4-(2-Hydroxy­benzyl­idene)-3-methyl­isoxazol-5(4H)-one

Cheng, Q.; Xu, X.; Liu, L.; Zhang, L.

doi:10.1107/S1600536809045486

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3012

doi:10.1107/S1600536809045486

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4-(2-Hydroxybenzylidene)-3-methylisoxazol-5(4H)-one

Qingfang Cheng,^a ^* Xing-you Xu,^a Li-sha Liu ^a and Li Zhang ^a

^aHuaihai Institute of Technology, Lianyungang 222005, People's Republic of China
^*Correspondence e-mail: cheng_qingfang@yahoo.com.cn

(Received 22 October 2009; accepted 29 October 2009; online 7 November 2009)

The molecular skeleton of the title molecule, C₁₁H₉NO₃, 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, intermolecular O—H⋯N hydrogen bonds involving the H atom of the hydroxy group and the N atom of the isoxazole ring link molecules 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_r = 203.19
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.125
S = 1.03
1669 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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.

Supporting information

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

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

checkCIF report

Comment top

Arylmethylene isoxazolone derivatives are effective anti-psychotics in the treatment of depression and schizophrenia. The study about arylmethylene isoxazolone derivatives mainly concentrates in the biological activities (Ishioka et al., 2002; Liu et al., 2005). However, structural studies of them have rarely been reported. As a part of our investigation on arylmethylene isoxazolone derivatives, we report here the structure of the title compound, (I), synthesized by three component condensation reaction of methyl acetoacetate, hydroxylamine with salicylaldehyde in aqueous media under ultrasonic irradiation.

In (I) (Fig. 1), all bond lengths and angles agree well with those reported for the related compounds (Cocivera et al., 1976; Villemin et al., 1993; Zhang et al., 2008). The molecular structure adopts a Z-configuration about the C2=C5 double bond. The hydroxy groups and the isoxazol groups are involved in intermolecular O—H···N hydrogen bonds (Table 1), which link the molecules into chain structure, hydroxy O atom in the molecule acts as hydrogen-bond donor to isoxazol N atom in the neighbouring molecule, so forming a chain structure.

Related literature top

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 top

A mixture of methyl acetoacetate (4 mol), hydroxylamine hydrochloride (4 mmol), and pyridine(4 mmol) in distilled water(10 ml) was irradiated in the water bath of an ultrasonic cleaner for 10 min., then salicylaldehyde(4 mmol) was slowly added to the mixture. The resulting mixture was irradiated in the water bath of an ultrasonic cleaner for 1.5 h. The solution was left at room temperature overnight, the obtained mushy solution was filtered and the solid was washed with cold water and ethanol. The crude product was recrystallized from ethanol to afford the desired product as a yellow solid. Single crystal of (I) were obtained by slow evaporation of aqueous ethanol(95%) solution at ambient temperature after 7 d. Elemental analysis, calculated for C11 H9 N O3: C 65.02, H 4.46, N 6.89%; found: C 65.09. H 4.49, N 6.92%.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex. Displacement ellipsoids are drawn at the 30% probability level.

4-(2-Hydroxybenzylidene)-3-methylisoxazol-5(4H)-one top

Crystal data top

C₁₁H₉NO₃	F(000) = 424
M_r = 203.19	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0547P)² + 0.2598P] where P = (F_o² + 2F_c²)/3
1669 reflections	(Δ/σ)_max < 0.001
137 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₁H₉NO₃	V = 950.1 (2) Å³
M_r = 203.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0172 (12) Å	µ = 0.11 mm⁻¹
b = 6.8620 (9) Å	T = 298 K
c = 17.535 (2) Å	0.43 × 0.30 × 0.28 mm
β = 99.962 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	1669 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1067 reflections with I > 2σ(I)
T_min = 0.956, T_max = 0.971	R_int = 0.034
4598 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.125	H-atom parameters constrained
S = 1.03	Δρ_max = 0.33 e Å⁻³
1669 reflections	Δρ_min = −0.18 e Å⁻³
137 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₉NO₃
M_r	203.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.0172 (12), 6.8620 (9), 17.535 (2)
β (°)	99.962 (2)
V (Å³)	950.1 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.43 × 0.30 × 0.28

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.956, 0.971
No. of measured, independent and observed [I > 2σ(I)] reflections	4598, 1669, 1067
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.125, 1.03
No. of reflections	1669
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.18

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2004), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···N1ⁱ	0.82	2.07	2.852 (2)	158.5

Symmetry code: (i) x, −y+3/2, z+1/2.

Acknowledgements

We are grateful to the Foundation of Jiangsu Key Laboratory of Marine Biotechnology for financial support (grant No. 2007HS009).

References

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