Methyl 2-benzyl-5-[1-(4-methoxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-4-nitro-3-phenyl­pyrrolidine-2-carboxyl­ate

S Sundaresan; P Ramesh; N Arumugam; R Raghunathan; M N Ponnuswamy

doi:10.1107/S1600536808029875

. 2008 Sep 24;64(Pt 10):o1993. doi: 10.1107/S1600536808029875

Methyl 2-benzyl-5-[1-(4-methoxyphenyl)-4-oxo-3-phenylazetidin-2-yl]-4-nitro-3-phenylpyrrolidine-2-carboxylate

S Sundaresan ^a, P Ramesh ^b, N Arumugam ^c, R Raghunathan ^c, M N Ponnuswamy ^a,^*

PMCID: PMC2959360 PMID: 21201192

Abstract

In the title molecule, C₃₅H₃₃N₃O₆, the pyrrolidine ring adopts a twist conformation. The molecules are paired into centrosymmetric dimers by weak intermolecular C—H⋯O hydrogen bonds. The dimers interact further again via C—H⋯O hydrogen bonds and N—H⋯O intramolecular interaction also stabilize the crystal packing.

Related literature

For the pharmacological properties of β-lactam derivatives, see: Alcaide et al. (2000 ▶). For general background, see: Cremer & Pople (1975 ▶); Nardelli (1983 ▶); Beddoes et al. (1986 ▶).

Experimental

Crystal data

C₃₅H₃₃N₃O₆
M _r = 591.64
Triclinic,
a = 10.1727 (2) Å
b = 10.4210 (2) Å
c = 15.1680 (3) Å
α = 91.833 (1)°
β = 106.154 (1)°
γ = 102.536 (1)°
V = 1500.31 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 (2) K
0.23 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T _min = 0.978, T _max = 0.987
29479 measured reflections
5290 independent reflections
4498 reflections with I > 2σ(I)
R _int = 0.022

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.112
S = 1.02
5290 reflections
400 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2; data reduction: SAINT (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: SHELXL97 and PLATON (Spek, 2003 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808029875/cv2439sup1.cif

e-64-o1993-sup1.cif^{(28.7KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808029875/cv2439Isup2.hkl

e-64-o1993-Isup2.hkl^{(253.8KB, 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
N1—H1⋯O1	0.898 (19)	2.314 (18)	2.7378 (18)	108.7 (14)
C7—H7B⋯O3ⁱ	0.96	2.48	3.145 (2)	126
C14—H14⋯O5ⁱⁱ	0.93	2.60	3.359 (2)	139
C30—H30⋯O1ⁱⁱⁱ	0.93	2.57	3.240 (2)	129

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

Acknowledgments

SS thanks Dr Babu Varghese, SAIF, IIT Madras, Chennai, India, for his kind help in data collection.

supplementary crystallographic information

Comment

An extensive use of common β-lactam antibiotics, such as penicillin and cephalosporins, in medicine has resulted in an increasing number of resistant bacteria through mutation and β-lactamase gene transfer. The importance and structural diversity of biologically active β-lactam antibiotics, the most widely employed family of antimicrobial agents led to the development of efficient approaches for the construction of appropriately substituted 2-azetidinones (Alcaide et al., 2000). As a contribution to this field, we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the pyrrolidine ring adopts a twist conformation. The puckering parameters (Cremer & Pople, 1975) and the asymmetry parameter (Nardelli, 1983) for this ring are q₂ = 0.382 (2) Å, π = 340.9 (2)° and Δ2(C3) = 0.48 (14)°, respectively. The sum of angles at N1 of the pyrrolidine ring system [327.14 (12)°] is in accordance with sp³ hybridization (Beddoes et al., 1986). The β-lactam ring is planar and the keto atom O5 deviates from this plane at 0.049 (1) Å.

The weak intermolecular C—H···O hydrogen bonds (Table 1) contribute to the crystal packing stability.

Experimental

β-Lactam aldehyde (1.0 mol) was treated with phenyl alanine methyl ester hydrochloride in the presence of Et₃N (2.5 mol) and anhydrous MgSO₄ (2.0 g) in dry chloromethane (10 ml) at room temperature for 12 h to give the imine. The imine was washed with water and dried over Na₂SO₄. The solvent was evaporated under vacuum. The imine was then stirred with silver (I) acetate and nitrostyene (1.0 mol) in the presence of Et₃N (1.2 mol) and molecular sieves in dry toluene (30 ml) again at room temperature for 12 h. The reaction mixture was filtered through a plug celite. The solvent was evaporated under reduced pressure and the residue was subjected to column chromatogaraphy on silicagel (100–200 mesh), with hexane and ethyl acetate (7:3) as eluent to give the product. The compound was recrystallized from ethyl acetate.