1-(4-Meth­oxy­phen­yl)-4-(3-nitro­phen­yl)-3-phen­oxy­azetidin-2-one

Baktır, Z.; Akkurt, M.; Jarrahpour, A.; Heiran, R.

doi:10.1107/S1600536811003382

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages o537-o538

doi:10.1107/S1600536811003382

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1-(4-Methoxyphenyl)-4-(3-nitrophenyl)-3-phenoxyazetidin-2-one

Zeliha Baktır,^a Mehmet Akkurt,^a ^* Aliasghar Jarrahpour ^b and Roghaye Heiran ^b

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 6 January 2011; accepted 25 January 2011; online 29 January 2011)

In the title compound, C₂₂H₁₈N₂O₅, the four-membered β-lactam ring is nearly planar, with a maximum deviation of 0.023 (2) Å for the N atom, and has long C—C distances of 1.525 (5) and 1.571 (5) Å. The mean plane of this group makes dihedral angles of 11.61 (19), 74.5 (2) and 72.3 (2)° with three aromatic rings. An intramolecular C—H⋯O hydrogen bond occurs. The packing of the molecules in the crystal structure is governed mainly by intermolecular C—H⋯O hydrogen-bonding and C—H⋯π stacking interactions. Furthermore, a π–π interaction [centroid–centroid distance = 3.6129 (19) Å] helps to stabilize the crystal structure.

Related literature

For general background to β-lactams, see: Jubie et al. (2009 ); Mehta et al. (2010 ); Vatmurge et al. (2008 ); Von Nussbaum et al. (2006 ). For related structures, see: Akkurt et al. (2006 ); Ercan et al. (1996a ,b ); Kabak et al. (1999 ).

Experimental

Crystal data

C₂₂H₁₈N₂O₅
M_r = 390.38
Triclinic, $[P \overline 1]$
a = 7.7934 (4) Å
b = 11.2813 (3) Å
c = 11.8818 (2) Å
α = 77.771 (4)°
β = 80.948 (5)°
γ = 71.052 (4)°
V = 961.18 (6) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 294 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.981, T_max = 0.981
3928 measured reflections
3928 independent reflections
1872 reflections with I > 2σ(I)
R_int = 0.104

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.155
S = 1.01
3927 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg4 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2	0.93	2.53	3.125 (4)	122
C2—H2⋯O2ⁱ	0.93	2.59	3.464 (4)	156
C16—H16⋯O4ⁱⁱ	0.93	2.52	3.164 (5)	126
C4—H4⋯Cg4ⁱⁱⁱ	0.93	2.89	3.716 (4)	149
C9—H9⋯Cg2^iv	0.98	2.55	3.463 (4)	154
Symmetry codes: (i) -x, -y+1, -z+2; (ii) x-1, y, z; (iii) x, y-1, z; (iv) -x+1, -y+1, -z+2.

Data collection: CrystalClear (Rigaku/MSC, 2005 ); cell refinement: CrystalClear; data reduction: CrystalClear; 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/S1600536811003382/bv2175sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003382/bv2175Isup2.hkl

checkCIF report

Comment top

Azetidine-2-ones (β-lactams) were the first group of antibacterial natural products introduced as a therapeutic treatment of bacterial infections (Von Nussbaum et al.. 2006). The biological activity of β-lactams is mostly believed to be associated with the chemical reactivity of their β-lactam ring and on its substituents, especially at the nitrogen of the 2-azetidinone ring (Mehta et al. 2010). p-Anisidine derivatives have been found to be biologically interesting for many years (Jubie et al. 2009). Continuous change in the structures of known active compounds and the preparation of new types (Vatmurge et al. 2008) has been forced by the development of bacterial resistance to known compounds (Vatmurge et al. 2008).

In the title compound (I), (Fig. 1), the β-lactam ring (N1/C8–C10) is nearly planar, with a maximum deviation of 0.023 (2)Å for N1. The bond lengths in the β-lactam ring are comparable with those found in previous similar studies (Akkurt et al. 2006; Ercan et al., 1996a,b; Kabak et al., 1999).

Its mean plane makes dihedral angles of 11.61 (19), 74.5 (2) and 72.3 (2)°, respectively, with three aromatic rings (C1–C6), (C11–C16) and (C17–C22). The details of the dihedral angles between the planes of the rings are given in Table 2.

A weak intramolecular C—H···O hydrogen bond contributes to the stability of the molecular configuration (Table 1). The crystal structure is stabilized by intermolecular C—H···O hydrogen-bonding (Table 1, Fig. 2) and C—H···π stacking interactions (Table 1). Furthermore, a π-π interaction [Cg1···Cg3(x, y, z) = 3.6129 (19) Å, Cg1 and Cg3 are the centroids of the N1/C8–C10 β-lactam ring and the C11–CC16 benzene rings, respectively] helps to stabilize the crystal structure.

Related literature top

For general background to β-lactams, see: Jubie et al. (2009); Mehta et al. (2010); Vatmurge et al. (2008); Von Nussbaum et al. (2006). For related structures, see: Akkurt et al. (2006); Ercan et al. (1996a,b); Kabak et al. (1999).

Experimental top

A mixture of N-(3-nitrobenzylidene)-4-methoxybenzeneamine (1.28 g, 5.00 mmol) and triethylamine (2.53 g, 25.00 mmol), phenoxyacetic acid (1.14 g, 7.50 mmol) and tosyl chloride (1.43 g, 7.50 mmol) in CH₂Cl₂ (30 ml) was stirred at room temperature overnight. Then it was washed with HCl 1 N, saturated sodium bicarbonate solution and brine, dried with Na₂SO₄ and the solvent was evaporated to give the crude product as a white crystal which was then purified by recrystallization from ethyl acetate (Yield 47%). [mp: 415° K]. IR (KBr, cm^-1): 1739.7 (CO β-lactam). ¹H NMR (250 MHz, CDCl₃) δ 3.75 (Me, s, 3H), 5.48 (H-8, d, 1H, J = 4.75), 5.63 (H-9, d, 1H, J = 4.75), 6.75–8.23 (ArH, m, 13H); ¹³C NMR (62.9 MHz, CDCl₃) δ 55.46 (Me), 61.02 (C-8), 81.01 (C-9), 114.62–156.83 (aromatic carbons), 161.86 (CO β-lactam); GC—MS m/z =390 [M+].

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); 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).

Figures top

	Fig. 1. The title molecule with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The packing diagram and the hydrogen bonding interactions of (I), viewing down the a axis.

1-(4-Methoxyphenyl)-4-(3-nitrophenyl)-3-phenoxyazetidin-2-one top

Crystal data top

C₂₂H₁₈N₂O₅	Z = 2
M_r = 390.38	F(000) = 408
Triclinic, P1	D_x = 1.349 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7934 (4) Å	Cell parameters from 2243 reflections
b = 11.2813 (3) Å	θ = 2.4–26.4°
c = 11.8818 (2) Å	µ = 0.10 mm⁻¹
α = 77.771 (4)°	T = 294 K
β = 80.948 (5)°	Block, white
γ = 71.052 (4)°	0.20 × 0.20 × 0.20 mm
V = 961.18 (6) Å³

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3928 independent reflections
Radiation source: Sealed Tube	1872 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.104
Detector resolution: 10.0000 pixels mm^-1	θ_max = 26.4°, θ_min = 2.4°
dtprofit.ref scans	h = −9→8
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −14→14
T_min = 0.981, T_max = 0.981	l = −14→14
3928 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.059	H-atom parameters constrained
wR(F²) = 0.155	w = 1/[σ²(F_o²) + (0.0375P)² + 0.1692P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
3927 reflections	Δρ_max = 0.14 e Å⁻³
265 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), FC^*=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.011 (2)

Crystal data top

C₂₂H₁₈N₂O₅	γ = 71.052 (4)°
M_r = 390.38	V = 961.18 (6) Å³
Triclinic, P1	Z = 2
a = 7.7934 (4) Å	Mo Kα radiation
b = 11.2813 (3) Å	µ = 0.10 mm⁻¹
c = 11.8818 (2) Å	T = 294 K
α = 77.771 (4)°	0.20 × 0.20 × 0.20 mm
β = 80.948 (5)°

Data collection top

Rigaku R-AXIS RAPID-S diffractometer	3928 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1872 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.981	R_int = 0.104
3928 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.155	H-atom parameters constrained
S = 1.01	Δρ_max = 0.14 e Å⁻³
3927 reflections	Δρ_min = −0.15 e Å⁻³
265 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	0.3243 (3)	0.0941 (2)	0.8790 (2)	0.0917 (11)
O2	0.1966 (3)	0.7038 (2)	0.9341 (2)	0.0857 (10)
O3	0.4720 (3)	0.83418 (19)	0.77456 (17)	0.0652 (8)
O4	1.1375 (4)	0.6731 (3)	0.5285 (3)	0.1139 (15)
O5	1.0633 (4)	0.6949 (3)	0.3578 (2)	0.1081 (12)
N1	0.4469 (3)	0.5569 (2)	0.85135 (19)	0.0577 (9)
N2	1.0324 (4)	0.6750 (3)	0.4631 (3)	0.0780 (12)
C1	0.2353 (4)	0.4324 (3)	0.8902 (2)	0.0624 (11)
C2	0.2021 (4)	0.3172 (3)	0.8986 (2)	0.0647 (12)
C3	0.3412 (5)	0.2117 (3)	0.8731 (3)	0.0666 (12)
C4	0.5155 (4)	0.2219 (3)	0.8378 (3)	0.0671 (12)
C5	0.5496 (4)	0.3360 (3)	0.8297 (2)	0.0610 (11)
C6	0.4099 (4)	0.4414 (3)	0.8569 (2)	0.0553 (11)
C7	0.1492 (5)	0.0772 (4)	0.9103 (4)	0.1053 (17)
C8	0.6129 (4)	0.5948 (3)	0.8068 (2)	0.0558 (11)
C9	0.5111 (4)	0.7211 (3)	0.8556 (3)	0.0615 (11)
C10	0.3500 (5)	0.6679 (3)	0.8888 (3)	0.0644 (11)
C11	0.6576 (4)	0.6108 (3)	0.6781 (2)	0.0508 (10)
C12	0.8247 (4)	0.6260 (3)	0.6300 (2)	0.0540 (11)
C13	0.8581 (4)	0.6524 (3)	0.5124 (3)	0.0581 (11)
C14	0.7338 (4)	0.6619 (3)	0.4389 (3)	0.0670 (11)
C15	0.5691 (4)	0.6437 (3)	0.4861 (3)	0.0686 (14)
C16	0.5310 (4)	0.6203 (3)	0.6038 (2)	0.0587 (11)
C17	0.6128 (5)	0.8875 (3)	0.7357 (3)	0.0613 (11)
C18	0.7756 (5)	0.8490 (3)	0.7842 (3)	0.0723 (14)
C19	0.9081 (5)	0.9080 (4)	0.7365 (3)	0.0854 (17)
C20	0.8791 (6)	1.0018 (4)	0.6426 (4)	0.0912 (17)
C21	0.7173 (6)	1.0394 (4)	0.5945 (3)	0.0921 (19)
C22	0.5827 (5)	0.9832 (3)	0.6415 (3)	0.0776 (14)
H1	0.14070	0.50350	0.90690	0.0750*
H2	0.08510	0.31120	0.92160	0.0780*
H4	0.60970	0.15120	0.81950	0.0800*
H5	0.66640	0.34220	0.80600	0.0730*
H7A	0.10340	0.09920	0.98540	0.1580*
H7B	0.15800	−0.01000	0.91200	0.1580*
H7C	0.06770	0.13100	0.85450	0.1580*
H8	0.71820	0.54210	0.84860	0.0670*
H9	0.56390	0.72760	0.92280	0.0740*
H12	0.91340	0.61820	0.67740	0.0650*
H14	0.75970	0.68020	0.35910	0.0800*
H15	0.48370	0.64740	0.43790	0.0820*
H16	0.41810	0.61050	0.63460	0.0700*
H18	0.79670	0.78430	0.84820	0.0870*
H19	1.01790	0.88290	0.76940	0.1020*
H20	0.96880	1.04030	0.61090	0.1100*
H21	0.69770	1.10320	0.52980	0.1110*
H22	0.47220	1.01030	0.60930	0.0930*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0952 (19)	0.0874 (18)	0.110 (2)	−0.0523 (15)	0.0269 (15)	−0.0420 (15)
O2	0.0738 (17)	0.0895 (18)	0.0920 (18)	−0.0269 (13)	0.0240 (14)	−0.0320 (14)
O3	0.0733 (15)	0.0599 (14)	0.0622 (14)	−0.0235 (11)	−0.0041 (11)	−0.0064 (11)
O4	0.0638 (18)	0.150 (3)	0.132 (3)	−0.0557 (18)	−0.0014 (17)	−0.002 (2)
O5	0.100 (2)	0.125 (2)	0.093 (2)	−0.0523 (17)	0.0469 (16)	−0.0176 (17)
N1	0.0566 (16)	0.0636 (17)	0.0527 (15)	−0.0266 (13)	0.0096 (12)	−0.0074 (13)
N2	0.066 (2)	0.073 (2)	0.089 (2)	−0.0289 (16)	0.0230 (18)	−0.0109 (18)
C1	0.061 (2)	0.068 (2)	0.0576 (19)	−0.0229 (17)	0.0046 (15)	−0.0116 (16)
C2	0.060 (2)	0.082 (2)	0.058 (2)	−0.0335 (19)	0.0078 (15)	−0.0154 (18)
C3	0.078 (2)	0.073 (2)	0.058 (2)	−0.040 (2)	0.0147 (17)	−0.0195 (17)
C4	0.071 (2)	0.074 (2)	0.060 (2)	−0.0284 (18)	0.0115 (16)	−0.0220 (17)
C5	0.059 (2)	0.072 (2)	0.0531 (18)	−0.0277 (17)	0.0127 (15)	−0.0139 (16)
C6	0.062 (2)	0.063 (2)	0.0427 (17)	−0.0280 (16)	0.0036 (14)	−0.0046 (14)
C7	0.109 (3)	0.104 (3)	0.129 (3)	−0.072 (3)	0.032 (3)	−0.045 (3)
C8	0.0566 (18)	0.064 (2)	0.0481 (17)	−0.0249 (16)	−0.0026 (14)	−0.0034 (15)
C9	0.073 (2)	0.066 (2)	0.0484 (17)	−0.0280 (17)	−0.0021 (15)	−0.0074 (16)
C10	0.067 (2)	0.071 (2)	0.0538 (19)	−0.0251 (18)	0.0074 (16)	−0.0105 (17)
C11	0.0441 (16)	0.0544 (18)	0.0525 (17)	−0.0175 (14)	0.0017 (13)	−0.0069 (14)
C12	0.0482 (18)	0.0548 (18)	0.0591 (19)	−0.0182 (14)	−0.0016 (14)	−0.0084 (15)
C13	0.0485 (18)	0.0530 (18)	0.068 (2)	−0.0188 (14)	0.0132 (15)	−0.0084 (16)
C14	0.068 (2)	0.075 (2)	0.0521 (19)	−0.0229 (18)	0.0069 (16)	−0.0058 (16)
C15	0.064 (2)	0.090 (3)	0.056 (2)	−0.0313 (19)	−0.0026 (16)	−0.0112 (18)
C16	0.0503 (18)	0.072 (2)	0.0570 (19)	−0.0273 (16)	0.0007 (14)	−0.0085 (16)
C17	0.074 (2)	0.057 (2)	0.0542 (19)	−0.0249 (17)	0.0033 (16)	−0.0115 (16)
C18	0.087 (3)	0.072 (2)	0.065 (2)	−0.036 (2)	−0.0066 (19)	−0.0086 (18)
C19	0.092 (3)	0.086 (3)	0.087 (3)	−0.044 (2)	0.000 (2)	−0.013 (2)
C20	0.109 (3)	0.081 (3)	0.089 (3)	−0.049 (3)	0.020 (3)	−0.016 (2)
C21	0.120 (4)	0.067 (3)	0.075 (3)	−0.030 (3)	0.014 (3)	0.004 (2)
C22	0.093 (3)	0.067 (2)	0.061 (2)	−0.018 (2)	−0.0005 (19)	−0.0004 (18)

Geometric parameters (Å, º) top

O1—C3	1.361 (4)	C15—C16	1.370 (4)
O1—C7	1.420 (5)	C17—C18	1.377 (6)
O2—C10	1.208 (5)	C17—C22	1.371 (5)
O3—C9	1.403 (4)	C18—C19	1.390 (6)
O3—C17	1.390 (5)	C19—C20	1.356 (6)
O4—N2	1.207 (5)	C20—C21	1.369 (7)
O5—N2	1.223 (4)	C21—C22	1.383 (6)
N1—C6	1.410 (4)	C1—H1	0.9300
N1—C8	1.478 (4)	C2—H2	0.9300
N1—C10	1.361 (4)	C4—H4	0.9300
N2—C13	1.471 (5)	C5—H5	0.9300
C1—C2	1.386 (5)	C7—H7A	0.9600
C1—C6	1.386 (5)	C7—H7B	0.9600
C2—C3	1.377 (5)	C7—H7C	0.9600
C3—C4	1.392 (5)	C8—H8	0.9800
C4—C5	1.378 (5)	C9—H9	0.9800
C5—C6	1.384 (5)	C12—H12	0.9300
C8—C9	1.571 (5)	C14—H14	0.9300
C8—C11	1.500 (3)	C15—H15	0.9300
C9—C10	1.525 (5)	C16—H16	0.9300
C11—C12	1.386 (5)	C18—H18	0.9300
C11—C16	1.389 (4)	C19—H19	0.9300
C12—C13	1.367 (4)	C20—H20	0.9300
C13—C14	1.368 (5)	C21—H21	0.9300
C14—C15	1.378 (5)	C22—H22	0.9300

O1···O3ⁱ	3.219 (3)	C5···H9^vii	2.9400
O1···C17ⁱ	3.234 (4)	C5···H8	3.0800
O1···C22ⁱ	3.414 (4)	C6···H16	2.9200
O2···O3	3.155 (3)	C6···H9^vii	2.8900
O2···C1	3.125 (4)	C7···H2	2.5500
O3···C16	3.348 (4)	C8···H18	3.0900
O3···O1ⁱⁱ	3.219 (3)	C8···H5	2.7400
O3···O2	3.155 (3)	C9···H18	2.5300
O3···N1	3.129 (3)	C10···H1	2.8000
O4···C15ⁱⁱⁱ	3.239 (5)	C11···H5	3.0700
O4···C16ⁱⁱⁱ	3.164 (5)	C15···H21^ix	2.9200
O5···C12^iv	3.414 (5)	C18···H9	2.6400
O2···H7A^v	2.8500	C18···H12	2.9500
O2···H19^vi	2.6800	C20···H4ⁱⁱ	3.0800
O2···H2^v	2.5900	C21···H4ⁱⁱ	3.0800
O2···H1	2.5300	C22···H22^ix	3.0600
O4···H12	2.4100	H1···O2	2.5300
O4···H16ⁱⁱⁱ	2.5200	H1···C10	2.8000
O4···H15ⁱⁱⁱ	2.6900	H2···C7	2.5500
O5···H14	2.4200	H2···H7A	2.3200
O5···H5^iv	2.6200	H2···H7C	2.3800
N1···O3	3.129 (3)	H2···O2^v	2.5900
N1···H16	2.5500	H4···C20ⁱ	3.0800
C1···O2	3.125 (4)	H4···C21ⁱ	3.0800
C5···C10^vii	3.541 (4)	H5···C8	2.7400
C5···C11	3.524 (4)	H5···C11	3.0700
C6···C9^vii	3.562 (4)	H5···H8	2.5800
C6···C16	3.432 (4)	H5···O5^iv	2.6200
C6···C10^vii	3.585 (5)	H7A···C2	2.7600
C7···C7^viii	3.533 (6)	H7A···H2	2.3200
C8···C18	3.440 (5)	H7A···O2^v	2.8500
C9···C6^vii	3.562 (4)	H7A···H7B^viii	2.5800
C10···C6^vii	3.585 (5)	H7B···H7A^viii	2.5800
C10···C5^vii	3.541 (4)	H7C···C2	2.8000
C10···C16	3.539 (4)	H7C···H2	2.3800
C11···C17	3.234 (5)	H8···C5	3.0800
C11···C5	3.524 (4)	H8···H5	2.5800
C12···C18	3.307 (5)	H8···H12	2.5100
C12···C17	3.280 (5)	H9···C18	2.6400
C12···O5^iv	3.414 (5)	H9···H18	2.1200
C13···C13^iv	3.477 (5)	H9···C1^vii	2.8600
C15···C21^ix	3.567 (5)	H9···C2^vii	2.8700
C15···O4^vi	3.239 (5)	H9···C3^vii	2.9100
C16···O3	3.348 (4)	H9···C4^vii	2.9500
C16···C6	3.432 (4)	H9···C5^vii	2.9400
C16···C10	3.539 (4)	H9···C6^vii	2.8900
C16···O4^vi	3.164 (5)	H12···O4	2.4100
C17···C12	3.280 (5)	H12···C18	2.9500
C17···O1ⁱⁱ	3.234 (4)	H12···H8	2.5100
C17···C11	3.234 (5)	H14···O5	2.4200
C18···C8	3.440 (5)	H14···C2^x	3.0200
C18···C12	3.307 (5)	H14···C3^x	2.8900
C21···C15^ix	3.567 (5)	H15···O4^vi	2.6900
C22···O1ⁱⁱ	3.414 (4)	H16···O4^vi	2.5200
C1···H9^vii	2.8600	H16···N1	2.5500
C2···H7C	2.8000	H16···C6	2.9200
C2···H18^vii	2.9800	H18···C8	3.0900
C2···H14^x	3.0200	H18···C9	2.5300
C2···H9^vii	2.8700	H18···H9	2.1200
C2···H7A	2.7600	H18···C2^vii	2.9800
C3···H14^x	2.8900	H19···O2ⁱⁱⁱ	2.6800
C3···H9^vii	2.9100	H21···C15^ix	2.9200
C4···H9^vii	2.9500	H22···C22^ix	3.0600

C3—O1—C7	118.6 (3)	C19—C20—C21	119.7 (4)
C9—O3—C17	116.9 (3)	C20—C21—C22	120.5 (4)
C6—N1—C8	130.9 (2)	C17—C22—C21	119.8 (4)
C6—N1—C10	133.3 (3)	C2—C1—H1	120.00
C8—N1—C10	95.8 (2)	C6—C1—H1	120.00
O4—N2—O5	123.3 (4)	C1—C2—H2	120.00
O4—N2—C13	118.4 (3)	C3—C2—H2	120.00
O5—N2—C13	118.2 (3)	C3—C4—H4	120.00
C2—C1—C6	119.9 (3)	C5—C4—H4	120.00
C1—C2—C3	120.4 (3)	C4—C5—H5	120.00
O1—C3—C2	125.4 (3)	C6—C5—H5	120.00
O1—C3—C4	115.2 (3)	O1—C7—H7A	109.00
C2—C3—C4	119.4 (3)	O1—C7—H7B	109.00
C3—C4—C5	120.5 (3)	O1—C7—H7C	109.00
C4—C5—C6	119.9 (3)	H7A—C7—H7B	109.00
N1—C6—C1	120.6 (3)	H7A—C7—H7C	110.00
N1—C6—C5	119.6 (3)	H7B—C7—H7C	109.00
C1—C6—C5	119.9 (3)	N1—C8—H8	112.00
N1—C8—C9	86.1 (2)	C9—C8—H8	112.00
N1—C8—C11	115.7 (2)	C11—C8—H8	112.00
C9—C8—C11	115.3 (3)	O3—C9—H9	113.00
O3—C9—C8	116.7 (3)	C8—C9—H9	113.00
O3—C9—C10	112.6 (3)	C10—C9—H9	113.00
C8—C9—C10	85.8 (2)	C11—C12—H12	120.00
O2—C10—N1	131.9 (3)	C13—C12—H12	120.00
O2—C10—C9	135.9 (3)	C13—C14—H14	121.00
N1—C10—C9	92.2 (3)	C15—C14—H14	121.00
C8—C11—C12	119.8 (3)	C14—C15—H15	120.00
C8—C11—C16	121.9 (3)	C16—C15—H15	120.00
C12—C11—C16	118.2 (2)	C11—C16—H16	119.00
C11—C12—C13	119.5 (3)	C15—C16—H16	119.00
N2—C13—C12	118.7 (3)	C17—C18—H18	120.00
N2—C13—C14	118.7 (3)	C19—C18—H18	120.00
C12—C13—C14	122.5 (3)	C18—C19—H19	120.00
C13—C14—C15	118.3 (3)	C20—C19—H19	120.00
C14—C15—C16	120.2 (3)	C19—C20—H20	120.00
C11—C16—C15	121.4 (3)	C21—C20—H20	120.00
O3—C17—C18	124.4 (3)	C20—C21—H21	120.00
O3—C17—C22	115.6 (3)	C22—C21—H21	120.00
C18—C17—C22	120.0 (4)	C17—C22—H22	120.00
C17—C18—C19	119.3 (3)	C21—C22—H22	120.00
C18—C19—C20	120.7 (4)

C7—O1—C3—C4	−177.8 (3)	C4—C5—C6—N1	178.3 (3)
C7—O1—C3—C2	2.1 (5)	C9—C8—C11—C12	92.0 (4)
C17—O3—C9—C10	−177.7 (3)	N1—C8—C11—C16	15.1 (4)
C9—O3—C17—C22	168.1 (3)	N1—C8—C11—C12	−169.7 (3)
C17—O3—C9—C8	−80.8 (3)	N1—C8—C9—O3	−116.3 (3)
C9—O3—C17—C18	−10.9 (4)	N1—C8—C9—C10	−3.0 (2)
C6—N1—C10—O2	−4.2 (6)	C9—C8—C11—C16	−83.2 (4)
C6—N1—C8—C9	−173.9 (3)	C11—C8—C9—O3	0.4 (4)
C10—N1—C8—C9	3.4 (2)	C11—C8—C9—C10	113.7 (3)
C8—N1—C6—C1	−172.3 (2)	C8—C9—C10—N1	3.2 (2)
C8—N1—C10—O2	178.7 (4)	C8—C9—C10—O2	−179.0 (4)
C8—N1—C10—C9	−3.4 (2)	O3—C9—C10—N1	120.5 (3)
C8—N1—C6—C5	8.2 (4)	O3—C9—C10—O2	−61.8 (5)
C10—N1—C8—C11	−113.0 (3)	C12—C11—C16—C15	0.2 (5)
C6—N1—C8—C11	69.8 (4)	C16—C11—C12—C13	1.5 (5)
C10—N1—C6—C5	−168.0 (3)	C8—C11—C16—C15	175.4 (3)
C6—N1—C10—C9	173.7 (3)	C8—C11—C12—C13	−173.9 (3)
C10—N1—C6—C1	11.5 (4)	C11—C12—C13—N2	176.8 (3)
O5—N2—C13—C12	177.9 (3)	C11—C12—C13—C14	−1.5 (5)
O4—N2—C13—C14	176.2 (3)	N2—C13—C14—C15	−178.4 (3)
O5—N2—C13—C14	−3.8 (5)	C12—C13—C14—C15	−0.2 (5)
O4—N2—C13—C12	−2.2 (5)	C13—C14—C15—C16	1.8 (5)
C2—C1—C6—N1	−178.1 (2)	C14—C15—C16—C11	−1.8 (5)
C2—C1—C6—C5	1.4 (4)	O3—C17—C18—C19	178.8 (3)
C6—C1—C2—C3	−0.6 (4)	C22—C17—C18—C19	−0.1 (5)
C1—C2—C3—O1	179.6 (3)	O3—C17—C22—C21	−178.1 (3)
C1—C2—C3—C4	−0.5 (5)	C18—C17—C22—C21	1.0 (5)
O1—C3—C4—C5	−179.4 (3)	C17—C18—C19—C20	−0.6 (6)
C2—C3—C4—C5	0.8 (5)	C18—C19—C20—C21	0.4 (6)
C3—C4—C5—C6	0.1 (5)	C19—C20—C21—C22	0.5 (6)
C4—C5—C6—C1	−1.2 (4)	C20—C21—C22—C17	−1.2 (6)

Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x+1, y, z; (iv) −x+2, −y+1, −z+1; (v) −x, −y+1, −z+2; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+2; (viii) −x, −y, −z+2; (ix) −x+1, −y+2, −z+1; (x) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2	0.93	2.53	3.125 (4)	122
C2—H2···O2^v	0.93	2.59	3.464 (4)	156
C16—H16···O4^vi	0.93	2.52	3.164 (5)	126
C16—H16···N1	0.93	2.55	2.898 (3)	103
C4—H4···Cg4ⁱ	0.93	2.89	3.716 (4)	149
C9—H9···Cg2^vii	0.98	2.55	3.463 (4)	154

Symmetry codes: (i) x, y−1, z; (v) −x, −y+1, −z+2; (vi) x−1, y, z; (vii) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O₅
M_r	390.38
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.7934 (4), 11.2813 (3), 11.8818 (2)
α, β, γ (°)	77.771 (4), 80.948 (5), 71.052 (4)
V (Å³)	961.18 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku R-AXIS RAPID-S diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.981, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	3928, 3928, 1872
R_int	0.104
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.155, 1.01
No. of reflections	3927
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: CrystalClear (Rigaku/MSC, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg4 are the centroids of the C1–C6 and C17–C22 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2	0.93	2.53	3.125 (4)	122
C2—H2···O2ⁱ	0.93	2.59	3.464 (4)	156
C16—H16···O4ⁱⁱ	0.93	2.52	3.164 (5)	126
C4—H4···Cg4ⁱⁱⁱ	0.93	2.89	3.716 (4)	149
C9—H9···Cg2^iv	0.98	2.55	3.463 (4)	154

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

The dihedral angles (°) between the mean planes of the rings in (I) top

	Ring 2	Ring 3	Ring 4
Ring 1	11.61 (19)	74.5 (2)	72.3 (2)
Ring 2		84.98 (15)	60.96 (16)
Ring 3			36.22 (17)

Ring 1 is the N1/C8–C10 β-lactam ring, Ring 2 is the C1–C6 benzene ring, Ring 3 is the C11–C16 benzene ring and Ring 4 is the C17–C22 benzene ring.

Acknowledgements

ZB and MA thank the Unit of the Scientific Research Projects of Erciyes University, Turkey for the research grant FBD-10–2949 and for support of the data collection at Atatürk University, Turkey. AJ and RH also thank the Shiraz University Research Council for financial support (grant No. 89-GR—SC-23).

References

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Volume 67| Part 2| February 2011| Pages o537-o538

doi:10.1107/S1600536811003382

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