organic compounds
4-(9-Anthryl)-1-(4-methoxyphenyl)spiro[azetidin-3,9′-xanthen]-2-one
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 Mayıs University, 55139 Samsun, Turkey
*Correspondence e-mail: akkurt@erciyes.edu.tr
In the title molecule, C36H25NO3, the β-lactam ring is essentially planar, with a dihedral angle of 3.3 (2)° between the two separate three-atom N/C/C planes. The β-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—H⋯N hydrogen bond, the is stabilized by two weak intermolecular C—H⋯O 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); Pınar et al. (2006); Allen et al. (1987); Cremer & Pople (1975); Spek (2003).
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: X-AREA (Stoe & Cie, 2002); cell 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).
Supporting information
10.1107/S1600536808010908/lh2616sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808010908/lh2616Isup2.hkl
A mixture of the Schiff base (E)—N-(anthracen-9-ylmethylene)-4-methoxyaniline (0.3 g, 1.45 mmol) and triethylamine (0.73 g, 7.27 mmol), 9H-xanthen-9-carboxylic acid (0. 49 g, 2.18 mmol) and tosyl chloride (0.42 g, 2.18 mmol) in CH2Cl2 (15 ml) was strirred at room temperature for 24 h. Then it was washed with HCl 1 N (20 ml) and saturated sodium bicarbonate solution (20 ml), brine (20 ml), dried (Na2SO4) and the solvent was evaporated to give the crude product as light yellow crystals which was then purified by recrystalization from ethyl acetate (yield 25%) [m.p. 470–472 K]. IR (CHCl3, cm-1): 1747.0 (CO β-lactam). 1H-NMR d (p.p.m.): 3.64 7(s, 3H, OCH3), 6.298 (s, 1H, 4), 6.511–8.826(m, ArH, 21H). 13C-NMR d (p.p.m.): 64.35 (OCH3), 62.84 (C-3), 75.68 (C-4), 116–152 (aromatic carbon), 167.34 (CO β-lactam). Analysis calculated for C36H25NO3: C 83.22, H 4.85, N 2.70%. Found: C 83.95, H 4.90, N 2.82%.
H atoms were included in ideal positions and refined by using a riding model, with C–H = 0.93 Å for aromatic, 0.96 Å for methyl and 0.98 Å for methine, and with Uiso = 1.2 or 1.5Ueq(C).
During the
of the structure, electron density peaks were located that were believed to be disordered solvent molecules (water from reactio solvent). The SQUEEZE option in PLATON (Spek, 2003) indicated there was a solvent cavity of volume 34 Å3 containing approximately 1.5 electrons. In the final cycles of this contribution to the electron density was removed from the observed data. The density, the value, the molecular weight and the formula are given without taking into account the results obtained with the SQUEEZE option PLATON (Spek, 2003).Data collection: X-AREA (Stoe & Cie, 2002); cell
X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SIR97 (Altomare et al., 1999\bbr01); 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).C36H25NO3 | F(000) = 1088 |
Mr = 519.57 | Dx = 1.268 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23499 reflections |
a = 13.7629 (9) Å | θ = 1.5–28.1° |
b = 10.5845 (4) Å | µ = 0.08 mm−1 |
c = 20.5777 (12) Å | T = 293 K |
β = 114.768 (5)° | Prism, light yellow |
V = 2721.9 (3) Å3 | 0.61 × 0.33 × 0.16 mm |
Z = 4 |
Stoe IPDS-2 diffractometer | 3359 reflections with I > 2σ(I) |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | Rint = 0.100 |
Plane graphite monochromator | θmax = 26.5°, θmin = 1.6° |
Detector resolution: 6.67 pixels mm-1 | h = −17→17 |
ω scans | k = −13→13 |
19756 measured reflections | l = −25→25 |
5559 independent reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0486P)2] where P = (Fo2 + 2Fc2)/3 |
5559 reflections | (Δ/σ)max < 0.001 |
361 parameters | Δρmax = 0.13 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C36H25NO3 | V = 2721.9 (3) Å3 |
Mr = 519.57 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.7629 (9) Å | µ = 0.08 mm−1 |
b = 10.5845 (4) Å | T = 293 K |
c = 20.5777 (12) Å | 0.61 × 0.33 × 0.16 mm |
β = 114.768 (5)° |
Stoe IPDS-2 diffractometer | 3359 reflections with I > 2σ(I) |
19756 measured reflections | Rint = 0.100 |
5559 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.13 e Å−3 |
5559 reflections | Δρmin = −0.18 e Å−3 |
361 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F^2^ for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > σ(F^2^) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.30826 (12) | 0.47676 (17) | 0.36036 (9) | 0.0580 (6) | |
O2 | 0.01260 (12) | 0.56344 (18) | 0.12243 (10) | 0.0629 (6) | |
O3 | 0.70434 (13) | 0.89046 (19) | 0.54334 (10) | 0.0671 (7) | |
N1 | 0.36864 (12) | 0.65460 (17) | 0.32002 (9) | 0.0408 (6) | |
C1 | 0.19804 (16) | 0.4947 (2) | 0.18251 (11) | 0.0405 (7) | |
C2 | 0.27536 (18) | 0.4117 (2) | 0.17982 (13) | 0.0502 (8) | |
C3 | 0.2530 (2) | 0.3274 (3) | 0.12490 (15) | 0.0610 (10) | |
C4 | 0.1512 (2) | 0.3219 (3) | 0.07022 (15) | 0.0668 (10) | |
C5 | 0.0726 (2) | 0.4008 (3) | 0.07171 (14) | 0.0611 (9) | |
C6 | 0.09628 (17) | 0.4865 (2) | 0.12622 (12) | 0.0475 (8) | |
C7 | 0.02358 (17) | 0.6316 (2) | 0.18153 (15) | 0.0544 (9) | |
C8 | −0.06802 (19) | 0.6919 (3) | 0.17835 (19) | 0.0781 (10) | |
C9 | −0.0640 (2) | 0.7611 (4) | 0.2355 (2) | 0.0939 (15) | |
C10 | 0.0301 (2) | 0.7712 (4) | 0.2973 (2) | 0.0964 (15) | |
C11 | 0.1208 (2) | 0.7119 (3) | 0.29880 (17) | 0.0729 (10) | |
C12 | 0.12027 (16) | 0.6437 (2) | 0.24156 (13) | 0.0489 (8) | |
C13 | 0.22163 (15) | 0.5893 (2) | 0.24046 (12) | 0.0412 (7) | |
C14 | 0.30342 (16) | 0.5552 (2) | 0.31672 (12) | 0.0410 (7) | |
C15 | 0.30515 (15) | 0.7010 (2) | 0.24693 (11) | 0.0401 (7) | |
C16 | 0.45290 (15) | 0.7156 (2) | 0.37759 (11) | 0.0397 (7) | |
C17 | 0.52326 (16) | 0.6478 (2) | 0.43596 (12) | 0.0466 (8) | |
C18 | 0.60597 (16) | 0.7098 (2) | 0.49038 (12) | 0.0501 (8) | |
C19 | 0.61856 (16) | 0.8382 (2) | 0.48725 (12) | 0.0474 (8) | |
C20 | 0.54858 (18) | 0.9063 (3) | 0.43031 (14) | 0.0578 (8) | |
C21 | 0.46607 (17) | 0.8438 (3) | 0.37511 (14) | 0.0572 (8) | |
C22 | 0.7252 (2) | 1.0209 (3) | 0.53897 (18) | 0.0848 (11) | |
C23 | 0.35611 (16) | 0.7107 (2) | 0.19465 (11) | 0.0416 (7) | |
C24 | 0.46163 (17) | 0.6711 (2) | 0.20799 (12) | 0.0447 (7) | |
C25 | 0.52860 (17) | 0.5941 (2) | 0.26651 (13) | 0.0498 (8) | |
C26 | 0.63122 (19) | 0.5661 (2) | 0.27846 (16) | 0.0589 (9) | |
C27 | 0.6760 (2) | 0.6116 (3) | 0.23318 (18) | 0.0672 (10) | |
C28 | 0.6161 (2) | 0.6794 (3) | 0.17531 (18) | 0.0676 (11) | |
C29 | 0.50704 (19) | 0.7110 (2) | 0.15967 (14) | 0.0535 (9) | |
C30 | 0.4453 (2) | 0.7773 (3) | 0.09829 (16) | 0.0650 (10) | |
C31 | 0.3389 (2) | 0.8062 (3) | 0.08063 (14) | 0.0609 (9) | |
C32 | 0.2736 (3) | 0.8687 (3) | 0.01526 (17) | 0.0853 (13) | |
C33 | 0.1714 (3) | 0.8974 (4) | −0.00129 (18) | 0.0953 (15) | |
C34 | 0.1254 (2) | 0.8668 (3) | 0.04666 (17) | 0.0819 (11) | |
C35 | 0.18394 (19) | 0.8077 (3) | 0.11000 (14) | 0.0622 (9) | |
C36 | 0.29327 (18) | 0.7731 (2) | 0.12966 (13) | 0.0500 (8) | |
H2 | 0.34400 | 0.41390 | 0.21640 | 0.0600* | |
H3 | 0.30630 | 0.27400 | 0.12440 | 0.0730* | |
H4 | 0.13580 | 0.26510 | 0.03270 | 0.0800* | |
H5 | 0.00350 | 0.39590 | 0.03580 | 0.0730* | |
H8 | −0.13180 | 0.68530 | 0.13750 | 0.0940* | |
H9 | −0.12520 | 0.80210 | 0.23290 | 0.1130* | |
H10 | 0.03220 | 0.81640 | 0.33660 | 0.1150* | |
H11 | 0.18440 | 0.71840 | 0.33990 | 0.0870* | |
H15 | 0.27310 | 0.78260 | 0.24940 | 0.0480* | |
H17 | 0.51490 | 0.56100 | 0.43850 | 0.0560* | |
H18 | 0.65350 | 0.66430 | 0.52940 | 0.0600* | |
H20 | 0.55610 | 0.99340 | 0.42850 | 0.0690* | |
H21 | 0.41910 | 0.88950 | 0.33590 | 0.0690* | |
H22A | 0.66410 | 1.06950 | 0.53510 | 0.1020* | |
H22B | 0.73910 | 1.03550 | 0.49760 | 0.1020* | |
H22C | 0.78640 | 1.04570 | 0.58120 | 0.1020* | |
H25 | 0.50130 | 0.56190 | 0.29750 | 0.0600* | |
H26 | 0.67230 | 0.51580 | 0.31740 | 0.0710* | |
H27 | 0.74720 | 0.59480 | 0.24330 | 0.0810* | |
H28 | 0.64560 | 0.70650 | 0.14450 | 0.0810* | |
H30 | 0.47600 | 0.80320 | 0.06790 | 0.0780* | |
H32 | 0.30300 | 0.88990 | −0.01660 | 0.1020* | |
H33 | 0.13040 | 0.93760 | −0.04430 | 0.1150* | |
H34 | 0.05430 | 0.88710 | 0.03480 | 0.0980* | |
H35 | 0.15240 | 0.78970 | 0.14100 | 0.0750* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0620 (10) | 0.0613 (11) | 0.0500 (10) | −0.0043 (8) | 0.0228 (8) | 0.0149 (9) |
O2 | 0.0431 (8) | 0.0711 (12) | 0.0598 (11) | 0.0029 (8) | 0.0070 (8) | −0.0105 (10) |
O3 | 0.0571 (10) | 0.0691 (13) | 0.0525 (11) | −0.0128 (9) | 0.0007 (8) | −0.0011 (10) |
N1 | 0.0390 (9) | 0.0453 (11) | 0.0344 (10) | −0.0005 (8) | 0.0117 (7) | 0.0030 (9) |
C1 | 0.0445 (11) | 0.0412 (12) | 0.0388 (12) | −0.0027 (9) | 0.0203 (10) | 0.0034 (10) |
C2 | 0.0519 (12) | 0.0503 (14) | 0.0499 (14) | 0.0033 (11) | 0.0229 (11) | 0.0037 (12) |
C3 | 0.0782 (17) | 0.0555 (16) | 0.0585 (17) | 0.0071 (13) | 0.0376 (14) | 0.0002 (14) |
C4 | 0.0913 (19) | 0.0581 (17) | 0.0512 (16) | −0.0055 (15) | 0.0302 (15) | −0.0113 (14) |
C5 | 0.0646 (15) | 0.0624 (17) | 0.0487 (16) | −0.0079 (13) | 0.0163 (12) | −0.0054 (14) |
C6 | 0.0483 (12) | 0.0487 (14) | 0.0427 (13) | −0.0020 (10) | 0.0164 (10) | 0.0013 (11) |
C7 | 0.0411 (12) | 0.0551 (15) | 0.0635 (17) | −0.0023 (10) | 0.0186 (11) | −0.0073 (13) |
C8 | 0.0388 (13) | 0.077 (2) | 0.105 (2) | 0.0015 (12) | 0.0170 (14) | −0.0199 (19) |
C9 | 0.0497 (15) | 0.101 (3) | 0.131 (3) | 0.0073 (16) | 0.0379 (18) | −0.034 (2) |
C10 | 0.0661 (18) | 0.119 (3) | 0.111 (3) | 0.0072 (18) | 0.0440 (19) | −0.046 (2) |
C11 | 0.0538 (14) | 0.093 (2) | 0.0724 (19) | 0.0040 (14) | 0.0269 (13) | −0.0246 (18) |
C12 | 0.0409 (11) | 0.0514 (14) | 0.0544 (15) | −0.0019 (10) | 0.0200 (11) | −0.0039 (12) |
C13 | 0.0374 (10) | 0.0424 (13) | 0.0452 (13) | −0.0009 (9) | 0.0187 (9) | 0.0025 (11) |
C14 | 0.0427 (11) | 0.0432 (13) | 0.0393 (12) | 0.0028 (9) | 0.0193 (9) | 0.0072 (11) |
C15 | 0.0396 (10) | 0.0417 (13) | 0.0342 (11) | 0.0030 (9) | 0.0107 (9) | 0.0030 (10) |
C16 | 0.0373 (10) | 0.0465 (13) | 0.0353 (11) | 0.0003 (9) | 0.0151 (9) | 0.0018 (10) |
C17 | 0.0476 (12) | 0.0470 (14) | 0.0418 (13) | 0.0044 (10) | 0.0155 (10) | 0.0083 (11) |
C18 | 0.0444 (12) | 0.0609 (17) | 0.0370 (12) | 0.0066 (11) | 0.0091 (10) | 0.0085 (12) |
C19 | 0.0414 (11) | 0.0572 (15) | 0.0377 (13) | −0.0024 (10) | 0.0109 (10) | 0.0001 (12) |
C20 | 0.0557 (13) | 0.0469 (14) | 0.0564 (16) | −0.0039 (11) | 0.0093 (12) | 0.0038 (13) |
C21 | 0.0503 (13) | 0.0522 (15) | 0.0494 (15) | 0.0028 (11) | 0.0014 (11) | 0.0087 (13) |
C22 | 0.0686 (17) | 0.068 (2) | 0.087 (2) | −0.0150 (15) | 0.0023 (16) | −0.0109 (18) |
C23 | 0.0483 (11) | 0.0382 (12) | 0.0361 (12) | −0.0086 (9) | 0.0155 (10) | 0.0005 (10) |
C24 | 0.0495 (12) | 0.0405 (12) | 0.0464 (13) | −0.0090 (10) | 0.0223 (10) | −0.0063 (11) |
C25 | 0.0504 (12) | 0.0452 (14) | 0.0574 (15) | −0.0021 (10) | 0.0261 (11) | −0.0039 (12) |
C26 | 0.0509 (13) | 0.0504 (15) | 0.0765 (19) | −0.0004 (11) | 0.0279 (13) | −0.0082 (14) |
C27 | 0.0555 (14) | 0.0589 (17) | 0.095 (2) | −0.0077 (13) | 0.0391 (16) | −0.0127 (17) |
C28 | 0.0736 (17) | 0.0611 (18) | 0.092 (2) | −0.0195 (14) | 0.0583 (17) | −0.0172 (17) |
C29 | 0.0673 (15) | 0.0474 (14) | 0.0562 (16) | −0.0163 (12) | 0.0362 (13) | −0.0095 (13) |
C30 | 0.0866 (19) | 0.0606 (17) | 0.0637 (18) | −0.0179 (15) | 0.0470 (15) | −0.0037 (15) |
C31 | 0.0885 (18) | 0.0510 (16) | 0.0431 (14) | −0.0162 (14) | 0.0275 (13) | −0.0003 (13) |
C32 | 0.115 (3) | 0.084 (2) | 0.0501 (18) | −0.009 (2) | 0.0279 (17) | 0.0168 (17) |
C33 | 0.113 (3) | 0.094 (3) | 0.0505 (19) | 0.000 (2) | 0.0063 (18) | 0.0278 (19) |
C34 | 0.0733 (18) | 0.083 (2) | 0.0619 (19) | −0.0001 (16) | 0.0013 (15) | 0.0228 (17) |
C35 | 0.0605 (14) | 0.0600 (17) | 0.0518 (15) | −0.0072 (12) | 0.0096 (12) | 0.0109 (14) |
C36 | 0.0583 (13) | 0.0452 (14) | 0.0382 (13) | −0.0091 (11) | 0.0121 (10) | 0.0006 (11) |
O1—C14 | 1.204 (3) | C26—C27 | 1.400 (4) |
O2—C6 | 1.386 (3) | C27—C28 | 1.338 (5) |
O2—C7 | 1.367 (3) | C28—C29 | 1.437 (4) |
O3—C19 | 1.375 (3) | C29—C30 | 1.382 (4) |
O3—C22 | 1.421 (4) | C30—C31 | 1.387 (4) |
N1—C14 | 1.366 (3) | C31—C32 | 1.429 (4) |
N1—C15 | 1.472 (3) | C31—C36 | 1.437 (4) |
N1—C16 | 1.419 (3) | C32—C33 | 1.336 (6) |
C1—C2 | 1.399 (3) | C33—C34 | 1.415 (5) |
C1—C6 | 1.397 (3) | C34—C35 | 1.364 (4) |
C1—C13 | 1.485 (3) | C35—C36 | 1.432 (4) |
C2—C3 | 1.370 (4) | C2—H2 | 0.9300 |
C3—C4 | 1.383 (4) | C3—H3 | 0.9300 |
C4—C5 | 1.377 (4) | C4—H4 | 0.9300 |
C5—C6 | 1.372 (4) | C5—H5 | 0.9300 |
C7—C8 | 1.390 (4) | C8—H8 | 0.9300 |
C7—C12 | 1.391 (4) | C9—H9 | 0.9300 |
C8—C9 | 1.367 (5) | C10—H10 | 0.9300 |
C9—C10 | 1.388 (5) | C11—H11 | 0.9300 |
C10—C11 | 1.386 (5) | C15—H15 | 0.9800 |
C11—C12 | 1.379 (4) | C17—H17 | 0.9300 |
C12—C13 | 1.518 (3) | C18—H18 | 0.9300 |
C13—C14 | 1.543 (3) | C20—H20 | 0.9300 |
C13—C15 | 1.615 (3) | C21—H21 | 0.9300 |
C15—C23 | 1.514 (3) | C22—H22A | 0.9600 |
C16—C17 | 1.386 (3) | C22—H22B | 0.9600 |
C16—C21 | 1.373 (4) | C22—H22C | 0.9600 |
C17—C18 | 1.383 (3) | C25—H25 | 0.9300 |
C18—C19 | 1.375 (3) | C26—H26 | 0.9300 |
C19—C20 | 1.369 (4) | C27—H27 | 0.9300 |
C20—C21 | 1.392 (4) | C28—H28 | 0.9300 |
C23—C24 | 1.423 (3) | C30—H30 | 0.9300 |
C23—C36 | 1.416 (3) | C32—H32 | 0.9300 |
C24—C25 | 1.426 (3) | C33—H33 | 0.9300 |
C24—C29 | 1.442 (4) | C34—H34 | 0.9300 |
C25—C26 | 1.361 (4) | C35—H35 | 0.9300 |
O1···C17 | 3.255 (3) | C25···H2 | 2.9900 |
O1···C18i | 3.419 (3) | C25···H3viii | 3.0900 |
O3···C8ii | 3.317 (4) | C26···H3viii | 2.8500 |
O1···H17 | 2.7600 | C26···H21v | 2.8500 |
O1···H18i | 2.5800 | C27···H21v | 2.7800 |
O2···H10iii | 2.8900 | C28···H21v | 3.1000 |
O3···H8ii | 2.4100 | C29···H20v | 2.8300 |
O3···H28iv | 2.7300 | C30···H20v | 3.0500 |
N1···C11 | 3.308 (4) | C35···H26viii | 2.9200 |
N1···C25 | 2.916 (3) | C35···H15 | 2.6200 |
N1···H11 | 2.8100 | C36···H26viii | 2.7500 |
N1···H25 | 2.2800 | H2···C14 | 2.7900 |
C1···C36 | 3.575 (3) | H2···C25 | 2.9900 |
C2···C23 | 3.326 (3) | H3···C19v | 2.9700 |
C2···C27v | 3.569 (4) | H3···C20v | 3.0200 |
C3···C19v | 3.447 (4) | H3···C25v | 3.0900 |
C3···C20v | 3.471 (4) | H3···C26v | 2.8500 |
C3···C26v | 3.389 (4) | H5···C5vi | 2.9500 |
C3···C27v | 3.509 (4) | H8···O3vii | 2.4100 |
C5···C5vi | 3.489 (4) | H8···C22vii | 3.0700 |
C8···O3vii | 3.317 (4) | H10···O2ix | 2.8900 |
C11···N1 | 3.308 (4) | H10···C5ix | 2.9500 |
C13···C35 | 3.414 (4) | H10···C6ix | 2.8400 |
C16···C24 | 3.573 (3) | H11···N1 | 2.8100 |
C16···C25 | 3.156 (3) | H11···C14 | 2.5600 |
C17···O1 | 3.255 (3) | H11···C15 | 3.0200 |
C17···C25 | 3.564 (3) | H15···C11 | 2.7900 |
C18···O1i | 3.419 (3) | H15···C21 | 2.9000 |
C19···C3viii | 3.447 (4) | H15···C35 | 2.6200 |
C20···C3viii | 3.471 (4) | H15···H21 | 2.3400 |
C23···C2 | 3.326 (3) | H15···H35 | 2.1500 |
C24···C16 | 3.573 (3) | H17···O1 | 2.7600 |
C25···C17 | 3.564 (3) | H17···C14 | 2.9400 |
C25···C16 | 3.156 (3) | H18···O1i | 2.5800 |
C25···N1 | 2.916 (3) | H20···C22 | 2.5000 |
C26···C36v | 3.553 (3) | H20···H22A | 2.2200 |
C26···C3viii | 3.389 (4) | H20···H22B | 2.3600 |
C27···C3viii | 3.509 (4) | H20···C29viii | 2.8300 |
C27···C2viii | 3.569 (4) | H20···C30viii | 3.0500 |
C35···C13 | 3.414 (4) | H21···C15 | 2.7200 |
C36···C26viii | 3.553 (3) | H21···H15 | 2.3400 |
C36···C1 | 3.575 (3) | H21···C26viii | 2.8500 |
C5···H5vi | 2.9500 | H21···C27viii | 2.7800 |
C5···H10iii | 2.9500 | H21···C28viii | 3.1000 |
C6···H10iii | 2.8400 | H22A···C20 | 2.7000 |
C7···H35 | 2.8100 | H22A···H20 | 2.2200 |
C11···H15 | 2.7900 | H22B···C20 | 2.7600 |
C12···H35 | 2.7600 | H22B···H20 | 2.3600 |
C13···H35 | 2.8200 | H25···N1 | 2.2800 |
C14···H25 | 2.9100 | H25···C14 | 2.9100 |
C14···H11 | 2.5600 | H25···C15 | 2.8600 |
C14···H17 | 2.9400 | H25···C16 | 2.5900 |
C14···H2 | 2.7900 | H25···C17 | 2.8800 |
C15···H21 | 2.7200 | H26···C35v | 2.9200 |
C15···H35 | 2.4900 | H26···C36v | 2.7500 |
C15···H25 | 2.8600 | H28···H30 | 2.4300 |
C15···H11 | 3.0200 | H28···O3x | 2.7300 |
C16···H25 | 2.5900 | H30···H28 | 2.4300 |
C17···H30iv | 3.0900 | H30···H32 | 2.4600 |
C17···H25 | 2.8800 | H30···C17x | 3.0900 |
C18···H30iv | 2.8600 | H30···C18x | 2.8600 |
C19···H3viii | 2.9700 | H32···H30 | 2.4600 |
C20···H22A | 2.7000 | H35···C7 | 2.8100 |
C20···H3viii | 3.0200 | H35···C12 | 2.7600 |
C20···H22B | 2.7600 | H35···C13 | 2.8200 |
C21···H15 | 2.9000 | H35···C15 | 2.4900 |
C22···H8ii | 3.0700 | H35···H15 | 2.1500 |
C22···H20 | 2.5000 | ||
C6—O2—C7 | 118.7 (2) | C30—C31—C32 | 121.8 (3) |
C19—O3—C22 | 117.6 (2) | C30—C31—C36 | 119.1 (3) |
C14—N1—C15 | 96.30 (16) | C32—C31—C36 | 119.1 (3) |
C14—N1—C16 | 133.00 (18) | C31—C32—C33 | 121.7 (3) |
C15—N1—C16 | 128.98 (18) | C32—C33—C34 | 120.1 (3) |
C2—C1—C6 | 116.3 (2) | C33—C34—C35 | 120.9 (3) |
C2—C1—C13 | 122.8 (2) | C34—C35—C36 | 121.2 (3) |
C6—C1—C13 | 120.9 (2) | C23—C36—C31 | 120.2 (2) |
C1—C2—C3 | 122.0 (2) | C23—C36—C35 | 122.7 (2) |
C2—C3—C4 | 120.0 (3) | C31—C36—C35 | 117.1 (2) |
C3—C4—C5 | 119.6 (3) | C1—C2—H2 | 119.00 |
C4—C5—C6 | 120.0 (3) | C3—C2—H2 | 119.00 |
O2—C6—C1 | 122.1 (2) | C2—C3—H3 | 120.00 |
O2—C6—C5 | 115.8 (2) | C4—C3—H3 | 120.00 |
C1—C6—C5 | 122.1 (2) | C3—C4—H4 | 120.00 |
O2—C7—C8 | 116.1 (3) | C5—C4—H4 | 120.00 |
O2—C7—C12 | 123.1 (2) | C4—C5—H5 | 120.00 |
C8—C7—C12 | 120.7 (3) | C6—C5—H5 | 120.00 |
C7—C8—C9 | 119.8 (3) | C7—C8—H8 | 120.00 |
C8—C9—C10 | 121.0 (3) | C9—C8—H8 | 120.00 |
C9—C10—C11 | 118.1 (3) | C8—C9—H9 | 119.00 |
C10—C11—C12 | 122.4 (3) | C10—C9—H9 | 119.00 |
C7—C12—C11 | 117.9 (2) | C9—C10—H10 | 121.00 |
C7—C12—C13 | 119.7 (2) | C11—C10—H10 | 121.00 |
C11—C12—C13 | 122.4 (2) | C10—C11—H11 | 119.00 |
C1—C13—C12 | 112.00 (19) | C12—C11—H11 | 119.00 |
C1—C13—C14 | 118.68 (18) | N1—C15—H15 | 109.00 |
C1—C13—C15 | 117.93 (19) | C13—C15—H15 | 109.00 |
C12—C13—C14 | 110.92 (19) | C23—C15—H15 | 109.00 |
C12—C13—C15 | 110.36 (17) | C16—C17—H17 | 120.00 |
C14—C13—C15 | 84.07 (16) | C18—C17—H17 | 120.00 |
O1—C14—N1 | 131.6 (2) | C17—C18—H18 | 120.00 |
O1—C14—C13 | 135.1 (2) | C19—C18—H18 | 120.00 |
N1—C14—C13 | 93.13 (17) | C19—C20—H20 | 120.00 |
N1—C15—C13 | 86.41 (15) | C21—C20—H20 | 120.00 |
N1—C15—C23 | 119.70 (19) | C16—C21—H21 | 119.00 |
C13—C15—C23 | 121.11 (18) | C20—C21—H21 | 120.00 |
N1—C16—C17 | 121.18 (19) | O3—C22—H22A | 109.00 |
N1—C16—C21 | 119.6 (2) | O3—C22—H22B | 109.00 |
C17—C16—C21 | 119.3 (2) | O3—C22—H22C | 109.00 |
C16—C17—C18 | 119.7 (2) | H22A—C22—H22B | 109.00 |
C17—C18—C19 | 120.6 (2) | H22A—C22—H22C | 110.00 |
O3—C19—C18 | 116.1 (2) | H22B—C22—H22C | 109.00 |
O3—C19—C20 | 123.7 (2) | C24—C25—H25 | 119.00 |
C18—C19—C20 | 120.2 (2) | C26—C25—H25 | 119.00 |
C19—C20—C21 | 119.3 (3) | C25—C26—H26 | 119.00 |
C16—C21—C20 | 121.0 (3) | C27—C26—H26 | 119.00 |
C15—C23—C24 | 125.59 (19) | C26—C27—H27 | 120.00 |
C15—C23—C36 | 114.9 (2) | C28—C27—H27 | 120.00 |
C24—C23—C36 | 119.3 (2) | C27—C28—H28 | 119.00 |
C23—C24—C25 | 125.3 (2) | C29—C28—H28 | 119.00 |
C23—C24—C29 | 118.9 (2) | C29—C30—H30 | 119.00 |
C25—C24—C29 | 115.9 (2) | C31—C30—H30 | 119.00 |
C24—C25—C26 | 122.1 (2) | C31—C32—H32 | 119.00 |
C25—C26—C27 | 121.2 (3) | C33—C32—H32 | 119.00 |
C26—C27—C28 | 119.9 (3) | C32—C33—H33 | 120.00 |
C27—C28—C29 | 121.4 (3) | C34—C33—H33 | 120.00 |
C24—C29—C28 | 119.4 (2) | C33—C34—H34 | 120.00 |
C24—C29—C30 | 120.1 (3) | C35—C34—H34 | 120.00 |
C28—C29—C30 | 120.5 (3) | C34—C35—H35 | 119.00 |
C29—C30—C31 | 121.9 (3) | C36—C35—H35 | 119.00 |
C7—O2—C6—C5 | 166.4 (2) | C12—C13—C14—N1 | −107.24 (19) |
C6—O2—C7—C8 | −170.7 (2) | C1—C13—C14—N1 | 121.0 (2) |
C7—O2—C6—C1 | −12.9 (3) | C1—C13—C15—N1 | −121.6 (2) |
C6—O2—C7—C12 | 10.6 (3) | C15—C13—C14—N1 | 2.31 (16) |
C22—O3—C19—C18 | 174.8 (2) | C14—C13—C15—N1 | −2.15 (15) |
C22—O3—C19—C20 | −4.6 (4) | C14—C13—C15—C23 | 120.7 (2) |
C15—N1—C16—C17 | −162.1 (2) | C12—C13—C15—C23 | −129.2 (2) |
C15—N1—C14—C13 | −2.54 (18) | C15—C13—C14—O1 | 178.3 (3) |
C14—N1—C16—C21 | −144.4 (3) | C13—C15—C23—C24 | −101.0 (3) |
C16—N1—C15—C13 | −164.0 (2) | C13—C15—C23—C36 | 83.6 (2) |
C16—N1—C14—C13 | 163.0 (2) | N1—C15—C23—C24 | 4.0 (3) |
C14—N1—C15—C13 | 2.43 (17) | N1—C15—C23—C36 | −171.31 (19) |
C16—N1—C15—C23 | 72.0 (3) | N1—C16—C21—C20 | −179.3 (2) |
C15—N1—C14—O1 | −178.8 (3) | C17—C16—C21—C20 | −0.2 (4) |
C16—N1—C14—O1 | −13.3 (4) | N1—C16—C17—C18 | 178.5 (2) |
C14—N1—C15—C23 | −121.6 (2) | C21—C16—C17—C18 | −0.6 (4) |
C14—N1—C16—C17 | 36.5 (4) | C16—C17—C18—C19 | 0.4 (4) |
C15—N1—C16—C21 | 17.0 (3) | C17—C18—C19—C20 | 0.5 (4) |
C2—C1—C13—C14 | −34.3 (3) | C17—C18—C19—O3 | −178.9 (2) |
C6—C1—C13—C15 | −113.7 (2) | O3—C19—C20—C21 | 178.1 (2) |
C6—C1—C13—C14 | 147.3 (2) | C18—C19—C20—C21 | −1.3 (4) |
C13—C1—C6—C5 | 179.4 (2) | C19—C20—C21—C16 | 1.1 (4) |
C2—C1—C13—C12 | −165.6 (2) | C15—C23—C24—C25 | 13.0 (3) |
C2—C1—C13—C15 | 64.7 (3) | C15—C23—C24—C29 | −166.6 (2) |
C6—C1—C13—C12 | 16.0 (3) | C36—C23—C24—C25 | −171.8 (2) |
C2—C1—C6—C5 | 0.9 (3) | C36—C23—C24—C29 | 8.6 (3) |
C13—C1—C6—O2 | −1.4 (3) | C15—C23—C36—C31 | 170.1 (2) |
C2—C1—C6—O2 | −179.9 (2) | C15—C23—C36—C35 | −9.0 (3) |
C6—C1—C2—C3 | 0.4 (4) | C24—C23—C36—C31 | −5.6 (3) |
C13—C1—C2—C3 | −178.1 (2) | C24—C23—C36—C35 | 175.4 (2) |
C1—C2—C3—C4 | −0.5 (4) | C23—C24—C25—C26 | −175.9 (2) |
C2—C3—C4—C5 | −0.5 (5) | C29—C24—C25—C26 | 3.7 (3) |
C3—C4—C5—C6 | 1.7 (4) | C23—C24—C29—C28 | 175.5 (2) |
C4—C5—C6—C1 | −2.0 (4) | C23—C24—C29—C30 | −5.5 (3) |
C4—C5—C6—O2 | 178.8 (2) | C25—C24—C29—C28 | −4.1 (3) |
O2—C7—C8—C9 | 179.4 (3) | C25—C24—C29—C30 | 174.8 (2) |
O2—C7—C12—C11 | −178.2 (2) | C24—C25—C26—C27 | −0.3 (4) |
O2—C7—C12—C13 | 5.5 (3) | C25—C26—C27—C28 | −2.9 (4) |
C12—C7—C8—C9 | −1.8 (4) | C26—C27—C28—C29 | 2.3 (5) |
C8—C7—C12—C13 | −173.2 (2) | C27—C28—C29—C24 | 1.3 (4) |
C8—C7—C12—C11 | 3.2 (4) | C27—C28—C29—C30 | −177.7 (3) |
C7—C8—C9—C10 | −0.7 (5) | C24—C29—C30—C31 | −0.8 (4) |
C8—C9—C10—C11 | 1.7 (6) | C28—C29—C30—C31 | 178.2 (3) |
C9—C10—C11—C12 | −0.2 (5) | C29—C30—C31—C32 | −176.5 (3) |
C10—C11—C12—C7 | −2.2 (4) | C29—C30—C31—C36 | 3.9 (4) |
C10—C11—C12—C13 | 174.1 (3) | C30—C31—C32—C33 | −179.4 (3) |
C11—C12—C13—C15 | −60.6 (3) | C36—C31—C32—C33 | 0.2 (5) |
C7—C12—C13—C14 | −153.1 (2) | C30—C31—C36—C23 | −0.7 (4) |
C7—C12—C13—C1 | −18.0 (3) | C30—C31—C36—C35 | 178.4 (3) |
C11—C12—C13—C14 | 30.8 (3) | C32—C31—C36—C23 | 179.8 (2) |
C7—C12—C13—C15 | 115.6 (2) | C32—C31—C36—C35 | −1.2 (4) |
C11—C12—C13—C1 | 165.9 (2) | C31—C32—C33—C34 | 0.5 (5) |
C12—C13—C15—N1 | 107.99 (19) | C32—C33—C34—C35 | −0.2 (5) |
C1—C13—C15—C23 | 1.3 (3) | C33—C34—C35—C36 | −0.9 (5) |
C1—C13—C14—O1 | −63.0 (4) | C34—C35—C36—C23 | −179.4 (3) |
C12—C13—C14—O1 | 68.8 (3) | C34—C35—C36—C31 | 1.5 (4) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x+1, −y+3/2, z+1/2; (iii) −x, y−1/2, −z+1/2; (iv) x, −y+3/2, z+1/2; (v) −x+1, y−1/2, −z+1/2; (vi) −x, −y+1, −z; (vii) x−1, −y+3/2, z−1/2; (viii) −x+1, y+1/2, −z+1/2; (ix) −x, y+1/2, −z+1/2; (x) x, −y+3/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O3vii | 0.93 | 2.41 | 3.317 (4) | 164 |
C18—H18···O1i | 0.93 | 2.58 | 3.419 (3) | 150 |
C25—H25···N1 | 0.93 | 2.28 | 2.916 (3) | 125 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (vii) x−1, −y+3/2, z−1/2. |
Experimental details
Crystal data | |
Chemical formula | C36H25NO3 |
Mr | 519.57 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.7629 (9), 10.5845 (4), 20.5777 (12) |
β (°) | 114.768 (5) |
V (Å3) | 2721.9 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.61 × 0.33 × 0.16 |
Data collection | |
Diffractometer | Stoe IPDS2 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19756, 5559, 3359 |
Rint | 0.100 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.133, 1.03 |
No. of reflections | 5559 |
No. of parameters | 361 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.13, −0.18 |
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999\bbr01), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O3i | 0.93 | 2.41 | 3.317 (4) | 164 |
C18—H18···O1ii | 0.93 | 2.58 | 3.419 (3) | 150 |
C25—H25···N1 | 0.93 | 2.28 | 2.916 (3) | 125 |
Symmetry codes: (i) x−1, −y+3/2, z−1/2; (ii) −x+1, −y+1, −z+1. |
Acknowledgements
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). AJ and EE thank Shiraz University Research Council for financial support (grant No. 86-GR—SC-23).
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Although various examples of β-lactams with spiro structures derived from penicillins or cephalosporins have been reported (Bycroft et al., 1988), only a few examples of simple spiro β-lactams are known today (Fukuda & Endo, 1988; Jarrahpour & Khalili, 2007). Spiro cyclic β-lactams behave as β-turn mimetics (Alonso, Lopez-Ortiz et al., 2001), and as cholesterol absorption inhibitors (Kambara & Tomioka, 1999). They can act as antiviral (Skiles & McNeil, 1990), antibacterial agents (Sheehan et al., 1978), and they are precursors of α,α-disubstituted β-amino acids (Alonso et al., 2002). The spiranic β-lactam moiety is present in chartellines, a family of marine natural products (Pinder & Weinreb, 2003).
In the title molecule (Fig. 1), the bond lengths are within the normal ranges (Allen et al., 1987). The angles exocyclic to and those involving the β-lactam moiety (C13–C15/N1) are comparable with the values in our previously reported structures containing the β-lactam group (Pınar et al., 2006; Akkurt et al., 2007; Akkurt et al., 2006).
The β-lactam ring is nearly planar, with a maximum deviation of 0.017 (2) Å from the ring. The dihedral angle between the N1/C1/C2 and N1/C2/C3 planes is 176.7 (2)° (Nardelli, 1995). The planarity is mainly due to the sp2 hybridization of atoms C14 and N1. Atom O1 lies essentially in the β-lactam ring plane, with a deviation of -0.005 (2) Å. The dihedral angle between the benzene ring C16—C21 attached at N1 and the β-lactam ring is 28.45 (14)°.
In the xanthene ring system, attached at C13, the benzene rings (C1–C6) and (C7–C12) are almost co-planar, forming a dihedral angle of 12.4 (1)° with each other. The central ring, C1/C6/O2/C7/C12/C13, is not planar, with puckering parameters: QT = 0.195 (2) Å, θ = 100.8 (6)° and ϕ = 7.2 (8)° (Cremer & Pople, 1975). The mean planes of the xanthene ring system forms the dihedral angles of 87.4 (1)°, and 59.2 (1)°, with the β-lactam ring and the benzene ring C16–C21, respectively.
The anthracene ring system, attached at C15, is almost planar, with maximum deviations of 0.095 (2) Å for C23, -0.061 (2) Å for C25, -0.052 (2) Å for C26 and 0.041 (3) Å for C28. It forms dihedral angles of 51.8 (1)°, 74.2 (1)° and 62.91 (7)°, with the β-lactam ring, benzene ring (C16–C21) and the mean plane of the xanthene ring system, respectively.
The crystal structure of the title compound is stabilized by two intermolecular C—H···O and an intramolecular C—H···N hydrogen bonding interactions (Table 1 and Fig. 2).