4-(4-Ethoxy­benz­yl)-1,3-oxazolidin-2-one

Wang, H.-Y.; Xie, M.-H.; Luo, S.-N.; He, Y.-J.; Zou, P.

doi:10.1107/S160053680900957X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o805

doi:10.1107/S160053680900957X

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4-(4-Ethoxybenzyl)-1,3-oxazolidin-2-one

Hong-Yong Wang,^a Min-Hao Xie,^a ^* Shi-Neng Luo,^a Yong-Jun He ^a and Pei Zou ^a

^aJiangsu Institute of Nuclear Medicine, Wuxi 214063, People's Republic of China
^*Correspondence e-mail: wywhy007@yahoo.com.cn

(Received 2 March 2009; accepted 16 March 2009; online 19 March 2009)

In the title compound, C₁₂H₁₅NO₃, the ethoxybenzyl ring plane forms a dihedral angle of 60.3 (4)° with the mean plane of the oxazolidine ring. The molecules are linked through N—H⋯O hydrogen bonds into a chain running in the b direction.

Related literature

For background literature, see: Chrzanowska & Rozwadowska (2004 ); Rozwadowska (1994 ); Scott & Williams (2002 ); Tussetschläger et al. (2007 ).

Experimental

Crystal data

C₁₂H₁₅NO₃
M_r = 221.25
Orthorhombic, P 2₁ 2₁ 2₁
a = 5.7960 (12) Å
b = 9.924 (2) Å
c = 20.209 (4) Å
V = 1162.4 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989 ) T_min = 0.973, T_max = 0.991
2427 measured reflections
1246 independent reflections
904 reflections with I > 2σ(I)
R_int = 0.043
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.150
S = 1.01
1246 reflections
146 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
N—H0A⋯O3ⁱ	0.86	1.99	2.845 (4)	171
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+2]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680900957X/pv2144sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900957X/pv2144Isup2.hkl

checkCIF report

Comment top

Tetrahydroisoquinoline alkaloids have received much interest because of their tremendous structural diversity and broad spectrum of biological and pharmaceutical activities (Rozwadowska, 1994; Scott & Williams, 2002; Chrzanowska & Rozwadowska, 2004). As part of our own work in this area, we prepared the title compound, (I), as an intermediate in the synthesis of tyrosine-derived N-[(phenylsulfonyl)alkyl]oxazolidinones as an extension of Petrini's methodology (Tussetschläger, et al., 2007). The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the mean planes of the C1 - C9/O1 ethoxybenzyl ring and the C10/N/C12/O2/C11/O3 oxazolidine ring is 60.3 (4)°. In the crystal structure, adjacent molecules are linked through N—H···O type hydrogen-bonding interactions resulting in chains running in the b direction (Table 1). The structure also contains non-classical hydrogen bonds of the type C—H···O linking the molecules into chains along the a-axis.

Related literature top

For background literature, see: Chrzanowska & Rozwadowska (2004); Rozwadowska (1994); Scott & Williams (2002); Tussetschläger et al. (2007).

Experimental top

Sodium borohydride was added to a solution of 2-(tert-butoxycarbonylamino)-3-(4-ethoxyphenyl)propanoic acid (3.09 g, 10 mmol) in tetrahydrofuran (50 ml). Then methanol (5 ml) was slowly added to the resulting suspension and the temperature kept below 243 K. After the mixture was stirred for 1 h at room temperature, the excess reagent was destroyed by addition of acetic acid (1 ml). The solvent was evaporated, and the oily residue was diluted with water (50 ml) and extracted three times with ethyl acetate (25 ml) each. The combined organic extracts were wash with brine, dried with sodium sulfate, and concentrated in vacuo. The crude tert-butyl 1-(4-ethoxyphenyl)-3- hydroxypropan-2-ylcarbamate was obtained 2.7 g. Then tert-butyl 1- (4-ethoxyphenyl)-3-hydroxypropan-2-ylcarbamate (2.7 g) in THF (50 ml) was added to a suspension of sodium hydride (0.92 g, 23 mmol) in THF (120 ml) over a period of 20 min, stirred for 12 h, then quenched with a saturated solution of aqueous ammonium chloride (45 ml). The reaction mixture was then extracted three times with ethyl acetate (25 ml) each, the organic layers combined, washed with aqueous hydrochloric acid (60 ml, 5% solution), saturated NaHCO₃ solution (60 ml), and brine (60 ml), and then dried over sodium sulfate. The solvent was then removed in vacuo to yield the title compound (1.81 g, 8.2 mmol) as a white solid. The title compound was crystalized by slow evaporation of a solution in methanol.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. A view of the title compound with the atomic numbering scheme. Displacement ellipsoids were drawn at the 30% probability level.

4-(4-Ethoxybenzyl)-1,3-oxazolidin-2-one top

Crystal data top

C₁₂H₁₅NO₃	F(000) = 472
M_r = 221.25	D_x = 1.264 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 5.7960 (12) Å	θ = 9–12°
b = 9.924 (2) Å	µ = 0.09 mm⁻¹
c = 20.209 (4) Å	T = 293 K
V = 1162.4 (4) Å³	Needle, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	904 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
Graphite monochromator	θ_max = 25.3°, θ_min = 2.0°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989)	k = 0→11
T_min = 0.973, T_max = 0.991	l = −24→24
2427 measured reflections	3 standard reflections every 200 reflections
1246 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.043	H-atom parameters constrained
wR(F²) = 0.150	w = 1/[σ²(F_o²) + (0.08P)² + 0.28P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1246 reflections	Δρ_max = 0.17 e Å⁻³
146 parameters	Δρ_min = −0.19 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.031 (6)

Crystal data top

C₁₂H₁₅NO₃	V = 1162.4 (4) Å³
M_r = 221.25	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 5.7960 (12) Å	µ = 0.09 mm⁻¹
b = 9.924 (2) Å	T = 293 K
c = 20.209 (4) Å	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	904 reflections with I > 2σ(I)
Absorption correction: ψ scan (CAD-4 Software; Enraf–Nonius, 1989)	R_int = 0.043
T_min = 0.973, T_max = 0.991	3 standard reflections every 200 reflections
2427 measured reflections	intensity decay: 1%
1246 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.150	H-atom parameters constrained
S = 1.01	Δρ_max = 0.17 e Å⁻³
1246 reflections	Δρ_min = −0.19 e Å⁻³
146 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
N	−0.1179 (6)	0.5921 (3)	1.00790 (17)	0.0589 (9)
H0A	−0.1581	0.6728	1.0182	0.071*
O1	0.4026 (6)	0.3182 (3)	1.25901 (14)	0.0754 (9)
O2	0.0990 (5)	0.4271 (3)	0.97230 (16)	0.0696 (9)
O3	0.2494 (5)	0.6348 (3)	0.97241 (19)	0.0845 (11)
C1	0.7072 (9)	0.3538 (5)	1.3348 (2)	0.0801 (14)
H1A	0.7873	0.4207	1.3603	0.120*
H1B	0.8134	0.3107	1.3051	0.120*
H1C	0.6415	0.2878	1.3639	0.120*
C2	0.5179 (9)	0.4202 (4)	1.2955 (2)	0.0725 (12)
H2A	0.4105	0.4650	1.3250	0.087*
H2B	0.5824	0.4869	1.2657	0.087*
C3	0.2251 (8)	0.3587 (4)	1.21793 (19)	0.0596 (11)
C4	0.1675 (9)	0.4911 (4)	1.2056 (2)	0.0651 (12)
H4A	0.2504	0.5608	1.2252	0.078*
C5	−0.0159 (8)	0.5190 (4)	1.1637 (2)	0.0643 (12)
H5A	−0.0542	0.6086	1.1559	0.077*
C6	−0.1449 (8)	0.4190 (4)	1.13291 (19)	0.0595 (11)
C7	−0.0758 (10)	0.2863 (4)	1.1469 (2)	0.0648 (13)
H7A	−0.1548	0.2156	1.1270	0.078*
C8	0.1011 (10)	0.2573 (4)	1.1883 (2)	0.0686 (13)
H8A	0.1391	0.1679	1.1967	0.082*
C9	−0.3390 (7)	0.4521 (4)	1.0869 (2)	0.0660 (12)
H9A	−0.4173	0.5317	1.1033	0.079*
H9B	−0.4490	0.3784	1.0877	0.079*
C10	−0.2686 (7)	0.4773 (4)	1.0154 (2)	0.0558 (10)
H10A	−0.4074	0.4910	0.9885	0.067*
C11	−0.1210 (7)	0.3682 (4)	0.9839 (2)	0.0568 (10)
H11A	−0.1071	0.2914	1.0134	0.068*
H11B	−0.1892	0.3381	0.9427	0.068*
C12	0.0875 (7)	0.5618 (4)	0.9838 (2)	0.0565 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0555 (19)	0.0374 (15)	0.084 (2)	0.0096 (16)	0.0052 (19)	−0.0044 (15)
O1	0.096 (2)	0.0555 (16)	0.0745 (18)	−0.0051 (18)	0.000 (2)	−0.0037 (14)
O2	0.0475 (15)	0.0404 (13)	0.121 (2)	0.0004 (13)	0.0102 (17)	−0.0137 (15)
O3	0.0402 (15)	0.0525 (16)	0.161 (3)	−0.0080 (15)	0.003 (2)	−0.0047 (18)
C1	0.081 (3)	0.082 (3)	0.077 (3)	0.000 (3)	0.000 (3)	−0.009 (3)
C2	0.079 (3)	0.063 (2)	0.076 (3)	−0.006 (3)	−0.001 (3)	−0.009 (2)
C3	0.067 (3)	0.058 (2)	0.054 (2)	−0.005 (2)	0.010 (2)	0.0022 (18)
C4	0.079 (3)	0.051 (2)	0.065 (2)	−0.007 (2)	0.002 (3)	−0.0078 (19)
C5	0.071 (3)	0.048 (2)	0.074 (3)	−0.001 (2)	0.011 (3)	−0.008 (2)
C6	0.066 (3)	0.053 (2)	0.059 (2)	−0.010 (2)	0.020 (2)	−0.0044 (18)
C7	0.083 (3)	0.048 (2)	0.064 (2)	−0.016 (2)	0.007 (3)	−0.0046 (18)
C8	0.100 (4)	0.045 (2)	0.061 (2)	−0.006 (3)	0.006 (3)	0.0016 (18)
C9	0.054 (2)	0.059 (2)	0.085 (3)	−0.003 (2)	0.015 (2)	−0.012 (2)
C10	0.0358 (18)	0.049 (2)	0.082 (3)	0.0002 (18)	−0.007 (2)	−0.005 (2)
C11	0.054 (2)	0.048 (2)	0.069 (2)	−0.010 (2)	−0.002 (2)	−0.0077 (18)
C12	0.044 (2)	0.0382 (18)	0.088 (3)	0.0028 (18)	−0.011 (2)	−0.0025 (19)

Geometric parameters (Å, º) top

N—C12	1.321 (5)	C4—C5	1.387 (6)
N—C10	1.444 (5)	C4—H4A	0.9300
N—H0A	0.8600	C5—C6	1.390 (6)
O1—C3	1.382 (5)	C5—H5A	0.9300
O1—C2	1.420 (5)	C6—C7	1.405 (6)
O2—C12	1.358 (5)	C6—C9	1.497 (6)
O2—C11	1.423 (5)	C7—C8	1.354 (7)
O3—C12	1.208 (5)	C7—H7A	0.9300
C1—C2	1.506 (6)	C8—H8A	0.9300
C1—H1A	0.9600	C9—C10	1.522 (6)
C1—H1B	0.9600	C9—H9A	0.9700
C1—H1C	0.9600	C9—H9B	0.9700
C2—H2A	0.9700	C10—C11	1.519 (5)
C2—H2B	0.9700	C10—H10A	0.9800
C3—C8	1.374 (6)	C11—H11A	0.9700
C3—C4	1.379 (6)	C11—H11B	0.9700

C12—N—C10	113.8 (3)	C7—C6—C9	123.1 (4)
C12—N—H0A	123.1	C8—C7—C6	122.7 (4)
C10—N—H0A	123.1	C8—C7—H7A	118.7
C3—O1—C2	117.1 (3)	C6—C7—H7A	118.7
C12—O2—C11	109.4 (3)	C7—C8—C3	120.6 (4)
C2—C1—H1A	109.5	C7—C8—H8A	119.7
C2—C1—H1B	109.5	C3—C8—H8A	119.7
H1A—C1—H1B	109.5	C6—C9—C10	115.1 (3)
C2—C1—H1C	109.5	C6—C9—H9A	108.5
H1A—C1—H1C	109.5	C10—C9—H9A	108.5
H1B—C1—H1C	109.5	C6—C9—H9B	108.5
O1—C2—C1	107.8 (4)	C10—C9—H9B	108.5
O1—C2—H2A	110.2	H9A—C9—H9B	107.5
C1—C2—H2A	110.2	N—C10—C11	100.2 (3)
O1—C2—H2B	110.2	N—C10—C9	113.0 (3)
C1—C2—H2B	110.2	C11—C10—C9	115.5 (3)
H2A—C2—H2B	108.5	N—C10—H10A	109.2
C8—C3—C4	119.5 (4)	C11—C10—H10A	109.2
C8—C3—O1	116.0 (4)	C9—C10—H10A	109.2
C4—C3—O1	124.4 (4)	O2—C11—C10	106.3 (3)
C3—C4—C5	119.1 (4)	O2—C11—H11A	110.5
C3—C4—H4A	120.5	C10—C11—H11A	110.5
C5—C4—H4A	120.5	O2—C11—H11B	110.5
C4—C5—C6	122.9 (4)	C10—C11—H11B	110.5
C4—C5—H5A	118.6	H11A—C11—H11B	108.7
C6—C5—H5A	118.6	O3—C12—N	129.3 (4)
C5—C6—C7	115.2 (4)	O3—C12—O2	121.3 (4)
C5—C6—C9	121.7 (4)	N—C12—O2	109.4 (4)

C3—O1—C2—C1	−178.3 (3)	C5—C6—C9—C10	85.5 (5)
C2—O1—C3—C8	−173.6 (4)	C7—C6—C9—C10	−92.8 (5)
C2—O1—C3—C4	6.2 (6)	C12—N—C10—C11	−5.5 (4)
C8—C3—C4—C5	0.3 (6)	C12—N—C10—C9	118.0 (4)
O1—C3—C4—C5	−179.5 (4)	C6—C9—C10—N	−62.6 (4)
C3—C4—C5—C6	−0.4 (6)	C6—C9—C10—C11	52.0 (5)
C4—C5—C6—C7	−0.3 (6)	C12—O2—C11—C10	−9.0 (5)
C4—C5—C6—C9	−178.8 (4)	N—C10—C11—O2	8.4 (4)
C5—C6—C7—C8	1.1 (6)	C9—C10—C11—O2	−113.4 (4)
C9—C6—C7—C8	179.5 (4)	C10—N—C12—O3	−179.6 (4)
C6—C7—C8—C3	−1.1 (7)	C10—N—C12—O2	0.3 (5)
C4—C3—C8—C7	0.4 (6)	C11—O2—C12—O3	−174.4 (4)
O1—C3—C8—C7	−179.7 (4)	C11—O2—C12—N	5.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O3ⁱ	0.86	1.99	2.845 (4)	171
C10—H10A···O3ⁱⁱ	0.98	2.47	3.317 (5)	144

Symmetry codes: (i) x−1/2, −y+3/2, −z+2; (ii) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₅NO₃
M_r	221.25
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	5.7960 (12), 9.924 (2), 20.209 (4)
V (Å³)	1162.4 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (CAD-4 Software; Enraf–Nonius, 1989)
T_min, T_max	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	2427, 1246, 904
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.150, 1.01
No. of reflections	1246
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O3ⁱ	0.8600	1.9900	2.845 (4)	171.00

Symmetry code: (i) x−1/2, −y+3/2, −z+2.

Acknowledgements

The authors acknowledge financial support from Jiangsu Institute of Nuclear Medicine.

References

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