4-[4-(4-Chloro­benzo­yl)-2,3-diphenyl­isoxazolidin-5-yl]-1-(4-meth­oxy­phen­yl)-3-phenyl­azetidin-2-one

Sivasubramanian Suhitha; Thothadri Srinivasan; Ramanathan Prasanna; Raghavachary Raghunathan; Devadasan Velmurugan

doi:10.1107/S1600536812038123

. 2012 Sep 12;68(Pt 10):o2914. doi: 10.1107/S1600536812038123

4-[4-(4-Chlorobenzoyl)-2,3-diphenylisoxazolidin-5-yl]-1-(4-methoxyphenyl)-3-phenylazetidin-2-one

Sivasubramanian Suhitha ^a, Thothadri Srinivasan ^a, Ramanathan Prasanna ^b, Raghavachary Raghunathan ^b, Devadasan Velmurugan ^a,^*

PMCID: PMC3470261 PMID: 23125705

Abstract

In the title compound, C₃₈H₃₁ClN₂O₄, the isoxazole ring adopts an envelope conformation with the N atom as the flap. The crystal packing is stabilized by C—H⋯O hydrogen bonds, forming chains running along the c-axis direction.

Related literature

For general background to β-lactams, see: Jones et al. (1989 ▶); Brakhage (1998 ▶); Banik & Becker (2000 ▶). For a related structure, see: Sundaramoorthy et al. (2012 ▶).

Experimental

Crystal data

C₃₈H₃₁ClN₂O₄
M _r = 615.10
Monoclinic,
a = 10.1221 (10) Å
b = 17.4890 (17) Å
c = 17.7421 (18) Å
β = 98.150 (6)°
V = 3109.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.17 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T _min = 0.951, T _max = 0.967
23486 measured reflections
5491 independent reflections
3214 reflections with I > 2σ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.132
S = 0.99
5491 reflections
407 parameters
H-atom parameters constrained
Δρ_max = 0.29 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Data collection: APEX2 (Bruker, 2008 ▶); cell refinement: SAINT (Bruker, 2008 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812038123/bt6829sup1.cif

e-68-o2914-sup1.cif^{(38.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038123/bt6829Isup2.hkl

e-68-o2914-Isup2.hkl^{(263.5KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812038123/bt6829Isup3.cml

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
C19—H19⋯O2ⁱ	0.98	2.41	3.338 (3)	158
C21—H21⋯O2ⁱ	0.93	2.50	3.425 (4)	173
C37—H37⋯O1ⁱⁱ	0.93	2.58	3.407 (4)	148

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

Acknowledgments

The authors thank the TBI X–ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS thanks the DST for an Inspire fellowship.

supplementary crystallographic information

Comment

The role of β-lactam antibiotics is well known (Banik & Becker, 2000). The most commonly used β-lactam antibiotics for the therapy of infectious diseases are penicillin and cephalosporin (Brakhage, 1998). β-Lactam based antibiotics have been successfully used in the treatment of infectious diseases for many years (Jones et al., 1989). In view of potential applications, the crystal structure determination of the titled β-lactam derivative was carried out.

In the title compound (Fig. 1), the β-lactam ring makes a dihedral angle of 10.33 (14)° with a isoxazole ring (N2/03/C17/C18/C19), a dihedral angle of 40.33 (14)° with the methoxy phenyl ring and a dihedral angle of 70.05 (16)° with the unsubstited phenyl ring. The dihedral angle between the isoxazole ring and the unsubstited phenyl ring (C20/C21/C22/C23/C24/C25) is 81.42 (12)°, which shows that they are almost orthogonal to each other. The dihedral angle between the isoxazole ring and the unsubstited phenyl ring (C11/C12/C13/C14/C15/C16) is 80.38 (14)°, which shows that they are also almost orthogonal to each other. The isoxazole ring makes a dihedral angle of 40.35 (12)° with the chlorolophenyl ring.

The oxygen atom attached to the β-lactam ring deviates by -0.1871 (18)Å. The oxygen atom attached to the phenyl ring deviates by 0.0237 (21)Å. The packing of the crystal structure is stabilized by intermolecular C—H···O hydrogen bonds (Fig. 2). A related structure was published by Sundaramoorthy et al. (2012).

Experimental

To a solution of the N-benzylideneaniline oxide (1 mol) in dry acetonitrile (20 ml) was added (E)-4-(3-(4-chlorophenyl)-3-oxoprop-1-enyl) -1-(4-methoxyphenyl)-3-phenylazetidin-2-one (1 mol) under N₂ atmosphere. The reaction was refluxed for 48 hours. After the completion of the reaction the solvent was distilled off under reduced pressure and the crude product was purified by column chromatography using 9:1 mixture of hexane-ethyl acetate. Crystallization of the pure compound was done using 1:1 mixture of chloroform-ethyl acetate.