(RS/SR)-2-Oxo-4-phenyl­azetidin-3-yl acetate

Li, Y.

doi:10.1107/S1600536809038860

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2590

doi:10.1107/S1600536809038860

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(RS/SR)-2-Oxo-4-phenylazetidin-3-yl acetate

Yangjun Li ^a ^*

^aSchool of Information and Communication Engineering, North University of China, Taiyuan 030051, People's Republic of China
^*Correspondence e-mail: liyangjun2010@126.com

(Received 23 September 2009; accepted 25 September 2009; online 30 September 2009)

In the title compound, C₁₁H₁₁NO₃, a modified synthetic acetate derivative, the four memebered β-lactam ring is roughly planar, with a maximum deviation of 0.21 (3) Å, and makes a dihedral angle of 81.46 (14)° with the phenyl ring. In the crystal, a single N—H⋯O hydrogen bond links molecules into a chain parallel to the a axis and thus stabilizes the structure. Although the absolute configuration could not be reliably determined, the compound corresponds to the diasteroisomer (RS/SR)

Related literature

For properties of lactams, see: Selvanayagam et al. (2005 ); Deschamps et al. (2003 ); Kanazawa et al. (1993 ). For a related structure, see: Akkurt et al. (2007 ).

Experimental

Crystal data

C₁₁H₁₁NO₃
M_r = 205.21
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.940 (4) Å
b = 8.198 (4) Å
c = 20.896 (13) Å
V = 1017.6 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.21 × 0.16 × 0.10 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.980, T_max = 0.990
1899 measured reflections
1126 independent reflections
853 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.125
S = 1.17
1126 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1ⁱ	0.86	2.11	2.943 (3)	162
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+2]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT ; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038860/dn2490sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809038860/dn2490Isup2.hkl

checkCIF report

Comment top

Recently, lactams have attracted much attention because they are convenient intermediates for semi-synthesis of the antitumour drug Taxol and other bioactive analogues (Kanazawa et al., 1993). Furthermore, the lactam ring (azetidin-2-one) is considered a general 'lead structure' for the design of new inhibitors of enzymes containing a serine nucleophile in the active site (Deschamps et al., 2003). In an attempt to form a Zn(II) complex with title compound, we adventitiously formed the title compound (I) and its crystal structure is determined herein.

The molecular structure of (I) is illustrated in Fig. 1. It is very similar to the related 4-(4-Nitrophenyl)-3-phenoxyazetidin-2-one (Akkurt et al., 2007). The geometry of the β-lactam ring is is planar, with a maximum deviation of 0.21 (3)° for atom N1. It makes dihedral angles of 81.46 (14)° with its phenyl substituent. The lactam ting is also comparable with a related reported structure (Selvanayagam et al., 2005). Although the absolute configuration couldn't be reliably determined, the compound correspond to the diasteroisomer (RS/SR).

Intermolecular N-H···O hydrogen bonds form a zig-zag like chain parallel to the a axis and thus stabilize the structure. (Table 1, Figure 2).

Related literature top

For properties of lactams, see: Selvanayagam et al. (2005); Deschamps et al. (2003); Kanazawa et al. (1993). For a related structure, see: Akkurt et al. (2007).

Experimental top

The title compound was obtained by direct mixing of equimolar (28mg, 0.1mmol) Zn(OAC)₂.6H₂O of water solution (8mL) and 2-Oxo-4-phenylazetidin-3-yl acetate (21mg, 0.1mmol), and CH₃CN and CH₃CH₂OH solutions (5mL). using slow evaporation of the solvent at room temperature over a period of about two weeks.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular view of (I) with the atom-labeling scheme. Ellipsoids are drawn at the the 30% probability level. H atoms are shown as spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the formation of the chain parallel to the a axis. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry code: (i) x-1/2, -y+5/2, -z+2]

(RS/SR)-2-Oxo-4-phenylazetidin-3-yl acetate top

Crystal data top

C₁₁H₁₁NO₃	F(000) = 432
M_r = 205.21	D_x = 1.340 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1899 reflections
a = 5.940 (4) Å	θ = 2.0–25.5°
b = 8.198 (4) Å	µ = 0.10 mm⁻¹
c = 20.896 (13) Å	T = 298 K
V = 1017.6 (11) Å³	Block, colorless
Z = 4	0.21 × 0.16 × 0.10 mm

Data collection top

Bruker APEXII area-detector diffractometer	1126 independent reflections
Radiation source: fine-focus sealed tube	853 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 25.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −7→7
T_min = 0.980, T_max = 0.990	k = 0→9
1899 measured reflections	l = −25→0

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.125	H-atom parameters constrained
S = 1.17	w = 1/[σ²(F_o²) + (0.0728P)²] where P = (F_o² + 2F_c²)/3
1126 reflections	(Δ/σ)_max = 0.001
137 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₁H₁₁NO₃	V = 1017.6 (11) Å³
M_r = 205.21	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.940 (4) Å	µ = 0.10 mm⁻¹
b = 8.198 (4) Å	T = 298 K
c = 20.896 (13) Å	0.21 × 0.16 × 0.10 mm

Data collection top

Bruker APEXII area-detector diffractometer	1126 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	853 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.990	R_int = 0.027
1899 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.17	Δρ_max = 0.17 e Å⁻³
1126 reflections	Δρ_min = −0.19 e Å⁻³
137 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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
C1	0.6268 (6)	0.7783 (4)	0.93447 (16)	0.0536 (9)
H1	0.7589	0.8249	0.9498	0.064*
C2	0.5969 (7)	0.6098 (4)	0.93779 (16)	0.0598 (10)
H2	0.7093	0.5443	0.9551	0.072*
C3	0.4038 (7)	0.5413 (4)	0.91576 (16)	0.0613 (10)
H3	0.3853	0.4288	0.9176	0.074*
C4	0.2362 (7)	0.6368 (4)	0.89092 (16)	0.0624 (10)
H4	0.1036	0.5894	0.8763	0.075*
C5	0.2647 (6)	0.8040 (4)	0.88758 (14)	0.0543 (9)
H5	0.1502	0.8688	0.8710	0.065*
C6	0.4617 (5)	0.8759 (4)	0.90866 (13)	0.0412 (7)
C7	0.4897 (6)	1.0577 (3)	0.90075 (14)	0.0449 (7)
H7	0.3451	1.1122	0.8935	0.054*
C8	0.7926 (6)	1.1852 (3)	0.91243 (13)	0.0434 (7)
C9	0.6733 (5)	1.1182 (3)	0.85319 (13)	0.0418 (7)
H9	0.6188	1.2043	0.8246	0.050*
C10	0.7031 (7)	0.9236 (4)	0.77046 (14)	0.0523 (9)
C11	0.8572 (7)	0.7982 (4)	0.74195 (15)	0.0747 (12)
H11A	0.8191	0.6924	0.7584	0.112*
H11B	1.0101	0.8237	0.7530	0.112*
H11C	0.8409	0.7984	0.6962	0.112*
N1	0.6232 (5)	1.1404 (3)	0.95028 (11)	0.0480 (7)
H1A	0.5996	1.1550	0.9905	0.058*
O1	0.9694 (4)	1.2566 (3)	0.92206 (9)	0.0555 (6)
O2	0.8050 (4)	0.9987 (2)	0.82088 (8)	0.0468 (6)
O3	0.5181 (5)	0.9564 (3)	0.75310 (12)	0.0712 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.048 (2)	0.0518 (18)	0.0607 (19)	0.0040 (16)	−0.0083 (17)	−0.0020 (16)
C2	0.067 (3)	0.0467 (18)	0.065 (2)	0.0129 (18)	−0.001 (2)	0.0082 (16)
C3	0.072 (3)	0.0455 (17)	0.066 (2)	−0.0057 (19)	0.009 (2)	−0.0021 (16)
C4	0.057 (2)	0.0561 (19)	0.074 (2)	−0.0084 (18)	−0.003 (2)	−0.0076 (17)
C5	0.050 (2)	0.0534 (18)	0.0593 (19)	0.0017 (17)	−0.0051 (17)	−0.0001 (15)
C6	0.0416 (19)	0.0429 (14)	0.0391 (14)	0.0017 (15)	0.0034 (14)	−0.0025 (12)
C7	0.0427 (19)	0.0433 (15)	0.0486 (15)	0.0005 (15)	0.0000 (15)	−0.0026 (12)
C8	0.049 (2)	0.0366 (14)	0.0448 (16)	0.0036 (15)	−0.0017 (16)	−0.0025 (12)
C9	0.0434 (19)	0.0418 (13)	0.0403 (14)	0.0038 (15)	−0.0018 (14)	−0.0026 (13)
C10	0.061 (2)	0.0573 (18)	0.0385 (15)	−0.0031 (18)	−0.0030 (16)	−0.0029 (13)
C11	0.073 (3)	0.083 (2)	0.068 (2)	0.009 (2)	−0.002 (2)	−0.030 (2)
N1	0.0590 (18)	0.0466 (13)	0.0383 (12)	−0.0024 (13)	0.0040 (13)	−0.0064 (11)
O1	0.0506 (15)	0.0620 (13)	0.0540 (12)	−0.0106 (12)	−0.0019 (11)	−0.0112 (10)
O2	0.0450 (13)	0.0540 (11)	0.0415 (11)	0.0019 (12)	−0.0005 (9)	−0.0109 (9)
O3	0.0721 (18)	0.0842 (16)	0.0572 (12)	0.0093 (16)	−0.0186 (13)	−0.0125 (12)

Geometric parameters (Å, º) top

C1—C6	1.376 (4)	C7—H7	0.9800
C1—C2	1.395 (4)	C8—O1	1.219 (4)
C1—H1	0.9300	C8—N1	1.332 (4)
C2—C3	1.357 (5)	C8—C9	1.529 (4)
C2—H2	0.9300	C9—O2	1.424 (3)
C3—C4	1.369 (5)	C9—H9	0.9800
C3—H3	0.9300	C10—O3	1.188 (4)
C4—C5	1.383 (4)	C10—O2	1.362 (4)
C4—H4	0.9300	C10—C11	1.500 (5)
C5—C6	1.382 (4)	C11—H11A	0.9600
C5—H5	0.9300	C11—H11B	0.9600
C6—C7	1.509 (4)	C11—H11C	0.9600
C7—N1	1.469 (4)	N1—H1A	0.8600
C7—C9	1.556 (4)

C6—C1—C2	120.3 (4)	C9—C7—H7	111.8
C6—C1—H1	119.8	O1—C8—N1	133.3 (3)
C2—C1—H1	119.8	O1—C8—C9	134.9 (3)
C3—C2—C1	120.0 (4)	N1—C8—C9	91.8 (2)
C3—C2—H2	120.0	O2—C9—C8	112.1 (2)
C1—C2—H2	120.0	O2—C9—C7	117.9 (2)
C2—C3—C4	120.4 (3)	C8—C9—C7	85.5 (2)
C2—C3—H3	119.8	O2—C9—H9	112.8
C4—C3—H3	119.8	C8—C9—H9	112.8
C3—C4—C5	119.8 (4)	C7—C9—H9	112.8
C3—C4—H4	120.1	O3—C10—O2	123.0 (3)
C5—C4—H4	120.1	O3—C10—C11	126.7 (3)
C6—C5—C4	120.7 (3)	O2—C10—C11	110.2 (3)
C6—C5—H5	119.7	C10—C11—H11A	109.5
C4—C5—H5	119.7	C10—C11—H11B	109.5
C1—C6—C5	118.7 (3)	H11A—C11—H11B	109.5
C1—C6—C7	122.6 (3)	C10—C11—H11C	109.5
C5—C6—C7	118.7 (3)	H11A—C11—H11C	109.5
N1—C7—C6	116.0 (3)	H11B—C11—H11C	109.5
N1—C7—C9	85.7 (2)	C8—N1—C7	96.7 (2)
C6—C7—C9	117.5 (2)	C8—N1—H1A	131.6
N1—C7—H7	111.8	C7—N1—H1A	131.6
C6—C7—H7	111.8	C10—O2—C9	115.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.11	2.943 (3)	162

Symmetry code: (i) x−1/2, −y+5/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₁NO₃
M_r	205.21
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	5.940 (4), 8.198 (4), 20.896 (13)
V (Å³)	1017.6 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.21 × 0.16 × 0.10

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.980, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	1899, 1126, 853
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.125, 1.17
No. of reflections	1126
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1ⁱ	0.86	2.11	2.943 (3)	162.3

Symmetry code: (i) x−1/2, −y+5/2, −z+2.

Acknowledgements

The author is grateful for funding from the Natural Science Foundation of Shanxi Province (2007011033), the Program of Technological Industrialization in Universities of Shanxi Province (20070308) and the Start-up Fund of the Northern University of China.

References

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