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

Akkurt, M.; Karaca, S.; Jarrahpour, A.; Ebrahimi, E.; Büyükgüngör, O.

doi:10.1107/S1600536808010908

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Pages o902-o903

doi:10.1107/S1600536808010908

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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 Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 12 April 2008; accepted 18 April 2008; online 26 April 2008)

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 crystal structure 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

C₃₆H₂₅NO₃
M_r = 519.57
Monoclinic, P 2₁ /c
a = 13.7629 (9) Å
b = 10.5845 (4) Å
c = 20.5777 (12) Å
β = 114.768 (5)°
V = 2721.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 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 > 2σ(I)
R_int = 0.100

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.133
S = 1.03
5559 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808010908/lh2616sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808010908/lh2616Isup2.hkl

checkCIF report

Comment top

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: Q_T = 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).

Related literature top

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).

For related literature, see: Allen et al. (1987); Cremer & Pople (1975); Spek (2003).

Experimental top

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%.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: 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).

Figures top

	Fig. 1. The title molecular structure, with the atom-numbering scheme and 30% probability displacement ellipsoids
	Fig. 2. A view along the b axis of the packing and hydrogen bonding interactions as dashed lines. H atoms not involved in hydrogen bonding have been omitted.

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

Crystal data top

C₃₆H₂₅NO₃	F(000) = 1088
M_r = 519.57	D_x = 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

Data collection top

Stoe IPDS-2 diffractometer	3359 reflections with I > 2σ(I)
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	R_int = 0.100
Plane graphite monochromator	θ_max = 26.5°, θ_min = 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 top

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(F_o²) + (0.0486P)²] where P = (F_o² + 2F_c²)/3
5559 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₃₆H₂₅NO₃	V = 2721.9 (3) Å³
M_r = 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)°

Data collection top

Stoe IPDS-2 diffractometer	3359 reflections with I > 2σ(I)
19756 measured reflections	R_int = 0.100
5559 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.133	H-atom parameters constrained
S = 1.03	Δρ_max = 0.13 e Å⁻³
5559 reflections	Δρ_min = −0.18 e Å⁻³
361 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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···H3^viii	3.0900
O3···C8ⁱⁱ	3.317 (4)	C26···H3^viii	2.8500
O1···H17	2.7600	C26···H21^v	2.8500
O1···H18ⁱ	2.5800	C27···H21^v	2.7800
O2···H10ⁱⁱⁱ	2.8900	C28···H21^v	3.1000
O3···H8ⁱⁱ	2.4100	C29···H20^v	2.8300
O3···H28^iv	2.7300	C30···H20^v	3.0500
N1···C11	3.308 (4)	C35···H26^viii	2.9200
N1···C25	2.916 (3)	C35···H15	2.6200
N1···H11	2.8100	C36···H26^viii	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···C19^v	2.9700
C2···C27^v	3.569 (4)	H3···C20^v	3.0200
C3···C19^v	3.447 (4)	H3···C25^v	3.0900
C3···C20^v	3.471 (4)	H3···C26^v	2.8500
C3···C26^v	3.389 (4)	H5···C5^vi	2.9500
C3···C27^v	3.509 (4)	H8···O3^vii	2.4100
C5···C5^vi	3.489 (4)	H8···C22^vii	3.0700
C8···O3^vii	3.317 (4)	H10···O2^ix	2.8900
C11···N1	3.308 (4)	H10···C5^ix	2.9500
C13···C35	3.414 (4)	H10···C6^ix	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···C3^viii	3.447 (4)	H15···C35	2.6200
C20···C3^viii	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···C36^v	3.553 (3)	H20···H22A	2.2200
C26···C3^viii	3.389 (4)	H20···H22B	2.3600
C27···C3^viii	3.509 (4)	H20···C29^viii	2.8300
C27···C2^viii	3.569 (4)	H20···C30^viii	3.0500
C35···C13	3.414 (4)	H21···C15	2.7200
C36···C26^viii	3.553 (3)	H21···H15	2.3400
C36···C1	3.575 (3)	H21···C26^viii	2.8500
C5···H5^vi	2.9500	H21···C27^viii	2.7800
C5···H10ⁱⁱⁱ	2.9500	H21···C28^viii	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···C35^v	2.9200
C15···H35	2.4900	H26···C36^v	2.7500
C15···H25	2.8600	H28···H30	2.4300
C15···H11	3.0200	H28···O3^x	2.7300
C16···H25	2.5900	H30···H28	2.4300
C17···H30^iv	3.0900	H30···H32	2.4600
C17···H25	2.8800	H30···C17^x	3.0900
C18···H30^iv	2.8600	H30···C18^x	2.8600
C19···H3^viii	2.9700	H32···H30	2.4600
C20···H22A	2.7000	H35···C7	2.8100
C20···H3^viii	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.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O3^vii	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
M_r	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
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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).

References

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