[Journal logo]

Volume 69 
Part 2 
Page o245  
February 2013  

Received 23 December 2012
Accepted 13 January 2013
Online 19 January 2013

[pv2616sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.093
Data-to-parameter ratio = 13.7
Details
Open access

3-[2-(Triphenylphosphanylidene)acetyl]-2H-chromen-2-one

Muhammad Taha,a Nor Hadiani Ismail,b,c Ahmad Nazif Aziza,d Syed Adnan Ali Shaha,e and Sammer Yousuff*

aAtta-ur-Rahman Institute for Natural Product Discovery (RiND), Universiti Teknologi MARA (UiTM), Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D. E., Malaysia,bFaculty of Applied Science, Universiti Teknologi MARA (UiTM), 40450 Shah Alam, Selangor D. E., Malaysia,cFaculty of Applied Sciences, Universiti Teknologi MARA (UiTM), 40000 Shah Alam, Selangor D. E., Malaysia,dDepartment of Chemical Sciences, Faculty of Science and Technology, University Malaysia Terengganu, 21030 Kuala Terengganu, Malaysia,eDepartment of Pharmacology and Chemistry, Faculty of Pharmacy, Universiti Teknologi MARA (UiMT) Puncak Alam Campus, 42300 Puncak Alam, Selangor D. E., Malaysia, and fH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the title compound, C29H21O3P, a coumarin-substitued ylid, the P atom is linked to three benzene rings and a planar coumarin moiety via a methylenecarbonyl group. The bond lengths in the P=C-C=O fragment clearly indicate a delocalized system involving the olefinic and carbonyl bonds. The molecular structure is stabilized by an intramolecular C-H...O interaction that results in an S7 graph-set ring motif. In the crystal, molecules are linked into a three-dimensional framework by C-H...O hydrogen bonds.

Related literature

For applications and biological activity of coumarin, see: Kabak et al. (1999[Kabak, M., Elmali, A. & Elerman, Y. (1999). J. Mol. Struct. 477, 151-158.]); El-Ansary et al. (1992[El-Ansary, S. L., Aly, E. I. & Halem, M. A. (1992). Egypt. J. Pharm. Sci. 33, 379-390.]); Czerpack & Skolska (1982[Czerpack, R. & Skolska, S. (1982). Med. Dosw. Microbiol. 34, 37-50.]); Reddy & Somayojulu (1981[Reddy, Y. D. & Somayojulu, V. V. (1981). J. Indian Chem. Soc. 58, 599-601.]); Jund et al. (1971[Jund, L., Corse, J., King, A. S., Bayne, H. & Mihrag, K. (1971). Phytochemistry, 10, 2971-2974.]). For the crystal structure of a related compound, see: Schobert et al. (2000[Schobert, R., Seigfried, S., Nieuwenhuyzen, M., Milius, W. & Hampel, F. (2000). J. Chem. Soc. Perkin Trans. 1, pp. 1723-1730.]).

[Scheme 1]

Experimental

Crystal data

  • C29H21O3P

  • Mr = 448.43

  • Triclinic, [P \overline 1]

  • a = 9.7837 (12) Å

  • b = 10.3917 (14) Å

  • c = 12.2925 (17) Å

  • [alpha] = 108.669 (4)°

  • [beta] = 104.484 (4)°

  • [gamma] = 99.746 (4)°

  • V = 1103.2 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.16 mm-1

  • T = 100 K

  • 0.46 × 0.41 × 0.34 mm
Data collection

  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.932, Tmax = 0.949

  • 36693 measured reflections

  • 4102 independent reflections

  • 3716 reflections with I > 2[sigma](I)

  • Rint = 0.045
Refinement

  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.093

  • S = 1.07

  • 4102 reflections

  • 299 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.40 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2A...O2i 0.95 2.45 3.378 (2) 166
C7-H7A...O3ii 0.95 2.28 3.171 (2) 156
C22-H22A...O2iii 0.95 2.48 3.398 (2) 163
C25-H25A...O3 0.95 2.31 3.168 (2) 150
C28-H28A...O1iv 0.95 2.54 3.281 (2) 135
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y, -z+1; (iii) -x, -y+1, -z+1; (iv) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2000[Bruker (2000). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, APEX2 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: PV2616 ).

References

Bruker (2000). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Czerpack, R. & Skolska, S. (1982). Med. Dosw. Microbiol. 34, 37-50.
El-Ansary, S. L., Aly, E. I. & Halem, M. A. (1992). Egypt. J. Pharm. Sci. 33, 379-390.  [ChemPort]
Jund, L., Corse, J., King, A. S., Bayne, H. & Mihrag, K. (1971). Phytochemistry, 10, 2971-2974.
Kabak, M., Elmali, A. & Elerman, Y. (1999). J. Mol. Struct. 477, 151-158.  [ISI] [CrossRef] [ChemPort]
Reddy, Y. D. & Somayojulu, V. V. (1981). J. Indian Chem. Soc. 58, 599-601.  [ChemPort]
Schobert, R., Seigfried, S., Nieuwenhuyzen, M., Milius, W. & Hampel, F. (2000). J. Chem. Soc. Perkin Trans. 1, pp. 1723-1730.  [CSD] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2013). E69, o245  [ doi:10.1107/S160053681300127X ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.