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Volume 68 
Part 1 
Page o45  
January 2012  

Received 23 November 2011
Accepted 2 December 2011
Online 7 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.051
wR = 0.139
Data-to-parameter ratio = 14.6
Details
Open access

[2-(4-Chlorophenyl)-5-phenyloxolan-3-yl](cyclopentenyl)methanone

aCenter for Neuro-Medicine, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea, and bAdvanced Analysis Center, Korea Institute of Science & Technology, Hwarangro 14-gil, Seongbuk-gu, Seoul 136-791, Republic of Korea
Correspondence e-mail: jhcha@kist.re.kr

In the title compound, C22H21ClO2, the oxolane ring adopts a twisted conformation. The dihedral angles between the mean plane of the oxolane ring and the mean planes of the 4-chlorophenyl, phenyl and cyclopentenyl rings are 71.81 (18), 76.9 (18) and 82.08 (18)°, respectively.

Related literature

For general background to the Prins-type cyclization for the synthesis of oxolanes, see: Chavre et al. (2006[Chavre, S. N., Choo, H., Cha, J. H., Pae, A. N., Choi, K. I. & Cho, Y. S. (2006). Org. Lett. 8, 3617-3619.], 2008[Chavre, S. N., Choo, H., Lee, J. K., Pae, A. N., Kim, Y. & Cho, Y. S. (2008). J. Org. Chem. 73, 7467-7471.]); Cohen et al. (2001[Cohen, F., MacMillan, D. W., Overman, L. E. & Romero, A. (2001). Org. Lett. 3, 1225-1228.]); Shin et al. (2005[Shin, C., Chavre, S. N., Pae, A. N., Cha, J. H., Koh, H. Y., Chang, M. H., Choi, J. H. & Cho, Y. S. (2005). Org. Lett. 7, 3283-3285.]).

[Scheme 1]

Experimental

Crystal data
  • C22H21ClO2

  • Mr = 352.86

  • Monoclinic, P 21 /n

  • a = 5.7575 (6) Å

  • b = 11.3547 (12) Å

  • c = 28.554 (3) Å

  • [beta] = 94.442 (8)°

  • V = 1861.1 (4) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 1.90 mm-1

  • T = 296 K

  • 0.50 × 0.20 × 0.20 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan (ABSCOR; Rigaku, 1995[Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.301, Tmax = 0.684

  • 18544 measured reflections

  • 3363 independent reflections

  • 2012 reflections with F2 > 2[sigma](F2)

  • Rint = 0.073

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.139

  • S = 1.05

  • 3363 reflections

  • 230 parameters

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

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Data collection: RAPID-AUTO (Rigaku, 2006[Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2008 in Il Milione (Burla et al., 2007[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: CrystalStructure (Rigaku, 2010[Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.]); software used to prepare material for publication: CrystalStructure.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GO2037 ).


Acknowledgements

Fiancial support from the Korea Institute of Science and Technology (KIST) is gratefully acknowledged.

References

Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G., Siliqi, D. & Spagna, R. (2007). J. Appl. Cryst. 40, 609-613.  [ISI] [CrossRef] [ChemPort] [details]
Chavre, S. N., Choo, H., Cha, J. H., Pae, A. N., Choi, K. I. & Cho, Y. S. (2006). Org. Lett. 8, 3617-3619.  [ISI] [CrossRef] [PubMed] [ChemPort]
Chavre, S. N., Choo, H., Lee, J. K., Pae, A. N., Kim, Y. & Cho, Y. S. (2008). J. Org. Chem. 73, 7467-7471.  [CSD] [CrossRef] [PubMed] [ChemPort]
Cohen, F., MacMillan, D. W., Overman, L. E. & Romero, A. (2001). Org. Lett. 3, 1225-1228.  [ISI] [CrossRef] [PubMed] [ChemPort]
Rigaku (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Rigaku (2006). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku (2010). CrystalStructure. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Shin, C., Chavre, S. N., Pae, A. N., Cha, J. H., Koh, H. Y., Chang, M. H., Choi, J. H. & Cho, Y. S. (2005). Org. Lett. 7, 3283-3285.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2012). E68, o45  [ doi:10.1107/S1600536811051993 ]

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