Research Articles

X-ray Crystallographic Structure of 3-(Propan-2-ylidene) benzofuran-2(3H)-one

Vol. 1 No. 3 (2014) 43-49 Published October 27, 2014

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Abstract

3-(Propan-2-ylidene)benzofuran-2(3H)-one, C11H10O2, crystallizes in the monoclinic space group P21/c with unit cell parametersa =7.1869(3), b = 18.0636(10), c = 13.1656(7) b= 96.763(3), V =1697.28(15) , Z = 8 (Z? = 2 independent molecules, A and B, per asymmetric unit), Dc = 1.363 g cm-3 and the linear absorption coefficient = 0.093 mm-1. The crystal structure determination was carried out using MoKa X-ray data measured at 120(2) K. In the final refinement cycle the data/restraints/parameter ratios were 3827/0/239, the goodness-of-fit on F2 = 1.019. Final R indices for [I>2sigma(I)] were R1 = 0.0517, wR2 = 0.1115 and R indices (all data) R1 = 0.1007, wR2 = 0.1354. The largest electron density difference peak and hole were 0.254 and -0.244 electrons sup>-3, respectively. The two independent molecules A and B have essentially identical bond lengths and angles and are highly planar, with rms deviation for all 12 non-H atoms of 0.0292 for molecule A and 0.0592 for molecule B. The two molecules in the asymmetric unit are assembled parallel to each other within 1.58(4) with each of the six atoms of benzene ring A overlapping with one of the atoms in benzene ring B at a mean distance of 3.84(3) . The closest contacts between molecules A and B are C(12A)H---O(4B) = 3.521 and C(11B)H---O(4A) = 3.441 The crystal structure is formed by infinite sheets of these assemblies all lying parallel to the (1 0`1) plane. The presence of two independent molecules in the asymmetric unit provides an opportunity to examine the molecular geometry in detail by comparison. The benzene ring in both molecules A and B exhibits distortions as a result of the presence of the furan moiety. In particular, C(1)-C(6) = 1.369(2) in molecule A and 1.367(2) in molecule B are both significantly less than the average of the other 10 C-C bonds, 1.393(2), by about 12?. Other examples of crystal structures are discussed where this effect is observed.

References

  1. Spencer, J.; Mendham, A. P.; Kotha, A. K.; Richardson, S. C. W.; Hillard, E. A.; Jaouen, G.; Male, L.; Hursthouse, M. B., Structural and biological investigation of ferrocene-substituted 3-methylidene-1,3-dihydro-2H-indol-2-ones. Dalton Trans 2009, 918-921. http://dx.doi.org/10.1039/b816249b DOI: https://doi.org/10.1039/B816249B
  2. Spencer, J.; Chowdhry, B. Z.; Hamid, S.; Mendham, A. P.; Male, L.; Coles, S. J.; Hursthouse, M. B., Seven 3-methylidene-1H-indol-2(3H)-ones related to the multiple-receptor tyrosine kinase inhibitor sunitinib. Acta Cryst C 2010, 66, o71-o78. http://dx.doi.org/10.1107/S0108270109054134 DOI: https://doi.org/10.1107/S0108270109054134
  3. Visualizer, Discovery Studio, Release 3.5. Accelrys Inc, San Diego, CA, USA 2012.
  4. Barnes, C., ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI) by J. Farrugia. J Appl Cryst 1997, 30, 568. http://dx.doi.org/10.1107/S0021889897006638 DOI: https://doi.org/10.1107/S0021889897006638
  5. Merritt, E. A.; Bacon, D. J., Raster3D: Photorealistic molecular graphics. In Methods in Enzymology, Charles W. Carter Jr, R. M. S., Ed. Academic Press: 1997; Vol. Volume 277, pp 505-524. http://dx.doi.org/10.1016/S0076-6879(97)77028-9 DOI: https://doi.org/10.1016/S0076-6879(97)77028-9
  6. Ladd, M. F. C.; Palmer, R. A., Structure determination by X-ray crystallography. Springer: 1985. http://dx.doi.org/10.1007/978-1-4615-7936-6 DOI: https://doi.org/10.1007/978-1-4615-7936-6
  7. Visualizer, Discovery Studio, Release 4.0 Accelrys Inc, San Diego, CA, USA 2013.
  8. Brooks, B. R.; Bruccoleri, R. E.; Olafson, B. D.; States, D. J.; Swaminathan, S.; Karplus, M., CHARMM: A program for macromolecular energy, minimization, and dynamics calculations. J Comput Chem 1983, 4, 187-217. http://dx.doi.org/10.1002/jcc.540040211 DOI: https://doi.org/10.1002/jcc.540040211
  9. Momany, F. A.; Rone, R., Validation of the general purpose QUANTA 3.2/CHARMm force field. J Comput Chem 1992, 13, 888-900. http://dx.doi.org/10.1002/jcc.540130714 DOI: https://doi.org/10.1002/jcc.540130714
  10. Spek, A., PLATON, An Integrated Tool for the Analysis of the Results of a Single Crystal Structure Determination. Acta Cryst A 1990, 46, c34.
  11. Mackay, A., Quaternion transformation of molecular orientation. Acta Cryst A 1984, 40, 165-166. http://dx.doi.org/10.1107/S0108767384000362 DOI: https://doi.org/10.1107/S0108767384000362
  12. Choi, H. D.; Seo, P. J.; Son, B. W.; Lee, U., 5-Methyl-2,3-diphenyl-1-benzofuran. Acta Cryst E 2006, 62, o2335-o2336. http://dx.doi.org/10.1107/S1600536806039596 DOI: https://doi.org/10.1107/S1600536806017454
  13. Marelli, C.; Monti, C.; Galli, S.; Masciocchi, N.; Piarulli, U., 2-(2-Hydroxyaryl)cinnamic amides: a new class of axially chiral molecules. Tetrahedron 2006, 62, 8943-8951. http://dx.doi.org/10.1016/j.tet.2006.07.019 DOI: https://doi.org/10.1016/j.tet.2006.07.019
  14. Trost, B. M.; Cramer, N.; Silverman, S. M., Enantioselective Construction of Spirocyclic Oxindolic Cyclopentanes by Palladium-Catalyzed Trimethylenemethane-[3+2]-Cycloaddition. J Am Chem Soc 2007, 129, 12396-12397.
  15. http://dx.doi.org/10.1021/ja075335w DOI: https://doi.org/10.1021/ja075335w
  16. Duisenberg, A., Indexing in single-crystal diffractometry with an obstinate list of reflections. J Appl Cryst 1992, 25, 92-96. http://dx.doi.org/10.1107/S0021889891010634 DOI: https://doi.org/10.1107/S0021889891010634
  17. Hooft, R. W. W., Collect: Data collection software. Nonius BV, Delft, The Netherlands 1998.
  18. Otwinowski, Z.; Minor, W., Processing of X-ray diffraction data collected in oscillation mode. In Methods in Enzymology, Charles W. Carter, Jr., Ed. Academic Press: 1997; Vol. Volume 276, pp 307-326. http://dx.doi.org/10.1016/S0076-6879(97)76066-X DOI: https://doi.org/10.1016/S0076-6879(97)76066-X
  19. Blessing, R., An empirical correction for absorption anisotropy. Acta Cryst A 1995, 51, 33-38. http://dx.doi.org/10.1107/S0108767394005726 DOI: https://doi.org/10.1107/S0108767394005726
  20. Blessing, R., Outlier Treatment in Data Merging. J Appl Cryst 1997, 30, 421-426. http://dx.doi.org/10.1107/S0021889896014628 DOI: https://doi.org/10.1107/S0021889896014628
  21. Cosier, J.; Glazer, A. M., A nitrogen-gas-stream cryostat for general X-ray diffraction studies. J Appl Cryst 1986, 19, 105-107. http://dx.doi.org/10.1107/S0021889886089835 DOI: https://doi.org/10.1107/S0021889886089835
  22. Sheldrick, G., A short history of SHELX. Acta Cryst A 2008, 64, 112-122. http://dx.doi.org/10.1107/S0108767307043930 DOI: https://doi.org/10.1107/S0108767307043930
  23. Sheldrick, G. M., SHELXL-97, Release 97-2; University of Gttingen: Gttingen, Germany, 1997. 1997.
  24. Farrugia, L., WinGX suite for small-molecule single-crystal crystallography. J Appl Cryst 1999, 32, 837-838. http://dx.doi.org/10.1107/S0021889899006020 DOI: https://doi.org/10.1107/S0021889899006020
  25. Coles, S. J.; Gale, P. A., Changing and challenging times for service crystallography. Chem Sci 2012, 3, 683-689. http://dx.doi.org/10.1039/c2sc00955b DOI: https://doi.org/10.1039/C2SC00955B

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Palmer, R. A.; Spencer, J.; Mendham, A. P.; Chowdhry, B. Z.; Lisgarten, D. R.; Trost, B. M.; Cramer, N.; Male, L.; Coles, S. J. X-Ray Crystallographic Structure of 3-(Propan-2-Ylidene) Benzofuran-2(3H)-One. J Pharm Chem 2014, 1 (3), 43-49. https://doi.org/10.14805/jphchem.2014.art18.
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Received
July 20, 2014
Published
October 27, 2014
Section
Research Articles
Pages
43-49

Keywords

  • Knoevenagel condensation
  • X-ray crystal structure
  • molecular geometry