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Volume 69 
Part 2 
Pages o249-o250  
February 2013  

Received 3 December 2012
Accepted 21 December 2012
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.006 Å
R = 0.058
wR = 0.138
Data-to-parameter ratio = 7.3
Details
Open access

3''-(2-Fluorobenzylidene)-4'-(2-fluorophenyl)-1'-methyldispiro[acenaphthylene-1,2'-pyrrolidine-3',1''-cyclopentane]-2,2''-dione

aWenzhou Medical College, School of Pharmacy, Wenzhou 325035, People's Republic of China
Correspondence e-mail: proflxk@163.com

In the title compound, C33H25F2NO2, the acenaphthene ring system forms dihedral angles of 50.93 (14) and 36.89 (14)° with the benzene rings. The pyrrolidine and cyclopentanone rings adopt envelope (with the N atom as the flap) and twisted conformations, respectively. In the crystal, C-H...O and C-H...F interactions link the molecules.

Related literature

For related structures, see: Abdul Ajees et al. (2002[Abdul Ajees, A., Manikandan, S. & Raghunathan, R. (2002). Acta Cryst. E58, o802-o804.]); Usha et al. (2003[Usha, G., Selvanayagam, S., Yogavel, M., Velmurugan, D., Amalraj, A., Raghunathan, R., Shanmuga Sundara Raj, S. & Fun, H.-K. (2003). Acta Cryst. E59, o1572-o1574.]). For background to the biological properties of spiro-pyrrolidine derivatives, see: Chande et al. (2005[Chande, M. S., Verma, R. S., Barve, P. A. & Khanwelkar, R. R. (2005). Eur. J. Med. Chem. 40, 1143-1148.]); Dandia et al. (2003[Dandia, A., Sati, M., Arya, K., Sharma, R. & Loupy, A. (2003). Chem. Pharm. Bull. 51, 1137-1141.]); Cravotto et al. (2001[Cravotto, G., Giovenzana, G. B., Pilati, T., Sisti, M. & Palmisano, G. (2001). J. Org. Chem. 66, 8447-8453.]); Winfred et al. (2000[Winfred, G. B., Rutger, M. & Fieseler, F. (2000). J. Org. Chem. 65, 8317-8320.]); Metwally et al. (1998[Metwally, K. A., Dukat, M. & Egan, C. T. (1998). J. Med. Chem. 41, 5084-5093.]); Suenaga et al. (2001[Suenaga, K., Araki, K. & Sengoku, T. (2001). Org. Lett. 3, 527-529.]). For the synthesis of the title compound, see: Kumar et al. (2008a[Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2008a). Tetrahedron, 64, 2962-2971.],b[Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2008b). J. Med. Chem. 51, 5731-5735.]); Liang et al. (2009[Liang, G., Shao, L. L., Wang, Y., Zhao, C. G., Chu, Y. H., Xiao, J., Zhao, Y., Li, X. K. & Yang, S. L. (2009). Bioorg. Med. Chem. 17, 2623-2631.]).

[Scheme 1]

Experimental

Crystal data
  • C33H25F2NO2

  • Mr = 505.54

  • Orthorhombic, P c a 21

  • a = 17.728 (13) Å

  • b = 12.272 (9) Å

  • c = 12.094 (8) Å

  • V = 2631 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.45 × 0.38 × 0.27 mm

Data collection
  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.641, Tmax = 1.000

  • 12188 measured reflections

  • 2500 independent reflections

  • 2072 reflections with I > 2[sigma](I)

  • Rint = 0.123

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.126

  • S = 1.02

  • 2500 reflections

  • 344 parameters

  • 13 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.32 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3B...O1i 0.97 2.35 3.317 (5) 172
C14-H14A...F2ii 0.93 2.43 3.212 (7) 141
C25-H25...O2iii 0.93 2.58 3.458 (7) 158
Symmetry codes: (i) [-x+{\script{1\over 2}}, y, z-{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+1, z]; (iii) x, y-1, z.

Data collection: SMART (Bruker, 2002[Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2002[Bruker (2002). 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2458 ).


Acknowledgements

This work was supported by the Zhejiang Provincial Natural Science Foundation of China (grant Nos. LY12H16003 and Y4110197) and the Project of Wenzhou Science & Technology Bureau (Y20100273). The X-ray crystallographic facility at the Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, is gratefully acknowledged for the data collection.

References

Abdul Ajees, A., Manikandan, S. & Raghunathan, R. (2002). Acta Cryst. E58, o802-o804.  [CSD] [CrossRef] [details]
Bruker (2002). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chande, M. S., Verma, R. S., Barve, P. A. & Khanwelkar, R. R. (2005). Eur. J. Med. Chem. 40, 1143-1148.  [ISI] [CrossRef] [PubMed] [ChemPort]
Cravotto, G., Giovenzana, G. B., Pilati, T., Sisti, M. & Palmisano, G. (2001). J. Org. Chem. 66, 8447-8453.  [CSD] [CrossRef] [PubMed] [ChemPort]
Dandia, A., Sati, M., Arya, K., Sharma, R. & Loupy, A. (2003). Chem. Pharm. Bull. 51, 1137-1141.  [CrossRef] [PubMed] [ChemPort]
Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2008a). Tetrahedron, 64, 2962-2971.  [ISI] [CrossRef] [ChemPort]
Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2008b). J. Med. Chem. 51, 5731-5735.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Liang, G., Shao, L. L., Wang, Y., Zhao, C. G., Chu, Y. H., Xiao, J., Zhao, Y., Li, X. K. & Yang, S. L. (2009). Bioorg. Med. Chem. 17, 2623-2631.  [CrossRef] [PubMed] [ChemPort]
Metwally, K. A., Dukat, M. & Egan, C. T. (1998). J. Med. Chem. 41, 5084-5093.  [ISI] [CrossRef] [ChemPort] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Suenaga, K., Araki, K. & Sengoku, T. (2001). Org. Lett. 3, 527-529.  [ISI] [CrossRef] [PubMed] [ChemPort]
Usha, G., Selvanayagam, S., Yogavel, M., Velmurugan, D., Amalraj, A., Raghunathan, R., Shanmuga Sundara Raj, S. & Fun, H.-K. (2003). Acta Cryst. E59, o1572-o1574.  [CSD] [CrossRef] [details]
Winfred, G. B., Rutger, M. & Fieseler, F. (2000). J. Org. Chem. 65, 8317-8320.  [PubMed]


Acta Cryst (2013). E69, o249-o250   [ doi:10.1107/S1600536812051550 ]

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