4′-(4-Methoxy­phen­yl)-1,1′,1′′-trimethyl­dispiro­[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidine]-2,2′′,5′′-trione

S Nirmala; K Karthikeyan; E Theboral Sugi Kamala; L Sudha; P T Perumal

doi:10.1107/S1600536809021114

. 2009 Jun 20;65(Pt 7):o1655–o1656. doi: 10.1107/S1600536809021114

4′-(4-Methoxyphenyl)-1,1′,1′′-trimethyldispiro[indoline-3,2′-pyrrolidine-3′,3′′-pyrrolidine]-2,2′′,5′′-trione

S Nirmala ^a, K Karthikeyan ^b, E Theboral Sugi Kamala ^a, L Sudha ^c,^*, P T Perumal ^b

PMCID: PMC2969413 PMID: 21582918

Abstract

In the title compound, C₂₄H₂₅N₃O₄, the pyrrolidine ring adopts an envelope conformation while the pyrrolidine-2′′,5′′-dione ring adopts a twist conformation. The indoline unit is planar [maximum deviation of −0.050 (9) Å] and forms a dihedral angle of 40.36 (4)° with the methoxyphenyl ring. Intramolecular C—H⋯O hydrogen bonds are observed. In the crystal, molecules are linked into a two-dimensional network parallel to the ab plane by intermolecular C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For the biological activity of spiro-pyrrolidine-containing compounds, see: Araki et al. (2002 ▶); Gore et al. (1991 ▶); James et al. (1991 ▶); Kobayashi et al. (1991 ▶); Tietze et al. (1988 ▶). For the biological activity of indole derivatives, see: Harris & Uhle (1960 ▶); Ho et al. (1986 ▶); Stevenson et al. (2000 ▶). For a related structure, see: Govind et al. (2003 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₄H₂₅N₃O₄
M _r = 419.47
Orthorhombic,
a = 11.2074 (3) Å
b = 11.2406 (3) Å
c = 33.6082 (9) Å
V = 4233.9 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.25 × 0.17 × 0.15 mm

Data collection

Bruker Kappa APEXII area-detector diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.978, T _max = 0.987
17736 measured reflections
5023 independent reflections
3269 reflections with I > 2σ(I)
R _int = 0.028

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.152
S = 1.07
5023 reflections
284 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 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: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809021114/ci2815sup1.cif

e-65-o1655-sup1.cif^{(24.5KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809021114/ci2815Isup2.hkl

e-65-o1655-Isup2.hkl^{(241.1KB, hkl)}

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2	0.93	2.52	3.122 (2)	123
C12—H12A⋯O1	0.97	2.58	3.222 (2)	124
C20—H20⋯O1	0.93	2.56	3.400 (2)	150
C12—H12B⋯O1ⁱ	0.97	2.56	3.264 (2)	129
C16—H16⋯O4ⁱⁱ	0.93	2.50	3.394 (2)	161
C19—H19⋯O2ⁱⁱⁱ	0.93	2.54	3.440 (2)	162
C21—H21C⋯Cg1^iv	0.96	2.93	3.592 (2)	127

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) . Cg1 is the centroid of the C15–C20 ring.

Acknowledgments

SN thanks Dr Babu Vargheese, SAIF, IIT Madras, India, for his help with the data collection. SN also thanks SRM management, India, for their support.

supplementary crystallographic information

Comment

Spiro compounds are a particular class of naturally occurring substances characterized by highly pronounced biological properties (Kobayashi et al., 1991; James et al., 1991). The spiro-pyrrolidine ring system is also found in phermones, antibiotics (Gore et al., 1991) and antitumour agents (Tietze et al., 1988; Araki et al., 2002).

Indole compounds can be used as bioactive drugs (Stevenson et al., 2000). Indole derivatives exhibit antiallergic, central nervous system depressant and muscle relaxant properties (Harris & Uhle, 1960; Ho et al., 1986). In view of this biological importance, the crystal structure of the title compound was determined and the results are presented here.

An ORTEP (Farrugia,1997) plot of the molecule is shown in Fig.1. The indole unit is planar, with a maximum deviation of -0.050 (9) Å for atom C1. The dihedral angle between the indole unit and the methoxyphenyl ring is 40.36 (4)°. The sum of angles at atoms N1 (360.0°) and N3 (359.9°) is in accordance with sp² hybridization, whereas the sum of angles at N2 (335.5°) is in accordance with sp³ hybridization. The N1—C5 and C5—O1 bond lengths show electron delocalization over atoms N1, C5 and O1. In the oxindole ring system, the variation in endocyclic angles are due to the fusion of the five- and six-membered rings (Govind et al., 2003). The methoxy group is almost coplanar with the C15-C20 benzene ring [C21—O4—C18—C17 = 174.7 (2)°]. The N2/C1-C4 pyrrolidine ring adopts an envelope conformation with puckering parameters q₂ and φ of 0.404 (2) Å and -38.8 (2)° respectively (Cremer & Pople, 1975). Atom N2 deviates by 0.590 Å from the least-squares plane through the remaining four atoms. The N3/C2/C12-C14 pyrrolidine ring adopts a twist conformation, with puckering parameters q₂ and φ of 0.233 (2) Å and -13.2 (4)° respectively (Cremer & Pople, 1975).

The molecular structure is stabilized by intramolecular C— H···O hydrogen bonds and the crystal packing is determined by intermolecular C—H···O hydrogen bonds and C—H···π interactions involving C15—C20 benzene rings (Table 1). In addition the packing is stabilized by van der Waals forces.

Experimental

A mixture of sarcosine (1 mmol), 1-methylisatin (1 mmol) and 3-(4-methoxybenzylidine)-1-methyl-pyrrolidine-2,5-dione (1 mmol) was refluxed in methanol. Completion of the reaction was evidenced by TLC analysis. The solvent was then removed in vacuo and the crude product subjected to column chromatography (100–200 mesh) using petroleum ether–ethyl acetate as eluent. Single crystals were obtained by crystallization from petroleum ether and ethyl acetate mixture.