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

Lee, J.K.; Chavre, S.N.; Cho, Y.S.; Lee, Y.; Cha, J.H.

doi:10.1107/S1600536811051993

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 (C-C) = 0.004 Å
R = 0.051
wR = 0.139
Data-to-parameter ratio = 14.6
Details

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

Jae Kyun Lee,^a Satish N. Chavre,^a Yong Seo Cho,^a Yeonhee Lee ^b and Joo Hwan Cha ^b ^*

^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, 2008); Cohen et al. (2001); Shin et al. (2005).

Experimental

Crystal data

C₂₂H₂₁ClO₂
M_r = 352.86
Monoclinic, P 2₁ /n
a = 5.7575 (6) Å
b = 11.3547 (12) Å
c = 28.554 (3) Å
= 94.442 (8)°
V = 1861.1 (4) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.301, T_max = 0.684
18544 measured reflections
3363 independent reflections
2012 reflections with F² > 2(F²)
R_int = 0.073

Refinement

R[F² > 2(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
_max = 0.20 e Å^-3
_min = -0.19 e Å^-3

Data collection: RAPID-AUTO (Rigaku, 2006); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SIR2008 in Il Milione (Burla et al., 2007); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: CrystalStructure (Rigaku, 2010); 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.
Chavre, S. N., Choo, H., Cha, J. H., Pae, A. N., Choi, K. I. & Cho, Y. S. (2006). Org. Lett. 8, 3617-3619.
Chavre, S. N., Choo, H., Lee, J. K., Pae, A. N., Kim, Y. & Cho, Y. S. (2008). J. Org. Chem. 73, 7467-7471.
Cohen, F., MacMillan, D. W., Overman, L. E. & Romero, A. (2001). Org. Lett. 3, 1225-1228.
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.
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.

organic compounds