3-(4-Chloro­phen­oxy)-1-(4-meth­oxy­phen­yl)-4-(4-nitro­phen­yl)azetidin-2-one

Ray J Butcher; Mehmet Akkurt; Aliasghar Jarrahpour; Seid Ali Torabi Badrabady

doi:10.1107/S1600536811013018

. 2011 Apr 13;67(Pt 5):o1101–o1102. doi: 10.1107/S1600536811013018

3-(4-Chlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitrophenyl)azetidin-2-one

Ray J Butcher ^a, Mehmet Akkurt ^b,^*, Aliasghar Jarrahpour ^c, Seid Ali Torabi Badrabady ^c

PMCID: PMC3089293 PMID: 21754420

Abstract

In the title compound, C₂₂H₁₇ClN₂O₅, the nearly planar four-membered β-lactam ring [maximum deviation of 0.016 (1) for the N atom] makes dihedral angles of 53.07 (9), 73.19 (9) and 6.61 (9)° with the chloro-, nitro- and methoxybenzene rings, respectively. The crystal structure is stabilized by C—H⋯O hydrogen bonds, a weak C—H⋯π interaction and a π–π stacking interaction [centroid–centroid distance = 3.6513 (8) Å] between the methoxybenzene rings of inversion-related molecules.

Related literature

For general background to β-lactams, see: Banik et al. (2004 ▶); Garud et al. (2009 ▶); Jarrahpor & Khalili (2007 ▶); Jarrahpour & Zarei (2006 ▶, 2010 ▶). For some of our previous reports of the structures of β-lactams, see: Akkurt et al. (2008a ▶,b ▶, 2011a ▶,b ▶); Baktır et al. (2009 ▶); Yalçın et al. (2009 ▶); Çelik et al. (2009 ▶).

Experimental

Crystal data

C₂₂H₁₇ClN₂O₅
M _r = 424.83
Monoclinic,
a = 6.0863 (2) Å
b = 20.0855 (7) Å
c = 17.3819 (7) Å
β = 97.419 (4)°
V = 2107.09 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 123 K
0.49 × 0.17 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T _min = 0.901, T _max = 0.970
20727 measured reflections
10522 independent reflections
7301 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.074
wR(F ²) = 0.190
S = 1.08
10522 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); 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 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013018/su2266sup1.cif

e-67-o1101-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811013018/su2266Isup2.hkl

e-67-o1101-Isup2.hkl^{(514.5KB, hkl)}

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

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

Cg4 is the centroid of the C16–C21 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4ⁱ	1.00	2.45	3.287 (2)	141
C3—H3A⋯O1ⁱⁱ	1.00	2.29	3.2439 (17)	159
C20—H20A⋯O1ⁱⁱⁱ	0.95	2.50	3.3086 (18)	144
C21—H21A⋯O1	0.95	2.52	3.1397 (18)	123
C6—H6A⋯Cg4^iv	0.95	2.71	3.4145 (17)	131

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

Table 2. The dihedral angles between the mean planes of the rings in the title molecule (°).

	Ring 2	Ring 3	Ring 4
Ring 1	53.07 (9)	73.19 (9)	6.61 (9)
Ring 2		64.42 (7)	46.85 (7)
Ring 3			79.45 (7)

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Ring 1 is the N1/C1–C3 β-lactam ring, ring 2 is the C4–C9 benzene ring, ring 3 is the C10–C15 benzene ring and ring 4 is C16–C21 benzene ring.

Acknowledgments

AJ and SATB thank the Shiraz University Research Council for financial support (grant No. 89-GR–SC-23).

supplementary crystallographic information

Comment

The β-lactam antibiotics consists of a strained, four-membered, heterocyclic ring, known as the β-lactam ring (Garud et al., 2009). The most literal definition of a β-lactam antibiotics are the monocyclic β-lactams that do not contain another ring fused to the β-lactam one (Jarrahpour & Zarei, 2006). The discovery of the monocyclic β-lactams suggesting that the biological activity of β-lactams was strictly correlated to the presence of a suitably functionalized β-lactam ring (Jarrahpour & Zarei, 2010; Banik et al., 2004). The β-lactam ring systems show many interesting biological properties, such as cholesterol absorption inhibitors, human cytomegalovirus (HCMV) protease inhibitors, thrombin inhibitors, antihyperglycemic, anti-tumour, anti-HIV, human leukocyte elastase (HLE), potential antimalarials, anti-influenza virus, and serine-dependent enzyme inhibitors (Jarrahpor & Khalili, 2007).

As an extension of our work (Baktır et al., 2009; Çelik et al., 2009; Yalçın et al., 2009; Akkurt et al., 2008a,b; Akkurt et al., 2011a,b) on structural characterization of the β-lactam compounds, we herein report on the X-ray crystal structure of the title compound.

In the title molecule, Fig. 1, the β-lactam ring (N1/C1–C3) is nearly planar, with maximum deviations of -0.016 (1) for N1 and 0.015 (1) Å for C1. The C1—N1—C16—C17, N1–C3—C10—C11, O1—C1—C2—O2, C3—C2—O2—C4 and C2—O2—C4—C5 torsion angles are -172.79 (14), -159.77 (12), -60.7 (2), 92.79 (14) and -168.40 (12) °, respectively. The dihedral angles between the ring planes are listed in Table 2.

In the crystal molecules are linked by intermolecular C—H···O hydrogen-bond interactions and a weak C—H···π interaction (Table 1 and Fig. 2). Furthermore, there is a π-π stacking interaction [Cg4···Cg4ⁱ = 3.6513 (8) Å, where Cg4 is a centroid of the C16–C21 benzene ring; symmetry code: (i) = 1 - x, 1 - y, 1 - z] between the benzene rings attached to the methoxy group of molecules related by an inversion center.

Experimental

A solution of N-(4-nitrobenzylidene)-4-methoxybenzenamine (1.00 mmol) was stirred with 4-chlorophenoxy acetic acid (1.50 mmol), p-toluenesulfonyl chloride (1.50 mmol) and triethylamine (2.5 mmol) in dry CH₂Cl₂ at room temperature over night. Then it was washed with HCl 1 N (20 ml), saturated NaHCO₃ (20 ml), brine (20 ml), dried over Na₂SO₄ and the solvent was evaporated under reduced pressure to give the crude product which was then purified by column chromatography over silica gel (7:3 hexane-EtOAc). (Yield 78%; mp: 415–417 K). Elemental analysis: Calc. for C₂₂H₁₇ClN₂O₅: C, 62.20; H, 4.03; N, 6.59%; Found: C, 62.15; H, 4.07; N, 6.65%.