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1.  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
2.  2-[(2,4-Dimethyl­phen­yl)imino­meth­yl]-3,5-dimethoxy­phenol 
X-ray analysis reveals that the title Schiff base compound, C17H19NO3, possesses both OH and NH tautomeric character in its mol­ecular structure. The occupancies of the enol and keto tautomers are 0.62 (3) and 0.38 (3), respectively. The presence of the minor keto form could not be confirmed from the IR spectrum. The mol­ecule is approximately planar, the dihedral angle between the planes of the two aromatic rings being 6.97 (8)°. The mol­ecular structure of the major component is stabilized by an intra­molecular O—H⋯N hydrogen bond, which generates an S(6) ring motif (N—H⋯O hydrogen bond in the minor component).
doi:10.1107/S1600536809021278
PMCID: PMC2969358  PMID: 21582851
3.  (E)-3-[(4-Butyl­phen­yl)imino­meth­yl]benzene-1,2-diol 
The title compound, C17H19NO2, exists as an enol–imine tautomer. The dihedral angle between the two benzene rings is 4.6 (2)°. The mol­ecular structure is stabilized by intramol­ecular O—H⋯O and O—H⋯N hydrogen bonds which generate S(5) and S(6) ring motifs, respectively. In the crystal, mol­ecules are linked into centrosymmetric dimers by pairs of O—H⋯O hydrogen bonds. In addition, C—H⋯π inter­actions involving both benzene rings are observed.
doi:10.1107/S1600536809029316
PMCID: PMC2977352  PMID: 21583691
4.  (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
5.  3-[(2,4-Dichloro­phen­yl)imino­meth­yl]-2-hydr­oxy-5-methyl­benzaldehyde 
The title compound, C15H11Cl2NO2, is a Schiff base which adopts the phenol–imine tautomeric form in the solid state, being stabilized by a strong intra­molecular O—H⋯N hydrogen bond. The mol­ecule is almost planar (r.m.s. deviation for all non-H atoms = 0.049 Å), displaying a dihedral angle of 3.1 (3)° between the planes of the two aromatic rings.
doi:10.1107/S1600536809018303
PMCID: PMC2969673  PMID: 21583199
6.  (E)-2-[(4-Fluoro­phen­yl)imino­meth­yl]-5-methoxy­phenol 
In the mol­ecule of the title compound, C14H12FNO2, the aromatic rings are oriented at a dihedral angle of 48.17 (1)°. An intra­molecular O—H⋯N hydrogen bond results in the formation of a six-membered ring. The title mol­ecule is a phenol–imine tautomer, as evidenced by the C—O [1.351 (3) Å], C—N [1.282 (3) Å], and C—C [1.416 (3)–1.445 (3) Å] bond lengths. In the crystal, mol­ecules are linked by inter­molecular C—H⋯π inter­actions.
doi:10.1107/S1600536810000474
PMCID: PMC2979905  PMID: 21579745
7.  (E)-1-[(3-Bromo­phen­yl)imino­meth­yl]naphthalen-2-ol 
The title compound, C17H12BrNO, exists in an enol–imine form and the mol­ecular structure features an intra­molecular O—H⋯N hydrogen bond. The dihedral angle between the benzene ring and the naphthalene ring system is 17.27 (15)°.
doi:10.1107/S1600536812034824
PMCID: PMC3435811  PMID: 22969657
8.  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
9.  (E)-3-[(3-Bromo­phen­yl)imino­meth­yl]benzene-1,2-diol: a combined X-ray and computational structural study 
The title compound, C13H10BrNO2, exists as an enol–imine form in the crystal and adopts an E configuration with respect to the C=N double bond. The mol­ecule is close to planar, with a dihedral angle of 6.88 (14)° between the aromatic rings. Intra­molecular O—H⋯N and O—H⋯O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. The crystal structure is stabilized by inter­molecular O—H⋯O hydrogen-bond inter­actions, forming R 2 2(10) and R 2 2(20) chains along [100]. ab initio Hartree–Fock (HF), density-functional theory (DFT) and semi-empirical (AM1 and PM3) calculations and full-geometry optimizations were also performed. Although there are some discrepancies between the experimental and calculated parameters, caused presumably by the O—H⋯O hydrogen-bond inter­actions, there is an acceptable general agreement between them.
doi:10.1107/S1600536809035053
PMCID: PMC2970385  PMID: 21577870
10.  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
11.  3-[(E)-(4-Ethyl­phen­yl)imino­meth­yl]benzene-1,2-diol 
The title compound, C15H15NO2, adopts the enol–imine tautomeric form. The dihedral angle between the two benzene rings is 48.1 (1)°. Intra­molecular O—H⋯N and O—H⋯O hydrogen bonds generate S(6) and S(5) ring motifs, respectively. In the crystal, mol­ecules are linked into centrosymmetric R 2 2(10) dimers via pairs of O—H⋯O hydrogen bonds and the dimers may interact through very weak by π–π inter­actions [centroid–centroid distance = 4.150 (1) Å]. The ethyl group is disordered over two orientations, with occupancies of 0.587 (11) and 0.413 (11).
doi:10.1107/S1600536809029924
PMCID: PMC2977215  PMID: 21583717
12.  4-Chloro-2-[(E)-(2-chloro­phen­yl)imino­meth­yl]phenol 
The title compound, C13H9Cl2NO, was crystallized from a methanol solution of 5-chloro­salicylaldehyde and o-chloro­aniline. The mol­ecule displays a trans configuration with respect to the imine C=N double bond. The N atom is involved in an intra­molecular O—H⋯N hydrogen bond. The two aromatic rings are essentially coplanar, the dihedral angle between them being 7.1 (1)°. A C—H⋯π inter­action is present in the crystal.
doi:10.1107/S1600536809003924
PMCID: PMC2968492  PMID: 21582175
13.  (E)-2-[(4-Iodo­phen­yl)imino­meth­yl]-6-methyl­phenol 
The title compound, C14H12INO, adopts the phenol–imine tautomeric form. The dihedral angle between the aromatic rings is 20.6 (3)°. The mol­ecular conformation is stabilized by an intra­molecular O—H⋯N hydrogen bond while in the crystal, weak inter­molecular C—H⋯O hydrogen bonds link the mol­ecules into a zigzag chain parallel to the b axis.
doi:10.1107/S160053681001826X
PMCID: PMC3006692  PMID: 21587810
14.  2-[(2,6-Diethyl­phen­yl)imino­meth­yl]-N-(2-methoxy­phen­yl)aniline 
The title anilide–imine compound, C24H26N2O, features an intra­molecular N—H⋯N hydrogen bond involving the imine and anilide groups to generate an S(6) ring motif. The mol­ecule displays an E configuration about the imine C=N double bond, with the dihedral angle between the two benzene rings being 86.5°. The packing is stabilized by three different C—H⋯π inter­actions.
doi:10.1107/S1600536809037969
PMCID: PMC2970353  PMID: 21577981
15.  (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
16.  (E)-2-[(3-Fluoro­phen­yl)imino­meth­yl]-4-(trifluoro­meth­oxy)phenol 
The title compound, C14H9F4NO2, is a Schiff base which adopts the phenol–imine tautomeric form in the solid state. The H atom is located on the hydr­oxy O atom rather than on the N atom. This H atom is involved in a strong intra­molecular O—H⋯N hydrogen bond. The mol­ecule is almost planar, the angle between the benzene rings being 2.14 (13)°.
doi:10.1107/S1600536810002989
PMCID: PMC2983675  PMID: 21580285
17.  2-{[3-Chloro-4-(4-chloro­phen­oxy)phen­yl]imino­meth­yl}-4-nitro­phenol 
In the title compound, C19H12Cl2N2O4, the imine bond length of 1.257 (6) Å is typical of a double bond. The dihedral angle between the para-nitro benzene ring and the central benzene ring is 12.06 (3)° and that between the central benzene and the para-chloro benzene ring is 73.81 (2)°. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked together by two pairs of C—H⋯O interactions (to the same O atom acceptor), forming inversion dimers. A short Cl⋯Cl contact [3.232 (4) Å] is observed.
doi:10.1107/S1600536813012518
PMCID: PMC3685046  PMID: 23795065
18.  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
19.  (E)-1-[(2-Fluoro­phen­yl)imino­meth­yl]-2-naphthol–(Z)-1-[(2-fluoro­phen­yl)amino­methyl­idene]naphthalen-2(1H)-one (0.57/0.43) 
The title Schiff base compound, 0.57C17H12FNO·0.43C17H12FNO, reveals both the enol (OH) and keto (NH) tautomeric forms with occupancies of 0.57 (6) and 0.43 (6), respectively. The tautomeric forms are stabilized by intra­molecular O—H⋯N (enol) and N—H⋯O (keto) hydrogen bonds. The dihedral angle between the naphthalene ring system and the benzene ring is 32.76 (1)°.
doi:10.1107/S1600536810014777
PMCID: PMC2979202  PMID: 21579219
20.  2-[(4-Bromo­phen­yl)imino­meth­yl]-3,5-dimethoxy­phenol 
There are two independent mol­ecules in the asymmetric unit of the title compound, C15H14BrNO3, with very similar geometrical parameters. Each mol­ecule adopts the phenol–imine tautomeric form, with strong intra­molecular O—H⋯N hydrogen bonds. The two mol­ecules are non-planar, the dihedral angles between the two aromatic rings being are 24.6 (2) and 30.30 (13)°.
doi:10.1107/S1600536809011416
PMCID: PMC2968797  PMID: 21582634
21.  (E)-2-Eth­oxy-6-[(4-ethoxy­phen­yl)imino­meth­yl]phenol 
In the asymmetric unit of the title compound, C17H19NO3, there are three independent mol­ecules, which are align nearly parallel to each other and adopt the phenol-imine tautomeric form. In each mol­ecule, an intra­molecular O—H⋯N hydrogen bond results in the formation of an S(6) ring motif. The dihedral angles between the aromatic rings in the three independent mol­ecules are 13.55 (2), 21.24 (2) and 46.26 (1)°. C—H⋯π inter­actions are also observed in the crystal structure.
doi:10.1107/S1600536810006434
PMCID: PMC2983578  PMID: 21580427
22.  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
23.  2-[(E)-(2-Chloro­phen­yl)imino­meth­yl]-6-methyl­phenol 
The title compound, C14H12ClNO, a Schiff base derived from 3-methyl­salicyl­aldehyde, crystallizes in the phenol–imine tautomeric form with an E conformation for the imine functionality. The mol­ecule is not planar, the dihedral angle between the aromatic rings being 36.38 (5)°. The hy­droxy H atom is involved in a strong intra­molecular O—H⋯N hydrogen bond, generating an S(6) ring.
doi:10.1107/S1600536810033969
PMCID: PMC3008053  PMID: 21588779
24.  (E)-2-[(2-Ethyl­phen­yl)imino­meth­yl]-6-methoxy­phenol 
The mol­ecule of the title compound, C16H17NO2, adopts the phenol–imine tautomeric form with a strong intra­molecular O—H⋯N hydrogen bond and an E conformation with respect to the azomethine C=N bond. The dihedral angle between the aromatic rings is 21.23 (9)°. The ethyl group is disordered over two orientations with occupancies of 0.598 (6) and 0.402 (6). In the crystal, the mol­ecules are linked into chains along the b axis by C—H⋯π inter­actions.
doi:10.1107/S1600536809055573
PMCID: PMC2979675  PMID: 21579722
25.  2-[(4-Chloro­phen­yl)imino­meth­yl]hydro­quinone 
The title compound, C13H10ClNO2, exists in the phenol–imine form in the crystal, and the aromatic rings are oriented at a dihedral angle of 2.82 (9)°. An intra­molecular O—H⋯N hydrogen bond results in the formation of a planar six-membered ring. In the crystal structure, inter­molecular O—H⋯O hydrogen bonds link the mol­ecules into chains.
doi:10.1107/S1600536809015396
PMCID: PMC2977821  PMID: 21583958

Results 1-25 (126840)