1-(4-Meth­oxy­phen­yl)-4-(3-nitro­phen­yl)-3-phen­oxy­azetidin-2-one

Zeliha Baktır; Mehmet Akkurt; Aliasghar Jarrahpour; Roghaye Heiran

doi:10.1107/S1600536811003382

. 2011 Jan 29;67(Pt 2):o537–o538. doi: 10.1107/S1600536811003382

1-(4-Methoxyphenyl)-4-(3-nitrophenyl)-3-phenoxyazetidin-2-one

Zeliha Baktır ^a, Mehmet Akkurt ^a,^*, Aliasghar Jarrahpour ^b, Roghaye Heiran ^b

PMCID: PMC3051763 PMID: 21523185

Abstract

In the title compound, C₂₂H₁₈N₂O₅, the four-membered β-lactam ring is nearly planar, with a maximum deviation of 0.023 (2) Å for the N atom, and has long C—C distances of 1.525 (5) and 1.571 (5) Å. The mean plane of this group makes dihedral angles of 11.61 (19), 74.5 (2) and 72.3 (2)° with three aromatic rings. An intramolecular C—H⋯O hydrogen bond occurs. The packing of the molecules in the crystal structure is governed mainly by intermolecular C—H⋯O hydrogen-bonding and C—H⋯π stacking interactions. Furthermore, a π–π interaction [centroid–centroid distance = 3.6129 (19) Å] helps to stabilize the crystal structure.

Related literature

For general background to β-lactams, see: Jubie et al. (2009 ▶); Mehta et al. (2010 ▶); Vatmurge et al. (2008 ▶); Von Nussbaum et al. (2006 ▶). For related structures, see: Akkurt et al. (2006 ▶); Ercan et al. (1996a ▶,b ▶); Kabak et al. (1999 ▶).

Experimental

Crystal data

C₂₂H₁₈N₂O₅
M _r = 390.38
Triclinic,
a = 7.7934 (4) Å
b = 11.2813 (3) Å
c = 11.8818 (2) Å
α = 77.771 (4)°
β = 80.948 (5)°
γ = 71.052 (4)°
V = 961.18 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ▶) T _min = 0.981, T _max = 0.981
3928 measured reflections
3928 independent reflections
1872 reflections with I > 2σ(I)
R _int = 0.104

Refinement

R[F ² > 2σ(F ²)] = 0.059
wR(F ²) = 0.155
S = 1.01
3927 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811003382/bv2175sup1.cif

e-67-0o537-sup1.cif^{(25.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003382/bv2175Isup2.hkl

e-67-0o537-Isup2.hkl^{(192.5KB, hkl)}

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg2 and Cg4 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2	0.93	2.53	3.125 (4)	122
C2—H2⋯O2ⁱ	0.93	2.59	3.464 (4)	156
C16—H16⋯O4ⁱⁱ	0.93	2.52	3.164 (5)	126
C4—H4⋯Cg4ⁱⁱⁱ	0.93	2.89	3.716 (4)	149
C9—H9⋯Cg2^iv	0.98	2.55	3.463 (4)	154

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

Acknowledgments

ZB and MA thank the Unit of the Scientific Research Projects of Erciyes University, Turkey for the research grant FBD-10–2949 and for support of the data collection at Atatürk University, Turkey. AJ and RH also thank the Shiraz University Research Council for financial support (grant No. 89-GR—SC-23).

supplementary crystallographic information

Comment

Azetidine-2-ones (β-lactams) were the first group of antibacterial natural products introduced as a therapeutic treatment of bacterial infections (Von Nussbaum et al.. 2006). The biological activity of β-lactams is mostly believed to be associated with the chemical reactivity of their β-lactam ring and on its substituents, especially at the nitrogen of the 2-azetidinone ring (Mehta et al. 2010). p-Anisidine derivatives have been found to be biologically interesting for many years (Jubie et al. 2009). Continuous change in the structures of known active compounds and the preparation of new types (Vatmurge et al. 2008) has been forced by the development of bacterial resistance to known compounds (Vatmurge et al. 2008).

In the title compound (I), (Fig. 1), the β-lactam ring (N1/C8–C10) is nearly planar, with a maximum deviation of 0.023 (2)Å for N1. The bond lengths in the β-lactam ring are comparable with those found in previous similar studies (Akkurt et al. 2006; Ercan et al., 1996a,b; Kabak et al., 1999).

Its mean plane makes dihedral angles of 11.61 (19), 74.5 (2) and 72.3 (2)°, respectively, with three aromatic rings (C1–C6), (C11–C16) and (C17–C22). The details of the dihedral angles between the planes of the rings are given in Table 2.

A weak intramolecular C—H···O hydrogen bond contributes to the stability of the molecular configuration (Table 1). The crystal structure is stabilized by intermolecular C—H···O hydrogen-bonding (Table 1, Fig. 2) and C—H···π stacking interactions (Table 1). Furthermore, a π-π interaction [Cg1···Cg3(x, y, z) = 3.6129 (19) Å, Cg1 and Cg3 are the centroids of the N1/C8–C10 β-lactam ring and the C11–CC16 benzene rings, respectively] helps to stabilize the crystal structure.

Experimental

A mixture of N-(3-nitrobenzylidene)-4-methoxybenzeneamine (1.28 g, 5.00 mmol) and triethylamine (2.53 g, 25.00 mmol), phenoxyacetic acid (1.14 g, 7.50 mmol) and tosyl chloride (1.43 g, 7.50 mmol) in CH₂Cl₂ (30 ml) was stirred at room temperature overnight. Then it was washed with HCl 1 N, saturated sodium bicarbonate solution and brine, dried with Na₂SO₄ and the solvent was evaporated to give the crude product as a white crystal which was then purified by recrystallization from ethyl acetate (Yield 47%). [mp: 415° K]. IR (KBr, cm^-1): 1739.7 (CO β-lactam). ¹H NMR (250 MHz, CDCl₃) δ 3.75 (Me, s, 3H), 5.48 (H-8, d, 1H, J = 4.75), 5.63 (H-9, d, 1H, J = 4.75), 6.75–8.23 (ArH, m, 13H); ¹³C NMR (62.9 MHz, CDCl₃) δ 55.46 (Me), 61.02 (C-8), 81.01 (C-9), 114.62–156.83 (aromatic carbons), 161.86 (CO β-lactam); GC—MS m/z =390 [M+].