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Volume 66 
Part 1 
Page o56  
January 2010  

Received 15 November 2009
Accepted 28 November 2009
Online 4 December 2009

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Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.005 Å
R = 0.062
wR = 0.186
Data-to-parameter ratio = 14.5
Details
Open access

4-(4-Chlorophenyl)-7,7-dimethyl-7,8-dihydro-4H-1-benzopyran-2,5(3H,6H)-dione

Hao Shia*

aThe College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
Correspondence e-mail: shihao@zjut.edu.cn

The title compound, C17H17ClO3, has been synthesized by the reaction of p-chlorobenzaldehyde, isopropylidene malonate and 5,5-dimethylcyclohexane-1,3-dione with triethylbenzylammonium chloride in water as a green solvent. The six membered pyranone ring of the hexahydrocoumarin system has a screw-boat conformation while the dimethylcyclohexenone system has a distorted envelope conformation. The dihedral angle between the least-squares planes of the coumarin ring system and the benzene ring is 85.64 (9)°.

Related literature

For applications of coumarin derivatives, see: Wang et al. (1999[Wang, X. F., Qu, Y. & Gu, F. (1999). Speciality Petrochemicals, 1, 49-52.]); Yang (2001[Yang, J. S. (2001). West China J. Pharm. Sci. 16, 285-288.]). For related structures, see: Itoh & Kanemasa (2003[Itoh, K. & Kanemasa, S. (2003). Tetrahedron Lett. 44, 1799-1802.]); Itoh et al. (2005[Itoh, K., Hasegawa, M., Tanaka, J. & Kanemasa, S. (2005). Org. Lett. 7, 979-981.]). For ring puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C17H17ClO3

  • Mr = 304.76

  • Monoclinic, P 21 /n

  • a = 11.9005 (12) Å

  • b = 5.7971 (8) Å

  • c = 22.608 (2) Å

  • [beta] = 93.972 (1)°

  • V = 1555.9 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.25 mm-1

  • T = 298 K

  • 0.48 × 0.39 × 0.34 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1999[Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.889, Tmax = 0.919

  • 7519 measured reflections

  • 2789 independent reflections

  • 1585 reflections with I > 2[sigma](I)

  • Rint = 0.034
Refinement

  • R[F2 > 2[sigma](F2)] = 0.062

  • wR(F2) = 0.186

  • S = 1.05

  • 2789 reflections

  • 192 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.51 e Å-3

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 (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: BH2260 ).

Acknowledgements

The research was supported by the Open Foundation of Key Disciplines within the Zhejiang Provincial Key Disciplines.

References

Bruker (1999). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Itoh, K., Hasegawa, M., Tanaka, J. & Kanemasa, S. (2005). Org. Lett. 7, 979-981.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Itoh, K. & Kanemasa, S. (2003). Tetrahedron Lett. 44, 1799-1802.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, X. F., Qu, Y. & Gu, F. (1999). Speciality Petrochemicals, 1, 49-52.
Yang, J. S. (2001). West China J. Pharm. Sci. 16, 285-288.  [ChemPort]

Acta Cryst (2010). E66, o56  [ doi:10.1107/S1600536809051320 ]

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