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1.  Diethyl 2,2′-bis­(hy­droxy­imino)-3,3′-(hydrazinediyl­idene)dibutano­ate 
Each mol­ecule of the title compound, C12H18N4O6, is located on an inversion centre at the mid-point of the central N—N bond. The azo groups C=N of the Schiff base group have an E conformation and the azo groups in the oxime C=N—O groups have a Z conformation. O–H⋯O hydrogen bonds link neighbouring mol­ecules into infinite monolayers perpendicular to the a axis.
doi:10.1107/S1600536812007398
PMCID: PMC3297900  PMID: 22412703
2.  6,6′-Dieth­oxy-2,2′-[propane-1,3-diyl­dioxy­bis(nitrilo­methyl­idyne)]diphenol 
The complete mol­ecule of the title compound, C21H26N2O6, is generated by a crystallographic twofold axis and adopts a trans configuration with respect to the azomethine group. The two benzene rings are almost perpendicular to one another, making a dihedral angle of 89.53 (3)°. In the mol­ecular structure, pairs of intra­molecular O—H⋯N hydrogen bonds generate two six-membered rings. The crystal structure is further stabilized by inter­molecular C—H⋯O hydrogen bonds, which link four adjacent mol­ecules into a network structure.
doi:10.1107/S1600536810003430
PMCID: PMC2983666  PMID: 21580287
3.  2,2′-[Octane-1,8-diyldioxy­bis(nitrilo­methyl­idyne)]diphenol 
The complete mol­ecule of the title compound, C22H28N2O4, is generated by a crystallographic inversion centre at the mid-point of the central C—C bond. The two benzene rings are parallel to each other with a perpendicular inter­planar spacing of 1.488 (2) Å. Intra­molecular O—H⋯N hydrogen bonds generate two six-membered rings with S(6) motifs. In the crystal, weak inter­molecular C—H⋯O hydrogen bonds link neighbouring mol­ecules into an infinite three-dimensional network, which is further stabilized by weak C—H⋯π inter­actions.
doi:10.1107/S160053680905466X
PMCID: PMC2980204  PMID: 21580119
4.  4-({4-[1-(Methoxy­imino)eth­yl]anilino}(phen­yl)methyl­ene)-3-methyl-2-phenyl-1H-pyrazol-5(4H)-one 
In the title compound, C26H24N4O2, the dihedral angles between the central pyrazole ring and the other three benzene rings are 40.02 (3), 77.51 (5) and 55.72 (3)°. A strong intra­molecular N—H⋯O hydrogen bond forms a six-membered ring with an S(6) motif. In the crystal structure, a weak inter­molecular C—H⋯N inter­action with graph-set motif R 2 2(8) and C—H⋯O hydrogen bonds link each mol­ecule to three others, forming an infinite two-dimensional supra­molecular structure.
doi:10.1107/S1600536809048326
PMCID: PMC2971858  PMID: 21578846
5.  Bis[(E)-4-bromo-2-(ethoxy­imino­meth­yl)phenolato-κ2 N,O 1]copper(II) 
The title compound, [Cu(C9H9BrNO2)2], is a centrosymmetric mononuclear copper(II) complex. The Cu atom is four-coordinated in a trans-CuN2O2 square-planar geometry by two phenolate O and two oxime N atoms from two symmetry-related N,O-bidentate (E)-4-bromo-2-(ethoxy­imino­meth­yl)phenolate oxime-type ligands. An inter­esting feature of the crystal structure is the centrosymmetric inter­molecular Cu⋯O inter­action [3.382 (1) Å], which establishes an infinite chain structure along the b axis.
doi:10.1107/S160053680904433X
PMCID: PMC2971190  PMID: 21578195
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.  1,3-Bis[(4-methylbenzylidene)amino­oxy]propane 
The title bis­oxime compound, C19H22N2O2, synthesized by the reaction of 4-methyl-2-hydroxy­benzaldehyde with 1,3-bis­(amino­oxy)propane in ethanol, adopts a V-shaped conformation. The dihedral angle between the rings is 84.59 (3)°. The mol­ecule is disposed about a crystallographic twofold rotation axis, with one C atom lying on the axis. In the crystal, mol­ecules are packed by C—H⋯π(Ph) inter­actions, forming chains.
doi:10.1107/S1600536809042147
PMCID: PMC2971336  PMID: 21578377
8.  2,2′-[1,1′-(Octane-1,8-diyldioxy­dinitrilo)diethyl­idyne]diphenol 
The title compound, C24H32N2O4, has a crystallographic inversion centre at the mid-point of the central C—C bond. At each end of the mol­ecule, intra­molecular O—H⋯N hydrogen bonds generate six-membered S(6) ring motifs. The crystal structure is stabilized by pairs of weak inter­molecular C—H⋯O hydrogen bonds that link neighbouring mol­ecules into R 2 2(40) ring motifs, which in turn form infinite one-dimensional supra­molecular ribbon structures.
doi:10.1107/S1600536809033959
PMCID: PMC2970437  PMID: 21577782
9.  1,3-Bis[(4-nitro­benzyl­idene)amino­oxy]propane 
The complete molecule of title compound, C17H16N4O6, is generated by a crystallographic twofold axis. Within the mol­ecule, the two benzene units are approximately perpen­dicular, making a dihedral angle of 85.91 (4)°. In the crystal, mol­ecules are linked into a three-dimensional network by C—H⋯O hydrogen bonds and short O⋯O and N⋯O inter­actions, with distances of 2.998 (2) and 2.968 (3) Å, respectively.
doi:10.1107/S1600536809031316
PMCID: PMC2969883  PMID: 21577551
10.  Bis{(E)-4-chloro-2-[(2-chloro-3-pyrid­yl)imino­methyl-κN]phenolato-κO}copper(II) 
In the title complex, [Cu(C12H7Cl2N2O)2], the CuII center is tetra­coordinated by two phenolic O and two azomethine N atoms from two bidentate 4-chloro-2-[(2-chloro-3-pyrid­yl)imino­meth­yl]phenolate (L) ligands. In the crystal structure, the CuII atom has a distorted square-planar coordination environment. The dihedral angles between the benzene and pyridyl rings are 54.39 (3) and 80.14 (4)°, indicating that the pyridine ring has a considerably weaker steric hindrance. The packing of the mol­ecule is controlled by C—H⋯π(Ph) inter­actions and short O⋯Cl inter­actions [3.196 (4) Å], linking the mol­ecules into a chain-like structure along the c axis.
doi:10.1107/S1600536809029651
PMCID: PMC2977127  PMID: 21583310
11.  2,2′-[1,1′-(Decane-1,10-diyldioxy­dinitrilo)diethyl­idyne]diphenol 
The salen-type bis-oxime title compound, C26H36N2O4, lies about a crystallographic inversion centre. Classical intra­molecular O—H⋯N hydrogen bonds generate two S(6) ring motifs. In the crystal structure, pairs of weak inter­molecular C—H⋯O hydrogen bonds link adjacent mol­ecules into an infinite one-dimensional supra­molecular structure.
doi:10.1107/S1600536809029341
PMCID: PMC2977177  PMID: 21583684
12.  N-Benzoyl-N′-(2-chloro-3-pyrid­yl)thio­urea 
The title compound, C13H10ClN3OS, was prepared by the reaction of 3-amino-2-chloropyridine with benzoyl isothio­cyanate at room temperature. The thio­urea group makes dihedral angles of 47.17 (5) and 51.88 (4)°, respectively, with the benzene and pyridyl rings, while the angle between the benzene and pyridine rings is 8.91 (3)°. Inter­molecular hydrogen-bond inter­actions link neighbouring mol­ecules into an infinite supra­molecular structure.
doi:10.1107/S1600536809027081
PMCID: PMC2977241  PMID: 21583593
13.  2,2′-Dichloro-1,1′-[(pentane-1,5-diyldi­oxy)bis­(nitrilo­methyl­idyne)]dibenzene 
The mol­ecule of the title compound, C19H20Cl2N2O2, which lies across a crystallographic inversion centre, adopts a linear configuration. The dihedral angle between the two halves of the mol­ecule is 5.14 (2)°. In the crystal structure, inter­molecular C—H⋯O hydrogen bonds link neighbouring mol­ecules into an infinite zigzag chain supra­molecular structure.
doi:10.1107/S1600536809027433
PMCID: PMC2977418  PMID: 21583594
14.  Bis{(E)-4-bromo-2-[(2-chloro-3-pyrid­yl)imino­meth­yl]phenolato-κ2 N,O}copper(II) 
In the title complex, [Cu(C12H7BrClN2O)2], the CuII center is tetra­coordinated by two phenolate O and two azomethine N atoms from two independent bidentate 4-bromo-2-[(2-chloro-3-pyrid­yl)imino­meth­yl]phenolate (L) ligands. In the crystal structure, the CuII atom has a distorted square-planar coordination environment. The inter­planar dihedral angles between the benzene and pyridine rings in the individual ligands are 63.83 (4) and 54.43 (3)°, indicating the pyridine ring to have considerably weaker steric hindrance.
doi:10.1107/S1600536809027792
PMCID: PMC2977463  PMID: 21583395
15.  {2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphtholato}nickel(II) 
In the title complex, [Ni(C26H22N2O4)], the NiII atom has a slight distortion toward tetra­hedral geometry from a square-planar structure, coordinated by two O and two N atoms of the tetra­dentate salen-type bis­oxime 2,2′-[1,1′-(ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphtholate (L 2−) unit, with a mean deviation of 0.022 Å from the N2O2 plane. The N- and O-donor atoms are mutually cis. The dihedral angle between two naphthalene systems of the L 2− ligand is 67.59 (4)°. The crystal structure is stabilized by inter­molecular C—H⋯O and C—H⋯π inter­actions, which link neighbouring mol­ecules into extended chains along the b axis.
doi:10.1107/S1600536809023149
PMCID: PMC2969427  PMID: 21582728
16.  {2,2′-[1,1′-(Ethyl­enedioxy­dinitrilo)diethyl­idyne]di-1-naphtholato}copper(II) 
The title complex, [Cu(C26H22N2O4)], is isostructural with its Ni analogue. All intramolecular distances and angles are very similar for the two structures, whereas the packing of the molecules, including C—H⋯O and C—H⋯π interactions, are slightly different.
doi:10.1107/S1600536809023010
PMCID: PMC2969428  PMID: 21582727
17.  2,2′-[1,1′-(Heptane-1,7-diyldioxy­dinitrilo)diethyl­idyne]di-1-naphthol 
The mol­ecule of the title compound, C31H34N2O4, adopts an L-shaped configuration, in which the naphthalene units are approximately perpendicular, making a dihedral angle of 87.89 (3)°. Intramolecular H-bonds are formed between the OH substituents and the N atoms at each end of the molecule. In the crystal structure, each mol­ecule links six other mol­ecules into an infinite three-dimensional network supra­molecular structure, which is built from one-dimensional zigzag chains via weak C—H⋯π stacking and inter­molecular C—H⋯O hydrogen bonds.
doi:10.1107/S1600536809022727
PMCID: PMC2969467  PMID: 21582894
18.  2,2′-{1,1′-[Butane-1,4-diyl­bis(oxy­nitrilo)]di­ethylidyne}di-1-naphthol 
The title compound, C28H28N2O4, was synthesized by the reaction of 2-acetyl-1-naphthol with 1,4-bis­(amino­oxy)butane in ethanol. The molecule, which lies about an inversion centre, adopts a linear structure, in which the oxime groups and naphthalene ring systems assume an anti conformation. The intra­molecular inter­planar distance between parallel naphthalene rings is 1.054 (3) Å. Intra­molecular O—H⋯N hydrogen bonds are formed between the oxime nitro­gen and hydr­oxy groups.
doi:10.1107/S160053680901647X
PMCID: PMC2969537  PMID: 21583113
19.  2,2′-{1,1′-[Pentane-1,5-diylbis(oxy­nitrilo)]diethylidyne}di-1-naphthol 
The title compound, C29H30N2O4, adopts a distorted Z configuration with respect to the oxime group, which is almost coplanar with the adjacent naphthalene ring [dihedral angle = 4.11 (2)°]. There is one half-mol­ecule in the asymmetric unit, with a crystallographic twofold rotation axis passing through the central C atom of the –CH=N—O-(CH)5—O—N=CH– bridge. Within the mol­ecule, the dihedral angle formed by the two naphthalene rings is 79.08 (3)°, and there are two intra­molecular O—H⋯N hydrogen bonds.
doi:10.1107/S1600536809016584
PMCID: PMC2969628  PMID: 21583105
20.  5,5′-Dimeth­oxy-2,2′-[(pentane-1,5-diyl­dioxy)bis­(nitrilo­methyl­idyne)]diphenol 
The mol­ecule of the title compound, C21H26N2O6, which lies across a crystallographic inversion centre, crystallizes with two unique half-molecules in the symmetric unit and adopts a linear configuration and the imino group is coplanar with the aromatic ring, making a dihedral angle of 3.26 (3)°. Strong intra­molecular O—H⋯N and weak inter­molecular O—H⋯O and C—H⋯O hydrogen bonds and weak inter­molecular π–π stacking inter­actions [centroid–centroid distance = 4.419 (2) Å]establish an infinite three-dimensional supra­molecular structure.
doi:10.1107/S1600536809014986
PMCID: PMC2977826  PMID: 21583963
21.  Bis(N,N-dimethyl­formamide-κO)bis­(2,4,6-trinitro­phenolato-κ2 O 1,O 2)copper(II) 
The mol­ecule of the title complex, [Cu(C6H2N3O7)2(C3H7NO)2], is disposed about a crystallographic centre of symmetry. The CuII cation is six-coordinated by two phenolate O atoms and two ortho-nitro O atoms of two picrate units and by two carbonyl O atoms from two coordinated dimethyl­formamide mol­ecules, forming a distorted octa­hedral geometry.
doi:10.1107/S1600536808039846
PMCID: PMC2967846  PMID: 21581467
22.  2,2′-{1,1′-[Pentane-1,5-diyl­bis(oxy­nitrilo)]­diethyl­idyne}diphenol 
In the title compound, C21H26N2O4, there is half a mol­ecule in the asymmetric unit with a crystallographic twofold rotation axis passing through the central C atom of the –CH=N—O—(CH2)5—O—N=CH– bridge. The dihedral angle formed by the two benzene rings is 80.85 (2)°. Strong intra­molecular O—H⋯N and C—H⋯O hydrogen bonds help to establish the molecular conformation. There are also weak inter­molecular π–π stacking inter­actions between neighbouring benzene rings [centroid–centroid separation = 3.502 (3) Å].
doi:10.1107/S160053680803136X
PMCID: PMC2959680  PMID: 21580925
23.  2,2′-[1,1′-(Hexane-1,6-diyldioxy­dinitrilo)diethyl­idyne]diphenol 
The molecule of the title compound, C22H28N2O2, lies across an inversion centre with one half-mol­ecule in the asymmetric unit. The mol­ecule adopts an E configuration with respect to the azomethine C=N bond and the imino group is coplanar with the aromatic ring. Within the mol­ecule, the planar units are parallel, but extend in opposite directions from the hexa­methyl­ene bridge. There are intra­molecular O—H⋯N hydrogen bonds between the hydroxyl groups and the oxime N atoms. There are also weak inter­molecular C—H⋯O bonds that link each mol­ecule to two others, forming chains along the a axis.
doi:10.1107/S1600536808024902
PMCID: PMC2960586  PMID: 21201709
24.  1,1′-[(Hexane-1,6-diyldi­oxy)bis­(nitrilo­methyl­idyne)]dinaphthalene 
The title compound, C28H28N2O2, was synthesized by condensation of 1-naphthaldehyde with 1,6-bis­(amino­oxy)hexane in ethanol. The mol­ecule is disposed about a crystallographic centre of symmetry. In the crystal structure, mol­ecules are linked through strong inter­molecular π–π stacking inter­actions [interplana distance = 2.986 (2) Å], forming a three-dimensional network.
doi:10.1107/S160053680801920X
PMCID: PMC2962038  PMID: 21203125

Results 1-24 (24)