4-[(2-Methyl-5-oxo-4,5-dihydro-1,3-oxazol-4-yl-idene)meth-yl]phenyl acetate.

In the title compound, C(13)H(11)NO(4), an intramolecular C-H⋯N interaction helps to establish the conformation. In the crystal, two C-H⋯O contacts stack adjacent mol-ecules into a one-dimensional double chain running in the a-axis direction.

Related literature

The title compound is an important medical inter­mediate, see: Baker (1951 ▶).

Experimental

Crystal data

C13H11NO4

M = 245.23

Triclinic,

a = 5.5802 (15) Å

b = 7.446 (2) Å

c = 15.012 (4) Å

α = 94.322 (4)°

β = 93.156 (4)°

γ = 108.136 (4)°

V = 589.1 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 293 K

0.14 × 0.13 × 0.08 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SAINT-Plus; Bruker, 2003 ▶) T min = 0.985, T max = 0.992

3324 measured reflections

2264 independent reflections

1707 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.164

S = 1.04

2264 reflections

153 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.14 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; 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: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809032243/kj2130sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809032243/kj2130Isup2.hkl

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

C13H11NO4	Z = 2
Mr = 245.23	F(000) = 256
Triclinic, P1	Dx = 1.383 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5802 (15) Å	Cell parameters from 2544 reflections
b = 7.446 (2) Å	θ = 3.0–25.4°
c = 15.012 (4) Å	µ = 0.10 mm−1
α = 94.322 (4)°	T = 293 K
β = 93.156 (4)°	Block, colourless
γ = 108.136 (4)°	0.14 × 0.13 × 0.08 mm
V = 589.1 (3) Å3

Bruker SMART APEX CCD area-detector diffractometer	2264 independent reflections
Radiation source: fine-focus sealed tube	1707 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 15 pixels mm-1	θmax = 26.1°, θmin = 2.7°
φ and ω scans	h = −6→3
Absorption correction: multi-scan (SAINT-Plus; Bruker, 2003)	k = −9→9
Tmin = 0.985, Tmax = 0.992	l = −18→15
3324 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0685P)2 + 0.3541P] where P = (Fo2 + 2Fc2)/3
2264 reflections	(Δ/σ)max < 0.001
153 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.14 e Å−3

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
N1	0.4700 (4)	0.9795 (3)	0.17606 (14)	0.0516 (6)
O1	1.3127 (3)	0.7316 (3)	0.44177 (12)	0.0565 (5)
O2	0.2844 (4)	0.6674 (3)	−0.02010 (13)	0.0725 (6)
O3	0.2123 (4)	0.9237 (3)	0.04884 (12)	0.0568 (5)
O4	1.0311 (4)	0.7157 (3)	0.54417 (13)	0.0631 (6)
C1	1.1357 (5)	0.7294 (4)	0.37105 (17)	0.0491 (6)
C2	1.1061 (5)	0.5959 (4)	0.29939 (17)	0.0540 (7)
H2	1.1950	0.5091	0.3002	0.065*
C3	0.9434 (5)	0.5922 (4)	0.22626 (17)	0.0518 (7)
H3	0.9229	0.5019	0.1778	0.062*
C4	0.8449 (5)	0.8561 (4)	0.29798 (17)	0.0529 (7)
H4	0.7574	0.9439	0.2980	0.064*
C5	1.0078 (5)	0.8603 (4)	0.37083 (17)	0.0552 (7)
H5	1.0312	0.9507	0.4195	0.066*
C6	0.8087 (5)	0.7219 (3)	0.22381 (16)	0.0460 (6)
C7	0.6402 (5)	0.7112 (4)	0.14512 (17)	0.0485 (6)
H7	0.6312	0.6140	0.1010	0.058*
C8	0.4950 (5)	0.8196 (3)	0.12586 (16)	0.0456 (6)
C9	0.3284 (5)	0.7834 (4)	0.04328 (18)	0.0517 (6)
C10	0.3096 (6)	1.0311 (4)	0.1294 (2)	0.0614 (5)
C11	0.2127 (6)	1.1906 (4)	0.1497 (2)	0.0614 (5)
H11A	0.2977	1.2619	0.2046	0.092*
H11B	0.0343	1.1427	0.1558	0.092*
H11C	0.2430	1.2715	0.1019	0.092*
C12	1.2360 (5)	0.7171 (4)	0.52634 (17)	0.0483 (6)
C13	1.4387 (6)	0.6997 (4)	0.5901 (2)	0.0614 (5)
H13A	1.4521	0.7817	0.6439	0.092*
H13B	1.5969	0.7353	0.5632	0.092*
H13C	1.3984	0.5707	0.6044	0.092*

	U11	U22	U33	U12	U13	U23
N1	0.0563 (13)	0.0520 (13)	0.0512 (12)	0.0260 (10)	−0.0003 (10)	−0.0015 (10)
O1	0.0468 (10)	0.0774 (13)	0.0507 (11)	0.0283 (9)	0.0027 (8)	0.0039 (9)
O2	0.0901 (16)	0.0779 (14)	0.0548 (12)	0.0428 (12)	−0.0140 (11)	−0.0167 (11)
O3	0.0637 (12)	0.0609 (12)	0.0513 (11)	0.0312 (10)	−0.0071 (9)	−0.0008 (9)
O4	0.0549 (12)	0.0869 (15)	0.0590 (12)	0.0379 (11)	0.0086 (9)	0.0100 (10)
C1	0.0461 (14)	0.0585 (15)	0.0465 (14)	0.0220 (12)	0.0049 (11)	0.0049 (12)
C2	0.0600 (16)	0.0603 (16)	0.0524 (15)	0.0355 (14)	0.0043 (13)	0.0020 (13)
C3	0.0634 (17)	0.0516 (15)	0.0470 (14)	0.0295 (13)	0.0039 (12)	−0.0020 (11)
C4	0.0654 (17)	0.0523 (15)	0.0507 (15)	0.0339 (13)	0.0019 (13)	0.0007 (12)
C5	0.0665 (17)	0.0570 (16)	0.0468 (14)	0.0299 (14)	−0.0005 (13)	−0.0061 (12)
C6	0.0512 (14)	0.0463 (13)	0.0450 (13)	0.0219 (11)	0.0058 (11)	0.0030 (11)
C7	0.0563 (15)	0.0482 (14)	0.0442 (13)	0.0220 (12)	0.0046 (11)	0.0001 (11)
C8	0.0502 (14)	0.0469 (13)	0.0429 (13)	0.0206 (11)	0.0040 (11)	0.0026 (10)
C9	0.0581 (16)	0.0522 (15)	0.0493 (14)	0.0249 (13)	0.0031 (12)	0.0025 (12)
C10	0.0603 (10)	0.0662 (11)	0.0616 (10)	0.0281 (8)	−0.0028 (8)	0.0013 (8)
C11	0.0603 (10)	0.0662 (11)	0.0616 (10)	0.0281 (8)	−0.0028 (8)	0.0013 (8)
C12	0.0472 (15)	0.0487 (14)	0.0487 (14)	0.0173 (12)	−0.0005 (11)	−0.0029 (11)
C13	0.0603 (10)	0.0662 (11)	0.0616 (10)	0.0281 (8)	−0.0028 (8)	0.0013 (8)

N1—C10	1.275 (3)	C4—C6	1.400 (3)
N1—C8	1.409 (3)	C4—H4	0.9300
O1—C12	1.363 (3)	C5—H5	0.9300
O1—C1	1.405 (3)	C6—C7	1.450 (3)
O2—C9	1.196 (3)	C7—C8	1.345 (4)
O3—C10	1.381 (3)	C7—H7	0.9300
O3—C9	1.390 (3)	C8—C9	1.463 (4)
O4—C12	1.185 (3)	C10—C11	1.469 (4)
C1—C2	1.374 (4)	C11—H11A	0.9600
C1—C5	1.376 (4)	C11—H11B	0.9600
C2—C3	1.379 (4)	C11—H11C	0.9600
C2—H2	0.9300	C12—C13	1.484 (4)
C3—C6	1.398 (3)	C13—H13A	0.9600
C3—H3	0.9300	C13—H13B	0.9600
C4—C5	1.375 (4)	C13—H13C	0.9600
C10—N1—C8	105.4 (2)	C7—C8—N1	129.4 (2)
C12—O1—C1	118.8 (2)	C7—C8—C9	122.6 (2)
C10—O3—C9	105.4 (2)	N1—C8—C9	108.0 (2)
C2—C1—C5	121.3 (2)	O2—C9—O3	121.5 (2)
C2—C1—O1	116.6 (2)	O2—C9—C8	133.5 (2)
C5—C1—O1	122.0 (2)	O3—C9—C8	105.0 (2)
C1—C2—C3	119.3 (2)	N1—C10—O3	116.3 (2)
C1—C2—H2	120.3	N1—C10—C11	128.7 (3)
C3—C2—H2	120.3	O3—C10—C11	115.1 (2)
C2—C3—C6	121.1 (2)	C10—C11—H11A	109.5
C2—C3—H3	119.5	C10—C11—H11B	109.5
C6—C3—H3	119.5	H11A—C11—H11B	109.5
C5—C4—C6	121.1 (2)	C10—C11—H11C	109.5
C5—C4—H4	119.4	H11A—C11—H11C	109.5
C6—C4—H4	119.4	H11B—C11—H11C	109.5
C4—C5—C1	119.4 (2)	O4—C12—O1	123.0 (2)
C4—C5—H5	120.3	O4—C12—C13	125.9 (3)
C1—C5—H5	120.3	O1—C12—C13	111.1 (2)
C3—C6—C4	117.8 (2)	C12—C13—H13A	109.5
C3—C6—C7	118.6 (2)	C12—C13—H13B	109.5
C4—C6—C7	123.6 (2)	H13A—C13—H13B	109.5
C8—C7—C6	130.1 (2)	C12—C13—H13C	109.5
C8—C7—H7	114.9	H13A—C13—H13C	109.5
C6—C7—H7	114.9	H13B—C13—H13C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···N1	0.93	2.45	3.098 (4)	127
C7—H7···O2i	0.93	2.53	3.417 (4)	160
C13—H13B···O4ii	0.96	2.50	3.382 (4)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯N1	0.93	2.45	3.098 (4)	127
C7—H7⋯O2i	0.93	2.53	3.417 (4)	160
C13—H13B⋯O4ii	0.96	2.50	3.382 (4)	152

Symmetry codes: (i) ; (ii) .