Crystal structure of 1-(4-meth-oxy-phen-yl)-4-(4-nitro-phen-yl)-3-phen-oxy-azetidin-2-one.

In the title compound, C22H18N2O5, the central β-lactam ring (r.m.s. deviation = 0.002 Å) makes dihedral angles of 64.21 (14), 82.35 (12) and 20.66 (13)° with the phenyl ring and the nitro- and meth-oxy-benzene rings, respectively. The mol-ecular structure is stabilized by an intra-molecular C-H⋯O hydrogen bond. In the crystal, mol-ecules are linked via C-H⋯O hydrogen bonds, forming slabs lying parallel to (111). The slabs are linked via C-H⋯π inter-actions, forming a three-dimensional network.

Related literature

For general properties and applications in medicinal chemistry of four-membered monocyclic aza-heterocycles, see: Bode et al. (1989 ▸); Gerona-Navarro et al. (2004 ▸); Grafe (1992 ▸); Gérard et al. (2004 ▸); Mehta et al. (2010 ▸); Setti et al. (2005 ▸); Singh et al. (2008 ▸); Southgate (1994 ▸); Sutton et al. (2004 ▸); Sperka et al. (2005 ▸). For related structures, see: Akkurt et al. (2011 ▸); Butcher et al. (2011 ▸).

Experimental

Crystal data

C22H18N2O5

M = 390.38

Triclinic,

a = 9.8044 (3) Å

b = 10.6483 (3) Å

c = 11.1573 (3) Å

α = 66.957 (1)°

β = 70.105 (1)°

γ = 65.973 (1)°

V = 956.06 (5) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

16870 measured reflections

3586 independent reflections

2860 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.125

S = 1.09

3586 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.17 e Å−3

Data collection: n class="Gene">APEX2 (Bruker, 2007 ▸); cell refinement: SAINT (Bruker, 2007 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S2056989014025833/su5026sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989014025833/su5026Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989014025833/su5026Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989014025833/su5026fig1.tif

Perspective view of the mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

a . DOI: 10.1107/S2056989014025833/su5026fig2.tif

View of the hydrogen bonding and mol­ecular packing of the title compound along a axis (only H atoms involved in hydrogen bonding are shown; see Table 1 for details).

CCDC reference: 1036033

Additional supporting information: crystallographic information; 3D view; checkCIF report

C22H18N2O5	Z = 2
Mr = 390.38	F(000) = 408
Triclinic, P1	Dx = 1.356 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8044 (3) Å	Cell parameters from 8412 reflections
b = 10.6483 (3) Å	θ = 2.2–31.2°
c = 11.1573 (3) Å	µ = 0.10 mm−1
α = 66.957 (1)°	T = 296 K
β = 70.105 (1)°	Prism, colourless
γ = 65.973 (1)°	0.30 × 0.20 × 0.15 mm
V = 956.06 (5) Å3

Bruker APEXII CCD diffractometer	2860 reflections with I > 2σ(I)
Radiation source: sealed tube	Rint = 0.027
Graphite monochromator	θmax = 26.4°, θmin = 2.0°
φ and ω scans	h = −12→12
16870 measured reflections	k = −13→13
3586 independent reflections	l = −13→13

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046	H-atom parameters constrained
wR(F2) = 0.125	w = 1/[σ2(Fo2) + (0.054P)2 + 0.2069P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
3586 reflections	Δρmax = 0.22 e Å−3
257 parameters	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	0.19496 (17)	1.0034 (2)	0.46300 (14)	0.0891 (6)
O2	0.50869 (15)	0.76274 (16)	0.48302 (11)	0.0619 (5)
O3	1.15569 (17)	0.9287 (2)	0.20735 (17)	0.0938 (7)
O4	1.22134 (17)	0.7927 (2)	0.08655 (19)	0.1013 (8)
O5	0.20258 (17)	1.58682 (16)	−0.07766 (16)	0.0783 (6)
N1	0.38058 (14)	1.03204 (17)	0.26380 (13)	0.0488 (5)
N2	1.12538 (18)	0.86578 (19)	0.15529 (16)	0.0629 (6)
C1	0.3090 (2)	0.9617 (2)	0.38519 (16)	0.0569 (5)
C2	0.42887 (19)	0.8176 (2)	0.37976 (16)	0.0569 (5)
C3	0.50356 (17)	0.90236 (19)	0.23890 (14)	0.0450 (5)
C4	0.6280 (2)	0.6349 (2)	0.48961 (17)	0.0575 (7)
C5	0.7040 (3)	0.5907 (3)	0.5903 (2)	0.0768 (9)
C6	0.8249 (3)	0.4657 (3)	0.6043 (3)	0.0928 (10)
C7	0.8714 (3)	0.3834 (3)	0.5201 (3)	0.0896 (10)
C8	0.7957 (3)	0.4277 (3)	0.4207 (2)	0.0775 (8)
C9	0.6737 (2)	0.5537 (2)	0.40422 (19)	0.0663 (7)
C10	0.66584 (17)	0.89768 (17)	0.21679 (14)	0.0394 (5)
C11	0.70598 (18)	0.95456 (19)	0.28763 (15)	0.0459 (5)
C12	0.85691 (19)	0.94417 (19)	0.26790 (15)	0.0477 (5)
C13	0.96466 (17)	0.87828 (18)	0.17624 (15)	0.0448 (5)
C14	0.92900 (19)	0.82065 (19)	0.10398 (16)	0.0491 (5)
C15	0.77834 (18)	0.83228 (18)	0.12446 (15)	0.0452 (5)
C16	0.33669 (17)	1.1729 (2)	0.17642 (16)	0.0473 (6)
C17	0.1869 (2)	1.2640 (2)	0.1967 (2)	0.0628 (7)
C18	0.1477 (2)	1.4003 (2)	0.1106 (2)	0.0687 (8)
C19	0.2549 (2)	1.4496 (2)	0.0030 (2)	0.0569 (7)
C20	0.4030 (2)	1.3594 (2)	−0.01778 (18)	0.0540 (6)
C21	0.44279 (18)	1.2218 (2)	0.06850 (17)	0.0505 (6)
C22	0.3131 (3)	1.6499 (3)	−0.1745 (3)	0.0853 (10)
H2	0.38870	0.74890	0.37620	0.0680*
H3	0.49120	0.87820	0.16780	0.0540*
H5	0.67340	0.64540	0.64820	0.0920*
H6	0.87620	0.43620	0.67200	0.1120*
H7	0.95330	0.29860	0.53050	0.1070*
H8	0.82660	0.37250	0.36340	0.0930*
H9	0.62310	0.58320	0.33610	0.0800*
H11	0.63100	0.99990	0.34870	0.0550*
H12	0.88460	0.98110	0.31580	0.0570*
H14	1.00460	0.77530	0.04320	0.0590*
H15	0.75150	0.79570	0.07560	0.0540*
H17	0.11350	1.23260	0.26840	0.0750*
H18	0.04730	1.46060	0.12470	0.0820*
H20	0.47610	1.39090	−0.08980	0.0650*
H21	0.54290	1.16120	0.05350	0.0610*
H22A	0.38120	1.65160	−0.13090	0.1280*
H22B	0.26230	1.74640	−0.22200	0.1280*
H22C	0.37030	1.59430	−0.23600	0.1280*

	U11	U22	U33	U12	U13	U23
O1	0.0574 (9)	0.1347 (15)	0.0630 (8)	−0.0226 (9)	0.0108 (7)	−0.0452 (9)
O2	0.0622 (8)	0.0815 (10)	0.0467 (6)	−0.0293 (8)	−0.0155 (6)	−0.0135 (6)
O3	0.0683 (10)	0.1387 (16)	0.1022 (11)	−0.0573 (11)	−0.0252 (8)	−0.0319 (11)
O4	0.0394 (8)	0.1325 (16)	0.1246 (14)	−0.0241 (10)	0.0052 (9)	−0.0532 (13)
O5	0.0615 (9)	0.0556 (10)	0.1099 (11)	−0.0048 (8)	−0.0253 (8)	−0.0250 (8)
N1	0.0310 (7)	0.0673 (11)	0.0485 (7)	−0.0124 (7)	−0.0042 (5)	−0.0244 (7)
N2	0.0428 (9)	0.0751 (12)	0.0627 (9)	−0.0265 (9)	−0.0142 (7)	−0.0017 (8)
C1	0.0444 (7)	0.0846 (10)	0.0485 (6)	−0.0267 (6)	−0.0063 (5)	−0.0231 (7)
C2	0.0444 (7)	0.0846 (10)	0.0485 (6)	−0.0267 (6)	−0.0063 (5)	−0.0231 (7)
C3	0.0373 (8)	0.0606 (12)	0.0440 (8)	−0.0166 (8)	−0.0094 (6)	−0.0207 (7)
C4	0.0511 (11)	0.0701 (14)	0.0490 (9)	−0.0322 (11)	−0.0124 (8)	−0.0003 (9)
C5	0.0813 (15)	0.0930 (18)	0.0630 (11)	−0.0416 (15)	−0.0289 (11)	−0.0038 (11)
C6	0.0886 (18)	0.101 (2)	0.0842 (16)	−0.0368 (17)	−0.0482 (14)	0.0097 (15)
C7	0.0692 (15)	0.0826 (18)	0.0955 (17)	−0.0272 (14)	−0.0310 (13)	0.0099 (14)
C8	0.0671 (14)	0.0733 (16)	0.0806 (14)	−0.0245 (13)	−0.0168 (11)	−0.0079 (11)
C9	0.0632 (12)	0.0766 (15)	0.0600 (11)	−0.0293 (12)	−0.0187 (9)	−0.0090 (10)
C10	0.0349 (8)	0.0431 (10)	0.0399 (7)	−0.0114 (7)	−0.0105 (6)	−0.0109 (6)
C11	0.0400 (9)	0.0550 (11)	0.0461 (8)	−0.0132 (8)	−0.0083 (7)	−0.0211 (7)
C12	0.0481 (9)	0.0544 (11)	0.0488 (8)	−0.0215 (9)	−0.0169 (7)	−0.0123 (7)
C13	0.0349 (8)	0.0463 (10)	0.0471 (8)	−0.0154 (8)	−0.0127 (6)	−0.0017 (7)
C14	0.0397 (9)	0.0520 (11)	0.0502 (8)	−0.0119 (8)	−0.0041 (7)	−0.0170 (8)
C15	0.0420 (9)	0.0516 (11)	0.0470 (8)	−0.0158 (8)	−0.0082 (7)	−0.0197 (7)
C16	0.0325 (8)	0.0626 (12)	0.0554 (9)	−0.0097 (8)	−0.0105 (7)	−0.0308 (8)
C17	0.0358 (9)	0.0778 (15)	0.0706 (11)	−0.0106 (10)	−0.0028 (8)	−0.0327 (11)
C18	0.0370 (10)	0.0707 (15)	0.0918 (14)	0.0017 (10)	−0.0103 (9)	−0.0401 (12)
C19	0.0453 (10)	0.0519 (13)	0.0806 (12)	−0.0058 (9)	−0.0210 (9)	−0.0303 (10)
C20	0.0401 (9)	0.0593 (13)	0.0666 (10)	−0.0137 (9)	−0.0116 (8)	−0.0247 (9)
C21	0.0304 (8)	0.0616 (13)	0.0609 (9)	−0.0083 (8)	−0.0098 (7)	−0.0261 (9)
C22	0.0902 (17)	0.0591 (15)	0.1103 (18)	−0.0270 (13)	−0.0321 (14)	−0.0162 (13)

O1—C1	1.199 (3)	C14—C15	1.376 (3)
O2—C2	1.413 (2)	C16—C17	1.391 (3)
O2—C4	1.382 (3)	C16—C21	1.379 (3)
O3—N2	1.208 (3)	C17—C18	1.372 (3)
O4—N2	1.208 (3)	C18—C19	1.385 (3)
O5—C19	1.372 (3)	C19—C20	1.376 (3)
O5—C22	1.421 (4)	C20—C21	1.383 (3)
N1—C1	1.369 (2)	C2—H2	0.9800
N1—C3	1.468 (3)	C3—H3	0.9800
N1—C16	1.414 (2)	C5—H5	0.9300
N2—C13	1.469 (3)	C6—H6	0.9300
C1—C2	1.515 (3)	C7—H7	0.9300
C2—C3	1.570 (2)	C8—H8	0.9300
C3—C10	1.508 (3)	C9—H9	0.9300
C4—C5	1.382 (3)	C11—H11	0.9300
C4—C9	1.377 (3)	C12—H12	0.9300
C5—C6	1.371 (4)	C14—H14	0.9300
C6—C7	1.373 (4)	C15—H15	0.9300
C7—C8	1.367 (4)	C17—H17	0.9300
C8—C9	1.384 (4)	C18—H18	0.9300
C10—C11	1.388 (3)	C20—H20	0.9300
C10—C15	1.388 (2)	C21—H21	0.9300
C11—C12	1.384 (3)	C22—H22A	0.9600
C12—C13	1.370 (2)	C22—H22B	0.9600
C13—C14	1.379 (3)	C22—H22C	0.9600
C2—O2—C4	118.48 (15)	C18—C19—C20	119.10 (19)
C19—O5—C22	117.6 (2)	C19—C20—C21	119.87 (19)
C1—N1—C3	95.42 (14)	C16—C21—C20	121.16 (19)
C1—N1—C16	133.12 (17)	O2—C2—H2	113.00
C3—N1—C16	130.07 (13)	C1—C2—H2	113.00
O3—N2—O4	123.0 (2)	C3—C2—H2	113.00
O3—N2—C13	118.75 (18)	N1—C3—H3	111.00
O4—N2—C13	118.26 (19)	C2—C3—H3	111.00
O1—C1—N1	132.1 (2)	C10—C3—H3	111.00
O1—C1—C2	135.63 (18)	C4—C5—H5	120.00
N1—C1—C2	92.29 (15)	C6—C5—H5	120.00
O2—C2—C1	110.35 (15)	C5—C6—H6	119.00
O2—C2—C3	117.28 (17)	C7—C6—H6	120.00
C1—C2—C3	85.76 (13)	C6—C7—H7	120.00
N1—C3—C2	86.47 (13)	C8—C7—H7	120.00
N1—C3—C10	117.56 (16)	C7—C8—H8	120.00
C2—C3—C10	117.93 (14)	C9—C8—H8	120.00
O2—C4—C5	115.15 (19)	C4—C9—H9	120.00
O2—C4—C9	124.79 (18)	C8—C9—H9	120.00
C5—C4—C9	120.1 (2)	C10—C11—H11	120.00
C4—C5—C6	119.5 (2)	C12—C11—H11	120.00
C5—C6—C7	121.1 (3)	C11—C12—H12	121.00
C6—C7—C8	119.2 (3)	C13—C12—H12	121.00
C7—C8—C9	120.9 (2)	C13—C14—H14	121.00
C4—C9—C8	119.3 (2)	C15—C14—H14	121.00
C3—C10—C11	121.92 (15)	C10—C15—H15	119.00
C3—C10—C15	118.78 (16)	C14—C15—H15	119.00
C11—C10—C15	119.29 (18)	C16—C17—H17	120.00
C10—C11—C12	120.36 (16)	C18—C17—H17	120.00
C11—C12—C13	118.56 (17)	C17—C18—H18	119.00
N2—C13—C12	118.97 (17)	C19—C18—H18	119.00
N2—C13—C14	118.34 (16)	C19—C20—H20	120.00
C12—C13—C14	122.69 (18)	C21—C20—H20	120.00
C13—C14—C15	118.03 (17)	C16—C21—H21	119.00
C10—C15—C14	121.06 (17)	C20—C21—H21	119.00
N1—C16—C17	121.10 (16)	O5—C22—H22A	109.00
N1—C16—C21	120.06 (18)	O5—C22—H22B	109.00
C17—C16—C21	118.83 (18)	O5—C22—H22C	109.00
C16—C17—C18	119.84 (19)	H22A—C22—H22B	109.00
C17—C18—C19	121.2 (2)	H22A—C22—H22C	110.00
O5—C19—C18	116.24 (19)	H22B—C22—H22C	109.00
O5—C19—C20	124.65 (19)
C2—O2—C4—C5	177.80 (19)	C2—C3—C10—C15	115.35 (17)
C4—O2—C2—C1	−176.84 (16)	N1—C3—C10—C11	37.9 (2)
C4—O2—C2—C3	−81.0 (2)	C2—C3—C10—C11	−63.5 (2)
C2—O2—C4—C9	−1.7 (3)	O2—C4—C5—C6	−179.5 (2)
C22—O5—C19—C18	169.3 (2)	O2—C4—C9—C8	179.7 (2)
C22—O5—C19—C20	−12.1 (3)	C9—C4—C5—C6	0.0 (4)
C16—N1—C1—C2	169.0 (2)	C5—C4—C9—C8	0.2 (3)
C3—N1—C1—O1	−178.4 (2)	C4—C5—C6—C7	−0.2 (5)
C16—N1—C1—O1	−11.3 (4)	C5—C6—C7—C8	0.2 (5)
C1—N1—C16—C21	170.0 (2)	C6—C7—C8—C9	0.0 (5)
C16—N1—C3—C10	70.7 (2)	C7—C8—C9—C4	−0.2 (4)
C3—N1—C16—C21	−26.9 (3)	C3—C10—C11—C12	177.87 (15)
C16—N1—C3—C2	−169.53 (19)	C11—C10—C15—C14	1.2 (2)
C3—N1—C1—C2	1.90 (16)	C15—C10—C11—C12	−1.0 (2)
C1—N1—C3—C2	−1.84 (15)	C3—C10—C15—C14	−177.68 (15)
C3—N1—C16—C17	152.68 (19)	C10—C11—C12—C13	0.7 (3)
C1—N1—C16—C17	−10.4 (3)	C11—C12—C13—C14	−0.7 (3)
C1—N1—C3—C10	−121.65 (15)	C11—C12—C13—N2	−179.56 (16)
O4—N2—C13—C14	−7.7 (3)	N2—C13—C14—C15	179.77 (16)
O3—N2—C13—C14	172.35 (18)	C12—C13—C14—C15	0.9 (3)
O4—N2—C13—C12	171.23 (18)	C13—C14—C15—C10	−1.2 (3)
O3—N2—C13—C12	−8.8 (3)	N1—C16—C21—C20	−179.51 (18)
N1—C1—C2—O2	115.78 (16)	C17—C16—C21—C20	0.9 (3)
O1—C1—C2—C3	178.6 (3)	N1—C16—C17—C18	179.76 (18)
N1—C1—C2—C3	−1.78 (15)	C21—C16—C17—C18	−0.6 (3)
O1—C1—C2—O2	−63.9 (3)	C16—C17—C18—C19	0.0 (3)
O2—C2—C3—C10	10.4 (2)	C17—C18—C19—C20	0.4 (3)
O2—C2—C3—N1	−109.09 (17)	C17—C18—C19—O5	179.1 (2)
C1—C2—C3—C10	121.13 (17)	O5—C19—C20—C21	−178.7 (2)
C1—C2—C3—N1	1.66 (14)	C18—C19—C20—C21	−0.1 (3)
N1—C3—C10—C15	−143.22 (15)	C19—C20—C21—C16	−0.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1	0.93	2.60	3.172 (3)	120
C12—H12···O1i	0.93	2.37	3.103 (2)	135
C21—H21···O4ii	0.93	2.43	3.127 (3)	132
C15—H15···Cg4iii	0.93	2.75	3.674 (2)	173

Table 1

Hydrogen-bond geometry (, )

Cg4 is the centroid of the methoxyphenyl ring (C16C21).

DHA	DH	HA	D A	DHA
C17H17O1	0.93	2.60	3.172(3)	120
C12H12O1i	0.93	2.37	3.103(2)	135
C21H21O4ii	0.93	2.43	3.127(3)	132
C15H15Cg4iii	0.93	2.75	3.674(2)	173

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