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1.  (E)-2-({2-[(E)-(Hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-p-tolyl­acrylonitrile 
In the title compound, C18H16N2O2, the hy­droxy­ethanimine group is essentially coplanar with the ring to which it is attached (C—C—N—O torsion angle = −176.9°). Mol­ecules are linked into cyclic centrosymmetric R 2 2(6) dimers via O—H⋯N hydrogen bonds.
doi:10.1107/S160053681200270X
PMCID: PMC3297297  PMID: 22412487
2.  (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
3.  (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
4.  (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
5.  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
6.  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
7.  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
8.  (E)-2-({2-[(E)-(Hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-phenyl­acrylonitrile 
In the title compound, C17H14N2O2, the hy­droxy­ethanimine group adopts an anti­periplanar conformation. In the crystal, mol­ecules are linked by O—H⋯N hydrogen bonds, forming zigzag chains running along the c axis.
doi:10.1107/S1600536812003923
PMCID: PMC3297320  PMID: 22412510
9.  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
10.  4-[(E)-(Hy­droxy­imino)­meth­yl]-N,N-di­methyl­anilinium chloride 
In the title compound, C9H13N2O+·Cl−, the cation, apart from the methyl groups, is almost planar, with a maximum deviation of 0.040 (1) Å; the methyl C atoms deviate by 0.389 (2) and −1.247 (1) Å, from the mean plane. In the crystal, cations and anions associate through C—H⋯Cl hydrogen bonds, forming a helical arrangement. In addition, inter­molecular O—H⋯Cl, N—H⋯Cl and C—H⋯N inter­actions are observed.
doi:10.1107/S1600536812020211
PMCID: PMC3379298  PMID: 22719496
11.  Bis­{(E)-3-[2-(hy­droxy­imino)­propan­amido]-2,2-dimethyl­propan-1-aminium} bis[μ-(E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamido­(2−)]bis­{[(E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamide]­copper(II)} bis­((E)-{3-[2-(hy­droxy­imino)­propanamido]-2,2-dimethyl­prop­yl}carbamate) acetonitrile disolvate 
The reaction between copper(II) nitrate and (E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamide led to the formation of the dinuclear centrosymmetric copper(II) title complex, (C8H18N3O2)2[Cu2(C8H15N3O2)2(C8H17N3O2)2](C9H16N3O4)2·2CH3CN, in which an inversion center is located at the midpoint of the Cu2 unit in the center of the neutral [Cu2(C8H15N3O2)2(C8H17N3O2)2] complex fragment. The Cu2+ ions are connected by two N—O bridging groups [Cu⋯Cu separation = 4.0608 (5) Å] while the CuII ions are five-coordinated in a square-pyramidal N4O coordination environment. The complex mol­ecule co-crystallizes with two mol­ecules of acetonitrile, two mol­ecules of the protonated ligand (E)-3-[2-(hy­droxy­imino)­propanamido]-2,2-dimethyl­propan-1-aminium and two negatively charged (E)-{3-[2-(hy­droxy­imino)­propanamido]-2,2-dimethyl­prop­yl}carbamate anions, which were probably formed as a result of condensation between (E)-N-(3-amino-2,2-dimethyl­prop­yl)-2-(hy­droxy­imino)­propanamide and hydro­gencarbonate anions. In the crystal, the complex fragment [Cu2(C8H15N3O2)2(C8H17N3O2)2] and the ion pair C8H18N3O2 +.C9H16N3O4 − are connected via an extended system of hydrogen bonds.
doi:10.1107/S160053681204620X
PMCID: PMC3588739  PMID: 23468704
12.  4-[(E)-(2,4-Difluoro­phen­yl)(hydroxy­imino)meth­yl]piperidinium picrate 
The title compound, C12H15F2N2O+·C6H2N3O7 −, a picrate salt of 4-[(E)-(2,4-difluoro­phen­yl)(hydroxy­imino)meth­yl]piper­idine, crystallizes with two independent mol­ecules in a cation–anion pair in the asymmetric unit. In the cation, a methyl group is tris­ubstituted by hydroxy­imino, piperidin-4-yl and 2,4-difluoro­phenyl groups, the latter of which contains an F atom disordered over two positions in the ring [occupancy ratio 0.631 (4):0.369 (4)]. The mean plane of the hydr­oxy group is in a synclinical conformation nearly orthogonal [N—C—C—C = 72.44 (19)°] to the mean plane of the piperidine ring, which adopts a slightly distorted chair conformation. The dihedral angle between the mean plane of the 2,4-difluoro­phenyl and piperidin-4-yl groups is 60.2 (3)°. In the picrate anion, the mean planes of the two o-NO2 and single p-NO2 groups adopt twist angles of 5.7 (2), 25.3 (7) and 8.3 (6)°, respectively, with the attached planar benzene ring. The dihedral angle between the mean planes of the benzene ring in the picrate anion and those in the hydroxy­imino, piperidin-4-yl and 2,4-difluoro­phenyl groups in the cation are 84.9 (7), 78.9 (4) and 65.1 (1)°, respectively. Extensive hydrogen-bond inter­actions occur between the cation–anion pair, which help to establish the crystal packing in the unit cell. This includes dual three-center hydrogen bonds with the piperidin-4-yl group, the phenolate and o-NO2 O atoms of the picrate anion at different positions in the unit cell, which form separate N—H⋯(O,O) bifurcated inter­molecular hydrogen-bond inter­actions. Also, the hydr­oxy group forms a separate hydrogen bond with a nearby piperidin-4-yl N atom, thus providing two groups of hydrogen bonds, which form an infinite two-dimensional network along (011).
doi:10.1107/S1600536809035363
PMCID: PMC2970333  PMID: 21577832
13.  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
14.  3-Meth­oxy-2-[(E)-(4-meth­oxy­phen­yl)imino­meth­yl]phenol 
The title compound, C15H15NO3, adopts the enol–imine tautomeric form. The two rings are twisted with respect to each other, making a dihedral angle of 44.08 (5)°. The 3-methoxy-2-[(E)-(4-methoxyphenyl)-iminomethyl]phenol unit is almost planar, the largest deviation from the mean plane being 0.047 (2) Å. Such a planar conformation might be related to the occurrence of an intra­molecular O—H⋯N hydrogen bond. In the crystal, inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into sheets parallel to (010). These sheets are inter­connected by weak C—H⋯π inter­actions.
doi:10.1107/S1600536811000596
PMCID: PMC3051687  PMID: 21523025
15.  2-{(1E)-1-[(3-{(E)-[1-(2-Hy­droxy-4-meth­oxy­phen­yl)ethyl­idene]amino}-2,2-di­methyl­prop­yl)imino]­eth­yl}-5-meth­oxy­phenol 
Mol­ecules of the title compound, C23H30N2O4, are located on a crystallographic mirror plane. The mol­ecule has a curved shape with the dihedral angle formed between the two benzene rings being 55.26 (5)°. Intra­molecular O—H⋯N hydrogen bonds are noted. In the crystal, supra­molecular layers are formed in the ac plane owing to the presence of C—H⋯π inter­actions.
doi:10.1107/S1600536811038815
PMCID: PMC3201500  PMID: 22058812
16.  Di-μ-oxido-bis­[(2-eth­oxy-6-{[2-(2-hy­droxy­ethyl­amino)­ethyl­imino]­meth­yl}phenolato-κ3 N,N′,O 1)oxidovanadium(V)] 
In the title centrosymmetric dinuclear dioxidovanadium(V) complex, [V2(C13H19N2O3)2O4], the VV ion is coordinated by an N,N′,O-tridendate 2-eth­oxy-6-{[2-(2-hy­droxy­ethyl­amino)­ethyl­imino]­meth­yl}phenolate ligand and three oxide O atoms, forming a distorted cis-VN2O4 octa­hedral geometry. The bridging O atoms show one short and one long bond to their two attached VV atoms. The dihedral angle between the benzene ring of the ligand and the V2O2 plane is 75.2 (3)°. The deviation of the VV ion from the plane defined by the three donor atoms of the tridentate ligand and one bridging oxide O atom is 0.337 (2) Å towards the terminal oxide O atom. Two N—H⋯O hydrogen bonds help to establish the conformation of the dimer. In the crystal, the complex mol­ecules are linked by O—H⋯O hydrogen bonds, forming [100] chains.
doi:10.1107/S160053681105094X
PMCID: PMC3254302  PMID: 22259331
17.  2,2′-[(3-Bromo-4-hy­droxy-5-meth­oxy­phen­yl)methyl­idene]bis­(3-hy­droxy-5,5-dimethyl­cyclo­hex-2-en-1-one) 
In the title compound, C24H29BrO6, the dihedral angle between the cyclo­hexenone mean planes is 57.63 (2)° while the dihedral angles between the benzene ring and the cyclo­hexenone mean planes are 58.42 (2) and 69.08 (3)°. The two cyclo­hexenone rings both show an envelope conformation, with the C atom bearing two methyl groups as the flap atom in each ring. Two intra­molecular O—H⋯O hydrogen bonds occur. In the crystal, molecules are linked via pairs of O—H⋯O hydrogen bonds, forming inversion dimers.
doi:10.1107/S1600536812037853
PMCID: PMC3470230  PMID: 23125674
18.  2-{[(4-{[(2-Hy­droxy­phen­yl)(phen­yl)methyl­idene]amino}­phen­yl)imino](phen­yl)meth­yl}phenol 
The title mol­ecule, C32H24N2O2, has a crystallographically imposed inversion centre and exists in the crystal as an enol–imine tautomer. The mol­ecular structure is stabilized by two strong intra­molecular O—H⋯N hydrogen bonds. The dihedral angles between the central benzene ring and the mean planes of the phenyl substituents are 59.99 (1) and 62.79 (2)°. In the crystal, the mol­ecules are arranged into (010) layers via C—H⋯π inter­actions.
doi:10.1107/S1600536811046988
PMCID: PMC3238908  PMID: 22199761
19.  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
20.  Methyl 2-[(carbamoyl­amino)­imino]-2-(3-{1-[(carbamoyl­amino)­imino]-2-meth­oxy-2-oxoeth­yl}phen­yl)acetate ethanol monosolvate monohydrate 
In the title compound, C14H16N6O6·C2H6O·H2O, both substit­uents of the benzene ring are approximately planar with maximum deviations from the mean plane of 0.0561 (12) (an imine N atom) and 0.1419 (11) Å (a meth­oxy O atom). The substituents are tilted out of the plane of the benzene ring by 64.48 (4) and 70.08 (5)°, respectively. In the crystal, mol­ecules form centrosymmetric dimers associated via pairs of N—H⋯O hydrogen bonds. The dimers are linked via the water and ethanol mol­ecules, forming two-dimensional hydrogen-bond networks lying parallel to (100).
doi:10.1107/S1600536812001237
PMCID: PMC3275217  PMID: 22347073
21.  3-(2-Chloro-3-hy­droxy-4-meth­oxy­phen­yl)-1-(4,5-dimeth­oxy-2-methyl­phen­yl)prop-2-en-1-one 
The title compound, C19H19ClO5, is a chloro derivative of a biologically significant chalcone family. The mean plane of the two substituted benzene rings are twisted by 55.33 (8)° with respect to each other. An intra­molecular C—H⋯Cl hydrogen bond generates an S(5) graph-set motif. In the crystal, a bifurcated O—H⋯(O,O) hydrogen bond leads to an R 1 2(5) graph-set motif and to the formation of zigzag chains propagating along the c-axis direction. A weak π–π inter­action involving the methyl­phenyl rings [centroid–centroid distance = 3.8185 (10) Å] and C—H⋯π inter­actions also occur.
doi:10.1107/S1600536812038275
PMCID: PMC3470302  PMID: 23125715
22.  3-[Hy­droxy(3-meth­oxy­phen­yl)methyl­idene]-2-(2-oxo-2-phenyl­eth­yl)-3,4-dihydro-2H-1λ6,2-benzothia­zine-1,1,4-trione 
In the title mol­ecule, C24H19NO6S, the heterocyclic thia­zine ring adopts a half-chair conformation with the S and N atoms displaced by 0.180 (5) and 0.497 (5) Å, respectively, on opposite sides of the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia­zine unit and the meth­oxy­phenyl group are almost coplanar, with the dihedral angle between the mean planes of these rings being 5.9 (2)°, while the benzene ring of the 2-oxo-2-phenyl­ethyl group is inclined at 79.68 (11) and 81.01 (10)°, respectively, to these rings. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯N inter­actions, and the crystal packing is stabilized by weak C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812009002
PMCID: PMC3343951  PMID: 22590032
23.  Methyl (2Z)-2-({N-[2-(hy­droxy­meth­yl)phen­yl]-4-methyl­benzene­sulfonamido}­meth­yl)-3-phenyl­prop-2-enoate 
In the title compound, C25H25NO5S, the O atom of the hy­droxy group is disordered over two positions, with occupancies of 0.820 (2) and 0.180 (2). The sulfonyl-bound benzene ring forms dihedral angles of 31.8 (1) and 60.7 (1)°, respectively, with the hy­droxy­methyl­benzene and phenyl rings. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯O hydrogen bond, generating an S(8) ring motif. The crystal packing is stabilized by inter­molecular C—H⋯O hydrogen bonds and C—H⋯π inter­actions.
doi:10.1107/S1600536812000864
PMCID: PMC3275177  PMID: 22347033
24.  2-[2-(3-Chloro­phen­yl)-2-oxoeth­yl]-4-hy­droxy-3-(3-meth­oxy­benzo­yl)-2H-1λ6,2-benzothia­zine-1,1-dione 
In the title mol­ecule, C24H18ClNO6S, the heterocyclic thia­zine ring adopts a half chair conformation with the S and N atoms displaced by 0.318 (3) and 0.387 (3) Å, respectively, on the opposite sides from the mean plane formed by the remaining ring atoms. The benzene rings of the benzothia­zin unit and meth­oxy­benzoyl group are more or less coplanar, the dihedral angle between the mean planes of these rings being 12.37 (10)° while the chloro­phenyl ring is inclined at 81.87 (4) and 73.30 (5)°, respectively, to these rings. The mol­ecular structure is consolidated by intra­molecular O—H⋯O and C—H⋯N inter­actions and the crystal packing is stabilized by weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536812009014
PMCID: PMC3343952  PMID: 22590033
25.  2-Eth­oxy-6-({2-[(3-eth­oxy-2-hy­droxy­benzyl­idene)amino]­benz­yl}imino­meth­yl)phenol 
The title compound, C25H26N2O4, exists in an E conformation with respect to each azomethine link. The two phenol-substituted benzene rings are twisted away from the plane of the diimine benzene ring by dihedral angles of 27.25 (5) and 56.67 (5)°. The mol­ecular structure is stabilized by intra­molecular O—H⋯N hydrogen bonds.
doi:10.1107/S1600536812031479
PMCID: PMC3414937  PMID: 22904924

Results 1-25 (124819)