organic compounds
5-Amino-3-(4-pyridyl)isoxazole
aCollege of Chemistry, Xiangtan University, Hunan 411105, People's Republic of China
*Correspondence e-mail: djcwye@163.com
In the title compound, C8H7N3O, there are two independent molecules in the 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
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Refinement
|
Data collection: SMART (Bruker, 1998); cell 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.
Supporting information
https://doi.org/10.1107/S160053680706309X/bv2079sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706309X/bv2079Isup2.hkl
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.
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).
The title compound, (I), is an intermediate for our drug development program. Its structure is shown in Fig. 1. The
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).The title compound was prepared according to a known procedure (Schmidt et al., 1966). For hydrogen-bond motif definitions, see: Bernstein et al. (1995).
Data collection: SMART (Bruker, 1998); cell
SMART (Bruker, 1998); data reduction: SAINT (Bruker, 2003); 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 (Bruker, 1997).C8H7N3O | F(000) = 672 |
Mr = 161.17 | Dx = 1.398 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2830 reflections |
a = 14.6411 (13) Å | θ = 2.4–25.9° |
b = 10.9272 (10) Å | µ = 0.10 mm−1 |
c = 10.0060 (9) Å | T = 187 K |
β = 106.987 (1)° | Block, colourless |
V = 1531.0 (2) Å3 | 0.42 × 0.18 × 0.10 mm |
Z = 8 |
Bruker APEX CCD area-detector diffractometer | 3018 independent reflections |
Radiation source: fine-focus sealed tube | 2509 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 26.0°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→14 |
Tmin = 0.960, Tmax = 0.990 | k = −10→13 |
8396 measured reflections | l = −12→12 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.07P)2 + 0.2315P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
3018 reflections | Δρmax = 0.23 e Å−3 |
218 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0047 (10) |
C8H7N3O | V = 1531.0 (2) Å3 |
Mr = 161.17 | Z = 8 |
Monoclinic, P21/c | Mo Kα radiation |
a = 14.6411 (13) Å | µ = 0.10 mm−1 |
b = 10.9272 (10) Å | T = 187 K |
c = 10.0060 (9) Å | 0.42 × 0.18 × 0.10 mm |
β = 106.987 (1)° |
Bruker APEX CCD area-detector diffractometer | 3018 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2509 reflections with I > 2σ(I) |
Tmin = 0.960, Tmax = 0.990 | Rint = 0.025 |
8396 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.23 e Å−3 |
3018 reflections | Δρmin = −0.23 e Å−3 |
218 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.46333 (7) | 0.85688 (9) | 0.20940 (11) | 0.0346 (3) | |
O2 | 0.00420 (8) | 0.88480 (9) | 0.77638 (11) | 0.0336 (3) | |
N1 | 0.79693 (9) | 0.83254 (13) | −0.07659 (13) | 0.0383 (3) | |
N2 | 0.52225 (9) | 0.80823 (11) | 0.13072 (13) | 0.0337 (3) | |
N3 | 0.44141 (10) | 1.03237 (12) | 0.31848 (14) | 0.0388 (3) | |
H3A | 0.3946 | 0.9950 | 0.3407 | 0.047* | |
H3B | 0.4558 | 1.1086 | 0.3447 | 0.047* | |
N4 | 0.28672 (10) | 0.90935 (13) | 0.40458 (14) | 0.0398 (3) | |
N5 | 0.06798 (9) | 0.93321 (11) | 0.70626 (14) | 0.0359 (3) | |
N6 | −0.06051 (10) | 0.70441 (11) | 0.81376 (14) | 0.0377 (3) | |
H6A | −0.0927 | 0.7458 | 0.8606 | 0.045* | |
H6B | −0.0675 | 0.6246 | 0.8048 | 0.045* | |
C1 | 0.72429 (11) | 0.75481 (15) | −0.08875 (15) | 0.0358 (4) | |
H1 | 0.7222 | 0.6830 | −0.1430 | 0.043* | |
C2 | 0.65244 (11) | 0.77244 (14) | −0.02749 (15) | 0.0346 (4) | |
H2 | 0.6026 | 0.7141 | −0.0398 | 0.042* | |
C3 | 0.65383 (10) | 0.87660 (13) | 0.05244 (14) | 0.0271 (3) | |
C4 | 0.72841 (11) | 0.95824 (14) | 0.06540 (16) | 0.0368 (4) | |
H4 | 0.7322 | 1.0310 | 0.1188 | 0.044* | |
C5 | 0.79718 (12) | 0.93253 (15) | −0.00027 (18) | 0.0419 (4) | |
H5 | 0.8477 | 0.9896 | 0.0096 | 0.050* | |
C6 | 0.58040 (10) | 0.89855 (13) | 0.12468 (13) | 0.0270 (3) | |
C7 | 0.49043 (11) | 0.97363 (13) | 0.24510 (14) | 0.0289 (3) | |
C8 | 0.56482 (10) | 1.00383 (13) | 0.19470 (14) | 0.0292 (3) | |
H8 | 0.5984 | 1.0793 | 0.2049 | 0.035* | |
C9 | 0.29569 (12) | 0.80896 (15) | 0.48351 (17) | 0.0399 (4) | |
H9 | 0.3461 | 0.7540 | 0.4845 | 0.048* | |
C10 | 0.23625 (11) | 0.77991 (14) | 0.56385 (16) | 0.0351 (4) | |
H10 | 0.2452 | 0.7065 | 0.6170 | 0.042* | |
C11 | 0.16304 (10) | 0.86076 (13) | 0.56504 (14) | 0.0286 (3) | |
C12 | 0.15291 (11) | 0.96543 (14) | 0.48390 (15) | 0.0331 (4) | |
H12 | 0.1038 | 1.0227 | 0.4820 | 0.040* | |
C13 | 0.21520 (12) | 0.98536 (15) | 0.40568 (16) | 0.0379 (4) | |
H13 | 0.2068 | 1.0570 | 0.3496 | 0.045* | |
C14 | 0.09696 (10) | 0.83758 (13) | 0.65003 (14) | 0.0272 (3) | |
C15 | 0.05754 (11) | 0.72799 (13) | 0.67909 (15) | 0.0310 (3) | |
H15 | 0.0689 | 0.6476 | 0.6514 | 0.037* | |
C16 | −0.00128 (10) | 0.76260 (13) | 0.75652 (14) | 0.0274 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0346 (6) | 0.0288 (6) | 0.0488 (6) | −0.0019 (4) | 0.0251 (5) | −0.0016 (5) |
O2 | 0.0403 (6) | 0.0237 (5) | 0.0474 (6) | −0.0025 (4) | 0.0294 (5) | −0.0020 (4) |
N1 | 0.0352 (7) | 0.0459 (8) | 0.0394 (7) | 0.0043 (6) | 0.0198 (6) | 0.0003 (6) |
N2 | 0.0330 (7) | 0.0304 (7) | 0.0443 (7) | 0.0000 (5) | 0.0216 (6) | −0.0034 (5) |
N3 | 0.0443 (8) | 0.0306 (7) | 0.0545 (8) | −0.0018 (6) | 0.0347 (7) | −0.0025 (6) |
N4 | 0.0369 (8) | 0.0452 (8) | 0.0452 (7) | −0.0045 (6) | 0.0242 (6) | −0.0018 (6) |
N5 | 0.0415 (8) | 0.0270 (7) | 0.0502 (8) | −0.0038 (6) | 0.0303 (6) | 0.0000 (6) |
N6 | 0.0488 (8) | 0.0247 (7) | 0.0527 (8) | −0.0031 (6) | 0.0353 (7) | −0.0018 (6) |
C1 | 0.0382 (9) | 0.0391 (9) | 0.0328 (8) | 0.0022 (7) | 0.0146 (7) | −0.0053 (7) |
C2 | 0.0331 (8) | 0.0370 (9) | 0.0361 (8) | −0.0039 (7) | 0.0138 (7) | −0.0038 (7) |
C3 | 0.0270 (7) | 0.0287 (8) | 0.0268 (7) | 0.0030 (6) | 0.0098 (6) | 0.0026 (6) |
C4 | 0.0364 (9) | 0.0340 (9) | 0.0458 (9) | −0.0031 (7) | 0.0209 (7) | −0.0060 (7) |
C5 | 0.0382 (9) | 0.0418 (9) | 0.0538 (10) | −0.0065 (7) | 0.0263 (8) | −0.0063 (8) |
C6 | 0.0251 (7) | 0.0283 (7) | 0.0284 (7) | 0.0005 (6) | 0.0088 (6) | 0.0043 (6) |
C7 | 0.0321 (8) | 0.0258 (8) | 0.0313 (7) | 0.0020 (6) | 0.0129 (6) | 0.0030 (6) |
C8 | 0.0308 (8) | 0.0269 (7) | 0.0343 (7) | −0.0030 (6) | 0.0164 (6) | −0.0006 (6) |
C9 | 0.0351 (9) | 0.0421 (10) | 0.0491 (9) | 0.0051 (7) | 0.0225 (7) | 0.0015 (8) |
C10 | 0.0353 (8) | 0.0328 (8) | 0.0417 (8) | 0.0037 (7) | 0.0181 (7) | 0.0040 (7) |
C11 | 0.0270 (7) | 0.0300 (8) | 0.0312 (7) | −0.0035 (6) | 0.0124 (6) | −0.0026 (6) |
C12 | 0.0336 (8) | 0.0314 (8) | 0.0398 (8) | 0.0011 (6) | 0.0193 (7) | 0.0023 (7) |
C13 | 0.0431 (9) | 0.0347 (9) | 0.0423 (9) | −0.0030 (7) | 0.0225 (7) | 0.0038 (7) |
C14 | 0.0266 (7) | 0.0268 (7) | 0.0301 (7) | 0.0015 (6) | 0.0113 (6) | 0.0017 (6) |
C15 | 0.0387 (8) | 0.0223 (7) | 0.0386 (8) | 0.0016 (6) | 0.0214 (7) | 0.0006 (6) |
C16 | 0.0309 (7) | 0.0227 (7) | 0.0322 (7) | 0.0010 (6) | 0.0150 (6) | 0.0016 (6) |
O1—C7 | 1.3527 (17) | C3—C4 | 1.386 (2) |
O1—N2 | 1.4295 (14) | C3—C6 | 1.4798 (18) |
O2—C16 | 1.3490 (17) | C4—C5 | 1.382 (2) |
O2—N5 | 1.4237 (14) | C4—H4 | 0.9500 |
N1—C5 | 1.332 (2) | C5—H5 | 0.9500 |
N1—C1 | 1.339 (2) | C6—C8 | 1.3999 (19) |
N2—C6 | 1.3164 (18) | C7—C8 | 1.3677 (19) |
N3—C7 | 1.3319 (18) | C8—H8 | 0.9500 |
N3—H3A | 0.8800 | C9—C10 | 1.383 (2) |
N3—H3B | 0.8800 | C9—H9 | 0.9500 |
N4—C9 | 1.336 (2) | C10—C11 | 1.392 (2) |
N4—C13 | 1.339 (2) | C10—H10 | 0.9500 |
N5—C14 | 1.3145 (17) | C11—C12 | 1.385 (2) |
N6—C16 | 1.3322 (18) | C11—C14 | 1.4847 (18) |
N6—H6A | 0.8800 | C12—C13 | 1.3816 (19) |
N6—H6B | 0.8800 | C12—H12 | 0.9500 |
C1—C2 | 1.377 (2) | C13—H13 | 0.9500 |
C1—H1 | 0.9500 | C14—C15 | 1.3963 (19) |
C2—C3 | 1.388 (2) | C15—C16 | 1.3692 (19) |
C2—H2 | 0.9500 | C15—H15 | 0.9500 |
C7—O1—N2 | 108.58 (10) | N3—C7—O1 | 115.87 (13) |
C16—O2—N5 | 108.34 (10) | N3—C7—C8 | 134.62 (14) |
C5—N1—C1 | 116.20 (13) | O1—C7—C8 | 109.51 (12) |
C6—N2—O1 | 104.42 (11) | C7—C8—C6 | 104.48 (12) |
C7—N3—H3A | 120.0 | C7—C8—H8 | 127.8 |
C7—N3—H3B | 120.0 | C6—C8—H8 | 127.8 |
H3A—N3—H3B | 120.0 | N4—C9—C10 | 124.22 (15) |
C9—N4—C13 | 116.52 (13) | N4—C9—H9 | 117.9 |
C14—N5—O2 | 104.82 (10) | C10—C9—H9 | 117.9 |
C16—N6—H6A | 120.0 | C9—C10—C11 | 118.44 (14) |
C16—N6—H6B | 120.0 | C9—C10—H10 | 120.8 |
H6A—N6—H6B | 120.0 | C11—C10—H10 | 120.8 |
N1—C1—C2 | 124.11 (14) | C12—C11—C10 | 118.03 (13) |
N1—C1—H1 | 117.9 | C12—C11—C14 | 120.03 (13) |
C2—C1—H1 | 117.9 | C10—C11—C14 | 121.94 (13) |
C1—C2—C3 | 119.13 (14) | C13—C12—C11 | 119.13 (14) |
C1—C2—H2 | 120.4 | C13—C12—H12 | 120.4 |
C3—C2—H2 | 120.4 | C11—C12—H12 | 120.4 |
C4—C3—C2 | 117.40 (13) | N4—C13—C12 | 123.65 (15) |
C4—C3—C6 | 120.98 (13) | N4—C13—H13 | 118.2 |
C2—C3—C6 | 121.60 (13) | C12—C13—H13 | 118.2 |
C5—C4—C3 | 119.20 (14) | N5—C14—C15 | 112.83 (12) |
C5—C4—H4 | 120.4 | N5—C14—C11 | 117.08 (12) |
C3—C4—H4 | 120.4 | C15—C14—C11 | 130.08 (12) |
N1—C5—C4 | 123.96 (15) | C16—C15—C14 | 104.33 (12) |
N1—C5—H5 | 118.0 | C16—C15—H15 | 127.8 |
C4—C5—H5 | 118.0 | C14—C15—H15 | 127.8 |
N2—C6—C8 | 113.02 (12) | N6—C16—O2 | 115.30 (12) |
N2—C6—C3 | 118.22 (13) | N6—C16—C15 | 135.03 (14) |
C8—C6—C3 | 128.72 (13) | O2—C16—C15 | 109.67 (12) |
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 |
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. |
Experimental details
Crystal data | |
Chemical formula | C8H7N3O |
Mr | 161.17 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 187 |
a, b, c (Å) | 14.6411 (13), 10.9272 (10), 10.0060 (9) |
β (°) | 106.987 (1) |
V (Å3) | 1531.0 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.10 |
Crystal size (mm) | 0.42 × 0.18 × 0.10 |
Data collection | |
Diffractometer | Bruker APEX CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.960, 0.990 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8396, 3018, 2509 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.120, 1.02 |
No. of reflections | 3018 |
No. of parameters | 218 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.23, −0.23 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).
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 |
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. |
Acknowledgements
This work was supported by the National Analytical Research Center of Electrochemistry and Spectroscopy, Changchun Institute of Applied Chemistry, Changchun, China.
References
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (1997). SHELXTL. Version 5.1. Bruker AXS Inc., Madison, Wisconsion, USA. Google Scholar
Bruker (1998). SMART. Version 5.0. Bruker AXS Inc., Madison, Wisconsion, USA. Google Scholar
Bruker (2003). SAINT. Version 6. Bruker AXS, Inc., Madison, Wisconsion, USA. Google Scholar
Schmidt, P., Eichenberger, K. & Wilhelm, M. (1966). US Patent 3 277 105. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
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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).