(3R*,4R*)-1-(4-Chloro­phen­yl)-4-[2-hy­droxy-3-(morpholinomethyl)­phen­yl]-3-phen­oxy­azetidin-2-one

Akkurt, M.; Jarrahpour, A.; Sharghi, H.; Badrabady, S.A.T.; Büyükgüngör, O.

doi:10.1107/S1600536811000675

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o325

doi:10.1107/S1600536811000675

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(3R,4R)-1-(4-Chlorophenyl)-4-[2-hydroxy-3-(morpholinomethyl)phenyl]-3-phenoxyazetidin-2-one

Mehmet Akkurt,^a ^* Aliasghar Jarrahpour,^b Hashem Sharghi,^b Seid Ali Torabi Badrabady ^b and Orhan Büyükgüngör ^c

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bDepartment of Chemistry, College of Sciences, Shiraz University, 71454 Shiraz, Iran, and ^cDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayıs University, 55139 Samsun, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 21 December 2010; accepted 5 January 2011; online 12 January 2011)

The β-lactam ring of the title compound, C₂₆H₂₅ClN₂O₄, 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 intramolecular C—H⋯O and O—H⋯N interactions. The crystal structure features C—H⋯π and aromatic π–π stacking interactions [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_r = 464.93
Monoclinic, C 2/c
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[F² > 2σ(F²)] = 0.087
wR(F²) = 0.130
S = 1.00
4707 reflections
302 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 e Å⁻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) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811000675/hb5782sup1.cif

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

checkCIF report

Comment top

As part of our ongoing structural studies of β-lactams (Akkurt et al., 2011), we now report the structure of the title compound, (I).

In the title compound, (I), (Fig. 1), the β-lactam ring (N1/C7–C9) is almost planar, with long C—C distances [C7–C9 = 1.518 (7) Å and C7–C8 = 1.553 (6) Å]. The morpholine ring (N2/O4/C23—C26) adopts a chair conformation, with the puckering parameters of Q_T = 0.594 (8) Å, θ = 177.1 (8)° and ϕ = 305 (17)° (Cremer & Pople, 1975). The dihedral angles between the mean planes of the rings in (I) are given in Table 2.

The molecular conformation of (I) is stabilized by intra-molecular C— H···O and O— H···N interactions (Table 1). The crystal structure is stabilized by C—H&ctdot;π interactions (Table 1) and two π-π stacking interactions [Cg1···Cg5(x, y, z) = 3.684 (4) Å and Cg4···Cg4(1 - x, -y, -z) = 3.883 (4) Å, where Cg1, Cg4 and Cg5 are the centroids of the N1/C7–C9 β-lactam, the C10–C15 and C16–C21 benzene rings, respectively]. Fig. 2 shows the packing of (I), down the b axis.

Related literature top

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

Experimental top

To a solution of (E)-2-((4-chlorophenylimino)methyl)-6-(morpholinomethyl)phenol (1.0 mmol) and triethylamine (2.6 mmol) in dry CH₂Cl₂ was slowly added phenoxyacetyl chloride (1.3 mmol) in dry CH₂Cl₂ (10 ml) at 195 K. The reaction mixture was then allowed to warm to room temperature, stirred over night and then it was washed with saturated sodium bicarbonate solution (20 ml), brine (20 ml), dried (Na₂SO₄). The solvent was evaporated under reduced pressure to give the crude product which was then purified by column chromatography over silica gel. Colourless needles were recrystallised from ethyl acetate (yield 65%). [mp: 463–465 K]. IR (KBr, cm^-1): 1758.5 (CO β-Lactam), 3311–3497 (OH). ¹H-NMR (250 MHz, CDCl₃) δ (p.p.m): 3.43 (CH₂—N, t, 4H, J = 13.5 Hz), 3.70 (CH₂, s, 2H), 3.88 (CH₂—O, t, 4H, J = 13.9 Hz), 5.59 (H-8, d, 1H, J = 1.6 Hz), 5.91 (H-7, d, 1H, J = 1.6 Hz), 6.67–7.35 (ArH, m, 12H); ¹³C-NMR (62.9 MHz, CDCl₃) δ (p.p.m): 52.6 (CH₂—N), 55.9 (C-22), 50.2 (O—CH₂), 66.5 (C-8), 80.9 (C-7), 115.2–157.0 (aromatic carbons), 163.1 (CO β-Lactam). Analysis calculated for C₂₆H₂₅ClN₂O₄: C 67.17, H 5.42, N 6.03%. found: C 67.05, H 5.47, N 6.08%.

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: 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).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids for non-H atoms drawn at the 20% probability level.
	Fig. 2. The packing of (I), viewing down the b axis. All H atoms are omitted for clarity.

(3R*,4R*)-1-(4-Chlorophenyl)-4-[2-hydroxy-3- (morpholinomethyl)phenyl]-3-phenoxyazetidin-2-one top

Crystal data top

C₂₆H₂₅ClN₂O₄	F(000) = 1952
M_r = 464.93	D_x = 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

Data collection top

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 monochromator	R_int = 0.159
Detector resolution: 6.67 pixels mm^-1	θ_max = 26.2°, θ_min = 1.6°
ω scans	h = −36→36
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −8→7
T_min = 0.904, T_max = 0.992	l = −34→32
16824 measured reflections

Refinement top

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(F_o²) + (0.0198P)²] where P = (F_o² + 2F_c²)/3
4707 reflections	(Δ/σ)_max < 0.001
302 parameters	Δρ_max = 0.15 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₂₆H₂₅ClN₂O₄	V = 4768.2 (5) Å³
M_r = 464.93	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 29.6418 (18) Å	µ = 0.20 mm⁻¹
b = 6.7166 (3) Å	T = 296 K
c = 28.5708 (15) Å	0.53 × 0.23 × 0.04 mm
β = 123.043 (4)°

Data collection top

Stoe IPDS 2 diffractometer	4707 independent reflections
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	1712 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.992	R_int = 0.159
16824 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.087	1 restraint
wR(F²) = 0.130	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.15 e Å⁻³
4707 reflections	Δρ_min = −0.15 e Å⁻³
302 parameters

Special details top

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	0.55205 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₆H₂₅ClN₂O₄
M_r	464.93
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	29.6418 (18), 6.7166 (3), 28.5708 (15)
β (°)	123.043 (4)
V (Å³)	4768.2 (5)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.53 × 0.23 × 0.04

Data collection
Diffractometer	Stoe IPDS 2 diffractometer
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002)
T_min, T_max	0.904, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	16824, 4707, 1712
R_int	0.159
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.087, 0.130, 1.00
No. of reflections	4707
No. of parameters	302
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

Computer programs: X-AREA (Stoe & Cie, 2002), X-RED32 (Stoe & Cie, 2002), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+1/2.

The dihedral angles between the mean planes of the rings in (I) (°) top

	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)

Ring-1 : N1/C7–C9 β-lactam ring, Ring-2 : C1–C6 phenyl ring, Ring-3 : C10–C15 benzene ring, Ring-4 : C16–C21 benzene ring.

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, HS, SATB and MA thank the Shiraz University Research Council for financial support (grant No. 89-GR—SC-23).

References

Akkurt, M., Dağdemir, Y., Jarrahpour, A., Rostami, M. & Büyükgüngör, O. (2011). Acta Cryst. E67, o326–o327. Web of Science CSD CrossRef IUCr Journals Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany. Google Scholar

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Volume 67| Part 2| February 2011| Page o325

doi:10.1107/S1600536811000675

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

(3R*,4R*)-1-(4-Chloro­phen­yl)-4-[2-hy­dr­oxy-3-(morpholino­methyl)­phen­yl]-3-phen­­oxy­azetidin-2-one

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(3R,4R)-1-(4-Chlorophenyl)-4-[2-hydroxy-3-(morpholinomethyl)phenyl]-3-phenoxyazetidin-2-one