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1.  (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
2.  2-[(E)-(5-Amino-2,3-diphenyl­quinoxalin-6-yl)imino­meth­yl]-4-chloro­phenol 
The title Schiff base compound, C27H19ClN4O, features two intra­molecular O—H⋯N and N—H⋯N hydrogen bonds involving the hydr­oxy and amino groups to generate S(6) and S(5) ring motifs, respectively. In the crystal structure, weak inter­molecular N—H⋯O and C—H⋯N inter­actions, together with π–π contacts [centroid–centroid distances = 3.6294 (11)–3.6881 (11) Å], link neighboring mol­ecules.
doi:10.1107/S1600536808020023
PMCID: PMC2962046  PMID: 21203131
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-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
5.  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
6.  (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
7.  1,4-Bis[(2-pyridyl­eth­yl)imino­meth­yl]benzene 
In the title compound, C22H22N4, the centroid of the benzene ring is located on an inversion centre. The dihedral angle between the benzene and pyridine rings is 10.94 (5)°. The crystal structure displays weak inter­molecular C—H⋯N hydrogen bonding and C—H⋯π inter­actions.
doi:10.1107/S1600536811009809
PMCID: PMC3099859  PMID: 21754192
8.  5-Diethyl­amino-2-[(E)-(4-eth­oxy­phen­yl)imino­meth­yl]phenol 
The title compound, C19H24N2O2, adopts the phenol–imine tautomeric form. An intra­molecular O—H⋯N hydrogen bond results in the formation of a six-membered ring. The aromatic rings are oriented at a dihedral angle of 17.33 (16)°. Inter­molecular C—H⋯π inter­actions occur in the crystal.
doi:10.1107/S1600536811004533
PMCID: PMC3051950  PMID: 21522358
9.  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
10.  (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
11.  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
12.  4-Bromo-2-{(E)-3-[1-(hydroxy­imino)eth­yl]phenyl­imino­meth­yl}phenol 
In the title compound, C15H13BrN2O2, he oxime unit adopts an E conformation with respect to the O—H group. A classical intra­molecular O—H⋯N hydrogen bond results in the formation of a six-membered ring. The crystal structure is stabilized by inter­molecular O—H⋯N hydrogen bonds between the hydr­oxy groups and the oxime N atoms. In addition, the crystal structure also features short inter­molecular Br⋯Br short contacts with a distance of 3.8768 (5) Å.
doi:10.1107/S1600536809048855
PMCID: PMC2971802  PMID: 21578872
13.  2-Bromo-4-chloro-6-{(E)-[4-(diethyl­amino)­phen­yl]imino­meth­yl}phenol 
In the title compound, C17H18BrClN2O, the dihedral angle between the aromatic rings is 3.0 (1)°. The methyl­ethanamine group assumes an extended conformation. An intra­molecular O—H⋯N hydrogen bond generates an S(6) ring motif. The crystal packing is stabilized by C—H⋯π and π–π [centroid–centroid distances = 3.691 (1) and 3.632 (1) Å] inter­actions.
doi:10.1107/S1600536810033738
PMCID: PMC3008048  PMID: 21588747
14.  4-Bromo-2-[(E)-(4-chloro­phen­yl)imino­meth­yl]phenol 
In the title compound, C13H9BrClNO, the dihedral angle between the substituted benzene rings is 43.90 (11)°. Strong intra­molecular O—H⋯N hydrogen bonds generate S(6) ring motifs. The crystal structure features short intemolecular Br⋯Br [3.554 (2) Å] and Cl⋯Cl [3.412 (2) Å] contacts. The crystal packing is further stabilized by inter­molecular C—H⋯O and C—H⋯π inter­actions.
doi:10.1107/S1600536811004417
PMCID: PMC3052075  PMID: 21522356
15.  2-[1-(3-Amino­phenyl­imino)­eth­yl]phenol 
The title compound, C14H14N2O, exists as the enol–imine tautomer. A strong intra­molecular hydrogen bond between O and N atoms forms a six-membered ring with an S(6) graph-set motif, which is approximately coplanar with the phenol ring, the inter­planar angle being 3.4 (3)°. In the crystal, inter­molecular C—H⋯O hydrogen bonds and N—H⋯π inter­actions link the mol­ecules into infinite chains along [100].
doi:10.1107/S1600536811017624
PMCID: PMC3120413  PMID: 21754803
16.  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
17.  (E)-2-[1-(3-Amino-4-chloro­phenyl­imino)eth­yl]-4-bromo­phenol 
The title Schiff base compound, C14H12BrClN2O, exists in an E configuration with respect to the central C=N double bond. The amino group adopts a pyramidal configuration. The dihedral angle between the two benzene rings is 76.88 (10)° and an intra­molecular O—H⋯N hydrogen bond forms a six-membered ring, generating an S(6) ring motif. In the crystal structure, mol­ecules are linked into chains along [010] via N—H⋯O hydrogen bonds. The presence of π–π inter­actions [centroid–centroid distance = 3.6244 (12) Å] further stabilizes the crystal structure.
doi:10.1107/S1600536810009773
PMCID: PMC2983940  PMID: 21580701
18.  (2E)-2-Hydroxy­imino-N′-[(E)-2-pyridyl­methyl­ene]propanohydrazide 
In the title compound, C9H10N4O2, the pyridine ring is twisted by 16.5 (1)° from the mean plane defined by the remaining non-H atoms. An intra­molecular N—H⋯N inter­action is present. In the crystal, inter­molecular O—H⋯N and N—H⋯O hydrogen bonds link mol­ecules into layers parallel to the bc plane. The crystal packing exhibits π–π inter­actions indicated by the short distance of 3.649 (1) Å between the centroids of the pyridine rings of neighbouring mol­ecules.
doi:10.1107/S1600536809034400
PMCID: PMC2970200  PMID: 21577872
19.  2-Hydroxy­imino-1-phenyl­ethanone thio­semicarbazone monohydrate 
In the title thio­semicarbazone derivative, C9H10N4OS·H2O, intra­molecular N—H⋯N hydrogen bonds result in the formation of two nearly coplanar five- and six-membered rings, which are also almost coplanar with the adjacent phenyl ring. The oxime group has an E configuration and is involved in inter­molecular O—H⋯O hydrogen bonding as a donor. In the crystal structure, intra­molecular O—H⋯S and N—H⋯N and inter­molecular O—H⋯O and N—H⋯S hydrogen bonds generate edge-fused R 2 2(8) and R 4 1(11) ring motifs. The hydrogen-bonded motifs are linked to each other to form a three-dimensional supra­molecular network.
doi:10.1107/S1600536808004947
PMCID: PMC2960784  PMID: 21201956
20.  2-[(E)-(5-Amino-2,3-diphenyl­quinoxalin-6-yl)imino­meth­yl]-4-bromo­phenol 
The title compound, C27H19BrN4O, is a mono-anil Schiff base ligand. Three intra­molecular O—H⋯N and N—H⋯N hydrogen bonds involving the hydr­oxy and amino groups generate S(6) and S(5) ring motifs, respectively. In the crystal structure, weak inter­molecular N—H⋯O and C—H⋯O hydrogen bonds together with π–π inter­actions [centroid–centroid distances = 3.628 (3)–3.729 (3) Å] link neighboring mol­ecules.
doi:10.1107/S1600536808017716
PMCID: PMC2961755  PMID: 21202904
21.  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
22.  4-[(9-Ethyl-9H-carbazol-3-yl)imino­meth­yl]phenol 
In the title compound, C21H18N2O, the dihedral angle between the phenol ring and the carbazole system is 39.34 (2)°. Inter­molecular O—H⋯N hydrogen bonds and C—H⋯π and π–π inter­actions [centroid–centroid distances = 3.426 (2) and 3.768 (2) Å] stabilize the crystal structure.
doi:10.1107/S1600536810046167
PMCID: PMC3011571  PMID: 21589488
23.  2-(Thio­phen-2-yl)-N-(4-{(E)-[2-(thio­phen-2-yl)eth­yl]imino­meth­yl}benzyl­idene)ethanamine 
In the crystal of the centrosymmetric title compound, C20H20N2S2, mol­ecules are linked by head-to-tail C—H⋯N hydrogen bonds, resulting in chains extending along the a axis. Three additional C—H⋯π inter­molecular inter­actions give rise to a herringbone packing motif which extends along the c axis. The C—H⋯N inter­actions provide links between the sheets.
doi:10.1107/S1600536811009810
PMCID: PMC3099871  PMID: 21754193
24.  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
25.  Bis{4-chloro-2-[(2-hy­droxy­eth­yl)imino­meth­yl]phenolato}nickel(II) monohydrate 
The title mononuclear nickel(II) complex, [Ni(C9H9ClNO2)2]·H2O, was obtained by the reaction of 5-chloro­salicyl­aldehyde, 2-amino­ethanol and nickel nitrate in methanol. The Ni atom is six-coordinated by two phenolate O, two imine N and two hy­droxy O atoms from two crystallographically different Schiff base ligands, forming an octa­hedral geometry. In the crystal, mol­ecules are linked through inter­molecular O—H⋯O and O—H⋯Cl hydrogen bonds.
doi:10.1107/S1600536811031680
PMCID: PMC3200802  PMID: 22058855

Results 1-25 (271960)