4-(9-Anthr­yl)-1-(2,4-dimethoxy­phen­yl)spiro­[azetidine-3,9′-xanthen]-2-one

Baktır, Z.; Akkurt, M.; Jarrahpour, A.; Ebrahimi, E.; Büyükgüngör, O.

doi:10.1107/S1600536809022739

Volume 65
Part 7
Pages o1623-o1624
July 2009

Received 30 May 2009
Accepted 13 June 2009
Online 20 June 2009

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R = 0.057
wR = 0.131
Data-to-parameter ratio = 15.6
Details

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

Zeliha Baktir,^a Mehmet Akkurt,^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

The title compound, C₃₇H₂₇NO₄, crystallizes with two molecules in the asymmetric unit. The [beta] -lactam ring of each molecule is very nearly planar, with maximum deviations of 0.001 (2) and 0.017 (2) Å in the two molecules. The crystal structure is stabilized by intermolecular C-HO and C-HN contacts, as well as by weak C-H [pi] interactions.

Related literature

For the biological properties of spiro- [beta] -lactams, see: Kobayashi et al. (1991); Sheehan et al. (1978); Skiles & McNeil (1990); Waldmann (1995). For polycyclic aromatic [beta] -lactams with anti-cancer activity, see: Banik et al. (2003, 2004); Becker & Banik (1998). For several syntheses of spiro- [beta] -lactams, see: Jarrahpoor & Khalili (2007). For the structural characterizations of some [beta] -lactam compounds, see: Akkurt et al. (2008a,b); Yalçin et al. (2009). For ring puckering analysis, see: Cremer & Pople (1975).

Experimental

Crystal data

C₃₇H₂₇NO₄
M_r = 549.60
Triclinic, $[P \overline 1]$
a = 12.3164 (6) Å
b = 13.1277 (7) Å
c = 18.4838 (11) Å
= 92.434 (5)°
= 109.236 (4)°
= 91.357 (4)°
V = 2816.9 (3) Å³
Z = 4
Mo K radiation
= 0.08 mm^-1
T = 295 K
0.35 × 0.32 × 0.28 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.971, T_max = 0.977
30264 measured reflections
11851 independent reflections
6076 reflections with I > 2(I)
R_int = 0.100

Refinement

R[F² > 2(F²)] = 0.057
wR(F²) = 0.131
S = 0.88
11851 reflections
762 parameters
2 restraints
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.23 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2N1	0.93	2.33	2.964 (3)	125
C2'-H2'N1'	0.93	2.31	2.957 (3)	126
C3-H3O4'ⁱ	0.93	2.59	3.484 (4)	163
C9-H9O1ⁱⁱ	0.93	2.56	3.458 (4)	164
C35-H35O2	0.93	2.58	3.132 (3)	119
C35-H35O2ⁱⁱⁱ	0.93	2.52	3.212 (3)	131
C35'-H35'O2'	0.93	2.52	3.106 (3)	121
C2-H2Cg1	0.93	2.59	3.188 (3)	122
C2'-H2'Cg15	0.93	2.62	3.196 (3)	121
Symmetry codes: (i) -x, -y+1, -z; (ii) -x+2, -y+2, -z; (iii) -x+1, -y+1, -z. Cg1 and Cg15 are the centroids of the N1/C15/C16/C29 and N1'/C15'/C16'/C29' rings, respectively.

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); 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: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2470 ).

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).

References

Akkurt, M., Jarrahpour, A., Ebrahimi, E., Gençaslan, M. & Büyükgüngör, O. (2008a). Acta Cryst. E64, o2466-o2467.
Akkurt, M., Karaca, S., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2008b). Acta Cryst. E64, o902-o903.
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Yalçin, S. P., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009). Acta Cryst. E65, o626-o627.

organic compounds