Ethyl 1-(4-methoxy­phen­yl)-2-nitro-3-[4-oxo-3-phenyl-1-(4-methoxy­phen­yl)azetidin-2-yl]-2,3,10,10a-tetra­hydro-1H,5H-pyrrolo[1,2-b]isoquinoline-10a-carboxyl­ate

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

doi:10.1107/S1600536808010428

. 2008 Apr 23;64(Pt 5):o887–o888. doi: 10.1107/S1600536808010428

Ethyl 1-(4-methoxyphenyl)-2-nitro-3-[4-oxo-3-phenyl-1-(4-methoxyphenyl)azetidin-2-yl]-2,3,10,10a-tetrahydro-1H,5H-pyrrolo[1,2-b]isoquinoline-10a-carboxylate

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

PMCID: PMC2961124 PMID: 21202371

Abstract

In the molecule of the title compound, C₃₈H₃₇N₃O₇, the pyrrolidine ring adopts a twist conformation and the six-membered heterocyclic ring has a boat conformation. In the crystal structure, molecules are linked into a three-dimensional framework through intermolecular C—H⋯O hydrogen bonds. One ethyl group is disordered over two positions with occupancies 0.67 (2)/0.33 (2).

Related literature

For related literature, see: Allen et al. (1987 ▶); Amal Raj et al. (2003 ▶); Borthwick et al. (2003 ▶); Brakhage (1998 ▶); Cremer & Pople (1975 ▶); Fernandes et al. (2004 ▶); Kamala et al. (2008 ▶); Katritzky et al. (1996 ▶); Morin & Gorman (1982 ▶); Nardelli (1983 ▶); Sundari et al. (2006 ▶); Verkman (1990 ▶); Weissman et al. (1993 ▶); Georg & Ravikumar (1993 ▶); LaVoie et al. (1983 ▶).

Experimental

Crystal data

C₃₈H₃₇N₃O₇
M _r = 647.71
Orthorhombic,
a = 9.0149 (3) Å
b = 11.0865 (4) Å
c = 33.3731 (11) Å
V = 3335.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEX2 diffractometer
Absorption correction: multi-scan (Blessing, 1995 ▶) T _min = 0.982, T _max = 0.982
68599 measured reflections
3960 independent reflections
3318 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.107
S = 1.05
3960 reflections
453 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT (Bruker, 2004 ▶); data reduction: SAINT and XPREP Bruker, 2004 ▶); 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, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808010428/bt2696sup1.cif

e-64-0o887-sup1.cif^{(32.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010428/bt2696Isup2.hkl

e-64-0o887-Isup2.hkl^{(190.2KB, 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
C6—H6⋯O2ⁱ	0.98	2.42	3.260 (3)	143
C20—H20⋯O1ⁱⁱ	0.93	2.47	3.397 (3)	172
C29—H29⋯O3	0.93	2.59	3.442 (3)	152
C29—H29⋯N2	0.93	2.50	3.168 (3)	128
C33—H33⋯O1	0.93	2.44	3.054 (4)	123

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

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

Quinoline is a hepatocarcinogen in mice and rats, a mutagen in Salmonella typhimurium and induces unscheduled DNA synthesis in primary cultures of rat hepatocytes (LaVoie et al., 1983). Quinolinium based chloride sensitive flourescent indicators provide a new approach to study chloride transport mechanisms and regulation (Verkman, 1990). Pyrrole derivatives inhibit cytokine-dependent induction of human immunodeficiency virus (HIV) expression in chronically infected promonocytic cells (Weissman et al., 1993). Pyrroles possess anti inflammatory (Fernandes et al., 2004), anti viral (Borthwick et al., 2003), antifungal and antimicrobial activities (Amal Raj et al., 2003). β lactams are one of the best known and most extensively studied class of compounds due to their biological activity (Morin & Gorman, 1982; Georg & Ravikumar, 1993; Katritzky et al., 1996). The most commonly used β lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporin (Brakhage, 1998). Due to these importance the crystal structure determination of the title compound (I) was carried out and the results are presented here.

Fig 1 shows a plot of compound (I). Bond lengths and angles are within normal ranges (Allen et al., 1987) and comparable with those of reported structures (Kamala et al., 2008; Sundari et al., 2006).

In the molecule the pyrrolidine ring exhibits a twist conformation with asymetry parameters (Nardelli,1983)ΔC_s(C5) = 5.2 (2), ΔC₂(C6) = 39.6 (2) and with the puckering parameters (Cremer and Pople, 1975) q2 = 0.274 (3)Å and φ2 =267.5 (5)°. The six membered ring C7/C8/C9/C14/C15/N2 exhibits a boat conformation with the puckering parameters Q=0.699 (3) Å, Θ = 88.8 (2)° and φ = 120.1 (2)°. The sum of bond angles around N1 [353.59°], and around N3 [359.94°] indicate sp², those around atom N2 [338.58°] indicate sp³ hybridization. The pyrrolidine ring and the phenyl ring C9—C14 are nearly planar with each other with a dihedral angle of 9.49 (7)° while the phenyl rings are oriented at right angles to each other making an angle of 87.48 (7)°.

In the crystal packing, C—H···O interactions stabilize crystal structure.

Experimental

To a stirring solution of 1 mmol of 5-[1'-N-(p-methoxy)-phenyl)-3'-phenyl- azetidine-2'-one]-4-nitro-3-(p-methoxy)-phenyl-2-ethoxy carbonyl-2-benzyl -pyrrolidine in 20 ml of dry chloroform was added 1 mmol of paraformaldehyde followed by 0.1 mmol of trifluroacetic acid at room temperature. After completion of the reaction the mixture was washed with water and dried over Na₂SO₄. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography with hexane ethylacetate (9:1) to obtain pure cyclized product. The compound was recrystallized from ethylacetae.