3-(4-Chloro­phen­yl)-4-(4-methoxyphen­yl)-6-(phenyl­selenylmeth­yl)-2,3,3a,3b,4,5,5a,6,1′′,2′′,3′′,4′′-do­deca­hydro­azeto[2′,3′:3,4]pyrrolo[1,2-b]isoxazole-2-spiro-2′′-naphthalene-5,1′′-dione

E Theboral Sugi Kamala; S Nirmala; L Sudha; N Arumugam; R Raghunathan

doi:10.1107/S1600536808006570

. 2008 Mar 14;64(Pt 4):o716–o717. doi: 10.1107/S1600536808006570

3-(4-Chlorophenyl)-4-(4-methoxyphenyl)-6-(phenylselenylmethyl)-2,3,3a,3b,4,5,5a,6,1′′,2′′,3′′,4′′-dodecahydroazeto[2′,3′:3,4]pyrrolo[1,2-b]isoxazole-2-spiro-2′′-naphthalene-5,1′′-dione

E Theboral Sugi Kamala ^a, S Nirmala ^a, L Sudha ^b,^*, N Arumugam ^c, R Raghunathan ^c

PMCID: PMC2960925 PMID: 21202107

Abstract

In the title compound, C₃₆H₃₁ClN₂O₄Se, the four-membered β-lactam ring is fused to a pyrrolidine ring. The central five-membered ring of the fused tricyclic system exhibits an envelope conformation with the N atom as the flap, while the other five-membered ring exhibits a twist conformation. The chlorophenyl ring is almost perpendicular to the pyrrolidine ring, making a dihedral angle of 73.45 (1)°. The crystal structure is stabilized by weak intermolecular C—H⋯O interactions and the packing is further enhanced by C—H ⋯N interactions and π–π interactions between benzene rings of tetralone groups in molecules related by an inversion center, with a centroid–centroid separation of 3.8923 (2) Å.

Related literature

For related literature, see: Allen et al. (1987 ▶); Amal Raj et al. (2003 ▶); Brakhage (1998 ▶); Cremer & Pople (1975 ▶); Kilonda et al. (1995 ▶); Nardelli (1983 ▶).

Experimental

Crystal data

C₃₆H₃₁ClN₂O₄Se
M _r = 670.04
Monoclinic,
a = 14.4697 (3) Å
b = 10.9493 (3) Å
c = 19.3011 (4) Å
β = 94.661 (1)°
V = 3047.82 (12) Å³
Z = 4
Mo Kα radiation
μ = 1.36 mm⁻¹
T = 293 (2) K
0.30 × 0.30 × 0.24 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.671, T _max = 0.720
37171 measured reflections
8699 independent reflections
5453 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.176
S = 1.02
8699 reflections
398 parameters
H-atom parameters constrained
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.86 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808006570/bh2162sup1.cif

e-64-0o716-sup1.cif^{(28.3KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808006570/bh2162Isup2.hkl

e-64-0o716-Isup2.hkl^{(417KB, 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
C4—H4⋯O4ⁱ	0.98	2.57	3.305 (3)	132
C23—H23⋯O2	0.98	2.32	2.803 (3)	109
C23—H23⋯N1	0.98	2.54	2.918 (3)	103

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Symmetry code: (i) Inline graphic .

Acknowledgments

ETSK thanks Professor M. N. Ponnuswamy and Professor D. Velmurugan, Department of Crystallography and Biophysics, University of Madras, India, for their guidance and valuable suggestions. ETSK also thanks SRM Management for their support.

supplementary crystallographic information

Comment

Pyrrolidines and pyrroles are common structural motifs in drugs and drug candidates owing to their ability to act as selective glycosidase inhibitors, which are used in the treatment of diabetes, cancer, malaria and viral infections, including AIDS (Kilonda et al., 1995). These derivatives also possess antimicrobial and antifungal activity (Amal Raj et al., 2003). The discovery of β-lactam is very significant in the history of therapeutic medicine as an antibiotic in the form of penicillin and cephalosporin for infectious diseases (Brakhage, 1998). Due to their importance, the crystal structure determination of the title compound, (I), was carried out and the results are presented here.

Figure 1 shows the ORTEP-3 (Farrugia, 1997) plot of compound (I). Bond lengths and angles are comparable with other reported values (Allen et al., 1987).

In the molecule the five membered ring N2/C3/C2/C5/C4 exhibits envelope conformation with envelope on N2 and with an asymmetry parameter (Nardelli, 1983) Δ_s(N2) = 0.0067 (1) and with the puckering parameters (Cremer & Pople, 1975) q2 = 0.3669 (3) Å and φ2 = 70.58 (4)°. Another five membered ring C4/C23/C13/O1/N2 exhibits twist conformation with asymmetry parameters Δ_s(C4) = 0.0297 (13), Δ₂(O1) = 0.0414 (9) and with the puckering parameters q2 = 0.3452 (2) Å and φ2 = -173.27 (4)°.

The sum of bond angles around atom N1, 359.8°, and around atom N2, 324.57°, indicate sp² and sp³ hybridizations, respectively. The chlorobenzene ring is almost perpendicular to the pyrrolidine ring, making a dihedral angle of 73.45 (1)°. The anisole ring makes a dihedral angle of 14.85 (1)° with the central β-lactam ring, while angle between anisole and tetrahydronapthanone is 66.38 (1)°.

In the crystal packing, atoms O2 and O4 are involved in intermolecular and intramolecular C—H···O interactions, along with C—H···N interactions. Weak intermolecular π···π interactions occur within the benzene ring C15···C20 (1 - x, -y, 1 - z), with a centroid-to-centroid separation of 3.8923 (2) Å.

Experimental

To a solution of the bicyclic nitrone (1 mmol) in dry acetonitrile (20 ml) was added 4-chlorobenzilidene tetralone (1 mmol) under N₂ atmosphere. The mixture was refluxed for 4 h. After completion of the reaction, the solvent was distilled off under reduced pressure. The crude product was purified by column chromatography (hexane:ethyl acetate, 8:2) to give pure β-lactam (I) in good yield. The product was recrystallized from dry benzene by slow evaporation.