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Volume 68 
Part 2 
Pages o310-o311  
February 2012  

Received 7 December 2011
Accepted 22 December 2011
Online 11 January 2012

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Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.004 Å
R = 0.061
wR = 0.125
Data-to-parameter ratio = 13.0
Details
Open access

(3-Chlorophenyl){2-ethoxy-5-[(Z)-hydroxy(phenyl)methylidene]cyclopenta-1,3-dien-1-yl}methanone

Mihaela-Liliana Tintas,a Richard A. Varga,b Ion Grosua and Elena Bogdana*

aOrganic Chemistry Department, Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos 11, 400028, Cluj Napoca, Romania, and bInorganic Chemistry Department, Faculty of Chemistry and Chemical Engineering, Babes-Bolyai University, Arany Janos 11, 400028, Cluj Napoca, Romania
Correspondence e-mail: ebogdan@chem.ubbcluj.ro

The title compound, C21H17ClO3, which crystallizes as one of two possible oxo/hydroxy-fulvene prototropic tautomers, possesses a strong intramolecular O-H...O hydrogen bond that closes a seven-membered ring. The dihedral angles between the central five-membered ring and two pendant rings are 55.05 (9) and 44.51 (10)°. The crystal packing is characterized by weak intermolecular C-H...O interactions between an H atom of the oxymethylene unit and the carbonyl group of an adjacent molecule, resulting in formation of chains of molecules along the a axis.

Related literature

For the structures of related 2-acyl-6-hydoxyfulvene derivatives, see: Ferguson et al. (1975[Ferguson, G., Marsh, W. C., Restivo, R. J. & Lloyd, D. (1975). J. Chem. Soc. Perkin Trans. 2, pp. 998-1004.]); Dong et al. (2004[Dong, Y.-B., Wang, P. & Huang, R.-Q. (2004). Inorg. Chem. 43, 4727-4739.], 2006[Dong, Y.-B., Geng, Y., Ma, J.-P. & Huang, R.-Q. (2006). Organometallics, 25, 447-462.]). For more information on the synthesis of 2-acyl-6-hydoxyfulvene derivatives, see: Dong et al. (2004[Dong, Y.-B., Wang, P. & Huang, R.-Q. (2004). Inorg. Chem. 43, 4727-4739.], 2006[Dong, Y.-B., Geng, Y., Ma, J.-P. & Huang, R.-Q. (2006). Organometallics, 25, 447-462.]). For preparation details, see: Christl et al. (1998[Christl, M., Bien, N., Bodenschatz, G., Feineis, E., Hegmann, J., Hofmann, C., Mertelmeyer, S., Ostheimer, J., Sammtleben, F., Wehner, S., Peters, E.-M., Peters, K., Pfeiffer, M. & Stalke, D. (1998). Chem. Commun. pp. 2387-2389.]). For compounds obtained from 2-acyl-6-hydoxyfulvenes, see: Dong et al. (2004[Dong, Y.-B., Wang, P. & Huang, R.-Q. (2004). Inorg. Chem. 43, 4727-4739.]); Li et al. (2008[Li, J., Ma, J.-P., Liu, F., Wu, X.-W., Dong, Y.-B. & Huang, R.-Q. (2008). Organometallics, 27, 5446-5452.]); Snyder et al. (2005[Snyder, C. A., Selegue, J. P., Tice, N. C., Wallace, C. E., Blankenbuehler, M. T., Parkin, S., Allen, K. D. E. & Beck, R. T. (2005). J. Am. Chem. Soc. 127, 15010-15011.]). For complexes based on 2-acyl-6-hydoxyfulvenes, see: Dong et al. (2004[Dong, Y.-B., Wang, P. & Huang, R.-Q. (2004). Inorg. Chem. 43, 4727-4739.], 2006[Dong, Y.-B., Geng, Y., Ma, J.-P. & Huang, R.-Q. (2006). Organometallics, 25, 447-462.]); Wang et al. (2005[Wang, P., Dong, Y.-B., Ma, J.-P., Huang, R.-Q. & Smith, M. S. (2005). Cryst. Growth Des. 5, 701-706.]). For their various applications, see: Hong et al. (2005[Hong, B.-C., Chen, F.-L., Chen, S.-H., Liao, J.-H. & Lee, G.-H. (2005). Org. Lett. 7, 557-560.]); Kondo et al. (1992[Kondo, K., Goda, H., Takemoto, K., Aso, H., Sasaki, T., Kawakami, K., Yoshida, H. & Yoshida, K. (1992). J. Mater. Chem. 2, 1097-1102.]); Vicente et al. (1995[Vicente, J., Abad, J., Gil-Rubio, J. & Jones, P. G. (1995). Organometallics, 14, 2677-2688.]).

[Scheme 1]

Experimental

Crystal data

  • C21H17ClO3

  • Mr = 352.80

  • Monoclinic, P 21 /c

  • a = 8.1369 (16) Å

  • b = 27.737 (6) Å

  • c = 7.6709 (15) Å

  • [beta] = 98.51 (3)°

  • V = 1712.2 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.24 mm-1

  • T = 297 K

  • 0.30 × 0.29 × 0.26 mm
Data collection

  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.932, Tmax = 0.940

  • 15678 measured reflections

  • 3002 independent reflections

  • 2683 reflections with I > 2[sigma](I)

  • Rint = 0.040
Refinement

  • R[F2 > 2[sigma](F2)] = 0.061

  • wR(F2) = 0.125

  • S = 1.17

  • 3002 reflections

  • 231 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.22 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2 1.07 (5) 1.38 (5) 2.435 (3) 168 (5)
C20-H20B...O2i 0.97 2.51 3.246 (3) 133
Symmetry code: (i) x-1, y, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2000[Bruker (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: DIAMOND (Brandenburg & Putz, 2006[Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2041 ).

Acknowledgements

This work was supported by the CNCS-UEFISCDI, project No. PN II_IDEI_2278/2008.

References

Brandenburg, K. & Putz, H. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2000). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Christl, M., Bien, N., Bodenschatz, G., Feineis, E., Hegmann, J., Hofmann, C., Mertelmeyer, S., Ostheimer, J., Sammtleben, F., Wehner, S., Peters, E.-M., Peters, K., Pfeiffer, M. & Stalke, D. (1998). Chem. Commun. pp. 2387-2389.  [CSD] [CrossRef]
Dong, Y.-B., Geng, Y., Ma, J.-P. & Huang, R.-Q. (2006). Organometallics, 25, 447-462.  [CSD] [CrossRef] [ChemPort]
Dong, Y.-B., Wang, P. & Huang, R.-Q. (2004). Inorg. Chem. 43, 4727-4739.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Ferguson, G., Marsh, W. C., Restivo, R. J. & Lloyd, D. (1975). J. Chem. Soc. Perkin Trans. 2, pp. 998-1004.
Hong, B.-C., Chen, F.-L., Chen, S.-H., Liao, J.-H. & Lee, G.-H. (2005). Org. Lett. 7, 557-560.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Kondo, K., Goda, H., Takemoto, K., Aso, H., Sasaki, T., Kawakami, K., Yoshida, H. & Yoshida, K. (1992). J. Mater. Chem. 2, 1097-1102.  [CrossRef] [ChemPort] [ISI]
Li, J., Ma, J.-P., Liu, F., Wu, X.-W., Dong, Y.-B. & Huang, R.-Q. (2008). Organometallics, 27, 5446-5452.  [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Snyder, C. A., Selegue, J. P., Tice, N. C., Wallace, C. E., Blankenbuehler, M. T., Parkin, S., Allen, K. D. E. & Beck, R. T. (2005). J. Am. Chem. Soc. 127, 15010-15011.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Vicente, J., Abad, J., Gil-Rubio, J. & Jones, P. G. (1995). Organometallics, 14, 2677-2688.  [CrossRef] [ChemPort]
Wang, P., Dong, Y.-B., Ma, J.-P., Huang, R.-Q. & Smith, M. S. (2005). Cryst. Growth Des. 5, 701-706.  [CSD] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]

Acta Cryst (2012). E68, o310-o311   [ doi:10.1107/S1600536811055279 ]

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