1-(4-Meth-oxy-phen-yl)-4-(4-methyl-phen-yl)-3-phen-oxy-azetidin-2-one.

The central β-lactam ring of the title compound, C(23)H(21)NO(3), is almost planar (r.m.s. deviation = 0.032Å). The meth-oxy-benzene ring is almost coplanar with the β-lactam ring [dihedral angle = 1.87 (11)°], whereas the tolyl ring is almost normal to it [75.73 (12)°]. The dihedral angle between the β-lactam ring and the O-bonded phenyl ring is 51.95 (12)°. An intra-molecular C-H⋯O inter-action generates an S(6) ring. The crystal structure features inter-molecular C-H⋯O hydrogen bonds, forming layers parallel to (011), and weak C-H⋯π inter-actions. Two aromatic π-π stacking inter-actions [centroid-centroid distances = 3.6744 (12) and 3.6799 (11) Å] are also observed.

Related literature

For the synthesis of the title compound and background to the biological properties of β-lactam compounds, see: Jarrahpour & Zarei (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C23H21NO3

M = 359.41

Triclinic,

a = 6.0764 (3) Å

b = 9.9545 (5) Å

c = 16.4519 (10) Å

α = 104.360 (4)°

β = 91.261 (5)°

γ = 97.724 (4)°

V = 953.71 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.60 × 0.37 × 0.12 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.964, T max = 0.990

13748 measured reflections

3961 independent reflections

2608 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.119

S = 1.03

3961 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.17 e Å−3

Data collection: X-AREA (Stoe & Cie, 2002 ▶); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000663/hb5783sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000663/hb5783Isup2.hkl

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

C23H21NO3	Z = 2
Mr = 359.41	F(000) = 380
Triclinic, P1	Dx = 1.252 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.0764 (3) Å	Cell parameters from 19074 reflections
b = 9.9545 (5) Å	θ = 2.1–27.6°
c = 16.4519 (10) Å	µ = 0.08 mm−1
α = 104.360 (4)°	T = 296 K
β = 91.261 (5)°	Prism, colourless
γ = 97.724 (4)°	0.60 × 0.37 × 0.12 mm
V = 953.71 (9) Å3

Stoe IPDS 2 diffractometer	3961 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2608 reflections with I > 2σ(I)
plane graphite	Rint = 0.055
Detector resolution: 6.67 pixels mm-1	θmax = 26.5°, θmin = 2.1°
ω scans	h = −7→7
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.964, Tmax = 0.990	l = −20→20
13748 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0548P)2 + 0.0685P] where P = (Fo2 + 2Fc2)/3
3961 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 0.13 e Å−3
0 restraints	Δρmin = −0.17 e Å−3

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
O1	0.1189 (2)	0.46929 (12)	0.24918 (8)	0.0593 (4)
O2	−0.0121 (2)	0.69814 (13)	0.39817 (9)	0.0661 (5)
O3	0.5557 (2)	1.34079 (13)	0.45143 (10)	0.0691 (5)
N1	0.3435 (2)	0.76262 (13)	0.35417 (9)	0.0449 (4)
C1	0.0980 (3)	0.32558 (17)	0.22621 (11)	0.0466 (5)
C2	−0.0981 (3)	0.2579 (2)	0.18159 (14)	0.0659 (7)
C3	−0.1326 (4)	0.1146 (2)	0.15480 (17)	0.0855 (9)
C4	0.0243 (5)	0.0375 (2)	0.17266 (18)	0.0906 (10)
C5	0.2170 (5)	0.1043 (2)	0.21619 (16)	0.0841 (10)
C6	0.2565 (3)	0.2490 (2)	0.24332 (13)	0.0626 (7)
C7	0.2563 (3)	0.54632 (17)	0.32009 (11)	0.0493 (6)
C8	0.1608 (3)	0.67635 (17)	0.36523 (11)	0.0481 (6)
C9	0.4601 (3)	0.65118 (17)	0.30514 (11)	0.0456 (5)
C10	0.5040 (3)	0.66017 (17)	0.21748 (11)	0.0461 (5)
C11	0.3614 (3)	0.7126 (2)	0.17006 (12)	0.0590 (7)
C12	0.4120 (4)	0.7251 (2)	0.09059 (14)	0.0725 (8)
C13	0.6024 (4)	0.6850 (2)	0.05514 (13)	0.0711 (8)
C14	0.7428 (3)	0.6312 (2)	0.10147 (15)	0.0733 (8)
C15	0.6962 (3)	0.6196 (2)	0.18176 (13)	0.0603 (7)
C16	0.6603 (5)	0.7014 (3)	−0.03125 (17)	0.1131 (13)
C17	0.4029 (2)	0.90918 (16)	0.37839 (10)	0.0417 (5)
C18	0.2574 (3)	0.99309 (17)	0.42190 (11)	0.0489 (6)
C19	0.3149 (3)	1.13583 (18)	0.44533 (12)	0.0523 (6)
C20	0.5185 (3)	1.19731 (17)	0.42538 (11)	0.0494 (6)
C21	0.6635 (3)	1.11455 (18)	0.38189 (12)	0.0514 (6)
C22	0.6062 (3)	0.97064 (18)	0.35878 (11)	0.0488 (6)
C23	0.7547 (3)	1.4105 (2)	0.42925 (15)	0.0691 (7)
H2	−0.20600	0.30950	0.16980	0.0790*
H3	−0.26370	0.06920	0.12420	0.1030*
H4	−0.00100	−0.05980	0.15510	0.1090*
H5	0.32400	0.05210	0.22790	0.1010*
H6	0.38930	0.29390	0.27290	0.0750*
H7	0.29430	0.48910	0.35750	0.0590*
H9	0.59590	0.64290	0.33570	0.0550*
H11	0.23000	0.73970	0.19210	0.0710*
H12	0.31430	0.76160	0.06040	0.0870*
H14	0.87190	0.60190	0.07840	0.0880*
H15	0.79530	0.58410	0.21190	0.0720*
H16A	0.77970	0.77730	−0.02580	0.1360*
H16B	0.53250	0.72090	−0.05910	0.1360*
H16C	0.70560	0.61630	−0.06360	0.1360*
H18	0.12050	0.95250	0.43520	0.0590*
H19	0.21710	1.19170	0.47470	0.0630*
H21	0.79960	1.15550	0.36810	0.0620*
H22	0.70480	0.91470	0.32990	0.0590*
H23A	0.75830	1.38950	0.36910	0.0830*
H23B	0.87980	1.37960	0.45200	0.0830*
H23C	0.76110	1.50980	0.45150	0.0830*

	U11	U22	U33	U12	U13	U23
O1	0.0676 (7)	0.0352 (7)	0.0707 (9)	−0.0008 (5)	−0.0211 (6)	0.0116 (6)
O2	0.0539 (7)	0.0533 (8)	0.0853 (10)	−0.0075 (6)	0.0196 (7)	0.0132 (7)
O3	0.0758 (8)	0.0372 (7)	0.0866 (10)	−0.0080 (6)	0.0139 (7)	0.0091 (6)
N1	0.0449 (7)	0.0359 (7)	0.0502 (9)	−0.0019 (6)	0.0055 (6)	0.0079 (6)
C1	0.0499 (9)	0.0379 (9)	0.0504 (10)	0.0010 (7)	0.0033 (7)	0.0112 (8)
C2	0.0555 (10)	0.0520 (12)	0.0820 (15)	0.0035 (9)	−0.0070 (10)	0.0048 (10)
C3	0.0791 (14)	0.0564 (14)	0.102 (2)	−0.0123 (11)	−0.0153 (13)	−0.0020 (12)
C4	0.125 (2)	0.0410 (12)	0.096 (2)	0.0026 (13)	−0.0111 (16)	0.0054 (12)
C5	0.1158 (19)	0.0507 (13)	0.0853 (17)	0.0252 (12)	−0.0183 (14)	0.0114 (12)
C6	0.0673 (11)	0.0499 (11)	0.0688 (13)	0.0097 (9)	−0.0111 (10)	0.0125 (10)
C7	0.0540 (9)	0.0372 (9)	0.0547 (11)	−0.0006 (7)	−0.0069 (8)	0.0125 (8)
C8	0.0474 (9)	0.0409 (9)	0.0536 (11)	−0.0043 (7)	0.0018 (8)	0.0135 (8)
C9	0.0438 (8)	0.0399 (9)	0.0516 (10)	0.0048 (7)	−0.0029 (7)	0.0099 (8)
C10	0.0442 (8)	0.0394 (9)	0.0514 (11)	0.0043 (7)	0.0003 (7)	0.0064 (8)
C11	0.0564 (10)	0.0684 (13)	0.0573 (12)	0.0190 (9)	0.0046 (9)	0.0198 (10)
C12	0.0798 (14)	0.0818 (16)	0.0598 (13)	0.0099 (11)	−0.0018 (11)	0.0267 (11)
C13	0.0748 (13)	0.0746 (15)	0.0527 (13)	−0.0134 (11)	0.0052 (10)	0.0081 (11)
C14	0.0585 (11)	0.0793 (15)	0.0693 (15)	0.0020 (10)	0.0201 (11)	−0.0022 (12)
C15	0.0498 (9)	0.0588 (12)	0.0684 (14)	0.0119 (8)	0.0036 (9)	0.0067 (10)
C16	0.127 (2)	0.132 (3)	0.0654 (17)	−0.0295 (19)	0.0188 (15)	0.0213 (16)
C17	0.0442 (8)	0.0363 (9)	0.0422 (9)	−0.0027 (6)	0.0009 (7)	0.0099 (7)
C18	0.0446 (8)	0.0454 (10)	0.0540 (11)	−0.0025 (7)	0.0118 (7)	0.0116 (8)
C19	0.0547 (9)	0.0424 (10)	0.0568 (11)	0.0033 (8)	0.0126 (8)	0.0080 (8)
C20	0.0562 (9)	0.0366 (9)	0.0517 (11)	−0.0049 (7)	0.0019 (8)	0.0103 (8)
C21	0.0437 (8)	0.0464 (10)	0.0613 (12)	−0.0075 (7)	0.0066 (8)	0.0157 (8)
C22	0.0427 (8)	0.0457 (10)	0.0552 (11)	0.0008 (7)	0.0075 (7)	0.0103 (8)
C23	0.0711 (12)	0.0471 (11)	0.0829 (15)	−0.0178 (9)	−0.0034 (10)	0.0198 (10)

O1—C1	1.373 (2)	C18—C19	1.371 (3)
O1—C7	1.410 (2)	C19—C20	1.388 (3)
O2—C8	1.214 (2)	C20—C21	1.378 (3)
O3—C20	1.371 (2)	C21—C22	1.381 (3)
O3—C23	1.413 (2)	C2—H2	0.9300
N1—C8	1.354 (2)	C3—H3	0.9300
N1—C9	1.475 (2)	C4—H4	0.9300
N1—C17	1.408 (2)	C5—H5	0.9300
C1—C2	1.383 (3)	C6—H6	0.9300
C1—C6	1.371 (3)	C7—H7	0.9800
C2—C3	1.370 (3)	C9—H9	0.9800
C3—C4	1.371 (4)	C11—H11	0.9300
C4—C5	1.358 (4)	C12—H12	0.9300
C5—C6	1.384 (3)	C14—H14	0.9300
C7—C8	1.519 (3)	C15—H15	0.9300
C7—C9	1.574 (3)	C16—H16A	0.9600
C9—C10	1.495 (2)	C16—H16B	0.9600
C10—C11	1.388 (3)	C16—H16C	0.9600
C10—C15	1.383 (3)	C18—H18	0.9300
C11—C12	1.381 (3)	C19—H19	0.9300
C12—C13	1.370 (3)	C21—H21	0.9300
C13—C14	1.376 (3)	C22—H22	0.9300
C13—C16	1.514 (3)	C23—H23A	0.9600
C14—C15	1.386 (3)	C23—H23B	0.9600
C17—C18	1.386 (2)	C23—H23C	0.9600
C17—C22	1.385 (2)
C1—O1—C7	120.21 (14)	C3—C2—H2	120.00
C20—O3—C23	117.71 (15)	C2—C3—H3	120.00
C8—N1—C9	96.00 (13)	C4—C3—H3	120.00
C8—N1—C17	132.78 (13)	C3—C4—H4	120.00
C9—N1—C17	131.20 (13)	C5—C4—H4	120.00
O1—C1—C2	115.45 (16)	C4—C5—H5	120.00
O1—C1—C6	124.67 (17)	C6—C5—H5	120.00
C2—C1—C6	119.87 (17)	C1—C6—H6	120.00
C1—C2—C3	119.70 (19)	C5—C6—H6	120.00
C2—C3—C4	120.6 (2)	O1—C7—H7	113.00
C3—C4—C5	119.5 (2)	C8—C7—H7	113.00
C4—C5—C6	120.9 (2)	C9—C7—H7	113.00
C1—C6—C5	119.4 (2)	N1—C9—H9	112.00
O1—C7—C8	111.20 (14)	C7—C9—H9	112.00
O1—C7—C9	117.37 (14)	C10—C9—H9	111.00
C8—C7—C9	85.70 (13)	C10—C11—H11	120.00
O2—C8—N1	132.64 (17)	C12—C11—H11	120.00
O2—C8—C7	134.97 (17)	C11—C12—H12	119.00
N1—C8—C7	92.39 (14)	C13—C12—H12	119.00
N1—C9—C7	85.80 (12)	C13—C14—H14	119.00
N1—C9—C10	115.03 (14)	C15—C14—H14	119.00
C7—C9—C10	119.15 (15)	C10—C15—H15	120.00
C9—C10—C11	122.47 (16)	C14—C15—H15	120.00
C9—C10—C15	119.98 (17)	C13—C16—H16A	109.00
C11—C10—C15	117.52 (17)	C13—C16—H16B	109.00
C10—C11—C12	120.93 (18)	C13—C16—H16C	109.00
C11—C12—C13	121.6 (2)	H16A—C16—H16B	110.00
C12—C13—C14	117.7 (2)	H16A—C16—H16C	109.00
C12—C13—C16	121.6 (2)	H16B—C16—H16C	109.00
C14—C13—C16	120.7 (2)	C17—C18—H18	120.00
C13—C14—C15	121.53 (19)	C19—C18—H18	120.00
C10—C15—C14	120.74 (18)	C18—C19—H19	120.00
N1—C17—C18	120.09 (13)	C20—C19—H19	120.00
N1—C17—C22	120.40 (14)	C20—C21—H21	120.00
C18—C17—C22	119.52 (16)	C22—C21—H21	120.00
C17—C18—C19	120.12 (16)	C17—C22—H22	120.00
C18—C19—C20	120.29 (17)	C21—C22—H22	120.00
O3—C20—C19	114.80 (16)	O3—C23—H23A	109.00
O3—C20—C21	125.32 (16)	O3—C23—H23B	109.00
C19—C20—C21	119.88 (17)	O3—C23—H23C	109.00
C20—C21—C22	119.83 (17)	H23A—C23—H23B	109.00
C17—C22—C21	120.36 (16)	H23A—C23—H23C	109.00
C1—C2—H2	120.00	H23B—C23—H23C	109.00
C7—O1—C1—C2	154.15 (17)	O1—C7—C8—N1	−120.21 (15)
C7—O1—C1—C6	−26.9 (3)	C9—C7—C8—O2	176.8 (2)
C1—O1—C7—C8	−145.56 (15)	O1—C7—C9—C10	−2.5 (2)
C1—O1—C7—C9	118.10 (17)	C8—C7—C9—N1	2.27 (12)
C23—O3—C20—C21	2.6 (3)	O1—C7—C8—O2	59.0 (3)
C23—O3—C20—C19	−176.70 (17)	N1—C9—C10—C11	−32.4 (2)
C8—N1—C9—C7	−2.55 (13)	N1—C9—C10—C15	145.45 (17)
C17—N1—C8—O2	1.7 (3)	C7—C9—C10—C11	67.2 (2)
C9—N1—C8—O2	−176.6 (2)	C7—C9—C10—C15	−114.9 (2)
C9—N1—C8—C7	2.64 (14)	C9—C10—C15—C14	−178.05 (18)
C17—N1—C8—C7	−179.03 (17)	C15—C10—C11—C12	−0.8 (3)
C17—N1—C9—C7	179.07 (16)	C9—C10—C11—C12	177.14 (18)
C9—N1—C17—C18	177.01 (16)	C11—C10—C15—C14	−0.1 (3)
C8—N1—C17—C22	179.43 (17)	C10—C11—C12—C13	0.8 (3)
C9—N1—C17—C22	−2.8 (3)	C11—C12—C13—C14	0.1 (3)
C8—N1—C17—C18	−0.8 (3)	C11—C12—C13—C16	−178.7 (2)
C8—N1—C9—C10	117.76 (16)	C12—C13—C14—C15	−1.0 (3)
C17—N1—C9—C10	−60.6 (2)	C16—C13—C14—C15	177.9 (2)
O1—C1—C6—C5	−179.42 (19)	C13—C14—C15—C10	1.0 (3)
O1—C1—C2—C3	178.99 (19)	N1—C17—C22—C21	179.40 (16)
C6—C1—C2—C3	0.0 (3)	C18—C17—C22—C21	−0.4 (3)
C2—C1—C6—C5	−0.6 (3)	N1—C17—C18—C19	−179.84 (16)
C1—C2—C3—C4	0.8 (4)	C22—C17—C18—C19	−0.1 (3)
C2—C3—C4—C5	−1.0 (4)	C17—C18—C19—C20	0.3 (3)
C3—C4—C5—C6	0.5 (4)	C18—C19—C20—C21	0.0 (3)
C4—C5—C6—C1	0.3 (4)	C18—C19—C20—O3	179.34 (17)
O1—C7—C9—N1	113.95 (15)	O3—C20—C21—C22	−179.72 (17)
C8—C7—C9—C10	−114.14 (17)	C19—C20—C21—C22	−0.4 (3)
C9—C7—C8—N1	−2.47 (13)	C20—C21—C22—C17	0.6 (3)

Cg4 is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2	0.93	2.47	3.093 (2)	125
C9—H9···O2i	0.98	2.51	3.446 (2)	160
C15—H15···O1i	0.93	2.54	3.435 (2)	162
C19—H19···O2ii	0.93	2.54	3.415 (2)	156
C23—H23C···O2iii	0.96	2.52	3.184 (2)	126
C5—H5···Cg4iv	0.93	2.96	3.544 (3)	122

	Ring-2	Ring-3	Ring-4
Ring-1	51.95 (12)	75.73 (12)	1.87 (11)
Ring-2		86.93 (11)	50.10 (10)
Ring-3			76.54 (9)

Table 1

Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2	0.93	2.47	3.093 (2)	125
C9—H9⋯O2i	0.98	2.51	3.446 (2)	160
C15—H15⋯O1i	0.93	2.54	3.435 (2)	162
C19—H19⋯O2ii	0.93	2.54	3.415 (2)	156
C23—H23C⋯O2iii	0.96	2.52	3.184 (2)	126
C5—H5⋯Cg4iv	0.93	2.96	3.544 (3)	122

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