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

Atioğlu, Z.; Akkurt, M.; Jarrahpour, A.; Heiran, R.; Özdemir, N.

doi:10.1107/S1600536814013464

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 7| July 2014| Pages o772-o773

https://doi.org/10.1107/S1600536814013464

Open

access

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

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

^aIlke Education and Health Foundation, Cappadocia Vocational College, The Medical Imaging Techniques Program, 50420 Mustafapaşa, Ürgüp, Nevşehir, 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 9 June 2014; accepted 10 June 2014; online 14 June 2014)

In the title compound, C₂₂H₂₁N₃O₅, the β-lactam (azetidin-2-one) ring is nearly planar [maximum deviation = 0.010 (1) Å] and makes dihedral angles of 69.22 (5), 55.32 (5) and 89.42 (4)° with the least-squares planes formed by the four C atoms of the morpholine ring, which adopts a chair conformation, the benzene ring and the xanthene ring system, respectively. In the crystal, C—H⋯O hydrogen-bond contacts connect neighbouring molecules into infinite zigzag chains running parallel to the b axis.

CCDC reference: 1007508

Related literature

For general background to β-lactams, see: Arya et al. (2014 ); Ebrahimi & Jarrahpour (2014 ); Singh & Sudheesh (2014 ); Zeng et al. (2014 ); Zarei et al. (2013 ); Jarrahpour & Ebrahimi (2010 ); Mehta et al. (2010 ); Singh et al. (2011 ). For geometric analysis, see: Cremer & Pople (1975 ); Nardelli (1995 ). For similar structures, see: Akkurt et al. (2008a ,b ); Yalçın et al. (2009 ); Çelik et al. (2009a ,b , 2014 ).

Experimental

Crystal data

C₂₅H₂₁N₃O₅
M_r = 443.45
Monoclinic, P 2₁ /c
a = 9.4272 (5) Å
b = 18.8525 (8) Å
c = 12.4345 (6) Å
β = 95.443 (4)°
V = 2199.97 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.50 × 0.44 × 0.40 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.956, T_max = 0.974
13801 measured reflections
5223 independent reflections
3421 reflections with I > 2σ(I)
R_int = 0.195

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.098
S = 1.00
5223 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.11 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O3ⁱ	0.98	2.55	3.5310 (16)	174
C6—H6⋯O1ⁱⁱ	0.93	2.56	3.3828 (17)	148
C11—H11⋯O2ⁱⁱⁱ	0.93	2.50	3.389 (2)	159
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+2, -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: 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: 1007508

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536814013464/sj5411sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536814013464/sj5411Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536814013464/sj5411Isup3.cml

checkCIF report

Comment top

2-Azetidinones, commonly known as β-lactams, constitute a most important class of antibiotics in both human and veterinary medicine (Arya et al., 2014; Singh & Sudheesh, 2014; Zeng et al., 2014; Zarei et al., 2013). In addition to their well recognized antibiotic activity, β-lactams exhibit various other biological activities such as thrombin, human, HIV-1 protease, human leukocyte elastase, cholesterol absorption inhibition and antifungal, anticancer, antidiabetic and potential antimalarial properties (Mehta et al., 2010; Singh et al., 2011; Ebrahimi & Jarrahpour, 2014). The synthesis and chemistry of spiro-fused 2-azetidinones has grown steadily over the years and many newly synthesized spiro-fused 2-azetidinones have been reported in the literature (Jarrahpour & Ebrahimi, 2010; Singh et al., 2011).

The β-lactam (azetidin-2-one) ring of the title compound (I, Fig. 1) is nearly planar, with a maximum deviation of -0.010 (1) Å for C1 from the mean plane. Atom O1 lies almost in the β-lactam plane, with a deviation of 0.069 (1) Å. The β-lactam ring makes a dihedral angle of 55.32 (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 19.07 (7)°. Its central ring, C2/C4/C9/O2/C10/C15, is not planar, with puckering parameters: Q_T = 0.2438 (13) Å, θ = 98.1 (3)° and φ = 2.0 (3)° (Cremer & Pople, 1975).

The mean plane of the xanthene ring system forms dihedral angles of 89.42 (4), 43.44 (3) and 22.80 (5)° (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 (N2/O5/C22–C25), respectively.

The bond lengths and angles in (I) are comparable with those observed in similar compounds that we have reported previously (Akkurt et al., 2008a,b; Çelik et al., 2009a,b; Çelik et al., 2014; Yalçın et al., 2009).

In the crystal structure, molecules are linked by C—H···O hydrogen contacts (Table 1) into infinite zigzag chains running parallel to the b axis. Figs. 2, 3 and 4 show the projections along the a, b and c axes of the crystal packing of (I), respectively.

Related literature top

For general background to β-lactams, see: Arya et al. (2014); Ebrahimi & Jarrahpour (2014); Singh & Sudheesh (2014); Zeng et al. (2014); Zarei et al. (2013); Jarrahpour & Ebrahimi (2010); Mehta et al. (2010); Singh et al. (2011). For geometric analysis, see: Cremer & Pople (1975); Nardelli (1995). For similar structures, see: Akkurt et al. (2008a,b); Yalçın et al. (2009); Çelik et al. (2009a,b, 2014).

Experimental top

A mixture of N-(2-nitrobenzylidene)morpholin-4-amine (0.24 g, 1.00 mmol), 9H-xanthen-9-carboxylic acid (0.34 g, 1.50 mmol), tosyl chloride (0.28 g, 1.50 mmol) and triethylamine (0.25 g, 2.50 mmol) was stirred in dry CH₂Cl₂ at room temperature. After 24 h, the mixture was washed with HCl 1 M (20 ml), saturated NaHCO₃ (20 ml), brine (20 ml), dried over Na₂SO₄ and the solvent was evaporated to give the crude product which was purified by column chromatography (eluent 2:1 n-hexane/EtOAc) as light yellow crystalline solid (yield 41%). mp: 471- 473 K. IR (KBr, cm^-1): 1759 (CO, β-lactam), 1346, 1523 (NO2). ¹H-NMR (CDCl3) δ (p.p.m.): 3.52–3.76 (CH₂ morpholine ring, m, 8H), 5.38 (H-3, s, 1H), 6.62–8.10 (ArH, m, 12H). ¹³C-NMR (CDCl₃) δ (p.p.m.): 53.8 (CH₂—N), 61.4 (C-3), 66.8 (CH₂—O), 73.9 (C-4), 114.9, 116.8, 116.9, 120.5, 122.2, 123.9, 124.8, 125.1, 127.8, 128.9, 129.3, 129.5, 131.1, 133.1, 147.5, 152.1, 152.3 (aromatic carbons), 169.7 (CO, β-lactam). Anal. calcd for C₂₅H₂₁N₃O₅: C 67.71, H 4.77, N 9.48%. Found: C 67.80, H 4.66, N 9.45%.

Structure description top

For general background to β-lactams, see: Arya et al. (2014); Ebrahimi & Jarrahpour (2014); Singh & Sudheesh (2014); Zeng et al. (2014); Zarei et al. (2013); Jarrahpour & Ebrahimi (2010); Mehta et al. (2010); Singh et al. (2011). For geometric analysis, see: Cremer & Pople (1975); Nardelli (1995). For similar structures, see: Akkurt et al. (2008a,b); Yalçın et al. (2009); Çelik et al. (2009a,b, 2014).

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 molecular structure of (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.
	Fig. 3. Hydrogen bonding and molecular packing of (I) viewed along the b axis. Only H atoms involved in H bonding are shown.
	Fig. 4. Hydrogen bonding and molecular packing of (I) viewed along the c axis. Only H atoms involved in H bonding are shown.

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

Crystal data top

C₂₅H₂₁N₃O₅	F(000) = 928
M_r = 443.45	D_x = 1.339 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 14473 reflections
a = 9.4272 (5) Å	θ = 1.6–28.4°
b = 18.8525 (8) Å	µ = 0.10 mm⁻¹
c = 12.4345 (6) Å	T = 296 K
β = 95.443 (4)°	Block, light yellow
V = 2199.97 (18) Å³	0.50 × 0.44 × 0.40 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	5223 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3421 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.195
Detector resolution: 6.67 pixels mm^-1	θ_max = 27.9°, θ_min = 2.0°
ω scans	h = −12→8
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −24→24
T_min = 0.956, T_max = 0.974	l = −16→16
13801 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.098	w = 1/[σ²(F_o²) + (0.0511P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
5223 reflections	Δρ_max = 0.15 e Å⁻³
299 parameters	Δρ_min = −0.11 e Å⁻³

Crystal data top

C₂₅H₂₁N₃O₅	V = 2199.97 (18) Å³
M_r = 443.45	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4272 (5) Å	µ = 0.10 mm⁻¹
b = 18.8525 (8) Å	T = 296 K
c = 12.4345 (6) Å	0.50 × 0.44 × 0.40 mm
β = 95.443 (4)°

Data collection top

Stoe IPDS 2 diffractometer	5223 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	3421 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.974	R_int = 0.195
13801 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.098	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
5223 reflections	Δρ_min = −0.11 e Å⁻³
299 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	0.56523 (11)	0.77674 (4)	0.39775 (8)	0.0607 (3)
O2	0.88039 (12)	0.56659 (6)	0.40826 (8)	0.0725 (4)
O3	0.59829 (13)	0.48451 (5)	0.40169 (9)	0.0738 (4)
O4	0.6611 (2)	0.42173 (8)	0.27221 (13)	0.1293 (7)
O5	0.05898 (13)	0.80037 (7)	0.43054 (10)	0.0862 (5)
N1	0.40654 (11)	0.68165 (5)	0.36241 (8)	0.0475 (3)
N2	0.26494 (11)	0.70325 (5)	0.37024 (8)	0.0504 (3)
N3	0.58819 (15)	0.46781 (6)	0.30725 (11)	0.0673 (5)
C1	0.53326 (14)	0.71537 (6)	0.38183 (9)	0.0459 (4)
C2	0.61723 (13)	0.64499 (6)	0.38092 (9)	0.0439 (4)
C3	0.46359 (13)	0.60880 (6)	0.36101 (9)	0.0444 (4)
C4	0.71522 (13)	0.63736 (6)	0.29281 (9)	0.0450 (4)
C5	0.68634 (14)	0.66829 (7)	0.19146 (10)	0.0527 (4)
C6	0.77624 (16)	0.65986 (8)	0.11144 (11)	0.0610 (5)
C7	0.89724 (16)	0.61957 (8)	0.13129 (12)	0.0648 (5)
C8	0.92974 (16)	0.58875 (8)	0.23033 (12)	0.0665 (5)
C9	0.83854 (14)	0.59821 (7)	0.31040 (10)	0.0536 (4)
C10	0.81733 (15)	0.58925 (7)	0.49807 (10)	0.0554 (4)
C11	0.88545 (17)	0.56948 (9)	0.59700 (12)	0.0697 (6)
C12	0.83068 (17)	0.59109 (8)	0.68992 (12)	0.0668 (5)
C13	0.71169 (18)	0.63341 (7)	0.68493 (11)	0.0631 (5)
C14	0.64380 (16)	0.65115 (7)	0.58589 (10)	0.0555 (4)
C15	0.69405 (14)	0.62872 (6)	0.48998 (10)	0.0465 (4)
C16	0.42467 (13)	0.56881 (6)	0.25733 (10)	0.0477 (4)
C17	0.48294 (15)	0.50353 (6)	0.23145 (10)	0.0536 (4)
C18	0.44357 (19)	0.46854 (8)	0.13552 (12)	0.0691 (6)
C19	0.34418 (19)	0.49821 (9)	0.06166 (12)	0.0749 (6)
C20	0.28575 (18)	0.56245 (10)	0.08314 (12)	0.0736 (6)
C21	0.32615 (15)	0.59701 (8)	0.17932 (11)	0.0605 (5)
C22	0.23610 (17)	0.71132 (8)	0.48318 (11)	0.0640 (5)
C23	0.08391 (19)	0.73546 (10)	0.48559 (15)	0.0822 (7)
C24	0.0851 (2)	0.79149 (11)	0.32138 (15)	0.0905 (7)
C25	0.23701 (19)	0.77036 (8)	0.31261 (12)	0.0712 (6)
H3	0.44030	0.58160	0.42410	0.0530*
H5	0.60420	0.69530	0.17750	0.0630*
H6	0.75520	0.68130	0.04450	0.0730*
H7	0.95760	0.61320	0.07710	0.0780*
H8	1.01210	0.56180	0.24380	0.0800*
H11	0.96750	0.54180	0.60040	0.0840*
H12	0.87440	0.57700	0.75670	0.0800*
H13	0.67740	0.64990	0.74800	0.0760*
H14	0.56200	0.67890	0.58290	0.0670*
H18	0.48450	0.42510	0.12130	0.0830*
H19	0.31650	0.47480	−0.00280	0.0900*
H20	0.21860	0.58300	0.03290	0.0880*
H21	0.28560	0.64080	0.19200	0.0730*
H22A	0.30050	0.74600	0.51880	0.0770*
H22B	0.25040	0.66650	0.52080	0.0770*
H23A	0.02040	0.69950	0.45230	0.0990*
H23B	0.06300	0.74100	0.56000	0.0990*
H24A	0.06510	0.83550	0.28260	0.1090*
H24B	0.02210	0.75530	0.28850	0.1090*
H25A	0.25350	0.76480	0.23730	0.0850*
H25B	0.30070	0.80690	0.34390	0.0850*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0664 (6)	0.0398 (4)	0.0748 (6)	−0.0032 (4)	0.0010 (5)	−0.0022 (4)
O2	0.0706 (7)	0.0878 (7)	0.0609 (6)	0.0346 (6)	0.0163 (5)	0.0220 (5)
O3	0.0973 (9)	0.0551 (6)	0.0684 (6)	0.0094 (5)	0.0043 (6)	0.0026 (5)
O4	0.1586 (16)	0.1034 (10)	0.1227 (11)	0.0737 (10)	−0.0035 (10)	−0.0381 (8)
O5	0.0755 (8)	0.0936 (8)	0.0909 (8)	0.0321 (6)	0.0160 (6)	−0.0121 (7)
N1	0.0447 (6)	0.0409 (5)	0.0574 (6)	0.0033 (4)	0.0068 (4)	−0.0024 (4)
N2	0.0436 (6)	0.0549 (6)	0.0531 (6)	0.0091 (5)	0.0072 (4)	−0.0030 (5)
N3	0.0818 (9)	0.0435 (6)	0.0781 (9)	0.0063 (6)	0.0150 (7)	−0.0064 (6)
C1	0.0496 (7)	0.0411 (6)	0.0469 (6)	−0.0007 (5)	0.0039 (5)	0.0007 (5)
C2	0.0447 (7)	0.0385 (6)	0.0487 (6)	−0.0007 (5)	0.0057 (5)	0.0010 (5)
C3	0.0455 (7)	0.0391 (6)	0.0496 (6)	0.0004 (5)	0.0093 (5)	−0.0006 (5)
C4	0.0441 (7)	0.0401 (6)	0.0512 (7)	−0.0027 (5)	0.0061 (5)	0.0021 (5)
C5	0.0507 (8)	0.0522 (7)	0.0549 (7)	0.0017 (6)	0.0033 (6)	0.0068 (6)
C6	0.0670 (10)	0.0655 (8)	0.0514 (7)	−0.0037 (7)	0.0104 (7)	0.0098 (6)
C7	0.0629 (9)	0.0732 (9)	0.0613 (8)	0.0010 (7)	0.0224 (7)	0.0042 (7)
C8	0.0559 (9)	0.0780 (9)	0.0680 (9)	0.0149 (7)	0.0182 (7)	0.0120 (7)
C9	0.0512 (8)	0.0549 (7)	0.0557 (7)	0.0056 (6)	0.0097 (6)	0.0095 (6)
C10	0.0553 (8)	0.0580 (7)	0.0533 (7)	0.0044 (6)	0.0079 (6)	0.0104 (6)
C11	0.0618 (10)	0.0788 (10)	0.0678 (9)	0.0127 (7)	0.0022 (7)	0.0209 (8)
C12	0.0745 (11)	0.0693 (9)	0.0543 (8)	−0.0103 (8)	−0.0062 (7)	0.0119 (7)
C13	0.0820 (11)	0.0556 (8)	0.0514 (8)	−0.0096 (7)	0.0054 (7)	−0.0032 (6)
C14	0.0644 (9)	0.0490 (7)	0.0530 (7)	−0.0001 (6)	0.0047 (6)	−0.0043 (6)
C15	0.0483 (7)	0.0411 (6)	0.0498 (7)	−0.0037 (5)	0.0036 (5)	0.0022 (5)
C16	0.0472 (7)	0.0465 (6)	0.0511 (7)	−0.0076 (5)	0.0138 (5)	−0.0034 (5)
C17	0.0606 (8)	0.0454 (6)	0.0569 (7)	−0.0063 (6)	0.0170 (6)	−0.0046 (6)
C18	0.0864 (12)	0.0576 (8)	0.0669 (9)	−0.0111 (8)	0.0263 (8)	−0.0158 (7)
C19	0.0825 (12)	0.0869 (11)	0.0567 (9)	−0.0200 (9)	0.0140 (8)	−0.0232 (8)
C20	0.0652 (10)	0.0960 (12)	0.0588 (9)	−0.0075 (8)	0.0017 (7)	−0.0118 (8)
C21	0.0547 (9)	0.0666 (8)	0.0597 (8)	−0.0003 (6)	0.0029 (6)	−0.0091 (7)
C22	0.0656 (9)	0.0724 (9)	0.0555 (8)	0.0085 (7)	0.0137 (7)	0.0006 (7)
C23	0.0694 (11)	0.1011 (13)	0.0805 (11)	0.0075 (9)	0.0295 (9)	−0.0102 (10)
C24	0.0804 (13)	0.1075 (14)	0.0826 (11)	0.0427 (10)	0.0030 (9)	0.0028 (10)
C25	0.0759 (11)	0.0749 (10)	0.0639 (9)	0.0288 (8)	0.0119 (7)	0.0130 (7)

Geometric parameters (Å, º) top

O1—C1	1.2072 (14)	C16—C17	1.3977 (17)
O2—C9	1.3786 (16)	C16—C21	1.3839 (19)
O2—C10	1.3817 (17)	C17—C18	1.3827 (19)
O3—N3	1.2108 (17)	C18—C19	1.368 (2)
O4—N3	1.214 (2)	C19—C20	1.367 (3)
O5—C23	1.411 (2)	C20—C21	1.383 (2)
O5—C24	1.412 (2)	C22—C23	1.508 (2)
N1—N2	1.4078 (15)	C24—C25	1.500 (3)
N1—C1	1.3546 (16)	C3—H3	0.9800
N1—C3	1.4757 (15)	C5—H5	0.9300
N2—C22	1.4635 (17)	C6—H6	0.9300
N2—C25	1.4655 (18)	C7—H7	0.9300
N3—C17	1.4659 (19)	C8—H8	0.9300
C1—C2	1.5456 (17)	C11—H11	0.9300
C2—C3	1.5989 (17)	C12—H12	0.9300
C2—C4	1.5055 (17)	C13—H13	0.9300
C2—C15	1.5071 (17)	C14—H14	0.9300
C3—C16	1.5084 (17)	C18—H18	0.9300
C4—C5	1.3919 (17)	C19—H19	0.9300
C4—C9	1.3769 (18)	C20—H20	0.9300
C5—C6	1.3761 (19)	C21—H21	0.9300
C6—C7	1.373 (2)	C22—H22A	0.9700
C7—C8	1.370 (2)	C22—H22B	0.9700
C8—C9	1.387 (2)	C23—H23A	0.9700
C10—C11	1.384 (2)	C23—H23B	0.9700
C10—C15	1.3756 (19)	C24—H24A	0.9700
C11—C12	1.371 (2)	C24—H24B	0.9700
C12—C13	1.373 (2)	C25—H25A	0.9700
C13—C14	1.3743 (19)	C25—H25B	0.9700
C14—C15	1.3902 (18)

C9—O2—C10	118.08 (11)	C16—C21—C20	122.45 (14)
C23—O5—C24	109.10 (14)	N2—C22—C23	108.31 (12)
N2—N1—C1	132.68 (10)	O5—C23—C22	111.54 (14)
N2—N1—C3	128.25 (9)	O5—C24—C25	110.85 (14)
C1—N1—C3	97.05 (9)	N2—C25—C24	108.79 (14)
N1—N2—C22	111.11 (10)	N1—C3—H3	112.00
N1—N2—C25	110.09 (10)	C2—C3—H3	112.00
C22—N2—C25	109.78 (10)	C16—C3—H3	112.00
O3—N3—O4	122.62 (15)	C4—C5—H5	119.00
O3—N3—C17	119.36 (12)	C6—C5—H5	119.00
O4—N3—C17	118.02 (14)	C5—C6—H6	120.00
O1—C1—N1	132.94 (12)	C7—C6—H6	120.00
O1—C1—C2	134.74 (12)	C6—C7—H7	120.00
N1—C1—C2	92.26 (9)	C8—C7—H7	120.00
C1—C2—C3	84.86 (9)	C7—C8—H8	120.00
C1—C2—C4	115.94 (9)	C9—C8—H8	120.00
C1—C2—C15	111.77 (9)	C10—C11—H11	120.00
C3—C2—C4	117.12 (9)	C12—C11—H11	120.00
C3—C2—C15	113.79 (9)	C11—C12—H12	120.00
C4—C2—C15	111.09 (10)	C13—C12—H12	120.00
N1—C3—C2	85.81 (8)	C12—C13—H13	120.00
N1—C3—C16	114.57 (9)	C14—C13—H13	120.00
C2—C3—C16	119.27 (10)	C13—C14—H14	119.00
C2—C4—C5	122.55 (11)	C15—C14—H14	119.00
C2—C4—C9	120.18 (10)	C17—C18—H18	120.00
C5—C4—C9	117.26 (11)	C19—C18—H18	120.00
C4—C5—C6	121.69 (12)	C18—C19—H19	120.00
C5—C6—C7	119.47 (13)	C20—C19—H19	120.00
C6—C7—C8	120.49 (14)	C19—C20—H20	120.00
C7—C8—C9	119.32 (14)	C21—C20—H20	120.00
O2—C9—C4	122.59 (11)	C16—C21—H21	119.00
O2—C9—C8	115.65 (12)	C20—C21—H21	119.00
C4—C9—C8	121.76 (12)	N2—C22—H22A	110.00
O2—C10—C11	115.87 (13)	N2—C22—H22B	110.00
O2—C10—C15	122.24 (11)	C23—C22—H22A	110.00
C11—C10—C15	121.89 (13)	C23—C22—H22B	110.00
C10—C11—C12	119.27 (15)	H22A—C22—H22B	108.00
C11—C12—C13	120.38 (14)	O5—C23—H23A	109.00
C12—C13—C14	119.40 (13)	O5—C23—H23B	109.00
C13—C14—C15	121.81 (13)	C22—C23—H23A	109.00
C2—C15—C10	120.43 (11)	C22—C23—H23B	109.00
C2—C15—C14	122.43 (12)	H23A—C23—H23B	108.00
C10—C15—C14	117.13 (12)	O5—C24—H24A	109.00
C3—C16—C17	124.60 (11)	O5—C24—H24B	109.00
C3—C16—C21	119.98 (11)	C25—C24—H24A	109.00
C17—C16—C21	115.42 (12)	C25—C24—H24B	109.00
N3—C17—C16	120.88 (11)	H24A—C24—H24B	108.00
N3—C17—C18	116.45 (12)	N2—C25—H25A	110.00
C16—C17—C18	122.65 (13)	N2—C25—H25B	110.00
C17—C18—C19	119.66 (14)	C24—C25—H25A	110.00
C18—C19—C20	119.61 (14)	C24—C25—H25B	110.00
C19—C20—C21	120.21 (15)	H25A—C25—H25B	108.00

C9—O2—C10—C11	−164.66 (13)	C15—C2—C3—C16	−131.34 (11)
C9—O2—C10—C15	15.67 (19)	C15—C2—C4—C5	−160.75 (11)
C10—O2—C9—C4	−16.61 (19)	C1—C2—C4—C9	148.72 (11)
C10—O2—C9—C8	162.73 (13)	C15—C2—C4—C9	19.71 (15)
C23—O5—C24—C25	−61.03 (18)	C15—C2—C3—N1	112.75 (10)
C24—O5—C23—C22	60.87 (18)	C2—C3—C16—C17	70.79 (16)
N2—N1—C1—O1	−11.8 (2)	C2—C3—C16—C21	−108.37 (14)
C3—N1—N2—C25	−149.25 (11)	N1—C3—C16—C21	−8.93 (17)
C1—N1—N2—C22	−71.02 (15)	N1—C3—C16—C17	170.23 (11)
C3—N1—N2—C22	88.92 (13)	C5—C4—C9—C8	−1.01 (19)
N2—N1—C3—C2	−166.66 (11)	C2—C4—C5—C6	−179.05 (12)
C1—N1—C3—C2	−1.38 (9)	C2—C4—C9—C8	178.56 (12)
N2—N1—C3—C16	72.97 (14)	C5—C4—C9—O2	178.30 (12)
C3—N1—C1—O1	−176.04 (14)	C2—C4—C9—O2	−2.14 (19)
N2—N1—C1—C2	165.68 (11)	C9—C4—C5—C6	0.51 (19)
C1—N1—N2—C25	50.80 (16)	C4—C5—C6—C7	0.5 (2)
C3—N1—C1—C2	1.42 (9)	C5—C6—C7—C8	−0.9 (2)
C1—N1—C3—C16	−121.74 (11)	C6—C7—C8—C9	0.5 (2)
C22—N2—C25—C24	−58.02 (15)	C7—C8—C9—C4	0.6 (2)
N1—N2—C22—C23	179.19 (11)	C7—C8—C9—O2	−178.80 (13)
C25—N2—C22—C23	57.18 (16)	C11—C10—C15—C14	3.1 (2)
N1—N2—C25—C24	179.37 (12)	O2—C10—C11—C12	178.81 (14)
O3—N3—C17—C18	−159.81 (14)	O2—C10—C15—C14	−177.26 (12)
O4—N3—C17—C16	−161.84 (14)	C11—C10—C15—C2	−175.75 (13)
O3—N3—C17—C16	18.9 (2)	O2—C10—C15—C2	3.91 (19)
O4—N3—C17—C18	19.4 (2)	C15—C10—C11—C12	−1.5 (2)
N1—C1—C2—C4	116.42 (11)	C10—C11—C12—C13	−1.7 (2)
N1—C1—C2—C15	−114.90 (10)	C11—C12—C13—C14	3.1 (2)
O1—C1—C2—C3	176.08 (14)	C12—C13—C14—C15	−1.5 (2)
N1—C1—C2—C3	−1.31 (8)	C13—C14—C15—C2	177.22 (12)
O1—C1—C2—C4	−66.19 (18)	C13—C14—C15—C10	−1.6 (2)
O1—C1—C2—C15	62.49 (18)	C3—C16—C17—C18	179.68 (13)
C1—C2—C3—N1	1.20 (8)	C17—C16—C21—C20	1.2 (2)
C4—C2—C3—N1	−115.37 (10)	C21—C16—C17—N3	−179.79 (12)
C1—C2—C3—C16	117.11 (10)	C3—C16—C17—N3	1.0 (2)
C4—C2—C3—C16	0.54 (15)	C21—C16—C17—C18	−1.1 (2)
C1—C2—C4—C5	−31.73 (16)	C3—C16—C21—C20	−179.54 (13)
C4—C2—C15—C10	−20.60 (16)	N3—C17—C18—C19	178.99 (14)
C4—C2—C15—C14	160.64 (11)	C16—C17—C18—C19	0.3 (2)
C3—C2—C4—C9	−113.39 (13)	C17—C18—C19—C20	0.6 (3)
C3—C2—C4—C5	66.16 (15)	C18—C19—C20—C21	−0.5 (3)
C1—C2—C15—C10	−151.80 (12)	C19—C20—C21—C16	−0.5 (2)
C1—C2—C15—C14	29.43 (16)	N2—C22—C23—O5	−59.13 (17)
C3—C2—C15—C10	114.15 (13)	O5—C24—C25—N2	59.98 (18)
C3—C2—C15—C14	−64.62 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.98	2.55	3.5310 (16)	174
C6—H6···O1ⁱⁱ	0.93	2.56	3.3828 (17)	148
C11—H11···O2ⁱⁱⁱ	0.93	2.50	3.389 (2)	159

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O3ⁱ	0.98	2.55	3.5310 (16)	174
C6—H6···O1ⁱⁱ	0.93	2.56	3.3828 (17)	148
C11—H11···O2ⁱⁱⁱ	0.93	2.50	3.389 (2)	159

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, −y+3/2, z−1/2; (iii) −x+2, −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).

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
Arya, N., Jagdale, A. Y., Patil, T. A., Yeramwar, S. S., Holikatti, S. S., Dwivedi, J., Shishoo, Ch. J. & Jain, K. S. (2014). Eur. J. Med. Chem. 74, 619–656. 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
Çelik, Í., Akkurt, M., Jarrahpour, A., Heiran, R. & Özdemir, N. (2014). Acta Cryst. E70, o369–o370. CSD CrossRef IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Ebrahimi, E. & Jarrahpour, A. (2014). Iran. J. Sci. Technol. 38A1, 49–53. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jarrahpour, A. & Ebrahimi, E. (2010). Molecules, 15, 515–531. Web of Science CSD CrossRef CAS PubMed 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., D'hooghe, M. & De Kimpe, N. (2011). Tetrahedron, 67, 1989–2012. Web of Science CrossRef CAS Google Scholar
Singh, G. S. & Sudheesh, S. (2014). Arkivoc, i, 337–385. Web of Science CrossRef 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
Zarei, M., Karimi-Jaberi, Z. & Movahedi, A. (2013). Synth. Commun. 43, 728–734. Web of Science CrossRef CAS Google Scholar
Zeng, X.-H., Wang, H.-M., Yan, Y.-M., Wu, L. & Ding, M.-W. (2014). Tetrahedron, 70, 3647–3652. Web of Science CSD CrossRef CAS Google Scholar