2-[1-(4-Ethoxy­phen­yl)-2-oxo-4-styryl­azetidin-3-yl]isoindoline-1,3-dione

Mehmet Akkurt; Selvi Karaca; Ali Asghar Jarrahpour; Maaroof Zarei; Orhan Büyükgüngör

doi:10.1107/S1600536808011586

. 2008 Apr 26;64(Pt 5):o924. doi: 10.1107/S1600536808011586

2-[1-(4-Ethoxyphenyl)-2-oxo-4-styrylazetidin-3-yl]isoindoline-1,3-dione

Mehmet Akkurt ^a,^*, Selvi Karaca ^a, Ali Asghar Jarrahpour ^b, Maaroof Zarei ^b, Orhan Büyükgüngör ^c

PMCID: PMC2961093 PMID: 21202405

Abstract

The title compound, C₂₇H₂₂N₂O₄, contains a nearly planar four-membered β-lactam ring, which makes dihedral angles of 74.64 (12), 1.70 (11) and 73.67 (12)° with the nine-membered ring system, the benzene ring and the phenyl ring, respectively. The crystal structure is stabilized by C—H⋯O and C—H⋯π interactions and a π–π interaction [centroid–centroid distance = 3.4505 (19) Å] is also present.

Related literature

For related structures, see: Pınar et al. (2006 ▶); Akkurt et al. (2007 ▶). For background, see: Halve et al. (2007 ▶); Aoyama et al. (2001 ▶). For related literature, see: Jarrahpour & Zarei (2007 ▶).

Experimental

Crystal data

C₂₇H₂₂N₂O₄
M _r = 438.47
Monoclinic,
a = 33.7560 (17) Å
b = 7.0403 (2) Å
c = 31.0482 (17) Å
β = 140.454 (3)°
V = 4698.0 (5) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 (2) K
0.53 × 0.45 × 0.14 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: none
22562 measured reflections
4934 independent reflections
3071 reflections with I > 2σ(I)
R _int = 0.052

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.099
S = 0.96
4934 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.11 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: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808011586/hb2715sup1.cif

e-64-0o924-sup1.cif^{(24.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808011586/hb2715Isup2.hkl

e-64-0o924-Isup2.hkl^{(236.9KB, 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
C3—H3⋯O1ⁱ	0.93	2.53	3.283 (3)	138
C5—H5⋯O3ⁱⁱ	0.93	2.47	3.257 (3)	142
C13—H13⋯O3	0.93	2.53	3.139 (2)	123
C20—H20⋯O2ⁱⁱⁱ	0.93	2.51	3.374 (2)	156
C9—H9⋯Cg1^iv	0.98	2.84	3.7938 (16)	166
C19—H19C⋯Cg2^v	0.96	2.82	3.633 (4)	143

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) ; (iv) ; (v) . Cg1 is the centroid of atoms C12–C17 and Cg2 is the centroid of atoms C2–C7.

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

Comment

The 2-azetidinone ring system is the common structural feature of a number of broad spectrum β-lactam antibiotics (Halve et al., 2007) and also possesses other pharmalogical properties (Aoyama et al., 2001). As part of our onging studies of such materials (Pınar et al., 2006; Akkurt et al., 2007), we now report the synthesis and structure of the title compound, (I), (Fig. 1).

The four-membered β-lactam ring in (I) is nearly planar, with maximum deviations of 0.022 (1) Å for N2 and -0.021 (2) Å for C10. Within the lactam ring, the bond lengths are similar to those observed in our previous studies (Pınar et al., 2006; Akkurt et al., 2007).

The four-membered β-lactam ring (N2/C9–C11) in (I) makes dihedral angles of 74.64 (12), 1.70 (11) and 73.67 (12)° with the nine-membered ring system (A: N1/C1–C8) {max. deviations from planarity = 0.048 (2) for N1 and -0.029 (3) Å for C2 and C7}, the benzene ring (B: C12–C17) and the phenyl ring (C: C22–C27), respectively. The other dihedral angles are A/B = 74.74 (9), A/C = 55.97 (11) and B/C = 74.84 (10)°. The sum of the bond angles about atom N2 is 360.0°.

The packing and hydrogen bonding of the title compound is shown in Fig. 2. The crystal structure is stabilized by inter- and intramolecular C—H···O interactions and C—H···π contacts (Table 1). Finally, an aromatic π—π stacking interaction {C_g3···C_g2(1 – x, 2 – y,1 – z) = 3.4505 (19)Å, where C_g3 is the centroid of the N1/C1/C2/C7/C8 five-membered ring} is observed in the crystal structure.

Experimental

A solution of Schiff base (4-cinnamylidene)-(4-ethoxyphenyl)amine (1.0 eq.) was stirred with Phthaloylglycine (1.5 eq.), p-toluenesulfonyl chloride (1.5 eq.) and triethylamine (5 eq.) in dry CH₂Cl₂ at room temperature. After 10 h, the mixture was washed with saturated sodium bicarbonate solution and brine, dried over sodium sulfate and the solvent was evaporated to give the crude product which was then purified by recrystalization from EtOAc (Jarrahpour & Zarei, 2007) [mp: 434 -436 K]. IR (CHCl₃) cm^-1: 1724.2, 1758.5 (CO, phth), 1774.7 (CO, β-lactam); ¹H NMR (250 MHz, CDCl₃) δ 1.37 (Me, t, 3H), 2.33 (Me, s, 3H), 3.97 (OCH₂, q, 2H), 5.03 (H-4, dd, 1H, J=5.5, 8.5), 5.68 (H-3, d, 1H, J=5.5), 6.32 (H-5, dd, J=8.5, 16.0), 6.85 (H-6, d, 1H, J=9.0), 7.19-7.82 (ArH, m, 13H); ¹³C NMR (62.9 MHz, CDCl₃) δ 14.78 (Me), 57.69 (OCH₂), 61.04 (C-4), 63.67 (C-3), 114.99-155.82 (C=C, aromatic carbons), 160.56 (CO, phth), 167.28 (CO, β-lactam); GC-MS m/z = 438 [M⁺]. Analysis calculated for C₂₇H₂₂N₂O₄: C 73.96, H 5.06, N 6.39%. Found: C 74.02, H 5.09, N 6.33%.