(3-Phenyl­isoxazol-5-yl)methanol

Yin, L.; Zhao, G.-L.; Jia, J.; Meng, Q.-Y.; Wang, J.

doi:10.1107/S1600536810003417

organic compounds

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ISSN: 2056-9890

Volume 66| Part 3| March 2010| Page o536

doi:10.1107/S1600536810003417

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(3-Phenylisoxazol-5-yl)methanol

Ling Yin,^a Gui-Long Zhao,^b Jiong Jia,^a Qing-Yang Meng ^a and Jian-wu Wang ^a ^*

^aSchool of Chemistry and Chemical Engineering, Shandong University, Jinan 250100, People's Republic of China, and ^bTianjin Key Laboratory of Molecular Design and Drug Discovery, Tianjin Institute of Pharmaceutical Research, Tianjin 300193, People's Republic of China
^*Correspondence e-mail: yugp2005@yahoo.com.cn

(Received 25 January 2010; accepted 27 January 2010; online 6 February 2010)

In the title compound, C₁₀H₉NO₂, the isoxazole and phenyl rings form a dihedral angle of 25.82 (3)°. In the crystal, intermolecular O—H⋯O hydrogen bonds link the molecules into ribbons propagating along [001]. The crystal packing is further stabilized by weak C—H⋯O and C—H⋯N interactions.

Related literature

For related structures, see: Tian & Li (2006 ); Tang et al. (2006 ).

Experimental

Crystal data

C₁₀H₉NO₂
M_r = 175.18
Monoclinic, C 2/c
a = 41.03 (4) Å
b = 5.694 (5) Å
c = 7.348 (7) Å
β = 98.51 (2)°
V = 1698 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.55 × 0.45 × 0.02 mm

Data collection

Bruker SMART APEX diffractometer
3328 measured reflections
1500 independent reflections
1182 reflections with I > 2σ(I)
R_int = 0.059

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.119
S = 1.05
1500 reflections
118 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2B⋯O2ⁱ	0.86	1.89	2.669 (4)	151
O2—H2A⋯O2ⁱⁱ	0.88	2.09	2.677 (5)	124
C8—H8⋯N1ⁱⁱⁱ	0.93	2.61	3.542 (4)	177
C10—H10B⋯O2^iv	0.97	2.58	3.352 (4)	137
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x, y, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z; (iv) -x, -y+2, -z+1.

Data collection: SMART (Bruker, 1998 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810003417/cv2692sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003417/cv2692Isup2.hkl

checkCIF report

Comment top

In continuation of our study of isoxazole derivatives (Tang et al., 2006), we present here the crystal structure of the title compound, (I).

In (I) (Fig. 1), the bond lengths and angles of the isoxazole ring are normal and comparable to those reported for related structures (Tian & Li, 2006; Tang et al., 2006). The mean planes of the benzene (C1—C6) and isoxazole (C7—C9/N1/O1) rings make a dihedral angle of 25.82 (3)°. Intermolecular O—H···O hydrogen bonds (Table 1) link the molecules into ribbons extended along the c axis. The crystal packing is further stabilized by weak C—H···O and C—H···N interactions (Table 1).

Related literature top

For related structures, see: Tian & Li (2006); Tang et al. (2006).

Experimental top

A round-bottomed flask was charged with benzaldoxime(5.0 g, 41.3 mmol) in 20 ml N, N-dimethyl formamide, and then N-chlorosuccinimide (1.20 g, 9.1 mmol) was added to the solution. Heating until N-chlorosuccinimide was solved, and the mixture was stirred at room temperature for 20 min, into the above solution was added N-chlorosuccinimide (4.80 g, 36.4 mmol) in batches under 308 K. After 3 h, propargyl alcohol ( 2.78 g, 49.6 mmol) was added, then the saturated solution of CuSO4.5H2O (0.62 g, 2.48 mmol) and L-ascorbic acid (1.75 g, 9.92 mmol) were added also. The solution of K₂CO₃ (3.14 g, 45.5 mmol) was added to the mixture and was stirred for 1 h. The reaction mixture was diluted with the saturated solution of ethylenediaminetetraacetic acid, and then was extracted with dichloromethane (3 times per 50 ml), and the extracts were dried over anhydrous Na₂SO₄. The solution was evaporated to afford a residue, which was purified by a silica-gel column chromatography (petroleum ether / ethyl acetate, 3:1 by volume) to afford a pale yellow solid (yield: 61.7%, m.p. 325–326 K). The crystals of (I) were obtained from petroleum ether / ethyl acetate / dichloromethane (3:1:1, V/V/V) by slow evaporation at room temperature.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), with atom labels and 40% probability displacement ellipsoids for non-H atoms.

(3-Phenylisoxazol-5-yl)methanol top

Crystal data top

C₁₀H₉NO₂	F(000) = 736
M_r = 175.18	D_x = 1.371 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1357 reflections
a = 41.03 (4) Å	θ = 3.0–28.1°
b = 5.694 (5) Å	µ = 0.10 mm⁻¹
c = 7.348 (7) Å	T = 298 K
β = 98.51 (2)°	Plate, colourless
V = 1698 (3) Å³	0.55 × 0.45 × 0.02 mm
Z = 8

Data collection top

Bruker SMART APEX diffractometer	1182 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.059
Graphite monochromator	θ_max = 25.1°, θ_min = 2.0°
phi and ω scans	h = −48→43
3328 measured reflections	k = −6→5
1500 independent reflections	l = −8→8

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0354P)² + 0.7771P] where P = (F_o² + 2F_c²)/3
1500 reflections	(Δ/σ)_max < 0.001
118 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₀H₉NO₂	V = 1698 (3) Å³
M_r = 175.18	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 41.03 (4) Å	µ = 0.10 mm⁻¹
b = 5.694 (5) Å	T = 298 K
c = 7.348 (7) Å	0.55 × 0.45 × 0.02 mm
β = 98.51 (2)°

Data collection top

Bruker SMART APEX diffractometer	1182 reflections with I > 2σ(I)
3328 measured reflections	R_int = 0.059
1500 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.05	Δρ_max = 0.16 e Å⁻³
1500 reflections	Δρ_min = −0.23 e Å⁻³
118 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
C1	0.15963 (5)	0.9135 (4)	0.2841 (2)	0.0424 (5)
H1	0.1439	1.0293	0.2497	0.051*
C2	0.19149 (5)	0.9476 (4)	0.2556 (3)	0.0470 (6)
H2	0.1973	1.0855	0.2009	0.056*
C3	0.21488 (5)	0.7785 (4)	0.3078 (3)	0.0484 (6)
H3	0.2366	0.8022	0.2889	0.058*
C4	0.20619 (5)	0.5744 (4)	0.3878 (3)	0.0457 (6)
H4	0.2221	0.4604	0.4237	0.055*
C5	0.17421 (5)	0.5374 (4)	0.4152 (2)	0.0403 (5)
H5	0.1685	0.3980	0.4682	0.048*
C6	0.15054 (5)	0.7074 (3)	0.3639 (2)	0.0352 (5)
C7	0.11668 (5)	0.6746 (4)	0.4006 (2)	0.0370 (5)
C8	0.09363 (5)	0.8478 (4)	0.4305 (3)	0.0438 (5)
H8	0.0961	1.0098	0.4236	0.053*
C9	0.06769 (5)	0.7318 (4)	0.4705 (3)	0.0460 (6)
C10	0.03668 (5)	0.8061 (5)	0.5327 (3)	0.0629 (7)
H10A	0.0377	0.7646	0.6615	0.076*
H10B	0.0350	0.9757	0.5237	0.076*
N1	0.10486 (4)	0.4641 (3)	0.4183 (2)	0.0501 (5)
O1	0.07313 (3)	0.4982 (3)	0.4643 (2)	0.0543 (4)
O2	0.00792 (4)	0.7069 (3)	0.4334 (3)	0.0808 (6)
H2B	0.0046	0.5589	0.4396	0.121*	0.50
H2A	0.0167	0.6698	0.3350	0.121*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0450 (13)	0.0391 (13)	0.0412 (10)	−0.0012 (10)	−0.0003 (9)	0.0019 (10)
C2	0.0546 (14)	0.0453 (14)	0.0412 (11)	−0.0104 (12)	0.0076 (9)	0.0033 (10)
C3	0.0405 (12)	0.0642 (17)	0.0415 (11)	−0.0082 (12)	0.0098 (9)	−0.0076 (11)
C4	0.0425 (13)	0.0513 (16)	0.0438 (11)	0.0086 (11)	0.0081 (9)	−0.0007 (11)
C5	0.0471 (12)	0.0362 (13)	0.0377 (10)	0.0027 (10)	0.0066 (8)	0.0018 (9)
C6	0.0393 (11)	0.0346 (12)	0.0308 (9)	−0.0001 (10)	0.0018 (7)	−0.0019 (8)
C7	0.0381 (11)	0.0332 (12)	0.0384 (10)	−0.0013 (10)	0.0015 (8)	−0.0001 (9)
C8	0.0378 (12)	0.0346 (13)	0.0571 (12)	0.0000 (11)	0.0006 (9)	−0.0002 (10)
C9	0.0384 (12)	0.0413 (14)	0.0562 (12)	0.0046 (11)	0.0001 (9)	−0.0029 (11)
C10	0.0400 (13)	0.0669 (19)	0.0812 (16)	0.0018 (13)	0.0068 (11)	−0.0049 (14)
N1	0.0402 (11)	0.0408 (12)	0.0702 (11)	0.0002 (9)	0.0112 (8)	0.0017 (9)
O1	0.0395 (9)	0.0458 (11)	0.0781 (10)	−0.0054 (8)	0.0105 (7)	0.0018 (8)
O2	0.0340 (9)	0.0818 (15)	0.1241 (15)	−0.0034 (9)	0.0039 (9)	−0.0057 (12)

Geometric parameters (Å, º) top

C1—C2	1.368 (3)	C7—N1	1.306 (3)
C1—C6	1.387 (3)	C7—C8	1.406 (3)
C1—H1	0.9300	C8—C9	1.322 (3)
C2—C3	1.373 (3)	C8—H8	0.9300
C2—H2	0.9300	C9—O1	1.351 (3)
C3—C4	1.373 (3)	C9—C10	1.476 (3)
C3—H3	0.9300	C10—O2	1.410 (3)
C4—C5	1.373 (3)	C10—H10A	0.9700
C4—H4	0.9300	C10—H10B	0.9700
C5—C6	1.383 (3)	N1—O1	1.406 (2)
C5—H5	0.9300	O2—H2B	0.8561
C6—C7	1.466 (3)	O2—H2A	0.8798

C2—C1—C6	120.5 (2)	N1—C7—C6	120.73 (18)
C2—C1—H1	119.7	C8—C7—C6	128.09 (19)
C6—C1—H1	119.7	C9—C8—C7	105.4 (2)
C1—C2—C3	120.1 (2)	C9—C8—H8	127.3
C1—C2—H2	119.9	C7—C8—H8	127.3
C3—C2—H2	119.9	C8—C9—O1	110.0 (2)
C2—C3—C4	119.9 (2)	C8—C9—C10	133.2 (2)
C2—C3—H3	120.1	O1—C9—C10	116.5 (2)
C4—C3—H3	120.1	O2—C10—C9	114.7 (2)
C5—C4—C3	120.4 (2)	O2—C10—H10A	108.6
C5—C4—H4	119.8	C9—C10—H10A	108.6
C3—C4—H4	119.8	O2—C10—H10B	108.6
C4—C5—C6	120.1 (2)	C9—C10—H10B	108.6
C4—C5—H5	120.0	H10A—C10—H10B	107.6
C6—C5—H5	120.0	C7—N1—O1	105.53 (16)
C5—C6—C1	119.00 (19)	C9—O1—N1	107.91 (15)
C5—C6—C7	120.49 (19)	C10—O2—H2B	119.6
C1—C6—C7	120.46 (18)	C10—O2—H2A	96.2
N1—C7—C8	111.11 (19)	H2B—O2—H2A	84.0

C6—C1—C2—C3	−0.7 (3)	N1—C7—C8—C9	1.2 (2)
C1—C2—C3—C4	0.3 (3)	C6—C7—C8—C9	−175.60 (17)
C2—C3—C4—C5	0.4 (3)	C7—C8—C9—O1	−0.9 (2)
C3—C4—C5—C6	−0.7 (3)	C7—C8—C9—C10	173.2 (2)
C4—C5—C6—C1	0.4 (3)	C8—C9—C10—O2	131.4 (3)
C4—C5—C6—C7	−177.04 (16)	O1—C9—C10—O2	−54.8 (3)
C2—C1—C6—C5	0.3 (3)	C8—C7—N1—O1	−1.0 (2)
C2—C1—C6—C7	177.73 (16)	C6—C7—N1—O1	176.11 (15)
C5—C6—C7—N1	−24.9 (3)	C8—C9—O1—N1	0.4 (2)
C1—C6—C7—N1	157.73 (18)	C10—C9—O1—N1	−174.81 (17)
C5—C6—C7—C8	151.63 (19)	C7—N1—O1—C9	0.4 (2)
C1—C6—C7—C8	−25.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O2ⁱ	0.86	1.89	2.669 (4)	151
O2—H2A···O2ⁱⁱ	0.88	2.09	2.677 (5)	124
C8—H8···N1ⁱⁱⁱ	0.93	2.61	3.542 (4)	177
C10—H10B···O2^iv	0.97	2.58	3.352 (4)	137

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y, −z+1/2; (iii) x, y+1, z; (iv) −x, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₀H₉NO₂
M_r	175.18
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	41.03 (4), 5.694 (5), 7.348 (7)
β (°)	98.51 (2)
V (Å³)	1698 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.55 × 0.45 × 0.02

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3328, 1500, 1182
R_int	0.059
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.119, 1.05
No. of reflections	1500
No. of parameters	118
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.23

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1999), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2B···O2ⁱ	0.86	1.89	2.669 (4)	150.7
O2—H2A···O2ⁱⁱ	0.88	2.09	2.677 (5)	123.5
C8—H8···N1ⁱⁱⁱ	0.93	2.61	3.542 (4)	177.4
C10—H10B···O2^iv	0.97	2.58	3.352 (4)	137.1

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, y, −z+1/2; (iii) x, y+1, z; (iv) −x, −y+2, −z+1.

Acknowledgements

The authors express sincere gratitude to Xi-Zhao Wang for valuable discussions on the preparation of this manuscript.

References

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