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Volume 64 
Part 11 
Page o2193  
November 2008  

Received 30 August 2008
Accepted 4 September 2008
Online 25 October 2008

Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.005 Å
R = 0.065
wR = 0.158
Data-to-parameter ratio = 12.7
Details
Open access

5-(2-Phenylethynyl)isobenzofuran-1,3-dione

aCollege of Chemistry, Sichuan University, Chengdu 610064, People's Republic of China, and bCollege of Materials and Chemical Engineering, Chengdu University of Technology, Chengdu 610059, People's Republic of China
Correspondence e-mail: gaosunday@yahoo.com.cn

The title compound, C16H8O3, was synthesized by the Pd-coupling reaction of phenylacetylene with 4-bromophthalic anhydride. The phenyl and isobenzofurane rings are nearly coplanar, forming a dihedral angle of 6.70 (10)°. In the crystal structure, centrosymmetrically related molecules are linked into dimers by C-H...O hydrogen bonds.

Related literature

For a general background to the synthesis and applications of the title compound, see: Hergenrother & Smith (1994[Hergenrother, P. M. & Smith, J. G. Jr (1994). Polymer, 35, 4857-4864.], 1996[Hergenrother, P. M. & Smith, J. G. Jr (1996). US Patent 5 567 800.]); Takekoshi & Terry (1994[Takekoshi, T. & Terry, J. M. (1994). Polymer, 35, 4874-4880.]); Urazoe et al. (2005[Urazoe, D., Mori, H. & Yamakawa, K. (2005). US Patent 2 005 215 820.]); Urazoe & Mori (2006[Urazoe, D. & Mori, H. (2006). Jpn Patent JP 2 006 151 904.]). For the properties of polyimides, see: Feger et al. (1989[Feger, C., Khohasteh, M. M. & McGrath, J. E. (1989). Polyimides: Chemistry, Materials, and Characterization. Amsterdam: Elsevier.]); Ghosh & Mittal (1996[Ghosh, M. K. & Mittal, K. L. (1996). Polymides: Fundamentals and Applications. New York: Dekker.]). For the crystal structure of related compounds, see: Wright & Schorzman (2000[Wright, M. E. & Schorzman, D. A. (2000). Macromolecules, 33, 8611-8617.]).

[Scheme 1]

Experimental

Crystal data
  • C16H8O3

  • Mr = 248.22

  • Triclinic, [P \overline 1]

  • a = 6.998 (3) Å

  • b = 7.518 (3) Å

  • c = 11.683 (4) Å

  • [alpha] = 89.06 (2)°

  • [beta] = 79.31 (3)°

  • [gamma] = 81.04 (2)°

  • V = 596.6 (4) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 294 (2) K

  • 0.50 × 0.40 × 0.22 mm

Data collection
  • Enraf-Nonius CAD4 diffractometer

  • Absorption correction: none

  • 2227 measured reflections

  • 2198 independent reflections

  • 1105 reflections with I > 2[sigma](I)

  • Rint = 0.007

  • 3 standard reflections every 100 reflections intensity decay: 1.8%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.158

  • S = 1.09

  • 2198 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C16-H16...O2i 0.93 2.56 3.436 (5) 158
Symmetry code: (i) -x, -y+1, -z+1.

Data collection: DIFRAC (Gabe & White, 1993[Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association Pittsburgh Meetting,. Abstract PA 104.]); cell refinement: DIFRAC; data reduction: NRCVAX (Gabe et al., 1989[Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.]); 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: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2241 ).


Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for the X-ray data collection.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Feger, C., Khohasteh, M. M. & McGrath, J. E. (1989). Polyimides: Chemistry, Materials, and Characterization. Amsterdam: Elsevier.
Gabe, E. J., Le Page, Y., Charland, J.-P., Lee, F. L. & White, P. S. (1989). J. Appl. Cryst. 22, 384-387.  [CrossRef] [ChemPort] [ISI] [details]
Gabe, E. J. & White, P. S. (1993). DIFRAC. American Crystallographic Association Pittsburgh Meetting,. Abstract PA 104.
Ghosh, M. K. & Mittal, K. L. (1996). Polymides: Fundamentals and Applications. New York: Dekker.
Hergenrother, P. M. & Smith, J. G. Jr (1994). Polymer, 35, 4857-4864.  [CrossRef] [ChemPort]
Hergenrother, P. M. & Smith, J. G. Jr (1996). US Patent 5 567 800.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Takekoshi, T. & Terry, J. M. (1994). Polymer, 35, 4874-4880.  [CrossRef] [ChemPort]
Urazoe, D. & Mori, H. (2006). Jpn Patent JP 2 006 151 904.
Urazoe, D., Mori, H. & Yamakawa, K. (2005). US Patent 2 005 215 820.
Wright, M. E. & Schorzman, D. A. (2000). Macromolecules, 33, 8611-8617.  [CrossRef] [ChemPort]


Acta Cryst (2008). E64, o2193  [ doi:10.1107/S1600536808028407 ]

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