3-(4-Chloro­phen­oxy)-1-(4-meth­oxy­phen­yl)-4-(4-nitro­phen­yl)azetidin-2-one

Butcher, R.J.; Akkurt, M.; Jarrahpour, A.; Badrabady, S.A.T.

doi:10.1107/S1600536811013018

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 5| May 2011| Pages o1101-o1102

doi:10.1107/S1600536811013018

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3-(4-Chlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitrophenyl)azetidin-2-one

Ray J. Butcher,^a Mehmet Akkurt,^b ^* Aliasghar Jarrahpour ^c and Seid Ali Torabi Badrabady ^c

^aDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^cDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 6 April 2011; accepted 7 April 2011; online 13 April 2011)

In the title compound, C₂₂H₁₇ClN₂O₅, the nearly planar four-membered β-lactam ring [maximum deviation of 0.016 (1) for the N atom] makes dihedral angles of 53.07 (9), 73.19 (9) and 6.61 (9)° with the chloro-, nitro- and methoxybenzene rings, respectively. The crystal structure is stabilized by C—H⋯O hydrogen bonds, a weak C—H⋯π interaction and a π–π stacking interaction [centroid–centroid distance = 3.6513 (8) Å] between the methoxybenzene rings of inversion-related molecules.

Related literature

For general background to β-lactams, see: Banik et al. (2004 ); Garud et al. (2009 ); Jarrahpor & Khalili (2007 ); Jarrahpour & Zarei (2006 , 2010 ). For some of our previous reports of the structures of β-lactams, see: Akkurt et al. (2008a ,b , 2011a ,b ); Baktır et al. (2009 ); Yalçın et al. (2009 ); Çelik et al. (2009 ).

Experimental

Crystal data

C₂₂H₁₇ClN₂O₅
M_r = 424.83
Monoclinic, P 2₁ /n
a = 6.0863 (2) Å
b = 20.0855 (7) Å
c = 17.3819 (7) Å
β = 97.419 (4)°
V = 2107.09 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.22 mm⁻¹
T = 123 K
0.49 × 0.17 × 0.14 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, England.]$ ) T_min = 0.901, T_max = 0.970
20727 measured reflections
10522 independent reflections
7301 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.074
wR(F²) = 0.190
S = 1.08
10522 reflections
272 parameters
H-atom parameters constrained
Δρ_max = 0.67 e Å⁻³
Δρ_min = −0.58 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C16–C21 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O4ⁱ	1.00	2.45	3.287 (2)	141
C3—H3A⋯O1ⁱⁱ	1.00	2.29	3.2439 (17)	159
C20—H20A⋯O1ⁱⁱⁱ	0.95	2.50	3.3086 (18)	144
C21—H21A⋯O1	0.95	2.52	3.1397 (18)	123
C6—H6A⋯Cg4^iv	0.95	2.71	3.4145 (17)	131
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) x-1, y, z; (iii) -x+2, -y+1, -z+1; (iv) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
The dihedral angles between the mean planes of the rings in the title molecule (°)

	Ring 2	Ring 3	Ring 4
Ring 1	53.07 (9)	73.19 (9)	6.61 (9)
Ring 2		64.42 (7)	46.85 (7)
Ring 3			79.45 (7)
Ring 1 is the N1/C1–C3 β-lactam ring, ring 2 is the C4–C9 benzene ring, ring 3 is the C10–C15 benzene ring and ring 4 is C16–C21 benzene ring.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); 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 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811013018/su2266sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811013018/su2266Isup2.hkl

checkCIF report

Comment top

The β-lactam antibiotics consists of a strained, four-membered, heterocyclic ring, known as the β-lactam ring (Garud et al., 2009). The most literal definition of a β-lactam antibiotics are the monocyclic β-lactams that do not contain another ring fused to the β-lactam one (Jarrahpour & Zarei, 2006). The discovery of the monocyclic β-lactams suggesting that the biological activity of β-lactams was strictly correlated to the presence of a suitably functionalized β-lactam ring (Jarrahpour & Zarei, 2010; Banik et al., 2004). The β-lactam ring systems show many interesting biological properties, such as cholesterol absorption inhibitors, human cytomegalovirus (HCMV) protease inhibitors, thrombin inhibitors, antihyperglycemic, anti-tumour, anti-HIV, human leukocyte elastase (HLE), potential antimalarials, anti-influenza virus, and serine-dependent enzyme inhibitors (Jarrahpor & Khalili, 2007).

As an extension of our work (Baktır et al., 2009; Çelik et al., 2009; Yalçın et al., 2009; Akkurt et al., 2008a,b; Akkurt et al., 2011a,b) on structural characterization of the β-lactam compounds, we herein report on the X-ray crystal structure of the title compound.

In the title molecule, Fig. 1, the β-lactam ring (N1/C1–C3) is nearly planar, with maximum deviations of -0.016 (1) for N1 and 0.015 (1) Å for C1. The C1—N1—C16—C17, N1–C3—C10—C11, O1—C1—C2—O2, C3—C2—O2—C4 and C2—O2—C4—C5 torsion angles are -172.79 (14), -159.77 (12), -60.7 (2), 92.79 (14) and -168.40 (12) °, respectively. The dihedral angles between the ring planes are listed in Table 2.

In the crystal molecules are linked by intermolecular C—H···O hydrogen-bond interactions and a weak C—H···π interaction (Table 1 and Fig. 2). Furthermore, there is a π-π stacking interaction [Cg4···Cg4ⁱ = 3.6513 (8) Å, where Cg4 is a centroid of the C16–C21 benzene ring; symmetry code: (i) = 1 - x, 1 - y, 1 - z] between the benzene rings attached to the methoxy group of molecules related by an inversion center.

Related literature top

For general background to β-lactams, see: Banik et al. (2004); Garud et al. (2009); Jarrahpor & Khalili (2007); Jarrahpour & Zarei (2006, 2010). For some of our previous reports of the structures of β-lactams, see: Akkurt et al. (2008a,b, 2011a,b); Baktır et al. (2009); Yalçın et al. (2009); Çelik et al. (2009).

Experimental top

A solution of N-(4-nitrobenzylidene)-4-methoxybenzenamine (1.00 mmol) was stirred with 4-chlorophenoxy acetic acid (1.50 mmol), p-toluenesulfonyl chloride (1.50 mmol) and triethylamine (2.5 mmol) in dry CH₂Cl₂ at room temperature over night. Then it was washed with HCl 1 N (20 ml), saturated NaHCO₃ (20 ml), brine (20 ml), dried over Na₂SO₄ and the solvent was evaporated under reduced pressure to give the crude product which was then purified by column chromatography over silica gel (7:3 hexane-EtOAc). (Yield 78%; mp: 415–417 K). Elemental analysis: Calc. for C₂₂H₁₇ClN₂O₅: C, 62.20; H, 4.03; N, 6.59%; Found: C, 62.15; H, 4.07; N, 6.65%.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound showing the atom labeling scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. The crystal packing and C-H···O hydrogen-bond interactions (dashed lines) of the title compound viewed down the a axis.

3-(4-Chlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitrophenyl)azetidin-2-one top

Crystal data top

C₂₂H₁₇ClN₂O₅	F(000) = 880
M_r = 424.83	D_x = 1.339 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6350 reflections
a = 6.0863 (2) Å	θ = 5.1–37.5°
b = 20.0855 (7) Å	µ = 0.22 mm⁻¹
c = 17.3819 (7) Å	T = 123 K
β = 97.419 (4)°	Needle, colourless
V = 2107.09 (13) Å³	0.49 × 0.17 × 0.14 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	10522 independent reflections
Radiation source: Enhance (Mo) X-ray Source	7301 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
Detector resolution: 10.5081 pixels mm^-1	θ_max = 37.6°, θ_min = 5.2°
ω scans	h = −10→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −34→29
T_min = 0.901, T_max = 0.970	l = −29→27
20727 measured 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)] = 0.074	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.190	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0816P)² + 0.3529P] where P = (F_o² + 2F_c²)/3
10522 reflections	(Δ/σ)_max = 0.001
272 parameters	Δρ_max = 0.67 e Å⁻³
0 restraints	Δρ_min = −0.58 e Å⁻³

Crystal data top

C₂₂H₁₇ClN₂O₅	V = 2107.09 (13) Å³
M_r = 424.83	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.0863 (2) Å	µ = 0.22 mm⁻¹
b = 20.0855 (7) Å	T = 123 K
c = 17.3819 (7) Å	0.49 × 0.17 × 0.14 mm
β = 97.419 (4)°

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	10522 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	7301 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.970	R_int = 0.041
20727 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.074	0 restraints
wR(F²) = 0.190	H-atom parameters constrained
S = 1.08	Δρ_max = 0.67 e Å⁻³
10522 reflections	Δρ_min = −0.58 e Å⁻³
272 parameters

Special details top

Experimental. Spectroscopic data for the title c ompound: IR (KBr, cm^-1): 1744.5 (CO, β-lactam). ¹H-NMR (250 MHz, CDCl₃) δ (p.p.m.): 3.67 (OMe, s, 3H), 5.88 (H-4, d, 1H, J = 5.0), 5.95 (H-3, d, 1H, J = 5.0), 6.78–8.14 (aromatic protons as a doublet at 6.80, a doublet at 6.90, a doublet at 7.15, a doublet at 7.23, a doublet at 7.61, a doublet at 8.12, 12H). ¹³C-NMR (62.9 MHz, CDCl₃) δ (p.p.m.): 55.6 (OMe), 60.3 (C-4), 81.3 (C-3), 115.1–156.6 (aromatic carbons), 161.8 (CO, β-lactam).

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
Cl1	0.37871 (8)	1.01738 (2)	0.70470 (3)	0.0430 (1)
O1	0.95577 (17)	0.64289 (6)	0.55371 (7)	0.0251 (3)
O2	0.74828 (16)	0.75343 (5)	0.65041 (6)	0.0193 (2)
O3	0.5101 (3)	0.65839 (9)	0.99331 (8)	0.0549 (6)
O4	0.1603 (3)	0.67723 (9)	0.95892 (8)	0.0507 (5)
O5	0.54345 (18)	0.33051 (5)	0.59384 (7)	0.0258 (3)
N1	0.62898 (18)	0.60647 (6)	0.60078 (7)	0.0175 (3)
N2	0.3499 (3)	0.66717 (8)	0.94411 (8)	0.0341 (4)
C1	0.7794 (2)	0.65032 (7)	0.57845 (8)	0.0184 (3)
C2	0.6374 (2)	0.71011 (7)	0.59484 (8)	0.0176 (3)
C3	0.4744 (2)	0.65738 (7)	0.62320 (8)	0.0170 (3)
C4	0.6499 (2)	0.81410 (7)	0.66070 (8)	0.0175 (3)
C5	0.7820 (2)	0.86043 (7)	0.70490 (8)	0.0222 (3)
C6	0.6991 (3)	0.92302 (8)	0.71847 (9)	0.0258 (4)
C7	0.4823 (3)	0.93834 (8)	0.68819 (10)	0.0266 (4)
C8	0.3492 (2)	0.89266 (8)	0.64457 (10)	0.0263 (4)
C9	0.4332 (2)	0.82983 (7)	0.63096 (9)	0.0224 (3)
C10	0.4462 (2)	0.65906 (7)	0.70792 (7)	0.0165 (3)
C11	0.2574 (2)	0.68941 (7)	0.72993 (8)	0.0202 (3)
C12	0.2254 (2)	0.69232 (8)	0.80772 (8)	0.0229 (4)
C13	0.3852 (3)	0.66479 (7)	0.86185 (8)	0.0223 (3)
C14	0.5750 (3)	0.63433 (8)	0.84242 (8)	0.0232 (3)
C15	0.6038 (2)	0.63173 (7)	0.76442 (8)	0.0202 (3)
C16	0.6116 (2)	0.53648 (7)	0.59893 (7)	0.0166 (3)
C17	0.4208 (2)	0.50585 (7)	0.61868 (8)	0.0196 (3)
C18	0.4028 (2)	0.43687 (7)	0.61633 (8)	0.0207 (3)
C19	0.5751 (2)	0.39828 (7)	0.59468 (8)	0.0193 (3)
C20	0.7656 (2)	0.42899 (7)	0.57502 (8)	0.0203 (3)
C21	0.7837 (2)	0.49782 (7)	0.57686 (8)	0.0194 (3)
C22	0.7363 (3)	0.29027 (8)	0.59211 (10)	0.0280 (4)
H2A	0.57270	0.73370	0.54650	0.0210*
H3A	0.32890	0.65630	0.58920	0.0200*
H5A	0.92920	0.84910	0.72580	0.0270*
H6A	0.78900	0.95500	0.74800	0.0310*
H8A	0.20170	0.90400	0.62410	0.0320*
H9A	0.34280	0.79790	0.60150	0.0270*
H11A	0.15010	0.70820	0.69150	0.0240*
H12A	0.09710	0.71270	0.82310	0.0270*
H14A	0.68190	0.61580	0.88120	0.0280*
H15A	0.73230	0.61110	0.74950	0.0240*
H17A	0.30350	0.53210	0.63370	0.0230*
H18A	0.27280	0.41600	0.62950	0.0250*
H20A	0.88320	0.40270	0.56030	0.0240*
H21A	0.91320	0.51870	0.56310	0.0230*
H22A	0.69550	0.24320	0.59390	0.0420*
H22B	0.84530	0.30090	0.63700	0.0420*
H22C	0.80030	0.29910	0.54420	0.0420*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0412 (2)	0.0256 (2)	0.0610 (3)	0.0126 (2)	0.0016 (2)	−0.0114 (2)
O1	0.0172 (4)	0.0272 (5)	0.0331 (5)	−0.0022 (4)	0.0115 (4)	−0.0070 (4)
O2	0.0166 (4)	0.0173 (4)	0.0233 (4)	0.0020 (3)	0.0005 (3)	−0.0029 (3)
O3	0.0564 (9)	0.0853 (13)	0.0211 (6)	−0.0004 (9)	−0.0024 (6)	−0.0015 (7)
O4	0.0568 (9)	0.0691 (11)	0.0309 (7)	0.0223 (8)	0.0234 (6)	0.0011 (6)
O5	0.0219 (5)	0.0174 (5)	0.0383 (6)	0.0011 (4)	0.0049 (4)	−0.0006 (4)
N1	0.0132 (4)	0.0185 (5)	0.0218 (5)	0.0004 (4)	0.0063 (4)	−0.0034 (4)
N2	0.0454 (8)	0.0378 (8)	0.0200 (6)	0.0035 (7)	0.0076 (6)	−0.0022 (5)
C1	0.0154 (5)	0.0212 (6)	0.0191 (5)	−0.0009 (4)	0.0039 (4)	−0.0037 (4)
C2	0.0159 (5)	0.0188 (5)	0.0184 (5)	0.0001 (4)	0.0029 (4)	−0.0021 (4)
C3	0.0125 (4)	0.0196 (6)	0.0190 (5)	0.0020 (4)	0.0027 (4)	−0.0026 (4)
C4	0.0168 (5)	0.0166 (5)	0.0193 (5)	0.0010 (4)	0.0027 (4)	−0.0002 (4)
C5	0.0217 (6)	0.0207 (6)	0.0230 (6)	0.0017 (5)	−0.0015 (5)	−0.0030 (5)
C6	0.0273 (6)	0.0210 (6)	0.0277 (7)	0.0020 (6)	−0.0020 (5)	−0.0049 (5)
C7	0.0288 (7)	0.0198 (6)	0.0312 (7)	0.0055 (6)	0.0034 (6)	−0.0038 (5)
C8	0.0194 (6)	0.0236 (7)	0.0352 (8)	0.0047 (5)	0.0008 (5)	−0.0014 (6)
C9	0.0165 (5)	0.0206 (6)	0.0294 (7)	0.0008 (5)	0.0006 (5)	−0.0025 (5)
C10	0.0136 (4)	0.0170 (5)	0.0190 (5)	−0.0001 (4)	0.0030 (4)	−0.0021 (4)
C11	0.0163 (5)	0.0228 (6)	0.0221 (6)	0.0035 (5)	0.0045 (4)	−0.0009 (5)
C12	0.0224 (6)	0.0261 (7)	0.0216 (6)	0.0028 (5)	0.0080 (5)	−0.0027 (5)
C13	0.0277 (6)	0.0219 (6)	0.0180 (5)	−0.0021 (5)	0.0059 (5)	−0.0033 (5)
C14	0.0245 (6)	0.0235 (6)	0.0208 (6)	0.0003 (5)	−0.0002 (5)	0.0006 (5)
C15	0.0168 (5)	0.0216 (6)	0.0219 (6)	0.0026 (5)	0.0016 (4)	−0.0008 (5)
C16	0.0139 (4)	0.0176 (5)	0.0185 (5)	0.0003 (4)	0.0028 (4)	−0.0032 (4)
C17	0.0134 (4)	0.0201 (6)	0.0257 (6)	0.0011 (4)	0.0046 (4)	−0.0020 (5)
C18	0.0147 (5)	0.0216 (6)	0.0260 (6)	−0.0010 (5)	0.0035 (4)	0.0006 (5)
C19	0.0178 (5)	0.0190 (6)	0.0208 (6)	−0.0002 (5)	0.0013 (4)	−0.0014 (4)
C20	0.0175 (5)	0.0210 (6)	0.0233 (6)	0.0027 (5)	0.0056 (4)	−0.0029 (5)
C21	0.0157 (5)	0.0204 (6)	0.0231 (6)	0.0004 (5)	0.0063 (4)	−0.0028 (5)
C22	0.0270 (7)	0.0204 (6)	0.0372 (8)	0.0041 (6)	0.0069 (6)	0.0013 (6)

Geometric parameters (Å, º) top

Cl1—C7	1.7456 (17)	C13—C14	1.387 (2)
O1—C1	1.2160 (16)	C14—C15	1.390 (2)
O2—C2	1.4061 (17)	C16—C17	1.3957 (18)
O2—C4	1.3795 (17)	C16—C21	1.3968 (18)
O3—N2	1.224 (2)	C17—C18	1.390 (2)
O4—N2	1.231 (3)	C18—C19	1.3943 (18)
O5—C19	1.3746 (17)	C19—C20	1.3942 (18)
O5—C22	1.429 (2)	C20—C21	1.387 (2)
N1—C1	1.3625 (18)	C2—H2A	1.0000
N1—C3	1.4756 (18)	C3—H3A	1.0000
N1—C16	1.4098 (19)	C5—H5A	0.9500
N2—C13	1.474 (2)	C6—H6A	0.9500
C1—C2	1.5277 (19)	C8—H8A	0.9500
C2—C3	1.5733 (19)	C9—H9A	0.9500
C3—C10	1.5048 (18)	C11—H11A	0.9500
C4—C5	1.3940 (19)	C12—H12A	0.9500
C4—C9	1.3894 (18)	C14—H14A	0.9500
C5—C6	1.386 (2)	C15—H15A	0.9500
C6—C7	1.391 (3)	C17—H17A	0.9500
C7—C8	1.384 (2)	C18—H18A	0.9500
C8—C9	1.393 (2)	C20—H20A	0.9500
C10—C11	1.3971 (18)	C21—H21A	0.9500
C10—C15	1.3938 (18)	C22—H22A	0.9800
C11—C12	1.3920 (19)	C22—H22B	0.9800
C12—C13	1.379 (2)	C22—H22C	0.9800

C2—O2—C4	117.25 (10)	O5—C19—C18	116.37 (12)
C19—O5—C22	116.49 (11)	O5—C19—C20	123.73 (12)
C1—N1—C3	95.86 (11)	C18—C19—C20	119.90 (13)
C1—N1—C16	133.57 (12)	C19—C20—C21	120.10 (12)
C3—N1—C16	130.43 (11)	C16—C21—C20	120.02 (12)
O3—N2—O4	124.14 (15)	O2—C2—H2A	113.00
O3—N2—C13	118.06 (17)	C1—C2—H2A	113.00
O4—N2—C13	117.79 (15)	C3—C2—H2A	113.00
O1—C1—N1	132.67 (14)	N1—C3—H3A	112.00
O1—C1—C2	135.15 (13)	C2—C3—H3A	112.00
N1—C1—C2	92.17 (10)	C10—C3—H3A	112.00
O2—C2—C1	112.44 (10)	C4—C5—H5A	120.00
O2—C2—C3	117.87 (11)	C6—C5—H5A	120.00
C1—C2—C3	85.64 (10)	C5—C6—H6A	121.00
N1—C3—C2	86.24 (9)	C7—C6—H6A	120.00
N1—C3—C10	115.54 (11)	C7—C8—H8A	120.00
C2—C3—C10	116.60 (11)	C9—C8—H8A	120.00
O2—C4—C5	115.60 (11)	C4—C9—H9A	120.00
O2—C4—C9	124.03 (12)	C8—C9—H9A	120.00
C5—C4—C9	120.36 (13)	C10—C11—H11A	120.00
C4—C5—C6	120.17 (13)	C12—C11—H11A	120.00
C5—C6—C7	119.00 (15)	C11—C12—H12A	121.00
Cl1—C7—C6	118.97 (13)	C13—C12—H12A	121.00
Cl1—C7—C8	119.66 (13)	C13—C14—H14A	121.00
C6—C7—C8	121.37 (15)	C15—C14—H14A	121.00
C7—C8—C9	119.47 (13)	C10—C15—H15A	120.00
C4—C9—C8	119.62 (13)	C14—C15—H15A	120.00
C3—C10—C11	118.66 (11)	C16—C17—H17A	120.00
C3—C10—C15	121.71 (11)	C18—C17—H17A	120.00
C11—C10—C15	119.63 (12)	C17—C18—H18A	120.00
C10—C11—C12	120.50 (12)	C19—C18—H18A	120.00
C11—C12—C13	118.11 (13)	C19—C20—H20A	120.00
N2—C13—C12	118.08 (15)	C21—C20—H20A	120.00
N2—C13—C14	118.74 (14)	C16—C21—H21A	120.00
C12—C13—C14	123.17 (13)	C20—C21—H21A	120.00
C13—C14—C15	117.90 (14)	O5—C22—H22A	109.00
C10—C15—C14	120.69 (13)	O5—C22—H22B	109.00
N1—C16—C17	119.76 (12)	O5—C22—H22C	109.00
N1—C16—C21	120.26 (11)	H22A—C22—H22B	109.00
C17—C16—C21	119.99 (13)	H22A—C22—H22C	109.00
C16—C17—C18	119.81 (12)	H22B—C22—H22C	110.00
C17—C18—C19	120.19 (12)

C4—O2—C2—C1	170.01 (11)	C2—C3—C10—C11	101.14 (14)
C4—O2—C2—C3	−92.79 (14)	C2—C3—C10—C15	−78.33 (17)
C2—O2—C4—C5	−168.40 (12)	O2—C4—C5—C6	179.78 (13)
C2—O2—C4—C9	12.45 (19)	C9—C4—C5—C6	−1.0 (2)
C22—O5—C19—C18	−163.97 (13)	O2—C4—C9—C8	−179.94 (13)
C22—O5—C19—C20	16.4 (2)	C5—C4—C9—C8	1.0 (2)
C3—N1—C1—O1	178.91 (16)	C4—C5—C6—C7	0.8 (2)
C3—N1—C1—C2	−2.36 (11)	C5—C6—C7—Cl1	−179.53 (12)
C16—N1—C1—O1	−5.2 (3)	C5—C6—C7—C8	−0.5 (2)
C16—N1—C1—C2	173.55 (14)	Cl1—C7—C8—C9	179.44 (12)
C1—N1—C3—C2	2.30 (11)	C6—C7—C8—C9	0.4 (3)
C1—N1—C3—C10	−115.47 (12)	C7—C8—C9—C4	−0.6 (2)
C16—N1—C3—C2	−173.81 (13)	C3—C10—C11—C12	−179.70 (13)
C16—N1—C3—C10	68.42 (18)	C15—C10—C11—C12	−0.2 (2)
C1—N1—C16—C17	−172.79 (14)	C3—C10—C15—C14	179.50 (13)
C1—N1—C16—C21	6.7 (2)	C11—C10—C15—C14	0.0 (2)
C3—N1—C16—C17	1.9 (2)	C10—C11—C12—C13	0.3 (2)
C3—N1—C16—C21	−178.63 (13)	C11—C12—C13—N2	−179.27 (14)
O3—N2—C13—C12	−162.24 (17)	C11—C12—C13—C14	−0.2 (2)
O3—N2—C13—C14	18.6 (2)	N2—C13—C14—C15	179.09 (14)
O4—N2—C13—C12	18.5 (2)	C12—C13—C14—C15	0.0 (2)
O4—N2—C13—C14	−160.65 (17)	C13—C14—C15—C10	0.1 (2)
O1—C1—C2—O2	−60.7 (2)	N1—C16—C17—C18	179.53 (12)
O1—C1—C2—C3	−179.12 (17)	C21—C16—C17—C18	0.0 (2)
N1—C1—C2—O2	120.62 (12)	N1—C16—C21—C20	−179.90 (12)
N1—C1—C2—C3	2.21 (10)	C17—C16—C21—C20	−0.4 (2)
O2—C2—C3—N1	−115.16 (12)	C16—C17—C18—C19	0.3 (2)
O2—C2—C3—C10	1.60 (17)	C17—C18—C19—O5	−179.93 (13)
C1—C2—C3—N1	−2.04 (9)	C17—C18—C19—C20	−0.3 (2)
C1—C2—C3—C10	114.72 (12)	O5—C19—C20—C21	179.54 (13)
N1—C3—C10—C11	−159.77 (12)	C18—C19—C20—C21	−0.1 (2)
N1—C3—C10—C15	20.76 (18)	C19—C20—C21—C16	0.4 (2)

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C16–C21 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	1.00	2.45	3.287 (2)	141
C3—H3A···O1ⁱⁱ	1.00	2.29	3.2439 (17)	159
C15—H15A···N1	0.95	2.58	2.9127 (18)	101
C20—H20A···O1ⁱⁱⁱ	0.95	2.50	3.3086 (18)	144
C21—H21A···O1	0.95	2.52	3.1397 (18)	123
C6—H6A···Cg4^iv	0.95	2.71	3.4145 (17)	131

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

Experimental details

Crystal data
Chemical formula	C₂₂H₁₇ClN₂O₅
M_r	424.83
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	123
a, b, c (Å)	6.0863 (2), 20.0855 (7), 17.3819 (7)
β (°)	97.419 (4)
V (Å³)	2107.09 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.49 × 0.17 × 0.14

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.901, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	20727, 10522, 7301
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.858

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.074, 0.190, 1.08
No. of reflections	10522
No. of parameters	272
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.67, −0.58

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg4 is the centroid of the C16–C21 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O4ⁱ	1.00	2.45	3.287 (2)	141
C3—H3A···O1ⁱⁱ	1.00	2.29	3.2439 (17)	159
C20—H20A···O1ⁱⁱⁱ	0.95	2.50	3.3086 (18)	144
C21—H21A···O1	0.95	2.52	3.1397 (18)	123
C6—H6A···Cg4^iv	0.95	2.71	3.4145 (17)	131

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

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

	Ring 2	Ring 3	Ring 4
Ring 1	53.07 (9)	73.19 (9)	6.61 (9)
Ring 2		64.42 (7)	46.85 (7)
Ring 3			79.45 (7)

Ring 1 is the N1/C1–C3 β-lactam ring, ring 2 is the C4–C9 benzene ring, ring 3 is the C10–C15 benzene ring and ring 4 is C16–C21 benzene ring.

Acknowledgements

AJ and SATB thank the Shiraz University Research Council for financial support (grant No. 89-GR–SC-23).

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
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Volume 67| Part 5| May 2011| Pages o1101-o1102

doi:10.1107/S1600536811013018

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

3-(4-Chloro­phen­­oxy)-1-(4-meth­­oxy­phen­yl)-4-(4-nitro­phen­yl)azetidin-2-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(4-Chlorophenoxy)-1-(4-methoxyphenyl)-4-(4-nitrophenyl)azetidin-2-one