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1.  N′-(2-Hy­droxy­benzyl­idene)-2-(hy­droxy­imino)­propano­hydrazide 
The mol­ecule of the title compound, C10H11N3O3, adopts an all-trans conformation and is approxomately planar, the largest deviation from the least-squares plane through all non-H atoms being 0.261 (1) Å. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, the mol­ecules are packed into layers lying parallel to the ab plane by π-stacking inter­actions between the benzene ring of one molecule and the C—N bond of the oxime group of another molecule; the shortest inter­molecular C⋯C separation within the layer is 3.412 (1) Å. The layers are connected by O—H⋯O and N—H⋯O hydrogen bonds.
doi:10.1107/S1600536811045818
PMCID: PMC3238939  PMID: 22199788
2.  Dichlorido{2-hydroxy­imino-N′-[1-(2-pyrid­yl)ethyl­idene]propanohydrazide-κ3 N,N′,O}zinc(II) hemihydrate 
The title compound, [ZnCl2(C10H12N4O2)]·0.5H2O, was readily prepared by the reaction between ZnCl2 and 2-hydroxy­imino-N′-[1-(2-pyrid­yl)ethyl­idene]propanohydrazide. The Zn atom has a distorted trigonal–bipyramidal geometry with two Cl atoms and one azomethine N atom in the equatorial plane and one pyridine N atom and one amide O atom in the axial positions. In the crystal structure, complex mol­ecules are connected in pairs by N—H⋯Cl hydrogen bonds, formed between the amide NH of one mol­ecule and the Cl atom of a neighboring one. Mol­ecular pairs are connected by hydrogen bonds involving the uncoordinated water mol­ecule, which lies on a twofold axis.
doi:10.1107/S160053680706535X
PMCID: PMC2960173  PMID: 21201313
3.  1-[1-(Hydroxy­imino)eth­yl]-N-(2-methoxy­phen­yl)cyclo­propane­carboxamide 
The title compound, C13H16N2O3, adopts an E configuration with respect to the C=N bond and an intra­molecular N—H⋯N hydrogen bond results in the formation of a six-membered ring. In the crystal, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into a chain propagating along the b axis. Very weak π–π stacking inter­actions [centroid–centroid distance = 4.18 (2) Å] may further consolidate the packing, forming a two-dimensional supra­molecular network.
doi:10.1107/S1600536809022260
PMCID: PMC2969475  PMID: 21582888
4.  4-[1-(Hydroxy­imino)ethyl]-N-(4-nitro­benzyl­idene)aniline 
In the title compound, C15H13N3O3, the dihedral angle formed by the two benzene rings is 44.23 (2)°. The crystal structure is stabilized by aromatic π–π stacking inter­actions, with centroid-centroid distances of 3.825 (3) and 3.870 (4) Å between the aniline and the nitro­benzene rings of neighbouring mol­ecules, respectively. In addition, the stacked mol­ecules exhibit inter­molecular C—H⋯N and C—H⋯O inter­actions.
doi:10.1107/S1600536809033753
PMCID: PMC2970305  PMID: 21577917
5.  Ethyl (2E)-2-(hydroxy­imino)propanoate 
The mol­ecule of the title compound, C5H9NO3, is essentially planar [the maximum deviation for a non-H atom from the mean plane is 0.021 (3) Å] due to the π-conjugation of the hydroxy­imino and carbonyl groups, which are trans to each other; ab initio calculations in vacuo at the DFT (B3LYP/6–311G**++) level of theory confirmed that E conformer is indeed the lowest in energy. The packing in crystal structure is influenced by strong inter­molecular O—H⋯N hydrogen-bonding inter­actions between oxime groups and also by π-stacking of the mol­ecules due to the carbonyl and oxime group orbital overlap [inter­planar distance between adjacent mol­ecules = 3.143 (4) Å]. Jointly, these factors afford infinite 6.32 Å thick mol­ecular sheets, where the plane of each mol­ecule is perpendicular to the plane of the sheet. Seen from above, the mol­ecules within the sheet are arranged in a herringbone pattern. Such sheets form a stack due to weak van der Waals inter­actions; the gap between adjacent sheets is 2.07 Å.
doi:10.1107/S1600536810009438
PMCID: PMC2983986  PMID: 21580705
6.  4-Chloro-2-((E)-{3-[1-(hydroxy­imino)eth­yl]phen­yl}imino­meth­yl)phenol 
The title compound, C15H13ClN2O2, adopts an E conformation with respect to the azomethine C=N bond. The aniline and phenol rings are almost coplanar, making a dihedral angle of 3.33 (2)°. In the crystal, the mol­ecules lie about inversion centers, forming dimers that are connected by inter­molecular O—H⋯N hydrogen bonds, resulting in six-membered rings with graph-set motif R 2 2(6). In addition, there is a strong inter­molecular O—H⋯N hydrogen-bonding inter­action, resulting in an S(6) ring motif. Weak π–π inter­actions between the benzene rings [centroid–centroid distance = 3.809 (1) Å] further stabilize the crystal structure.
doi:10.1107/S1600536809045942
PMCID: PMC2972112  PMID: 21578758
7.  (E)-Methyl 2-({2-eth­oxy-6-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-phenyl­acrylate 
In the title compound, C20H21NO5, the dihedral angle between the mean planes through the two rings is 47.1 (8)°. The enoate group assumes an extended conformation. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane being 0.061 (1) Å for the O atom. In the crystal, mol­ecules are linked into cyclic centrosymmetric dimers with an R 2 2(6) motif via pairs of O—H⋯N hydrogen bonds. Inter­molecular C—H⋯O hydrogen bonds form a C(8) chain along the b axis. The crystal packing is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536812014596
PMCID: PMC3344504  PMID: 22590266
8.  N-(4-Chloro­phen­yl)-2-(hydroxy­imino)acetamide 
The title compound, C8H7ClN2O2, is an inter­mediate in the synthesis of 5-chloro­isatin, which can be further transformed to 5-chloro-2-indolinone via a Wolff–Kishne reduction. The C2N acetamide plane forms a dihedral angle of 6.3 (3)° with the benzene ring. An intra­molecular C—H⋯O inter­action results in the formation of a six-membered ring. In the crystal, inter­molecular N—H⋯O, N—H⋯N and O—H⋯O hydrogen bonds link the mol­ecules into multimers, forming sheets.
doi:10.1107/S1600536809033315
PMCID: PMC2969878  PMID: 21577646
9.  2-Hydroxy­imino-N′-[1-(2-pyrid­yl)ethyl­idene]propanohydrazide 
The title compound, C10H12N4O2, features an intra­molecular N—H⋯N hydrogen bond formed between the imine NH and oxime N atoms. The oxime group and the amide C=O bond are anti to each other. In the crystal, mol­ecules are connected by O—H⋯O hydrogen bonds into supra­molecular zigzag chains along the c axis.
doi:10.1107/S1600536809033352
PMCID: PMC2969988  PMID: 21577640
10.  (E)-N′-(2-Hydroxy­benzyl­idene)-2-(4-isobutyl­phen­yl)propanohydrazide 
The title hydrazide compound, C20H24N2O2, exists in a trans configuration with respect to the acyclic C=N bond and an intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. The mean plane through the formohydrazide unit is essentially planar [maximum deviation = 0.025 (2) Å], and forms dihedral angles of 24.45 (16) and 87.14 (16)° with the two benzene rings. In the crystal structure, inter­molecular N—H⋯O and C—H⋯O hydrogen bonds link neighbouring mol­ecules into extended chains along the c axis, which incorporate R 2 2(16) ring motifs. An inter­molecular C—H⋯π inter­action is also observed.
doi:10.1107/S1600536809050971
PMCID: PMC2980184  PMID: 21580121
11.  (E)-Methyl 3-(4-ethyl­phen­yl)-2-{2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy­meth­yl}acrylate 
In the title compound, C20H21NO4, the two benzene rings are almost perpendicular to each other, making a dihedral angle of 86.1 (7)°. The hy­droxy­ethanimine group is essentially coplanar with the benzene ring, the largest deviation from the mean plane of the hy­droxy­ethanimine [C=N—OH] group being 0.011 (1) Å for the O atom. An intra­molecular C—H⋯O hydrogen bond occurs. The mol­ecules are linked into cyclic centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds. Inter­molecular C—H⋯O hydrogen bonds link the mol­ecules, forming a C(8) chain along the a axis. The crystal packing is further stabilized by C—H⋯π inter­actions.
doi:10.1107/S1600536811038359
PMCID: PMC3201344  PMID: 22058811
12.  (E)-Methyl 3-(4-chloro­phen­yl)-2-{2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy­meth­yl}acrylate 
In the title compound, C18H16ClNO4, the dihedral angle between the mean planes through the aromatic rings is 83.8 (8)°. The hy­droxy­ethanimine group is essentially coplanar with the ring to which it is attached [O—N—C—C torsion angle = −177.96 (13)°]. The mol­ecules are linked into centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds. The crystal packing is further stabilized by C—H⋯O inter­actions.
doi:10.1107/S1600536811038372
PMCID: PMC3201559  PMID: 22064839
13.  Methyl (E)-2-({2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-(4-methyl­phen­yl)acrylate 
In the title compound, C19H19NO4, the dihedral angle between the mean planes through the benzene rings is 82.18 (7)°. The C=N double bond is trans-configured. The mol­ecules are linked into centrosymmetric dimers via pairs of O—H⋯N hydrogen bonds with the motif R 2 2(6). The crystal packing also features C—H⋯O inter­actions. The methyl group attached to one of the aromatic rings is disordered over two almost equally occupied positions [occpancy ratio = 0.51 (4):0.49 (4)].
doi:10.1107/S1600536812019046
PMCID: PMC3379223  PMID: 22719421
14.  4-Bromo-2-({4-[(hy­droxy­imino)­meth­yl]phen­yl}imino­meth­yl)phenol 
In the title compound, C14H11BrN2O2, the mean planes of the two benzene rings are almost parallel to each other, making a dihedral angle of 4.09 (1)°. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, inter­molecular O—H⋯N and C—H⋯O hydrogen bonds link the mol­ecules into a chain-like supra­molecular structure.
doi:10.1107/S160053681002698X
PMCID: PMC3007216  PMID: 21588325
15.  Tris(3-hy­droxy­imino-1-methyl­indolin-2-one) monohydrate 
There are three independent 3-hy­droxy­imino-1-methyl­indolin-2-one mol­ecules and a water mol­ecule in the asymmetric unit of the title compound, 3C9H8N2O2·H2O. The crystal packing is stablized by O—H⋯O and O—H⋯Nhydrogen bonds between 3-hy­droxy­imino-1-methyl­indolin-2-one mol­ecules and the water mol­ecule and weak π–π stacking inter­actions [centroid–centroid distances in the range 3.446 (2)–3.983 (2) Å], forming a two-dimensional network.
doi:10.1107/S1600536811015418
PMCID: PMC3120467  PMID: 21754698
16.  [μ-N,N′-Bis(2-pyridylmethyl­ene)ethane-1,2-diamine]bis­{aqua­[N,N′-bis­(2-pyridyl­methyl­ene)ethane-1,2-diamine]manganese(II)} tetra­kis(perchlorate) 
The cation of the salt, [Mn2(C14H14N4)3(H2O)2](ClO4)4, lies on a center of inversion, the center lying midway along the ethyl­ene chain of the bridging N,N′-bis­(2-pyridylmethyl­ene)ethane-1,2-diamine ligand. The Mn atom is chelated by two atoms N atoms of this bridging ligand, and is also coordinated by four N atoms of another ligand. The Mn atom is seven-coordinated in a penta­gonal-bipyramidal environment. The crystal structure displays inter­molecular π–π inter­actions between adjacent pyridine rings, with a shortest centroid–centroid distance of 3.784 (3) Å. The perchlorate is linked to the dinuclear cation by O—H⋯O hydrogen bonds.
doi:10.1107/S1600536810003764
PMCID: PMC2983616  PMID: 21580209
17.  2-[(2-Chloro­phen­yl)imino­meth­yl]-4,6-di­iodo­phenol 
The asymmetric unit of the title compound, C13H8ClI2NO, contains half of the mol­ecule situated on a mirror plane. The hy­droxy group is involved in the formation of an intra­molecular O—H⋯N hydrogen bond. π–π inter­actions between the benzene rings of neighbouring mol­ecules [centroid–centroid distance = 3.629 (3) Å] form stacks along the b axis. In the crystal, weak C—H⋯O and C—H⋯Cl inter­actions are observed.
doi:10.1107/S1600536812007325
PMCID: PMC3297899  PMID: 22412702
18.  Methyl (E)-2-({2-[(E)-(hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-phenyl­acrylate 
In the title compound, C18H17NO4, the hy­droxy­ethanimine group is essentially coplanar with the ring to which it is attached [C—C—N—O torsion angle = 179.94 (14)°]. The mol­ecules are linked into cyclic centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds and the crystal packing is further stabilized by C—H⋯O inter­actions.
doi:10.1107/S1600536812002711
PMCID: PMC3295410  PMID: 22412521
19.  (E)-2-{4-[1-(Hydroxyimino)ethyl]phenyl­iminomethyl}-6-methoxyphenol mono­hydrate 
In the title compound, C16H16N2O3·H2O, the benzene rings are nearly coplanar with each other, forming a dihedral angle of 4.46 (3)°. There is a strong intra­molecular O—H⋯N hydrogen bond which results in a six-membered ring. In the crystal, the mol­ecules are connected into a three-dimensional network via O—H⋯O and O—H⋯N inter­molecular hydrogen bonds, forming a centrosymmetric ring along the b axis with graph-set motif R 4 4(10). In addition, the short distances between the centroids of six-membered rings [3.555 (1) Å], indicate the existence of π–π stacking inter­actions, which may stabilize the crystal structure.
doi:10.1107/S1600536809042032
PMCID: PMC2971266  PMID: 21578358
20.  2-(3,5-Dimethyl-1H-pyrazol-1-yl)-2-hy­droxy­imino-N′-[1-(pyridin-2-yl)ethyl­idene]acetohydrazide 
In the title compound, C14H16N6O2, the dihedral angles formed by the mean plane of the acetohydrazide group [maximum deviation 0.0629 (12) Å] with the pyrazole and pyridine rings are 81.62 (6) and 38.38 (4)° respectively. In the crystal, mol­ecules are connected by N—H⋯O and O—H⋯N hydrogen bonds into supra­molecular chains extending parallel to the c-axis direction.
doi:10.1107/S1600536812045412
PMCID: PMC3588977  PMID: 23476213
21.  A triclinic polymorph of (E)-2-(4-iso­butyl­phen­yl)-N′-[1-(4-nitro­phen­yl)ethyl­idene]propano­hydrazide 
The asymmetric unit of the triclinic polymorph of the title compound, C21H25N3O3, consists of two mol­ecules, whereas for the monoclinic polymorph Z′ = 1 [Fun et al. (2009 ▶). Acta Cryst. E65, o445]. The two mol­ecules exhibit an E configuration with respect to the C=N bond. The mol­ecules are linked into dimers by N—H⋯O and C—H⋯O hydrogen bonds forming R 2 2(8) ring motifs. In addition, π–π inter­actions occur between nitro­phenyl groups [minimum centroid–centroid distance 3.940 (2) Å], stacking the molecules along the ac plane.
doi:10.1107/S1600536813019892
PMCID: PMC3793817  PMID: 24109404
22.  2-(4-Isobutyl­phen­yl)-N′-[1-(4-nitro­phen­yl)ethyl­idene]propanohydrazide 
The mol­ecule of the title compound, C21H25N3O3, exists in a trans configuration with respect to the ethyl­idene unit. The dihedral angle between the two substituted benzene rings is 86.99 (7)°. The nitro group is twisted from the attached benzene ring at an angle of 17.02 (7)°. In the crystal structure, mol­ecules are linked by pairs of N—H⋯O hydrogen bonds in a face-to-face manner into centrosymmetric dimers. These dimer units are further linked into chains along the c axis by weak C—H⋯O inter­actions. These chains are stacked along the b axis. The crystal is further stabilized by weak C—H⋯π inter­actions.
doi:10.1107/S1600536809003420
PMCID: PMC2968536  PMID: 21582118
23.  (E)-1-[(2-Chloro-4-nitro­phenyl­imino)­meth­yl]naphthalen-2-ol 
In the title compound, C17H11ClN2O3, an intra­molecular O—H⋯N hydrogen bond influences the mol­ecular conformation; the naphthol system and the substituted benzene ring form a dihedral angle of 3.5 (1)°. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link mol­ecules into chains in the [010] direction The crystal packing exhibits π–π inter­actions between the aromatic rings from the neighbouring mol­ecules, with a centroid–centroid distance of 3.566 (7) Å.
doi:10.1107/S1600536811021374
PMCID: PMC3151923  PMID: 21837024
24.  (E,E)-1-(2-Hydroxy­imino-1-phenyl­ethyl­idene)semicarbazide monohydrate 
In the title compound, C9H10N4O2·H2O, the oxime unit has an E configuration, and an intra­molecular N—H⋯N hydrogen bond results in the formation of a planar five-membered ring, which is oriented with respect to the aromatic ring at a dihedral angle of 74.82 (17)°. In the crystal structure, inter­molecular O—H⋯O and N—H⋯O hydrogen bonds link the mol­ecules and R 2 2(8) ring motifs are apparent.
doi:10.1107/S1600536809013865
PMCID: PMC2977740  PMID: 21583876
25.  (Z)-Ethyl 2-hydroxy­imino-2-(4-nitro­benz­yl)ethanoate 
The title mol­ecule, C11H10N2O6, has a Z conformation about the C=N bond of the oxime unit. There are significant twists from planarity throughout the mol­ecule, the most significant being between the hydroxy­imino and ester groups which are effectively orthogonal with an N—C—C—Ocarbon­yl torsion angle of 91.4 (2)°. The crystal packing features oxime–benzoyl O—H⋯O contacts that lead to chains along [010] and C—H⋯O interactions also occur.
doi:10.1107/S1600536809052386
PMCID: PMC2980268  PMID: 21580028

Results 1-25 (297547)