4-(2-Hydroxy-benzyl-idene)-3-methyl-isoxazol-5(4H)-one.

The mol-ecular skeleton of the title mol-ecule, C(11)H(9)NO(3), is approximately planar (r.m.s. deviation = 0.0056 Å); the two rings form a dihedral angle of 6.5 (1)°. In the crystal structure, inter-molecular O-H⋯N hydrogen bonds involving the H atom of the hydr-oxy group and the N atom of the isoxazole ring link mol-ecules into chains running along the c axis.

Related literature

For the biological activity of aryl­methyl­ene isoxazolone derivatives, see: Ishioka et al. (2002 ▶); Liu et al. (2005 ▶). For related structures, see: Cocivera et al. (1976 ▶); Villemin et al. (1993 ▶); Zhang et al. (2008 ▶).

Experimental

Crystal data

C11H9NO3

M = 203.19

Monoclinic,

a = 8.0172 (12) Å

b = 6.8620 (9) Å

c = 17.535 (2) Å

β = 99.962 (2)°

V = 950.1 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 298 K

0.43 × 0.30 × 0.28 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.956, T max = 0.971

4598 measured reflections

1669 independent reflections

1067 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.125

S = 1.03

1669 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2004 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045486/cv2639sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045486/cv2639Isup2.hkl

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

C11H9NO3	F(000) = 424
Mr = 203.19	Dx = 1.420 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1182 reflections
a = 8.0172 (12) Å	θ = 2.4–22.5°
b = 6.8620 (9) Å	µ = 0.11 mm−1
c = 17.535 (2) Å	T = 298 K
β = 99.962 (2)°	Prism, yellow
V = 950.1 (2) Å3	0.43 × 0.30 × 0.28 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	1669 independent reflections
Radiation source: fine-focus sealed tube	1067 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
Tmin = 0.956, Tmax = 0.971	k = −8→7
4598 measured reflections	l = −19→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0547P)2 + 0.2598P] where P = (Fo2 + 2Fc2)/3
1669 reflections	(Δ/σ)max < 0.001
137 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.18 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	0.1424 (3)	0.7335 (3)	0.29966 (10)	0.0495 (6)
O1	0.2203 (2)	0.5472 (2)	0.29343 (8)	0.0573 (5)
O2	0.3282 (3)	0.3078 (3)	0.37132 (10)	0.0668 (6)
O3	0.1516 (2)	0.6467 (2)	0.64469 (8)	0.0579 (5)
H3	0.1416	0.6505	0.6904	0.087*
C1	0.2599 (3)	0.4642 (4)	0.36509 (12)	0.0474 (6)
C2	0.2013 (3)	0.5995 (3)	0.41967 (12)	0.0372 (6)
C3	0.1320 (3)	0.7584 (3)	0.37120 (12)	0.0404 (6)
C4	0.0543 (3)	0.9391 (3)	0.39499 (13)	0.0541 (7)
H4A	0.0185	1.0195	0.3504	0.081*
H4B	0.1358	1.0085	0.4316	0.081*
H4C	−0.0418	0.9065	0.4184	0.081*
C5	0.2050 (3)	0.5923 (3)	0.49738 (12)	0.0388 (6)
H5	0.1541	0.6992	0.5165	0.047*
C6	0.2713 (3)	0.4536 (3)	0.55603 (11)	0.0377 (5)
C7	0.2432 (3)	0.4893 (3)	0.63213 (12)	0.0406 (6)
C8	0.3061 (3)	0.3630 (4)	0.69154 (13)	0.0483 (6)
H8	0.2866	0.3871	0.7414	0.058*
C9	0.3967 (3)	0.2032 (4)	0.67709 (14)	0.0567 (7)
H9	0.4394	0.1194	0.7175	0.068*
C10	0.4262 (3)	0.1639 (4)	0.60287 (15)	0.0572 (7)
H10	0.4876	0.0543	0.5934	0.069*
C11	0.3640 (3)	0.2882 (3)	0.54405 (13)	0.0481 (6)
H11	0.3841	0.2615	0.4944	0.058*

	U11	U22	U33	U12	U13	U23
N1	0.0615 (14)	0.0559 (13)	0.0319 (11)	0.0024 (11)	0.0107 (9)	0.0008 (9)
O1	0.0808 (13)	0.0632 (11)	0.0295 (9)	0.0095 (10)	0.0140 (8)	−0.0030 (8)
O2	0.0956 (15)	0.0587 (12)	0.0470 (11)	0.0183 (11)	0.0150 (10)	−0.0060 (9)
O3	0.0894 (14)	0.0585 (11)	0.0271 (8)	0.0131 (10)	0.0142 (8)	−0.0018 (7)
C1	0.0577 (17)	0.0501 (15)	0.0351 (13)	−0.0025 (13)	0.0100 (10)	−0.0013 (11)
C2	0.0395 (14)	0.0437 (13)	0.0291 (11)	−0.0061 (10)	0.0074 (9)	−0.0026 (10)
C3	0.0402 (14)	0.0482 (14)	0.0331 (12)	−0.0072 (11)	0.0072 (10)	−0.0003 (10)
C4	0.0650 (18)	0.0524 (15)	0.0454 (14)	0.0074 (14)	0.0109 (12)	0.0061 (12)
C5	0.0410 (14)	0.0423 (13)	0.0343 (12)	−0.0040 (11)	0.0101 (10)	−0.0030 (10)
C6	0.0385 (13)	0.0441 (13)	0.0304 (11)	−0.0061 (11)	0.0056 (9)	0.0018 (10)
C7	0.0434 (14)	0.0433 (13)	0.0349 (12)	−0.0046 (11)	0.0060 (9)	−0.0011 (10)
C8	0.0493 (16)	0.0619 (16)	0.0338 (13)	−0.0047 (13)	0.0078 (11)	0.0089 (12)
C9	0.0494 (17)	0.0666 (18)	0.0532 (16)	0.0012 (14)	0.0067 (12)	0.0243 (13)
C10	0.0520 (17)	0.0590 (16)	0.0622 (17)	0.0088 (14)	0.0144 (13)	0.0145 (14)
C11	0.0470 (15)	0.0562 (15)	0.0438 (14)	0.0009 (13)	0.0151 (11)	−0.0003 (12)

N1—C3	1.283 (3)	C5—C6	1.434 (3)
N1—O1	1.435 (2)	C5—H5	0.9300
O1—C1	1.366 (3)	C6—C11	1.392 (3)
O2—C1	1.201 (3)	C6—C7	1.413 (3)
O3—C7	1.346 (3)	C7—C8	1.382 (3)
O3—H3	0.8200	C8—C9	1.363 (3)
C1—C2	1.467 (3)	C8—H8	0.9300
C2—C5	1.359 (3)	C9—C10	1.389 (4)
C2—C3	1.434 (3)	C9—H9	0.9300
C3—C4	1.479 (3)	C10—C11	1.364 (3)
C4—H4A	0.9600	C10—H10	0.9300
C4—H4B	0.9600	C11—H11	0.9300
C4—H4C	0.9600
C3—N1—O1	107.22 (17)	C6—C5—H5	113.4
C1—O1—N1	109.63 (16)	C11—C6—C7	117.43 (19)
C7—O3—H3	109.5	C11—C6—C5	125.0 (2)
O2—C1—O1	119.1 (2)	C7—C6—C5	117.5 (2)
O2—C1—C2	134.3 (2)	O3—C7—C8	121.2 (2)
O1—C1—C2	106.7 (2)	O3—C7—C6	118.35 (19)
C5—C2—C3	124.1 (2)	C8—C7—C6	120.4 (2)
C5—C2—C1	132.6 (2)	C9—C8—C7	120.1 (2)
C3—C2—C1	103.26 (18)	C9—C8—H8	120.0
N1—C3—C2	113.2 (2)	C7—C8—H8	120.0
N1—C3—C4	119.3 (2)	C8—C9—C10	120.9 (2)
C2—C3—C4	127.5 (2)	C8—C9—H9	119.6
C3—C4—H4A	109.5	C10—C9—H9	119.6
C3—C4—H4B	109.5	C11—C10—C9	119.2 (3)
H4A—C4—H4B	109.5	C11—C10—H10	120.4
C3—C4—H4C	109.5	C9—C10—H10	120.4
H4A—C4—H4C	109.5	C10—C11—C6	122.0 (2)
H4B—C4—H4C	109.5	C10—C11—H11	119.0
C2—C5—C6	133.2 (2)	C6—C11—H11	119.0
C2—C5—H5	113.4
C3—N1—O1—C1	−1.5 (3)	C1—C2—C5—C6	2.1 (4)
N1—O1—C1—O2	−179.2 (2)	C2—C5—C6—C11	4.8 (4)
N1—O1—C1—C2	1.5 (2)	C2—C5—C6—C7	−176.4 (2)
O2—C1—C2—C5	0.0 (5)	C11—C6—C7—O3	−178.9 (2)
O1—C1—C2—C5	179.1 (2)	C5—C6—C7—O3	2.2 (3)
O2—C1—C2—C3	179.9 (3)	C11—C6—C7—C8	−0.1 (3)
O1—C1—C2—C3	−1.0 (2)	C5—C6—C7—C8	−179.0 (2)
O1—N1—C3—C2	0.9 (3)	O3—C7—C8—C9	179.2 (2)
O1—N1—C3—C4	−179.32 (19)	C6—C7—C8—C9	0.3 (4)
C5—C2—C3—N1	180.0 (2)	C7—C8—C9—C10	−0.5 (4)
C1—C2—C3—N1	0.0 (3)	C8—C9—C10—C11	0.3 (4)
C5—C2—C3—C4	0.2 (4)	C9—C10—C11—C6	−0.1 (4)
C1—C2—C3—C4	−179.7 (2)	C7—C6—C11—C10	−0.1 (3)
C3—C2—C5—C6	−177.8 (2)	C5—C6—C11—C10	178.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1i	0.82	2.07	2.852 (2)	159

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯N1i	0.82	2.07	2.852 (2)	159

Symmetry code: (i) .