1-[3-(Morpholin-4-yl)prop­yl]-4-(3-nitro­phen­yl)spiro­[azetidine-3,9′-xanthen]-2-one

Çelik, Í.; Akkurt, M.; Jarrahpour, A.; Heiran, R.; Özdemir, N.

doi:10.1107/S160053681400419X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o369-o370

doi:10.1107/S160053681400419X

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1-[3-(Morpholin-4-yl)propyl]-4-(3-nitrophenyl)spiro[azetidine-3,9′-xanthen]-2-one

Ísmail Çelik,^a Mehmet Akkurt,^b ^* Aliasghar Jarrahpour,^c Roghayeh Heiran ^c and Namık Özdemir ^d

^aDepartment of Physics, Faculty of Sciences, Cumhuriyet University, 58140 Sivas, Turkey, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and ^dDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 18 February 2014; accepted 23 February 2014; online 28 February 2014)

The β-lactam (azetidin-2-one) ring of the title compound, C₂₈H₂₇N₃O₅, is nearly planar [maximum deviation = 0.010 (1) Å] and makes dihedral angles of 75.77 (5), 52.78 (9) and 88.72 (5)°, respectively, with the benzene ring, the least-squares plane formed by the four C atoms of the morpholine ring, which adopts a chair conformation, and the xanthene ring system. In the crystal, C—H⋯O hydrogen-bond contacts connect neighbouring molecules into infinite zigzag chains running parallel to the b axis.

CCDC reference: 988430

Related literature

For general background to β-lactams, see: Arumugam et al. (2011 ); Jarrahpour et al. (2010 ); Chrysselis et al. (2000 ); Mehta et al. (2010 ); Singh (2003 ); Singh et al. (2011 , 2014 ). For similar structures, see: Akkurt et al. (2008a ,b ); Yalçın et al. (2009 ); Çelik et al. (2009a ,b ). For geometric analysis, see: Cremer & Pople (1975 ); Nardelli (1995 ).

Experimental

Crystal data

C₂₈H₂₇N₃O₅
M_r = 485.53
Monoclinic, P 2₁ /n
a = 9.2637 (6) Å
b = 11.4091 (5) Å
c = 23.3310 (15) Å
β = 96.930 (5)°
V = 2447.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.55 × 0.38 × 0.22 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.957, T_max = 0.983
19036 measured reflections
5393 independent reflections
3044 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.093
S = 0.88
5393 reflections
325 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1ⁱ	0.93	2.42	3.2423 (19)	148
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: WinGX (Farrugia, 2012).

Supporting information

CCDC reference: 988430

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681400419X/sj5392sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681400419X/sj5392Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681400419X/sj5392Isup3.cml

checkCIF report

Comment top

2-Azetidinones, commonly known as β-lactams, occupy a central place among medicinally important compounds due to their unique structure and their antibacterial activities (Arumugam et al., 2011; Jarrahpour et al., 2010; Singh, 2003; Singh et al., 2011, 2014). β-Lactams have shown many interesting biological properties, such as acting as cholesterol absorption inhibitors, and applications as antimicrobial, antifungal, antitubercular, anticancer, anti HIV and antiparkinsonian agents (Mehta et al. 2010). Moreover the morpholine moiety is present in many heterocyclic compounds with hypocholesterolemic and hypolipidemic activity (Chrysselis et al. 2000).

The β-lactam unit in (I, Fig. 1) is nearly planar, with a maximum deviation of 0.010 (1) Å from the mean plane. Atom O1 lies almost in the β-lactam plane, with a deviation of -0.001 (1) Å. The β-lactam ring makes a dihedral angle of 75.77 (5)° with the benzene ring C16—C21.

The xanthene ring system is V-shaped, with a dihedral angle between the (C4–C9) and (C10–C15) benzene rings of 27.82 (5)°. Its central ring, C2/C4/C9/O2/C10/C15, is not planar, with puckering parameters: Q_T = 0.3640 (16) Å, θ = 81.6 (3)° and φ = 181.0 (3)° (Cremer & Pople, 1975). The mean plane of the xanthene ring system forms dihedral angles of 88.72 (5), 55.87 (4) and 44.54 (7)° (Nardelli, 1995), with the β-lactam ring, the benzene ring (C16–C21) and the least-squares plane formed by the four C atoms of the morpholine ring (N3/O5/C25–C28), respectively.

The bond lengths and angles in (I) are comparable with similar compounds that we have reported previously (Akkurt et al., 2008a,b; Çelik et al., 2009a,b; Yalçın et al., 2009).

In the crystal, molecules are linked by C—H···O hydrogen contacts (Table 1) into infinite zigzag chains running parallel to [010]. Fig. 2 shows a view down the a axis of the crystal packing of (I).

Related literature top

For general background to β-lactams, see: Arumugam et al. (2011); Jarrahpour et al. (2010); Chrysselis et al. (2000); Mehta et al. (2010); Singh (2003); Singh et al. (2011, 2014). For similar structures, see: Akkurt et al. (2008a,b); Yalçın et al. (2009); Çelik et al. (2009a,b). For geometric analysis, see: Cremer & Pople (1975); Nardelli (1995).

Experimental top

A mixture of N-(3-nitrobenzylidene)-3-morpholinopropan-1-amine (1.38 g, 5.00 mmol) and triethylamine (2.53 g, 25.00 mmol), 9H-xanthen-9-carboxylic acid (1.69 g, 7.50 mmol) and tosyl chloride (1.43 g, 7.50 mmol) in CH₂Cl₂ (25 ml) was stirred at room temperature overnight. Then it was washed with HCl 1 M, saturated sodium bicarbonate solution and brine, dried with Na₂SO₄ and the solvent was evaporated to give the crude product which was purified by column chromatography (eluent 10:1 EtOAc/EtOH) as light yellow crystalline solid (Yield 59%). mp: 424–426 K. IR (KBr, cm^-1): 1751 (CO, β-lactam), 1342, 1527 (NO₂). ¹H-NMR (CDCl₃) δ (p.p.m.): 1.94 (CH₂—CH₂—CH₂–, m, 2H), 2.49 (CH₂—CH₂—CH₂– and CH₂—N morpholine ring, m, 6H), 3.18 (CH₂—CH₂—CH₂–, m, 1H), 3.68 (CH₂—O, m, 4H), 3.94 (CH₂– CH₂—CH₂–, m, 1H), 4.72 (H-4, s, 1H), 5.43 (H-3, d, J = 4.4 Hz, 1H), 6.79- 7.94 (ArH, m, 12H). ¹³C-NMR (CDCl₃) δ (p.p.m.): 24.9 (CH₂—CH₂—CH₂–), 39.9 (CH₂—CH₂—CH₂–), 53.5 (CH₂—N morpholine ring), 56.0 (CH₂—CH₂—CH₂–), 65.2 (C-4), 66.6 (CH₂—O morpholine ring), 73.4 (C-3), 116.4, 116.8, 117.1, 121.2, 121.3, 122.9, 123.0, 124.4, 125.1, 127.8, 129.3, 129.4, 129.4, 132.6, 136.9, 147.9, 151.9, 152.1 (aromatic carbons), 168.1 (CO, β-lactam). GC–MS m/z = 485 [M+]. Anal. calcd for C₂₈H₂₇N₃O₅: C 69.26, H 5.61, N 8.65%. Found: C 69.30, H 5.69, N 8.67%.

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: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

Figures top

	Fig. 1. The title molecule (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. Hydrogen bonding and molecular packing of (I) viewed along the a axis. Only H atoms involved in H bonding are shown.

1-[3-(Morpholin-4-yl)propyl]-4-(3-nitrophenyl)spiro[azetidine-3,9'-xanthen]-2-one top

Crystal data top

C₂₈H₂₇N₃O₅	F(000) = 1024
M_r = 485.53	D_x = 1.317 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 16797 reflections
a = 9.2637 (6) Å	θ = 1.8–27.6°
b = 11.4091 (5) Å	µ = 0.09 mm⁻¹
c = 23.3310 (15) Å	T = 296 K
β = 96.930 (5)°	Block, light yellow
V = 2447.9 (2) Å³	0.55 × 0.38 × 0.22 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	5393 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3044 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.041
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.2°, θ_min = 1.8°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −14→14
T_min = 0.957, T_max = 0.983	l = −29→29
19036 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.041	H-atom parameters constrained
wR(F²) = 0.093	w = 1/[σ²(F_o²) + (0.0457P)²] where P = (F_o² + 2F_c²)/3
S = 0.88	(Δ/σ)_max < 0.001
5393 reflections	Δρ_max = 0.15 e Å⁻³
325 parameters	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₈H₂₇N₃O₅	V = 2447.9 (2) Å³
M_r = 485.53	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.2637 (6) Å	µ = 0.09 mm⁻¹
b = 11.4091 (5) Å	T = 296 K
c = 23.3310 (15) Å	0.55 × 0.38 × 0.22 mm
β = 96.930 (5)°

Data collection top

Stoe IPDS 2 diffractometer	5393 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3044 reflections with I > 2σ(I)
T_min = 0.957, T_max = 0.983	R_int = 0.041
19036 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 0.88	Δρ_max = 0.15 e Å⁻³
5393 reflections	Δρ_min = −0.21 e Å⁻³
325 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 F² 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 F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² 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	0.84675 (13)	0.41791 (9)	0.23520 (5)	0.0578 (4)
O2	0.49859 (13)	0.68567 (11)	0.32597 (5)	0.0642 (5)
O3	0.21884 (16)	0.55524 (13)	0.00379 (6)	0.0903 (6)
O4	0.39138 (19)	0.44168 (14)	0.03770 (8)	0.1073 (7)
O5	0.76395 (16)	0.93149 (14)	−0.03119 (7)	0.0914 (6)
N1	0.80288 (13)	0.58505 (10)	0.17769 (5)	0.0425 (4)
N2	0.33075 (18)	0.53649 (15)	0.03527 (6)	0.0641 (6)
N3	0.86873 (15)	0.81179 (12)	0.07346 (6)	0.0539 (5)
C1	0.78855 (17)	0.51133 (13)	0.22163 (6)	0.0424 (5)
C2	0.67968 (16)	0.59013 (12)	0.24776 (6)	0.0406 (5)
C3	0.69833 (16)	0.67310 (12)	0.19331 (6)	0.0405 (4)
C4	0.74121 (18)	0.64401 (13)	0.30441 (6)	0.0447 (5)
C5	0.88946 (19)	0.65055 (15)	0.32229 (7)	0.0566 (6)
C6	0.9422 (2)	0.70557 (18)	0.37322 (8)	0.0727 (7)
C7	0.8472 (3)	0.75553 (18)	0.40659 (8)	0.0746 (8)
C8	0.6998 (2)	0.74905 (16)	0.39060 (7)	0.0667 (7)
C9	0.64771 (19)	0.69209 (14)	0.33962 (7)	0.0512 (5)
C10	0.44594 (19)	0.59521 (15)	0.28968 (7)	0.0533 (6)
C11	0.3044 (2)	0.55984 (18)	0.29314 (9)	0.0704 (8)
C12	0.2471 (2)	0.4687 (2)	0.25963 (10)	0.0783 (8)
C13	0.3315 (2)	0.41067 (18)	0.22397 (9)	0.0729 (8)
C14	0.4725 (2)	0.44662 (15)	0.22061 (7)	0.0588 (6)
C15	0.53121 (18)	0.54190 (14)	0.25249 (6)	0.0465 (5)
C16	0.57100 (16)	0.69479 (13)	0.14871 (6)	0.0405 (4)
C17	0.50680 (17)	0.80495 (14)	0.14408 (6)	0.0484 (5)
C18	0.39007 (18)	0.82805 (15)	0.10310 (7)	0.0557 (6)
C19	0.33281 (18)	0.74088 (16)	0.06655 (7)	0.0535 (6)
C20	0.39514 (17)	0.63143 (14)	0.07194 (6)	0.0462 (5)
C21	0.51418 (17)	0.60747 (13)	0.11139 (6)	0.0454 (5)
C22	0.89002 (19)	0.57752 (15)	0.13018 (7)	0.0534 (6)
C23	1.0149 (2)	0.66323 (17)	0.13299 (8)	0.0672 (7)
C24	0.9716 (2)	0.79100 (17)	0.12441 (8)	0.0637 (7)
C25	0.8098 (3)	0.93061 (16)	0.07274 (10)	0.0799 (8)
C26	0.7015 (3)	0.9490 (2)	0.02030 (12)	0.0950 (10)
C27	0.8214 (2)	0.8171 (2)	−0.03121 (9)	0.0820 (8)
C28	0.9321 (2)	0.79517 (17)	0.02015 (7)	0.0643 (7)
H3	0.74730	0.74660	0.20560	0.0490*
H5	0.95440	0.61730	0.29950	0.0680*
H6	1.04170	0.70870	0.38480	0.0870*
H7	0.88280	0.79430	0.44040	0.0900*
H8	0.63560	0.78240	0.41360	0.0800*
H11	0.24860	0.59770	0.31810	0.0850*
H12	0.15120	0.44600	0.26090	0.0940*
H13	0.29340	0.34720	0.20210	0.0870*
H14	0.52900	0.40660	0.19670	0.0710*
H17	0.54320	0.86430	0.16910	0.0580*
H18	0.35000	0.90290	0.10020	0.0670*
H19	0.25390	0.75550	0.03890	0.0640*
H21	0.55610	0.53330	0.11300	0.0550*
H22A	0.82710	0.59030	0.09440	0.0640*
H22B	0.92870	0.49870	0.12900	0.0640*
H23A	1.07620	0.64180	0.10370	0.0810*
H23B	1.07290	0.65530	0.17030	0.0810*
H24A	0.92910	0.81780	0.15810	0.0760*
H24B	1.05830	0.83720	0.12160	0.0760*
H25A	0.88840	0.98680	0.07270	0.0960*
H25B	0.76320	0.94350	0.10730	0.0960*
H26A	0.62100	0.89510	0.02140	0.1140*
H26B	0.66330	1.02810	0.02080	0.1140*
H27A	0.86620	0.80520	−0.06630	0.0980*
H27B	0.74280	0.76090	−0.03110	0.0980*
H28A	0.96870	0.71570	0.01860	0.0770*
H28B	1.01330	0.84850	0.01920	0.0770*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0719 (8)	0.0442 (6)	0.0557 (6)	0.0105 (6)	0.0012 (6)	0.0086 (5)
O2	0.0646 (8)	0.0644 (8)	0.0658 (8)	−0.0010 (7)	0.0172 (6)	−0.0135 (6)
O3	0.0830 (10)	0.1006 (11)	0.0769 (9)	−0.0037 (8)	−0.0333 (8)	−0.0132 (8)
O4	0.1157 (13)	0.0641 (10)	0.1279 (13)	0.0029 (9)	−0.0430 (11)	−0.0246 (9)
O5	0.0794 (10)	0.0904 (11)	0.1034 (12)	0.0183 (9)	0.0075 (9)	0.0388 (9)
N1	0.0466 (7)	0.0417 (7)	0.0391 (6)	0.0052 (6)	0.0044 (6)	0.0046 (6)
N2	0.0675 (10)	0.0654 (10)	0.0551 (9)	−0.0072 (8)	−0.0104 (8)	−0.0034 (8)
N3	0.0539 (8)	0.0478 (8)	0.0602 (8)	0.0011 (7)	0.0082 (7)	0.0008 (7)
C1	0.0474 (9)	0.0388 (8)	0.0382 (8)	−0.0011 (7)	−0.0061 (7)	0.0026 (7)
C2	0.0480 (9)	0.0383 (8)	0.0347 (7)	−0.0009 (7)	0.0023 (6)	0.0033 (6)
C3	0.0447 (8)	0.0374 (8)	0.0386 (7)	−0.0003 (7)	0.0022 (6)	0.0009 (6)
C4	0.0565 (10)	0.0429 (8)	0.0339 (7)	−0.0037 (8)	0.0020 (7)	0.0043 (6)
C5	0.0568 (11)	0.0641 (11)	0.0469 (9)	−0.0088 (9)	−0.0017 (8)	0.0006 (8)
C6	0.0737 (13)	0.0866 (14)	0.0534 (10)	−0.0198 (12)	−0.0102 (10)	−0.0017 (10)
C7	0.0998 (17)	0.0782 (14)	0.0435 (10)	−0.0289 (12)	−0.0012 (11)	−0.0078 (9)
C8	0.0974 (16)	0.0619 (11)	0.0433 (9)	−0.0142 (11)	0.0190 (10)	−0.0082 (8)
C9	0.0609 (11)	0.0491 (9)	0.0438 (8)	−0.0065 (8)	0.0076 (8)	0.0029 (8)
C10	0.0532 (10)	0.0551 (10)	0.0514 (9)	−0.0036 (9)	0.0054 (8)	0.0052 (8)
C11	0.0551 (12)	0.0800 (14)	0.0777 (13)	−0.0019 (10)	0.0146 (10)	0.0084 (11)
C12	0.0570 (12)	0.0886 (15)	0.0886 (15)	−0.0207 (12)	0.0055 (11)	0.0157 (13)
C13	0.0721 (14)	0.0705 (13)	0.0738 (13)	−0.0266 (11)	0.0000 (11)	0.0004 (11)
C14	0.0647 (12)	0.0560 (10)	0.0551 (10)	−0.0142 (9)	0.0045 (9)	−0.0001 (8)
C15	0.0517 (10)	0.0458 (9)	0.0407 (8)	−0.0045 (8)	0.0009 (7)	0.0075 (7)
C16	0.0445 (8)	0.0419 (8)	0.0353 (7)	0.0014 (7)	0.0053 (6)	0.0033 (7)
C17	0.0565 (10)	0.0451 (9)	0.0433 (8)	0.0069 (8)	0.0045 (8)	−0.0021 (7)
C18	0.0584 (11)	0.0520 (10)	0.0556 (10)	0.0184 (8)	0.0020 (8)	0.0012 (8)
C19	0.0456 (9)	0.0694 (11)	0.0444 (9)	0.0093 (9)	0.0005 (8)	0.0059 (8)
C20	0.0476 (9)	0.0521 (9)	0.0385 (8)	−0.0022 (8)	0.0031 (7)	0.0006 (7)
C21	0.0517 (9)	0.0416 (9)	0.0420 (8)	0.0032 (7)	0.0015 (7)	0.0038 (7)
C22	0.0622 (11)	0.0526 (10)	0.0472 (9)	0.0087 (9)	0.0145 (8)	0.0023 (8)
C23	0.0517 (10)	0.0897 (15)	0.0603 (11)	0.0010 (10)	0.0072 (9)	0.0204 (10)
C24	0.0626 (12)	0.0716 (12)	0.0571 (10)	−0.0203 (10)	0.0085 (9)	0.0010 (9)
C25	0.0907 (15)	0.0502 (11)	0.1043 (16)	0.0055 (11)	0.0337 (14)	−0.0014 (11)
C26	0.0768 (15)	0.0736 (15)	0.136 (2)	0.0262 (12)	0.0188 (16)	0.0281 (15)
C27	0.0839 (15)	0.0882 (16)	0.0705 (13)	0.0121 (12)	−0.0048 (11)	0.0079 (12)
C28	0.0641 (12)	0.0697 (12)	0.0586 (10)	0.0146 (10)	0.0059 (9)	0.0062 (9)

Geometric parameters (Å, º) top

O1—C1	1.2189 (18)	C18—C19	1.374 (2)
O2—C9	1.382 (2)	C19—C20	1.375 (2)
O2—C10	1.386 (2)	C20—C21	1.376 (2)
O3—N2	1.215 (2)	C22—C23	1.510 (3)
O4—N2	1.217 (2)	C23—C24	1.519 (3)
O5—C26	1.409 (3)	C25—C26	1.500 (4)
O5—C27	1.410 (3)	C27—C28	1.501 (3)
N1—C1	1.3449 (18)	C3—H3	0.9800
N1—C3	1.4715 (19)	C5—H5	0.9300
N1—C22	1.450 (2)	C6—H6	0.9300
N2—C20	1.462 (2)	C7—H7	0.9300
N3—C24	1.451 (2)	C8—H8	0.9300
N3—C25	1.461 (2)	C11—H11	0.9300
N3—C28	1.450 (2)	C12—H12	0.9300
C1—C2	1.532 (2)	C13—H13	0.9300
C2—C3	1.610 (2)	C14—H14	0.9300
C2—C4	1.506 (2)	C17—H17	0.9300
C2—C15	1.498 (2)	C18—H18	0.9300
C3—C16	1.496 (2)	C19—H19	0.9300
C4—C5	1.388 (2)	C21—H21	0.9300
C4—C9	1.378 (2)	C22—H22A	0.9700
C5—C6	1.380 (3)	C22—H22B	0.9700
C6—C7	1.368 (3)	C23—H23A	0.9700
C7—C8	1.373 (3)	C23—H23B	0.9700
C8—C9	1.390 (2)	C24—H24A	0.9700
C10—C11	1.384 (3)	C24—H24B	0.9700
C10—C15	1.383 (2)	C25—H25A	0.9700
C11—C12	1.369 (3)	C25—H25B	0.9700
C12—C13	1.378 (3)	C26—H26A	0.9700
C13—C14	1.380 (3)	C26—H26B	0.9700
C14—C15	1.390 (2)	C27—H27A	0.9700
C16—C17	1.389 (2)	C27—H27B	0.9700
C16—C21	1.385 (2)	C28—H28A	0.9700
C17—C18	1.380 (2)	C28—H28B	0.9700

C9—O2—C10	116.66 (13)	C2—C3—H3	111.00
C26—O5—C27	108.99 (17)	C16—C3—H3	111.00
C1—N1—C3	96.30 (11)	C4—C5—H5	119.00
C1—N1—C22	131.36 (13)	C6—C5—H5	119.00
C3—N1—C22	132.33 (12)	C5—C6—H6	120.00
O3—N2—O4	122.68 (17)	C7—C6—H6	120.00
O3—N2—C20	118.78 (16)	C6—C7—H7	120.00
O4—N2—C20	118.54 (16)	C8—C7—H7	120.00
C24—N3—C25	111.64 (15)	C7—C8—H8	120.00
C24—N3—C28	112.80 (14)	C9—C8—H8	120.00
C25—N3—C28	107.51 (15)	C10—C11—H11	120.00
O1—C1—N1	131.57 (14)	C12—C11—H11	120.00
O1—C1—C2	134.57 (14)	C11—C12—H12	120.00
N1—C1—C2	93.82 (11)	C13—C12—H12	120.00
C1—C2—C3	83.83 (10)	C12—C13—H13	120.00
C1—C2—C4	113.04 (12)	C14—C13—H13	120.00
C1—C2—C15	117.93 (12)	C13—C14—H14	120.00
C3—C2—C4	112.78 (11)	C15—C14—H14	120.00
C3—C2—C15	117.45 (12)	C16—C17—H17	119.00
C4—C2—C15	109.82 (12)	C18—C17—H17	119.00
N1—C3—C2	86.02 (10)	C17—C18—H18	120.00
N1—C3—C16	115.33 (12)	C19—C18—H18	120.00
C2—C3—C16	119.69 (12)	C18—C19—H19	121.00
C2—C4—C5	122.79 (14)	C20—C19—H19	121.00
C2—C4—C9	119.16 (15)	C16—C21—H21	120.00
C5—C4—C9	118.02 (14)	C20—C21—H21	120.00
C4—C5—C6	121.18 (16)	N1—C22—H22A	108.00
C5—C6—C7	119.63 (18)	N1—C22—H22B	109.00
C6—C7—C8	120.65 (18)	C23—C22—H22A	109.00
C7—C8—C9	119.26 (17)	C23—C22—H22B	109.00
O2—C9—C4	121.64 (14)	H22A—C22—H22B	108.00
O2—C9—C8	117.15 (15)	C22—C23—H23A	108.00
C4—C9—C8	121.21 (16)	C22—C23—H23B	108.00
O2—C10—C11	116.60 (16)	C24—C23—H23A	108.00
O2—C10—C15	121.69 (15)	C24—C23—H23B	108.00
C11—C10—C15	121.70 (16)	H23A—C23—H23B	107.00
C10—C11—C12	119.55 (18)	N3—C24—H24A	109.00
C11—C12—C13	120.04 (18)	N3—C24—H24B	109.00
C12—C13—C14	120.09 (18)	C23—C24—H24A	109.00
C13—C14—C15	120.91 (17)	C23—C24—H24B	109.00
C2—C15—C10	118.93 (14)	H24A—C24—H24B	108.00
C2—C15—C14	123.45 (14)	N3—C25—H25A	109.00
C10—C15—C14	117.61 (16)	N3—C25—H25B	110.00
C3—C16—C17	119.86 (13)	C26—C25—H25A	110.00
C3—C16—C21	121.75 (13)	C26—C25—H25B	110.00
C17—C16—C21	118.39 (13)	H25A—C25—H25B	108.00
C16—C17—C18	121.28 (14)	O5—C26—H26A	109.00
C17—C18—C19	120.22 (16)	O5—C26—H26B	109.00
C18—C19—C20	118.30 (15)	C25—C26—H26A	109.00
N2—C20—C19	118.82 (14)	C25—C26—H26B	109.00
N2—C20—C21	118.80 (14)	H26A—C26—H26B	108.00
C19—C20—C21	122.37 (14)	O5—C27—H27A	109.00
C16—C21—C20	119.40 (14)	O5—C27—H27B	109.00
N1—C22—C23	115.00 (14)	C28—C27—H27A	109.00
C22—C23—C24	115.28 (15)	C28—C27—H27B	109.00
N3—C24—C23	113.70 (15)	H27A—C27—H27B	108.00
N3—C25—C26	110.57 (17)	N3—C28—H28A	109.00
O5—C26—C25	111.9 (2)	N3—C28—H28B	109.00
O5—C27—C28	112.07 (17)	C27—C28—H28A	110.00
N3—C28—C27	110.76 (15)	C27—C28—H28B	110.00
N1—C3—H3	111.00	H28A—C28—H28B	108.00

C9—O2—C10—C11	155.89 (16)	C1—C2—C15—C14	−19.2 (2)
C10—O2—C9—C4	23.8 (2)	C15—C2—C3—N1	−119.59 (13)
C10—O2—C9—C8	−156.04 (15)	C1—C2—C15—C10	161.87 (14)
C9—O2—C10—C15	−23.2 (2)	C3—C2—C15—C14	78.76 (19)
C27—O5—C26—C25	57.9 (2)	C1—C2—C4—C9	−163.90 (14)
C26—O5—C27—C28	−57.7 (2)	C2—C3—C16—C17	110.27 (15)
C1—N1—C22—C23	−110.50 (18)	C2—C3—C16—C21	−69.70 (18)
C3—N1—C1—O1	−179.56 (17)	N1—C3—C16—C21	30.8 (2)
C22—N1—C1—C2	179.91 (15)	N1—C3—C16—C17	−149.28 (13)
C22—N1—C1—O1	1.9 (3)	C5—C4—C9—O2	−177.71 (14)
C3—N1—C1—C2	−1.50 (12)	C9—C4—C5—C6	−1.3 (2)
C3—N1—C22—C23	71.4 (2)	C2—C4—C5—C6	176.86 (16)
C1—N1—C3—C16	−119.66 (13)	C2—C4—C9—O2	4.1 (2)
C22—N1—C3—C2	180.00 (15)	C5—C4—C9—C8	2.2 (2)
C22—N1—C3—C16	58.9 (2)	C2—C4—C9—C8	−176.06 (15)
C1—N1—C3—C2	1.43 (11)	C4—C5—C6—C7	−0.6 (3)
O3—N2—C20—C21	174.10 (15)	C5—C6—C7—C8	1.6 (3)
O4—N2—C20—C19	175.60 (17)	C6—C7—C8—C9	−0.7 (3)
O4—N2—C20—C21	−5.7 (2)	C7—C8—C9—O2	178.67 (16)
O3—N2—C20—C19	−4.6 (2)	C7—C8—C9—C4	−1.2 (3)
C24—N3—C25—C26	−178.81 (18)	C11—C10—C15—C14	−3.4 (2)
C28—N3—C24—C23	−69.47 (19)	O2—C10—C15—C2	−5.3 (2)
C25—N3—C24—C23	169.34 (17)	C11—C10—C15—C2	175.60 (16)
C28—N3—C25—C26	57.0 (2)	C15—C10—C11—C12	0.9 (3)
C25—N3—C28—C27	−56.8 (2)	O2—C10—C11—C12	−178.17 (18)
C24—N3—C28—C27	179.73 (16)	O2—C10—C15—C14	175.66 (15)
O1—C1—C2—C15	−62.8 (2)	C10—C11—C12—C13	1.8 (3)
O1—C1—C2—C3	179.33 (19)	C11—C12—C13—C14	−2.0 (3)
O1—C1—C2—C4	67.2 (2)	C12—C13—C14—C15	−0.6 (3)
N1—C1—C2—C15	119.25 (13)	C13—C14—C15—C10	3.2 (2)
N1—C1—C2—C4	−110.79 (13)	C13—C14—C15—C2	−175.76 (16)
N1—C1—C2—C3	1.37 (11)	C21—C16—C17—C18	−0.6 (2)
C1—C2—C4—C5	18.0 (2)	C3—C16—C17—C18	179.44 (14)
C15—C2—C3—C16	−2.59 (19)	C3—C16—C21—C20	178.70 (14)
C4—C2—C15—C14	−150.62 (15)	C17—C16—C21—C20	−1.3 (2)
C15—C2—C4—C9	−29.94 (19)	C16—C17—C18—C19	1.4 (2)
C3—C2—C4—C9	103.12 (16)	C17—C18—C19—C20	−0.2 (2)
C15—C2—C4—C5	151.94 (15)	C18—C19—C20—C21	−1.7 (2)
C4—C2—C3—C16	−131.83 (14)	C18—C19—C20—N2	176.99 (15)
C3—C2—C15—C10	−100.18 (16)	C19—C20—C21—C16	2.5 (2)
C4—C2—C3—N1	111.17 (13)	N2—C20—C21—C16	−176.22 (14)
C1—C2—C3—C16	115.75 (13)	N1—C22—C23—C24	−68.6 (2)
C1—C2—C3—N1	−1.25 (10)	C22—C23—C24—N3	−50.6 (2)
C4—C2—C15—C10	30.44 (19)	N3—C25—C26—O5	−59.3 (2)
C3—C2—C4—C5	−75.00 (18)	O5—C27—C28—N3	59.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1ⁱ	0.93	2.42	3.2423 (19)	148
C22—H22A···N3	0.97	2.61	2.978 (2)	103

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1ⁱ	0.93	2.42	3.2423 (19)	148

Symmetry code: (i) −x+3/2, y+1/2, −z+1/2.

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).

References

Akkurt, M., Jarrahpour, A., Ebrahimi, E., Gençaslan, M. & Büyükgüngör, O. (2008a). Acta Cryst. E64, o2466–o2467. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Akkurt, M., Karaca, S., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2008b). Acta Cryst. E64, o902–o903. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Arumugam, N., Periyasami, G., Raghunathan, R., Kamalraj, S. & Muthumary, J. (2011). Eur. J. Med. Chem. 46, 600–607. Web of Science CrossRef CAS PubMed Google Scholar
Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009a). Acta Cryst. E65, o501–o502. Web of Science CSD CrossRef IUCr Journals Google Scholar
Çelik, Í., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009b). Acta Cryst. E65, o2522–o2523. Web of Science CSD CrossRef IUCr Journals Google Scholar
Chrysselis, M. C., Rekka, E. A. & Kourounakis, P. N. (2000). J. Med. Chem. 43, 609–612. Web of Science CrossRef PubMed CAS Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jarrahpour, A., Eskandari, M., Zomorodian, K., Barati, E., Ashori, R., Salehi Vaziri, M. & Pakshir, K. (2010). Anti-Infective Agents Med. Chem. 9, 205–219. CrossRef CAS Google Scholar
Mehta, P. D., Sengar, N. P. S. & Pathak, A. K. (2010). Eur. J. Med. Chem. 45, 5541–5560. Web of Science CrossRef CAS PubMed Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, G. S. (2003). Tetrahedron, 59, 7631–7649. Web of Science CrossRef CAS Google Scholar
Singh, G. S., D'hooghe, M. & De Kimpe, N. (2011). Tetrahedron, 67, 1989–2012. Web of Science CrossRef CAS Google Scholar
Singh, P., Raj, R., Singh, P., Gut, J., Rosenthal, P. J. & Kumar, V. (2014). Eur. J. Med. Chem. 71, 128–134. Web of Science CrossRef CAS PubMed Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar
Yalçın, Ş. P., Akkurt, M., Jarrahpour, A., Ebrahimi, E. & Büyükgüngör, O. (2009). Acta Cryst. E65, o626–o627. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 70| Part 3| March 2014| Pages o369-o370

doi:10.1107/S160053681400419X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-[3-(Morpholin-4-yl)prop­yl]-4-(3-nitro­phen­yl)spiro­[azetidine-3,9′-xanthen]-2-one

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organic compounds

1-[3-(Morpholin-4-yl)propyl]-4-(3-nitrophenyl)spiro[azetidine-3,9′-xanthen]-2-one