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

Chen, G.-Z.; Wei, X.-Y.; Wang, Y.; Ren, L.-Q.; Li, X.-K.

doi:10.1107/S1600536812051550

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 (C-C) = 0.006 Å
R = 0.058
wR = 0.138
Data-to-parameter ratio = 7.3
Details

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

Gao-Zhi Chen,^a Xiao-Yan Wei,^a Yi Wang,^a Lu-Qing Ren ^a and Xiao-Kun Li ^a ^*

^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-HO and C-HF interactions link the molecules.

Related literature

For related structures, see: Abdul Ajees et al. (2002); Usha et al. (2003). For background to the biological properties of spiro-pyrrolidine derivatives, see: Chande et al. (2005); Dandia et al. (2003); Cravotto et al. (2001); Winfred et al. (2000); Metwally et al. (1998); Suenaga et al. (2001). For the synthesis of the title compound, see: Kumar et al. (2008a,b); Liang et al. (2009).

Experimental

Crystal data

C₃₃H₂₅F₂NO₂
M_r = 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 radiation
= 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) T_min = 0.641, T_max = 1.000
12188 measured reflections
2500 independent reflections
2072 reflections with I > 2(I)
R_int = 0.123

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.126
S = 1.02
2500 reflections
344 parameters
13 restraints
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.32 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3BO1ⁱ	0.97	2.35	3.317 (5)	172
C14-H14AF2ⁱⁱ	0.93	2.43	3.212 (7)	141
C25-H25O2ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
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.
Cravotto, G., Giovenzana, G. B., Pilati, T., Sisti, M. & Palmisano, G. (2001). J. Org. Chem. 66, 8447-8453.
Dandia, A., Sati, M., Arya, K., Sharma, R. & Loupy, A. (2003). Chem. Pharm. Bull. 51, 1137-1141.
Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2008a). Tetrahedron, 64, 2962-2971.
Kumar, R. R., Perumal, S., Senthilkumar, P., Yogeeswari, P. & Sriram, D. (2008b). J. Med. Chem. 51, 5731-5735.
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.
Metwally, K. A., Dukat, M. & Egan, C. T. (1998). J. Med. Chem. 41, 5084-5093.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Suenaga, K., Araki, K. & Sengoku, T. (2001). Org. Lett. 3, 527-529.
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.
Winfred, G. B., Rutger, M. & Fieseler, F. (2000). J. Org. Chem. 65, 8317-8320.

organic compounds