3-Phenyl­oxazolidin-2-one

In the title compound, C₉H₉NO₂, amide–π-system conjugation results in an almost coplanar arrangement of the phenyl ring and the almost planar heterocycle. In the crystal structure, π-stacked dimers [perpendicular distance 3.563 (2) Å] inter­act with neighbouring dimers via C—H...π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.039
• wR factor = 0.106
• Data-to-parameter ratio = 13.4

checkCIF/PLATON results

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Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)         40 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

The title compound, (I), was unintentionally prepared upon the attempted synthesis of 2,2'-spirobi[3-phenyl-1,3-oxazolone].

In the molecule of (I) a five-membered heterocycle is bonded to a phenyl moiety as an exocyclic substituent on the N atom (Fig. 1). Since (I) is an amide, the N atom binds essentially planarly. The phenyl group and the heterocycle are not in perfect co-planarity, yet the torsional angle between the two planes is found to be smaller than 9°. The heterocycle adopts a twist conformation; however, puckering is small, the amplitude being only 0.085 (2) Å. Bond lengths and angles are normal (List, 2000).

In the crystal structure, pairs of molecules are oriented parallel to each other with the aromatic moieties facing the heterocyclic rings (Fig. 2). The perpendicular distance of the dimer's mean planes is 3.563 (2) Å. The π-stacked dimers interact with neighbouring dimers via C–H/π interactions: for C3–H31···Cg, the H···Cg distance is 2.72 Å (Cg is the centroid of the phenyl ring at 2_645).

Related literature

For related literature, see: Shibuya et al. (1998); List (2000).

S2. Experimental

The title compound was accidentially obtained as the product upon the attempted synthesis of 2,2'-spirobi[3-phenyl-1,3-oxazolone] according to a published procedure (Shibuya et al., 1998) by reacting 2-anilinoethanol with carbon disulfide in acetonitrile in the presence of triethylamine and silver nitrate. Crystals suitable for X-ray analysis were obtained directly from the crystallized reaction product.

S3. Refinement

H atoms were located in a difference map and refined as riding on their parent atoms with C—H = 0.95 and 0.99 Å, for aromatic and methylene H atoms. One common isotropic displacement parameter for all H atoms was refined to U_iso(H) = 0.0444 (15) Ų.

Computing details

Data collection: COLLECT (Nonius, 2004); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor 1997; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram of (I), viewed along [-1 0 0].

3-Phenyloxazolidin-2-one

Crystal data

C9H9NO2	F(000) = 344
Mr = 163.17	Dx = 1.421 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6001 reflections
a = 8.9290 (4) Å	θ = 3.1–26.0°
b = 8.1865 (4) Å	µ = 0.10 mm^−1
c = 10.7583 (4) Å	T = 200 K
β = 104.127 (3)°	Platelet, colorless
V = 762.62 (6) Å^3	0.32 × 0.29 × 0.06 mm
Z = 4

Data collection

Nonius KappaCCD diffractometer	1205 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.052
MONTEL, graded multilayered X-ray optics monochromator	θmax = 26.0°, θmin = 3.2°
CCD; rotation images; thick slices scans	h = −11→11
4808 measured reflections	k = −9→10
1484 independent reflections	l = −13→13

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.039	Only H-atom displacement parameters refined
wR(F^2) = 0.106	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 0.1977P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
1484 reflections	Δρmax = 0.16 e Å^−3
111 parameters	Δρmin = −0.16 e Å^−3
0 restraints	Extinction correction: SHELXL
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.042 (6)

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.90188 (11)	0.16725 (14)	0.22618 (10)	0.0422 (3)
O2	0.75635 (13)	0.32281 (15)	0.07287 (11)	0.0517 (4)
N1	0.64862 (13)	0.12175 (14)	0.17631 (11)	0.0295 (3)
C1	0.76398 (17)	0.21333 (19)	0.14944 (14)	0.0340 (4)
C2	0.88041 (19)	0.0318 (2)	0.30567 (16)	0.0429 (4)
H21	0.9276	0.0556	0.3971	0.0444 (15)*
H22	0.9282	−0.0685	0.2812	0.0444 (15)*
C3	0.70748 (17)	0.01065 (18)	0.28320 (13)	0.0322 (4)
H31	0.6760	−0.1035	0.2599	0.0444 (15)*
H32	0.6714	0.0425	0.3598	0.0444 (15)*
C4	0.48820 (16)	0.13842 (16)	0.12138 (12)	0.0276 (3)
C5	0.38575 (16)	0.04866 (19)	0.17378 (14)	0.0343 (4)
H5	0.4245	−0.0220	0.2444	0.0444 (15)*
C6	0.22804 (18)	0.0620 (2)	0.12354 (15)	0.0402 (4)
H6	0.1593	−0.0001	0.1597	0.0444 (15)*
C7	0.16968 (17)	0.1646 (2)	0.02150 (15)	0.0403 (4)
H7	0.0613	0.1742	−0.0122	0.0444 (15)*
C8	0.27030 (18)	0.2529 (2)	−0.03092 (14)	0.0378 (4)
H8	0.2304	0.3233	−0.1014	0.0444 (15)*
C9	0.42905 (17)	0.24101 (18)	0.01742 (13)	0.0328 (4)
H9	0.4970	0.3024	−0.0201	0.0444 (15)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0282 (6)	0.0456 (7)	0.0504 (7)	−0.0038 (5)	0.0048 (5)	0.0089 (5)
O2	0.0416 (7)	0.0524 (8)	0.0590 (8)	−0.0089 (5)	0.0085 (5)	0.0224 (6)
N1	0.0279 (6)	0.0284 (7)	0.0326 (6)	0.0004 (5)	0.0080 (5)	0.0032 (5)
C1	0.0309 (8)	0.0324 (8)	0.0390 (8)	−0.0019 (6)	0.0092 (6)	0.0019 (7)
C2	0.0343 (9)	0.0429 (10)	0.0480 (9)	0.0000 (7)	0.0033 (7)	0.0096 (7)
C3	0.0340 (8)	0.0311 (8)	0.0307 (7)	0.0017 (6)	0.0062 (6)	0.0034 (6)
C4	0.0282 (7)	0.0260 (7)	0.0288 (7)	0.0007 (6)	0.0074 (5)	−0.0047 (6)
C5	0.0325 (8)	0.0330 (8)	0.0376 (8)	−0.0009 (6)	0.0087 (6)	0.0032 (6)
C6	0.0314 (8)	0.0423 (10)	0.0476 (9)	−0.0056 (7)	0.0112 (7)	−0.0011 (7)
C7	0.0289 (8)	0.0445 (10)	0.0441 (9)	0.0015 (7)	0.0023 (6)	−0.0071 (7)
C8	0.0392 (9)	0.0397 (9)	0.0313 (7)	0.0069 (7)	0.0025 (6)	−0.0013 (7)
C9	0.0350 (8)	0.0334 (8)	0.0315 (7)	0.0020 (6)	0.0106 (6)	0.0000 (6)

Geometric parameters (Å, º)

O1—C1	1.3579 (18)	C4—C5	1.395 (2)
O1—C2	1.4414 (19)	C4—C9	1.395 (2)
O2—C1	1.2079 (18)	C5—C6	1.384 (2)
N1—C1	1.3608 (19)	C5—H5	0.9500
N1—C4	1.4164 (18)	C6—C7	1.380 (2)
N1—C3	1.4598 (17)	C6—H6	0.9500
C2—C3	1.513 (2)	C7—C8	1.377 (2)
C2—H21	0.9900	C7—H7	0.9500
C2—H22	0.9900	C8—C9	1.389 (2)
C3—H31	0.9900	C8—H8	0.9500
C3—H32	0.9900	C9—H9	0.9500
C1—O1—C2	110.01 (11)	C5—C4—C9	118.92 (13)
C1—N1—C4	126.80 (12)	C5—C4—N1	118.47 (12)
C1—N1—C3	111.40 (12)	C9—C4—N1	122.60 (13)
C4—N1—C3	121.44 (11)	C6—C5—C4	120.38 (14)
O2—C1—O1	120.84 (13)	C6—C5—H5	119.8
O2—C1—N1	129.34 (14)	C4—C5—H5	119.8
O1—C1—N1	109.81 (12)	C7—C6—C5	120.63 (15)
O1—C2—C3	105.75 (12)	C7—C6—H6	119.7
O1—C2—H21	110.6	C5—C6—H6	119.7
C3—C2—H21	110.6	C8—C7—C6	119.23 (14)
O1—C2—H22	110.6	C8—C7—H7	120.4
C3—C2—H22	110.6	C6—C7—H7	120.4
H21—C2—H22	108.7	C7—C8—C9	121.21 (14)
N1—C3—C2	102.22 (12)	C7—C8—H8	119.4
N1—C3—H31	111.3	C9—C8—H8	119.4
C2—C3—H31	111.3	C8—C9—C4	119.63 (14)
N1—C3—H32	111.3	C8—C9—H9	120.2
C2—C3—H32	111.3	C4—C9—H9	120.2
H31—C3—H32	109.2
C2—O1—C1—O2	−178.30 (15)	C3—N1—C4—C5	1.54 (19)
C2—O1—C1—N1	2.78 (17)	C1—N1—C4—C9	8.8 (2)
C4—N1—C1—O2	−2.2 (3)	C3—N1—C4—C9	−178.57 (13)
C3—N1—C1—O2	−175.42 (15)	C9—C4—C5—C6	−0.3 (2)
C4—N1—C1—O1	176.62 (12)	N1—C4—C5—C6	179.63 (13)
C3—N1—C1—O1	3.37 (17)	C4—C5—C6—C7	−0.3 (2)
C1—O1—C2—C3	−7.44 (17)	C5—C6—C7—C8	0.6 (2)
C1—N1—C3—C2	−7.58 (16)	C6—C7—C8—C9	−0.3 (2)
C4—N1—C3—C2	178.76 (12)	C7—C8—C9—C4	−0.3 (2)
O1—C2—C3—N1	8.73 (16)	C5—C4—C9—C8	0.6 (2)
C1—N1—C4—C5	−171.09 (14)	N1—C4—C9—C8	−179.31 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H31···Cg^i	0.99	2.72	3.3854 (16)	125

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