4-(4-Ethoxy-benz-yl)-1,3-oxazolidin-2-one.

In the title compound, C(12)H(15)NO(3), the ethoxy-benzyl ring plane forms a dihedral angle of 60.3 (4)° with the mean plane of the oxazolidine ring. The mol-ecules 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 = 221.25

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.150

S = 1.01

1246 reflections

146 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

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.

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

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

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

C12H15NO3	F(000) = 472
Mr = 221.25	Dx = 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

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

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(Fo2) + (0.08P)2 + 0.28P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1246 reflections	Δρmax = 0.17 e Å−3
146 parameters	Δρmin = −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)

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .