 (5) Å³
Z = 4
Mo K radiation
= 0.26 mm^-1
T = 120 (2) K
0.4 × 0.25 × 0.2 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: numerical (X-RED32; Stoe & Cie, 2005) T_min = 0.930, T_max = 0.950
7138 measured reflections
4130 independent reflections
4082 reflections with I > 2(I)
R_int = 0.059

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.116
S = 1.03
4130 reflections
244 parameters
2 restraints
H-atom parameters constrained
_max = 0.73 e Å^-3
_min = -0.48 e Å^-3
Absolute structure: Flack (1983), 3361 Friedel pairs
Flack parameter: 0.03 (7)

Table 1
Selected geometric parameters (Å, °)

C6-P1	1.727 (2)
C7-P1	1.806 (2)
C13-P1	1.812 (2)
C19-P1	1.816 (2)

C6-P1-C7	106.06 (10)
C6-P1-C13	117.09 (12)
C7-P1-C13	106.16 (10)
C6-P1-C19	112.72 (10)
C7-P1-C19	108.67 (10)
C13-P1-C19	105.74 (10)

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C9-H9O1ⁱ	0.93	2.34	3.147 (3)	145
C14-H14O1	0.93	2.52	3.187 (3)	129
C3-H3Cg1ⁱⁱ	0.93	2.82	3.582 (3)	140
C8-H8Cg2ⁱⁱ	0.93	2.80	3.592 (2)	143
C10-H10Cg2ⁱ	0.93	2.95	3.734 (3)	143
C23-H23Cg3ⁱⁱⁱ	0.93	2.82	3.465 (3)	127
Symmetry code: (i) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x, -y, z+{\script{1\over 2}}]$ ; (iii) $[x, -y, z-{\script{1\over 2}}]$ . Cg1 is the centroid of atoms C7-C12, Cg2 is the centroid of atoms C19-C24 and Cg3 is the centroid of atoms C13-C18.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2064 ).

Acknowledgements

The authors acknowledge Bu-Ali Sina University for financial support.

References

Allen, F. H., Kennard, O., Waston, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-S19.
Bart, J. C. J. (1969). J. Chem. Soc. B, pp. 350-365.
Dunitz, J. D. (1979). X-ray Analysis and the Structure of Organic Molecules. Ithaca: Cornell University Press.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2005). X-RED32, X-AREA and X-SHAPE. Stoe & Cie, Darmstadt, Germany.

organic compounds