Ethyl (E)-3-[1′-ethyl-2-oxo-4′-(phenyl­sulfon­yl)-2H-spiro­[acenaphthyl­ene-1,2′-pyrrolidine]-3′-yl]acrylate

Ulaganathan Sankar; R Uma; S Sundaramoorthy; D Velmurugan

doi:10.1107/S1600536812016042

. 2012 Apr 18;68(Pt 5):o1401. doi: 10.1107/S1600536812016042

Ethyl (E)-3-[1′-ethyl-2-oxo-4′-(phenylsulfonyl)-2H-spiro[acenaphthylene-1,2′-pyrrolidine]-3′-yl]acrylate

Ulaganathan Sankar ^a, R Uma ^a, S Sundaramoorthy ^b, D Velmurugan ^b,^*

PMCID: PMC3344527 PMID: 22590289

Abstract

In the title compound, C₂₈H₂₇NO₅S, the five-membered pyrrolidine ring, which exhibits an envelope conformation (the C atom at the spiral junction being the flap atom), makes dihedral angles of 57.37 (10) and 86.84 (8)°, respectively, with the phenyl ring and the acenaphthylene ring system. In the crystal, molecules associate via two C—H⋯O hydrogen bonds, forming R ₂ ²(20) and R ₂ ²(10) graph-set motifs.

Related literature

For the biological activity of spiro compounds, see: Kobayashi et al. (1991 ▶); James et al. (1991 ▶); Obniska et al. (2003 ▶); Peddi et al. (2004 ▶). For ring conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₂₈H₂₇NO₅S
M _r = 489.58
Triclinic,
a = 11.1917 (8) Å
b = 11.7778 (9) Å
c = 12.1511 (9) Å
α = 93.572 (3)°
β = 115.911 (3)°
γ = 114.134 (3)°
V = 1256.82 (17) Å³
Z = 2
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 295 K
0.26 × 0.23 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.957, T _max = 0.967
19294 measured reflections
6053 independent reflections
4834 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.127
S = 1.04
6053 reflections
318 parameters
H-atom parameters constrained
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.30 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/S1600536812016042/rk2349sup1.cif

e-68-o1401-sup1.cif^{(25.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016042/rk2349Isup2.hkl

e-68-o1401-Isup2.hkl^{(290.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016042/rk2349Isup3.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
C21—H21A⋯O1ⁱ	0.97	2.53	3.452 (3)	160
C28—H28⋯O5ⁱⁱ	0.93	2.55	3.336 (3)	142

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

Acknowledgments

The authors thank the TBI X-ray Facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. SS and DV thank the University Grants Commission (UGC & SAP) for financial 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). Spiro-pyrrolidine derivatives are unique tetracyclic 5-HT(2 A) receptor antagonist (Obniska et al., 2003; Peddi et al., 2004). In view of this importance, the crystal structure of the title compound, has been determined and the results are presented here.

The pyrrolidine ring makes dihedral angles of 57.37 (10)° and 86.84 (8)° with the phenyl ring and the acenaphthylene ring system, respectively. The sum of the angles at N1 of the pyrrolidine ring - 335.5 (3)°) is in accordance with sp³ hybridization. The pyrrolidine ring adopts an envelope conformation with C8 deviating from the plane defined by the rest of the atoms of the ring by -0.2603 (2)Å. The puckering parameters (Cremer & Pople, 1975) of this ring are Q_T= 0.4137 (2)Å and φ₂ = 30.3 (3)°.

The crystal packing is stabilized by C—H···O intermolecular interactions. Atom C21 acts as a donor to O1ⁱ and atom C28 acts as a donor to O5ⁱⁱ, generating R₂²(20) and R₂²(10) graph set motifs, respectively. Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) -x+2, -y, -z+1.

Experimental

The mixture of (2E,4E)–ethyl–5–(phenyl–sulfonyl)penta–2,4–dienoate (1 g, 3.8 mmol), N–ethyl glycine (0.43 g 4.1 mmol) and acenapthoquinone (0.75 g 4.1 mmol) in dry 1,4–dioxane (20 ml) was refluxed for 5 hr under N2 atm. The reaction mixture was concentreated to remove the solvent and then purified by column chromatography to yield the required title compound as a coloureless solid. The solvent accessible void 47Å³ is found in crystal.