3′-(4-Chloro­benzo­yl)-4′-(4-chloro­phen­yl)-1′-methyl­spiro­[indoline-3,2′-pyrrolidin]-2-one

T Srinivasan; S Suhitha; S Purushothaman; R Raghunathan; D Velmurugan

doi:10.1107/S1600536811044618

. 2011 Oct 29;67(Pt 11):o3128. doi: 10.1107/S1600536811044618

3′-(4-Chlorobenzoyl)-4′-(4-chlorophenyl)-1′-methylspiro[indoline-3,2′-pyrrolidin]-2-one

T Srinivasan ^a, S Suhitha ^a, S Purushothaman ^b, R Raghunathan ^b, D Velmurugan ^a,^*

PMCID: PMC3247512 PMID: 22220130

Abstract

In the title compound, C₂₅H₂₀Cl₂N₂O₂, the pyrrolidine ring adopts an envelope conformation and the best plane through the five ring atoms makes a dihedral angle of 87.03 (8)° with the indoline ring. Molecules are connected by pairs of N—H⋯O hydrogen bonds into centrosymmetric dimers with an R ₂ ²(8) graph-set ring motif. C—H⋯O hydrogen bonds stabilize the crystal structure.

Related literature

For substituted pyrrolidine compounds, see: Coldham & Hufton (2005 ▶). For graph-set notation of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₅H₂₀Cl₂N₂O₂
M _r = 451.33
Monoclinic,
a = 11.4139 (2) Å
b = 11.6957 (2) Å
c = 16.5262 (2) Å
β = 102.037 (1)°
V = 2157.64 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.33 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
20528 measured reflections
5426 independent reflections
3812 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.114
S = 1.03
5426 reflections
293 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.44 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811044618/bt5687sup1.cif

e-67-o3128-sup1.cif^{(23KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811044618/bt5687Isup2.hkl

e-67-o3128-Isup2.hkl^{(260.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811044618/bt5687Isup3.cml

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
N2—H2A⋯O2ⁱ	0.85 (2)	2.06 (2)	2.876 (2)	160
C24—H24⋯O1ⁱⁱ	0.93	2.42	3.104 (2)	130

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

Acknowledgments

TS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS also thanks the DST for an Inspire fellowship.

supplementary crystallographic information

Comment

Substituted pyrrolidine compounds are an important class of heterocyclic compounds with wide spread applications to the synthesis of biologically active compounds and natural products (Coldham & Hufton, 2005).

The indoline ring is essentially planar with a maximum deviation of 0.0594 (16)Å for atom C12. The oxygen atom O2 deviates with the value of 0.0566 (13)Å from the indoline ring. The phenyl ring of chlorophenyl group makes a dihedral angle of 79.68 (9)° and 20.47 (7)° with the pyrollidin ring and indoline ring system. The phenyl ring of chlorobenzaldehyde group makes a dihedral angle of 71.39 (9)° and 35.17 (8)° with the pyrrolidin ring and indoline ring system, respectively.

The pyrrolidin ring adopts an envelope conformation. The pyrrolidin ring makes a dihedral angle of 87.03 (8)° with the indoline ring system. The crystal structure is stabilized by C—H···O and N—H···O hydrogen bonds resulting in R²₂(16) and R²₂(8) graph-set ring motifs (Bernstein et al., 1995).

Experimental

A solution of (E)-1,3-bis(4-chlorophenyl)prop-2-en-1-one(2 mmol), isatin (1 eq.) and sarcosine( 1 eq.) was refluxed in dry toluene for 8 hrs at 110°C using Dean-Stark apparatus.After the completion of reaction as indicated by TLC,toluene was evaporated under reduced pressure.The crude product was purified by column chromatography using hexane: EtOAc (8:2) as eluent.