5-Amino-3-(4-pyrid­yl)isoxazole

Zheng Yao; Jian-Cheng Deng

doi:10.1107/S160053680706309X

. 2007 Dec 6;64(Pt 1):o131. doi: 10.1107/S160053680706309X

5-Amino-3-(4-pyridyl)isoxazole

Zheng Yao ^a, Jian-Cheng Deng ^a,^*

PMCID: PMC2915201 PMID: 21200696

Abstract

In the title compound, C₈H₇N₃O, there are two independent molecules in the asymmetric unit, in which the angles between the pyridine ring and the isoxazole ring are 35.8 (6) and 10.6 (2)°. The crystal packing is stabilized by N—H⋯N hydrogen bonds, which result in the molecules forming a two-dimensional supramolecular layer.

Related literature

The title compound was prepared according to a known procedure (Schmidt et al., 1966 ▶). For hydrogen-bond motif definitions, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₈H₇N₃O
M _r = 161.17
Monoclinic,
a = 14.6411 (13) Å
b = 10.9272 (10) Å
c = 10.0060 (9) Å
β = 106.9870 (10)°
V = 1531.0 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 187 (2) K
0.42 × 0.18 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.960, T _max = 0.990
8396 measured reflections
3018 independent reflections
2509 reflections with I > 2σ(I)
R _int = 0.025

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.120
S = 1.02
3018 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: SHELXTL (Bruker, 1997 ▶); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680706309X/bv2079sup1.cif

e-64-0o131-sup1.cif^{(16.4KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706309X/bv2079Isup2.hkl

e-64-0o131-Isup2.hkl^{(148.1KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯N4	0.88	2.09	2.970 (2)	177
N3—H3B⋯N2ⁱ	0.88	2.20	3.077 (2)	169
N6—H6A⋯N1ⁱⁱ	0.88	2.12	2.976 (2)	164
N6—H6B⋯N5ⁱⁱⁱ	0.88	2.09	2.970 (2)	174

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This work was supported by the National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Changchun, China.

supplementary crystallographic information

Comment

The title compound, (I), is an intermediate for our drug development program. Its structure is shown in Fig. 1. The asymmetric unit was formed by two independent molecules, in which the angles between the pyridine ring and the isoxazole ring are 35.8 (6)° and 10.6 (2)° respectively. Four types of N—H···N hydrogen bonds in the structure are present, which generate two rings, R₄⁴(18) and R₄⁴(28) (Bernstein et al., 1995). These hydrogen bonds extend the monomer into a two-dimensional supramolecular layer (Fig. 2 and Table 1).

Experimental

The title compound was prepared according to a known procedure (Schmidt et al., 1966). Single crystals suitable for X-ray diffraction were obtained by slow evaporation of a ethanol solution at room temperature.