1-[3-(Morpholin-4-yl)prop­yl]-3-[(naph­tha­len-2-yl)oxy]-4-(3-nitro­phen­yl)azeti­din-2-one

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

doi:10.1107/S1600536814014949

. 2014 Jul 2;70(Pt 8):o833–o834. doi: 10.1107/S1600536814014949

1-[3-(Morpholin-4-yl)propyl]-3-[(naphthalen-2-yl)oxy]-4-(3-nitrophenyl)azetidin-2-one

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

PMCID: PMC4158481 PMID: 25249888

Abstract

In the title compound, C₂₆H₂₇N₃O₅, the β-lactam (azetidin-2-one) ring is nearly planar [maximum deviation = 0.011 (3) Å]. The mean plane formed by the four C atoms of the morpholine ring, which adopts a chair conformation, the benzene ring and the naphthalene ring system form dihedral angles of 72.85 (17), 87.46 (15) and 65.96 (11)°, respectively, with the β-lactam ring. In the crystal, molecules are linked via C—H⋯O hydrogen bonds, forming inversion dimers with R ₂ ²(8).

Keywords: crystal structure

Related literature

For general background to β-lactams, see: Mehta et al. (2010 ▶); Arumugam et al. (2011 ▶); Myangar & Raval (2012 ▶); Singh & Sudheesh (2014 ▶); Abdellaoui & Xu (2014 ▶); Cheng & Cheng (2007 ▶); Xiang (2013 ▶). For ring-puckering parameters, see: Cremer & Pople (1975 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₆H₂₇N₃O₅
M _r = 461.51
Triclinic,
a = 9.7068 (8) Å
b = 10.3836 (9) Å
c = 14.2041 (11) Å
α = 73.739 (6)°
β = 75.922 (6)°
γ = 63.107 (6)°
V = 1214.33 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.51 × 0.39 × 0.25 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.967, T _max = 0.985
10059 measured reflections
4486 independent reflections
2123 reflections with I > 2σ(I)
R _int = 0.088

Refinement

R[F ² > 2σ(F ²)] = 0.066
wR(F ²) = 0.176
S = 0.95
4486 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.17 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/S1600536814014949/hg5396sup1.cif

e-70-0o833-sup1.cif^{(32.5KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814014949/hg5396Isup2.hkl

e-70-0o833-Isup2.hkl^{(246KB, hkl)}

Click here for additional data file.^{(9.1KB, cml)}

Supporting information file. DOI: 10.1107/S1600536814014949/hg5396Isup3.cml

CCDC reference: 1010107

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

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O1ⁱ	0.98	2.46	3.229 (4)	135

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Symmetry code: (i) Inline graphic .

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).

supplementary crystallographic information

S1. Comment

The β-lactam ring is part of the core structure of most widely used antibiotics such as penicillins, cephalosporins, carbapenems, nocardicins and monobactam. Almost all of these antibiotics work by inhibiting bacterial cell wall biosynthesis (Mehta et al., 2010; Arumugam et al., 2011; Xiang, 2013; Myangar & Raval, 2012; Singh & Sudheesh, 2014). Functionalized β-lactams have attracted continued interests not only for their diverse and antibiotic activity, but also for their utility as versatile synthetic intermediates in organic synthesis as well as many other interesting biological properties (Cheng & Cheng, 2007; Abdellaoui & Xu, 2014). Therefore, there has been renewed interest in the synthesis of such interesting β-lactam based heterocycles with potential applications.

In the title compound (I, Fig. 1), the β-lactam ring (N1/C1–C3) is nearly planar, with the maximum deviations of -0.011 (2) Å for N1 and 0.011 (3) Å for C1 from the mean plane. The β-lactam ring makes dihedral angles of 72.85 (17), 87.46 (15) and 65.96 (11)°, respectively, with the least-squares plane formed by the four C atoms of the morpholine ring (N3/O5/C23–C26), the benzene ring (C14–C19), and the naphthalene ring system (C4–C13).

The morpholine ring adopts a chair conformation with puckering parameters: Q_T = 0.552 (4) Å, θ = 176.9 (4)° and φ = 44 (11)° (Cremer & Pople, 1975).

In the crystal structure, molecules are linked by pairs of weak C—H···O hydrogen bonds, forming inversion dimers, forming R₂²(8) motifs (Bernstein et al., 1995) along the [001] direction (Table 1, Fig. 2).

S2. Experimental

A mixture of N-(3-nitrobenzylidene)-3-morpholinopropan-1-amine (1.38 g, 5.00 mmol) and triethylamine (2.53 g, 25.00 mmol), 2-naphthoxyacetic acid (1.54 g, 7.50 mmol) and tosyl chloride (1.43 g, 7.50 mmol) in CH₂Cl₂ (25 ml) was stirred at room temperature overnight. Then it was washed with HCl 1 M (20 ml), saturated NaHCO₃ (20 ml) and brine (20 ml), dried over anhydrous Na₂SO₄ and the solvent was evaporated to give the crude product which was purified by column chromatography (eluent 10:1 EtOAc/EtOH) as off white crystals (yield 63%). mp: 399 - 401 K. IR (KBr, cm^-1): 1759 (CO, β-lactam), 1350, 1527 (NO₂). ¹H-NMR (CDCl₃) δ (p.p.m.): 1.72 (CH₂—CH₂—CH₂–, m, 2H), 2.44 (CH₂—CH₂—CH₂– and CH₂—N morpholine ring, m, 6H), 3.02 (CH₂—CH₂—CH₂–, m, 1H), 3.56 (CH₂—CH₂—CH₂– and CH₂—O morpholine ring, m, 5H), 5.18 (H-4, d, J = 4.4 Hz, 1H), 5.64 (H-3, d, J = 4.4 Hz, 1H), 8.84 (ArH, d, J = 8.9 Hz, 1H), 7.07 (ArH, s, 1H), 7.31–7.70 (ArH, m, 7H), 8.09 (ArH, d, J = 8.2 Hz, 1H), 8.24 (ArH, s, 1H). ¹³C-NMR (CDCl₃) δ (p.p.m.): 24.4 (CH₂—CH₂—CH₂–), 39.2 (CH₂—CH₂—CH₂–), 53.5 (CH₂—N morpholine ring), 56.0 (CH₂—CH₂—CH₂–), 61.4 (C-4), 66.7 (CH₂—O morpholine ring), 81.7 (C-3), 108.8, 117.9, 123.4, 123.8, 124.4, 126.6, 126.8, 127.6, 129.3, 129.5, 129.7, 133.8, 134.4, 135.8, 148.1, 154.2 (aromatic carbons), 165.5 (CO, β-lactam). MS m/z = 461 [M⁺]. Anal. Calcd. for C₂₆H₂₇N₃O₅: C 67.66, H 5.90, N 9.10%. Found: C 67.74, H 6.02, N 9.13%.