3-(2,4-Di­chloro­phen­oxy)-1-(4-meth­oxy­benz­yl)-4-(4-nitro­phen­yl)azetidin-2-one

Zeliha Atioğlu; Mehmet Akkurt; Aliasghar Jarrahpour; Roghayeh Heiran; Namık Özdemir

doi:10.1107/S1600536814015013

. 2014 Jul 2;70(Pt 8):o835–o836. doi: 10.1107/S1600536814015013

3-(2,4-Dichlorophenoxy)-1-(4-methoxybenzyl)-4-(4-nitrophenyl)azetidin-2-one

Zeliha Atioğlu ^a, Mehmet Akkurt ^b,^*, Aliasghar Jarrahpour ^c, Roghayeh Heiran ^c, Namık Özdemir ^d

PMCID: PMC4158542 PMID: 25249889

Abstract

The β-lactam ring of the title compound, C₂₃H₁₈Cl₂N₂O₅, is nearly planar [maximum deviation = 0.019 (2) Å for the N atom] and its mean plane makes dihedral angles of 56.86 (15), 68.83 (15) and 83.75 (15)° with the dichloro-, nitro- and methoxy-substituted benzene rings, respectively. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with R ₂ ²(10) loops. The dimers are linked by further C—H⋯O hydrogen bonds, forming sheets lying parallel to (001). The molecular packing is further stabilized by C—H⋯π interactions.

Keywords: crystal structure

Related literature

For general background to β-lactams, see: Schunk & Enders (2000 ▶); France et al. (2004 ▶); Pitts & Lectka (2014 ▶); Arya et al. (2014 ▶); Banik et al. (2003 ▶); Delpiccolo et al. (2003 ▶); Hodous & Fu (2002 ▶). For the crystal structures of some β-lactams, see: Akkurt et al. (2011 ▶); Butcher et al. (2011 ▶).

Experimental

Crystal data

C₂₃H₁₈Cl₂N₂O₅
M _r = 473.29
Monoclinic,
a = 5.0716 (5) Å
b = 20.9390 (12) Å
c = 20.1516 (18) Å
β = 96.457 (7)°
V = 2126.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.59 × 0.28 × 0.06 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.901, T _max = 0.972
15060 measured reflections
4179 independent reflections
2123 reflections with I > 2σ(I)
R _int = 0.062

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.061
S = 0.85
4179 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814015013/su2747sup1.cif

e-70-0o835-sup1.cif^{(30.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814015013/su2747Isup2.hkl

e-70-0o835-Isup2.hkl^{(229.3KB, hkl)}

Click here for additional data file.^{(7.9KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814015013/su2747Isup3.cml

CCDC reference: 1010327

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

Cg is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.98	2.58	3.417 (3)	143
C6—H6⋯O5ⁱⁱ	0.93	2.57	3.328 (3)	139
C12—H12⋯O3ⁱⁱⁱ	0.93	2.57	3.495 (4)	176
C16—H16A⋯Cg ^iv	0.97	2.70	3.649 (3)	166

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

Acknowledgments

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund). AJ and RH thank the Shiraz University Research Council for financial support.

supplementary crystallographic information

S1. Comment

The β-lactam (2-azetidinone) ring is the most well known heterocycle to have been studied during the last century (Pitts & Lectka, 2014; France et al., 2004; Arya et al., 2014). The β-lactam framework is the structural element of a large class of broad-spectrum antibiotics such as penicillins, cephalosporins and monobactams (Delpiccolo et al., 2003; Schunk & Enders, 2000; Banik et al., 2003), that effectively combat bacterial infections (Schunk & Enders, 2000). However, the need for new antibiotics has been growing, as a result of the rapid emergence of bacterial strains' resistance to traditional drugs (Hodous & Fu, 2002; Delpiccolo et al., 2003). Therefore, in continuation of our research on the synthesis of β-lactams, we describe herein the synthesis and crystal structure of the title compound.

In the title molecule, Fig. 1, the β-lactam ring (N1/C1–C3) is nearly planar with a maximum deviation of -0.016 (1) Å for atom N1. The mean plane of this four-membered β-lactam ring is twisted from the planes of the dichloro-, nitro- and methoxy substituted benzene rings, making the dihedral angles of 56.86 (15), 68.83 (15) and 83.75 (15)°, respectively. The bond lengths and bond angles are within normal values and are comparable with those reported for similar compounds (Akkurt et al., 2011; Butcher et al., 2011).

In the crystal, molecules are linked by a pair of C—H···O hydrogen bonds forming inversion dimers with R²₂(10) loops (Table 1 and Fig. 2). The dimers are linked by further C-H···O hydrogen bonds forming sheets lying parallel to (001). The molecular packing is further stabilized by C—H···π interactions (Table 1).

S2. Experimental

A mixture of N-(4-nitrobenzylidene) (4-methoxyphenyl) methanamine (0.27 g, 1.00 mmol), 2,4-dichlorophenoxyacetic acid (0.34 g, 1.50 mmol), tosyl chloride (0.28 g, 1.50 mmol) and triethylamine (0.25 g, 2.50 mmol) in dry CH₂Cl₂ was stirred at room temperature overnight. After completion of the reaction, monitored by TLC, the mixture was washed with HCl (1 N), saturated sodium bicarbonate solution, brine, dried over anhydrous Na₂SO₄ and the solvent was then evaporated under vacuum to afford the crude product. This was purified by recrystallization from EtOAc giving pale yellow prismatic crystals on slow evaporation of the solvent (yield 72%). M.p. 397 - 399 K. Spectroscopic data for the title compound are given in the archived CIF.