5′′-(4-Meth­oxy­benzyl­idene)-1′-(4-meth­oxy­phen­yl)-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/S1600536813001177

Volume 69
Part 2
Pages o256-o257
February 2013

Received 28 December 2012
Accepted 11 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.066
wR = 0.183
Data-to-parameter ratio = 13.6
Details

5''-(4-Methoxybenzylidene)-1'-(4-methoxyphenyl)-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 compound, C₃₉H₃₈N₂O₄, the pyridinone ring adopts a twisted half-chair conformation with the N atom deviating by 0.3304 (1) and with the methylene C atom adjacent to the octahydroindolizine unit deviating by 0.444 (3) Å from the mean plane defined by the other four atoms. In the octahydroindolizine system, the pyrrolidine ring exhibits an envelope conformation, with the fused methyne C atom deviating by 0.6315 (1) Å from the mean plane defined by the other four atoms, and the piperidine ring exhibits a distorted chair conformation, as reflected in the puckering parameters Q = 0.568 (4) Å, [theta] = 1.5 (4) and [varphi] = 161 (16)°. In the crystal pairs of weak C-HO interactions form centrosymmetric dimers, which are further connected by C-H [pi] interactions. The crystal studied was a non-merohedral twin, with a domain ratio of 0.91:0.09.

Related literature

For general properties of indolizines, see: Weidner et al. (1989); Katritzky et al. (1999); Asano et al. (2000); Gilchrist (2001); Sarkunam & Nallu (2005); Tielmann & Hoenke (2006); Oslund et al. (2008); Vemula et al. (2011); Singh & Mmatli (2011). For bond lengths and angles in a related structure, see: Suresh et al. (2011). For ring conformation analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₉H₃₈N₂O₄
M_r = 598.71
Monoclinic, P 2₁ /n
a = 8.379 (5) Å
b = 16.958 (5) Å
c = 22.063 (5) Å
= 96.605 (5)°
V = 3114 (2) Å³
Z = 4
Mo K radiation
= 0.08 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
5537 measured reflections
5537 independent reflections
3900 reflections with I > 2(I)

Refinement

R[F² > 2(F²)] = 0.066
wR(F²) = 0.183
S = 1.05
5537 reflections
407 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the benzene ring (C52-C57) in the phenylmethylidene group.

D-HA	D-H	HA	DA	D-HA
C77-H77AO2ⁱ	0.96	2.54	3.418 (5)	152
C58-H58CCg1ⁱⁱ	0.96	2.93	3.822 (5)	156
Symmetry codes: (i) -x+1, -y, -z; (ii) -x+2, -y, -z+1.

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: BH2471 ).

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

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organic compounds