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

Mehmet Akkurt; Yılmaz Dağdemir; Aliasghar Jarrahpour; Maryam Rostami; Orhan Büyükgüngör

doi:10.1107/S1600536811000663

. 2011 Jan 12;67(Pt 2):o326–o327. doi: 10.1107/S1600536811000663

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

Mehmet Akkurt ^a,^*, Yılmaz Dağdemir ^a, Aliasghar Jarrahpour ^b, Maryam Rostami ^b, Orhan Büyükgüngör ^c

PMCID: PMC3051730 PMID: 21523012

Abstract

The central β-lactam ring of the title compound, C₂₃H₂₁NO₃, is almost planar (r.m.s. deviation = 0.032Å). The methoxybenzene ring is almost coplanar with the β-lactam ring [dihedral angle = 1.87 (11)°], whereas the tolyl ring is almost normal to it [75.73 (12)°]. The dihedral angle between the β-lactam ring and the O-bonded phenyl ring is 51.95 (12)°. An intramolecular C—H⋯O interaction generates an S(6) ring. The crystal structure features intermolecular C—H⋯O hydrogen bonds, forming layers parallel to (011), and weak C—H⋯π interactions. Two aromatic π–π stacking interactions [centroid–centroid distances = 3.6744 (12) and 3.6799 (11) Å] are also observed.

Related literature

For the synthesis of the title compound and background to the biological properties of β-lactam compounds, see: Jarrahpour & Zarei (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₃H₂₁NO₃
M _r = 359.41
Triclinic,
a = 6.0764 (3) Å
b = 9.9545 (5) Å
c = 16.4519 (10) Å
α = 104.360 (4)°
β = 91.261 (5)°
γ = 97.724 (4)°
V = 953.71 (9) Å³
Z = 2
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.60 × 0.37 × 0.12 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.964, T _max = 0.990
13748 measured reflections
3961 independent reflections
2608 reflections with I > 2σ(I)
R _int = 0.055

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.119
S = 1.03
3961 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.13 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: 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/S1600536811000663/hb5783sup1.cif

e-67-0o326-sup1.cif^{(22.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000663/hb5783Isup2.hkl

e-67-0o326-Isup2.hkl^{(194.1KB, hkl)}

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

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

Cg4 is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2	0.93	2.47	3.093 (2)	125
C9—H9⋯O2ⁱ	0.98	2.51	3.446 (2)	160
C15—H15⋯O1ⁱ	0.93	2.54	3.435 (2)	162
C19—H19⋯O2ⁱⁱ	0.93	2.54	3.415 (2)	156
C23—H23C⋯O2ⁱⁱⁱ	0.96	2.52	3.184 (2)	126
C5—H5⋯Cg4^iv	0.93	2.96	3.544 (3)	122

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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 MR thank the Shiraz University Research Council for financial support (grant 88-GR—SC-23).

supplementary crystallographic information

Comment

The title compound, (I), is a β-lactam derivative with potential biological properties (Jarrahpour & Zarei, 2010); we now describe its crystal structure. In the title compound (I), (Fig. 1), the β-lactam ring (N1/C7–C9) is nearly planar [r.m.s. deviation = 0.032Å]. The dihedral angles between the planes of the rings in (I) are given in Table 2. The molecular dimensions are normal and lie within expected values for corresponding bond distances and angles (Allen et al., 1987).

The molecular structure is stabilized by intramolecular C—H···O hydrogen bonds, forming an S(6) graph-set motif (Bernstein et al., 1995) (Table 1). In the crystal structure, molecules are linked via intermolecular C—H···O hydrogen bonds (Table 1, Fig. 2), forming layers parallel to the bc plane. In addition, C—H···π interactions and two π-π stacking interactions [Cg1···Cg3(x, y, z) = 3.6744 (12) Å and Cg4···Cg4(1 - x, 2 - y, 1 - z) = 3.6799 (11) Å, where Cg1, Cg3 and Cg4 are the centroids of the N1/C7–C9 β-lactam, the C10–C15 and C17–C22 benzene rings, respectively] contribute to the stabilization of the structure.

Experimental

The title compound was prepared as described by Jarrahpour & Zarei (2010) and colourless prisms of (I) were recrystallized from ethyl acetate.