5-Methyl-1,2-oxazole-3-carb­oxy­lic acid

Pan, M.-L.; Luo, Y.-H.; Li, J.-F.

doi:10.1107/S160053681103532X

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2545

https://doi.org/10.1107/S160053681103532X

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5-Methyl-1,2-oxazole-3-carboxylic acid

Mei-Ling Pan,^a ^* Yang-Hui Luo ^a and Jin-Feng Li ^a

^aOrdered Matter Science Research Center, College of Chemistry and Chemical Engineering, Southeast University, Nanjing 210096, People's Republic of China
^*Correspondence e-mail: chmsunbw@seu.edu.cn

(Received 21 July 2011; accepted 30 August 2011; online 3 September 2011)

In the crystal structure of the title compound, C₅H₅NO₃, all the non-H atoms are approximately coplanar: the carboxy O atoms deviating by 0.013 (2) and −0.075 (2) Å from the isoxazole ring plane. In the crystal, the molecules form inversion dimers linked by pairs of O—H⋯O hydrogen bonds and the dimers stack via π–π interactions [centroid–centroid distance = 3.234 (2) Å].

Related literature

The title compound is a potent inhibitor of the monoamine oxidase enzyme and multidentate ligand for transition metals, see: Birk & Weihe (2009 ).

Experimental

Crystal data

C₅H₅NO₃
M_r = 127.10
Triclinic, $[P \overline 1]$
a = 4.9125 (10) Å
b = 5.6909 (11) Å
c = 10.464 (2) Å
α = 82.21 (3)°
β = 79.72 (3)°
γ = 78.96 (3)°
V = 280.96 (10) Å³
Z = 2
Mo Kα radiation
μ = 0.13 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.975, T_max = 0.975
2923 measured reflections
1283 independent reflections
1052 reflections with I > 2σ(I)
R_int = 0.079

Refinement

R[F² > 2σ(F²)] = 0.084
wR(F²) = 0.230
S = 1.07
1283 reflections
83 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.98	1.68	2.650 (2)	170
Symmetry code: (i) -x+1, -y, -z+1.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ), ORTEP-3 for Windows (Farrugia, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S160053681103532X/jh2316sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053681103532X/jh2316Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S160053681103532X/jh2316Isup3.cml

checkCIF report

Comment top

5-Methylisoxazole-3-carboxylic acid is a potent inhibitor of the monoamine oxidase enzyme and excellent ligand for transition metals (Birk, et al.,2009) as well as other derivatives of isoxazole. As part of our interest in these compounds, we report here the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. All the non-H atoms of the title compound are located almost in one plane, as the atoms O1 and O2 are shifted just ca 0.0016Å out of the isoxazole ring plane.

The title compound formed dimer via intermolecular O—H···O hydrogen bonds and the dimers packed via π–π stacking interactions (3.234 Å).(Fig. 2).

Related literature top

The title compound is a potent inhibitor of the monoamine oxidase enzyme and excellent ligand for transition metals, see: Birk & Weihe (2009).

Experimental top

The title compound was purchased commercially. Crystals suitable for X-ray diffraction were obtained by slow evaporation of an ethanol solution.

Structure description top

The title compound formed dimer via intermolecular O—H···O hydrogen bonds and the dimers packed via π–π stacking interactions (3.234 Å).(Fig. 2).

The title compound is a potent inhibitor of the monoamine oxidase enzyme and excellent ligand for transition metals, see: Birk & Weihe (2009).

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. A packing view down the a axis showing the three dimensionnal network.Intermolecular hydrogen bonds are shown as dashed lines. H atoms have been omitted for the sake of clarity.

5-Methyl-1,2-oxazole-3-carboxylic acid top

Crystal data top

C₅H₅NO₃	Z = 2
M_r = 127.10	F(000) = 132
Triclinic, P1	D_x = 1.502 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.9125 (10) Å	Cell parameters from 1283 reflections
b = 5.6909 (11) Å	θ = 3.7–27.5°
c = 10.464 (2) Å	µ = 0.13 mm⁻¹
α = 82.21 (3)°	T = 293 K
β = 79.72 (3)°	Prism, colourless
γ = 78.96 (3)°	0.20 × 0.20 × 0.20 mm
V = 280.96 (10) Å³

Data collection top

Rigaku SCXmini diffractometer	1283 independent reflections
Radiation source: fine-focus sealed tube	1052 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.079
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.7°
CCD_Profile_fitting scans	h = −6→6
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −7→7
T_min = 0.975, T_max = 0.975	l = −13→13
2923 measured reflections

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)] = 0.084	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.230	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.1395P)²] where P = (F_o² + 2F_c²)/3
1283 reflections	(Δ/σ)_max < 0.001
83 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₅H₅NO₃	γ = 78.96 (3)°
M_r = 127.10	V = 280.96 (10) Å³
Triclinic, P1	Z = 2
a = 4.9125 (10) Å	Mo Kα radiation
b = 5.6909 (11) Å	µ = 0.13 mm⁻¹
c = 10.464 (2) Å	T = 293 K
α = 82.21 (3)°	0.20 × 0.20 × 0.20 mm
β = 79.72 (3)°

Data collection top

Rigaku SCXmini diffractometer	1283 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1052 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.975	R_int = 0.079
2923 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.084	1 restraint
wR(F²) = 0.230	H-atom parameters constrained
S = 1.07	Δρ_max = 0.31 e Å⁻³
1283 reflections	Δρ_min = −0.41 e Å⁻³
83 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
O3	−0.2313 (3)	0.3175 (2)	0.15660 (15)	0.0539 (5)
N1	−0.0692 (4)	0.1507 (3)	0.2343 (2)	0.0530 (6)
C2	0.0502 (4)	0.2811 (3)	0.29544 (17)	0.0401 (5)
C1	0.2432 (4)	0.1560 (3)	0.38652 (18)	0.0419 (5)
C3	−0.0274 (4)	0.5290 (3)	0.26092 (19)	0.0436 (5)
H3	0.0293	0.6551	0.2915	0.052*
C4	−0.2024 (4)	0.5436 (3)	0.17357 (18)	0.0428 (5)
O1	0.2945 (3)	−0.0687 (3)	0.40024 (16)	0.0560 (5)
C5	−0.3597 (5)	0.7439 (4)	0.0956 (2)	0.0541 (6)
H5A	−0.3371	0.7068	0.0071	0.081*
H5B	−0.2886	0.8892	0.0971	0.081*
H5C	−0.5553	0.7655	0.1323	0.081*
O2	0.3450 (3)	0.2937 (2)	0.44412 (15)	0.0551 (5)
H2	0.4849 (14)	0.1977 (10)	0.4948 (5)	0.083*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0681 (10)	0.0405 (9)	0.0617 (10)	−0.0087 (7)	−0.0357 (8)	−0.0030 (7)
N1	0.0638 (11)	0.0374 (10)	0.0650 (12)	−0.0080 (8)	−0.0332 (9)	−0.0017 (8)
C2	0.0447 (10)	0.0375 (10)	0.0398 (10)	−0.0074 (7)	−0.0116 (8)	−0.0032 (8)
C1	0.0446 (10)	0.0415 (10)	0.0408 (10)	−0.0082 (8)	−0.0103 (8)	−0.0028 (8)
C3	0.0496 (11)	0.0391 (11)	0.0455 (10)	−0.0088 (8)	−0.0139 (8)	−0.0058 (8)
C4	0.0495 (10)	0.0362 (10)	0.0446 (10)	−0.0066 (8)	−0.0137 (8)	−0.0036 (7)
O1	0.0646 (10)	0.0407 (9)	0.0655 (10)	−0.0029 (7)	−0.0291 (8)	0.0015 (7)
C5	0.0625 (13)	0.0463 (12)	0.0540 (12)	−0.0031 (9)	−0.0220 (10)	0.0009 (9)
O2	0.0624 (10)	0.0517 (10)	0.0581 (10)	−0.0081 (8)	−0.0295 (8)	−0.0057 (7)

Geometric parameters (Å, º) top

O3—C4	1.359 (2)	C3—C4	1.347 (3)
O3—N1	1.388 (2)	C3—H3	0.9300
N1—C2	1.317 (3)	C4—C5	1.482 (3)
C2—C3	1.404 (3)	C5—H5A	0.9600
C2—C1	1.481 (3)	C5—H5B	0.9600
C1—O1	1.249 (2)	C5—H5C	0.9600
C1—O2	1.270 (2)	O2—H2	0.9796

C4—O3—N1	109.46 (15)	C3—C4—O3	108.95 (18)
C2—N1—O3	104.75 (15)	C3—C4—C5	134.7 (2)
N1—C2—C3	112.28 (18)	O3—C4—C5	116.31 (18)
N1—C2—C1	118.65 (18)	C4—C5—H5A	109.6
C3—C2—C1	129.06 (18)	C4—C5—H5B	109.4
O1—C1—O2	125.6 (2)	H5A—C5—H5B	109.5
O1—C1—C2	119.38 (18)	C4—C5—H5C	109.5
O2—C1—C2	114.99 (17)	H5A—C5—H5C	109.5
C4—C3—C2	104.56 (17)	H5B—C5—H5C	109.5
C4—C3—H3	127.7	C1—O2—H2	109.6
C2—C3—H3	127.8

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.98	1.68	2.650 (2)	170

Symmetry code: (i) −x+1, −y, −z+1.

Experimental details

Crystal data
Chemical formula	C₅H₅NO₃
M_r	127.10
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	4.9125 (10), 5.6909 (11), 10.464 (2)
α, β, γ (°)	82.21 (3), 79.72 (3), 78.96 (3)
V (Å³)	280.96 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.13
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Rigaku SCXmini
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.975, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	2923, 1283, 1052
R_int	0.079
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.084, 0.230, 1.07
No. of reflections	1283
No. of parameters	83
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.41

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱ	0.98	1.68	2.650 (2)	170.1

Symmetry code: (i) −x+1, −y, −z+1.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (project 20671019).

References

Birk, T. & Weihe, H. (2009). J. Chem. Crystallogr. 39, 766–771. Web of Science CSD CrossRef CAS Google Scholar
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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar