5′′-(4-Chloro­benzyl­idene)-1′,1′′-dimethyl-3′-phenyl­acenaphthene-1-spiro-2′-pyrrolidine-3′-spiro-3′′-pyridine-2,4′′-dione

S Pandiarajan; S N Saravanamoorthy; B Ravi Kumar; R Ranjith Kumar; S Athimoolam

doi:10.1107/S1600536807059582

. 2007 Dec 6;64(Pt 1):o99–o100. doi: 10.1107/S1600536807059582

5′′-(4-Chlorobenzylidene)-1′,1′′-dimethyl-3′-phenylacenaphthene-1-spiro-2′-pyrrolidine-3′-spiro-3′′-pyridine-2,4′′-dione

S Pandiarajan ^a, S N Saravanamoorthy ^a, B Ravi Kumar ^a, R Ranjith Kumar ^b, S Athimoolam ^c,^*

PMCID: PMC2915053 PMID: 21200975

Abstract

In the title compound, C₃₄H₂₈Cl₂N₂O₂, the five-membered pyrrolidine ring adopts an envelope conformation and the six-membered piperidinone ring is in a distorted half-chair conformation. The molecular structure shows three intramolecular C—H⋯O interactions and the crystal packing is stabilized through intermolecular C—H⋯O and C—H⋯π interactions.

Related literature

For the biological importance of pyrrolidines, see: Babu & Raghunathan (2007 ▶); Boruah et al. (2007 ▶); Chande et al. (2005 ▶); Horri et al. (1986 ▶); Karthikeyan et al. (2007 ▶); Watson et al. (2001 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶). For hydrogen-bonding interactions, see: Desiraju & Steiner (1999 ▶).

Experimental

Crystal data

C₃₄H₂₈Cl₂N₂O₂
M _r = 567.48
Monoclinic,
a = 8.6561 (5) Å
b = 13.4732 (8) Å
c = 24.3962 (14) Å
β = 95.765 (12)°
V = 2830.8 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 293 (2) K
0.22 × 0.19 × 0.15 mm

Data collection

Nonius MACH3 diffractometer
Absorption correction: ψ scan (North et al., 1968 ▶) T _min = 0.963, T _max = 0.991
5802 measured reflections
4962 independent reflections
3252 reflections with I > 2σ(I)
R _int = 0.031
3 standard reflections frequency: 60 min intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.122
S = 1.01
4962 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.38 e Å⁻³

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS ; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXTL/PC (Bruker, 2000 ▶); program(s) used to refine structure: SHELXTL/PC; molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL/PC.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807059582/bt2624sup1.cif

e-64-00o99-sup1.cif^{(27.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807059582/bt2624Isup2.hkl

e-64-00o99-Isup2.hkl^{(238.1KB, hkl)}

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

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

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯O1	0.93	2.40	2.783 (3)	104
C14—H14⋯O1	0.98	2.44	2.818 (3)	102
C22—H22C⋯O2	0.96	2.56	3.101 (3)	116
C26—H26⋯O1ⁱ	0.93	2.38	3.307 (3)	176
C21—H21B⋯Cg1ⁱⁱ	0.97	2.73	3.559 (3)	144

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

SA sincerely thanks the Vice-Chancellor and Management of the Kalasalingam University, Anand Nagar and Krishnan Koil, for their support and encouragement. SPR and BRK thank the Principal and Management of Devanga Arts College, Aruppukottai.

supplementary crystallographic information

Comment

1,3-Dipolar cycloadditions form a subject of intensive research in organic synthesis in view of their great synthetic potential (Karthikeyan et al., 2007). In particular, the cycloaddition of nonstabilized azomethine ylides with olefins represents one of the most convergent approaches for the construction of pyrrolidines (Boruah et al., 2007), which are prevalent in a variety of biologically active compounds (Watson et al., 2001) and find utility in the treatment of diseases such as diabetes (Horri et al., 1986). Acenaphthenequinone is a versatile precursor for azomethine ylide cycloaddition as it reacts with various α-amino acids generating reactive 1,3-dipoles (Babu & Raghunathan, 2007). Synthesis of spiro compounds have drawn considerable attention of the chemists, in view of their very good antimycobacterial activity (Chande et al., 2005).

The envelope conformation of the five-membered ring in (I), is observed through the puckering analysis [q₂ = 0.446 (2) Å and φ₂ = 43.2 (3)°; Cremer & Pople, 1975] and the six-membered ring adopts distorted half-chair conformation [q₂ = 0.289 (3) Å, φ₂ = 117.1 (6)° and q₃ = -0.454 (2) Å] (Fig. 1). The dihedral angle between the chlorophenyl rings are 86.1 (1)° and these rings are making angles of 35.6 (1) and 51.7 (1)° with the acenaphthene group.

The molecular structure of the title compound shows three intramolecular hydrogen bonds (Desiraju & Steiner, 1999). The crystal packing is stabilized through intermolecular C—H···O and C—H···π interactions (Fig. 2; Table 1). Atom H21B interacts with the centroid of the ring C1–C6.

Experimental

A mixture of 1-methyl-3,5-bis[(E)-4-chlorophenylmethylidene]tetrahydro-4(1H)-pyridinone 1 mmol), acenaphthenequinone (1 mmol) and sarcosine (1 mmol) was dissolved in methanol (10 ml) and refluxed for 1 h. 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 1-Methyl-4-(4-chlorophenyl)pyrrolo-(spiro[2.2'']-acenaphthene-1'')- spiro[3.3']-5'-(4-chlorophenyl-methylidene)-1'-methyltetrahydro-4'-(1H)- pyridinone as pale yellow solid.