5-Amino-3-methyl-1,2-oxazole-4-carbonitrile.

In the title compound, C(5)H(5)N(3)O, the isoxazole ring is essentially planar, with a maximum deviation of 0.007 (1) Å from the least-squares plane. The N atom of the amine group exhibits sp(2) character (sum of bond angles around this atom = 358°). In the crystal, mol-ecules are aggregated by two kinds of N-H⋯N hydrogen bonds into fused R(2) (2)(12) and R(6) (6)(26) rings, forming a slightly puckered two-dimensional array lying parallel to (101).

Related literature

For the biological activities of isoxazole derivatives, see: Mantegani et al. (2011 ▶); Ali et al. (2011 ▶); Panda et al. (2009 ▶); Özdemir et al. (2007 ▶); Banerjee et al. (1994 ▶); Makoto et al. (2011 ▶). For background to push–pull nitriles, see: Ziao et al. (2001 ▶); Hao et al. (2005 ▶). For hydrogen-bond motif definitions, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C5H5N3O

M = 123.12

Monoclinic,

a = 3.8779 (2) Å

b = 18.8518 (11) Å

c = 8.2015 (4) Å

β = 100.780 (2)°

V = 588.99 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.56 × 0.26 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.674, T max = 0.745

5275 measured reflections

1277 independent reflections

1072 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.107

S = 1.07

1277 reflections

91 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.19 e Å−3

Δρmin = −0.16 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XPW (Siemens, 1996 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶) and enCIFer (Allen et al., 2004 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032667/gk2513sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032667/gk2513Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032667/gk2513Isup3.cml

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

C5H5N3O	F(000) = 256
Mr = 123.12	Dx = 1.388 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2187 reflections
a = 3.8779 (2) Å	θ = 2.8–26.2°
b = 18.8518 (11) Å	µ = 0.10 mm−1
c = 8.2015 (4) Å	T = 296 K
β = 100.780 (2)°	Irregular, colourless
V = 588.99 (5) Å3	0.56 × 0.26 × 0.20 mm
Z = 4

Bruker APEXII CCD diffractometer	1277 independent reflections
Radiation source: fine-focus sealed tube	1072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 27.0°, θmin = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −4→4
Tmin = 0.674, Tmax = 0.745	k = −24→23
5275 measured reflections	l = −10→10

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0631P)2 + 0.0596P] where P = (Fo2 + 2Fc2)/3
1277 reflections	(Δ/σ)max = 0.001
91 parameters	Δρmax = 0.19 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
O1	0.8940 (2)	0.77984 (4)	0.37710 (11)	0.0430 (3)
C2	0.8212 (3)	0.89315 (6)	0.30725 (13)	0.0343 (3)
N1	0.9900 (3)	0.78822 (6)	0.21727 (13)	0.0454 (3)
N2	0.6888 (4)	0.84546 (6)	0.57048 (14)	0.0463 (3)
N3	0.6449 (4)	1.02356 (6)	0.30830 (16)	0.0577 (4)
C4	0.7269 (3)	0.96534 (6)	0.30883 (14)	0.0384 (3)
C3	0.9420 (3)	0.85487 (7)	0.17972 (14)	0.0381 (3)
C5	1.0051 (4)	0.88260 (8)	0.01801 (16)	0.0518 (4)
H5A	1.1058	0.8459	−0.0394	0.078*
H5B	1.1637	0.9221	0.0372	0.078*
H5C	0.7866	0.8977	−0.0482	0.078*
C1	0.7919 (3)	0.84280 (6)	0.42663 (14)	0.0347 (3)
H2A	0.647 (4)	0.8074 (10)	0.617 (2)	0.063 (5)*
H2B	0.610 (4)	0.8842 (10)	0.608 (2)	0.061 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0636 (6)	0.0243 (4)	0.0437 (5)	0.0043 (4)	0.0167 (4)	−0.0011 (3)
C2	0.0426 (6)	0.0264 (6)	0.0346 (6)	0.0016 (4)	0.0092 (5)	−0.0006 (4)
N1	0.0611 (7)	0.0367 (6)	0.0413 (6)	0.0057 (5)	0.0168 (5)	−0.0060 (4)
N2	0.0752 (8)	0.0257 (6)	0.0434 (6)	0.0018 (5)	0.0256 (6)	0.0023 (4)
N3	0.0844 (10)	0.0318 (6)	0.0616 (8)	0.0114 (6)	0.0260 (7)	0.0054 (5)
C4	0.0504 (7)	0.0306 (7)	0.0367 (6)	0.0018 (5)	0.0145 (5)	0.0021 (4)
C3	0.0420 (6)	0.0358 (6)	0.0369 (6)	0.0029 (5)	0.0083 (5)	−0.0038 (5)
C5	0.0622 (8)	0.0581 (9)	0.0384 (7)	0.0072 (7)	0.0180 (6)	0.0027 (6)
C1	0.0440 (6)	0.0237 (6)	0.0369 (6)	−0.0003 (4)	0.0090 (5)	−0.0026 (4)

O1—C1	1.3383 (13)	N2—H2A	0.842 (19)
O1—N1	1.4367 (13)	N2—H2B	0.870 (18)
C2—C1	1.3836 (16)	N3—C4	1.1424 (16)
C2—C4	1.4098 (16)	C3—C5	1.4877 (17)
C2—C3	1.4204 (16)	C5—H5A	0.9600
N1—C3	1.2988 (16)	C5—H5B	0.9600
N2—C1	1.3154 (16)	C5—H5C	0.9600
C1—O1—N1	108.74 (8)	C2—C3—C5	127.57 (12)
C1—C2—C4	126.86 (10)	C3—C5—H5A	109.5
C1—C2—C3	104.75 (10)	C3—C5—H5B	109.5
C4—C2—C3	128.25 (11)	H5A—C5—H5B	109.5
C3—N1—O1	105.83 (9)	C3—C5—H5C	109.5
C1—N2—H2A	119.3 (12)	H5A—C5—H5C	109.5
C1—N2—H2B	122.4 (11)	H5B—C5—H5C	109.5
H2A—N2—H2B	116.3 (16)	N2—C1—O1	117.57 (10)
N3—C4—C2	178.79 (15)	N2—C1—C2	133.44 (11)
N1—C3—C2	111.67 (11)	O1—C1—C2	109.00 (10)
N1—C3—C5	120.74 (11)
C1—O1—N1—C3	0.14 (14)	N1—O1—C1—N2	179.10 (11)
O1—N1—C3—C2	0.70 (14)	N1—O1—C1—C2	−0.94 (13)
O1—N1—C3—C5	−178.01 (10)	C4—C2—C1—N2	−2.8 (2)
C1—C2—C3—N1	−1.26 (14)	C3—C2—C1—N2	−178.75 (15)
C4—C2—C3—N1	−177.17 (12)	C4—C2—C1—O1	177.29 (12)
C1—C2—C3—C5	177.35 (12)	C3—C2—C1—O1	1.31 (13)
C4—C2—C3—C5	1.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.842 (19)	2.118 (19)	2.9567 (16)	174.2 (16)
N2—H2B···N3ii	0.870 (18)	2.174 (18)	3.0402 (17)	173.8 (15)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.842 (19)	2.118 (19)	2.9567 (16)	174.2 (16)
N2—H2B⋯N3ii	0.870 (18)	2.174 (18)	3.0402 (17)	173.8 (15)

Symmetry codes: (i) ; (ii) .