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Volume 69 
Part 8 
Pages o1291-o1292  
August 2013  

Received 10 July 2013
Accepted 15 July 2013
Online 20 July 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.052
wR = 0.146
Data-to-parameter ratio = 13.9
Details
Open access

5''-(2-Fluorobenzylidene)-1'-(2-fluorophenyl)-1''-methyl-1',2',3',5',6',7',8',8a'-octahydrodispiro[acenaphthylene-1,3'-indolizine-2',3''-piperidine]-2,4''(1H)-dione

aDepartment of Physics, Madura College, Madurai 625 011, India,bDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and cDepartment of Food Science and Technology, University of Ruhuna, Mapalana, Kamburupitiya 81100, Sri Lanka
Correspondence e-mail: plakshmannilantha@ymail.com

In the title compound, C37H32F2N2O2, the central six-membered piperidine ring adopts a twisted half-chair conformation, with the N and methylene C atoms deviating by -0.2875 (16) and 0.4965 (15) Å, respectively, from the mean plane defined by the other four atoms. The piperidine connected to the octahydroindolizine ring is in a half-chair conformation. The five-membered pyrrole ring adopts a slightly twisted envelope conformation with the piperidine C atom as the flap atom. The F and H atoms of both fluorobenzene rings are disordered, with occupancy factors of 0.941 (3):0.059 (3) and 0.863 (3):0.137 (3). The molecular structure features some intramolecular C-H...O interactions. In the crystal, a supramolecular zigzag chain sustained by C-H...F interactions parallel to the c axis is formed, generating a C(12) graph-set motif.

Related literature

For indolizine derivatives, see: Medda et al. (2003[Medda, S., Jaisankar, P., Manna, R. K., Pal, B., Giri, V. S. & Basu, M. K. (2003). J. Drug Target. 11, 123-128.]). For background to spiro compounds, see: Caramella & Grunanger (1984[Caramella, P. & Grunanger, P. (1984). 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, edited by A. Padwa, pp. 291-312. New York: Wiley]); James et al. (1991[James, D., Kunze, H. B. & Faulkner, D. (1991). J. Nat. Prod. 54, 1137-1140.]); Kobayashi et al. (1991[Kobayashi, J., Tsuda, M., Agemi, K., Shigemori, H., Ishibashi, M., Sasaki, T. & Mikamiy, Y. (1991). Tetrahedron, 47, 6617-6622.]). For related structures, see: Sussman & Wodak (1973[Sussman, J. L. & Wodak, S. J. (1973). Acta Cryst. B29, 2918-2926.]); Wodak (1975[Wodak, S. J. (1975). Acta Cryst. B31, 569-573.]). For ring conformation analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C37H32F2N2O2

  • Mr = 574.65

  • Monoclinic, P 21 /c

  • a = 8.5161 (3) Å

  • b = 16.8176 (6) Å

  • c = 20.5195 (6) Å

  • [beta] = 99.845 (2)°

  • V = 2895.53 (17) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.30 × 0.30 × 0.25 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.974, Tmax = 0.978

  • 27283 measured reflections

  • 5702 independent reflections

  • 4231 reflections with I > 2[sigma](I)

  • Rint = 0.033

Refinement
  • R[F2 > 2[sigma](F2)] = 0.052

  • wR(F2) = 0.146

  • S = 1.02

  • 5702 reflections

  • 409 parameters

  • 23 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.70 e Å-3

  • [Delta][rho]min = -0.45 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C6-H6A...O2 0.97 2.35 2.930 (3) 118
C7-H7...O1 0.98 2.31 2.823 (2) 112
C22-H22...O1 0.93 2.58 3.146 (3) 120
C10-H10B...F1i 0.97 2.53 3.102 (3) 118
Symmetry code: (i) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker (2004). APEX2 and SAINT. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5239 ).


Acknowledgements

JS and RV thank the management of Madura College for their encouragement and support. RRK thanks DST, New Delhi, for funds under the Fast Track Scheme (Grant No. SR/FT/CS-073/2009). RV thanks Dr R. Jagan of IIT, Madras, for his help with the data collection and solving the structure.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Caramella, P. & Grunanger, P. (1984). 1,3-Dipolar Cycloaddition Chemistry, Vol. 1, edited by A. Padwa, pp. 291-312. New York: Wiley
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
James, D., Kunze, H. B. & Faulkner, D. (1991). J. Nat. Prod. 54, 1137-1140.  [CrossRef] [PubMed] [ChemPort] [Web of Science]
Kobayashi, J., Tsuda, M., Agemi, K., Shigemori, H., Ishibashi, M., Sasaki, T. & Mikamiy, Y. (1991). Tetrahedron, 47, 6617-6622.  [CrossRef] [ChemPort] [Web of Science]
Medda, S., Jaisankar, P., Manna, R. K., Pal, B., Giri, V. S. & Basu, M. K. (2003). J. Drug Target. 11, 123-128.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sussman, J. L. & Wodak, S. J. (1973). Acta Cryst. B29, 2918-2926.  [CrossRef] [ChemPort] [IUCr Journals] [Web of Science]
Wodak, S. J. (1975). Acta Cryst. B31, 569-573.  [CrossRef] [IUCr Journals] [Web of Science]


Acta Cryst (2013). E69, o1291-o1292   [ doi:10.1107/S1600536813019594 ]

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