3-[3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl]propanoic acid

Zhang, F.; Liu, F.; Chen, Q.; Dong, M.

doi:10.1107/S1600536810051639

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o193

https://doi.org/10.1107/S1600536810051639

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3-[3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl]propanoic acid

Fang Zhang,^a Fei Liu,^a ^* Qifan Chen ^b and Mingdong Dong ^b

^aCollege of Chemical Engineering & Materials, Eastern Liaoning University, No. 325 Wenhua Road, Yuanbao District, Dandong City, Liaoning Province 118003, People's Republic of China, and ^bExperiment Center, Eastern Liaoning University, No. 325 Wenhua Road, Yuanbao District, Dandong City, Liaoning Province 118003, People's Republic of China
^*Correspondence e-mail: berylliu8090@sina.com

(Received 25 November 2010; accepted 9 December 2010; online 18 December 2010)

In the title compound, C₁₀H₉N₃O₃, the benzene ring is almost coplanar with the heterocyclic ring, making a dihedral angle of 11.3 (1)°. The plane of the carboxyl group is rotated by 8.4 (2)° with respect to the 1,2,4-oxadiazole ring plane. The aliphatic chain exhibits an extended conformation. In the crystal, molecules are liked through intermolecular O—H⋯N bonds, forming a chain structure along the c axis.

Related literature

For the biological activity of 1,2,4-oxadiazoles, see: Jakopin & Dolenc, 2008 ). For the use of this heterocycle as a core for luminescent liquid crystals, see: Gallardo et al. (2008 ). For related structures, see: Santos et al. (2009 ); Wang et al. (2006 , 2007 )

Experimental

Crystal data

C₁₀H₉N₃O₃
M_r = 219.20
Orthorhombic, P n a 2₁
a = 6.1298 (12) Å
b = 6.8194 (14) Å
c = 23.426 (5) Å
V = 979.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.33 × 0.22 × 0.21 mm

Data collection

Siemens P4 diffractometer
8147 measured reflections
1138 independent reflections
884 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.083
S = 1.00
1138 reflections
146 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N3ⁱ	0.82	1.89	2.704 (3)	172
Symmetry code: (i) $[-x+1, -y+1, z+{\script{1\over 2}}]$ .

Data collection: XSCANS (Bruker, 2003 ); cell refinement: XSCANS; data reduction: XSCANS and SHELXTL (Sheldrick, 2008 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810051639/fk2032sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051639/fk2032Isup2.hkl

checkCIF report

Comment top

1,2,4-Oxadiazoles are well known compounds, which exhibit a large number of biological activities (Jakopin & Dolenc, 2008). Recently, the use of this heterocycle as core for luminescent liquid crystals has also been described (Gallardo et al., 2008). Here we report the structure of title compound (Fig. 1), the benzene ring is almost coplanar with the heterocyclic ring, making a dihedral angle of 11.3 (1) °. The torsion angle N2—C5—C6—C10 between the pyridine ring attached to C-5 of the 1,2,4-oxadiazole system is -8.0 (3) °, both rings are almost coplanar. The C-4 side-chain containing a carboxylic acid group shows a zigzag arrangement, having the torsion angle C1—C2—C3—C4 of -178.0 (2) °. In addition, the plane of the carboxylic group is also rotated by 8.4 (2) ° with respect to the mean plane of the 1,2,4-oxadiazole five-membered ring. This makes the molecular structure to be slightly twisted. In the crystal structure, molecules are liked through intermolecular O—H···N, forming a one-dimensional chain structure along the crystallographic c axis.

Related literature top

For the biological activity of 1,2,4-oxadiazoles, see: Jakopin & Dolenc, 2008). For the use of this heterocycle as a core for luminescent liquid crystals, see: Gallardo et al. (2008). For related structures, see: Santos et al. (2009); Wang et al. (2006, 2007)

Experimental top

To a solution of nitrile (0.2 mol) in ethanol (20 mL) was added hydroxylamine hydrochloride (0.4 mol) in water (40 mL). Then anhydrous sodium carbonate(0.4 mol) in water (120 mL) was slowly added to the resulting solution and the mixture was stirred at 358k for 5 h. The mixture was then concentrated under vacuum to evaporate some water. The resulting suspension was filtered, the amidoxime solid formed was washed with cold water, dried under vacuum. A thoroughly triturated mixture of amidoxime (0.04 mol) and succinic anhydride (0.08 mol) was heated in an oily bath to 403k and kept at this temperature for 4 h. The reaction mixture was cooled to room temperature, and the product was washed with cold water, filtered, and recrystallized from ethanol. Block-shaped crystals suitable for X-ray diffraction were obtained from methanol.

Structure description top

For the biological activity of 1,2,4-oxadiazoles, see: Jakopin & Dolenc, 2008). For the use of this heterocycle as a core for luminescent liquid crystals, see: Gallardo et al. (2008). For related structures, see: Santos et al. (2009); Wang et al. (2006, 2007)

Computing details top

Data collection: XSCANS (Bruker, 2003); cell refinement: XSCANS (Bruker, 2003); data reduction: XSCANS (Bruker, 2003) and SHELXTL (Sheldrick, 2008); 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 (Sheldrick, 2008).

Figures top

Fig. 1. Structure of the title compound showing 50% probability displacement ellipsoids.

3-[3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl]propanoic acid top

Crystal data top

C₁₀H₉N₃O₃	F(000) = 456
M_r = 219.20	D_x = 1.487 Mg m⁻³
Orthorhombic, Pna2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 6383 reflections
a = 6.1298 (12) Å	θ = 3.1–27.5°
b = 6.8194 (14) Å	µ = 0.11 mm⁻¹
c = 23.426 (5) Å	T = 293 K
V = 979.2 (3) Å³	Block, colourless
Z = 4	0.33 × 0.22 × 0.21 mm

Data collection top

Bruker P4 diffractometer	884 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.049
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −6→7
8147 measured reflections	k = −8→8
1138 independent reflections	l = −30→30

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)] = 0.034	Hydrogen site location: geom and difmap
wR(F²) = 0.083	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0487P)²] where P = (F_o² + 2F_c²)/3
1138 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.14 e Å⁻³
1 restraint	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₀H₉N₃O₃	V = 979.2 (3) Å³
M_r = 219.20	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 6.1298 (12) Å	µ = 0.11 mm⁻¹
b = 6.8194 (14) Å	T = 293 K
c = 23.426 (5) Å	0.33 × 0.22 × 0.21 mm

Data collection top

Bruker P4 diffractometer	884 reflections with I > 2σ(I)
8147 measured reflections	R_int = 0.049
1138 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	1 restraint
wR(F²) = 0.083	H-atom parameters constrained
S = 1.00	Δρ_max = 0.14 e Å⁻³
1138 reflections	Δρ_min = −0.16 e Å⁻³
146 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	0.8809 (3)	0.4377 (3)	0.16313 (7)	0.0450 (5)
O1	0.4239 (4)	0.4072 (4)	0.33554 (8)	0.0628 (6)
H1	0.3237	0.4277	0.3579	0.094*
O2	0.2140 (4)	0.5819 (3)	0.27757 (9)	0.0681 (7)
N3	0.8817 (4)	0.5436 (3)	−0.08242 (9)	0.0468 (6)
C10	0.8297 (5)	0.5499 (4)	−0.02742 (11)	0.0412 (6)
H10	0.6895	0.5885	−0.0173	0.049*
N2	0.6960 (4)	0.5622 (3)	0.09157 (9)	0.0394 (5)
N1	1.0181 (4)	0.4195 (3)	0.11489 (9)	0.0461 (5)
C6	0.9757 (4)	0.5012 (4)	0.01552 (11)	0.0358 (5)
C5	0.8992 (4)	0.4978 (3)	0.07499 (10)	0.0346 (5)
C1	0.3807 (5)	0.4921 (4)	0.28656 (12)	0.0430 (6)
C2	0.5595 (4)	0.4565 (4)	0.24436 (11)	0.0426 (6)
H2A	0.5711	0.3167	0.2373	0.051*
H2B	0.6967	0.5002	0.2606	0.051*
C3	0.5225 (5)	0.5608 (4)	0.18853 (10)	0.0427 (6)
H3A	0.3826	0.5204	0.1731	0.051*
H3B	0.5153	0.7008	0.1956	0.051*
C8	1.2425 (5)	0.4437 (4)	−0.05639 (12)	0.0491 (7)
H8	1.3826	0.4088	−0.0677	0.059*
C7	1.1881 (4)	0.4503 (4)	0.00047 (12)	0.0449 (6)
H7	1.2912	0.4214	0.0284	0.054*
C4	0.6937 (4)	0.5226 (3)	0.14541 (10)	0.0358 (5)
C9	1.0850 (5)	0.4898 (4)	−0.09637 (13)	0.0497 (7)
H9	1.1220	0.4832	−0.1348	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0460 (11)	0.0605 (10)	0.0285 (9)	0.0084 (8)	−0.0026 (8)	0.0037 (8)
O1	0.0615 (14)	0.0953 (16)	0.0315 (10)	0.0191 (11)	0.0058 (9)	0.0162 (10)
O2	0.0625 (15)	0.0933 (16)	0.0484 (13)	0.0305 (12)	0.0078 (11)	0.0187 (11)
N3	0.0530 (14)	0.0543 (12)	0.0331 (12)	−0.0001 (10)	0.0009 (10)	0.0043 (10)
C10	0.0439 (18)	0.0467 (13)	0.0329 (13)	0.0034 (12)	−0.0010 (11)	0.0005 (11)
N2	0.0409 (11)	0.0462 (11)	0.0311 (11)	0.0030 (9)	−0.0008 (10)	0.0040 (9)
N1	0.0466 (12)	0.0580 (14)	0.0336 (11)	0.0079 (10)	0.0017 (10)	0.0048 (9)
C6	0.0411 (14)	0.0344 (10)	0.0319 (12)	−0.0020 (11)	−0.0028 (11)	0.0010 (9)
C5	0.0388 (13)	0.0340 (11)	0.0310 (12)	−0.0018 (11)	−0.0043 (11)	0.0008 (9)
C1	0.0473 (17)	0.0506 (14)	0.0311 (13)	−0.0015 (13)	−0.0036 (12)	0.0005 (10)
C2	0.0437 (15)	0.0525 (14)	0.0316 (13)	0.0027 (10)	−0.0015 (12)	0.0018 (11)
C3	0.0460 (15)	0.0503 (13)	0.0317 (13)	0.0066 (12)	0.0007 (12)	0.0021 (11)
C8	0.0450 (17)	0.0503 (16)	0.0521 (18)	−0.0005 (12)	0.0116 (14)	−0.0025 (12)
C7	0.0399 (15)	0.0470 (14)	0.0479 (17)	0.0019 (12)	−0.0022 (13)	0.0039 (12)
C4	0.0382 (14)	0.0361 (11)	0.0332 (14)	0.0011 (10)	−0.0050 (10)	−0.0013 (10)
C9	0.0575 (19)	0.0544 (15)	0.0371 (15)	−0.0021 (14)	0.0090 (13)	0.0014 (12)

Geometric parameters (Å, º) top

O3—C4	1.351 (3)	C6—C5	1.470 (4)
O3—N1	1.414 (3)	C1—C2	1.496 (4)
O1—C1	1.312 (3)	C2—C3	1.506 (3)
O1—H1	0.8200	C2—H2A	0.9700
O2—C1	1.210 (3)	C2—H2B	0.9700
N3—C10	1.328 (4)	C3—C4	1.480 (3)
N3—C9	1.340 (4)	C3—H3A	0.9700
C10—C6	1.387 (4)	C3—H3B	0.9700
C10—H10	0.9300	C8—C7	1.374 (4)
N2—C4	1.290 (3)	C8—C9	1.381 (4)
N2—C5	1.377 (3)	C8—H8	0.9300
N1—C5	1.300 (3)	C7—H7	0.9300
C6—C7	1.393 (4)	C9—H9	0.9300

C4—O3—N1	107.29 (18)	C3—C2—H2B	109.0
C1—O1—H1	109.5	H2A—C2—H2B	107.8
C10—N3—C9	117.9 (2)	C4—C3—C2	113.7 (2)
N3—C10—C6	122.8 (3)	C4—C3—H3A	108.8
N3—C10—H10	118.6	C2—C3—H3A	108.8
C6—C10—H10	118.6	C4—C3—H3B	108.8
C4—N2—C5	102.6 (2)	C2—C3—H3B	108.8
C5—N1—O3	101.84 (19)	H3A—C3—H3B	107.7
C10—C6—C7	118.6 (2)	C7—C8—C9	118.7 (3)
C10—C6—C5	119.1 (2)	C7—C8—H8	120.6
C7—C6—C5	122.3 (2)	C9—C8—H8	120.6
N1—C5—N2	115.8 (2)	C8—C7—C6	118.7 (2)
N1—C5—C6	120.6 (2)	C8—C7—H7	120.6
N2—C5—C6	123.4 (2)	C6—C7—H7	120.6
O2—C1—O1	123.1 (3)	N2—C4—O3	112.4 (2)
O2—C1—C2	125.9 (3)	N2—C4—C3	129.6 (3)
O1—C1—C2	111.0 (2)	O3—C4—C3	117.9 (2)
C1—C2—C3	112.8 (2)	N3—C9—C8	123.2 (3)
C1—C2—H2A	109.0	N3—C9—H9	118.4
C3—C2—H2A	109.0	C8—C9—H9	118.4
C1—C2—H2B	109.0

C9—N3—C10—C6	−0.8 (4)	O1—C1—C2—C3	−176.8 (2)
C4—O3—N1—C5	1.1 (2)	C1—C2—C3—C4	−178.1 (2)
N3—C10—C6—C7	2.4 (4)	C9—C8—C7—C6	0.7 (4)
N3—C10—C6—C5	−175.4 (2)	C10—C6—C7—C8	−2.3 (4)
O3—N1—C5—N2	−1.3 (3)	C5—C6—C7—C8	175.4 (2)
O3—N1—C5—C6	−176.9 (2)	C5—N2—C4—O3	−0.2 (3)
C4—N2—C5—N1	1.0 (3)	C5—N2—C4—C3	178.2 (2)
C4—N2—C5—C6	176.4 (2)	N1—O3—C4—N2	−0.6 (3)
C10—C6—C5—N1	167.5 (2)	N1—O3—C4—C3	−179.1 (2)
C7—C6—C5—N1	−10.2 (3)	C2—C3—C4—N2	168.1 (2)
C10—C6—C5—N2	−7.7 (3)	C2—C3—C4—O3	−13.6 (3)
C7—C6—C5—N2	174.6 (2)	C10—N3—C9—C8	−0.9 (4)
O2—C1—C2—C3	5.1 (4)	C7—C8—C9—N3	0.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ⁱ	0.82	1.89	2.704 (3)	172

Symmetry code: (i) −x+1, −y+1, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₉N₃O₃
M_r	219.20
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	6.1298 (12), 6.8194 (14), 23.426 (5)
V (Å³)	979.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.33 × 0.22 × 0.21

Data collection
Diffractometer	Bruker P4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8147, 1138, 884
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.083, 1.00
No. of reflections	1138
No. of parameters	146
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.16

Computer programs: XSCANS (Bruker, 2003) and SHELXTL (Sheldrick, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N3ⁱ	0.82	1.89	2.704 (3)	172

Symmetry code: (i) −x+1, −y+1, z+1/2.

Acknowledgements

The authors gratefully acknowledge financial support from the Education Department of Liaoning Province (2009 A 265) and Liaoning University.

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