(IUCr) 4-(9-Anthryl)-1-(4-methoxyphenyl)spiro[azetidin-3,9'-xanthen]-2-one

Volume 64
Part 5
Pages o902-o903
May 2008

Received 12 April 2008
Accepted 18 April 2008
Online 26 April 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R = 0.062
wR = 0.134
Data-to-parameter ratio = 15.4
Details

4-(9-Anthryl)-1-(4-methoxyphenyl)spiro[azetidin-3,9'-xanthen]-2-one

Mehmet Akkurt,^a ^* Selvi Karaca,^a Aliasghar Jarrahpour,^b Edris Ebrahimi ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey,^bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, 55139 Samsun, Turkey
Correspondence e-mail: akkurt@erciyes.edu.tr

In the title molecule, C₃₆H₂₅NO₃, the [beta] -lactam ring is essentially planar, with a dihedral angle of 3.3 (2)° between the two separate three-atom N/C/C planes. The [beta] -lactam ring makes dihedral angles of 28.45 (14), 87.4 (1) and 51.8 (1)° with the mean planes of the benzene, xanthene and anthracene ring systems, respectively. In addition to a weak intramolecular C-HN hydrogen bond, the crystal structure is stabilized by two weak intermolecular C-HO hydrogen bonds.

Related literature

For related literature, see: Alonso et al. (2001, 2002); Bycroft et al. (1988); Fukuda & Endo (1988); Jarrahpour & Khalili (2007); Kambara & Tomioka (1999); Pinder & Weinreb (2003); Sheehan et al. (1978); Skiles & McNeil (1990); Akkurt et al. (2006, 2007); Nardelli (1995); Pinar et al. (2006); Allen et al. (1987); Cremer & Pople (1975); Spek (2003).

Experimental

Crystal data

C₃₆H₂₅NO₃
M_r = 519.57
Monoclinic, P 2₁ /c
a = 13.7629 (9) Å
b = 10.5845 (4) Å
c = 20.5777 (12) Å
= 114.768 (5)°
V = 2721.9 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 293 (2) K
0.61 × 0.33 × 0.16 mm

Data collection

Stoe IPDS-2 diffractometer
Absorption correction: none
19756 measured reflections
5559 independent reflections
3359 reflections with I > 2(I)
R_int = 0.100

Refinement

R[F² > 2(F²)] = 0.061
wR(F²) = 0.133
S = 1.03
5559 reflections
361 parameters
H-atom parameters constrained
_max = 0.13 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8O3ⁱ	0.93	2.41	3.317 (4)	164
C18-H18O1ⁱⁱ	0.93	2.58	3.419 (3)	150
C25-H25N1	0.93	2.28	2.916 (3)	125
Symmetry codes: (i) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+1, -z+1.

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 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: LH2616 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDS-2 diffractometer (purchased under grant F.279 of the University Research Fund). AJ and EE thank Shiraz University Research Council for financial support (grant No. 86-GR-SC-23).

References

Akkurt, M., Karaca, S., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o866-o868.
Akkurt, M., Yalçin, S. P., Jarrahpour, A. A., Nazari, M. & Büyükgüngör, O. (2007). Acta Cryst. E63, o3729-o3730.
Allen, F. H., Kennard, O., Watson, D., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Alonso, E., Del Pozo, C. & Gonzalez, J. (2002). Synlett, pp. 69-72.
Alonso, E., Lopez-Ortiz, F., DelPozo, C., Peralta, E., Macas, A. & Gonzalez, J. (2001). J. Org. Chem. 66, 6333-6338.
Altomare, A., Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Rizzi, R. (1999). J. Appl. Cryst. 32, 339-340.
Bycroft, B. M., Shute, R. E. & Begley, M. J. (1988). J. Chem. Soc. Chem. Commun. pp. 274-276.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Fukuda, H. & Endo, T. (1988). Tetrahedron Lett. 29, 2327-2328.
Jarrahpour, A. & Khalili, D. (2007). Tetrahedron Lett. 48, 7140-7143.
Kambara, T. & Tomioka, K. (1999). J. Org. Chem. 64, 9282-9285.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Pinar, S., Akkurt, M., Jarrahpour, A. A., Khalili, D. & Büyükgüngör, O. (2006). Acta Cryst. E62, o804-o806.
Pinder, J. L. & Weinreb, S. M. (2003). Tetrahedron Lett. 44, 4141-4143.
Sheehan, J. C., Chacko, E., Lo, Y. S., Ponzi, D. R. & Sato, E. (1978). J. Org. Chem. 43, 4856-4859.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Skiles, J. W. & McNeil, D. (1990). Tetrahedron Lett. 31, 7277-7280.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7-13.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

organic compounds