5′′-(2,4-Dichloro­benzyl­idene)-1′-(2,4-dichloro­phen­yl)-1′′-methyl-1′,2′,3′,5′,6′,7′,8′,8a’-octa­hydro­dispiro­[acenaphthyl­ene-1,3′-indolizine-2′,3′′-piperidine]-2,4′′(1H)-dione

J Suresh; R Vishnupriya; R Ranjith Kumar; S Sivakumar; P L Nilantha Lakshman

doi:10.1107/S1600536812037956

. 2012 Sep 8;68(Pt 10):o2906. doi: 10.1107/S1600536812037956

5′′-(2,4-Dichlorobenzylidene)-1′-(2,4-dichlorophenyl)-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 Vishnupriya ^a, R Ranjith Kumar ^b, S Sivakumar ^b, P L Nilantha Lakshman ^c,^*

PMCID: PMC3470255 PMID: 23125699

Abstract

In the title compound, C₃₇H₃₀Cl₄N₂O₂, the pyridinone ring adopts a twisted half-chair conformation. In the octahydroindolizine fused-ring system, the piperidine ring is in a chair conformation and the pyrrole ring is twisted about the C—N bond linking the five- and six-membered rings. The molecular structure features an intramolecular C—H⋯O interaction and the crystal packing is stabilized by C—H⋯π interactions.

Related literature

For the importance of spiro compounds, see: Biava et al. (2006 ▶); Chande et al. (2005 ▶); Dandia et al. (2003 ▶); Shaharyar et al. (2006 ▶); Sriram et al. (2006 ▶). For related acenaphthylene structures, see: Hazell & Hazell (1977 ▶); Hazell & Weigelt (1976 ▶); Jones et al. (1992 ▶); Sundar et al. (2002 ▶).

Experimental

Crystal data

C₃₇H₃₀Cl₄N₂O₂
M _r = 676.43
Monoclinic,
a = 8.5695 (2) Å
b = 16.1634 (5) Å
c = 23.8325 (7) Å
β = 92.399 (2)°
V = 3298.20 (16) Å³
Z = 4
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 293 K
0.23 × 0.21 × 0.19 mm

Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.967, T _max = 0.974
29915 measured reflections
5750 independent reflections
4518 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.105
S = 1.08
5750 reflections
407 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.55 e Å⁻³

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 Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812037956/tk5147sup1.cif

e-68-o2906-sup1.cif^{(29.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037956/tk5147Isup2.hkl

e-68-o2906-Isup2.hkl^{(281.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C32–C37 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2	0.98	2.50	3.122 (3)	121
C10—H10a⋯Cg1ⁱ	0.97	2.68	3.5969	158

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

In general, spiro compounds and nitrogen heterocycles display good anti-mycobacterial activities (Chande et al., 2005; Dandia et al., 2003; Sriram et al., 2006; Biava et al., 2006; Shaharyar et al., 2006) . It is also pertinent to note that the synthesis of biologically active indolizine derivatives continues to attract the attention of organic chemists, because of their wide spectrum of biological activity.

In the title compound (Fig. 1) the pyridinone ring adopts twisted half-chair conformation with atoms N1 and C5 deviating by -0.638 (2) and -0.465 (2) Å, respectively, from the least-squares plane defined by the other atoms (C2/C3/C4/C6). Within the octahydroindolizine fused ring system, the piperidine ring is in a chair conformation and the pyrrole ring is twisted about the N2—C8 bond. The C—C bond lengths and C—C—C angles in the acenaphthylene group compare with those of related structures (Hazell & Hazell, 1977; Hazell & Weigelt, 1976; Jones et al., 1992; Sundar et al., 2002). The observed conformation of the pyrrole ring may be due to the presence of an intramolecular C8—H8···O2 interaction (Table 1). The dihedral angle between the dichlorobenzene rings is 67.2 (1)° and these rings form angles of 46.8 (1) and 68.6 (1)° with the acenaphthene group, respectively. The sum of the bond angles at N2 of the pyrrole ring is 337.78°, indicating sp³-hybridization.

A weak C—H···π interaction (Table 1) viz., C10—H10···Cg1 is observed (Cg1 is the centroid of the ring C32—C37).

Experimental

A mixture of 1-methyl-3,5-bis[(E)-2,4-dichloro phenylmethylidene]tetrahydro-4(1H)-pyridinone (1 mmol), acenaphthenequinone (1 mmol) and piperidine-2-carboxylic acid (1 mmol) was dissolved in isopropyl alcohol (15 ml) and heated to reflux for 60 min. After completion of the reaction as evident from TLC, the mixture was poured into water (50 ml), the precipitated solid was filtered and washed with water (100 ml) to obtain pure yellow solid. The product was recrystallized from ethyl acetate to obtain suitable crystals of (I) for X-ray analysis having a melting point of 480 K (Yield: 96%).