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

Suresh, J.; Nagalakshmi, R.A.; Sivakumar, S.; Kumar, R.R.; Lakshman, P.L.N.

doi:10.1107/S1600536812051094

Volume 69
Part 1
Pages o140-o141
January 2013

Received 25 November 2012
Accepted 17 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.046
wR = 0.126
Data-to-parameter ratio = 19.4
Details

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

J. Suresh,^a R. A. Nagalakshmi,^a S. Sivakumar,^b R. Ranjith Kumar ^b and P. L. Nilantha Lakshman ^c ^*

^aDepartment of Physics, The 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 E isomer of the racemic compound, C₃₇H₃₂F₂N₂O₂, the pyridinone ring adopts a twisted half-chair conformation with the N atom deviating by -0.355 (3) Å and with the methylene C atom next to octahydroindolizine moiety deviating by 0.415 (3) Å from the mean plane defined by other four atoms. In the octahydroindolizine system, the pyrrolidine ring exhibits an envelope conformation with the fused methyne C atom deviating by 0.6496 (1) Å from the mean plane defined by four other atoms, and the piperidine ring exhibits a distorted chair conformation as evident from the puckering parameters Q = 0.568 (2) Å, [theta] = 1.0 (2) and [Phi] = 256 (11)°. In the crystal, C-HO interactions connect the molecules into chains along [101].

Related literature

For general properties of indolizines, see: Malonne et al. (1998); Medda et al. (2003); Pearson & Guo (2001). For related structures, see: Sussman & Wodak (1973); Wodak (1975). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₇H₃₂F₂N₂O₂
M_r = 574.65
Monoclinic, P 2₁ /n
a = 10.2716 (4) Å
b = 20.0353 (7) Å
c = 14.3790 (6) Å
= 97.047 (1)°
V = 2936.8 (2) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 293 K
0.21 × 0.19 × 0.18 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.967, T_max = 0.974
33177 measured reflections
7519 independent reflections
4823 reflections with I > 2(I)
R_int = 0.033

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.126
S = 1.01
7519 reflections
388 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C11-H11AO1ⁱ	0.97	2.49	3.352 (2)	148
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2088 ).

Acknowledgements

JS and RAN thank the management of Madura College for their encouragement and support. RRK thanks the DST, New Delhi, for funds under the fast-track scheme (grant No. SR/FT/CS-073/2009).

References

Bruker (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Malonne, H., Hanuise, J. & Fontaine, J. (1998). Pharm. Pharmacol. Commun. 4, 241-243.
Medda, S., Jaisankar, P., Manna, R. K., Pal, B., Giri, V. S. & Basu, M. K. (2003). J. Drug Target. 11, 123-128.
Pearson, W. H. & Guo, L. (2001). Tetrahedron Lett. 42, 8267-8271.
Sheldrick, G. M. (1996). SADABS, University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sussman, J. L. & Wodak, S. J. (1973). Acta Cryst. B29, 2918-2926.
Wodak, S. J. (1975). Acta Cryst. B31, 569-573.

organic compounds