3-(2,4-Di­chloro­phen­oxy)-1-(4-meth­oxy­benz­yl)-4-(4-nitro­phen­yl)azetidin-2-one

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

doi:10.1107/S1600536814015013

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 8| August 2014| Pages o835-o836

doi:10.1107/S1600536814015013

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3-(2,4-Dichlorophenoxy)-1-(4-methoxybenzyl)-4-(4-nitrophenyl)azetidin-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 24 June 2014; accepted 25 June 2014; online 2 July 2014)

The β-lactam ring of the title compound, C₂₃H₁₈Cl₂N₂O₅, is nearly planar [maximum deviation = 0.019 (2) Å for the N atom] and its mean plane makes dihedral angles of 56.86 (15), 68.83 (15) and 83.75 (15)° with the dichloro-, nitro- and methoxy-substituted benzene rings, respectively. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds, forming inversion dimers with R₂²(10) loops. The dimers are linked by further C—H⋯O hydrogen bonds, forming sheets lying parallel to (001). The molecular packing is further stabilized by C—H⋯π interactions.

Keywords: crystal structure.

CCDC reference: 1010327

Related literature

For general background to β-lactams, see: Schunk & Enders (2000 ); France et al. (2004 ); Pitts & Lectka (2014 ); Arya et al. (2014 ); Banik et al. (2003 ); Delpiccolo et al. (2003 ); Hodous & Fu (2002 ). For the crystal structures of some β-lactams, see: Akkurt et al. (2011 ); Butcher et al. (2011 ).

Experimental

Crystal data

C₂₃H₁₈Cl₂N₂O₅
M_r = 473.29
Monoclinic, P 2₁ /n
a = 5.0716 (5) Å
b = 20.9390 (12) Å
c = 20.1516 (18) Å
β = 96.457 (7)°
V = 2126.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.35 mm⁻¹
T = 296 K
0.59 × 0.28 × 0.06 mm

Data collection

Stoe IPDS 2 diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ) T_min = 0.901, T_max = 0.972
15060 measured reflections
4179 independent reflections
2123 reflections with I > 2σ(I)
R_int = 0.062

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.061
S = 0.85
4179 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O1ⁱ	0.98	2.58	3.417 (3)	143
C6—H6⋯O5ⁱⁱ	0.93	2.57	3.328 (3)	139
C12—H12⋯O3ⁱⁱⁱ	0.93	2.57	3.495 (4)	176
C16—H16A⋯Cg^iv	0.97	2.70	3.649 (3)	166
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z; (iii) -x-1, -y+1, -z; (iv) x+1, y, z.

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: 1010327

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814015013/su2747sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015013/su2747Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814015013/su2747Isup3.cml

checkCIF report

Comment top

The β-lactam (2-azetidinone) ring is the most well known heterocycle to have been studied during the last century (Pitts & Lectka, 2014; France et al., 2004; Arya et al., 2014). The β-lactam framework is the structural element of a large class of broad-spectrum antibiotics such as penicillins, cephalosporins and monobactams (Delpiccolo et al., 2003; Schunk & Enders, 2000; Banik et al., 2003), that effectively combat bacterial infections (Schunk & Enders, 2000). However, the need for new antibiotics has been growing, as a result of the rapid emergence of bacterial strains' resistance to traditional drugs (Hodous & Fu, 2002; Delpiccolo et al., 2003). Therefore, in continuation of our research on the synthesis of β-lactams, we describe herein the synthesis and crystal structure of the title compound.

In the title molecule, Fig. 1, the β-lactam ring (N1/C1–C3) is nearly planar with a maximum deviation of -0.016 (1) Å for atom N1. The mean plane of this four-membered β-lactam ring is twisted from the planes of the dichloro-, nitro- and methoxy substituted benzene rings, making the dihedral angles of 56.86 (15), 68.83 (15) and 83.75 (15)°, respectively. The bond lengths and bond angles are within normal values and are comparable with those reported for similar compounds (Akkurt et al., 2011; Butcher et al., 2011).

In the crystal, molecules are linked by a pair of C—H···O hydrogen bonds forming inversion dimers with R²₂(10) loops (Table 1 and Fig. 2). The dimers are linked by further C-H···O hydrogen bonds forming sheets lying parallel to (001). The molecular packing is further stabilized by C—H···π interactions (Table 1).

Related literature top

For general background to β-lactams, see: Schunk & Enders (2000); France et al. (2004); Pitts & Lectka (2014); Arya et al. (2014); Banik et al. (2003); Delpiccolo et al. (2003); Hodous & Fu (2002). For the crystal structures of some β-lactams, see: Akkurt et al. (2011); Butcher et al. (2011).

Experimental top

A mixture of N-(4-nitrobenzylidene) (4-methoxyphenyl) methanamine (0.27 g, 1.00 mmol), 2,4-dichlorophenoxyacetic acid (0.34 g, 1.50 mmol), tosyl chloride (0.28 g, 1.50 mmol) and triethylamine (0.25 g, 2.50 mmol) in dry CH₂Cl₂ was stirred at room temperature overnight. After completion of the reaction, monitored by TLC, the mixture was washed with HCl (1 N), saturated sodium bicarbonate solution, brine, dried over anhydrous Na₂SO₄ and the solvent was then evaporated under vacuum to afford the crude product. This was purified by recrystallization from EtOAc giving pale yellow prismatic crystals on slow evaporation of the solvent (yield 72%). M.p. 397 - 399 K. Spectroscopic data for the title compound are given in the archived CIF.

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 the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view along the a axis of the crystal packing of the title compound. Hydrogen bonds are shown as dashed lines (see Table 1 for details).

3-(2,4-Dichlorophenoxy)-1-(4-methoxybenzyl)-4-(4-nitrophenyl)azetidin-2-one top

Crystal data top

C₂₃H₁₈Cl₂N₂O₅	F(000) = 976
M_r = 473.29	D_x = 1.478 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 10788 reflections
a = 5.0716 (5) Å	θ = 1.4–28.4°
b = 20.9390 (12) Å	µ = 0.35 mm⁻¹
c = 20.1516 (18) Å	T = 296 K
β = 96.457 (7)°	Prism, pale yellow
V = 2126.4 (3) Å³	0.59 × 0.28 × 0.06 mm
Z = 4

Data collection top

Stoe IPDS 2 diffractometer	4179 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2123 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.062
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.0°, θ_min = 1.4°
ω scans	h = −6→6
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −25→25
T_min = 0.901, T_max = 0.972	l = −24→24
15060 measured reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.042	H-atom parameters constrained
wR(F²) = 0.061	w = 1/[σ²(F_o²) + (0.0162P)²] where P = (F_o² + 2F_c²)/3
S = 0.85	(Δ/σ)_max < 0.001
4179 reflections	Δρ_max = 0.16 e Å⁻³
289 parameters	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₃H₁₈Cl₂N₂O₅	V = 2126.4 (3) Å³
M_r = 473.29	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.0716 (5) Å	µ = 0.35 mm⁻¹
b = 20.9390 (12) Å	T = 296 K
c = 20.1516 (18) Å	0.59 × 0.28 × 0.06 mm
β = 96.457 (7)°

Data collection top

Stoe IPDS 2 diffractometer	4179 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	2123 reflections with I > 2σ(I)
T_min = 0.901, T_max = 0.972	R_int = 0.062
15060 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.061	H-atom parameters constrained
S = 0.85	Δρ_max = 0.16 e Å⁻³
4179 reflections	Δρ_min = −0.19 e Å⁻³
289 parameters

Special details top

Experimental. Spectroscopic data for the title compound:

IR (KBr, cm^-1): 1758 (CO β-lactam), 1352, 1520 (NO₂). ¹H-NMR (CDCl₃) δ (p.p.m.): 3.78 (OMe, s, 3H), 3.94 (CH₂, d, J =14.6 Hz, 1H), 4.78 (CH₂, d, J = 14.6 Hz, 1H), 4.85 (H-4, d, J = 4.8 Hz, 1H), 5.38 (H-3, d, J = 4.8 Hz, 1H), 6.80 (ArH, d, J = 8.7 Hz, 2H), 7.00 (ArH, d, J = 8.8 Hz, 1H), 7.03 (ArH, d, J = 8.7 Hz, 2H), 7.08 (ArH, d, J = 8.8 Hz, 1H), 7.19 (ArH, s, 1H), 7.45 (ArH, d, J = 8.8 Hz, 2H), 8.17 (ArH, d, J = 8.8 Hz, 2H). ¹³C-NMR (CDCl₃) δ (p.p.m.): 44.4 (CH₂), 55.3 (OMe) 59.8 (C-4), 82.5 (C-3), 114.3, 116.2, 123.4, 123.8, 125.8, 127.5, 127.7, 129.4, 130.0, 130.1, 140.3, 148.1, 151.1, 159.5 (aromatic carbon), 164.36 (CO β-lactam). MS m/z = 472 [M⁺].

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	0.91503 (14)	0.22124 (4)	0.29769 (3)	0.0722 (3)
Cl2	0.23669 (16)	0.35928 (3)	0.13099 (3)	0.0705 (3)
O1	0.2489 (4)	0.10566 (8)	0.01887 (8)	0.0716 (7)
O2	0.0396 (3)	0.23885 (7)	0.08223 (8)	0.0598 (6)
O3	−0.2578 (5)	0.50783 (10)	−0.05297 (12)	0.1058 (10)
O4	0.0490 (5)	0.48354 (10)	−0.11293 (12)	0.1037 (10)
O5	−0.9069 (4)	−0.04073 (8)	−0.20251 (9)	0.0712 (7)
N1	−0.0881 (4)	0.15859 (8)	−0.04739 (9)	0.0501 (7)
N2	−0.1189 (6)	0.46924 (12)	−0.07734 (13)	0.0730 (11)
C1	0.0631 (5)	0.14198 (12)	0.00884 (11)	0.0488 (9)
C2	−0.0932 (5)	0.18554 (11)	0.05155 (11)	0.0499 (9)
C3	−0.2519 (5)	0.20533 (11)	−0.01636 (11)	0.0493 (8)
C4	0.2330 (5)	0.23048 (11)	0.13478 (11)	0.0484 (9)
C5	0.3203 (5)	0.17250 (12)	0.16032 (11)	0.0560 (9)
C6	0.5282 (5)	0.16962 (12)	0.21112 (11)	0.0559 (10)
C7	0.6458 (5)	0.22470 (13)	0.23584 (11)	0.0518 (9)
C8	0.5564 (5)	0.28303 (12)	0.21190 (11)	0.0561 (9)
C9	0.3495 (5)	0.28593 (11)	0.16161 (10)	0.0493 (9)
C10	−0.2222 (4)	0.27389 (11)	−0.03557 (10)	0.0438 (8)
C11	−0.3762 (5)	0.31962 (12)	−0.00929 (12)	0.0576 (10)
C12	−0.3445 (6)	0.38355 (13)	−0.02211 (13)	0.0638 (11)
C13	−0.1588 (6)	0.40110 (12)	−0.06275 (12)	0.0536 (10)
C14	−0.0052 (5)	0.35691 (13)	−0.09064 (12)	0.0588 (10)
C15	−0.0372 (5)	0.29338 (12)	−0.07617 (11)	0.0547 (9)
C16	−0.0924 (5)	0.13434 (12)	−0.11484 (10)	0.0558 (9)
C17	−0.3177 (5)	0.08960 (11)	−0.13711 (11)	0.0465 (9)
C18	−0.4539 (5)	0.09594 (11)	−0.19956 (11)	0.0526 (9)
C19	−0.6509 (5)	0.05349 (12)	−0.22383 (11)	0.0540 (9)
C20	−0.7172 (5)	0.00404 (12)	−0.18411 (13)	0.0529 (9)
C21	−0.5827 (6)	−0.00258 (12)	−0.12111 (13)	0.0647 (10)
C22	−0.3856 (5)	0.03948 (12)	−0.09822 (12)	0.0614 (10)
C23	−1.0492 (6)	−0.03553 (13)	−0.26693 (14)	0.0812 (12)
H2	−0.20000	0.16210	0.08110	0.0600*
H3	−0.43840	0.19230	−0.01930	0.0590*
H5	0.23980	0.13510	0.14350	0.0670*
H6	0.58760	0.13030	0.22830	0.0670*
H8	0.63500	0.32040	0.22950	0.0670*
H11	−0.50410	0.30700	0.01770	0.0690*
H12	−0.44720	0.41410	−0.00350	0.0770*
H14	0.11830	0.36960	−0.11880	0.0710*
H15	0.06820	0.26310	−0.09420	0.0660*
H16A	0.07350	0.11230	−0.11850	0.0670*
H16B	−0.10090	0.17030	−0.14530	0.0670*
H18	−0.41260	0.12980	−0.22640	0.0630*
H19	−0.73760	0.05840	−0.26670	0.0650*
H21	−0.62600	−0.03590	−0.09380	0.0780*
H22	−0.29650	0.03400	−0.05570	0.0740*
H23A	−1.17560	−0.06970	−0.27350	0.1210*
H23B	−1.14060	0.00470	−0.27080	0.1210*
H23C	−0.92780	−0.03800	−0.30010	0.1210*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0632 (5)	0.0887 (5)	0.0622 (4)	−0.0012 (4)	−0.0041 (3)	0.0047 (4)
Cl2	0.1082 (6)	0.0417 (4)	0.0589 (4)	0.0053 (4)	−0.0028 (4)	−0.0010 (3)
O1	0.0839 (15)	0.0666 (12)	0.0620 (11)	0.0211 (12)	−0.0019 (10)	−0.0016 (10)
O2	0.0835 (13)	0.0417 (10)	0.0498 (10)	−0.0014 (9)	−0.0113 (9)	−0.0032 (8)
O3	0.136 (2)	0.0596 (14)	0.1232 (19)	0.0290 (15)	0.0202 (16)	0.0043 (13)
O4	0.138 (2)	0.0701 (15)	0.1078 (18)	−0.0071 (14)	0.0353 (16)	0.0130 (13)
O5	0.0738 (13)	0.0555 (11)	0.0812 (13)	−0.0087 (11)	−0.0044 (10)	−0.0089 (10)
N1	0.0607 (14)	0.0447 (12)	0.0437 (12)	0.0053 (11)	0.0008 (11)	−0.0081 (9)
N2	0.090 (2)	0.0609 (19)	0.0651 (17)	0.0106 (17)	−0.0044 (14)	0.0040 (14)
C1	0.0589 (19)	0.0406 (14)	0.0465 (15)	−0.0059 (14)	0.0046 (14)	0.0002 (13)
C2	0.0589 (17)	0.0437 (15)	0.0474 (14)	−0.0096 (13)	0.0075 (13)	−0.0017 (12)
C3	0.0402 (15)	0.0532 (15)	0.0548 (14)	−0.0045 (13)	0.0068 (12)	−0.0074 (13)
C4	0.0645 (17)	0.0472 (15)	0.0338 (12)	0.0010 (14)	0.0067 (12)	−0.0024 (12)
C5	0.0755 (19)	0.0424 (15)	0.0492 (15)	−0.0051 (15)	0.0025 (14)	−0.0012 (12)
C6	0.072 (2)	0.0489 (16)	0.0470 (15)	0.0060 (15)	0.0072 (14)	0.0036 (12)
C7	0.0547 (17)	0.0572 (17)	0.0439 (14)	−0.0010 (15)	0.0075 (12)	−0.0019 (13)
C8	0.0727 (18)	0.0465 (16)	0.0496 (15)	−0.0083 (15)	0.0087 (13)	−0.0078 (13)
C9	0.0691 (18)	0.0409 (15)	0.0381 (13)	−0.0018 (14)	0.0071 (13)	−0.0026 (11)
C10	0.0395 (14)	0.0495 (15)	0.0419 (13)	0.0010 (14)	0.0020 (11)	−0.0058 (12)
C11	0.0569 (18)	0.0614 (18)	0.0568 (15)	0.0101 (15)	0.0164 (13)	−0.0009 (14)
C12	0.068 (2)	0.0553 (18)	0.0683 (18)	0.0209 (15)	0.0080 (16)	−0.0036 (14)
C13	0.0605 (19)	0.0469 (17)	0.0505 (15)	0.0055 (15)	−0.0067 (14)	0.0030 (13)
C14	0.0599 (19)	0.0576 (17)	0.0602 (16)	0.0011 (16)	0.0123 (14)	0.0032 (14)
C15	0.0550 (17)	0.0492 (17)	0.0611 (15)	0.0059 (14)	0.0118 (14)	−0.0051 (13)
C16	0.0653 (18)	0.0551 (16)	0.0463 (14)	0.0029 (15)	0.0034 (12)	−0.0103 (13)
C17	0.0563 (17)	0.0410 (14)	0.0417 (14)	0.0041 (13)	0.0037 (12)	−0.0066 (12)
C18	0.0659 (18)	0.0450 (15)	0.0460 (15)	0.0013 (14)	0.0029 (13)	0.0012 (12)
C19	0.0637 (18)	0.0499 (16)	0.0455 (14)	0.0027 (14)	−0.0061 (13)	−0.0033 (13)
C20	0.0568 (17)	0.0396 (15)	0.0610 (17)	0.0043 (14)	0.0004 (14)	−0.0092 (13)
C21	0.087 (2)	0.0469 (15)	0.0570 (17)	−0.0076 (16)	−0.0059 (15)	0.0051 (13)
C22	0.082 (2)	0.0517 (16)	0.0470 (15)	0.0020 (16)	−0.0084 (14)	0.0000 (13)
C23	0.070 (2)	0.076 (2)	0.092 (2)	−0.0058 (17)	−0.0155 (17)	−0.0193 (17)

Geometric parameters (Å, º) top

Cl1—C7	1.744 (2)	C14—C15	1.375 (4)
Cl2—C9	1.729 (2)	C16—C17	1.506 (3)
O1—C1	1.210 (3)	C17—C18	1.372 (3)
O2—C2	1.410 (3)	C17—C22	1.377 (3)
O2—C4	1.371 (3)	C18—C19	1.385 (3)
O3—N2	1.212 (4)	C19—C20	1.374 (4)
O4—N2	1.211 (4)	C20—C21	1.379 (4)
O5—C20	1.364 (3)	C21—C22	1.373 (4)
O5—C23	1.417 (3)	C2—H2	0.9800
N1—C1	1.341 (3)	C3—H3	0.9800
N1—C3	1.468 (3)	C5—H5	0.9300
N1—C16	1.449 (3)	C6—H6	0.9300
N2—C13	1.475 (4)	C8—H8	0.9300
C1—C2	1.534 (3)	C11—H11	0.9300
C2—C3	1.564 (3)	C12—H12	0.9300
C3—C10	1.499 (3)	C14—H14	0.9300
C4—C5	1.372 (3)	C15—H15	0.9300
C4—C9	1.385 (3)	C16—H16A	0.9700
C5—C6	1.386 (3)	C16—H16B	0.9700
C6—C7	1.367 (4)	C18—H18	0.9300
C7—C8	1.371 (4)	C19—H19	0.9300
C8—C9	1.376 (3)	C21—H21	0.9300
C10—C11	1.379 (3)	C22—H22	0.9300
C10—C15	1.374 (3)	C23—H23A	0.9600
C11—C12	1.376 (4)	C23—H23B	0.9600
C12—C13	1.366 (4)	C23—H23C	0.9600
C13—C14	1.370 (4)

C2—O2—C4	120.15 (17)	O5—C20—C19	124.8 (2)
C20—O5—C23	117.9 (2)	O5—C20—C21	116.2 (2)
C1—N1—C3	96.33 (18)	C19—C20—C21	119.0 (2)
C1—N1—C16	130.5 (2)	C20—C21—C22	120.7 (2)
C3—N1—C16	133.13 (19)	C17—C22—C21	121.2 (2)
O3—N2—O4	123.7 (3)	O2—C2—H2	114.00
O3—N2—C13	117.7 (3)	C1—C2—H2	113.00
O4—N2—C13	118.6 (3)	C3—C2—H2	114.00
O1—C1—N1	131.7 (2)	N1—C3—H3	112.00
O1—C1—C2	136.2 (2)	C2—C3—H3	112.00
N1—C1—C2	92.14 (19)	C10—C3—H3	112.00
O2—C2—C1	117.7 (2)	C4—C5—H5	120.00
O2—C2—C3	110.33 (18)	C6—C5—H5	120.00
C1—C2—C3	85.08 (17)	C5—C6—H6	120.00
N1—C3—C2	86.32 (17)	C7—C6—H6	120.00
N1—C3—C10	116.77 (19)	C7—C8—H8	120.00
C2—C3—C10	115.03 (19)	C9—C8—H8	120.00
O2—C4—C5	125.1 (2)	C10—C11—H11	119.00
O2—C4—C9	115.5 (2)	C12—C11—H11	119.00
C5—C4—C9	119.3 (2)	C11—C12—H12	121.00
C4—C5—C6	120.1 (2)	C13—C12—H12	121.00
C5—C6—C7	119.8 (2)	C13—C14—H14	121.00
Cl1—C7—C6	120.0 (2)	C15—C14—H14	121.00
Cl1—C7—C8	119.3 (2)	C10—C15—H15	119.00
C6—C7—C8	120.7 (2)	C14—C15—H15	119.00
C7—C8—C9	119.5 (2)	N1—C16—H16A	108.00
Cl2—C9—C4	119.74 (18)	N1—C16—H16B	108.00
Cl2—C9—C8	119.78 (18)	C17—C16—H16A	108.00
C4—C9—C8	120.5 (2)	C17—C16—H16B	108.00
C3—C10—C11	119.2 (2)	H16A—C16—H16B	107.00
C3—C10—C15	122.2 (2)	C17—C18—H18	119.00
C11—C10—C15	118.5 (2)	C19—C18—H18	119.00
C10—C11—C12	121.4 (2)	C18—C19—H19	120.00
C11—C12—C13	118.5 (3)	C20—C19—H19	120.00
N2—C13—C12	119.9 (2)	C20—C21—H21	120.00
N2—C13—C14	118.3 (2)	C22—C21—H21	120.00
C12—C13—C14	121.8 (2)	C17—C22—H22	119.00
C13—C14—C15	118.7 (2)	C21—C22—H22	119.00
C10—C15—C14	121.2 (2)	O5—C23—H23A	109.00
N1—C16—C17	115.36 (19)	O5—C23—H23B	109.00
C16—C17—C18	120.0 (2)	O5—C23—H23C	109.00
C16—C17—C22	122.3 (2)	H23A—C23—H23B	110.00
C18—C17—C22	117.6 (2)	H23A—C23—H23C	110.00
C17—C18—C19	122.1 (2)	H23B—C23—H23C	109.00
C18—C19—C20	119.5 (2)

C2—O2—C4—C5	2.3 (3)	O2—C4—C5—C6	176.2 (2)
C4—O2—C2—C1	−71.2 (3)	C5—C4—C9—C8	2.1 (4)
C4—O2—C2—C3	−166.47 (19)	O2—C4—C9—Cl2	3.1 (3)
C2—O2—C4—C9	−179.5 (2)	C9—C4—C5—C6	−1.9 (4)
C23—O5—C20—C21	−180.0 (2)	C4—C5—C6—C7	0.1 (4)
C23—O5—C20—C19	−1.0 (4)	C5—C6—C7—Cl1	−177.73 (19)
C16—N1—C1—C2	−173.9 (2)	C5—C6—C7—C8	1.4 (4)
C3—N1—C1—O1	−177.6 (3)	C6—C7—C8—C9	−1.2 (4)
C1—N1—C16—C17	103.0 (3)	Cl1—C7—C8—C9	177.94 (18)
C3—N1—C16—C17	−72.5 (3)	C7—C8—C9—Cl2	−179.75 (19)
C16—N1—C3—C10	−70.0 (3)	C7—C8—C9—C4	−0.5 (4)
C1—N1—C3—C2	−2.85 (19)	C3—C10—C15—C14	−177.0 (2)
C16—N1—C3—C2	173.8 (2)	C3—C10—C11—C12	175.9 (2)
C3—N1—C1—C2	2.90 (19)	C11—C10—C15—C14	−0.1 (3)
C1—N1—C3—C10	113.4 (2)	C15—C10—C11—C12	−1.1 (4)
C16—N1—C1—O1	5.7 (5)	C10—C11—C12—C13	1.1 (4)
O4—N2—C13—C14	−0.5 (4)	C11—C12—C13—N2	−179.8 (2)
O3—N2—C13—C12	−1.0 (4)	C11—C12—C13—C14	0.0 (4)
O4—N2—C13—C12	179.2 (3)	N2—C13—C14—C15	178.7 (2)
O3—N2—C13—C14	179.2 (3)	C12—C13—C14—C15	−1.1 (4)
N1—C1—C2—C3	−2.72 (18)	C13—C14—C15—C10	1.2 (4)
O1—C1—C2—O2	67.4 (4)	N1—C16—C17—C22	−47.4 (3)
O1—C1—C2—C3	177.8 (3)	N1—C16—C17—C18	136.2 (2)
N1—C1—C2—O2	−113.1 (2)	C16—C17—C22—C21	−176.6 (2)
C1—C2—C3—N1	2.49 (16)	C18—C17—C22—C21	−0.1 (4)
O2—C2—C3—C10	2.4 (3)	C16—C17—C18—C19	175.8 (2)
C1—C2—C3—C10	−115.4 (2)	C22—C17—C18—C19	−0.8 (4)
O2—C2—C3—N1	120.25 (19)	C17—C18—C19—C20	1.3 (4)
C2—C3—C10—C15	94.1 (3)	C18—C19—C20—C21	−0.9 (4)
N1—C3—C10—C15	−4.9 (3)	C18—C19—C20—O5	−179.9 (2)
C2—C3—C10—C11	−82.7 (3)	O5—C20—C21—C22	179.1 (2)
N1—C3—C10—C11	178.3 (2)	C19—C20—C21—C22	0.0 (4)
C5—C4—C9—Cl2	−178.70 (19)	C20—C21—C22—C17	0.5 (4)
O2—C4—C9—C8	−176.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.98	2.58	3.417 (3)	143
C6—H6···O5ⁱⁱ	0.93	2.57	3.328 (3)	139
C12—H12···O3ⁱⁱⁱ	0.93	2.57	3.495 (4)	176
C16—H16A···Cg^iv	0.97	2.70	3.649 (3)	166

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

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1ⁱ	0.98	2.58	3.417 (3)	143
C6—H6···O5ⁱⁱ	0.93	2.57	3.328 (3)	139
C12—H12···O3ⁱⁱⁱ	0.93	2.57	3.495 (4)	176
C16—H16A···Cg^iv	0.97	2.70	3.649 (3)	166

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

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). AJ and RH thank the Shiraz University Research Council for financial support.

References

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Volume 70| Part 8| August 2014| Pages o835-o836

doi:10.1107/S1600536814015013

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

3-(2,4-Di­chloro­phen­­oxy)-1-(4-meth­­oxy­benz­yl)-4-(4-nitro­phen­yl)azetidin-2-one

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organic compounds

3-(2,4-Dichlorophenoxy)-1-(4-methoxybenzyl)-4-(4-nitrophenyl)azetidin-2-one