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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o131.
Published online 2007 December 6. doi:  10.1107/S160053680706309X
PMCID: PMC2915201

5-Amino-3-(4-pyrid­yl)isoxazole

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 [triangle]). For hydrogen-bond motif definitions, see: Bernstein et al. (1995 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o131-scheme1.jpg

Experimental

Crystal data

  • C8H7N3O
  • M r = 161.17
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o131-efi1.jpg
  • 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 [triangle]) 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
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.23 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

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

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.

Refinement

H atoms were found on difference Fourier maps and refined as riding, with C—H distance of 0.95 Å and N—H distance of 0.88 Å, and with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
A view of (I), with the atom-labeling scheme and 30% probability displacement ellipsoids.
Fig. 2.
View of the three-dimensional supramolecular structure in (I). Dashed lines indicate hydrogen bonds.

Crystal data

C8H7N3OF000 = 672
Mr = 161.17Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 2830 reflections
a = 14.6411 (13) Åθ = 2.4–25.9º
b = 10.9272 (10) ŵ = 0.10 mm1
c = 10.0060 (9) ÅT = 187 (2) K
β = 106.9870 (10)ºBlock, colourless
V = 1531.0 (2) Å30.42 × 0.18 × 0.10 mm
Z = 8

Data collection

Bruker APEX CCD area-detector diffractometer3018 independent reflections
Radiation source: fine-focus sealed tube2509 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 187(2) Kθmax = 26.0º
[var phi] and ω scansθmin = 1.5º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −18→14
Tmin = 0.960, Tmax = 0.990k = −10→13
8396 measured reflectionsl = −12→12

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.043  w = 1/[σ2(Fo2) + (0.07P)2 + 0.2315P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.120(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.23 e Å3
3018 reflectionsΔρmin = −0.23 e Å3
218 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0047 (10)
Secondary atom site location: difference Fourier map

Special details

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)

xyzUiso*/Ueq
O10.46333 (7)0.85688 (9)0.20940 (11)0.0346 (3)
O20.00420 (8)0.88480 (9)0.77638 (11)0.0336 (3)
N10.79693 (9)0.83254 (13)−0.07659 (13)0.0383 (3)
N20.52225 (9)0.80823 (11)0.13072 (13)0.0337 (3)
N30.44141 (10)1.03237 (12)0.31848 (14)0.0388 (3)
H3A0.39460.99500.34070.047*
H3B0.45581.10860.34470.047*
N40.28672 (10)0.90935 (13)0.40458 (14)0.0398 (3)
N50.06798 (9)0.93321 (11)0.70626 (14)0.0359 (3)
N6−0.06051 (10)0.70441 (11)0.81376 (14)0.0377 (3)
H6A−0.09270.74580.86060.045*
H6B−0.06750.62460.80480.045*
C10.72429 (11)0.75481 (15)−0.08875 (15)0.0358 (4)
H10.72220.6830−0.14300.043*
C20.65244 (11)0.77244 (14)−0.02749 (15)0.0346 (4)
H20.60260.7141−0.03980.042*
C30.65383 (10)0.87660 (13)0.05244 (14)0.0271 (3)
C40.72841 (11)0.95824 (14)0.06540 (16)0.0368 (4)
H40.73221.03100.11880.044*
C50.79718 (12)0.93253 (15)−0.00027 (18)0.0419 (4)
H50.84770.98960.00960.050*
C60.58040 (10)0.89855 (13)0.12468 (13)0.0270 (3)
C70.49043 (11)0.97363 (13)0.24510 (14)0.0289 (3)
C80.56482 (10)1.00383 (13)0.19470 (14)0.0292 (3)
H80.59841.07930.20490.035*
C90.29569 (12)0.80896 (15)0.48351 (17)0.0399 (4)
H90.34610.75400.48450.048*
C100.23625 (11)0.77991 (14)0.56385 (16)0.0351 (4)
H100.24520.70650.61700.042*
C110.16304 (10)0.86076 (13)0.56504 (14)0.0286 (3)
C120.15291 (11)0.96543 (14)0.48390 (15)0.0331 (4)
H120.10381.02270.48200.040*
C130.21520 (12)0.98536 (15)0.40568 (16)0.0379 (4)
H130.20681.05700.34960.045*
C140.09696 (10)0.83758 (13)0.65003 (14)0.0272 (3)
C150.05754 (11)0.72799 (13)0.67909 (15)0.0310 (3)
H150.06890.64760.65140.037*
C16−0.00128 (10)0.76260 (13)0.75652 (14)0.0274 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0346 (6)0.0288 (6)0.0488 (6)−0.0019 (4)0.0251 (5)−0.0016 (5)
O20.0403 (6)0.0237 (5)0.0474 (6)−0.0025 (4)0.0294 (5)−0.0020 (4)
N10.0352 (7)0.0459 (8)0.0394 (7)0.0043 (6)0.0198 (6)0.0003 (6)
N20.0330 (7)0.0304 (7)0.0443 (7)0.0000 (5)0.0216 (6)−0.0034 (5)
N30.0443 (8)0.0306 (7)0.0545 (8)−0.0018 (6)0.0347 (7)−0.0025 (6)
N40.0369 (8)0.0452 (8)0.0452 (7)−0.0045 (6)0.0242 (6)−0.0018 (6)
N50.0415 (8)0.0270 (7)0.0502 (8)−0.0038 (6)0.0303 (6)0.0000 (6)
N60.0488 (8)0.0247 (7)0.0527 (8)−0.0031 (6)0.0353 (7)−0.0018 (6)
C10.0382 (9)0.0391 (9)0.0328 (8)0.0022 (7)0.0146 (7)−0.0053 (7)
C20.0331 (8)0.0370 (9)0.0361 (8)−0.0039 (7)0.0138 (7)−0.0038 (7)
C30.0270 (7)0.0287 (8)0.0268 (7)0.0030 (6)0.0098 (6)0.0026 (6)
C40.0364 (9)0.0340 (9)0.0458 (9)−0.0031 (7)0.0209 (7)−0.0060 (7)
C50.0382 (9)0.0418 (9)0.0538 (10)−0.0065 (7)0.0263 (8)−0.0063 (8)
C60.0251 (7)0.0283 (7)0.0284 (7)0.0005 (6)0.0088 (6)0.0043 (6)
C70.0321 (8)0.0258 (8)0.0313 (7)0.0020 (6)0.0129 (6)0.0030 (6)
C80.0308 (8)0.0269 (7)0.0343 (7)−0.0030 (6)0.0164 (6)−0.0006 (6)
C90.0351 (9)0.0421 (10)0.0491 (9)0.0051 (7)0.0225 (7)0.0015 (8)
C100.0353 (8)0.0328 (8)0.0417 (8)0.0037 (7)0.0181 (7)0.0040 (7)
C110.0270 (7)0.0300 (8)0.0312 (7)−0.0035 (6)0.0124 (6)−0.0026 (6)
C120.0336 (8)0.0314 (8)0.0398 (8)0.0011 (6)0.0193 (7)0.0023 (7)
C130.0431 (9)0.0347 (9)0.0423 (9)−0.0030 (7)0.0225 (7)0.0038 (7)
C140.0266 (7)0.0268 (7)0.0301 (7)0.0015 (6)0.0113 (6)0.0017 (6)
C150.0387 (8)0.0223 (7)0.0386 (8)0.0016 (6)0.0214 (7)0.0006 (6)
C160.0309 (7)0.0227 (7)0.0322 (7)0.0010 (6)0.0150 (6)0.0016 (6)

Geometric parameters (Å, °)

O1—C71.3527 (17)C3—C41.386 (2)
O1—N21.4295 (14)C3—C61.4798 (18)
O2—C161.3490 (17)C4—C51.382 (2)
O2—N51.4237 (14)C4—H40.9500
N1—C51.332 (2)C5—H50.9500
N1—C11.339 (2)C6—C81.3999 (19)
N2—C61.3164 (18)C7—C81.3677 (19)
N3—C71.3319 (18)C8—H80.9500
N3—H3A0.8800C9—C101.383 (2)
N3—H3B0.8800C9—H90.9500
N4—C91.336 (2)C10—C111.392 (2)
N4—C131.339 (2)C10—H100.9500
N5—C141.3145 (17)C11—C121.385 (2)
N6—C161.3322 (18)C11—C141.4847 (18)
N6—H6A0.8800C12—C131.3816 (19)
N6—H6B0.8800C12—H120.9500
C1—C21.377 (2)C13—H130.9500
C1—H10.9500C14—C151.3963 (19)
C2—C31.388 (2)C15—C161.3692 (19)
C2—H20.9500C15—H150.9500
C7—O1—N2108.58 (10)N3—C7—O1115.87 (13)
C16—O2—N5108.34 (10)N3—C7—C8134.62 (14)
C5—N1—C1116.20 (13)O1—C7—C8109.51 (12)
C6—N2—O1104.42 (11)C7—C8—C6104.48 (12)
C7—N3—H3A120.0C7—C8—H8127.8
C7—N3—H3B120.0C6—C8—H8127.8
H3A—N3—H3B120.0N4—C9—C10124.22 (15)
C9—N4—C13116.52 (13)N4—C9—H9117.9
C14—N5—O2104.82 (10)C10—C9—H9117.9
C16—N6—H6A120.0C9—C10—C11118.44 (14)
C16—N6—H6B120.0C9—C10—H10120.8
H6A—N6—H6B120.0C11—C10—H10120.8
N1—C1—C2124.11 (14)C12—C11—C10118.03 (13)
N1—C1—H1117.9C12—C11—C14120.03 (13)
C2—C1—H1117.9C10—C11—C14121.94 (13)
C1—C2—C3119.13 (14)C13—C12—C11119.13 (14)
C1—C2—H2120.4C13—C12—H12120.4
C3—C2—H2120.4C11—C12—H12120.4
C4—C3—C2117.40 (13)N4—C13—C12123.65 (15)
C4—C3—C6120.98 (13)N4—C13—H13118.2
C2—C3—C6121.60 (13)C12—C13—H13118.2
C5—C4—C3119.20 (14)N5—C14—C15112.83 (12)
C5—C4—H4120.4N5—C14—C11117.08 (12)
C3—C4—H4120.4C15—C14—C11130.08 (12)
N1—C5—C4123.96 (15)C16—C15—C14104.33 (12)
N1—C5—H5118.0C16—C15—H15127.8
C4—C5—H5118.0C14—C15—H15127.8
N2—C6—C8113.02 (12)N6—C16—O2115.30 (12)
N2—C6—C3118.22 (13)N6—C16—C15135.03 (14)
C8—C6—C3128.72 (13)O2—C16—C15109.67 (12)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N3—H3A···N40.882.092.970 (2)177
N3—H3B···N2i0.882.203.077 (2)169
N6—H6A···N1ii0.882.122.976 (2)164
N6—H6B···N5iii0.882.092.970 (2)174

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1, y, z+1; (iii) −x, y−1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2079).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Bruker (1997). SHELXTL Version 5.1. Bruker AXS Inc., Madison, Wisconsion, USA.
  • Bruker (1998). SMART Version 5.0. Bruker AXS Inc., Madison, Wisconsion, USA.
  • Bruker (2003). SAINT Version 6. Bruker AXS, Inc., Madison, Wisconsion, USA.
  • Schmidt, P., Eichenberger, K. & Wilhelm, M. (1966). US Patent 3 277 105.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (1997). SHELXS97 and SHELXL97 University of Göttingen, Germany.

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