3-(4-Chloro-phen-oxy)-1-(4-meth-oxy-phen-yl)-4-(4-nitro-phen-yl)azetidin-2-one.

In the title compound, C(22)H(17)ClN(2)O(5), 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 meth-oxy-benzene rings, respectively. The crystal structure is stabilized by C-H⋯O hydrogen bonds, a weak C-H⋯π inter-action and a π-π stacking inter-action [centroid-centroid distance = 3.6513 (8) Å] between the meth-oxy-benzene rings of inversion-related mol-ecules.

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 = 424.83

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.074

wR(F 2) = 0.190

S = 1.08

10522 reflections

272 parameters

H-atom parameters constrained

Δρmax = 0.67 e Å−3

Δρmin = −0.58 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; 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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H17ClN2O5	F(000) = 880
Mr = 424.83	Dx = 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

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	10522 independent reflections
Radiation source: Enhance (Mo) X-ray Source	7301 reflections with I > 2σ(I)
graphite	Rint = 0.041
Detector resolution: 10.5081 pixels mm-1	θmax = 37.6°, θmin = 5.2°
ω scans	h = −10→6
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −34→29
Tmin = 0.901, Tmax = 0.970	l = −29→27
20727 measured reflections

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(Fo2) + (0.0816P)2 + 0.3529P] where P = (Fo2 + 2Fc2)/3
10522 reflections	(Δ/σ)max = 0.001
272 parameters	Δρmax = 0.67 e Å−3
0 restraints	Δρmin = −0.58 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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···Cg4iv	0.95	2.71	3.4145 (17)	131

	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)

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⋯Cg4iv	0.95	2.71	3.4145 (17)	131

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

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.