(3R*,4R*)-1-(4-Chloro-phen-yl)-4-[2-hy-droxy-3-(morpholinomethyl)-phen-yl]-3-phen-oxy-azetidin-2-one.

The β-lactam ring of the title compound, C(26)H(25)ClN(2)O(4), is nearly planar (r.m.s. deviation = 0.025 Å) and the morpholine ring adopts a chair conformation. The mean plane of the β-lactam ring makes dihedral angles of 21.6 (4), 84.4 (4) and 33.7 (4)° with the two benzene rings and the phenyl ring, respectively. The conformation of the title compound is stabilized by intra-molecular C-H⋯O and O-H⋯N inter-actions. The crystal structure features C-H⋯π and aromatic π-π stacking inter-actions [centroid-centroid distances = 3.684 (4) and 3.883 (4) Å].

Related literature

For a related structure, see: Akkurt et al. (2011 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C26H25ClN2O4

M = 464.93

Monoclinic,

a = 29.6418 (18) Å

b = 6.7166 (3) Å

c = 28.5708 (15) Å

β = 123.043 (4)°

V = 4768.2 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.20 mm−1

T = 296 K

0.53 × 0.23 × 0.04 mm

Data collection

Stoe IPDS 2 diffractometer

Absorption correction: integration (X-RED32; Stoe & Cie, 2002 ▶) T min = 0.904, T max = 0.992

16824 measured reflections

4707 independent reflections

1712 reflections with I > 2σ(I)

R int = 0.159

Refinement

R[F 2 > 2σ(F 2)] = 0.087

wR(F 2) = 0.130

S = 1.00

4707 reflections

302 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.15 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/S1600536811000675/hb5782sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000675/hb5782Isup2.hkl

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

C26H25ClN2O4	F(000) = 1952
Mr = 464.93	Dx = 1.295 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9239 reflections
a = 29.6418 (18) Å	θ = 1.4–26.6°
b = 6.7166 (3) Å	µ = 0.20 mm−1
c = 28.5708 (15) Å	T = 296 K
β = 123.043 (4)°	Needle, colourless
V = 4768.2 (5) Å3	0.53 × 0.23 × 0.04 mm
Z = 8

Stoe IPDS 2 diffractometer	4707 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1712 reflections with I > 2σ(I)
plane graphite	Rint = 0.159
Detector resolution: 6.67 pixels mm-1	θmax = 26.2°, θmin = 1.6°
ω scans	h = −36→36
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→7
Tmin = 0.904, Tmax = 0.992	l = −34→32
16824 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)] = 0.087	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0198P)2] where P = (Fo2 + 2Fc2)/3
4707 reflections	(Δ/σ)max < 0.001
302 parameters	Δρmax = 0.15 e Å−3
1 restraint	Δρmin = −0.15 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
Cl1	0.55205 (8)	−0.0943 (3)	−0.11446 (7)	0.1225 (9)
O1	0.58355 (13)	0.2225 (4)	0.21000 (14)	0.0705 (15)
O2	0.53938 (15)	0.4640 (5)	0.09015 (15)	0.0921 (16)
O3	0.67681 (14)	0.3208 (4)	0.13843 (16)	0.0711 (15)
O4	0.7152 (2)	0.5197 (7)	0.0038 (2)	0.133 (3)
N1	0.57506 (14)	0.1426 (5)	0.09621 (17)	0.0565 (16)
N2	0.74627 (19)	0.3438 (6)	0.1079 (2)	0.080 (2)
C1	0.58006 (18)	0.3860 (7)	0.2379 (2)	0.064 (2)
C2	0.57298 (19)	0.5775 (7)	0.2178 (2)	0.073 (2)
C3	0.5692 (2)	0.7320 (7)	0.2476 (3)	0.085 (3)
C4	0.5719 (2)	0.6941 (8)	0.2963 (3)	0.097 (3)
C5	0.5791 (2)	0.5024 (9)	0.3163 (3)	0.103 (3)
C6	0.5825 (2)	0.3474 (7)	0.2858 (2)	0.082 (3)
C7	0.60357 (19)	0.2554 (6)	0.1756 (2)	0.059 (2)
C8	0.61155 (18)	0.0579 (6)	0.15272 (19)	0.0549 (17)
C9	0.5657 (2)	0.3163 (7)	0.1150 (2)	0.064 (2)
C10	0.56823 (18)	0.0872 (7)	0.0456 (2)	0.0600 (17)
C11	0.58087 (19)	−0.1071 (6)	0.0384 (2)	0.071 (2)
C12	0.5758 (2)	−0.1594 (7)	−0.0105 (2)	0.077 (2)
C13	0.5587 (2)	−0.0228 (9)	−0.0526 (2)	0.080 (2)
C14	0.5446 (2)	0.1665 (8)	−0.0465 (2)	0.077 (2)
C15	0.54974 (18)	0.2211 (7)	0.0022 (2)	0.067 (2)
C16	0.66644 (18)	0.0030 (6)	0.16733 (18)	0.0544 (16)
C17	0.69762 (19)	0.1335 (6)	0.15820 (19)	0.0580 (17)
C18	0.7471 (2)	0.0758 (8)	0.1678 (2)	0.067 (2)
C19	0.7664 (2)	−0.1138 (8)	0.1899 (2)	0.078 (2)
C20	0.7373 (2)	−0.2423 (8)	0.2011 (2)	0.077 (2)
C21	0.6879 (2)	−0.1842 (6)	0.18915 (19)	0.0653 (19)
C22	0.7803 (2)	0.2180 (8)	0.1572 (3)	0.093 (3)
C23	0.7780 (3)	0.5021 (9)	0.1032 (3)	0.117 (4)
C24	0.7411 (4)	0.6337 (10)	0.0543 (4)	0.145 (5)
C25	0.6841 (2)	0.3629 (9)	0.0067 (3)	0.111 (3)
C26	0.7192 (2)	0.2287 (7)	0.0555 (2)	0.088 (3)
H2	0.57070	0.60280	0.18450	0.0890*
H3	0.56490	0.86200	0.23460	0.1020*
H3A	0.6940 (18)	0.370 (7)	0.125 (2)	0.093 (19)*
H4	0.56880	0.79830	0.31580	0.1160*
H5	0.58170	0.47660	0.34970	0.1240*
H6	0.58640	0.21700	0.29830	0.0990*
H7	0.63640	0.33630	0.19450	0.0700*
H8	0.59450	−0.05380	0.15940	0.0650*
H11	0.59270	−0.20010	0.06690	0.0840*
H12	0.58390	−0.28860	−0.01530	0.0920*
H14	0.53160	0.25730	−0.07570	0.0920*
H15	0.54070	0.34970	0.00620	0.0810*
H19	0.79970	−0.15400	0.19720	0.0940*
H20	0.75100	−0.36680	0.21670	0.0920*
H21	0.66790	−0.27270	0.19580	0.0780*
H22A	0.80150	0.30230	0.18970	0.1110*
H22B	0.80490	0.14230	0.15170	0.1110*
H23A	0.80490	0.44350	0.09800	0.1410*
H23B	0.79640	0.58040	0.13720	0.1410*
H24A	0.71410	0.69200	0.05950	0.1730*
H24B	0.76160	0.74110	0.05180	0.1730*
H25A	0.66690	0.28600	−0.02760	0.1340*
H25B	0.65610	0.41960	0.01050	0.1340*
H26A	0.69750	0.12460	0.05720	0.1060*
H26B	0.74600	0.16630	0.05070	0.1060*

	U11	U22	U33	U12	U13	U23
Cl1	0.1695 (18)	0.1205 (13)	0.0933 (13)	0.0114 (11)	0.0819 (13)	−0.0060 (10)
O1	0.100 (3)	0.0508 (19)	0.086 (3)	−0.0019 (17)	0.067 (2)	0.0026 (17)
O2	0.115 (3)	0.070 (2)	0.091 (3)	0.038 (2)	0.056 (2)	0.023 (2)
O3	0.089 (3)	0.0445 (18)	0.106 (3)	−0.0007 (17)	0.070 (2)	0.0045 (17)
O4	0.208 (5)	0.098 (3)	0.168 (5)	−0.024 (3)	0.150 (5)	0.006 (3)
N1	0.061 (3)	0.050 (2)	0.059 (3)	0.0081 (19)	0.033 (2)	0.006 (2)
N2	0.103 (4)	0.060 (3)	0.113 (4)	−0.023 (3)	0.083 (3)	−0.021 (3)
C1	0.067 (4)	0.059 (3)	0.084 (4)	−0.003 (2)	0.052 (3)	0.001 (3)
C2	0.088 (4)	0.060 (3)	0.092 (4)	0.001 (3)	0.062 (4)	0.007 (3)
C3	0.105 (5)	0.058 (3)	0.124 (5)	0.003 (3)	0.083 (4)	0.003 (3)
C4	0.118 (5)	0.076 (4)	0.140 (6)	−0.001 (4)	0.098 (5)	−0.017 (4)
C5	0.145 (6)	0.089 (4)	0.126 (6)	−0.001 (4)	0.107 (5)	−0.003 (4)
C6	0.117 (5)	0.062 (3)	0.107 (5)	−0.003 (3)	0.086 (4)	0.003 (3)
C7	0.074 (4)	0.051 (3)	0.067 (4)	−0.001 (2)	0.049 (3)	0.003 (2)
C8	0.060 (3)	0.044 (3)	0.064 (3)	−0.005 (2)	0.036 (3)	0.002 (2)
C9	0.066 (4)	0.058 (3)	0.072 (4)	0.004 (3)	0.041 (3)	0.010 (3)
C10	0.056 (3)	0.057 (3)	0.062 (3)	−0.002 (2)	0.029 (3)	0.005 (3)
C11	0.083 (4)	0.048 (3)	0.067 (4)	−0.001 (3)	0.032 (3)	0.000 (3)
C12	0.090 (4)	0.063 (3)	0.072 (4)	0.008 (3)	0.040 (4)	−0.009 (3)
C13	0.091 (4)	0.089 (4)	0.060 (4)	0.002 (3)	0.042 (4)	−0.004 (3)
C14	0.084 (4)	0.077 (4)	0.069 (4)	0.011 (3)	0.041 (3)	0.015 (3)
C15	0.073 (4)	0.064 (3)	0.070 (4)	0.014 (3)	0.042 (3)	0.005 (3)
C16	0.063 (3)	0.041 (2)	0.060 (3)	0.001 (2)	0.034 (3)	−0.001 (2)
C17	0.063 (3)	0.046 (3)	0.065 (3)	0.007 (2)	0.035 (3)	−0.002 (2)
C18	0.057 (4)	0.073 (3)	0.074 (4)	−0.001 (3)	0.037 (3)	−0.009 (3)
C19	0.067 (4)	0.081 (4)	0.069 (4)	0.019 (3)	0.026 (3)	−0.009 (3)
C20	0.079 (4)	0.063 (3)	0.069 (4)	0.017 (3)	0.027 (3)	0.011 (3)
C21	0.066 (4)	0.053 (3)	0.065 (3)	0.007 (3)	0.028 (3)	0.008 (2)
C22	0.084 (5)	0.093 (4)	0.118 (5)	−0.009 (4)	0.066 (4)	−0.010 (4)
C23	0.165 (7)	0.083 (4)	0.173 (7)	−0.048 (5)	0.137 (6)	−0.041 (5)
C24	0.250 (10)	0.069 (4)	0.208 (10)	−0.038 (5)	0.185 (9)	−0.017 (5)
C25	0.139 (6)	0.100 (5)	0.124 (6)	−0.009 (4)	0.091 (5)	0.015 (4)
C26	0.108 (5)	0.068 (3)	0.115 (5)	−0.014 (3)	0.078 (4)	−0.012 (4)

Cl1—C13	1.736 (6)	C17—C18	1.392 (9)
O1—C1	1.394 (6)	C18—C22	1.516 (9)
O1—C7	1.415 (7)	C18—C19	1.398 (8)
O2—C9	1.222 (6)	C19—C20	1.376 (9)
O3—C17	1.379 (5)	C20—C21	1.367 (9)
O4—C24	1.432 (10)	C23—C24	1.504 (11)
O4—C25	1.432 (9)	C25—C26	1.502 (8)
O3—H3A	0.85 (6)	C2—H2	0.9300
N1—C9	1.374 (6)	C3—H3	0.9300
N1—C10	1.397 (7)	C4—H4	0.9300
N1—C8	1.482 (6)	C5—H5	0.9300
N2—C22	1.472 (8)	C6—H6	0.9300
N2—C23	1.473 (10)	C7—H7	0.9800
N2—C26	1.474 (7)	C8—H8	0.9800
C1—C2	1.377 (7)	C11—H11	0.9300
C1—C6	1.356 (7)	C12—H12	0.9300
C2—C3	1.385 (8)	C14—H14	0.9300
C3—C4	1.373 (10)	C15—H15	0.9300
C4—C5	1.377 (8)	C19—H19	0.9300
C5—C6	1.396 (8)	C20—H20	0.9300
C7—C9	1.518 (7)	C21—H21	0.9300
C7—C8	1.553 (6)	C22—H22A	0.9700
C8—C16	1.489 (8)	C22—H22B	0.9700
C10—C15	1.380 (7)	C23—H23A	0.9700
C10—C11	1.404 (7)	C23—H23B	0.9700
C11—C12	1.367 (7)	C24—H24A	0.9700
C12—C13	1.371 (7)	C24—H24B	0.9700
C13—C14	1.379 (8)	C25—H25A	0.9700
C14—C15	1.365 (7)	C25—H25B	0.9700
C16—C17	1.398 (8)	C26—H26A	0.9700
C16—C21	1.394 (6)	C26—H26B	0.9700
C1—O1—C7	117.7 (4)	C3—C2—H2	120.00
C24—O4—C25	110.1 (6)	C2—C3—H3	120.00
C17—O3—H3A	107 (3)	C4—C3—H3	120.00
C8—N1—C9	94.8 (4)	C3—C4—H4	120.00
C9—N1—C10	133.2 (4)	C5—C4—H4	120.00
C8—N1—C10	129.3 (4)	C4—C5—H5	120.00
C22—N2—C23	111.3 (5)	C6—C5—H5	120.00
C23—N2—C26	107.9 (5)	C1—C6—H6	120.00
C22—N2—C26	112.4 (4)	C5—C6—H6	120.00
O1—C1—C6	116.6 (4)	O1—C7—H7	112.00
C2—C1—C6	120.8 (5)	C8—C7—H7	112.00
O1—C1—C2	122.6 (5)	C9—C7—H7	112.00
C1—C2—C3	119.2 (5)	N1—C8—H8	111.00
C2—C3—C4	120.3 (5)	C7—C8—H8	111.00
C3—C4—C5	120.3 (6)	C16—C8—H8	111.00
C4—C5—C6	119.1 (6)	C10—C11—H11	120.00
C1—C6—C5	120.4 (5)	C12—C11—H11	120.00
O1—C7—C8	112.1 (4)	C11—C12—H12	120.00
O1—C7—C9	120.3 (5)	C13—C12—H12	120.00
C8—C7—C9	86.4 (4)	C13—C14—H14	120.00
N1—C8—C7	86.7 (3)	C15—C14—H14	120.00
N1—C8—C16	115.9 (4)	C10—C15—H15	120.00
C7—C8—C16	119.2 (4)	C14—C15—H15	120.00
O2—C9—C7	136.2 (5)	C18—C19—H19	119.00
N1—C9—C7	92.0 (4)	C20—C19—H19	119.00
O2—C9—N1	131.6 (5)	C19—C20—H20	121.00
N1—C10—C11	120.0 (4)	C21—C20—H20	120.00
N1—C10—C15	121.3 (4)	C16—C21—H21	119.00
C11—C10—C15	118.8 (5)	C20—C21—H21	119.00
C10—C11—C12	120.0 (4)	N2—C22—H22A	109.00
C11—C12—C13	120.4 (5)	N2—C22—H22B	109.00
Cl1—C13—C14	120.7 (4)	C18—C22—H22A	109.00
C12—C13—C14	119.9 (5)	C18—C22—H22B	109.00
Cl1—C13—C12	119.4 (5)	H22A—C22—H22B	108.00
C13—C14—C15	120.2 (5)	N2—C23—H23A	110.00
C10—C15—C14	120.6 (5)	N2—C23—H23B	110.00
C8—C16—C17	121.7 (4)	C24—C23—H23A	110.00
C8—C16—C21	120.8 (5)	C24—C23—H23B	110.00
C17—C16—C21	117.5 (5)	H23A—C23—H23B	108.00
O3—C17—C18	121.5 (5)	O4—C24—H24A	110.00
C16—C17—C18	121.4 (4)	O4—C24—H24B	110.00
O3—C17—C16	117.1 (5)	C23—C24—H24A	110.00
C17—C18—C19	118.1 (5)	C23—C24—H24B	110.00
C19—C18—C22	120.9 (6)	H24A—C24—H24B	108.00
C17—C18—C22	121.0 (5)	O4—C25—H25A	109.00
C18—C19—C20	121.5 (6)	O4—C25—H25B	110.00
C19—C20—C21	119.0 (5)	C26—C25—H25A	110.00
C16—C21—C20	122.3 (5)	C26—C25—H25B	109.00
N2—C22—C18	111.9 (6)	H25A—C25—H25B	108.00
N2—C23—C24	109.4 (7)	N2—C26—H26A	110.00
O4—C24—C23	109.9 (6)	N2—C26—H26B	110.00
O4—C25—C26	110.7 (6)	C25—C26—H26A	110.00
N2—C26—C25	110.2 (4)	C25—C26—H26B	109.00
C1—C2—H2	120.00	H26A—C26—H26B	108.00
C7—O1—C1—C2	27.8 (8)	O1—C7—C9—N1	−115.5 (4)
C7—O1—C1—C6	−153.9 (5)	C9—C7—C8—C16	119.7 (5)
C1—O1—C7—C8	173.3 (4)	C8—C7—C9—N1	−1.9 (4)
C1—O1—C7—C9	−87.5 (5)	C9—C7—C8—N1	1.7 (4)
C24—O4—C25—C26	−58.8 (8)	C7—C8—C16—C21	128.8 (5)
C25—O4—C24—C23	60.3 (11)	N1—C8—C16—C21	−129.8 (4)
C10—N1—C8—C7	161.0 (5)	N1—C8—C16—C17	48.2 (6)
C9—N1—C8—C16	−122.9 (4)	C7—C8—C16—C17	−53.2 (6)
C9—N1—C10—C11	−178.9 (6)	N1—C10—C15—C14	178.3 (6)
C10—N1—C9—C7	−159.8 (6)	N1—C10—C11—C12	−177.9 (6)
C8—N1—C10—C15	−154.4 (5)	C15—C10—C11—C12	1.3 (9)
C10—N1—C8—C16	40.0 (7)	C11—C10—C15—C14	−1.0 (9)
C8—N1—C9—C7	2.0 (5)	C10—C11—C12—C13	0.4 (9)
C8—N1—C9—O2	177.5 (7)	C11—C12—C13—Cl1	−179.4 (5)
C10—N1—C9—O2	15.7 (12)	C11—C12—C13—C14	−2.4 (10)
C9—N1—C10—C15	1.9 (10)	C12—C13—C14—C15	2.8 (10)
C8—N1—C10—C11	24.8 (9)	Cl1—C13—C14—C15	179.7 (5)
C9—N1—C8—C7	−1.9 (5)	C13—C14—C15—C10	−1.1 (9)
C23—N2—C26—C25	−58.2 (7)	C17—C16—C21—C20	−0.5 (7)
C22—N2—C23—C24	−176.7 (6)	C21—C16—C17—C18	3.2 (7)
C26—N2—C22—C18	−68.0 (7)	C8—C16—C17—O3	4.2 (6)
C26—N2—C23—C24	59.6 (8)	C21—C16—C17—O3	−177.8 (4)
C22—N2—C26—C25	178.7 (6)	C8—C16—C21—C20	177.5 (4)
C23—N2—C22—C18	171.0 (5)	C8—C16—C17—C18	−174.9 (4)
O1—C1—C6—C5	−179.8 (6)	C16—C17—C18—C19	−3.5 (7)
C6—C1—C2—C3	1.0 (9)	O3—C17—C18—C22	0.4 (7)
O1—C1—C2—C3	179.2 (6)	O3—C17—C18—C19	177.6 (4)
C2—C1—C6—C5	−1.5 (9)	C16—C17—C18—C22	179.4 (5)
C1—C2—C3—C4	−0.7 (10)	C19—C18—C22—N2	146.3 (5)
C2—C3—C4—C5	0.9 (11)	C17—C18—C22—N2	−36.7 (7)
C3—C4—C5—C6	−1.3 (11)	C22—C18—C19—C20	178.3 (5)
C4—C5—C6—C1	1.6 (10)	C17—C18—C19—C20	1.1 (7)
O1—C7—C9—O2	69.3 (9)	C18—C19—C20—C21	1.4 (7)
O1—C7—C8—N1	123.1 (4)	C19—C20—C21—C16	−1.7 (7)
C8—C7—C9—O2	−177.1 (8)	N2—C23—C24—O4	−61.4 (11)
O1—C7—C8—C16	−118.9 (5)	O4—C25—C26—N2	58.4 (7)

Cg5 is a centroid of the C16–C21 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N2	0.85 (6)	1.87 (6)	2.642 (8)	150 (5)
C2—H2···O2	0.93	2.50	3.304 (6)	144
C15—H15···O2	0.93	2.54	3.148 (7)	123
C20—H20···Cg5i	0.93	2.88	3.596 (5)	134

	Ring-2	Ring-3	Ring-4
Ring-1	33.7 (4)	21.6 (4)	84.4 (4)
Ring-2		13.0 (3)	63.0 (3)
Ring-3			67.6 (3)

Table 1

Hydrogen-bond geometry (Å, °)

Cg5 is a centroid of the C16–C21 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N2	0.85 (6)	1.87 (6)	2.642 (8)	150 (5)
C2—H2⋯O2	0.93	2.50	3.304 (6)	144
C15—H15⋯O2	0.93	2.54	3.148 (7)	123
C20—H20⋯Cg5i	0.93	2.88	3.596 (5)	134

Symmetry code: (i) .