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

Baktır, Z.; Akkurt, M.; Jarrahpour, A.; Heiran, R.

doi:10.1107/S1600536811003382

Volume 67
Part 2
Pages o537-o538
February 2011

Received 6 January 2011
Accepted 25 January 2011
Online 29 January 2011

Key indicators
Single-crystal X-ray study
T = 294 K
Mean (C-C) = 0.005 Å
R = 0.059
wR = 0.155
Data-to-parameter ratio = 14.8
Details

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

Zeliha Baktir,^a Mehmet Akkurt,^a ^* Aliasghar Jarrahpour ^b and Roghaye Heiran ^b

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title compound, C₂₂H₁₈N₂O₅, the four-membered [beta] -lactam ring is nearly planar, with a maximum deviation of 0.023 (2) Å for the N atom, and has long C-C distances of 1.525 (5) and 1.571 (5) Å. The mean plane of this group makes dihedral angles of 11.61 (19), 74.5 (2) and 72.3 (2)° with three aromatic rings. An intramolecular C-HO hydrogen bond occurs. The packing of the molecules in the crystal structure is governed mainly by intermolecular C-HO hydrogen-bonding and C-H [pi] stacking interactions. Furthermore, a [pi] - [pi] interaction [centroid-centroid distance = 3.6129 (19) Å] helps to stabilize the crystal structure.

Related literature

For general background to [beta] -lactams, see: Jubie et al. (2009); Mehta et al. (2010); Vatmurge et al. (2008); Von Nussbaum et al. (2006). For related structures, see: Akkurt et al. (2006); Ercan et al. (1996a,b); Kabak et al. (1999).

Experimental

Crystal data

C₂₂H₁₈N₂O₅
M_r = 390.38
Triclinic, $[P \overline 1]$
a = 7.7934 (4) Å
b = 11.2813 (3) Å
c = 11.8818 (2) Å
= 77.771 (4)°
= 80.948 (5)°
= 71.052 (4)°
V = 961.18 (6) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 294 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.981, T_max = 0.981
3928 measured reflections
3928 independent reflections
1872 reflections with I > 2(I)
R_int = 0.104

Refinement

R[F² > 2(F²)] = 0.059
wR(F²) = 0.155
S = 1.01
3927 reflections
265 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C1-C6 and C17-C22 benzene rings, respectively.

D-HA	D-H	HA	DA	D-HA
C1-H1O2	0.93	2.53	3.125 (4)	122
C2-H2O2ⁱ	0.93	2.59	3.464 (4)	156
C16-H16O4ⁱⁱ	0.93	2.52	3.164 (5)	126
C4-H4Cg4ⁱⁱⁱ	0.93	2.89	3.716 (4)	149
C9-H9Cg2^iv	0.98	2.55	3.463 (4)	154
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x-1, y, z; (iii) x, y-1, z; (iv) -x+1, -y+1, -z+2.

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2175 ).

Acknowledgements

ZB and MA thank the Unit of the Scientific Research Projects of Erciyes University, Turkey for the research grant FBD-10-2949 and for support of the data collection at Atatürk University, Turkey. AJ and RH also thank the Shiraz University Research Council for financial support (grant No. 89-GR-SC-23).

References

Akkurt, M., Karaca, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o866-o868.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.
Ercan, F., Ülkü, D. & Güner, V. (1996a). Acta Cryst. C52, 1779-1780.
Ercan, F., Ülkü, D. & Güner, V. (1996b). Z. Kristallogr. 211, 735-736.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
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Rigaku/MSC (2005). CrystalClear. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Vatmurge, N. S., Hazra, B. G., Pore, V. S., Shirazi, F., Chavan, P. S. & Deshpande, M. W. (2008). Bioorg. Med. Chem. Lett. 18, 2043-2047.
Von Nussbaum, F., Brands, M., Hinzen, B., Weigand, S. & Häbich, D. (2006). Angew. Chem. Int. Ed. 45, 5072-5129.

organic compounds