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

Ísmail Çelik; Mehmet Akkurt; Aliasghar Jarrahpour; Edris Ebrahimi; Orhan Büyükgüngör

doi:10.1107/S1600536809004255

. 2009 Feb 11;65(Pt 3):o501–o502. doi: 10.1107/S1600536809004255

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

Ísmail Çelik ^a, Mehmet Akkurt ^b,^*, Aliasghar Jarrahpour ^c, Edris Ebrahimi ^c, Orhan Büyükgüngör ^d

PMCID: PMC2968600 PMID: 21582166

Abstract

The β-lactam ring of the title compound, C₃₅H₂₃NO₂, is nearly planar with a maximum deviation of 0.003 (3) Å from the mean plane. It makes dihedral angles of 17.4 (2), 85.22 (17) and 65.39 (16)°, respectively, with the phenyl, xanthene and anthracene ring systems. In the crystal structure, there are intramolecular C—H⋯O and C—H⋯N contacts and molecules are also linked by C—H⋯π interactions.

Related literature

For general background on β-lactam antibiotics, see: Banik et al. (2003 ▶); Jarrahpour & Khalili (2007 ▶); Miller (2000 ▶); Palomo et al. (2004 ▶). For the crystal structures of related compounds, see: Akkurt, Jarrahpour et al. (2008 ▶); Akkurt, Karaca et al. (2008 ▶); Pınar et al. (2006 ▶). For geometric analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C₃₅H₂₃NO₂
M _r = 489.54
Monoclinic,
a = 13.6906 (8) Å
b = 13.3085 (7) Å
c = 17.3527 (10) Å
β = 127.548 (4)°
V = 2506.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 (2) K
0.24 × 0.18 × 0.14 mm

Data collection

STOE IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T _min = 0.981, T _max = 0.989
19631 measured reflections
5191 independent reflections
2442 reflections with I > 2σ(I)
R _int = 0.067

Refinement

R[F ² > 2σ(F ²)] = 0.051
wR(F ²) = 0.110
S = 0.90
5191 reflections
343 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.13 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/S1600536809004255/is2388sup1.cif

e-65-0o501-sup1.cif^{(30.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809004255/is2388Isup2.hkl

e-65-0o501-Isup2.hkl^{(249.1KB, hkl)}

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
C2—H2⋯N1	0.93	2.28	2.964 (4)	130
C31—H31⋯O2	0.93	2.48	3.092 (3)	124
C3—H3⋯Cg1ⁱ	0.93	2.86	3.601 (3)	138
C11—H11⋯Cg2ⁱⁱ	0.93	2.63	3.543 (3)	166

Open in a new tab

Symmetry codes: (i) Inline graphic ; (ii) . Cg1 and Cg2 are the centroids of the benzene ring (C8–C13) and phenyl ring (C30–C35), respectively.

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).

supplementary crystallographic information

Comment

The stereo selective synthesis of β-lactams has received considerable attention over recent years because of their wide variety of biological activities (Miller, 2000), in particular, asymmetric synthesis by means of a Staudinger ketene–imine reaction has been extensively studied (Palomo et al., 2004). Several syntheses of spiro-β-lactams are available in the literature (Jarrahpour & Khalili, 2007; Pınar et al., 2006; Akkurt, Jarrahpour et al., 2008; Akkurt, Karaca et al., 2008). The synthesis of polycyclic aromatic β-lactams from polyaromatic imines have been reported in literature (Banik et al., 2003).

The β-lactam unit in (I) (Fig. 1) is essentially planar, with a maximum deviation of 0.003 (3) Å from the mean plane. The β-lactam ring makes a dihedral angle of 17.4 (2)° with the phenyl ring C30—C35. In the xanthene ring system, attached at C16, the benzene rings (C17–C22) and (C23–C28) are almost planar, the dihedral angle between them 17.20 (14)°. Its central ring, C16/C17/C22/O1/C23/C28, is not planar, with puckering parameters: Q_T = 0.247 (3) Å, θ = 98.9 (7)° and φ = 355.1 (7)° (Cremer & Pople, 1975). The mean plane of the xanthene ring system forms the dihedral angles of 85.22 (17) and 85.62 (13)°, with the β-lactam ring and the phenyl ring, respectively. The anthracene ring system, attached at C15, is almost planar, with maximum deviations of 0.041 (2) Å for C1, -0.049 (3) Å for C4 and, -0.067 (2) Å for C13, makes dihedral angle of 65.39 (16), 80.60 (13) and 56.63 (8)°, with the β-lactam, the phenyl and the mean plane of the xanthene ring system, respectively.

In the crystal structure, there are intramolecular C—H···O and C—H···N contacts and molecules are linked to each other by C—H···π interactions between the adjacent molecules (Table 1 and Fig. 2) [Cg1 and Cg2 are the centroids of the benzene ring (C8–C13) and phenyl ring (C30–C35), respectively].

Experimental

A mixture of (E)—N-(antheracen-9-ylmethylene)aniline (0.30 g, 1.07 mmol) and triethylamine (0.73 g, 7.21 mmol), 9H-xanthen-9-carboxylic acid (0.49 g, 2.17 mmol) and tosyl chloride (0.42 g, 2.20 mmol) in CH₂Cl₂ (15 ml) was stirred at room temperature for 24 h. Then it was washed with HCl 1 N (20 ml) and saturated sodiumbicarbonate solution (20 ml), brine (20 ml), dried (Na₂SO₄) and the solvent was evaporated to give the crude product as a light yellow crystal which was then purified by recrystallization from ethyl acetate (Yield 63%). dec: 511–513 K. IR (KBr, cm^-1): 1758 (CO β-lactam). ¹H-NMR δ (p.p.m.): 6.34 (s, 1H, 4), 6.51–8.83 (m, ArH, 22H).¹³C-NMR δ (p.p.m.): 65.6 (C-3), 75.4 (C-4), 115.9–152.0 (aromatic carbon), 167.5 (CO β-lactam). Analysis calculated for C₃₅H₂₃NO₂: C 85.87, H 4.74, N 2.86%. Found: C 85.87, H 4.74, N 2.86%.