4′-(2,4-Dichloro­phen­yl)-1,1′-dimethyl­piperidine-3-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-4,2′′-dione

S Nagamuthu; R Sribala; R Ranjithkumar; R V Krishnakumar; N Srinivasan

doi:10.1107/S160053681000704X

. 2010 Feb 27;66(Pt 3):o717. doi: 10.1107/S160053681000704X

4′-(2,4-Dichlorophenyl)-1,1′-dimethylpiperidine-3-spiro-3′-pyrrolidine-2′-spiro-3′′-indoline-4,2′′-dione

S Nagamuthu ^a, R Sribala ^a, R Ranjithkumar ^b, R V Krishnakumar ^a, N Srinivasan ^a,^*

PMCID: PMC2983500 PMID: 21580454

Abstract

In the title compound, C₂₃H₂₃Cl₂N₃O₂, the pyrroline ring adopts an envelope conformation and the piperidinone ring assumes a slightly twisted chair form. In the crystal, inversion dimers linked by pairs of N—H⋯O hydrogen bonds generate an R ₂ ⁸ graph-set motif and a short Cl⋯Cl contact of 3.478 (1) Å occurs.

Related literature

For the effect on halogens on the conformations of organic molecules, see: Awwadi et al. (2006 ▶). For the biological properties of pyrroles, see: Watson et al. (2001 ▶). For graph-set notation, see: Etter et al. (1990 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₃H₂₃Cl₂N₃O₂
M _r = 444.34
Triclinic,
a = 7.9398 (2) Å
b = 10.8747 (3) Å
c = 13.5367 (4) Å
α = 66.561 (2)°
β = 77.873 (1)°
γ = 83.203 (2)°
V = 1047.64 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.34 mm⁻¹
T = 300 K
0.27 × 0.15 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.94, T _max = 0.96
27365 measured reflections
6685 independent reflections
5249 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.130
S = 1.03
6685 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.47 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 datablocks I, global. DOI: 10.1107/S160053681000704X/ng2738sup1.cif

e-66-0o717-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000704X/ng2738Isup2.hkl

e-66-0o717-Isup2.hkl^{(320.6KB, 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
N1B—H1B⋯O2ⁱ	0.86	2.02	2.8547 (15)	164

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Dr Babu Varghese, Sophiticated Analytical Instrumentation Facility, Indian Institute of Technology, Chennai, for the data collection.

supplementary crystallographic information

Comment

Pyrrolo ring compounds are prevalent in a variety of biologically active compounds (Watson et al., 2001) and find utility in the treatment of diseases such as diabetes, cancer and viral infections. Since the biological activity depends on the conformation of rings that constitute a molecule, precise description, at atomic resolution, of the title compound is expected to supplement further studies on structure-activity relationships on these compounds. Also, the effect of halogen- subsitutions on the conformation of the molecule and consequently on the packing modes remains an area of immense interest in crystallography (Awwadi et al., 2006).

In the title compound (I), the 5-membered methyl substitued pyrroline ring adopts the envelope conformation with C5 deviating from the plane defined by the rest of the atoms of the ring by 0.639 (2) A° The puckering parameters (Cremer & Pople, 1975) of this ring are Q = 0.431 (2)Å and φ = 331.2 °. The piperidinone ring adopts a slightly twisted chair conformation with the N1A and C4A atoms deviating by about 0.712 (2) and -0.523 (2) A°, respectively, from the plane defined by C2A,C3,C5A and C6A with an r.m.s. deviation of 0.041 A°. The chair conformation is also evident from the corresponding puckering amplitudes [Q=0.561 (2) A°, /q = 16.0 (2)°, /f = 30.8 (6)°]. The oxindole and the dichloro substituted phenyl rings are planar.

A relatively strong intermolecular [N1B—H1B···O2(-x, -y, 1-z)] hydrogen bond relates centrrosymmetric pairs of molecules (Fig.2). These N—H···O hydrogen bonds form R⁸₂ graph set motifs (Etter et al., 1990) which are interconnected through Cl···Cl interactions [Cl1···.Cl2 (x-1, y, z) 3.478 (1) A°] leading to columns of molecules parallel to the a-axis (Fig.3). These columns resemble a 'ladder-like' arrangement of molecules much similar to the one seen in DNA, except for the twist. These columns of molecules have interactions that are van der Waals in nature.

Experimental

A mixture of 1-methyl-3-[(E)-(2,4-dichlorophenyl)methylidene] tetrahydro-4(1H)pyridinone (1 mmol), isatin (1 mmol) and sarcosine (1 mmol) were refluxed in methanol (15 ml) for 4 h. After completion of the reaction (TLC), the mixture was poured into water (30 ml) and the precipitate was filtered off and washed with water to obtain the product as white solid (0.28 g, 85%), m.p. 190–191 °C