5′′-(4-Chloro­benzyl­idene)-1′-(4-chloro­phen­yl)-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.; Kumar, R.R.; Sivakumar, S.; Lakshman, P.L.N.

doi:10.1107/S160053681204545X

Volume 68
Part 12
Pages o3315-o3316
December 2012

Received 2 November 2012
Accepted 3 November 2012
Online 10 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.113
Data-to-parameter ratio = 18.8
Details

5''-(4-Chlorobenzylidene)-1'-(4-chlorophenyl)-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 R. Ranjith Kumar,^b S. Sivakumar ^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 compound, C₃₇H₃₂Cl₂N₂O₂, the pyridinone ring adopts a twisted half-chair conformation. The fused pyrrolidine and piperidine rings of the octahydroindolizine unit exhibit envelope (with the C atom bound to the C atom bearing the chlorobenzene ring being the flap atom) and chair conformations, respectively. The dihedral angle between the chlorobenzene rings is 84.03 (1)°. In the crystal, C-H [pi] interactions lead to supramolecular chains along [101] that assemble in the ac plane. Connections along the b axis are of the type ClCl [3.4065 (8) Å].

Related literature

For general properties of indolizines, see: Gundersen et al. (2007). For related structures, see: Sussman & Wodak (1973); Wodak (1975). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₇H₃₂Cl₂N₂O₂
M_r = 607.55
Monoclinic, P 2₁ /n
a = 14.1346 (5) Å
b = 15.2184 (6) Å
c = 14.5603 (6) Å
= 102.337 (1)°
V = 3059.7 (2) Å³
Z = 4
Mo K radiation
= 0.25 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
32144 measured reflections
7321 independent reflections
4492 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.113
S = 1.01
7321 reflections
389 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.38 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C52-C57 benzene ring.

D-HA	D-H	HA	DA	D-HA
C75-H75Cg1ⁱ	0.93	2.88	3.669 (2)	144
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: TK5167 ).

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.
Gundersen, L.-L., Charnock, C., Negussie, A. H., Rise, F. & Teklu, S. (2007). Eur. J. Pharm. Sci. 30, 26-35.
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