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1.  (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
2.  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
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.  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
5.  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
6.  Bis{2,6-bis­[(2-hy­droxy-5-methyl­phen­yl)imino­meth­yl]pyridine} monohydrate 
The title compound, 2C21H19N3O2·H2O, was synthesized by a Schiff base condensation of 2,6-diformyl­pyridine with 2-amino-4-methyl­phenol in ethanol. In the crystal, two mol­ecules of 2,6-bis­[(2-hy­droxy-5-methyl­phen­yl)imino­meth­yl]pyridine dimer­ize via hydrogen bonding to a water mol­ecule, which lies on a twofold axis. There are also intra­molecular phenol–imine hydrogen bonds. The dimers are further linked via π–π (phen­yl–pyridine) [centroid–centroid distance = 3.707 (2) Å] and π–π edge-to-edge [3.392 (2) Å] inter­actions. The dihedral angles between the central ring and the two pendant rings are 11.46 (8) and 2.06 (8)° while the pendant rings make a dihedral angle of 10.14 (8)°.
doi:10.1107/S1600536811045399
PMCID: PMC3238860  PMID: 22199713
7.  4-Chloro-2-[(E)-(4-fluoro­phen­yl)imino­meth­yl]phenol 
In the title Schiff base mol­ecule, C13H9ClFNO, the benzene rings are twisted slightly with respect to each other, making a dihedral angle of 7.92 (2)°. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, an infinite chain is formed along the c-axis direction by π–π stacking inter­actions between the phenyl rings and the six-membered hydrogen-bonded ring of neighboring Schiff base ligands [centroid–centroid distances of 3.698 (2) and 3.660 (3) Å]. Neighboring chains are linked into a three-dimensional supra­molecular structure by C—H⋯O and C—H⋯F hydrogen bonds.
doi:10.1107/S1600536813033278
PMCID: PMC3914085  PMID: 24526988
8.  2-[(E)-(5-Chloro-2-methyl­phen­yl)imino­meth­yl]-4-methyl­phenol 
In the mol­ecule of the title Schiff base compound, C15H14ClNO, the two benzene rings are twisted with respect to each other, with a dihedral angle of 35.0 (3)°; an intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, weak C—H⋯π inter­actions between methyl groups and chloro­phenyl rings link the mol­ecules into supra­molecular chains running along the a axis.
doi:10.1107/S1600536813019454
PMCID: PMC3793828  PMID: 24109415
9.  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
10.  (E)-4-[(1,5-Dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)imino­meth­yl]-2-meth­oxy­phenyl 4-bromo­benzene­sulfonate 
In the title compound, C25H22BrN3O5S, the central benzene ring makes dihedral angles of 4.41 (10), 67.09 (9) and 62.05 (10)°, respectively, with the pyrazolone, bromo­benzene and terminal phenyl rings. The dihedral angle between the pyrazolone and phenyl rings is 57.75 (11)°. In the crystal, two pairs of C—H⋯O hydrogen bonds link the mol­ecules into inversion dimers. A weak intra­molecular C—H⋯O hydrogen bonds is also observed.
doi:10.1107/S1600536812010057
PMCID: PMC3344000  PMID: 22589909
11.  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
12.  2-Bromo-4-chloro-6-[(E)-(2-chloro­phen­yl)imino­meth­yl]phenol 
The title compound, C13H8BrCl2NO, was obtained by reaction of 3-bromo-5-chloro­salicylaldehyde and 2-chloro­benzenamine in methanol. The mol­ecule displays an E configuration with respect to the imine C=N double bond. The dihedral angle between the two benzene rings is 4.57 (11)°. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond. In the crystal structure, mol­ecules are linked by inter­molecular C—H⋯O hydrogen-bonding inter­actions into zigzag chains running parallel to the b axis. Inter­molecular Br⋯Cl [3.5289 (11) Å] and Cl⋯Cl [3.5042 (12) Å] inter­actions are present.
doi:10.1107/S1600536809007181
PMCID: PMC2968929  PMID: 21582411
13.  (E)-2-({2-[(E)-(Hy­droxy­imino)­meth­yl]phen­oxy}meth­yl)-3-o-tolyl­acrylonitrile 
In the title compound, C18H16N2O2, the dihedral angle between the mean planes through the two benzene rings is 56.8 (6)°. 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 0.047 (1) Å for the hy­droxy­imino O atom. In the crystal, the mol­ecules are linked into cyclic centrosymmetric dimers with R 2 2(6) motifs via O—H⋯N hydrogen bonds.
doi:10.1107/S1600536812001481
PMCID: PMC3275232  PMID: 22347088
14.  (E)-2-[(4-Chloro­phen­yl)imino­meth­yl]-4-(trifluoro­meth­oxy)phenol 
The title compound, C14H9ClF3NO2, crystallizes in a phenol–imine tautomeric form, with a strong intra­molecular O—H⋯N hydrogen bond. The dihedral angle between the two benzene rings is 47.62 (9)°. In the crystal, mol­ecules are linked into chains along the c axis by C—H⋯O hydrogen bonds, and weak C—H⋯π inter­actions involving both benzene rings are also observed.
doi:10.1107/S1600536809040690
PMCID: PMC2971205  PMID: 21578304
15.  2-[(E)-(2-Amino­phen­yl)imino­meth­yl]-5-(dimethyl­amino)phenol 
The mol­ecule of the title compound, C17H21N3O, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the planes of the two benzene rings is 50.96 (11)° and a strong intra­molecular O—H⋯N hydrogen bond is present. An inter­molecular N—H⋯O hydrogen-bonding inter­action stabilizes the crystal structure.
doi:10.1107/S1600536809015773
PMCID: PMC2969689  PMID: 21583100
16.  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
17.  2-((E)-{4-[Bis(4-eth­oxy­phen­yl)amino]­phen­yl}imino­meth­yl)phenol 
In the title Schiff base mol­ecule, C29H28N2O3, the three terminal benzene rings are twisted by 73.84 (15), 81.25 (16) and 12.1 (2)° with respect to the central benzene ring. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, mol­ecules are linked via weak C—H⋯π inter­actions into a three-dimensional supra­molecular architecture.
doi:10.1107/S1600536814003201
PMCID: PMC3998452  PMID: 24765014
18.  2-[1-({2-[1-(2-Hy­droxy-5-{[meth­yl(phen­yl)amino]­meth­yl}phen­yl)ethyl­idene­amino]­eth­yl}imino)­eth­yl]-4-{[meth­yl(phen­yl)amino]­meth­yl}phenol 
Mol­ecules of the title compound, C34H38N4O2, lie across crystallographic inversion centres. The crystal packing can be described by alternating zigzag chains along the c axis in which the molecules are linked by van der Waals interactions. There is an intra­molecular O—H⋯N hydrogen bond and the two benzene rings in the asymmetric unit make a dihedral angle of 79.81 (6)°.
doi:10.1107/S1600536812017904
PMCID: PMC3344659  PMID: 22590421
19.  4-Bromo-2-[(E)-(2-{2-[(2-{[(E)-5-bromo-2-hy­droxy­benzyl­idene]amino}­phen­yl)sulfan­yl]ethyl­sulfan­yl}phen­yl)imino­meth­yl]phenol 
The asymmetric unit of the title compound, C28H22Br2N2O2S2, comprises half of a Schiff base ligand, the whole mol­ecule being generated by a crystallographic inversion center located at the mid-point of the C—C bond of the central methyl­ene segment. Intra­molecular O—H⋯N and O—H⋯S hydrogen bonds make S(6) and S(5) ring motifs, respectively. In the crystal, there are no significant inter­molecular inter­actions.
doi:10.1107/S1600536812034071
PMCID: PMC3435662  PMID: 22969535
20.  (E)-4-Fluoro-2-[(4-hy­droxy­pheneth­yl)imino­meth­yl]phenol 
The title compound, C15H14FNO2, has an E conformation about the C=N bond, which facilitates the formation of an intra­molecular O—H⋯N hydrogen bond. The F atom is disordered over two adjacent sites in a 0.65 (7):0.35 (7) ratio. The dihedral angle between the benzene ring planes is 14.2 (2)°. In the crystal, mol­ecules are linked by O—H⋯O hydrogen bonds, forming C(14) [010] chains.
doi:10.1107/S1600536811055875
PMCID: PMC3275018  PMID: 22346963
21.  2-[(E)-(2,4-Dimethyl­phen­yl)imino­meth­yl]phenol 
The asymmetric unit of the title compound, C15H15NO, contains two independent mol­ecules, both of which exist in trans configurations with respect to the C=N bonds [1.278 (2) and 1.279 (2) Å]. In each mol­ecule, intra­molecular O—H⋯N hydrogen bonds generate S(6) ring motifs. In one mol­ecule, the benzene rings form a dihedral angle of 13.38 (9)°, while in the other mol­ecule the dihedral angle is 30.60 (10)°. In the crystal, the two independent mol­ecules are linked via weak inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536811026110
PMCID: PMC3212320  PMID: 22090977
22.  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
23.  {4-Chloro-2-[(2-hy­droxy­eth­yl)imino­meth­yl]phenolato}{4-chloro-2-[(2-oxido­eth­yl)imino­meth­yl]phenolato}cobalt(III) 
In the title mononuclear cobalt(III) compound, [Co(C9H8ClNO2)(C9H9ClNO2)], the CoII atom is six-coordinated by two imine N atoms, two phenolate O atoms, and one hy­droxy and one oxide O atom from two Schiff base ligands, forming an octa­hedral geometry. In the crystal structure, adjacent mol­ecules are linked through inter­molecular O—H⋯O hydrogen bonds. The 2-oxidoethyl group is disordered over two positions in a 0.638 (3):0.362 (3) ratio.
doi:10.1107/S1600536810033088
PMCID: PMC3008055  PMID: 21588541
24.  (E)-2-[(4-Ethoxy­phen­yl)imino­meth­yl]-4-methoxy­phenol 
In the mol­ecule of the title compound, C16H17NO3, the aromatic rings are oriented at a dihedral angle of 29.25 (8)°. An intra­molecular O—H⋯N hydrogen bond results in the formation of a nearly planar [maximum deviation 0.034 (13) Å] six-membered ring, which is oriented at dihedral angles of 0.91 (1) and 28.91 (12)° with respect to the aromatic rings. The title mol­ecule is a phenol–imine tautomer, as evidenced by C—O, C—N and C—C bond lengths. In the crystal, mol­ecules are linked by inter­molecular C—H⋯O hydrogen bonds that generate C(8) chains.
doi:10.1107/S1600536809040586
PMCID: PMC2971308  PMID: 21578305
25.  (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

Results 1-25 (198703)