Abstract
C6H5N3O, monoclinic, P21/n (no. 14), a = 5.2140(2) Å, b = 6.8527(2) Å, c = 16.3538(5) Å, β = 97.335(3)°, V = 579.54(3) Å3, Z = 4, Rgt (F) = 0.0336, wRref (F 2) = 0.0881, T = 293(2) K.
Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Data collection and handling.
Crystal: | Colorless bulk |
Size: | 0.21 × 0.18 × 0.15 mm |
Wavelength: | Cu Kα radiation (1.54178 Å) |
μ: | 0.94 mm−1 |
Diffractometer, scan mode: | ROD, Synergy Custom system, HyPix, ω |
θ max, completeness: | 74.0°, 99 % |
N(hkl)measured , N(hkl)unique, R int: | 2843, 1093, 0.014 |
Criterion for I obs, N(hkl)gt: | I obs > 2σ(I obs), 1,041 |
N(param)refined: | 92 |
Programs: | CrysAlisPRO, 1 SHELX 2 , 3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).
Atom | x | y | z | U iso*/U eq |
---|---|---|---|---|
N1 | 0.7106 (2) | 0.29988 (16) | 0.49583 (7) | 0.0195 (3) |
H1A | 0.735487 | 0.414601 | 0.516652 | 0.023* |
H1B | 0.589077 | 0.227413 | 0.510035 | 0.023* |
N2 | 1.0504 (2) | 0.33729 (16) | 0.41684 (6) | 0.0181 (3) |
N3 | 0.67992 (19) | −0.10422 (15) | 0.40688 (6) | 0.0167 (3) |
O1 | 1.16514 (17) | 0.21960 (13) | 0.35720 (5) | 0.0193 (3) |
C1 | 0.8615 (2) | 0.23389 (18) | 0.44113 (7) | 0.0147 (3) |
C2 | 0.8412 (2) | 0.04600 (17) | 0.40029 (7) | 0.0143 (3) |
C3 | 1.0341 (2) | 0.04937 (18) | 0.34964 (7) | 0.0158 (3) |
C4 | 1.0707 (2) | −0.10741 (19) | 0.29833 (7) | 0.0185 (3) |
H4 | 1.195762 | −0.107420 | 0.262569 | 0.022* |
C5 | 0.9066 (2) | −0.26256 (19) | 0.30476 (8) | 0.0193 (3) |
H5 | 0.920706 | −0.373148 | 0.272675 | 0.023* |
C6 | 0.7181 (2) | −0.25659 (18) | 0.35906 (8) | 0.0188 (3) |
H6 | 0.613506 | −0.365703 | 0.361807 | 0.023* |
1 Source of materials
A round-bottom flask with three necks, fitted with a nitrogen inlet and a temperature probe, was initially charged with 12.20 g of 3-fluoropicolinonitrile (1.0 equivalent) and 9.08 g of acetohydroxamic acid (1.2 equivalents) in 65 mL of water at ambient temperature. Following this, a solution containing potassium carbonate (27.64 g, 2.0 equivalents) dissolved in 100 mL of water was introduced to the reaction mixture all at once. The mixture was stirred at 50 °C for a duration of 24 h. Upon completion of the reaction, the resulting crystalline slurry was cooled to 10 °C and allowed to mature for 6 h. The product was subsequently isolated by filtration, rinsed with water (2 × 50 mL), and dried under vacuum at 20 torr while maintaining a nitrogen atmosphere for 24 h. This process yielded 10.67 g of isoxazolo[4,5-b]pyridin-3-amine as a crystalline solid, corresponding to an isolated yield of 79 %.
2 Experimental details
All hydrogen atoms were placed in idealized positions. Their U iso values were set to 1.2 U eq of the parent atoms.
3 Comment
Aminoisoxazoles represent crucial pharmacophores within biologically active and pharmaceutical compounds, also serving as valuable synthetic intermediates. 4 , 5 , 6 Notably, aromatic fused aminoisoxazoles, such as isoxazolo[4,5-b]pyridin-3-amine, hold considerable significance due to their extensive investigation and diverse biological activities. For example, a study by Balog and colleagues delineated a novel class of isoxazolo[4,5-b]pyridin-3-amine derivatives, which exhibit promising potential for the treatment of diseases linked to CYP17.c 7
The crystal structure of isoxazolo[4,5-b]pyridin-3-amine is shown in the figure. The bond lengths of C1–N1, C1=N2 and N2–O1 in the title molecule are 1.343, 1.315 and 1.452 Å, respectively, which are similar with its analogs. 8 , 9 The angle between the five-membered aminoisoxazole-ring consisting of (C1, C2, C3, O1, N2) and six-membered pyridine-ring consisting of (C2, C3, C4, C5, C6, N3) is 0.82°. Besides, the distance between two adjacent molecules in parallel arrangement is 3.3 Å, indicating π–π stacking interaction between the aromatic cycles. The bond lengths and angles are all in the expected ranges.
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Author contribution: Litong Wang and Jinfang Wang are co-first authors, having made equal contributions to this work. All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.
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Conflict of interest: The authors declare no conflicts of interest regarding this article.
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Research funding: The project ZR2024QE449 supported by Shandong Provincial Natural Science Foundation and the Research Program QIT23TP002 of Qilu Institute of Technology.
References
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© 2024 the author(s), published by De Gruyter, Berlin/Boston
This work is licensed under the Creative Commons Attribution 4.0 International License.
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
- Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
- Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
- Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
- Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
- Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
- The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
- The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
- The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
- The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
- Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
- The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
- The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
- Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
- The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
- Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
- The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
- The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
- Crystal structure of (−)-flavesine H, C15H22N2O2
- Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
- Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
- The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
- The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
- Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
- The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
- The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
- The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
- Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
- Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
- Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
- Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
- Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
- Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
- The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
- The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
- Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
- The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
- Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
- Crystal structure of CaPtZn
- Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
- The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
- Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
- The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
- Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
- The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
- Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
- Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
- Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
- Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]−
- Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10
Artikel in diesem Heft
- Frontmatter
- New Crystal Structures
- Crystal structure of the co-crystal 2,4,6-triamino-1,3,5-triazine-1,3-dioxide — acetic acid (1/2) C7H14N6O6
- Crystal structure of the dinuclear mercury(II) complex bis(μ2-bromido)-dibromido-bis{1-[(benzotriazol-1-yl)methyl]-1-H-1,3-(2-ethyl-5-methyl-imidazol)-κ1 N} dimercury(II), C26H30N10Hg2Br4
- Crystal structure of poly[hexaqua-pentakis(μ4-2,2′-bipyridine-4,4′-dicarboxylato-κ4 O:O′:O″:O‴)-(μ2-2,2′-bipyridine-4,4′-dicarboxylato-κ2 O:O)tetraytterbium(III)] hydrate, C36H26N6O16Yb2
- Hydrothermal synthesis and crystal structure of catena-poly[(1,10-phenanthroline-κ 2 N,N′)-bis(μ 2-nitroisophthalato-κ 3 O,O′:O″)nickel(II)], C20H13NiN3O7
- Crystal structure of 72,73,75,76-tetrafluoro-25,44-dimethyl-31,33,36,38-tetraoxo-31,32,33,36,37,38-hexahydro-3(2,7)-benzo[lmn][3,8]phenanthrolina-1,5(4,1)-dipyridin-1-iuma-2,4(1,2),7(1,4)-tribenzenacyclooctaphane-11,51-diium hexafluoridophosphate, [C46H28F4N4O4][PF6]2, a dicationic cyclophane
- Crystal structure of (E)-2-(4-(1H-imidazol-1-yl)benzylidene)-7-fluoro-3,4-dihydronaphthalen-1(2H)-one, C20H15FN2O
- The salt crystal structure of etoricoxib hydrochloride, C18H16Cl2N2O2S
- The structure of t-butyl 7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate, C37H43FN2O5
- The crystal structure of (μ4-oxo)-tri(μ4-2,2′-bipyridine-6,6′-bis(olato)-κ5 O,O′:N:N′:O″)tetrazinc(II) – methylformamide (1/1), C33H25N7O8Zn4
- The co-crystal structure of 4-chlorobenzophenone–salicylhydrazide(1/1), C20H17ClN2O3
- Crystal structure of 9-fluoro-4-(6-methoxypyridin-2-yl)-5,6-dihydrobenzo[h]quinazolin-2-amine, C18H15FN4O
- The crystal structure of the co-crystal composed of benzhydrazide and 5-aminoisophthalic acid, C8H7NO4⋅C7H8N2O
- The cocrystal structure of praziquantel-hesperetin (1/1), C35H38N2O8
- Crystal structure of new barium manganese fluorides dihydrates, Ba10Mn2F25·2H2O
- The crystal structure of bis[μ2-(3-(3-(pyridin-2-yl)-1H-pyrazol-1-yl)propanoate-κ2O:N)-bis(2,2′-bipyridine-κ2 N, N′)dicopper(II)]dinitrate, C42H36Cu2N12O10
- Crystal structure of (3,6-di(2-pyridyl)-4-phenylaminopyridazine-κ2N,N′)-bis(2-(p-toluene)pyridinyl-κ2C,N)-iridium(III) hexafluorophosphate –dichloromethane (1/1), C45H37Cl2F6IrN7P
- The crystal structure of 2-(2′-carboxybenzyl)benzoic acid, C15H12O5
- The crystal structure of dichlorido-[(E)-N′,N″-bis((2E,3E)-3-(hydroxyimino)butan-2-ylidene)-2-((E)-3-(hydroxyimino)butan-2-ylidene)hydrazine-1-carbohydrazonhydrazide-κ 4 N 4]cobalt(II), C13H22N9O3Cl2Co
- Crystal structure of (−)-flavesine H, C15H22N2O2
- Crystal structure of 3-methoxybenzyl 2-(6-methoxynaphthalen-2-yl)propanoate, C22H22O4
- Crystal structure of dicarbonyl(2-oxopyridin-1(2H)-olato-κ 2 O,O)iridium(I), C7H4IrNO4
- The crystal structure of 4-(3-(triphenylphosphonio)propyl)piperazin-1-ium dibromide trihydrate, C25H37Br2N2O3P
- The crystal structure of ethyl 5,6-dihydroxybenzofuran-3-carboxylate, C11H10O5
- Crystal structure of 14-(R)-(2′-cyano-phenoxy)-3,19-diacetyl andrographolide, C31H37NO7
- The twinned crystal structure of 10-(4-methyl benzoate)-2,8-diethyl-5,5-difluoro-1,3,7,9-tetramethyl-5H-di-pyrrolo[1,2-c:2′,1′-f] [1,3,2]diazaborinin-4-ium-5-uide, C25H29BF2N2O2
- The crystal structure of (9H-thioxanthen-9- ylidene)hydrazine monohydrate, C13H11N2SO0.5
- The crystal structure of pyridinium diaqua-{1,2-phenylenebis((carboxylatocarbonyl)amido-κ4 N,N′,O,O′)manganese(III), C15H14MnN3O8
- Crystal structure of the hydrogen storage active high entropy phase Tb0.82Sm0.18Ni0.83Co0.17Mg
- Crystal structure of diaqua-bis[5-methyl-1-(1H-pyrazol-3-yl)-1H-1,2,3-triazole-4-carboxylato-κ 2 N,O)]manganese(II), C14H16MnN10O6
- Crystal structures of diiodido-3-((pyridin-2-ylmethylene)amino)-2-(pyridin-3-yl)-2,3-dihydroquinazolin-4(1H)-one-cadmium(II)
- Synthesis and crystal structure of methyl 4-(2-ethoxy-2-oxoethoxy)-3,5-dimethoxybenzoate, C14H18O7
- Crystal structure of isoxazolo[4,5-b]pyridin-3-amine, C6H5N3O
- Crystal structure of 4-chloro-1-isobutyl-1H-imidazo, C14H14ClN3
- The crystal structure of 1,1,1,2,2,2-hexakis(2-methyl-2-phenylpropyl)distannane,C60H78Sn2
- The crystal structure of (2,7-dimethoxynaphthalene-1,8-diyl)bis((3-nitrophenyl)methanone), C26H18N2O8
- Crystal structure of diaqua-tetra((E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)pent-1-en-3-ol-κ 1 N)zinc(II) dinitrate dihydrate, C60H76Cl8N14O14Zn
- The crystal structure of diphenyl bis(2-((diphenoxyphosphoryl)amino)ethyl)phosphoramidate monohydrate C40H42N3O10P3
- Crystal structure of 4,4′-bis(dibromomethyl)-1,1′-biphenyl, C14H10Br4
- Crystal structure of CaPtZn
- Crystal structure of 3-chloro-5-(trifluoromethyl)pyridine-2-carboxylic acid, C7H3ClF3NO2
- The crystal structure of (3′-(2-bromophenyl)-2-phenyl-[2,2′-bioxiran]-3-yl)(phenyl)methanone, C92H68O12Br4
- Crystal structure of ethyl 4-(4-benzylpiperazin-1-yl)benzoate, C20H24N2O2
- The crystal structure of bis(selenocyanato-κ1 N)-bis(methanol)-bis((1E,2E)-1,2-bis (1-(pyridin-4-yl)ethylidene)-hydrazine)iron(II) methanol solvate, C34H44FeN10O4Se2
- Crystal structure of (E)-1-(5-bromo-2-hydroxyphenyl)-3-(5-(4-methoxyphenoxy)-3-methyl-1-phenyl-1H-pyrazol-4-yl)prop-2-en-1-one, C26H21BrN2O4
- The crystal structure of methyl 4-(4-(methylsulfonyl)phenyl)-2-methyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline-3-carboxylate, C19H21NO5S
- Crystal structure of 1′,3′-dihydro-2,2′-spirobi[indene]-1,3-dione, C17H12O2
- Crystal structure of (E)-2,2′,3,3′-tetrahydro-[1,1′-biindenylidene]-4,4′-diol, C18H16O2
- Crystal structure of di-glycylglycinium squarate dihydrate, C12H22N4O12, at 105 K
- Crystal structure of {[(4-fluorophenyl)methyl]triphenylphosphonium}dibromocopper(I), [C25H21FP]+[CuBr2]−
- Crystal structure of poly[diaqua-bis(μ2-5-((pyridin-4-yl-methyl)amino)benzene-1,3-dicarboxylato-κ 2 N:O)cadmium(II)], C28H26CdN4O10