PMCC PMCC

Search tips
Search criteria

Advanced
Results 1-25 (213634)

Clipboard (0)
None

Related Articles

1.  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
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.  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
4.  (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
5.  (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
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.  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
8.  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
9.  (E)-1-[2-Hy­droxy-4,6-bis­(meth­oxy­meth­oxy)phen­yl]-3-[3-meth­oxy-4-(meth­oxy­meth­oxy)phen­yl]prop-2-en-1-one 
The title compound, C22H26O9, crystallizes with two independent mol­ecules in the asymmetric unit in which the dihedral angles between the two benzene rings are 21.4 (2) and 5.1 (2)°. An intra­molecular O—H⋯O hydrogen bond occurs in each mol­ecule. Inter­molecular C—H⋯O hydrogen bonds stabilize the crystal structure.
doi:10.1107/S1600536811041213
PMCID: PMC3247344  PMID: 22219962
10.  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
11.  N′-[(E)-5-Bromo-2-hy­droxy-3-meth­oxy­benzyl­idene]benzohydrazide monohydrate 
The title compound, C15H13BrN2O3·H2O, exists in an E conformation with respect to the azo­methane C=N double bond. The benzene and phenyl rings form dihedral angles of 0.46 (2) and 4.90 (3)°, respectively with the central C(=O)N2C unit. An intra­molecular O—H⋯N hydrogen bond occurs. In the crystal, some hydrazide mol­ecules are replaced by mol­ecules of the 6-bromo isomer. The Br atom from this admixture was refined to give a partial occupancy of 0.0443 (19). A supra­molecular network is built in the lattice by means of inter­molecular N—H⋯O and two O—H⋯O inter­actions together with non-classical C—H⋯O inter­actions involving the lattice water mol­ecule stacking the mol­ecules along the b-axis direction.
doi:10.1107/S1600536813030572
PMCID: PMC3885046  PMID: 24454222
12.  (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
13.  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
14.  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
15.  (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
16.  (E)-3-(8-Benz­yloxy-2,3-dihydro-1,4-benzodioxin-6-yl)-1-[2-hy­droxy-4,6-bis­(meth­oxy­meth­oxy)phen­yl]prop-2-en-1-one 
In the title mol­ecule, C28H28O9, the phenol and the benzene rings adjacent to the α,β-unsaturated ketone unit are inclined at 9.15 (13)° to each other. The terminal phenyl ring is oriented with respect to the phenol ring at a dihedral angle of 85.88 (13)°. In the crystal, the methyl­ene C atoms of the dihydro­dioxine ring are disordered over two sites with an occupancy ratio of 0.463 (18):0.537 (18), and both disordered components of the dihydro­dioxine ring adopt twisted-chair conformations. An intra­molecular O—H⋯O hydrogen bond and weak inter­molecular C—H⋯O hydrogen bonds are present in the crystal structure.
doi:10.1107/S160053681100924X
PMCID: PMC3100013  PMID: 21754185
17.  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
18.  (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
19.  (2,4-Dihy­droxy-6-meth­oxy­phen­yl)(3,5-dihy­droxy­phen­yl)methanone monohydrate 
The title benzophenone compound, C14H12O6·H2O, was isolated from the bark of Garcinia hombroniana Pierre (Guttiferae). The mol­ecule is twisted, the dihedral angle between the two benzene rings being 59.13 (7)°. The meth­oxy group is approximately coplanar with the attached benzene ring, with a C—O—C—C torsion angle of 1.91 (18)°. The water mol­ecule is disordered over two positions in a 0.555 (19):0.445 (19) ratio. An intra­molecular O—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by inter­molecular O—H⋯O hydrogen bonds. These inter­actions link the mol­ecules into sheets parallel to the ac plane. The sheets are stacked along the b axis by π–π inter­actions, with centroid–centroid distances of 3.6219 (7) Å. A weak O—H⋯π inter­action was also noted.
doi:10.1107/S1600536811037913
PMCID: PMC3201278  PMID: 22065717
20.  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
21.  1-[(Bromo­meth­yl)(phen­yl)meth­ylene]-2-(2,4-dinitro­phen­yl)hydrazine 
The title compound, C14H11BrN4O4, comprises two crystallographically independent mol­ecules (A and B) in the asymmetric unit. In mol­ecule B, intra­molecular bifurcated N—H⋯O and N—H⋯Br hydrogen bonds and in mol­ecule A, an intra­molecular N—H⋯O hydrogen bond generate S(6) ring motifs. The dihedral angle between the phenyl and benzene rings is 5.44 (6) in mol­ecule A and 7.63 (6)° in mol­ecule B. The ortho- and meta-nitro substituents make dihedral angles of 6.67 (15) and 2.26 (15)° to the attached benzene ring in mol­ecule A and 6.37 (17) and 5.81 (16)° in mol­ecule B. The Br atom in mol­ecule B is disordered over two positions with a refined site-occupancy ratio of 0.61 (3):0.39 (3). Inter­esting features of the crystal structure are the short Br⋯N [3.257 (3)–3.294 (4) Å], Br⋯O [3.279 (3)–3.307 (4) Å] and O⋯O [2.9319 (16)–2.9995 (16) Å] contacts, which are shorter than the sum of the van der Waals radii of these atoms. The crystal structure is further stabilized by inter­molecular C—H⋯O and π–π inter­actions [centroid–centroid distances = 3.6643 (8)–3.8514 (8) Å].
doi:10.1107/S1600536809016225
PMCID: PMC2969738  PMID: 21583090
22.  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
23.  N′-[(E)-5-Bromo-2-hy­droxy-3-meth­oxy­benzyl­idene]-4-meth­oxy­benzohydrazide monohydrate 
In the title compound, C16H15BrN2O4·H2O, the hydrazide mol­ecule is nearly planar, with a largest deviation from the mean plane through the non-H atoms of 0.106 (4) Å and a dihedral angle between the benzene rings of 1.98 (16)°. This mol­ecule adopts an E conformation about the C=N bond and an intra­molecular O—H⋯N hydrogen bond increases the rigidity. In the crystal, some mol­ecules of the title hydrazide are replaced by mol­ecules of its 6-bromo isomer, and the Br atom from this admixture mol­ecule was refined to give a partial occupancy of 0.0523 (13). The hydrazide and water mol­ecules are linked through classical N—H⋯O and O—H⋯O hydrogen bonds, forming layers parallel to (110). C—H⋯π inter­actions are also present.
doi:10.1107/S1600536812033806
PMCID: PMC3470184  PMID: 23125628
24.  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
25.  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

Results 1-25 (213634)